Best Value on Siesta Key and Steps to Beach! – The Siesta Key Poor-Boy

36 reviews
Siesta Key, Florida, United States








This is the Poor Boy, a Gertrude Rentals property! This budget accommodation is just 8 steps to the sand path of Siesta Key’s best beach. The Poor-Boy unit is perfect for travellers in search of all the best the island of Siesta Key has to offer but on a limited budget. Tastefully decorated, fully appointed, and immaculately cleaned but with less refined moments than our other units. If you’re looking for a beach lovers paradise and aren’t too fussy to endure – 1) an unglamorous main entrance next to the laundry room, 2) JUST ONE PARKING SPACE, 3) tarnished tiles, 4) Formica counters, 5) mismatched fridge and stove colors, and 6) the possibility you’ll hear the footsteps or conversations from the unit above you then the Poor-Boy is perfect for you. This 2BR/1Bath is offered at a 1BR price, sleeps up to 8, and features a one king BR, one bunk bed BR, and one sleeper sofa.

The Location – Leave the car behind and walk to the top beaches, eco-activities and dining including the highest rated seafood, ice-cream, daiquiris, and Siesta’s only waterfront dining. The closest beach is a cove and boasts the calmest/clearest water on the island. Fifty yards south is a limestone reef with tide pools, colorful marine life, miniature conch, chameleons, “usually” dolphin, and “occasionally” turtle, that is perfect for exploring by foot, snorkeling, fishing, paddle-boarding or kayak.  If you prefer relaxation above activities you can nap on the beach, sit in the ocean, relax on your private patio, swing to sleep in the hammocks, or walk to town for drinks at the Daiquiri Deck, Sniki-Tiki, or Orange Octopus. Each unit has a fully equipped kitchen, there is a gas grill downstairs, and you can find fresh fish at the Village Market or catch your own at the beach nearby. It’ a vacation, sleep with the Poor Boy.

History – The Poor-boy unit is on the Old Man and the Sea Inn unit and its name is based on the boy character that fed unlucky Santiago in the book of the same name as the inn. Formerly used exclusively by vacationing owners of the inn I began offering the unit publicly to accommodate guests with mobility issues and families who couldn’t normally afford Siesta Key, but where desperately in need of a vacation.

Support Post Booking – I understand vacation time is precious and my job is to make sure you get the most out of it.  My number is the only contact information you need. My units are already at the top attractions on the island.  Cars are never required, but if you have one you get a private parking space. Check-in any day of the week at any time using your private door-code.  No requirement ever at checkout.  Free early/late check-in/check-out, whenever possible.  Never hidden fees or solicitations of any kind. No paper contracts and easy booking.   I’ll phone you to touch base after booking and the week vacation starts. Five days before arrival I’ll email instructions including your door-code address and guidebook. One day prior to arrival I’ll send you a “Reminder” email with all the same information.

When you book with me you get a fully accessible and knowledgeable owner/host and reliable advice from a Google approved local expert. I can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, Eco-tourism, family friendly activities, or safe ways to lose your kids when you need a break. For the less extroverted, every booking comes with an unabashed guidebook detailing the property, all my favorite things to do in the area, and never any advertisements or solicitations. This is the only rental offering of its kind on the key.

Terms – *Pets are welcome with the payment of a one time pet fee. *Events or gatherings involving outside vendors or a headcount in excess of the combined occupancy rate are allowed with prior owner approval. A Location Event Fee of $2000 applies to events. A Guest based Event Fee of $23 per event guest in excess of the maximum occupancy applies. Events can only be scheduled by reserving every unit on the given location. *A parent or guardian must accompany guests under the age of 21. *We do not allow cancellations and all reservation payments are non-refundable. 


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36 Reviews

This place was amazing. Great location, close to the beach. He even let us stay a little Longer to be…

16th September 2019 by Justine Dixon
This place was amazing. Great location, close to the beach. He even let us stay a little Longer to be able to shower up and leave for the airport! I will def be staying again! :)

Me encanto todo, había de todo para tener una experiencia encantadora.

12th September 2019 by Jessica Lander
Me encanto todo, había de todo para tener una experiencia encantadora.

Fantastic unit and wonderful accommodations, unbelievable communication with ownership throughout the…

24th August 2019 by Jarrod Kroah
Fantastic unit and wonderful accommodations, unbelievable communication with ownership throughout the stay, perfect in every way.

5 star rating

9th July 2019 by Sahira Lopez

Great location! A little overpriced though, needs some updating. Also very small, the pics make it look…

29th June 2019 by Jazmin Vazquez
Great location! A little overpriced though, needs some updating. Also very small, the pics make it look bigger than it is.

This rental was in the *Best* location – Just steps from the beach. We loved the beach themed deco on…

28th May 2019 by Gail Taylor
This rental was in the *Best* location - Just steps from the beach. We loved the beach themed deco on the property. Great place to hang out in the evenings. We rented the poor boy, which we were advised about the mismatched tiles and appliances,

Review #594 cold but nice

22nd May 2019
This place was very very clean and Daniel sent things to do since it was such a cold week. Even went out and bought a highchair since we had a little one along. Would for sure go there again.

Review #595 Old Man and the Sea and Me

22nd May 2019 by The Kennefick Family from MA
My family recently spent 5 days at the Old Man & the Sea Inn on Siesta Key. We had communicated with Daniel several times before we travelled and were comfortable with all the information we received from him. We really appreciated all the

Review #597 Love Siesta Key!

22nd May 2019
Old Man & the sea Inn on beautiful Siesta Key was everything terrific! The suite was full of Florida charm, spacious and clean! You don't even need your sandals to walk to the beach! We took morning and evening strolls in the area. It is all

Review #598 It’s the location

22nd May 2019 by Scott from Illinois
This was a great value rental on Siesta Key. We cooked all of our meals in. The kitchen is appropriately furnished with appliances and wares and there is a gas grill that got a good workout cooking everything from steak to blackened grouper. Fresh

Review #600 Awesome time!

22nd May 2019 by Sardean from New Jersey
Loved it here. Really is just 1 marlin from the sand! :)

Perfect place to have a nice beach vacation.

1st April 2019 by Jorge Cordero
Perfect place to have a nice beach vacation.

Review #580 Location, Location, Location

13th December 2018 by Melissa Sampson from Siesta Key Poor Bay
The location doesn't get any better. Everything we may have needed was provided in the unit. The wifi went down and the property manager took care of the problem right away. We couldn't be more pleased and will be back!

Review #581 Comfort, Location, & Budge

6th August 2018 by Mayda Cordero from Miami, Fl
What more could we ask for!Loved how clean everything was and that we had sample products for only our use,!It gave me peace of mind that we weren’t using some old dingy sponge!Loved outdoor area and best of all the outdoor showers for rinsing

Review #582 LOVED the Poor Boy

14th June 2018 by Julie Graham from Van Wyck, SC
The Poor Boy was absolutely perfect for our family. The location is truly steps away from the most amazing beach. Itself, the Old Man and the Sea, was a piece of paradise with nice outdoor furniture and the most beautiful landscaping. The kitchen

Review #583 Heaven!

16th April 2018 by Sasha from New York
The Old Man & The Sea Inn is pure charm and reflects the thoughtfulness and passion of the owners to make your experience, no matter what you can afford, a wonderful vacation. Gertrude Rentals has all kinds of rentals from high end to more

Review #584 Sunsets and savings!

29th March 2018 by Amy W from Virginia
My family and I stayed in the poorboy and had an amazing time. The unit itself is a little small and you can definitely hear the upstairs neighbors but that is explained in the descrption so you already know what you are going to get. The honesty

Review #579 Happy Repeat Customers!

12th March 2018 by Matt and Jill from Old Man and The Sea
We returned to this property again this year because the owner Daniel is so easy to work with. He and his staff go out of their way to ensure we have a pleasant stay. Wonderful location just down a beach access to beautiful beach. Love the

Review #585 Paradise!

17th February 2018 by Matt and Jill from Poor Boy in Old Man and the Sea
Easy check in and out! Cute decor! Easy beach access! Private patio and beautiful landscaping! Quiet neighborhood! Daniel so easy to work with and we are going back next week! Loved it!

Review #586 Another fantastic time!

5th December 2017 by Lee Knights from UK
For the 3rd year running, I have booked one of Daniel's amazing properties. This time, it was less than 30 seconds walk from the amazing beach and ocean and within 5 mins drive of everything Siesta Key Village has to offer. The Poor Boy is a home

Review #587 Great Location and Superb customer service

21st August 2017 by Gerdie from Homosassa, FL
We enjoyed our stay in siesta key, The place has Great location, close to beach. The room is clean, the sleeper sofa is old but functional. The common outdoor space and small patio in back are very nice areas. Plenty of beach towels!Daniel is very

Review #588 Siesta Key Poor Boy

9th August 2017 by Diane from Colorado Springs, CO
We stayed 3 nights. The location is wonderful. Steps from the path to the beach. You don't even have to put your sandals on. Daniel was very responsive to our request for another coffee maker because the one in the unit was broken. The bed in the

Review #589 Great Location!

10th April 2017 by Hook Family from Poor Boy
Great location to the beach. We have 3 children and it was nice to be able to walk to the beach and come back and take a nap and then go back to the beach! All the beach stuff was right there. We just grabbed chairs an umbrella and some sand toys

Review #590 Poor Boy

7th April 2017 by Tom from Michigan
Awesome time! Close walk to beach! Clean! Would stay here again!

Review #591 July 4th holiday

16th February 2017 by bob grieco from Atlanta GA
2nd time in this unit, love that is it literally at beach access #13 at Crescent/Siesta beach. all the beach chairs, beach toys etc were used by the kids and love the little common patio area. Will be back in fall or next summer for sure!

Review #592 Had a great time in Siesta Key beach!

13th July 2016 by May L
We had totally 10 people travelling together this time. I really appreciated that Daniel helped me work out our reservations in the last minute. The place is not spaceful but very cozy. You can easily walk to the beach. Daniel sent us the guide book

Review #593 Great Location and Comfortable

22nd July 2014
My family and I recently stayed at this property. It rained a few days but we still made the best of it. The "free" taxi service is awesome to go to the local bars in the evening. We enjoyed grilling out in the "common areas" and smore's in the

Review #596 Perfect beachhouse!

19th March 2014
This beach house was just what we were looking for. Great location right by the beach! You really don't even need to wear shoes when you leave the house to spend some time in the sand. Also so nice that it is close to shopping and some great

Review #599 Clean, zero hassle check-in/out, awesome location!

11th January 2014
I live and work in Sarasota and invited several buddies down to FL from around the U.S. for a weekend of kayak fishing and BBQ. This place was the perfect location for everything we wanted to do. It's off the beaten path with little through traffic

Review #601 Just what our family needed!

30th October 2013 by Andrea from GA
Great location! The beach was absolutely perfect! The condo was fresh and clean, but relaxed, just like the pictures. Plenty of room to get together as a family without being on top of one another. The kids had plenty to do and the grown ups got to

Review #602 Thank you!

5th October 2013 by MCB from Texas
We thoroughly enjoyed our stay here. The furnishings were lovely and clean. The kitchen had everything we needed to feel at home. Beach access was steps away which made it really easy. Dan was really attentive, though we didn't need hm for anything.

Review #603 Paradise!

4th October 2013 by anne1969 from Ohio
I can't wait to go back to Siesta Key and stay here again!!! My family (myself, husband, and two kids) had a fantastic vacation for a week. The children were comfortable and happy, which was a relief, as they pretty much hate everything lol! My

Review #604 Old man of the sea

20th September 2013 by allynn grantham from Rhode Island
We stayed at Old Man of the sea for my sister's wedding. I have a large family of 8. We were very comfortable and both Daniel Jones and his brother John were very attentive. we would definitely stay again!!!

Review #605 Hope to stay with the old man again soon!

21st August 2013 by RMS from Florida
My family and I recently stayed in Unit D at the Old Man & the Sea Inn. The condo is very spacious, clean and tidy and included everything we needed to help make our long weekend a memorable one. Just a few steps from the beach, the kids didn't need

Review #606 Relaxing!

15th July 2013 by Cecilia T from Miami, Florida, United States
We enjoyed our stay at Old Man & the Sea Inn. It was clean, nicely appointed, the pillows were soft, and everything was in working order. The bottle of red wine left in the kitchen to welcome us was also greatly appreciated! The location was

Review #607 Our Poor Boy Stay

10th June 2013 by R&Y from Louisville, KY
Our stay was great for access to all that Siesta Beach Island has to offer. The place was has a full kitchen stocked will all the utensils, dishes and appliances you may need to cook for your family and friends. They even have a full laundry area


Siesta Key, Florida, United States
27.246866 -82.533978

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