House
10.0(20 Reviews)
2 Bedrooms
7 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
AU $244/Night
7 Nights - AU $1,711
Windward, FL Villa Rentals
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Compare Villas, Resorts, & Rentals in Windward
10.0
Villa
10.0(5 Reviews)
3 Bedrooms
6 Guests
- Parking
Pool- Balcony/Terrace
View
AU $266/Night
7 Nights - AU $1,864
Cottage
10.0(2 Reviews)
1 Bedroom
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $427/Night
7 Nights - AU $2,986
House
10.0(19 Reviews)
2 Bedrooms
8 Guests
Private Pool- Parking
- Pool
Ocean View
AU $288/Night
7 Nights - AU $2,014
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
Internet
AU $441/Night
7 Nights - AU $3,086
House
10.0(18 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $776/Night
7 Nights - AU $5,431
Condo
10.0(15 Reviews)
2 Bedrooms
6 Guests
Oceanfront- Parking
- Pool
- Ocean View
AU $548/Night
7 Nights - AU $3,833
Condo
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $261/Night
7 Nights - AU $1,828
Condo
10.0(1 Review)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $475/Night
7 Nights - AU $3,324
Luxury Places to Stay in Windward
Over 1274+ Luxury Places to Stay in or Near Windward
House
3 Bedrooms
7 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
AU $9,317/Night
7 Nights - AU $65,215
AU $7,308/Night
7 Nights - AU $51,156
House
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
AU $4,038/Night
7 Nights - AU $28,268
AU $2,923/Night
7 Nights - AU $20,462
New
House
10.0(4 Reviews)
5 Bedrooms
12 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
AU $2,655/Night
7 Nights - AU $18,587
House
10.0(17 Reviews)
6 Bedrooms
20 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
AU $2,312/Night
7 Nights - AU $16,186
AU $2,061/Night
7 Nights - AU $14,429
New
Condo
3 Bedrooms
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $2,059/Night
7 Nights - AU $14,410
New
Condo
2 Bedrooms
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $2,057/Night
7 Nights - AU $14,400
Top-Rated Villas with a Pool in Windward
Over 818+ Top-Rated Private Villas with a Pool in or Near Windward
Condo
10.0(106 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $587/Night
7 Nights - AU $4,111
Condo
10.0(100 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $385/Night
7 Nights - AU $2,698
House
10.0(98 Reviews)
3 Bedrooms
5 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $253/Night
7 Nights - AU $1,772
Villa
10.0(97 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $330/Night
7 Nights - AU $2,307
House
10.0(93 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $366/Night
7 Nights - AU $2,561
Condo
10.0(85 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $472/Night
7 Nights - AU $3,302
House
10.0(85 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $423/Night
7 Nights - AU $2,963
Condo
10.0(77 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $462/Night
7 Nights - AU $3,236
AU $325/Night
7 Nights - AU $2,277
Pet-Friendly Villas in Windward
Over 448+ Pet-Friendly Private Villas in or Near Windward
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $424/Night
7 Nights - AU $2,972
Villa
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
AU $328/Night
7 Nights - AU $2,299
House
9.2(14 Reviews)
1 Bedroom
- Private Pool
- Oceanfront
- Hot Tub
- Pool
AU $349/Night
7 Nights - AU $2,445
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $237/Night
7 Nights - AU $1,659
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
Spa- Balcony/Terrace
AU $325/Night
7 Nights - AU $2,277
House
9.8(7 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Internet
AU $789/Night
7 Nights - AU $5,522
House
9.4(12 Reviews)
1 Bedroom
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
AU $929/Night
7 Nights - AU $6,506
House
4.0(1 Review)
2 Bedrooms
6 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
AU $559/Night
7 Nights - AU $3,909
House
2 Bedrooms
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
AU $894/Night
7 Nights - AU $6,257
Large Private Villas in Windward
Over 237+ Large Villas in or Near Windward for Groups and Families
AU $126/Night
7 Nights - AU $885
House
10.0(2 Reviews)
3 Bedrooms
10 Guests
- View
- Air Conditioner
- Internet
- Child Friendly
AU $845/Night
7 Nights - AU $5,919
Villa
6.0(1 Review)
1 Bedroom
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $278/Night
7 Nights - AU $1,944
Villa
10.0(15 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $763/Night
7 Nights - AU $5,338
House
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
Pet Friendly
AU $275/Night
7 Nights - AU $1,924
Villa
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Pool
- Spa
- Balcony/Terrace
AU $730/Night
7 Nights - AU $5,112
Villa
10.0(4 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Pool
- Kitchen
- Air Conditioner
AU $597/Night
7 Nights - AU $4,178
Villa
9.6(10 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $733/Night
7 Nights - AU $5,134
Villa
9.4(18 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $399/Night
7 Nights - AU $2,796
Wheelchair Accessible Holiday Homes in Windward
Over 91+ Wheelchair Accessible Villas and Holiday Homes in or Near Windward
Condo
9.4(6 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $396/Night
7 Nights - AU $2,774
House
9.0(1 Review)
1 Bedroom
4 Guests
Private Beach- Parking
- Ocean View
- Balcony/Terrace
AU $248/Night
7 Nights - AU $1,736
Condo
9.6(9 Reviews)
1 Bedroom
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $271/Night
7 Nights - AU $1,895
AU $216/Night
7 Nights - AU $1,513
AU $392/Night
7 Nights - AU $2,741
Condo
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $323/Night
7 Nights - AU $2,260
Cottage
10.0(6 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $1,740/Night
7 Nights - AU $12,178
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $356/Night
7 Nights - AU $2,492
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $322/Night
7 Nights - AU $2,257
Windward Villas, Airbnb and Holiday Homes Under $200
Over 173+ Windward Private Villas, Airbnb and Holiday Homes Under $200
House
9.4(29 Reviews)
2 Bedrooms
7 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $274/Night
7 Nights - AU $1,917
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Internet
AU $122/Night
7 Nights - AU $855
House
8.0(3 Reviews)
1 Bedroom
- Private Pool
- Pool
- Kitchen
- Air Conditioner
AU $239/Night
7 Nights - AU $1,673
Condo
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $157/Night
7 Nights - AU $1,101
House
10.0(1 Review)
1 Bedroom
6 Guests
- Parking
- Pool
- Spa
- Balcony/Terrace
AU $276/Night
7 Nights - AU $1,931
AU $142/Night
7 Nights - AU $998
Condo
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $180/Night
7 Nights - AU $1,261
House
9.8(9 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $250/Night
7 Nights - AU $1,752
Condo
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
AU $247/Night
7 Nights - AU $1,726
Instantly Bookable Villa Rentals in Windward
Over 745+ Instantly Bookable Private Villas in or Near Windward
House
9.6(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $452/Night
7 Nights - AU $3,166
House
9.6(10 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $463/Night
7 Nights - AU $3,238
House
8.8(3 Reviews)
1 Bedroom
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $365/Night
7 Nights - AU $2,555
House
8.4(6 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
AU $452/Night
7 Nights - AU $3,166
Condo
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $385/Night
7 Nights - AU $2,694
Condo
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $723/Night
7 Nights - AU $5,060
Condo
10.0(179 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $682/Night
7 Nights - AU $4,772
Cottage
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
AU $476/Night
7 Nights - AU $3,329
House
10.0(31 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $752/Night
7 Nights - AU $5,265
Book a Last Minute Place to Stay in Windward
About Windward Vacation Rentals
There are more than 1283 incredible getaway rentals that are available in Windward. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windward.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windward, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windward. Places to stay near Windward are 1160.64 ft² on average, with prices averaging AU $553 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windward. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Hotels in Windward and 1087 rentals
- Prices for a holiday home in Windward start at AU $116
- Top rated vacation home in Windward is Gulf Front on a ISLAND, 1 pet, tennis, pickleball,sup,kayak. POOL is CLOSED
- Most popular short term in Windward is Spectacular Sunset Views from this Comfortable Island Villa on Resort A3111B
- Cheapest place to stay in Windward is Cozy condo near beach in Englewood
- Most expensive holiday rental in Windward is Cozy 3 bedroom 2 bathroom house.
Recently Booked Hotels, Resorts, or Rentals in Windward
Frequently Asked Questions About Windward?
What are the top hotels or resorts in Windward?
We provide an array of great vacation destinations in Windward. If you are looking to stay in or around the Windward area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windward:
- Gulf Front on a ISLAND, 1 pet, tennis, pickleball,sup,kayak. POOL is CLOSED
- Ibis Landing Beach House.Directly on the Beach! Don Pedro/Palm Island
- Honeymoon, Anniversary, Kayak, beach retreat; comes with bay dock, kayaks & more
- Waterfront 2BR beach & lagoon retreat. Dock, pool, dog-friendly, tennis
- A Little Slice of Paradise
- Your serene escape - Modern, cozy, and close to the beach.
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- 3 bed/3 bath with Stunning Lakeview from private pool
- Use our kayaks to explore; your boat is in view at our dock; boardwalk to beach
- Our Little Island Dream Home with Ferry Included
How many vacation rentals have private pools in Windward?
We have 468 luxury villas and vacation rentals featuriung a private pool in and near Windward. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Windward is best for families?
Searching for a family-friendly getaway in Windward? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Windward?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 1283 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windward.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cape Haze Rental Villas and Private Getaways in Florida | 56 |
