1168+ Rental Villas and Private Getaways in Windward |
Windward Villa Rentals
New
- Port Charlotte - Charlotte Harbor
- Pebble Beach
- 0.44 mi to center
2000 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $780/Night
For 7 Nights US $5,463
10.0
Exceptional
(5 Reviews)
2002.09 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Pool
- Ocean View
- Balcony/Terrace
US $186/Night
For 7 Nights US $1,302
10.0
Exceptional
(2 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.34 mi to center
1 Bedroom
1 Bathroom
Ocean View
Cottage
- Fireplace/Heating
- Pool
- Ocean View
US $298/Night
For 7 Nights US $2,086
New
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.40 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $746/Night
For 7 Nights US $5,222
10.0
Exceptional
(3 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.45 mi to center
1711.46 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Pool
- Pet Friendly
- Parking
US $273/Night
For 7 Nights US $1,911
New
- Port Charlotte - Charlotte Harbor
- Pine Valley
- 0.50 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Villa
- Fireplace/Heating
- Air Conditioner
- Internet
US $528/Night
For 7 Nights US $3,698
New
- Port Charlotte - Charlotte Harbor
- Pine Valley
- 0.49 mi to center
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $447/Night
For 7 Nights US $3,129
New
- Port Charlotte - Charlotte Harbor
- Placida
- 3.93 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $392/Night
For 7 Nights US $2,742
New
- Port Charlotte - Charlotte Harbor
- White Marsh
- 0.42 mi to center
7 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $360/Night
For 7 Nights US $2,522
Luxury Places to Stay in Windward
Over 1159+ Luxury Places to Stay in or Near Windward
New
- Port Charlotte - Charlotte Harbor
- Palm Island
- 1.06 mi to center
12 Guests
5 Bedrooms
6 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,649/Night
For 7 Nights US $11,540
10.0
Exceptional
(2 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 1.10 mi to center
12 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,608/Night
For 7 Nights US $11,255
New
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.45 mi to center
1700.7 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Oceanfront
- Fireplace/Heating
- Pool
US $1,563/Night
For 7 Nights US $10,944
New
10763.91 ft²
12 Guests
5 Bedrooms
6 Bathrooms
House
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,440/Night
For 7 Nights US $10,080
New
- Port Charlotte - Charlotte Harbor
- Pebble Beach
- 0.29 mi to center
9 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Pet Friendly
- Air Conditioner
- Internet
US $1,344/Night
For 7 Nights US $9,408
New
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.73 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $1,285/Night
For 7 Nights US $8,993
New
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.78 mi to center
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $1,231/Night
For 7 Nights US $8,616
New
- Port Charlotte - Charlotte Harbor
- Rotonda West
- 1.53 mi to center
975 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,151/Night
For 7 Nights US $8,055
10.0
Exceptional
(3 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.99 mi to center
2500 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,108/Night
For 7 Nights US $7,754
Top-Rated Villas with a Pool in Windward
Over 774+ Top-Rated Private Villas with a Pool in or Near Windward
10.0
Exceptional
(110 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.14 mi to center
1702 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $441/Night
For 7 Nights US $3,090
10.0
Exceptional
(109 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.46 mi to center
980 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $361/Night
For 7 Nights US $2,529
10.0
Exceptional
(100 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.23 mi to center
900 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $383/Night
For 7 Nights US $2,679
10.0
Exceptional
(100 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 0.51 mi to center
1138 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $243/Night
For 7 Nights US $1,699
10.0
Exceptional
(92 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.16 mi to center
1748 ft²
5 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $181/Night
For 7 Nights US $1,266
10.0
Exceptional
(91 Reviews)
- Port Charlotte - Charlotte Harbor
- Pine Valley
- 0.57 mi to center
2044 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Fireplace/Heating
US $256/Night
For 7 Nights US $1,790
10.0
Exceptional
(85 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.45 mi to center
980 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $303/Night
For 7 Nights US $2,124
10.0
Exceptional
(85 Reviews)
- Port Charlotte - Charlotte Harbor
- White Marsh
- 0.15 mi to center
1800 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $211/Night
For 7 Nights US $1,477
10.0
Exceptional
(80 Reviews)
- Port Charlotte - Charlotte Harbor
- Pine Valley
- 0.32 mi to center
2200 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $265/Night
For 7 Nights US $1,852
Pet-Friendly Villas in Windward
Over 394+ Pet-Friendly Private Villas in or Near Windward
New
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.28 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $183/Night
For 7 Nights US $1,280
10.0
Exceptional
(3 Reviews)
1345.49 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
US $235/Night
For 7 Nights US $1,645
9.2
Exceptional
(14 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.49 mi to center
1 Bedroom
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $244/Night
For 7 Nights US $1,708
10.0
Exceptional
(164 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 1.27 mi to center
1350 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Ocean View
US $455/Night
For 7 Nights US $3,185
10.0
Exceptional
(2 Reviews)
812.67 ft²
10 Guests
3 Bedrooms
2 Bathrooms
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $192/Night
For 7 Nights US $1,344
10.0
Exceptional
(157 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 1.27 mi to center
1150 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $477/Night
For 7 Nights US $3,342
10.0
Exceptional
(69 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.38 mi to center
900 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $344/Night
For 7 Nights US $2,407
10.0
Exceptional
(64 Reviews)
- Port Charlotte - Charlotte Harbor
- Englewood
- 7.02 mi to center
768 ft²
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $153/Night
For 7 Nights US $1,070
10.0
Exceptional
(55 Reviews)
- Port Charlotte - Charlotte Harbor
- Englewood
- 7.02 mi to center
768 ft²
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $153/Night
For 7 Nights US $1,070
Large Private Villas in Windward
Over 233+ Large Villas in or Near Windward for Groups and Families
10.0
Exceptional
(13 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.18 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $491/Night
For 7 Nights US $3,434
10.0
Exceptional
(1 Review)
2152.78 ft²
10 Guests
1 Bedroom
2 Bathrooms
House
- Private Beach
- Oceanfront
- Fireplace/Heating
US $280/Night
For 7 Nights US $1,960
6.0
Good
(1 Review)
- Port Charlotte - Charlotte Harbor
- Englewood
- 7.06 mi to center
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Fireplace/Heating
- Ocean View
US $194/Night
For 7 Nights US $1,358
10.0
Exceptional
(3 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.49 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
US $496/Night
For 7 Nights US $3,473
9.6
Exceptional
(10 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.54 mi to center
1345.49 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
US $193/Night
For 7 Nights US $1,350
10.0
Exceptional
(1 Review)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 1.25 mi to center
1350 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $689/Night
For 7 Nights US $4,825
10.0
Exceptional
(1 Review)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.40 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $414/Night
For 7 Nights US $2,901
9.8
Exceptional
(42 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.27 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $377/Night
For 7 Nights US $2,642
9.6
Exceptional
(125 Reviews)
- Port Charlotte - Charlotte Harbor
- Palm Island
- 0.27 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $491/Night
For 7 Nights US $3,434
Wheelchair Accessible Holiday Homes in Windward
Over 94+ Wheelchair Accessible Villas and Holiday Homes in or Near Windward
10.0
Exceptional
(22 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 1.83 mi to center
1200 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $338/Night
For 7 Nights US $2,367
9.6
Exceptional
(7 Reviews)
- Port Charlotte - Charlotte Harbor
- Rotonda Heights
- 0.20 mi to center
1334.72 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $223/Night
For 7 Nights US $1,561
10.0
Exceptional
(12 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.20 mi to center
1111 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $470/Night
For 7 Nights US $3,291
9.4
Exceptional
(5 Reviews)
- Port Charlotte - Charlotte Harbor
- Pebble Beach
- 0.33 mi to center
1711.46 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $303/Night
For 7 Nights US $2,123
10.0
Exceptional
(9 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.38 mi to center
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $144/Night
For 7 Nights US $1,006
10.0
Exceptional
(4 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.18 mi to center
1700 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $254/Night
For 7 Nights US $1,775
10.0
Exceptional
(4 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 5.22 mi to center
750 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $172/Night
For 7 Nights US $1,205
9.8
Exceptional
(73 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 0.62 mi to center
1138 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $237/Night
For 7 Nights US $1,659
9.8
Exceptional
(25 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.57 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $354/Night
For 7 Nights US $2,478
Windward Villas, Airbnb and Holiday Homes Under $200
Over 194+ Windward Private Villas, Airbnb and Holiday Homes Under $200
10.0
Exceptional
(52 Reviews)
- Port Charlotte - Charlotte Harbor
- Englewood
- 7.02 mi to center
768 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $167/Night
For 7 Nights US $1,168
10.0
Exceptional
(2 Reviews)
1453.13 ft²
6 Guests
2 Bedrooms
2 Bathrooms
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $154/Night
For 7 Nights US $1,078
8.0
Excellent
(3 Reviews)
- Port Charlotte - Charlotte Harbor
- Pebble Beach
- 0.20 mi to center
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Pool
- Kitchen
US $167/Night
For 7 Nights US $1,169
10.0
Exceptional
(47 Reviews)
- Port Charlotte - Charlotte Harbor
- Englewood
- 7.02 mi to center
768 ft²
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $153/Night
For 7 Nights US $1,070
10.0
Exceptional
(1 Review)
- Port Charlotte - Charlotte Harbor
- Englewood
- 6.89 mi to center
1227.09 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Parking
US $85/Night
For 7 Nights US $597
10.0
Exceptional
(20 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.58 mi to center
7 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $171/Night
For 7 Nights US $1,199
10.0
Exceptional
(17 Reviews)
- Port Charlotte - Charlotte Harbor
- Pebble Beach
- 0.37 mi to center
1385 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $192/Night
For 7 Nights US $1,345
10.0
Exceptional
(17 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.59 mi to center
1460 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $181/Night
For 7 Nights US $1,266
10.0
Exceptional
(9 Reviews)
- Port Charlotte - Charlotte Harbor
- Al Lago Village
- 0.03 mi to center
1540 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $179/Night
For 7 Nights US $1,251
Instantly Bookable Villa Rentals in Windward
Over 669+ Instantly Bookable Private Villas in or Near Windward
New
- Port Charlotte - Charlotte Harbor
- White Marsh
- 0.46 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
US $285/Night
For 7 Nights US $1,997
8.8
Fabulous
(10 Reviews)
- Port Charlotte - Charlotte Harbor
- Oakland Hills
- 0.56 mi to center
8 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Oceanfront
- Pool
US $204/Night
For 7 Nights US $1,428
10.0
Exceptional
(113 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 4.20 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $498/Night
For 7 Nights US $3,489
10.0
Exceptional
(86 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 4.09 mi to center
1200 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $443/Night
For 7 Nights US $3,102
10.0
Exceptional
(65 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.61 mi to center
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Oceanfront
- Fireplace/Heating
- Pool
US $292/Night
For 7 Nights US $2,045
10.0
Exceptional
(53 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.25 mi to center
1300 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Pool
- Ocean View
US $432/Night
For 7 Nights US $3,021
10.0
Exceptional
(27 Reviews)
- Port Charlotte - Charlotte Harbor
- Cape Haze
- 1.26 mi to center
1344 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $484/Night
For 7 Nights US $3,388
10.0
Exceptional
(16 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.81 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $327/Night
For 7 Nights US $2,287
10.0
Exceptional
(12 Reviews)
- Port Charlotte - Charlotte Harbor
- Placida
- 3.48 mi to center
946 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $343/Night
For 7 Nights US $2,404
Book a Last Minute Place to Stay in Windward
About Windward Vacation Rentals
There are more than 1168 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 1041.26 ft² on average, with prices averaging US $341 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.
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Top Private Villas, Resorts, and Rentals in Windward
| Type | Count |
|---|---|
| Vacation Homes | 823 |
| Villas | 150 |
| Holiday Apartments | 31 |
| Cottages | 18 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Windward
★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windward with BedroomVillas.
Weather in Windward, FL
View the weather forecast for Windward before booking your Windward Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
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 , kayaks, SUP POOL is CLOSED
- Gulf Front on an island,kayaks,tennis/pickleball SUP, 1 pet 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, Gulf view ,1 pet, tennis/pickleball Pool is closed at this time
- "She Sells Seashells" GULF VIEW Free Ferry ,Parking, Heated Pool, Boat Slip
- 'Incommunicado ' ~A~ Hammock, Cool Drink, Whispering Pines.
- 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
How many vacation rentals have private pools in Windward?
We have 430 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:
- Canal home, heated pool, close to everything!
- Manna Beach House
- Waterfront Island Home with Heated Pool & Dock – Walk to Pristine Beach - Kayaks
- Beautiful 2-Story 2B/2B w/Game Room, Pool, Overlooking Canal w/Boatslip
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.
- Savannah House Gulf Front, 2 Bd, 2 1/2 Bath Townhouse with Fantastic Sunsets!
- Near Golf and Beaches Luxe Home in Rotonda West!
- Florida Gulf Coast Getaway: Pool + Screened Lanai!
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 1168 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 | 64 |
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