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NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...

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Pool view outdoor alfresco dining area in Siesta Key vacation rental near the beach.
Las Ventanas - a Gertrude Rentals property!
Amazing for sunbathing!
Shared tropical pool with alfresco dining and lounging.
Rooftop deck just a 1-minute walk to the best beaches in the country.

Reviews

10 out of 10
Exceptional
4 bedrooms3 bathroomsSleeps 13

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly

Rooms & beds

4 bedrooms (sleeps 13)

Bedroom 1

1 King Bed

Bedroom 2

2 Queen Beds

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Common Space

1 Single Bed and 1 Double Sofa Bed

3 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet

Bathroom 5

Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
Dining area

About this property

NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...

NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...
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.

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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

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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 2 min walk - 0.2 km
  • Siesta Key Farmers Market - 3 min walk - 0.3 km
  • Irma Beach - 2 min drive - 1.8 km
  • 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

Frequently asked questions

Is NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?

As of 30 Mar 2026, prices found for a 1-night stay for 2 adults at NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... on 19 May 2026 start from AU$1,711, 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 NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?

On-site parking is available at the property.

What time is check-in at NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?

Check-in begins at 3:00 PM.

What time is check-out at NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION...?

Checkout is at 10:00 AM.

Where is NEW MARCH DATES AVAILABLE! WE HAD A CANCELLATION... 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 45 out of 46 reviews
Rating 8 - Good. 1 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 0 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Gina M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was amazing. Always very responsive and quick to get us what we needed. The house itself was beautiful. Perfect location.
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Suzy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice house within walking distance of the beach and the town. Host was a good communicator.
Stayed 3 nights in Dec 2025
From a partner site

10/10 Excellent

Stacie W.

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!
Verified

10/10 Excellent

Diana M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Jun 2025
From a partner site

10/10 Excellent

Dawn A.

LOVED IT!

There were so many things that we loved about this home. There were 7 of us in our group and we were more than comfortable. We did not need anything but our clothes, food and sunscreen. The location of this property is the best! Walking distance to our favorite restaurants, mini grocery store and shopping. We used the trolley for sightseeing and trying an ice cream shop at Crescent Beach. I was surprised by the fact there were two wagons, beach chairs for everyone (plus more we didn't need) and two umbrellas for the beach. Our grandson loved the pool!
From a partner site

10/10 Excellent

Sandy D.

Great

This is my second time renting with Dan, part of the Gertrude family, and each time my experience is better. They make sure your vacation is perfect and that your family enjoys it to the fullest without worries. If you have any problems or concerns, just call them and they will take care of fixing it so you can continue enjoying your vacation. Dan is an excellent person. He explains everything and is always there if you need him. I have traveled a lot to other places, but with Dan, I feel like my vacation is guaranteed and that it will be 5-star. I recommend it and you will not regret it with the attention from Dan and his team. I also emphasize that the houses are very clean and very beautiful with the decoration. Many thanks to Dan and his team for their attention and dedication to make my vacation unforgettable.
Verified

10/10 Excellent

Thomas W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and location

The house is perfectly located by the beach and the main strip, the host was very helpful and accommodating!
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Emily M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in Apr 2025
From a partner site

10/10 Excellent

Daniel R.

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
From a partner site

10/10 Excellent

Amy S.

Our stay at this stunning gulf-view rental was absolutely perfect! The house offered breathtaking views of the sunset right from the spacious deck, making every evening feel magical. The interior was beautifully decorated, clean, and equipped with everything we needed for a comfortable stay. The location couldn't have been better — just a short walk to the beach, local restaurants, and lively bars. It was so convenient to enjoy a day on the sand and then head out for dinner and drinks without needing to drive. The host was incredibly responsive and thoughtful, ensuring we had everything we needed for an unforgettable getaway. If you're looking for a peaceful retreat with unbeatable views and easy access to local hotspots, this place is a gem. We can't wait to come back!
From a partner site

10/10 Excellent

Gretchen C.

Great place great location

We really loved this home to stay in for five nights. It was a two minute walk to the beach, two minute walk to the village. It was very spacious and clean. Unfortunately We did not have great weather to utilize all the multiple decks and the pool area. There is a great rooftop deck where we were able to see a beautiful sunset. We would definitely stay here again!
From a partner site

10/10 Excellent

Linda W.

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.
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

Grant S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!!
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Thomas C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location and property!

Amazing property and location!! We loved it! The parents and recent grads had a blast. Thank you!!
Stayed 4 nights in Jul 2024
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing in every way!

Easy to check in and communicate. Perfect location, pool, and rooms. We will be back! Appreciate everything!
Stayed 4 nights in Jun 2024
Verified

10/10 Excellent

Pedro L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in May 2024
Verified

10/10 Excellent

Elaine K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 4 nights in Apr 2024
From a partner site

10/10 Excellent

Karen S.

Loved our stay Siesta Key

We were a group of nine women enjoying fun in the sun. Our accommodations were perfect. Communication with Dan was superior. The heated pool was enjoyable. I would not hesitate to stay again. 5 stars 😊
From a partner site

10/10 Excellent

Karen S.

Loved our stay Siesta Key

We were a group of nine women enjoying fun in the sun. Our accommodations were perfect. Communication with Dan was superior. The heated pool was enjoyable. I would not hesitate to stay again. 5 stars 😊
From a partner site

10/10 Excellent

Dede A.

Siesta Key gem

This multilevel duplex was a wonderful place to spend a week at Siesta Key. Thoughtfully appointed and beautifully decorated, not one detail was overlooked! Communication with the owner was answered promptly. The location is perfect for strolling to the Village and to the beach, we barely needed our car. We look forward to returning soon
Stayed 8 nights in Dec 2023
From a partner site

10/10 Excellent

p C.

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.
From a partner site

10/10 Excellent

Tara O.

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!
From a partner site

10/10 Excellent

Tara O.

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!
Verified

10/10 Excellent

Jen N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in Nov 2023
Verified

10/10 Excellent

Lisa A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 3 nights in Oct 2023

About the host

Hosted by Gertrude Rentals 888-5SIESTA

Host profile image
Dan Jones, "owner" Gertrude Rentals
Phone: (888) 5-SIESTA
Email: gertrude.rentals@gmail.com
Website: gertruderentals.com

Languages:

English, French

Premier Host

They consistently provide great experiences for their guests
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