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 5 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. In-room jetted baths, a living room and a dining area are also 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.) - 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
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
Location highlights
In a village
In the city centre
Near a hospital
Near a zoo
Near an outlet shopping centre
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
Ice skating 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
758693
Frequently asked questions
Are there any beaches close to Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
Yep, Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! 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 Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! have a pool?
Take your pick from a heated pool, a pool and a communal pool.
Does Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! have a waterslide?
No, but it has a waterpark and lazy river.
What luxury perks are available at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
This property features a heated pool, as well as a jetted bath and a living room.
Is Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! 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 Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! is a winner with our family travellers.
Is there a private hot tub at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
No, but there is Jetted Baths.
Is there a free airport shuttle available at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
No, Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village! does not offer an airport shuttle service.
What time are check-in & check-out at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?
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
9.8
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. 44 out of 49 reviews
10 - Excellent
44
Rating 8 - Good. 5 out of 49 reviews
8 - Good
5
Rating 6 - Okay. 0 out of 49 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 49 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 49 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
8/10 Good
William C.
16 Feb 2026
Liked: Cleanliness
good host good amenities
William C.
Stayed 13 nights in Feb 2026
10/10 Excellent
Eric M.
2 Feb 2026
Liked: Cleanliness
Great place to stay! The family and I had an awesome week!
Eric M.
Stayed 7 nights in Jan 2026
8/10 Good
Susan M.
13 Nov 2025
Liked: Cleanliness
The house was in a great spot. Easy to walk to beach, shopping and restaurants.
Susan M.
Stayed 4 nights in Nov 2025
10/10 Excellent
Miguelina V., Miami, FL
28 Oct 2025
Liked: Cleanliness
Amazing location!! Had a beautiful time with friends and family.
Miguelina V.
Stayed 3 nights in Oct 2025
10/10 Excellent
Kimberly C.
24 Oct 2025
Liked: Cleanliness
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
10/10 Excellent
Jeanine C.
5 Aug 2025
Liked: Cleanliness
Perfect family location for a Siesta Key Wedding
Our five-night stay at Gertrude's Siesta provided the perfect balance of convenience and relaxation as we celebrated our daughter's wedding on SK Beach. The property offered ample space for our nine family members, who ranged in age from 26-86. The elevator provided safe and easy access to the four floors, particularly when moving luggage and items for the reception. Communication and coordination with the owner and local manager was outstanding, particularly when additional household items were needed, e.g., bath towels, dish towels, hot pads, kitchen faucet required replacement, and floors needed to be cleaned. All requests were handled quickly and satisfactorily! We enjoyed the close proximity to the beach and local shops and restaurants. We appreciated the beach extras in the garage, especially the wagons! We thoroughly enjoyed our stay and look forward to staying again.
Jeanine C.
Stayed 5 nights in Jul 2025
10/10 Excellent
Cassandra P.
14 June 2025
Liked: Cleanliness
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.
Cassandra P.
Stayed 6 nights in Jun 2025
10/10 Excellent
Aaron C., Scituate, Massachusetts
23 Apr 2025
Liked: Cleanliness
Great house, perfect location
House is equidistant from the beach and the major retail area in Siesta Key - about a block and a half each way. Perfect spot for our two families with four teenage boys. The kids could walk to the beach or go out to dinner on their own and we got some much appreciated adult time. The house itself was beautiful and clean. Tons of chairs and towels for the beach and wagons to haul them in. Four bicycles, a couple paddleboards - really all you need for a great beach vacation. Plenty of room in the house for 8 of us. The pool and outdoor space were ample and everything was in nice shape. Hosts were friendly and responsive.Thumbs up overall - would definitely stay here again.
Aaron C.
Stayed 4 nights in Apr 2025
10/10 Excellent
Melissa R.
14 Sept 2024
Liked: Cleanliness
Wonderful stay
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
10/10 Excellent
josh r.
26 Aug 2024
Liked: Cleanliness
Great place!!
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
8/10 Good
Juan J. L.
17 Aug 2024
Liked: Cleanliness
Siesta vacation
Great location however small pool that is shared with another property with no privacy is a huge con of this proper, also need more attention to cleanliness of pool. If you dont need a pool location is great between beach and Siesta village.
Juan J. L.
Stayed 3 nights in Aug 2024
10/10 Excellent
Olivia F.
4 June 2024
Liked: Cleanliness
One of a kind!
What can’t I say about this place! This place was absolutely amazing. We had 14 ladies sleeping comfortably, with also plenty of space to shower and get ready. We were amazed at the number of areas and balconies to spend time and relax on! It is walking distance to so many places (coffee, restaurants, bars, beach, grocery store & shopping)! It was a quick 25 minute drive from Sarasota airport, after that no car would be needed. The area was very clean and safe to walk around as well! Dan was also amazing, very easy to communicate with. We didn’t have to worry about stripping the beds/linens, washing towels or cleaning up (not many places you can rent do that). It made our last day so much more enjoyable to relax and hangout at the pool and beach! We are already taking about coming back. Thanks again!
Olivia F.
Stayed 4 nights in May 2024
8/10 Good
sharon g.
22 Apr 2024
Liked: Cleanliness
Girls trip
50+ age, ladies celebrating upcoming wedding for bride to be.
Plenty of room for 9 women.
Its a duplex, neighbors were very nice. Parking spot if rent car. VRBO contact very responsive. Perfect location for walk to town and beach.
sharon g.
Stayed 5 nights in Apr 2024
10/10 Excellent
Brenda B.
14 Apr 2024
Liked: Cleanliness
Amazing
11 ladies for a Girls weekend. Everyone loved this place it was close to EVERYTHING! We all had beds to sleep in. Dan and is staff were so helpful. And nothing better than checking out and not have to worry about a thing. Thanks Dan
Brenda B.
Stayed 3 nights in Apr 2024
10/10 Excellent
Kay P.
30 Mar 2024
Liked: Cleanliness
Spring Break
We had an awesome time and the accommodations were as advertised
Kay P.
Stayed 6 nights in Mar 2024
10/10 Excellent
Andrea Q.
4 Mar 2024
Liked: Cleanliness
Family Vacation
The property was wonderful. The house is large and accomodates many people. The beach and Village were nice and close. I would highly recommend this property for a large group and would utilize again if available.
Andrea Q.
Stayed 5 nights in Feb 2024
10/10 Excellent
Renice S.
4 Mar 2024
Liked: Cleanliness
Loved our stay!
Beautiful property with walking distance to all you need.
Renice S.
Stayed 3 nights in Feb 2024
10/10 Excellent
Mark S.
11 Feb 2024
Liked: Cleanliness
Fabulous location and property
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
10/10 Excellent
Chris M.
15 Jan 2024
Liked: Cleanliness
Nice spot, nice place
Great comms from the host and the house was lovely overall. We would stay again.
There were a few things that we might have expected to be provided (e.g. shampoo) that were not but that was probably an oversight on our part in the listing. Cleanliness could be improved a tiny bit in the bathrooms and the quality of the soaps (given the impressive nature of the place) was a bit disappointing.
But it's a beautiful spot, host communication was superb, the bikes etc. in the garages are great and everything worked very nicely.
Chris M.
Stayed 4 nights in Jan 2024
8/10 Good
Tawnya W.
6 Jan 2024
Liked: Cleanliness
Lots of Space!
This home is beautiful with a great location! We went with 12 in our group ranging from 1 year old to 73, enough space for all for sure but everything is on a different level of the home so you use alot of stairs. There is an elevator but was not working the entire week we stayed so that was a problem with a toddler and grandparents. The beach is beautiful & a short walk! Located within walking distance to many different restaurants and shopping as well. The beds my family of 5 used were OK. The host was responsive & easy to get in touch with.
Tawnya W.
Stayed 7 nights in Dec 2023
10/10 Excellent
Rebecca B.
21 Dec 2023
Liked: Cleanliness
Great family beach vacation
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
10/10 Excellent
Carol F.
29 Oct 2023
Liked: Cleanliness
Very helpful
Dan really helped us by letting us check into the property a little early in order to accommodate our grandchildren with special needs. We are so grateful!
Lovely property in a great location.
Carol F.
Stayed 3 nights in Oct 2023
10/10 Excellent
Lauri H.
17 Sept 2023
Liked: Cleanliness
Awesome Location
Had a bachelorette event consisting of 12 girls. The house was perfect for sleeping arrangements and everyone able to be in one location in the living room. Elevator was working upon check-in, called “Dan”, within 5 minutes he had the technician there to fix it. Such great customer service. Exceptional communication. The location was perfect! Walked to town (great little town). Walked to the beach. Everything you would need for beach trip was there. Everyone loved it!!! Would definitely go back and would book through Gertrude Rentals with Dan!