The Windward House Villa Siesta Key Exterior photoThe Windward House Villa Siesta Key Exterior photoThe Windward House Villa Siesta Key Exterior photo
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Check-in
26May2026Select date
Check-out
27May2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

5022 Windward Avenue, Siesta Key, Florida, United States, 34242
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Close to Siesta Key Beach

Holiday Home Features

The Windward House is a holiday home featuring a private entrance, three separate bedrooms, and one bathroom equipped with a hairdryer. It includes a kitchen with a stovetop, refrigerator, dishwasher, and kitchenware, as well as a dining area. The air-conditioned home has a TV, washing machine, tea and coffee maker, and tumble dryer. The unit offers four beds and ironing facilities.

Private Pool Highlight

The standout feature of this holiday home is the inclusion of a private pool.

Dining

Onsite restaurants are available for dining.

Location near Siesta Key

The Windward House is located near Siesta Key Village (4 km), Siesta Key Beach Access 7 (1 km), Siesta Key (2 km), Big Sarasota Pass (2 km), Seaside Vacation Villas (0.5 km), The Gallery on Siesta Key (2 km), and Shell Beach (2 km). Sarasota Bradenton International Airport is 20 km away.

Amenities

Amenities include air conditioning, heating, tea and coffee facilities, a dining table, a washing machine, a dryer and cookware/kitchen utensils.

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Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
Three-Bedroom Holiday Home
2 persons
1705 sq. feet 
2 Single beds or 1 Queen-size bed
Private pool
Air conditioning

Calendar of room availability and rates

See current availability and pricing for your dates

Facilities

Amenities are designed to ensure comfort and memorable stays

General

  • No smoking on site
  • Wi-Fi
  • Parking
  • Concierge desk
  • Pets allowed
  • Smoke detectors
  • Fire extinguishers

Sports & Fitness

  • Wind surfing
  • Diving
  • Snorkelling
  • Skiing
  • Horseback riding
  • Cycling
  • Golf course
  • Fishing

Guest Parking

  • Electric kettle
  • Dryer
  • Cookware/ Kitchen utensils

Dining

  • Outdoor dining area

Spa & Leisure

  • Heated swimming pool
  • Outdoor swimming pool
  • Beach access
  • Sun loungers
  • Garden area
  • BBQ facilities
  • Spa & wellness centre

Room features

  • Air conditioning
  • Heating
  • Tea and coffee facilities
  • Dining table
  • Ironing facilities

Bathroom

  • Washing machine

Self-catering

  • Electric kettle
  • Dryer
  • Cookware/ Kitchen utensils
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The Windward House Villa Location

5022 Windward Avenue, Siesta Key, Florida, United States, 34242
Map view
5022 Windward Avenue, Siesta Key, Florida, United States, 34242
Restaurants
The Old Salty Dog Siesta Key
1.0 mi
5023 Ocean Boulevard
Curly Cream
1.1 mi
5053 Ocean Blvd
The Seafood Joint
1.2 mi
217 Avenida Madera
Village Cafe
1.1 mi
5133 Ocean Boulevard
Star Thai and Sushi
1.2 mi
203 Avenida Madera
Lido Key Tiki Bar ?
1.5 mi
Restaurant
The Cottage
1.2 mi
153 Avenida Messina
Lobster Pot Restaurant
1.2 mi
5157 Ocean Boulevard
Island House Tap & Grill
1.1 mi
5110 Ocean Boulevard
Meaney's Mini Donuts
1.2 mi
201 Canal Rd Siesta Key
Explore Siesta Key
Experience Siesta Key
Top Attractions
Activities
Dining
Entertainment
Sarasota Beach
15 minutes' walk
A stunning beachfront ideal for relaxation and swimming with soft sands and clear waters, perfect for family outings.
The Gallery on Siesta Key
The Gallery on Siesta Key
20 minutes' walk
A charming spot showcasing local artisan crafts and artworks; visitors can often find unique souvenirs and gifts.
Siesta Key Beach Access #10
45 minutes' walk
This access point leads to one of Siesta Key's finest beaches, known for its powdery sand and vibrant sunset views.
St. Boniface Episcopal Church Labyrinth
St. Boniface Episcopal Church Labyrinth
20 minutes' walk
A serene outdoor labyrinth providing a peaceful setting for reflection and meditation amidst beautiful landscapes.
Kayaking at Siesta Key Marina
10 minutes' drive
Kayak rentals available for exploring the scenic waters; perfect for adventure seekers and nature lovers alike.
Wellness Yoga at Lido Key
10 minutes' drive
Relaxation-focused yoga classes offered at nearby studios, great for a restorative experience amidst your vacation.
The Old Salty Dog Siesta Key
The Old Salty Dog Siesta Key
20 minutes' walk
Casual waterfront eatery known for its seafood dishes like the crab cakes and a vibrant atmosphere; outdoor seating is available.
Village Cafe
Village Cafe
20 minutes' walk
Cozy café with an array of breakfast and lunch options; famous for their pancakes and brunch specials, vegetarian-friendly.
Siesta Key Beach Club
25 minutes' walk
A lively venue hosting live music and events; a great spot for guests looking to enjoy nightlife and local bands.
Shell Beach
Shell Beach
25 minutes' walk
A family-friendly beach known for its calm waters; great for sunset strolls and shell collecting, providing evening entertainment.
Local transportation
City Centre
Siesta Key12 min  ·  3300 ft
Airports
Sarasota Bradenton International (SRQ)26 min  ·  10.6 mi
St. Pete-Clearwater International (PIE)130 min  ·  53.7 mi
Bus
Bus stop5 min  ·  1400 ft
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Property information and rules
Check-in
from 16:00-23:59
Check-out
until 10 am
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in for free.
Pets
Pets are allowed on request.

Guest ratings and reviews

Guest feedback from past stays
Guest reviews
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FAQs
About The Windward House
What is the check-in and check-out policy at The Windward House?
Check-in is at 16:00 and check-out is by 10:00.
How far is The Windward House from Sarasota Bradenton International Airport?
The hotel is 16 km away from Sarasota Bradenton International Airport.
Is there a swimming pool at The Windward House?
Guests can enjoy an outdoor swimming pool at the hotel.
What room amenities are offered at The Windward House?
Rooms are equipped with air conditioning, a fully furnished kitchen, a multi-channel TV, and a private entrance.
Which nearby restaurants can guests visit from The Windward House?
Nearby restaurants include The Seafood Joint, The Cottage, and Sun Garden Cafe, all located 2 km away.
What recreational activities are available at The Windward House?
Guests can enjoy cycling, skiing, horseback riding, and access to the beach.
Is free parking available at The Windward House?
Free private parking is available on-site without reservation.
What are the nearby attractions to visit from The Windward House?
Attractions include Siesta Beach Pavilion (approximately 4 km) and the family-friendly Mote Marine Laboratory Aquarium (around 12 km).
Does The Windward House provide internet access?
Free Wi-Fi is available for all guests.

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Rooms and Guests2 Guests, 1 Room