A family-friendly stay in the heart of Siesta Key awaits you at this holiday home. Within steps you'll find Siesta Key Beach and Siesta Key Farmers Market within a short 5-minute stroll. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features 3 bathrooms, a balcony and a sofa bed. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a Smart TV and a coffee/tea maker are also available. Limited housekeeping is available. .This pet-friendly holiday home offers a water park, barbecues and a lift. Plus you'll find laundry facilities. .Attractions within a 15-minute drive of this Siesta Key Village holiday home include Sarasota Memorial Hospital and Crescent Beach.
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.) - 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
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
In-room accessibility
Lift
Smoke-free property
Services and conveniences
Iron/ironing board
Limited housekeeping
Location highlights
In a village
In the city centre
Near a hospital
Near a zoo
Near the marina
Near the sea
Things to do
Bicycles
Heated pool
Kayak
Optional golf privileges
Water park
Birdwatching nearby
Cycling nearby
Ecotours nearby
Fishing nearby
Golfing nearby
Kayaking nearby
Motor boating nearby
Parasailing nearby
Sailing nearby
Scuba diving nearby
Snorkelling nearby
Surfing/bodyboarding nearby
Swimming nearby
Theme park nearby
Wildlife walks nearby
Windsurfing nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
Deadbolt lock
General
Bicycles
Policies
Check-in
Check-in time starts at 3:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are welcome
Service animals are exempt from fees.
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector and a deadbolt lock in all accommodation.
Property is also known as
758692
Frequently asked questions
Are there any beaches close to NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?
Yep, NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... is a short 2-minute walk from Siesta Key Beach.
Fun beach activities include snorkelling, scuba diving and windsurfing. You can also find motor boats.
Does NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... have a pool?
NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... has a heated pool and a communal pool.
Does NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... have a waterslide?
No, but it has a waterpark and lazy river.
Is NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... family-friendly?
You bet! With amenities such as a water park and laundry facilities, as well as highchairs and travel cots, it's no surprise that NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... is a winner with our family travellers.
Is there a free airport shuttle available at NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?
No, NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... does not offer an airport shuttle service.
What time are check-in & check-out at NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?
Check-in begins at 3:00 PM. Check-out time is 10:00 AM.
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 45 out of 46 reviews
10 - Excellent
45
Rating 8 - Good. 1 out of 46 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 46 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 46 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 46 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Gina M., Colorado Springs
16 Feb 2026
Liked: Cleanliness
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
10/10 Excellent
Suzy L.
26 Dec 2025
Liked: Cleanliness
Nice house within walking distance of the beach and the town. Host was a good communicator.
Suzy L.
Stayed 3 nights in Dec 2025
10/10 Excellent
tanya t.
13 Nov 2025
tanya t.
Stayed 4 nights in Jul 2025
10/10 Excellent
Diana M.
21 Jul 2025
Liked: Cleanliness
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
10/10 Excellent
Thomas W., New York, New York
4 May 2025
Liked: Cleanliness
Great house and location
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
10/10 Excellent
Emily M.
29 Apr 2025
Liked: Cleanliness
Girls weekend
We do this every year same group same weekend. We wanted to make it special for our 50th birthday celebrations!! (We’ve been friends a long time.) the house was perfect for going to the beach or hanging out in the village. Plenty of rooms greet areas for gathering. (We are between 7-10 women). We’ve stayed in a lot of places this was easy and excellent. Yeah stuff broke or didn’t work right and as soon as I let them know they were right one it. Made it easy. Also the house if well equipped with all the beach things you need.
Emily M.
Stayed 4 nights in Apr 2025
10/10 Excellent
Grant S.
15 Sept 2024
Liked: Cleanliness
PRIME Location!!
The stay was perfect! Great accessories for the beach, walking distance to the restaurants and bars. Beach was a short walk as well! We loved the stay and would recommend it to anyone. The elevator was a cool touch as well it made it easy to fill a cooler and bring luggage to different floors. Really great communication and even let us drop our bags off a bit early which was awesome!!
Grant S.
Stayed 3 nights in Sep 2024
10/10 Excellent
Thomas C.
19 Jul 2024
Liked: Cleanliness
Amazing location and property!
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
10/10 Excellent
Verified traveller
7 Jun 2024
Liked: Cleanliness
Amazing in every way!
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
10/10 Excellent
Pedro L.
24 May 2024
Liked: Cleanliness
Great Location and Clean house
We enjoyed our stay here very much. House was close to restaurants and the beach so we really didn’t have to drive around much. It was also nice to have a wagon to take our stuff to the beach as well as bikes to explore the area. I thought the pool was small but lots of other compensating factors.
Pedro L.
Stayed 4 nights in May 2024
10/10 Excellent
Elaine K.
22 Apr 2024
Liked: Cleanliness
Girls get away
Property was as stated, plenty of room, nice decor, close to everything, lovely pool, the beach accessories were a great touch! Wed
Elaine K.
Stayed 4 nights in Apr 2024
10/10 Excellent
Jen N.
6 Nov 2023
Liked: Cleanliness
Girl’s weekend getaway
This house is outstanding from the beauty of the home to the location of the beach and village attractions. We can’t stop talking about it and are preparing for next year. You will not be disappointed. Everything is right at your fingertips. Siesta Key is amazing.
Jen N.
Stayed 4 nights in Nov 2023
10/10 Excellent
Lisa A.
22 Oct 2023
Liked: Cleanliness
Siesta key birthday weekend
Great house, great location. Had everything we needed. Owner very responsive and easy to work with. Looking forward to staying in the house again.
Lisa A.
Stayed 3 nights in Oct 2023
10/10 Excellent
Nick S.
21 Oct 2023
Liked: Cleanliness
Great Beach getaway
Great location! Walking distance the beach and restaurant's / bars in Siesta Key.
Nick S.
Stayed 4 nights in Oct 2023
10/10 Excellent
Lisa B., Tampa, FL
25 Sept 2023
Liked: Cleanliness
Great girls trip house
We had a great weekend going into the village and then the opposite direction to the beach. Perfect location. We were all comfortable. The only thing I didn’t like is the that the bedroom right next to the pool did not have a complete set of blinds so when your neighbors were using the pool they could see directly into your room. Need to have those fixed but overall great stay. They were very responsive.
Lisa B.
Stayed 3 nights in Sep 2023
10/10 Excellent
Ann M.
17 Sept 2023
Liked: Cleanliness
Couples weekend get a way
The property is outstanding! Very very well appointed! Looked just like the pictures, and they had everything you could ever need! We had one small problem with the Internet, and someone was there quickly to fix it! Outstanding, I would highly recommend this place to anyone looking to go see how beautiful siesta key is with a Group.
Ann M.
Stayed 3 nights in Sep 2023
10/10 Excellent
Ashley E.
6 Sept 2023
Liked: Cleanliness
Perfect siesta key location
Walking distance to the beach with a semi private pool (shared with adjoining unit). All the amenities provided, and more. Elevator to the fourth floor was super convenient. Walking distance to shops and restaurants. Property manager was flexible and easy to work with. Definitely would stay again!
Ashley E.
Stayed 3 nights in Aug 2023
10/10 Excellent
Erin M.
25 Aug 2023
Liked: Cleanliness
Beach vacay
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
10/10 Excellent
Debbie A.
26 Jul 2023
Liked: Cleanliness
Vaca
We had a great time. The villa had many extras bikes, ping pong , great kitchen
Debbie A.
Stayed 3 nights in Jul 2023
10/10 Excellent
Melissa M.
25 Jul 2023
Liked: Cleanliness
Wonderful stay in Siesta
We had the best time! Dan was very responsive, within minutes was answering anything I had questions about. The house was fully equipped with everything you could possibly need for the beach. The elevator made it incredibly easy to bring in all of our luggage and food. The house is beautiful and walking distance to all of the restaurants and bars. It couldn’t have been a better location for us. Thank you for making our trip and stay wonderful!
Melissa M.
Stayed 3 nights in Jul 2023
10/10 Excellent
Carol A.
10 Jul 2023
Liked: Cleanliness
FANTASTIC
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
10/10 Excellent
Verified traveller
28 Jun 2023
Liked: Cleanliness
Quiet and Convenient
Great location within short walking distance to beach and local restaurants.
Verified traveller
Stayed 3 nights in Jun 2023
10/10 Excellent
Katie P.
23 Jun 2023
Liked: Cleanliness
Great vacation home
I highly recommend this property. The place was perfect for our family. The beach is 2 blocks away. Everything was great and I will definitely be back. Dan was great with communication. Everything ran very smoothly.
Katie P.
Stayed 4 nights in Jun 2023
10/10 Excellent
Verified traveller
1 Jun 2023
Liked: Cleanliness
Very close to the beach!
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
10/10 Excellent
Shelley W.
19 May 2023
Liked: Cleanliness
Beautiful place
We loved the proximity of this place to the village & to the beach. It was roomy & clean. The only drawback was that we had a large group of twenty somethings next door that had a hard time keeping down the noise. They were nice but loud.