Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!
The Island Time Breathtaking pool at large 100% private Siesta Key home! Spacious, tropical, just 5-min bike or 20-min walk to world famous Siesta Key Beach, and 1-mile to free Island trolley! Elevated deck, balcony, and covered alfresco area. Property includes 3BR unit above and 1BR suite below. Perfect for larger groups. Book a getaway now!
What Guests Love ∙ Private Heated Pool, and stunning marble hard-scape ∙ Balconies tropical balcony, 2nd floor lounging deck, and covered alfresco area ∙ Privacy two units for price of one, includes upstairs 3BR and downstairs 1BR ∙ Beach world famous Siesta Key Beach, 5-min bike or 20-min walk ∙ Restaurants 1-mile to free trolley for all 40 of Siesta s bars and restaurants ∙ Sunsets 20-min walk to best sunsets in America or just enjoy from your pool deck ∙ Activities scooter, bike, boat and kayak rentals nearby ∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ The Memories perfect for large groups, quiet, comfort, access to all top attractions
The Beach Our closest beach is the Siesta Key Public Beach on Beach Rd., just 1-mile away. It s the most lively on the island, but also the widest so plenty of room to sit and relax. What makes this beach amazing is it is the only beach on the island that serves food and drinks. That s right! For the first time since the 1970s, you can get beer, frozen cocktails, gourmet sandwiches and burritos, snacks and more at a Siesta Key beach location! The water at this beach is also shallow clear and calm with white quartz-sand and tide-pools perfect for sleeping drinking or playing.
The Home This listing is a 3BR unit above and 1BR suite below for a total of 4BR. Large and 100% private. Heated pool with stunning marble hard scape. Out-door grilling and dining, tropical balcony, 2nd floor lounging deck and covered alfresco area. Perfect for bigger groups, surrounded by palms, and accessible to all Siesta Key s top attractions.
Property Truths and Limits If any of these limits are not a fit for you, just let us know and we ll find you something a little more laid-back - 1) If you re looking for a party spot this property is not for you. However, if you want a quiet getaway, you found the perfect fit and we would love to host you. 2) The Siesta Woods neighborhood agreement requires the pool and all outdoor areas to close promptly at 9 PM. After 9 PM, please move the party to the nearby beaches, to the village, or just move into your unit. 3) Sorry, no nudity in the pool or the pool area and we follow Sarasota rules for non-nude beaches. 5) The pool gate is portable, but according to state law, must stay in place. Also 6) The unit is advertised as “100% private,” and you will never share the home with other guests. Occasionally—typically about once per week—the pool or landscaping service may stop by for routine maintenance. These visits are quick, limited to exterior or storage spaces, and always completed during daytime hours.
Bedroom Details This listing is a 3BR unit above and 1BR suite below for a total of 4BR. The upper unit has a king bedroom and two queen bedrooms. The ground floor unit is a full apartment with TV, living area, kitchen, bath, separate queen bedroom and a queen sleeper sofa in the living room. This is a large rental with 2 living rooms and 4 dining areas, including interior and exterior. You can sleep up to 12 people.
Property Truths The unit is advertised as “100% private,” and you will never share the home with other guests. Occasionally—typically about once per week—the pool or landscaping service may stop by for routine maintenance. These visits are quick, limited to exterior or storage spaces, and always completed during daytime hours.
Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. If you don t have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn t provide snorkeling gear but this and anything you need can be rented or purchased nearby.
Household Items Provided We provide bedding, kitchen items, private laundry, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.
What to Bring It s a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.
Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We 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(they) need alone time.
Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
About the area
Siesta Key
Located in Siesta Key, this holiday home is near theme parks and near the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Travelling with kids? Consider Mote Marine Laboratory & Aquarium, or check out an event or a game at Ed Smith Stadium. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
St. Boniface Episcopal Church Labyrinth - 15 min walk - 1.3 km
Siesta Key Beach - 20 min walk - 1.7 km
Siesta Key Beach Playground - 20 min walk - 1.7 km
Irma Beach - 2 min drive - 1.8 km
Crescent Beach - 4 min drive - 4.2 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 28 min drive
Restaurants
Siesta Beach Pavilion - 2 min drive
Siesta Key Snack Bar - 2 min drive
Circle K - 4 min drive
Gilligan's Island Bar & Grill - 4 min drive
Sun Garden Cafe - 4 min drive
Frequently asked questions
Does Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
As of 6 April 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! on 28 May 2026 start from NZ$1,100, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Pool & Spa, 100% Private, 5-min bike to Siesta Key Beach, 3-miles to Village! located?
This family-friendly Siesta Key holiday home is located by the sea, within 1 mi (2 km) of St. Boniface Episcopal Church Labyrinth, Irma Beach and Siesta Key Beach Playground. Siesta Key Beach is 1.4 mi (2.3 km) away.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Our family enjoyed this spacious house. Very clean, beautiful heated pool, plenty of beach chairs and toys for kids. Our host was extremely responsive. We would definitely stay here again.
Cindy C.
Stayed 6 nights in Feb 2026
Response from VrboOwner on 16 March 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
The host reached out to us to make sure we had everything we needed, so we knew he was available, but the place was so well appointed and maintained, that we had no need to speak with him. It approached record lows while we were here, so not the beach weekend we were hoping for, but the house was cozy and the company wonderful. Hope to stay here again.
Rhonda S.
Stayed 3 nights in Jan 2026
Response from VrboOwner on 23 February 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
Great location - about 3 mins to the beach by car. Definitely walkable. The property was clean and well maintained. Host communication was great. Would definitely stay here again
Ahmed E.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 16 January 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Our family gathered for Thanksgiving, and we enjoyed this beautiful home for a fun long weekend together. The home was great. Clean, spacious, and perfect for cooking and hanging out. Loved the deck and pool. A close drive to the beach. Responsive host A
Melany W.
Stayed 4 nights in Nov 2025
Response from VrboOwner on 22 December 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Crystal C.
19 August 2025
Great
We had a wonderful stay! How was super clean and accommodating! Great views and host was super responsive!
Crystal C.
From a partner site
2/10 Terrible
Nikhil G.
29 December 2025
⭐️
Bad experience.
The hot tube took hours to heat up.
Grandma's quarters had tiny lizards.
Even with renovation, house felt outdated. No USB outlets.
Nikhil G.
From a partner site
10/10 Excellent
Tara S.
28 July 2025
Perfect again
4th stay with Gertrude, 1st at this property- everything was excellent. The house was perfect- clean, spacious, conveniently located- kids and adults all enjoyed themselves. Will definitely be back.
Tara S.
From a partner site
10/10 Excellent
Gail R. B.
10 October 2025
Wonderful Family Reunion
Seven adults gathered for a family reunion from around the country for 4 days.The house, cleanliness, furnishings and pool were even better than expected. The kitchen was well equipped, although, we only ate breakfast in. Although it wasn't heated, the pool was delightful and easy to access. The location was perfect, one mile to Siesta Key beach and close to shops and a wide variety of restaurants.The Owner was welcoming and extremely helpful and responsive. We highly recommend a stay here. We hope to come back again!
The home was very spacious! Kids loved the pool we spent our time there when not at the beach and we were very satisfied with distance of shops restaurants and beach it was a great experience overall!
Kimberly P.
Stayed 4 nights in May 2025
Response from VrboOwner on 21 June 2025
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
To start Daniel's home was amazing. There was so much space for our family, the rooms and common area were clean and set up so nicely. We were thankful that he allowed us to have our pet with us and that there was a fenced yard. The pool was heated and beautiful the kids loved it so much. The location is perfect distance from the beach and all stores or eatery's in town. We will definitely be staying here again in the future for sure.
Kiana L.
Stayed 3 nights in Jul 2025
Response from VrboOwner on 2 August 2025
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Great stay in Siesta Beach. Enjoyed hanging out in the TV room with other families. Bedrooms were very nice and roomy. Very close to Siesta Beach restaurants which was nice. Property Manager was very responsive. Definitely a great place to stay.
Tracy L.
Stayed 3 nights in Jan 2025
Response from VrboOwner on 16 February 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
My family and I ranging from children to senior citizens enjoyed this home. It was spacious, very clean, and has a great pool! The best thing was the just Daniel. He was very responsive and super nice during all communications. I highly recommend renting this home in the quiet neighborhood very close to the beach.
Brandon P.
Stayed 4 nights in Jun 2025
Response from VrboOwner on 19 July 2025
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
Verified
10/10 Excellent
Margaret
20 July 2024
I absolutely loved this place. We had two adults 5 kids 10-16 it was perfect! Very close to beach, spacious, clean, amenities were great, very up to date, etc 7/2024
Margaret
Stayed 6 nights in Jul 2024
From a partner site
10/10 Excellent
francis R j.
10 March 2025
Fantastic Home
The Home was incredible. It is completely updated and it was exceptionally clean. It is also in a great location. Also, the property managers were fantastic. Easy to reach and followed up during the stay to make sure everything was good. I highly recommend this home.
Very nice property. Plenty of room. Very clean. Good location. Weather was terrible but had a wonderful time with family.
Sharon K.
Stayed 3 nights in Jan 2025
Response from VrboOwner on 25 January 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Robert V.
8 April 2025
Island Time
The home was beautiful, very clean, and well prepared to receive our visit. Gertrude Rentals provided and simple and seamless rental process so we could just relax and enjoy our vacation. Any questions were answered promptly and completely. Thank you!!
Robert V.
From a partner site
10/10 Excellent
Nivvi N.
22 May 2024
Great
The place was excellent to stay and the staff were attentive incase of any questions we had. Everything was perfect with this house. It felt like home away from home, relaxing, all needs well taken care of.
Nivvi N.
From a partner site
10/10 Excellent
Amanda C.
6 November 2024
A wonderful gathering place
We came to Siesta Key for our son's wedding. While not all of our family stayed in the house, many dropped by at various times throughout the long weekend. Plenty of seating space for us all. And we were able to grill out in the yard on our final night together.
Amanda C.
From a partner site
10/10 Excellent
Dirk I.
7 May 2024
HOME AWAY FROM HOME
We so enjoyed our stay. The house was very roomy for all of us and the communication with Gertrude Rentals was excellent. Very clean and well maintained. Love having the BIG backyard for our Handsome Hank to play in. The location was excellent just a short 5-10 minutes to the beach and the Village. Will we stay here again??......Heck YES! 5 STAR RATING.
House was very nice. Pool was 94 degrees everyday but one, the day the pool guy turned on the fountain and waterfall for us. Unfortunately it didn’t come back on the next two days. That seemed to help cool it a little bit. That warm of pool maybe common for this area, I am not sure, but really felt warm to us. 4 usable beach chairs, rusty beach wagon that was not usable. No pool floats or ocean toys. We did leave 2 buggy boards and 5 pool floats for the next people. Location in my opinion you need a car, golf cart or plan on using uber every time you leave. We did find out the last night that the frog bus will take you home for tips. I am not leaving negative review, I am just sharing information I wish we would have know on day one. We were very happy with the layout of the house. We had two families with 5 kids ranging from 15-22 and everyone enjoyed their stay.
Casey m.
Stayed 5 nights in Aug 2025
Response from VrboOwner on 6 September 2025
Thank you for your helpful feedback! We’re glad both families enjoyed the home and layout. We’ll review the pool settings and replace the beach wagon. We appreciate you leaving floats and boogie boards for future guests and would be happy to welcome you back anytime!
We had a wonderful time in this very spacious home. It was very accommodating! We had a total of 8 people in our party (2 families). The beds were very comfortable and the house was super clean! Everything was provided including bedding, towels, etc. There was even plenty of beach chairs and 2 umbrellas which came very much in handy as we went to the beach every day. The family room had plenty of seating for all of us and the 65" TV was great for evening movies (we brought our own Apple TV which we hooked up to the TV so that we could us our own Netflix, etc. streaming services). There was also a deck both on the front and rear of the house which was very popular for our group. The front deck is shaded in the afternoon and therefore became the more popular hang out when waiting to dry off from the beach, etc. We also never ran out of hot water when all of us had to take showers which was amazing to me when factoring in 8 people! The kitchen, dining room and bar seating was also great for mornings while all of us were eating breakfast, drinking our coffee, etc. Please keep in mind that walking to the beach isn't very practical since it is about mile. You can rent a golf cart from one of the local rental places but they were way out of our price range. We chose the very short 3 minute drive to Siesta Key public beach (free parking) which worked out great! Just keep in mind that if you aren't familiar with Siesta Key public beach, it is still a fairly long walk from the parking
Anthony F.
Stayed 6 nights in Aug 2024
Response from VrboOwner on 25 August 2024
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
We loved everything about this place! From the pool and spa/hot tub, to the huge, clean rooms, and bathrooms, to the short drive to the beach, and the beach gear (the chairs, umbrella, and wagon) was a hit! Communication was top-notch and prompt, and we hope to come back soon!