Entire home

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Family-friendly holiday home in Siesta Key with a water park

Photo gallery for Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Pool
Living area
Outdoor dining
Pool
Pool

Reviews

10 out of 10, Loved by Guests
4 bedrooms5 bathroomsSleeps 13

Popular amenities

  • Parking available
  • Air conditioning
  • Pet-friendly
  • Dryer
  • Washer
  • Outdoor space

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪2 min walk‬
  • Place, Siesta Key Farmers Market
    ‪3 min walk‬
  • Place, Irma Beach
    ‪2 min drive‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪21 min drive‬

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 and 1 Double Sofa Bed

Common Space

1 Single Bed and 1 Double Sofa Bed

5 bathrooms

Bathroom 1

Bathtub or shower · Toilet · Jetted bathtub

Bathroom 2

Bathtub or shower · Toilet

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Balcony
Separate dining area
Dining area

About this property

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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Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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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
Property # 9744818

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. 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.) - 33 min drive

Restaurants

  • ‪Circle K - ‬5 min walk
  • ‪Gilligan's Island Bar & Grill - ‬5 min walk
  • ‪Siesta Key Oyster Bar - ‬4 min walk
  • ‪The Big Tiki Lounge - ‬6 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.

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. Irma Beach and Siesta Key Beach Playground are also within 2 miles (3 km).

Reviews

10

Exceptional

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 41 out of 45 reviews
Rating 8 - Good. 4 out of 45 reviews
Rating 6 - Okay. 0 out of 45 reviews
Rating 4 - Poor. 0 out of 45 reviews
Rating 2 - Terrible. 0 out of 45 reviews

Reviews

8/10 Good

Susan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was in a great spot. Easy to walk to beach, shopping and restaurants.
Stayed 4 nights in Nov 2025

10/10 Excellent

Miguelina V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location!! Had a beautiful time with friends and family.
Stayed 3 nights in Oct 2025

10/10 Excellent

Kimberly C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Oct 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

John B.

Great

Very nice, roomy house with great accommodations and so close to the beach and restaurants.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jorge H.

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!!

10/10 Excellent

Melissa R.

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

Wonderful stay

We had the best family vacation! This location is perfectly situated between the beach and restaurants/bars. We had a great stay!
Stayed 3 nights in Sep 2024

10/10 Excellent

Renice S.

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

Loved our stay!

Beautiful property with walking distance to all you need.
Stayed 3 nights in Feb 2024

10/10 Excellent

josh r.

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

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!
Stayed 3 nights in Aug 2024

10/10 Excellent

Verified traveller

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

Perfect stay

Best location & beautiful property!
Stayed 5 nights in Jan 2023

10/10 Excellent

Cassandra P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 6 nights in Jun 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kate B.

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!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Joseph M.

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!

10/10 Excellent

Deanna O.

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

Beautiful house

Great location
Stayed 3 nights in Jul 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Paul S.

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.

10/10 Excellent

Kay P.

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

Spring Break

We had an awesome time and the accommodations were as advertised
Stayed 6 nights in Mar 2024

10/10 Excellent

Jacob K.

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

Siesta Key Stay

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
Stayed 3 nights in Jun 2023

10/10 Excellent

Lane & Sherry Z.

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

Very Enjoyable Stay

This house was perfect for our needs, and everything was excellent. I would definitely choose it again!
Stayed 5 nights in Dec 2022

10/10 Excellent

Scott W.

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

Palace Pleasure

Great place. Lots of space and balconies. Loved the layout and pool!
Stayed 4 nights in Apr 2023

10/10 Excellent

Mark S.

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

Fabulous location and property

Clean, easy to use, management was responsive to our 1 request for additional blankets. Would use again.
Stayed 3 nights in Feb 2024

10/10 Excellent

Nicole P.

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

Summer fun

Great trip and great home!
Stayed 4 nights in Jun 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ann B.

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!!

10/10 Excellent

Rebecca B.

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

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
Stayed 4 nights in Dec 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Mike P.

Great spot in Siesta Key

We had a great time in Siesta Key and the home was perfect for our family of 10. It was a 2 minute walk to the beach and to the hub of town. Very easy to walk to get some food and taking the kids to the beach. The house was great. Plenty of room for our group. Highly recommend.
Stayed 4 nights in Nov 2024

10/10 Excellent

Andrea Q.

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

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.
Stayed 5 nights in Feb 2024

10/10 Excellent

Bill K.

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

Great Rental

This is a great property to rent. Lots of bedrooms and baths. Everything in great physical shape. Really close to the beach. We'd rent it again in a heart beat.
Stayed 6 nights in Jan 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