Gertrude's Siesta | 100% Private, Pool, Terraces, Rooftops, in Siesta Village at best Beach!

Top rated by guests
Large Siesta Key 8BR with 8 terraces, roof-decks, private pool, 1-min walk to beach and Siesta Village.
Sunny tropical private pool and sun shelves.
Rare private tropical pool with alfresco dining and lounging.
Private and just a 1-minute walk to the shopping, dining, and entertainment of the Siesta Village.
Private with two rooftop decks, nestled in the palm tree tops.
review stars
9.8Outstanding
(11 Ratings)
"This home was wonderful!! The owner was extremely responsive and helpful. Spacious, clean, and super cute. The pool, rooftop space, and all the balconies were amazing. You cannot beat the location. Su..."
Laura K.
Don't miss out! Price and availability may change
9.8 / 10
Outstanding(11 Ratings)

Apartment in Siesta Beach

22 guests · 8 bedrooms · 6 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this apartment rental

Las Ventanas 8BR
100% private resort-like setting with pool, rooftop decks, in-house elevators and 10 terraces in heart of Siesta Village! Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Two 4BR units (total 8BR), 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
∙ Rare 100% Private – two units (8BR total) with resort-like amenities reserved for you alone
∙ Terraces and Rooftop –beautiful views from ten balconies and two rooftop terraces
∙ Private Pool – heated pool and sun shelves surrounded by royal palms
∙ 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 – 10 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 is 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 have 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 property is two 4BR units (total 8BR). Each unit is a huge 4BR, you can sleep up to 24 family style. The layout for each for BR is as follows - 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.

Amenities

Free Parking
Air conditioning
Pool
Non-smoking
Pets allowed
TV
Heating
Wheelchair accessible
Coffee/tea maker
Refrigerator
Kitchen
Balcony/Terrace
WiFi/Internet
Hot tub/Jacuzzi
Parking Available
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Patio
Kitchenware
Oven
Stove
Laundry services
Bath or shower
Outdoor Cooking
Sofa bed
Family friendly
Children's high chair
Cribs or cots available
Ironing facilities
Towels
Linens
Dining table
Accessible by elevator
Hairdryer
Fire extinguisher

Map of Siesta Beach

city location on map

Ratings and reviews

9.8 / 10
Outstanding(11 Ratings)
10 / 10Outstanding·Jun 2026
This home was wonderful!! The owner was extremely responsive and helpful. Spacious, clean, and super cute. The pool, rooftop space, and all the balconies were amazing. You cannot beat the location. Super close to the beach and downtown stores/restaurants. Had a lot of helpful gear for the beach. This was an amazing trip! We had three kids who loved the place, especially the pool. Having the elevator was super helpful for our older family members. Would definitely recommend!!!
10 / 10Outstanding·Jun 2026
We rented 2 units side by side for 13 people. we had plenty of room and the accommodations were excellent. The units were in excellent shape with all the amenities you could ask for. Easy walk to the beach and also to downtown. gertrude rental did a very nice job.
10 / 10Outstanding·Mar 2026
What a perfect location for a beach trip! We had 17 people for a family reunion - plenty of space for everyone. Super easy walk to the beach, and everything was included- beach chairs, umbrellas, a beach tent, coolers, and wagons to carry it all in. The pool was fun for the little ones, and we had dinner one night on the rooftop. Easy walking distance to many restaurants and shopping. The only thing I would say is to bring your own bath soap so you don't need to run to the store - the small bar they provide is barely enough for one shower. The house had everything else we needed.
10 / 10Outstanding·Oct 2025
Great house with a fantastic rooftop. Plus you cannot ask for a better location. When you walk out of the house, if you look to your right, you can see the beach and when you look to the left, you can see the market and the restaurants. Everything was within a couple minutes walk distance. Loved it!

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FAQs

Is parking included with this apartment?

Yes, parking is listed as an amenity at Gertrude's Siesta | 100% Private, Pool, Terraces, Rooftops, in Siesta Village at best Beach!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this apartment?

Yes, a swimming pool is available for use at Gertrude's Siesta | 100% Private, Pool, Terraces, Rooftops, in Siesta Village at best Beach!. Enjoy the water!

Is Gertrude's Siesta | 100% Private, Pool, Terraces, Rooftops, in Siesta Village at best Beach! pet friendly?

Yes! This apartment is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Gertrude's Siesta | 100% Private, Pool, Terraces, Rooftops, in Siesta Village at best Beach!?

We found 39 amenities for this rental. This includes free parking, air conditioning, pool, non-smoking, and pets allowed.


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