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

Top rated by guests
Sunny tropical pool area in Siesta Key vacation rental near the beach.
Living area spacious and sunny leading to dining.
Rooftop terrace with chaise lounge chairs, outdoor dining for eight with view overlooking the palms.
Heated pool with lounging and sun-shelves (shared).
Pool with view of sunset.
review stars
10Outstanding
(53 Ratings)
"Great place to stay! The family and I had an awesome week! "
Eric M.
Don't miss out! Price and availability may change
10 / 10
Outstanding(53 Ratings)

House in Siesta Beach

13 guests · 4 bedrooms · 5 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 house rental

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.

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

Non-smoking
Pets allowed
Family friendly

Map of Siesta Beach


Ratings and reviews

10 / 10
Outstanding(53 Ratings)
8 / 10Excellent·Feb 2026
good host good amenities
10 / 10Outstanding·Feb 2026
Great place to stay! The family and I had an awesome week!
10 / 10Outstanding·Jan 2026
We had an absolutely wonderful stay at one of the Gertrude Siesta Key rental homes, it was truly perfect for our group of 13. The home was spacious, thoughtfully designed, and incredibly comfortable for a large group traveling together. The multiple floors gave everyone plenty of room and privacy, and the rooftop was a fantastic bonus for relaxing and spending time together. The elevator was a huge help for luggage and for anyone with mobility needs, which made arrival and departure so much easier. We also loved having access to the semi-private pool in the back, it was peaceful and a great spot to unwind after a beach day. The kitchen was very well equipped, making it easy to cook meals for a big group, and having a washer and dryer on site was incredibly convenient during our stay. Everything was clean, well maintained, and clearly set up with guests in mind. What we loved most was the location. The home is just steps from a quieter, less crowded beach, which made our beach time so much more enjoyable. At the same time, it's only a short walk to the village, with great restaurants, bars, and shops nearby, the best of both worlds. A special thank you to Dan as well for being incredibly responsive and helpful in every way, his support made the entire experience seamless and stress free. Overall, this rental exceeded our expectations in every way. We would absolutely stay here again and highly recommend Gertrude Siesta Key to anyone looking for a spacious, comfortable, and perfectly located place to stay.
8 / 10Excellent·Nov 2025
The house was in a great spot. Easy to walk to beach, shopping and restaurants.

$$$$
expedia logo

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

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

What amenities are available at Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.