Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
Las Ventanas Resort-like setting with semi-private pool, rooftop deck, in-house elevator, and 5 terraces in heart of Siesta Village! Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love ∙ Terraces and Rooftop –beautiful views from five balconies and rooftop terrace ∙ Semi-private Pool – heated pool and sun shelves shared with just one other unit ∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear water ∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Village ∙ Gulf Breezes –Ventanas means “Windows” and 3000 ft.² of windows catch sea breezes day and night ∙ Relaxing – 5 baths and a balcony off every bedroom ∙ Sunsets –walk 1-minute to best sunsets or just enjoy from your rooftop deck ∙ Activities – a few free bikes and paddleboards provided, but scooter and golf cart 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 – walk to all Siesta Key's top attractions and guaranteed fun for all
The Beach Our beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.
The Location You aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy a semi private pool (shared with just one other unit), as well as private features including - four private gathering areas for your bonding enjoyment including a poolside swim-out room with wet bar, and a rooftop sundeck with ocean views and wet bar. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.
Bedroom Details This is a huge 4BR, you can sleep up to 13 family style. The master suite (large) has two queen beds with bath en-suite, a twin bed in the alcove and a large terrace. Bedroom #2 has a king bed and terrace. Bedroom #3 has a queen bed with bath en-suite and a terrace. Bedroom #4 is a swimout apt with a queen bed, living room, TV, full bath en suite, and private lanai poolside.
Beach Gear Provided We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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, 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.
Our prices include all fees. No hidden fees.
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Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
Siesta Key Village
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 and a deadlock
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Siesta Key
Located in Siesta Key Village, a neighbourhood 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 Stardust Event Center. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with ecotours and cycling.
St. Boniface Episcopal Church Labyrinth - 3 min drive - 2.4 km
Siesta Key Beach Playground - 3 min drive - 2.1 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 33 min drive
Restaurants
Siesta Beach Pavilion - 3 min drive
Siesta Key Snack Bar - 3 min drive
Circle K - 5 min walk
Gilligan's Island Bar & Grill - 5 min walk
Sun Garden Cafe - 4 min walk
Frequently asked questions
Does Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and 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 | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
As of 15 Apr 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! on 6 Jul 2026 start from £1,039, 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 | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! located?
This family-friendly Siesta Key holiday home is located by the sea, within 1 mi (2 km) of Siesta Key Farmers Market and Siesta Key Beach. St. Boniface Episcopal Church Labyrinth and Irma Beach are also within 2 miles (3 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Great place to stay! The family and I had an awesome week!
Eric M.
Stayed 7 nights in Jan 2026
Response from VrboOwner on 23 Feb 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
The house was in a great spot. Easy to walk to beach, shopping and restaurants.
Susan M.
Stayed 4 nights in Nov 2025
Response from VrboOwner on 5 Dec 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
Amazing location!! Had a beautiful time with friends and family.
Miguelina V.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 16 Nov 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
Gertrude’s Siesta was a perfect gathering place for our crew of adults on an R&R getaway! We loved both the common space and that fact that the bedrooms were located on separate floors affording some privacy. Great property!
Kimberly C.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 16 Nov 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, don't hesitate to reach out and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
John B.
6 Oct 2025
Great
Very nice, roomy house with great accommodations and so close to the beach and restaurants.
John B.
From a partner site
10/10 Excellent
Jorge H.
8 Aug 2025
Siesta trup
Great place to stay. Location was fantastic, a walk to the beach and a walk to Siesta Village. The place had everything one needs. We had a wonderful time. Thank you Dan!!
We had the best family vacation! This location is perfectly situated between the beach and restaurants/bars. We had a great stay!
Melissa R.
Stayed 3 nights in Sep 2024
Response from VrboOwner on 28 Sept 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
Beautiful property with walking distance to all you need.
Renice S.
Stayed 3 nights in Feb 2024
Response from VrboOwner on 9 Mar 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
So glad you had a good time. We hope you come again soon! Just reach out to me "Daniel" at Gertrude Rentals the next time you need anything at all. Repeat guests never pay full price.
We loved our stay here. Host had plenty of beach toys for our family. Great location to beach and town. Would stay here again!
josh r.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 1 Sept 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 stayed a week with a family of 11.We absolutely loved it something for everyone. Close to anything you need within walking distance. Easy in and easy out. Would stay again. Lots of memories.Owner very responsive to anything you might need.
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
From a partner site
10/10 Excellent
Paul S.
23 Feb 2024
Wonderful Stay!
Our girls trip was a success staying in this beautiful home. It's so close to shopping and the beach we didn't need to go far for anything! Love that the pool is heated and we were able to swim in the cooler weather.
Paul S.
From a partner site
10/10 Excellent
Kate B.
30 Jun 2025
Great Times with Great Friends!
Just spent a few days at Ventanas 117 and we had the best time! The house is convenient to the beach and town, and it comes with everything you need. Dan was so communicative and responded very quickly anytime we reached out with questions. We even extended our stay an extra night! Great time!
We had an awesome time and the accommodations were as advertised
Kay P.
Stayed 6 nights in Mar 2024
Response from VrboOwner on 31 Mar 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
The property was great and the location was perfect for us. The property manager was very responsive to every question we had and helped make the trip great. Overall, this was a great place to stay and I would highly recommend it
Jacob K.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 6 Jun 2023
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
This house was perfect for our needs, and everything was excellent. I would definitely choose it again!
Lane & Sherry Z.
Stayed 5 nights in Dec 2022
Response from VrboOwner on 26 Dec 2022
Thank you. We hope you visit again soon. You're a repeat guest now and can call me at (888) 5-SIESTA if you need anything at all! Always happy to help.
From a partner site
10/10 Excellent
Joseph M.
8 Jul 2025
Great
The beach house was very convenient to ocean and village. Dan and Zana were pleasant to work with and very accessible for questions. Property was very clean and well stocked in kitchen, as well as, recreational equipment (wagon, beach chairs, umbrellas, bikes, paddle boards, etc.) Early check-in was very helpful and much appreciated. Our family vacation was fantastic!
Great place. Lots of space and balconies. Loved the layout and pool!
Scott W.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 1 May 2023
Thank you for staying with us. I hope siesta key delivered to you everything you were looking for. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me "Daniel" direct at 8885SIESTA and I’ll take care of you! Repeat guests never pay full price. If it's not too much trouble, please leave us a five star review. It would mean a lot to us.
Thank you for staying with us. We value your business and hope you come again soon! If you ever need anything at all, just reach out to me direct at 8885SIESTA and I’ll take care of you!
Clean, easy to use, management was responsive to our 1 request for additional blankets. Would use again.
Mark S.
Stayed 3 nights in Feb 2024
Response from VrboOwner on 24 Feb 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
From a partner site
10/10 Excellent
Ann B.
1 Sept 2024
Fantastic Siesta Beach Vacation
Had a fantastic stay in siesta key! Walk to the beach, walk to really cute restaurants, restaurants, and bars! House was immaculately set up with space for everyone in our family! Loved the pool and roof deck! Great amenities including beach chairs and umbrellas!! Thank we will be back!!
So many great attributes of this beach rental
- Perfect location between Sunset Beach and the village
- Lots of room for big groups
- Great host with helpful communications
- Check-in and house access were super easy
- Everything you need for the beach
Highly recommend! We would love to stay again
Rebecca B.
Stayed 4 nights in Dec 2023
Response from VrboOwner on 22 Dec 2023
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