Top Location on Siesta Key! Private Gate into Village! – Gertrudes Village House

52 reviews
Siesta Key, Florida, United States








A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won’t find in other getaways. Our living room, master bedroom and mother in law suite each flow onto private patios for indoor and outdoor dining and relaxation. You can take your time under the brightly colored pagodas on the patios, wander one block on a quiet tropical street to your beach for panoramic views of the gulf to the North-West-and-South, follow a private footpath to the village for the best fresh oysters, fish, tropical drinks, ice cream and entertainment on the island, or just laze in our lush bedding. It’s the only one of it’s kind on the key.Named for our grandmother who traveled the world until age of 91 but always insisted this street on Siesta Key was the place she loved best. Generously decorated with billowing linen drapes and an abundance of handmade rugs, pillows and artwork. which includes W-Hotel pillow-top mattresses, high thread count 100% cotton sheets and plentiful pillows. The nearest beach, appropriately named Sunset Beach by residents and initiated guests alike, has the most picturesque views on the island and the best sunsets on our coast. When I was young, my grandmother would take me there and swim out so far we could barely see her yellow flowered bathing cap! Today, we laze float and wade there in the calm crystal clear gulf water with my children. We usually take a short swim to Sand Dollar Island. Shaped by the tides, this island is a naturally occurring white sand cay popular with dolphins, sand dollars, conch and hermit crabs. *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. A Guest based Event Fee of $23 per 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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52 Reviews

We absolutely love staying in the Village House! This was our second year in a row, and we’re already…

21st July 2019 by Sarah Terry
We absolutely love staying in the Village House! This was our second year in a row, and we’re already planning our third! The house was perfect for the nine of us. The private entrance into the village was a perk! The beach was a short walk away

Perfect location and wonderful home. Especially good for our two young daughters (ages 5 and 2.5) who…

30th June 2019 by Nicole Drezner
Perfect location and wonderful home. Especially good for our two young daughters (ages 5 and 2.5) who were easily able to walk to the beach and into Siesta Key Village to restaurants and shops. We also loved using the outdoor grill. Everything we

Awesome as always! Beautiful house in the most AMAZING location. Daniel is easy to work with. We couldn’t…

25th June 2019 by Brandon Allen
Awesome as always! Beautiful house in the most AMAZING location. Daniel is easy to work with. We couldn't figure out how to turn on outside lights- and he had a guy over within a few hours to help us. Convenient to the beach or to the village- 2

We went to Siesta Key for a graduation and reunion and could not have had a better stay. Our cottage…

5th June 2019 by Stephen Reuss
We went to Siesta Key for a graduation and reunion and could not have had a better stay. Our cottage was in a perfect location. The rooms were clean and spacious with everything we needed to entertain, cook, and relax. We were 2 minutes from the

Review #244 we are not margarita people

22nd May 2019
nice place to area would be alot more fun if we were partiers..that is our fault...few aa meetings in close proximity...beach perfect but not dog was great...people friendly town

Review #245 Top notch vacation spot

22nd May 2019
Very nice 3 bedroom house 200 metres to the the powder-white quiet beach. Small residential street in the front. Out the back gate for commercial street with great bar/restaurants, shops and bike rentals. Ride down the beach on a cooler day on beach

Review #246 Wonderful house, excellent located area, a vacation I will never forget

22nd May 2019
I highly recommend Gertrude's Village House for anyone who values sharing special times with family and friends. Well maintained and very safe property, relaxing accommodations. Daniel, Jon and Walter were wonderful. We appreciate their attentive

Review #247 Perfect host!!

22nd May 2019
We rented Gertrude's House over the Christmas Holiday. The one thing that makes this rental so unique is the service that Daniel gives. The most attentive and accommodating rental we've ever had. The location is great- a short short walk to the

Review #250 Best vacation ever!

22nd May 2019
Had an awesome experience. Dan and Jon were great helps. Close to beach and the beach was great.

Review #251 Great vacation!

22nd May 2019 by Lisa from GA
We stayed at Gertrude's for 4 nights, wish it could have been longer. It was perfect for two families (4 adults, 5 kids). The location is great, just between the beach and town. Safe enough to let the older kids (9-13)roam a little and they loved

Review #253 Daniel Jones and his property management team are truly a pleasure to do business with!!!

22nd May 2019 by leannasfu
We stayed at the Gertrude's Guest House in Siesta Key for 3 nights for a girls weekend. The house is adorable and the location is SO PERFECT!!! You can walk to the beach, and you are just steps away from the strip where the bars and restaurants are.

Review #255 Perfect!

22nd May 2019
My family and I had a wonderful time here. The house is close to everything you need,very cute, and clean!

Review #256 Wow!

22nd May 2019 by HGibbs from AL
What a beautiful house! We stayed in luxury. Plenty of room to spread out, sleep and not trip all over each other. It was located near the Village and the beach. Would definitely stay hear again.

Review #258 Close to Everything, Adorable Decoration – No Sacrifices!

22nd May 2019 by kasiebowden from Los Angeles, California
Wow! This house was perfect! I surprised my mother with a trip to Siesta Key, FL. Finding this house was such a lucky break. Daniel gave great directions for local flavors, restaurants we would enjoy, and we tried them all. We were there for four

I see why the reviews are exceptional for you as a owner very pleasant and accommodating. The property…

16th April 2019 by Paula Baughns
I see why the reviews are exceptional for you as a owner very pleasant and accommodating. The property was cozy clean and gave us everything we needed. The location was every vacationers dream to the left short walk to the beach and to the right the

Phenomenal rental. Very clean, comfortable, great location. Gertrude Rentals are our first pick on Siesta…

14th April 2019 by laura restivo
Phenomenal rental. Very clean, comfortable, great location. Gertrude Rentals are our first pick on Siesta Key. Highly recommend these properties.

Review #213 Perfect Location!

23rd January 2019 by Carly from NY
We had a wonderful stay here over a long weekend! We had everything we needed at the house to relax and unwind. Our favorite part was the fact that we did not need a car at all! The beach was barely a 5-minute walk, and the shops, bars and

Review #214 Great Location!

10th December 2018 by Susan from Chicago, IL
Very cute cottage in a great location. Walking distance to beach, restaurants and shops. Daniel was great to work with. Very responsive. We were a party of 6 adults but I can see how it would be great with kids too.

Review #215 Best Location

26th November 2018 by Mark S. from Tampa
We had the best stay at Gertrude’s Village House for Thanksgiving! It’s a beautiful property steps from the village where all the action is. It’s steps from the beach too. Everything that you need is at the property. Beach chairs, plates, a

Review #216 5***** All The Way Around

21st November 2018 by Kathleen McCoy from Beautiful New England
Great location....great house....great host....can't say enough good thing about this property. Right in the middle of Siesta Key....Daniel is extremely responsive to any needs or wants...highly recommend & would go back in a heart beat.

Review #217 Perfectly Wonderful

24th September 2018 by Natalie Bazemore from Coral Springs, Florid.
This ground floor home was perfect for us. Daniel was a gracious host that thought of everything that we would need to be comfortable. Including his wonderful concierge service suggesting amazing restaurants for us! He really gave us a lot of

Review #218 Great place! Perfect location!

23rd July 2018 by Sarah Terry from Kilmarnock, Virginia
This is the perfect beach house! It had everything my family needed. We had a ton of space with the three beautifully furnished bedrooms and two full bathrooms. Daniel provided everything to get us started. From beach towels and toys, to coffee and

Review #219 Excellent Location

11th June 2018 by Cindy Wadsworth from Gertrude's Village House
We decided last minute to take a trip to our favorite beach, Siesta Key. This house had the perfect location. It was located one street away from the beach and was only a 2 minute walk to the sand. We also love to be close to the village, and this

Review #220 Terrific

31st March 2018 by Tina from Siesta Key
The location was perfect. So close to the beach and the village. Outdoor patios were great. Plenty of bedding, towels (both bath and beach) and beach chairs for everyone. The home is attached to another unit but the cement walls prevented any worry

Review #221 Loved this house!

12th March 2018 by Kathy T from Gertrude’s Village House Siesta Key
We are a family of 7adults and this house worked out so great. The location with a backyard gate to bars and restaurants and beach one block away! We had everything we needed to stay! Great vacation spot! Thank you Daniel!

Review #222 Confortable and excellent beach house

1st March 2018 by Javier from Argentina
House very cozy and in perfect condition. It has all the necessary services for a good stay. We were 10 people and we settled down perfectly. The location is unbeatable, 1 block from the beach walking and bars and restaurants. Daniel is super

Review #224 Relaxing Family Vacation

6th December 2016 by Thomas from Kentucky
We came with the family for Thanksgiving and all of us had a wonderful time. We enjoyed the Beach everyday. We had our Thanksgiving dinner outside on the patio where it was warm and pleasant. We were close to the village where we could shop, walk

Review #225 Perfect Rental

1st December 2016 by Tom S. from Kentucky
We gave our children and their families a week in Gertrude's house for their Christmas presents this year and we couldn't have had a better time! The location was just steps from the beach and shopping and the house was perfect for us. We are

Review #226 Gertrude’s Village House

19th November 2016 by Stephen M. from Altoona, IA
Beautiful accommodations. Location couldn't be better. Love Siesta Key. We'll be back for sure!

Review #227 Great Place to Relax and Recharge

16th November 2016 by Tammie from Florida
G's Village House is just as advertised, which is always a welcome relief when booking online! There's so much room with all the patios that it easily accommodates 8-10 people. Within easy walking distance to everything you want, just as others have

Review #228 Great Stay

12th November 2016 by Phelan from New York
Me and my wife stayed here and we had a wonderful time. The house can accommodate up to 10 people. There are 3 bedrooms (double bunk beds, queen bed, and king bed. The AC system in the house works well and there is a BBQ grill. The location is great

Review #229 Perfect weekend!

7th November 2016 by Alexa Jaksec from Tampa, FL
This is the best location in Siesta Key! I stayed here for my Bachelorette party and could not have had a better time. The house was great, tons of beach chairs and amenities. The property management team does a great job detailing the house and the

Review #230 Amazing stay in Siesta!

25th October 2016 by Chelsea from New Jersey
The location of the house couldn't be better. It's a short walk to the beach, bars/ restaurants, and grocery store. The host was so nice and quickly answered my questions. It made my day when he emailed the day before checkout practically begging us

Review #231 Gertrudes Village House

23rd August 2016 by Jane Weber from Gertrudes Village house
A lovely place to stay, perfect location, great beaches, great location. The only thing I wouldask is if the pots and pans could be replaced. Even to fry an egg was kind of a challenge with those pans:) Loved it we wil come again for sure!

Review #232 Great time!

21st July 2016 by LC from Brooklyn, NY
We had a great time staying here on our girls' trip! It's the perfect location near the beach, bars, and restaurants. The kitchen has everything you need and the house was perfectly clean! The garbage was taken away for us which was convenient. We

Review #233 Magnifique séjour

28th April 2016 by Gaelle from France
Très agréable séjour dans cette petite maison joliment décorée (quoi que un peu sombre) et très confortable, à quelques mètres d'une magnifique plage et des commerces de Siesta Key Beach. Le contact avec Daniel avant et pendant la

Review #223 enjoyable family home

8th March 2016 by Michelle from colorado
Excellent location! 1/2 block from the beach and 1 block from Siesta Village restaurants, etc. The house was very clean and comfortable. We had our 3 grown children (and one child's family) visit us in shifts throughout the week and the home worked

Review #234 Perfect Vacation Rental with a Great Location

19th August 2015 by Blakeley from Jacksonville, FL
We stayed here for a girls weekend and couldn't have been any happier with our choice in a rental home. The house was adorable and very clean, and equipped with everything we needed for our stay. And you couldn't have asked for a better location!

Review #235 Perfect Vacation Rental with a Great Location

19th August 2015 by Blakeley from Jacksonville, FL
We stayed here for a girls weekend and couldn't have been any happier with our choice in a rental home. The house was adorable and very clean, and equipped with everything we needed for our stay. And you couldn't have asked for a better location!

Review #236 Loved the location

11th August 2015 by Marcia from Miami
My family and I stayed this past week and it was very nice. So close and easy to get to the village. The beach was pretty close too. The home was very well kept and the owners were really great about giving us the best information and making sure

Review #237 Great Location

30th June 2015 by Kmbdoh from Ohio
We stayed at Gertrude's Village House for two weeks in June. The location was great. Out the back door, through the gate, and we were on the main street in the village, close to bars and restaurants. The beach is a quick 2 minute walk away. And the

Review #238 “Good choice on Siesta Key”

9th April 2015 by marob11 from Atlanta, Georgia
My husband and I and another couple stayed at Gertrude's for 4 days. It is an excellent location on a lovely street a few minutes walk away to the beautiful white sand beach, and literally a walk through a gate in the backyard to the cute village.

Review #239 “Great location!”

3rd November 2014 by 214vacation from Greenville, West Virginia
The location was perfect being so close to the village which had everything; restaurants and shopping. No pet fees - another plus. Everything was great except the bathrooms and kitchen were small and the TV was not plain. We had 1 steak knife to use

Review #240 Comfortable, good location, and had all the amenities

1st August 2014 by Patrick M
We stayed three nights in this great rental in Siesta Key. The house had plenty of space for 6 adults and 2 kids. The walk to the beach takes a only few minutes. Lots of restaurants and shops are right around the corner. The house had a small but

Review #241 Location, location, location!

14th July 2014 by jlbortot from Castle Rock, Colorado
This little gem is the perfect get-a-way for a family or group of friends. I went with my daughter and her friends for her bachelorette weekend, and the fact that we were walking distance to ALL restaurants and shops was absolutely perfect for our

Review #242 Best of both worlds, beach and night life. Definite favorite of mine!

24th June 2014 by Gina F from Mishawaka, Indiana
First of all, thank you Daniel for taking care of our family on such short notice! This home is beautifully landscaped and well taken care of, everything you could possibly need. I wish our vacation could have lasted longer, this really made us feel

Review #243 Perfect place for a Girls only getaway

5th May 2014 by Heidi from FL
This place has it all for the perfect getaway with your girlfriends! Plenty of room for everyone, the prettiest beach around and the Village has loads of nightlife fun / restaurants right in the backyard (or very short walking distance away). We

Review #248 Great weekend get-a-way!

31st October 2013 by K Rich from FLorida
Excellent location for a weekend get-a-away! Perfect unit for a group to relax and have a great time! Perfect walking distance to beach and bars/restaurant spots!

Review #249 We loved everything about this rental! Wow! location!

31st October 2013 by Julie from Florida
We recently stayed at the Gertrude House for a fun ladies vacation, it was everything and more than we expected! The location is top knotch! Couldnt get closer to the beaches and all the action if you tried! As close as it was it was still quiet,

Review #252 Girls Get away

11th October 2013
I rented this house for a bachelorette weekend party. There were 10 girls staying in the house total. For the sleeping arrangements, it was a little tight because of the large number, but the living space was open and had plenty of room for us. The

Review #254 Perfect and Serene — Highly Recommend

21st September 2013
I'm the kind of person who labors over the internet to find a nice place to stay at a competitive rate. It almost doesn't seem worth it bc it's so much work. But, I'm really pleased to say this property exceeded my expectations and makes me believer

Review #257 Happy

12th August 2013
My family and I enjoyed our stay very much. Everything is in walking distance I was very pleased.


Siesta Key, Florida, United States
27.274645 -82.564879

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