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.
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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 and a deadlock
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 and St. Boniface Episcopal Church Labyrinth. Discover the area's water adventures with kayaking and scuba diving nearby, or enjoy the great outdoors with cycling and ecotours.
Siesta Key Beach Playground - 3 min drive - 2.1 km
Crescent Beach - 8 min drive - 5.8 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 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
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 does it cost to stay at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
As of 15 May 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 3 Aug 2026 start from AU$1,418, 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.
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
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The host was amazing. Always very responsive and quick to get us what we needed. The house itself was beautiful. Perfect location.
Gina M.
Stayed 5 nights in Feb 2026
Response from VrboOwner on 16 Mar 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
From a partner site
10/10 Excellent
Christina M.
9 Apr 2026
Perfect Spring Break location!
Perfect for our family and my kids' friends. Close enough to everything we wanted! We could give the teens their freedom at night to enjoy a little of the night life. Just a block from the beach made it the perfect location to also set up for beach days while being able to go back and forth to the house if needed. Dan was great and made sure the Amazon fairy sent us whatever we needed throughout our stay.
Christina M.
Verified
6/10 Okay
Ron B.
31 Mar 2026
Liked: Check-in, communication, location
The kitchen was not stalked well for cooking or grilling out, the pool is shared with the next door neighbors, it is a duplex. Location for beach and shops is perfect, parking is a issue if you have 2 vehicles.
Nice house within walking distance of the beach and the town. Host was a good communicator.
Suzy L.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 16 Jan 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
Wonderful place to stay in many a combinations and things to do
Wonderful place to stay
Sheila K.
Stayed 3 nights in Jan 2023
Response from VrboOwner on 17 Apr 2023
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.
The house is perfectly located by the beach and the main strip, the host was very helpful and accommodating!
Thomas W.
Stayed 3 nights in May 2025
Response from VrboOwner on 24 May 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
Location and amenities of the home were fantastic. Easy check-in and check- out made the vacation great from start to end.
Erin B.
Stayed 5 nights in Mar 2023
Response from VrboOwner on 14 Apr 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.
Thank you for the excellent stay. We really enjoyed your property and would love to come back at some point!
K.L. R.
Stayed 4 nights in Apr 2023
Response from VrboOwner on 22 Apr 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!
We very much enjoyed our stay and management was immediately responsive to our communications.
Amy S.
Stayed 5 nights in Apr 2023
Response from VrboOwner on 16 Apr 2023
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.
Had a great stay. The house was awesome loved being so close to the beach! Perfect rooftop view for the sunset too
Erin M.
Stayed 4 nights in Aug 2023
Response from VrboOwner on 4 Oct 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. - Daniel Jones
Great location within short walking distance to beach and local restaurants.
Verified traveller
Stayed 3 nights in Jun 2023
Response from VrboOwner on 16 July 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!
Had a fantastic time! Beautiful location steps from Gulf and restaurants. Daniel was excellent host and communicated throughout check in and check out process.
Andrew C.
Stayed 4 nights in Dec 2022
Response from VrboOwner on 13 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
Daniel R.
15 Mar 2025
Our spring break rental
Really happy with place it was above and beyond with all it has to offer and team always ready to help with any of your necessities, they handled everything from start to finish this is really is a great place to stay and we definitely will be returning with Dan the man
Daniel R.
From a partner site
10/10 Excellent
Linda W.
7 Dec 2024
Perfect spot
We loved this house and it was at a perfect spot. Once we got there we never had to drive, everything was in walking distance.
Linda W.
Stayed 4 nights in Dec 2024
Response from VrboOwner on 22 Aug 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
Amazing property and location!! We loved it! The parents and recent grads had a blast. Thank you!!
Thomas C.
Stayed 4 nights in Jul 2024
Response from VrboOwner on 27 July 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
My family and I stayed in this beautiful vacation home for memorial weekend and we were beyond satisfied with everything the home offered as well as the attentiveness of the host. My family and I loved how close the beach was and how the house is located right next to Siesta Key Village. We are already planning our next vacation to this lovely home.
Verified traveller
Stayed 2 nights in May 2023
Response from VrboOwner on 2 June 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.
Fantastic property in a perfect location. Within easy walking distance to a (basically) private area of the beach, and a very short walking distance to great restaurants and shopping. The home itself was better than we ever expected. Terraces off of almost every room and a nice pool with fabulous amenities. I can't say enough great things about our stay there. All communication with the property manager was also fabulous and he replied VERY promptly to my questions (which were very minor, but he was always very gracious and quick to respond). Love this place and hope to return!
Diana M.
Stayed 4 nights in Jun 2025
Response from VrboOwner on 16 Aug 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
Easy to check in and communicate. Perfect location, pool, and rooms. We will be back! Appreciate everything!
Verified traveller
Stayed 4 nights in Jun 2024
Response from VrboOwner on 16 June 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
Stacie W.
8 Dec 2025
Fabulous location and home
This is a fantastic Siesta Key location. You are steps from the beach and steps from downtown. There is more than enough room for everyone in your group to spread out and enjoy themselves. We rented both 113 and 117 to have one huge space that sleeps 20+. It was so great for everyone to have their own rooms, and we loved the pool area. The rental even boasts elevators as well which is a huge benefit! Lots and lots of beach chairs in each unit (and nice chairs, not the typical old and rusted ones that you typically encounter in most beach side rentals). Siesta Key is such a great spot for a big group as there is plenty to do for everyone - the beach, shopping, sports bars, great restaurants, tennis/pickle ball, etc... You won't regret booking this rental home and even more so if you bring a big group and get both side by side units!
We loved the property! Perfect amount of space for 2 families with kids! So clean and perfect location. Easy walk for kids to beach and restaurants! We will be back!
Carol A.
Stayed 3 nights in Jul 2023
Response from VrboOwner on 4 Oct 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. - Daniel Jones
From a partner site
10/10 Excellent
Tara O.
6 Dec 2023
Birthday Celebration
4 couples stayed in this beautiful home for a birthday celebration! Fantastic location, well appointed house, comfortable beds. Dan is an amazing host and responds quickly to random questions!
Tara O.
From a partner site
10/10 Excellent
p C.
29 Dec 2023
great stay
Our entire interaction with Dan and the Gertrude team was great. The property was just as pictured, well maintained and extremely well stocked. Bikes, beach chairs, even coolers were provided. Definitely recommend Gertrude's and plan to come back soon.