Canalfront dog-friendly home with private pool in Siesta Key

A modern living room with a large L-shaped sofa, colorful cushions, coffee tables, and a brick fireplace. Large windows offer a view of an outdoor pool area.
A modern indoor patio with skylights, white walls, lounge chairs, and a small garden area with plants. The space is adjacent to a pool visible through large sliding glass doors.
Bright modern kitchen and dining area featuring a wooden ceiling with exposed beams, large windows, and sliding glass doors leading to an outdoor pool.
A modern kitchen with a terrazzo island, wooden stools, white cabinetry, built-in appliances, open shelving, and large windows. A row of wooden lockers is visible on the right.
A modern bedroom with a striped bedspread, a bedside table with a lamp, a chair, a ceiling fan, and sliding glass doors. The room also features an attached bathroom with tiled walls.
Don't miss out! Price and availability may change

House in Siesta Key, FL

6 guests · 3 bedrooms · 3 baths

Reasons to book

Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
Includes essentials and more

Rooms

Bedroom 1
1 King
Bedroom 2
1 Queen
Bedroom 3
2 Singles

About this house rental

The Windward House

Welcome to your slice of paradise on Siesta Key, where luxury meets comfort in this completely refurbished Mid-Century Modern vacation home just minutes from the stunning beaches. Nestled in a serene neighborhood, this dog-friendly retreat offers a seamless blend of style, functionality, and relaxation.

As you step inside, you're greeted by the timeless allure of terrazzo floors that flow gracefully throughout the open floor plan, enhancing the home's mid-century charm. The attention to detail and abundance of natural light create an inviting ambiance that sets the stage for a memorable stay.

The heart of the home is a harmonious fusion of form and function. In the living room, a cozy fireplace invites you to unwind on a plush sectional sofa, while a large SMART TV stands ready to entertain. The dining room, kitchen, and living area flow together effortlessly, adorned with iconic mid-century modern furniture and clean lines that exude style.

Slide open the ceiling-to-floor glass doors, and you'll step into your own private oasis. The outdoor living space beckons with modern furnishings, a heated pool glistening invitingly, and a courtyard adorned with sun loungers – the perfect spot to soak up the Florida sun. And with direct access to the deep-water canal leading to Sarasota Bay, aquatic adventures are just a stone's throw away.

Back inside, the gourmet kitchen awaits the culinary enthusiast. A large island with stools invites casual dining and conversation, while stainless steel appliances stand ready to bring your culinary creations to life. A kitchen nook boasts a wine cooler, coffee station, and full-size washer and dryer, ensuring convenience at every turn.

Retreat to the primary bedroom through the adjacent office, where a king-size bed adorned with plush linens promises a restful night's sleep. Enjoy direct access to the pool area for a refreshing morning swim or a midnight dip under the stars. The ensuite bathroom boasts a spacious glass walk-in shower and a vanity with two sinks, providing a spa-like experience.

Guests will find their own slice of paradise in the well-appointed bedrooms. A queen-sized bed graces one room, complete with a SMART TV for entertainment. In the second guest bedroom, two twin beds offer flexible sleeping arrangements, also accompanied by a SMART TV. The guest bathroom features a sleek glass walk-in shower, while a convenient half bath is located just down the hall.

Throughout the home, contemporary design elements harmonize with the natural surroundings, creating a seamless transition between indoor and outdoor living spaces. Whether you're seeking relaxation, adventure, or simply a stylish sanctuary to call your own, this Mid-Century Modern haven on Siesta Key promises an unforgettable escape.

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The Beauty of Siesta Key
Siesta Key is a barrier island positioned between the Gulf of Mexico and intracoastal waterway. The powdery white sandy beaches are world renown and stretch over 8 miles along the southwest coast of Florida. Siesta Key is a water-lovers paradise offering crystal clear turquoise water, sailing, fishing, swimming and so much more. Play in the gentle waves and shallow waters, gather unique seashells, or build a sandcastle with your kids or grandkids.

The Siesta Key Village offers a wide selection of shops, cafes, top restaurants, and live music for both its residents and guests. From local oyster bars to waterside dining, Siesta Key has something for every palate. Trolley transportation is available around the island and throughout Sarasota.

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This is a pet friendly home and allows up to 2 dogs. Please include your pet in your booking so we can make the appropriate departure cleaning arrangements. A $250 pet fee is required to help with the departure cleaning to remove pet hair and dander from any furnishings and floors for our future guests. Dogs are not allowed in the pool at any time as the filtration system is not designed for filtering pet hair. Thank you for your understanding and cooperation!

The pool heater is available from October through May at an additional cost of $12 per day for the duration of your stay. If you would like the heater turned on during your stay, please contact us in advance so we can have it ready for you. Thank you and we look forward to hosting you!

Map of Siesta Key, FL


Things to know

Check-in: 4:00 PM
Check-out: 10:00 AM
Early check-ins and late check-out requests will be accommodated upon request and based upon availability. Unauthorized early check-ins and late checkouts will incur a penalty fee.
House rules
  • No parties or events allowed without prior approval, fees apply
  • Must be 25 or older to rent

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All RedAwning properties are professionally cleaned after each stay. In addition, RedAwning includes $3,000 USD of damage waiver coverage in the cleaning fee price in place of traditional damage deposits so you can have a carefree stay.
Booking feeNo booking fees, easy credit card payments.
Service feeThis helps RedAwning provide a safer and more secure booking experience.
TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner RedAwning
  • RedAwning is a trusted partner with over 1 million guests served.
  • Contact RedAwning customer service 24/7 via live chat.
  • No booking fees, with easy credit card payments.

About our partner

This property is managed by RedAwning - a trusted partner that has served over 1 million guests

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7,000+

5-star reviews on TrustPilot

14+

Years of service

15,000+

Vacation rentals across 1,000 destinations

FAQs

Is parking included with this house?

Parking is not specified as an available amenity at The Windward House. 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 The Windward House pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What payment types are supported?

This property accepts Visa, Mastercard, American Express, Discover, and Diners Club. Some card brands may not be accepted if you are located in a country or using a currency they don't support.