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

Siesta Key, Florida
$1456 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 13

Max Sleeps

Night 2 nights

Min Stay

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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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided Sofa Bed
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 100+ Mbps (good For 1–2 People Or Up To 6 Devices)
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Heated Pool Shared/communal Pool
  • BATHROOMS

    5 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Towels Provided
  • WORKSPACES

    Desk Desk Chair Office
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Bicycle On Site Birdwatching Nearby Ecotours Nearby Fishing Nearby Golf Privileges Ice Skating Nearby Kayak On Site Kayaking Nearby Parasailing Nearby Sailing Nearby Scuba Diving Nearby Snorkeling Nearby Water Park
  • ENTERTAINMENT

    Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The City Center Near A Hospital Near A Zoo Near Outlet Shopping Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Elevator If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. Smoke-free Property Wheelchair Accessible

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 13

Map Map

School District Rates & Availability

Review Review

  • William C.

    Submitted Feb 16, 2026

    Stayed Feb 3, 2026

    good host good amenities

  • Eric M.

    Submitted Feb 2, 2026

    Stayed Jan 26, 2026

    Great place to stay! The family and I had an awesome week!

  • Eric D.

    Submitted Jan 14, 2026

    Stayed Dec 21, 2025

    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.

  • Susan M.

    Submitted Nov 13, 2025

    Stayed Nov 9, 2025

    The house was in a great spot. Easy to walk to beach, shopping and restaurants.

  • Miguelina V.

    Submitted Oct 28, 2025

    Stayed Oct 24, 2025

    Amazing location!! Had a beautiful time with friends and family.

  • Kimberly C.

    Submitted Oct 24, 2025

    Stayed Oct 21, 2025

    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!

  • John B.

    Submitted Oct 6, 2025

    Stayed Sep 27, 2025

    Very nice, roomy house with great accommodations and so close to the beach and restaurants.

  • Jorge H.

    Submitted Aug 8, 2025

    Stayed Aug 4, 2025

    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!!

  • Jeanine C.

    Submitted Aug 5, 2025

    Stayed Jul 20, 2025

    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.

  • Joseph M.

    Submitted Jul 8, 2025

    Stayed Jun 2, 2025

    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!

  • Kate B.

    Submitted Jun 30, 2025

    Stayed Jun 25, 2025

    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!

  • Cassandra P.

    Submitted Jun 14, 2025

    Stayed Jun 8, 2025

    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.

  • Aaron C.

    Submitted Apr 23, 2025

    Stayed Apr 18, 2025

    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.

  • Mike P.

    Submitted Nov 28, 2024

    Stayed Nov 21, 2024

    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.

  • Melissa R.

    Submitted Sep 14, 2024

    Stayed Sep 11, 2024

    We had the best family vacation! This location is perfectly situated between the beach and restaurants/bars. We had a great stay!

  • Ann B.

    Submitted Sep 1, 2024

    Stayed Dec 31, 1969

    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!!

  • josh r.

    Submitted Aug 26, 2024

    Stayed Aug 16, 2024

    We loved our stay here. Host had plenty of beach toys for our family. Great location to beach and town. Would stay here again!

  • Juan J. L.

    Submitted Aug 17, 2024

    Stayed Aug 9, 2024

    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.

  • Geoffrey M.

    Submitted Aug 6, 2024

    Stayed Jul 28, 2024

    This house has it all! Great space, views from the roof, and location, location, location! Walk 2 block to the beach or 2 blocks to the village. No need for a rental car. Take the Frog Hop everywhere! This is our second time staying at this rental. We will be back.

  • Douglas T.

    Submitted Jun 10, 2024

    Stayed Dec 31, 1969

    The house is beautiful and the location is great. Very short walk to the beach and the village. The house is well maintained and equipped. Any issues you may have will be addressed quickly. Wonderful rental property.

  • Olivia F.

    Submitted Jun 4, 2024

    Stayed May 30, 2024

    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!

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Total

Includes taxes and fees
$1,456+
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