Siesta Key Vacation Rentals - 5-Stars, Top Locations!

The location was everything I was looking for, being super close to the beach. Also, the apartment was…

10th August 2019 by Chris NeCamp

The location was everything I was looking for, being super close to the beach. Also, the apartment was very cozy and quaint, a perfect location for a getaway for two! Dan was super helpful and accommodating making our stay outstanding.

I want to thank Daniel, James and the staff for such a great weekend, the house is amazing, white wine…

7th August 2019 by Carlos Santamaría

I want to thank Daniel, James and the staff for such a great weekend, the house is amazing, white wine on the table, and the most amazing beach! We really enjoy our stay. Thank you guys and greetings from Colombia!!

Absolutely loved our trip to siesta key and our stay at the old man and the sea inn. Took full advantage…

3rd July 2019 by Brandon Lambert

Absolutely loved our trip to siesta key and our stay at the old man and the sea inn. Took full advantage of the outdoor lounging area and the grill. Made my family several fantastic surf and turf dinners during our stay. And Daniel and his staff are+ Moregreat,friendly folks. Will be back again

Wonderful place and location service was top notch. Will look at using Gertrude rentals for future travels….

24th June 2019 by Miranda Morgan

Wonderful place and location service was top notch. Will look at using Gertrude rentals for future travels.

Our stay was absolutely perfect! Daniel was a wonderful host- we especially loved the wine and crackers…

29th May 2019 by Katie Dovas

Our stay was absolutely perfect! Daniel was a wonderful host- we especially loved the wine and crackers awaiting our arrival:) Unit was very close to the beach- smaller then expected but perfect for just the two of us and very clean. The icing on+ Morethe cake was Daniel allowing us to have an unexpected late checkout due to a flight delay- I would refer his Siesta Key getaway to everyone I know- we cant wait to go back!

Review #355

22nd May 2019 by indymomof2 from Indianapolis

The rental is small, we had two units for four of us (my mother, myself and two teenage girls), but it's perfect for just two people. The location is perfect and the other guest and owners were very nice. Cresent Beach is the nicest part of Siesta+ MoreKey Beach and if you walk out into the water to the Point of Rocks there are wonderful places to fish and look at tidal pool sea creatures (wear shoes though). This rental is perfect for a low key, laid back Florida vacation.

Review #357 Clean, cozy and relaxing…

22nd May 2019

We stayed at this rental for a long weekend in mid-October, and it was wonderful! The unit is not large but very comfortable for a couple or family of 4 or less. The unit is very nicely appointed and beautifully decorated. Some of the extras that we+ Moreenjoyed are the gas grill, short stroll to a gorgeous white sand beach and that you have all you need to make quick, easy meals. If you don't want to cook, lots of places to eat nearby, and a Pubix is a short car ride away, too. The water pressure in the large shower is excellent, which is something you don't always find in rentals. Daniel was exception when it came to answering my questions, and the check-in/out process was easy! Thank you, Daniel - we'll be back!

Review #358 Can’t wait to go back

22nd May 2019

My wife and I had a fabulous time here! Close to the beach. We snorkelled, paddle boarded, and relaxed!! We love Siesta Key and this is the best place we have stayed over the years. Recommend Dan and Jon!

Review #359 Great location & value

22nd May 2019 by mab12 from CA

Siesta Key is picture perfect, and this rental is perfect for beach love rs. Great value for what youre getting -- very clean, nice new furnishings, steps from the beach, beautiful location. Could not ask for more. Dan is exceptional to deal with.+ MoreWould return for sure. Recommend highly.

Review #361 Loved it!!!

22nd May 2019 by Marti from GA

We had such a great time! The beaches are the best! The condo was very nice. New furnishings and decor but still had that old Florida charm. Everything was easy and uncomplicated. No fuss, just fun and relaxing. Dan and John were very accommodating+ Moreand easy going. They could charge more, but don't tell them I said that!

Review #363 Comfortable and close to the beach.

22nd May 2019

This unit is not directly on the beach but the beach access is across the street and the walk is not long. We stayed with our kids and it was just right. Daniel was very helpful and accommodating. Great deal for the price. My only recommendation+ More(and this had nothing to do with the unit) arrive and stake your plot on the beach early! Otherwise you may have to walk down a little bit to find a spot. Also the name of the beach "Point of Rocks" concerned me because of my kids, but it was very kid friendly. No water shoes needed.

Review #364 Clean & Close to the Beach

22nd May 2019

We had sold our family condo (a two bedroom unit in The Casarina) after two plus decades and wanted to stay on Siesta Key Beach over the Christmas to New Year Holiday. Casarina condo association bi-laws only allow rentals of a month or longer. So+ Morefinding a reliably clean and close condo on Siesta Key Beach that will rent for just a week is difficult. Most of the weekly rentals are worn, torn, or a distance from the beach with hands-off or remote owners, who don't attend to the details of maintenance or customer questions. We really appreciated working with Daniel Jones! Daniel is amazingly timely with his follow-through and feedback! You'll love working with him!We rented Old Man and the Sea Unit B. It's a second floor, one bedroom, living room/Kitchen combined room, and bathroom unit, that is 10 steps from the sand path to the Siesta Key beach. For a couple it is sufficiently sized but if you have children or others staying with you you'll need a larger unit. The parking/Car port is right by the stairs so unpacking and loading up the car on arrival and departure was quick. Ten years from now I may not be carrying suitcases up and down stairs but at 62 I managed the stairs and my better half's 75 lb. suitcases. You will want to bring folding lounge chairs for the beach but store them in your car's trunk between trips to the beach....you'll save walking them up and down the stairs and prevent neighbors from hijacking them. The bed's mattress was firm and comfortable. The bathroom was small but the shower was large. The towels were adequate and clean. Be sure to bring laundry detergent and laundry softener for the washer/dryer that is on the ground floor around back or the car port. The back stairs from Unit B are the best way to access the ground floor laundry from the second floor unit. There is no dishwasher in the kitchen. But we only ate breakfast/brunch in the unit and ate out every night as most visitors do. There are ample dishes, glasses, cups, and silverware that come with the unit. The sheets were clean, the furniture was clean, but the new wood floors had sand remaining on them. We swept up the sand and recommend a long-handled floor Swifter be added to the cleaning tools (vacuum and broom) stored in the bedroom closet. Closet space is small but we hung a week's worth of cloths with no problem. The right front burner on the stove didn't work but Daniel responded quickly to our report. All kitchen appliances worked well but the filters for the coffee maker were the wrong size so a full pot of coffee didn't drain. We adapted and made smaller pots of coffee. it would help if the specifics of coffee filter size and model was posted on or near the coffee maker so replacements could be easily matched up and acquired, if not automatically replaced between tenants. We highly recommend that all renters use the outside ground floor shower, which is just outside the laundry area, to shower off sand before returning to their units from the beach!!! This shower is a great feature that you've got to use or you'll bring powder white sand into your unit. The unit has an iron but the iron is not listed on the unit's inventory. You will need to bring the following items:Hair DryerFolding Chairs for the BeachLaundry DetergentFabric Softener Old Man and the Sea is a "beachy condo", not the Siesta Key luxury condo we had owned for over two decades. Nonetheless it is a very clean and close condo; immediately adjacent to Siesta Key Beach with an owner who is highly attentive and responsive! This unit is ideal for a couple who want to be immediately accessible to Siesta Key Beach for stays under a month.

Review #365 Wonderful place to stay just steps from the beach!

22nd May 2019

This was a wonderful place for our family to stay last minute! The place was clean, tidy, and cute. The owner was very accommodating and easy to work with. When you walk outside of the door you are just steps from the path to the beach - it was a+ Moreperfect location! We would absolutely stay again.

Review #366 AMAZING as always!!

22nd May 2019

This is my second year renting from Daniel and both years have been amazing!! Great locations, beautiful homes, and of course easy access to the beach!! My only complaint for Old Man was the parking on the A/B side was very tricky!! We made it work+ Morethough and loved our stay!!

Review #367 What a find!

22nd May 2019

I literally stumbled on this location in search of a venue to take my wife on a surprise anniversary vacation. What a find! My wife and I have stayed at Old Man on the Sea Inn the past 2 years now. We have come to call this our home away from home+ Moreas that is truly where we feel we are when we have stay there. I have not personally met Daniel but I can say that I have communicated with him both by email and by phone and he is very personable and accommodating. I spoke with Daniel a few times before our first visit trip as I wanted to make certain that the unit I stayed in would have an oven to prepare our meals. Daniel contacted me (while he was on his honeymoon with his new wife!) trying to accommodate my request as the unit we were to stay in was the only unit that did not have an oven and it would require a special order to install one due to space limitations. As an alternative, he offered to have a counter top convection oven or a slow cooker delivered to the unit. I told him we would try to make due. Who needed one after all? The unit had a cook top and the grill outside was always available. We have stayed in both a one bedroom and a two bedroom unit at this location and have seen all of the units thanks to the generosity of our friendly neighbors. I prefer to I bedroom for just two people but I can tell you that all of the units are exactly as advertised and represented by the photos with all of them being clean and tastefully furnished and decorated. The grounds are well-maintained. The shared washer and dryer are newer models and were always available when we needed to use them. The coded check in and check out policy is very convenient as well.

Review #368 Awesome stay!

22nd May 2019 by Jordan Hardy from Nashville,TN.

Daniel accommodated all of my bridal party and family for our wedding weekend! We had a wonderful time and both houses were so close to the beach and everything we needed! Great place to stay!

Review #372 Can’t wait to go back

22nd May 2019

My wife and I had a fabulous time here! Close to the beach. We snorkelled, paddle boarded, and relaxed!! We love Siesta Key and this is the best place we have stayed over the years. Recommend Dan and Jon!

Review #373 Great location & value

22nd May 2019 by mab12 from CA

Siesta Key is picture perfect, and this rental is perfect for beach love rs. Great value for what youre getting -- very clean, nice new furnishings, steps from the beach, beautiful location. Could not ask for more. Dan is exceptional to deal with.+ MoreWould return for sure. Recommend highly.

Review #375 Loved it!!!

22nd May 2019 by Marti from GA

We had such a great time! The beaches are the best! The condo was very nice. New furnishings and decor but still had that old Florida charm. Everything was easy and uncomplicated. No fuss, just fun and relaxing. Dan and John were very accommodating+ Moreand easy going. They could charge more, but don't tell them I said that!

Review #377 Comfortable and close to the beach.

22nd May 2019

This unit is not directly on the beach but the beach access is across the street and the walk is not long. We stayed with our kids and it was just right. Daniel was very helpful and accommodating. Great deal for the price. My only recommendation+ More(and this had nothing to do with the unit) arrive and stake your plot on the beach early! Otherwise you may have to walk down a little bit to find a spot. Also the name of the beach "Point of Rocks" concerned me because of my kids, but it was very kid friendly. No water shoes needed.

Review #378 Clean & Close to the Beach

22nd May 2019 by Paul Richards from North Canton, Ohio

We had sold our family condo (a two bedroom unit in The Casarina) after two plus decades and wanted to stay on Siesta Key Beach over the Christmas to New Year Holiday. Casarina condo association bi-laws only allow rentals of a month or longer. So+ Morefinding a reliably clean and close condo on Siesta Key Beach that will rent for just a week is difficult. Most of the weekly rentals are worn, torn, or a distance from the beach with hands-off or remote owners, who don't attend to the details of maintenance or customer questions. We really appreciated working with Daniel Jones! Daniel is amazingly timely with his follow-through and feedback! You'll love working with him!We rented Old Man and the Sea Unit B. It's a second floor, one bedroom, living room/Kitchen combined room, and bathroom unit, that is 10 steps from the sand path to the Siesta Key beach. For a couple it is sufficiently sized but if you have children or others staying with you you'll need a larger unit. The parking/Car port is right by the stairs so unpacking and loading up the car on arrival and departure was quick. Ten years from now I may not be carrying suitcases up and down stairs but at 62 I managed the stairs and my better half's 75 lb. suitcases. You will want to bring folding lounge chairs for the beach but store them in your car's trunk between trips to the beach....you'll save walking them up and down the stairs and prevent neighbors from hijacking them. The bed's mattress was firm and comfortable. The bathroom was small but the shower was large. The towels were adequate and clean. Be sure to bring laundry detergent and laundry softener for the washer/dryer that is on the ground floor around back or the car port. The back stairs from Unit B are the best way to access the ground floor laundry from the second floor unit. There is no dishwasher in the kitchen. But we only ate breakfast/brunch in the unit and ate out every night as most visitors do. There are ample dishes, glasses, cups, and silverware that come with the unit. The sheets were clean, the furniture was clean, but the new wood floors had sand remaining on them. We swept up the sand and recommend a long-handled floor Swifter be added to the cleaning tools (vacuum and broom) stored in the bedroom closet. Closet space is small but we hung a week's worth of cloths with no problem. The right front burner on the stove didn't work but Daniel responded quickly to our report. All kitchen appliances worked well but the filters for the coffee maker were the wrong size so a full pot of coffee didn't drain. We adapted and made smaller pots of coffee. it would help if the specifics of coffee filter size and model was posted on or near the coffee maker so replacements could be easily matched up and acquired, if not automatically replaced between tenants. We highly recommend that all renters use the outside ground floor shower, which is just outside the laundry area, to shower off sand before returning to their units from the beach!!! This shower is a great feature that you've got to use or you'll bring powder white sand into your unit. The unit has an iron but the iron is not listed on the unit's inventory. You will need to bring the following items:Hair DryerFolding Chairs for the BeachLaundry DetergentFabric Softener Old Man and the Sea is a "beachy condo", not the Siesta Key luxury condo we had owned for over two decades. Nonetheless it is a very clean and close condo; immediately adjacent to Siesta Key Beach with an owner who is highly attentive and responsive! This unit is ideal for a couple who want to be immediately accessible to Siesta Key Beach for stays under a month.

Review #412 Can’t wait to go back

22nd May 2019

My wife and I had a fabulous time here! Close to the beach. We snorkelled, paddle boarded, and relaxed!! We love Siesta Key and this is the best place we have stayed over the years. Recommend Dan and Jon!

Review #413 Great Location and accomodation

22nd May 2019 by on October 12, 2013

The Location is right by the beach and the Unit was comfy, clean and well maintained. We will definitely be back!

Review #416 Comfortable and close to the beach.

22nd May 2019

This unit is not directly on the beach but the beach access is across the street and the walk is not long. We stayed with our kids and it was just right. Daniel was very helpful and accommodating. Great deal for the price. My only recommendation+ More(and this had nothing to do with the unit) arrive and stake your plot on the beach early! Otherwise you may have to walk down a little bit to find a spot. Also the name of the beach "Point of Rocks" concerned me because of my kids, but it was very kid friendly. No water shoes needed.

This was our third stay at this property and all three visits have been absolutely wonderful. The location…

5th May 2019 by Ginger Martin

This was our third stay at this property and all three visits have been absolutely wonderful. The location is steps from the beach and a peaceful retreat. We love it here and it’s become our annual getaway. Daniel and his staff are so personable+ Moreand the property offers everything you need. Highly recommended!!

Let me start by saying that when I visit Siesta Key there isn’t another place that I will stay. This…

29th April 2019 by Tonya Morris

Let me start by saying that when I visit Siesta Key there isn’t another place that I will stay. This is my 5th time staying with Gertrude Rentals. As soon as Daniel found out I was getting married he went above and beyond to make our stay+ Morespecial. He always checks in several times to ensure your stay is exactly what you wanted. I have stayed in 3 different condos while staying and each one has been clean, well kept, and beautifully decorated. The convenience to the beach beats any other. It’s also a great location because it is not as busy as the public beach. This is the place to stay in Siesta Key. If I could give this 10 stars I would!

Review #380 Location, location

13th January 2019 by Ted from Wisconsin

Great proximity to the beach, restaurants, groceries, and activities.

Review #379 R&R – so relaxing!

7th January 2019 by Karen from Durham, NC

We loved this cozy bungalow-feel spot just steps from the beach! Daniel's attention to all the things that "make" a vacation - even a short one - were terrific. The extra touches and attention were greatly appreciated! Wonderfully quiet, relaxing -+ Morelots of nearby restaurants on the Key and just a few minutes away on the mainland, together with a fully-equipped kitchen and terrific gas grill (shared) - and on-site laundry was a bonus. We hope to return! Thank you!!

Review #381 Lovely Place

30th October 2018 by Suzanne Zampetti from Old Man and the Sea - Unit D

This was such a lovely place to stay. It is step away from the most beautiful and pristine beach. Very quiet location. The unit was clean and comfortable. Daniel is very accommodating. Has everything you need for a low key, relaxing vacation.

Review #382 Perfect Stay

23rd October 2018 by Ana Menendez from Coral Gables

We had a great time with the family during this past Memorial Weekend . We managed to get to the beach even thou the weather was not great! Danny was the perfect host and was always making sure that everything was just right. Would love to get back+ Moresoon.

Review #383 CRTESCENT

29th May 2018 by Nick Guile from Palm City Florida

From start to finish Gertrude rentals was extremely helpful and easy to deal with. The unit was amazing along with the perfect proximity to Crescent Beach. Across a narrow two lane street and your walking down the bath to the beach. Crescent Beach+ Morehad the most amazing sunsets and access to Poinf of Rocks was remarkable at the same time. I would recommend for anyone that is looking for a beach vacation.

Review #384 Terrific…Exactly as Advertised

21st April 2018 by CRR from Rochester, NY

Terrific spot, very clean and comfortable. Excellent location close to beach, restaurants, etc. Wonderful respite after a day exploring the area.

Review #339 Super accommodations; Location, location, location

12th March 2018 by Robert Stavins from Chicago

Thx Daniel,We had a wonderful stay at your location in Siesta Key. Steps from the beach! Minutes from town and super restaurants. Kayaking and bike rental for a small fee was a major perk!See you soon,Robert Stavins

Review #385 Family vacation

12th March 2018 by Medina from Key Largo

The place is clean and the location excellent, quiet and secure. The apartment was renovated but the structure outside needs renovation. Overall I will recommended but the price is on the high side.

Review #386 Stunning location!

21st February 2018 by John Stevens from Sarasota

gorgeous location and perfect cosy apartments. Everything we needed for our short stay. So close to the amazing beach and only short walk to the shops/bars/restaurants. Big Water fish market being our favorite!!

Review #340 8 Steps to Paradise

27th January 2018 by Vincent Cassata from Old Man and the Sea

Enjoyed my stay there and couldn't have been more pleased. Daniel was a pleasure to deal with and the accommodations were perfect for a short getaway on Siesta key. I would definitely stay there again when I'm back in Sarasota.

Review #341 Great time!

27th December 2017 by Beth from MARYLAND

Loved our stay here! The ocean was amazing... thanks for the toys! Comfy beds! Even had wine waiting for us!

Review #387 43748

4th December 2017 by Mark Stevens from Moscow, Russia

Wonderful in every way. I have nothing bad to say about this wonderful guest house in this stunning place. Many thanks to Daniel.

Review #388 PERFECT Honeymoon!!

4th December 2017 by Jackie from Indiana

Our stay was so much more than we hoped for! The room was very cute and clean. Perfect size for just 2 people. I loved how close it was to the beach. We utilized the provided beach chairs every evening to walk to the quiet, not very busy beach at+ Moreall, to watch the sunset every night. I loved how everything you need is within walking distance. This was our 1st visit to the area, but definitely won't be our last. Daniel was so easy to work with. On our last day we called to see if we could stay another night. He took care of us fast and simple. I do believe this is the 1st rental I have ever stayed out where there was not a "check out to do" list. I plan on renting with them whenever possible!

Review #389 Great Place!!!

29th November 2017 by Pam Todaro from Willis, Tx

We would stay here again! Your place is very clean which is what I like. And decorated very nicely.Great Place!!!

Review #390 Perfect for Us

27th November 2017 by Wendy O'Connor from Siesta Key Old Man & The Sea Unit C

We were pleasantly surprised by how wonderful everything about our accommodations were. The unit was perfect for my husband and I and our 2 dogs. Easy check-in, just enter a code. Everything we needed was in the unit plus some extras. The beautiful+ MoreSiesta Key Beach entrance was literally across a small dead end street. Place was clean, bed was comfortable and was nice that there were no units below us. Would definitely rent again!

Review #391 Best vacation ever!

14th November 2017 by Sheila B from Old man by the sea. Siesta Key Florida. Unit c

Would highly recommend staying at Old Man By The Sea. Very clean & affordable. Walking distance to beach & restaurants & shops. The complimentary bottle of wine, waters & snacks was a really nice touch. Daniel Jones & his staff do a great job. Can't+ Morewait to return.

Review #392 Old man and the sea

7th November 2017 by Sean from Austin, TX

My stay here was peaceful. I enjoyed being so close to such a gorgeous beach. The outdoor shower was a huge plus for me. The room was well stocked and very clean. All my interactions with staff were friendly and professional. I appreciated that the+ Morecheck in/out process was so simple too. I would definitely recommend this spot to a friend.

Review #393 UNIT B

27th August 2017 by Meagan J from Old Man and the Sea Unit C

Beautifully decorated and very clean! Location is perfect, in a quiet neighborhood, and just a very short walk to the beach. Parking was super convenient. Definitely one of the best and most relaxing vacations I have ever been on thanks to Old Man+ Moreand the Sea Inn. Daniel is a great host and it is evident that he cares about his property and his guests. Highly recommend.

Review #394 Returning Guest

20th August 2017 by Mark from Central FL

Thank you Daniel Jones. As usual,The unit was clean and well equipped, and we really enjoyed our stay. Daniel was very accommodating and we plan to stay again soon.

Review #395 Absolutely perfect

15th August 2017 by Tamara Star from Boulder colorado

Clean and beautiful. Exactly what the photos and description said! Daniel was super responsive. I'll definitely be back! I'll also explore his other locations. It was wonderful all the way around.

Review #342 Even better than last year

31st July 2017 by H. Watford from Lakeland, FL

Just left yesterday and already want to return. From the convenient beach access to the quiet nestled feel of the property, there is no better place to stay. This is my second year at this location. Nothing beats daytime Sun and evening strolls+ Morealong the rocks and searching the tide pools. Rent a bike and explore the key. It's a great vacation!

Review #338 Great place!

15th July 2017 by Marsha from Michigan

A great place to stay if you want to be very close to the beach. Our unit was just right for 2 people. The unit was clean with a small kitchen with all dishes and pots and pans. The owner Daniel was easy to work with and always returned any emails+ Moreand phones you left for him. He is also very good at giving recommendations food or activities. We made our reservations for next year before we left this year. We stayed in our unit for 5 weeks this year and LOVE it! We met some very nice people who will remain our friends. It is a great area to vacation at!

Review #343 Even better than last year

12th July 2017 by H. Watford from Lakeland, FL

Just left yesterday and already want to return. From the convenient beach access to the quiet nestled feel of the property, there is no better place to stay. This is my second year at this location. Nothing beats daytime Sun and evening strolls+ Morealong the rocks and searching the tide pools. Rent a bike and explore the key. It's a great vacation!

Review #344 Paradise!!

12th July 2017 by Zainy from Ashburn, VA

Absolutely a great find!!! We were so pleased to stay at Dan's place. It was perfect and everything you need is there. The space is perfect for two individuals. The beach is a two minute walk-- gorgeous beach!! All of the main attractions is closeby+ Morewith car. I would stay here again-- did not want to leave!!! Thank you Dan!!

Review #345 Hated to leave!

18th June 2017 by Julie from Pittsburgh, PA

What a wonderful stay! To start, Daniel is a very down-to-earth guy....ALWAYS responded promptly to phone calls and emails, and always was always courteous and complete in providing answers! As for the actual rental....very cute and VERY+ Moreclean....and I am big on cleanliness! We didn't spend a lot of time indoors because there's so much yo do and see in the area. The whole stay was just so enjoyable! I would definitely recommend Gertrude Rentals to anyone planning a trip! Daniel was a pleasure to work with! (Only one drawback to The Old Man and The Sea building....that "shack" of a house that blocks the view of the ocean! If it weren't there....how perfect it would be!

Review #396 Best vacation EVER

13th May 2017 by Catherine from Clinton, CT

I honestly can't say enough about Daniel and our wonderful stay with Gertrude Rentals. It was hands down the best and most relaxing vacation my husband and I have ever had. Not only would we recommend to all our friends and family but we look+ Moreforward to staying at other Gertrude Rental locations. I've never had a host so committed to us getting the most of our vacation, and for that I'm truly thankful. From the atmosphere, location, and ease, to the welcoming basket we didn't have an ounce of stress! The unit was in a quiet neighborhood, all of the guest we encountered were happy and welcoming. The beach was super close, and it was clean and very very comfortable!

Review #397 Fantastic find – no reason why not to come back!

4th May 2017 by Janell from Grand Rapids, OH

This was a fantastic find! The location couldn't have been any better. We were just steps from the beautiful Crescent Beach. We stayed in Unit "C" which had everything we needed. This upper level unit satisfied our needs for our family of 3. We were+ Moreonly a short distance from many restaurants and shops. We utilized the grill that was available on the ground level as well as the large table for our dinners. This property is located on a quiet street and was surrounded by many other well-maintained homes. The interior was very clean and updated as was the exterior of the building. The kitchen was well equipped for our cooking needs. The linens were plentiful and of good quality. There were many beach toys for kids available. There were also beach towels and chairs provided. Having a washer and dryer (no cost, just provide your own soap) available on the ground level (shared by others staying on the property) was a nice option. The owner was very helpful and the reserving and checkout process was simple. In addition, the owner also supplied us with a detailed packet of information of not only the property, but the area - very helpful! We can't think of any reason why not to come back!

Review #398 As advertised!

1st March 2017 by Les from Indiana

Great location! Quiet, close to everything you need, beach, bikes, groceries, etc. Wonderful accommodations. Would definitely recommend.

Review #346 Amazing Hospitality!!

19th February 2017 by Bill and Jennifer from Savannah, Ga

Amazing stay in Siesta Key. Dan and his team made sure that everything was perfect for us. Beach chairs, coolers, umbrellas, and even a washer and dryer just steps from beach. We had a blast and would definitely stay here again. Thanks for making+ Moreour stay so great!

Review #399 UNIT B

6th February 2017 by Patricia Hargrave from Illinois

Old man and the sea. Fun and great location. Thought it was right on the beach but not. Unit c needs a new toaster and a kitchen sink plug/strainer. Other than that, loved the beach chairs, boogie boards , grill etc. thanks!

Review #400 I made a good decision

23rd January 2017 by Gary B from Martinsburg, WV

This was my first visit to the Sarasota area. I came for baseball and the beach. I made several reservations and cancellations before came upon this place. A last minute cancellation by another party allowed my wife and I the opportunity to stay at+ MoreSiesta Key near Crescent Beach. The apartment was just what we needed. Perfect for two. Easy to find, parking included and just a hop from the beautiful beach. Daniel worked with me and gave me a hot deal, and when the apt was not exactly ready when we arrived, it was not a problem and was handled by Daniel promptly. WE were very comfortable here. Well decorated. Quiet neighborhood. Walking distance to a few vendors such as restaurants and stores. Ate at The Turtles Restaurant and the Toasted Mango Café. Not many cons to mention, maybe size of TV, but heck who needs a TV at Siesta Key. Will love to come back soon.

Review #403 Very Nice!

14th November 2016 by CM from Washington DC

Very laid-back beachy vibe, but also very clean and professionally managed. It's definitely more of an apartment than a hotel feel, but I liked that I didn't have to go through a check-in/check out process and I really liked having a separate living+ Moreroom and a full kitchen. Good parking a nice neighborhood. Would definitely go again!

Review #347 Awesome stay!

7th August 2016 by Jordan Hardy from Nashville,TN.

Daniel accommodated all of my bridal party and family for our wedding weekend! We had a wonderful time and both houses were so close to the beach and everything we needed! Great place to stay!

Review #404 Great location!

21st June 2016 by Melissa H. from Kissimmee, FL

We chose this property due to it being pet friendly. When we arrived we found the room to be very clean and quiet. While small, there was sufficient room for two adults and our dog. The bed and pillows were comfortable and clean. Plenty of towels+ Morewere available. Our only complaint was the bathroom. The bathroom and shower were both sufficient in size, the but ventilation in that room was very poor. The air conditioning vent had very little air coming out of it, and the fan vents needed to be cleaned out. It was VERY hot and humid, you could not tell you had stepped out of the shower. The only way you could cool off and get dry was to go into the bedroom. We did enjoy the close proximity to the beach access, as well the outdoor shower to rinse off after a day at the beach. Overall we would stay here again.

Review #348 amazing

13th June 2016 by Ginger Martin from Butler PA

We had an amazing time at the Old Man and the Sea. We stayed in unit B and we couldn't have been happier. The location is perfect. It's steps to the beach but yet far enough away from the village that it's peaceful and relaxing. Daniel made the+ Morecheck in and check out process easy and answered all questions before we arrived. The unit was clean and had everything that we could want. It's perfect for 2 (and a dog). I highly recommend this property!

Review #369 Perfect little rental right off the beach

13th June 2016 by indymomof2 from Indianapolis

The rental is small, we had two units for four of us (my mother, myself and two teenage girls), but it's perfect for just two people. The location is perfect and the other guest and owners were very nice. Cresent Beach is the nicest part of Siesta+ MoreKey Beach and if you walk out into the water to the Point of Rocks there are wonderful places to fish and look at tidal pool sea creatures (wear shoes though). This rental is perfect for a low key, laid back Florida vacation.

Review #349 Mr. Daniel Jones truly has a Great Place to share!

1st May 2016 by Eddie Saplala from Clarkston, Michigan

We stayed in the 1 bedroom bungalow that was very nicely decorated. It was clean with nice amenities. The entire complex was very well taken care of and very well maintained. Mr. Jones communicated w/me via email very politely and timely. It really+ Moreshows that Mr. Jones takes care of his guests and makes sure they are comfortable and happy. My wife and I were pleasantly surprised by his lovely place and his level of service. We would 1000% come back to his GEM of a place. Thank you very much for sharing your place :)

Review #350 Enjoyable stay at “the old man and the sea”

11th April 2016 by Mark Hawkins from Central Florida

Enjoyed our stay. The room was clean and comfortable. Daniel provides beach chairs and toys. Daniel was easy to work with and we hope to stay there again.

Review #401 Great Vacation and Experience

2nd April 2016 by Doug Prather from Indiana

We have really enjoyed our stay at your property. Thank you for your hospitality and the cleanliness of the unit. One suggestion would be another tv in the bedroom. That's where we stayed and no tv for basketball was tough. Competing with the kids+ Morefor the other. We would like to know a listing of all your properties. We will be back and would like the chance to work with you on another visit.

Review #402 Old man and the sea inn

17th March 2016 by Habeeb Rahman MD from New Jersey

Close to a great beach, great clean with amenities including kitchen, beach chairs and umbrella, toys for kids etc. Convenient marked parking. Dan is a great host.

Review #352 Wonderful Trip

28th December 2015 by Eddardo and Micaela Wilder from St. Louis, MO.

My wife and I had our wedding ceremony on the beach and stayed at The Old Man and the Sea. Our stay was very pleasant as we enjoyed walks on the private beach during the day and at night. We enjoyed the walks down the strip to go to the restaurants+ Moreand stores. Would highly recommend to anyone.

Review #408 “Quaint Little private space.”

19th November 2015 by cricket44314 from Akron, Ohio

Loved being here. It is so quiet and so close to the beach. Just follow the path and cross the street and you are on the beach. Everything you need is there waiting for you. Shops to buy food are close and so are places to eat. We walked and+ Morepurchased Pizza our first night there and walked back to Old Man to eat it and it was still hot. We would and probably will come back to stay here again. I have already been telling family and friends about this gem by the sea.

Review #405 Perfect Beach location in really nice neighborhood

16th August 2015 by Alexandra Frankel from New York City

Old Man and the Sea was clean and comfortable and a great value. Loved the Point of Rocks neighborhood. We've been coming to Sarasota for 15 years and never knew this area existed. We loved exploring a new place. Loved that it was right at the foot+ Morepath to beach. Crescent beach is gorgeous! Daniel was very accommodating, attentive, and easy to work with.

Review #351 Very Nice Place

29th July 2015 by Nidal from Atlanta, GA.

My wife and two kids stayed here for a week during X-mas. The location is absolutely perfect...you're a very short walk from the beach. Better yet, you're in a mostly secluded part of the Siesta Beach. The apartment itself was very well maintained,+ Morealthough it is a very tight space. Once we pulled out the sofa bed there was very little room to maneuver. Overall it was a very good place and we would not hesitate to stay here again.

Review #353 “Quaint Little private space.”

3rd July 2015 by cricket44314 from Akron, Ohio

Loved being here. It is so quiet and so close to the beach. Just follow the path and cross the street and you are on the beach. Everything you need is there waiting for you. Shops to buy food are close and so are places to eat. We walked and+ Morepurchased Pizza our first night there and walked back to Old Man to eat it and it was still hot. We would and probably will come back to stay here again. I have already been telling family and friends about this gem by the sea.

Review #406 Perfect Location!

12th May 2015 by Amy from WV

What a terrific location. Of all of our stays on Siesta Key this is by far our favorite. It is a tremendous location on the best section of the beach! I highly recommend this location!! The best and easiest check-in and check-out process EVER!

Review #407 Love…..Love….Love

15th April 2015 by Bruce and Susan Woerner from Kalamazoo, Michigan

Bruce & Susan from Kalamazoo can't wait to go back. Daniel is a charm to communicate with, very helpful as always. We invited some friends to join us on the beach from another condo in Siesta, and they are going to rent from Daniel next time too.+ MoreThe accommodations, cleanliness, furnishings and surroundings are AWESOME !! We hope to have a family trip there soon with all 20 of us. Thank you Daniel, and hug on that baby for us.

Review #354 Great location and accommodations.

4th December 2014

The Location is right by the beach and the Unit was comfy, clean and well maintained. We will definitely be back!

Review #409 Perfect little rental right off the beach

4th December 2014 by indymomof2 from Indianapolis

The rental is small, we had two units for four of us (my mother, myself and two teenage girls), but it's perfect for just two people. The location is perfect and the other guest and owners were very nice. Cresent Beach is the nicest part of Siesta+ MoreKey Beach and if you walk out into the water to the Point of Rocks there are wonderful places to fish and look at tidal pool sea creatures (wear shoes though). This rental is perfect for a low key, laid back Florida vacation.

Review #356 No surprises: as pictured, clean, great location, good service.

25th June 2014

We enjoyed this rental. It was clean and well maintained, as in the pictures. It is in a small condo complex and has been redone nicely. We really enjoyed how quiet and peaceful it was. When packing, you may wish to include things like mp3 speakers+ Moreor a DVD player (we didn't see those around) if important to you.

Review #370 No surprises: as pictured, clean, great location, good service.

25th June 2014 by SMBB6t from Columbus, Ohio

We enjoyed this rental. It was clean and well maintained, as in the pictures. It is in a small condo complex and has been redone nicely. We really enjoyed how quiet and peaceful it was. When packing, you may wish to include things like mp3 speakers+ Moreor a DVD player (we didn't see those around) if important to you.

Review #410 No surprises: as pictured, clean, great location, good service.

25th June 2014 by SMBB6t from Columbus, Ohio

We enjoyed this rental. It was clean and well maintained, as in the pictures. It is in a small condo complex and has been redone nicely. We really enjoyed how quiet and peaceful it was. When packing, you may wish to include things like mp3 speakers+ Moreor a DVD player (we didn't see those around) if important to you.

Review #371 Clean, cozy and relaxing…

19th February 2014

We stayed at this rental for a long weekend in mid-October, and it was wonderful! The unit is not large but very comfortable for a couple or family of 4 or less. The unit is very nicely appointed and beautifully decorated. Some of the extras that we+ Moreenjoyed are the gas grill, short stroll to a gorgeous white sand beach and that you have all you need to make quick, easy meals. If you don't want to cook, lots of places to eat nearby, and a Pubix is a short car ride away, too. The water pressure in the large shower is excellent, which is something you don't always find in rentals. Daniel was exception when it came to answering my questions, and the check-in/out process was easy! Thank you, Daniel - we'll be back!

Review #411 Clean, cozy and relaxing…

19th February 2014

We stayed at this rental for a long weekend in mid-October, and it was wonderful! The unit is not large but very comfortable for a couple or family of 4 or less. The unit is very nicely appointed and beautifully decorated. Some of the extras that we+ Moreenjoyed are the gas grill, short stroll to a gorgeous white sand beach and that you have all you need to make quick, easy meals. If you don't want to cook, lots of places to eat nearby, and a Pubix is a short car ride away, too. The water pressure in the large shower is excellent, which is something you don't always find in rentals. Daniel was exception when it came to answering my questions, and the check-in/out process was easy! Thank you, Daniel - we'll be back!

Review #360 Great Location and accomodation

12th October 2013

The Location is right by the beach and the Unit was comfy, clean and well maintained. We will definitely be back!

Review #374 Great Location and accomodation

12th October 2013

The Location is right by the beach and the Unit was comfy, clean and well maintained. We will definitely be back!

Review #362 Everything you need, amazing beach location…

5th October 2013

This place is spotless and beautifully decorated. All the furnishings were brand new and very comfortable. You are practically in the ocean at this location, so the location cannot be beat. For this price and comfort, it's steal. Also, during our+ Morestay, Dan and his team brought us brand new boogie boards for our use, simply bc he's a nice guy who cares about your vacation. I would definitely rent from this company again. I have used other companies and were invariably disappointed, either for something small or big, so I'm happy with Gertrude Rentals.

Review #376 Everything you need, amazing beach location…

5th October 2013

This place is spotless and beautifully decorated. All the furnishings were brand new and very comfortable. You are practically in the ocean at this location, so the location cannot be beat. For this price and comfort, it's steal. Also, during our+ Morestay, Dan and his team brought us brand new boogie boards for our use, simply bc he's a nice guy who cares about your vacation. I would definitely rent from this company again. I have used other companies and were invariably disappointed, either for something small or big, so I'm happy with Gertrude Rentals.

Review #415 Everything you need, amazing beach location…

5th October 2013

This place is spotless and beautifully decorated. All the furnishings were brand new and very comfortable. You are practically in the ocean at this location, so the location cannot be beat. For this price and comfort, it's steal. Also, during our+ Morestay, Dan and his team brought us brand new boogie boards for our use, simply bc he's a nice guy who cares about your vacation. I would definitely rent from this company again. I have used other companies and were invariably disappointed, either for something small or big, so I'm happy with Gertrude Rentals.

Review #414 Loved it!!!

7th June 2013 by Marti from GA

We had such a great time! The beaches are the best! The condo was very nice. New furnishings and decor but still had that old Florida charm. Everything was easy and uncomplicated. No fuss, just fun and relaxing. Dan and John were very accommodating+ Moreand easy going. They could charge more, but don't tell them I said that!

Eight Steps to path of #1 Beach on Siesta Key! – Old Man and the Sea Inn (B)

Siesta Key, Florida, United States

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Siesta Key, Florida, United States

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(917) 842-9081

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Contact

(917) 842-9081

Property

86 Reviews (4.5)

The location was everything I was looking for, being super close to the beach. Also, the apartment was…

I want to thank Daniel, James and the staff for such a great weekend, the house is amazing, white wine…

Absolutely loved our trip to siesta key and our stay at the old man and the sea inn. Took full advantage…

Wonderful place and location service was top notch. Will look at using Gertrude rentals for future travels….

Our stay was absolutely perfect! Daniel was a wonderful host- we especially loved the wine and crackers…

Review #355

Review #357 Clean, cozy and relaxing…

Review #358 Can’t wait to go back

Review #359 Great location & value

Review #361 Loved it!!!

Review #363 Comfortable and close to the beach.

Review #364 Clean & Close to the Beach

Review #365 Wonderful place to stay just steps from the beach!

Review #366 AMAZING as always!!

Review #367 What a find!

Review #368 Awesome stay!

Review #372 Can’t wait to go back

Review #373 Great location & value

Review #375 Loved it!!!

Review #377 Comfortable and close to the beach.

Review #378 Clean & Close to the Beach

Review #412 Can’t wait to go back

Review #413 Great Location and accomodation

Review #416 Comfortable and close to the beach.

This was our third stay at this property and all three visits have been absolutely wonderful. The location…

Let me start by saying that when I visit Siesta Key there isn’t another place that I will stay. This…

Review #380 Location, location

Review #379 R&R – so relaxing!

Review #381 Lovely Place

Review #382 Perfect Stay

Review #383 CRTESCENT

Review #384 Terrific…Exactly as Advertised

Review #339 Super accommodations; Location, location, location

Review #385 Family vacation

Review #386 Stunning location!

Review #340 8 Steps to Paradise

Review #341 Great time!

Review #387 43748

Review #388 PERFECT Honeymoon!!

Review #389 Great Place!!!

Review #390 Perfect for Us

Review #391 Best vacation ever!

Review #392 Old man and the sea

Review #393 UNIT B

Review #394 Returning Guest

Review #395 Absolutely perfect

Review #342 Even better than last year

Review #338 Great place!

Review #343 Even better than last year

Review #344 Paradise!!

Review #345 Hated to leave!

Review #396 Best vacation EVER

Review #397 Fantastic find – no reason why not to come back!

Review #398 As advertised!

Review #346 Amazing Hospitality!!

Review #399 UNIT B

Review #400 I made a good decision

Review #403 Very Nice!

Review #347 Awesome stay!

Review #404 Great location!

Review #348 amazing

Review #369 Perfect little rental right off the beach

Review #349 Mr. Daniel Jones truly has a Great Place to share!

86 Reviews
(4.5)