1208+ Vacation Home Rentals in Windward |
Windward Vacation Rentals & Ski-in/Ski-out Homes
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.99 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
8 Guests
2500 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $984/Night
7 Nights - US $6,891
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.27 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
2002.09 ft²
Pool- Ocean View
- Balcony/Terrace
- View
US $186/Night
7 Nights - US $1,302
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $298/Night
7 Nights - US $2,086
House
- Port Charlotte - Charlotte Harbor
- ·
- Al Lago Village
- 0.09 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
Kitchen
US $297/Night
7 Nights - US $2,078
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.45 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1711.46 ft²
- Pool
- Balcony/Terrace
Pet Friendly
Parking
US $284/Night
7 Nights - US $1,988
House
- Port Charlotte - Charlotte Harbor
- ·
- Grove City
- 0.87 mi to center
9.8Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
Oceanfront
Hot Tub- Fireplace/Heating
- Ocean View
US $148/Night
7 Nights - US $1,034
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.85 mi to center
9.6Exceptional
(21 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $636/Night
7 Nights - US $4,454
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.59 mi to center
9.6Exceptional
(14 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $336/Night
7 Nights - US $2,352
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.27 mi to center
10.0Exceptional
(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $438/Night
7 Nights - US $3,066
Luxury Places to Stay in Windward
Over 1199+ Luxury Places to Stay in or Near Windward
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.65 mi to center
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
US $6,168/Night
7 Nights - US $43,179
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.06 mi to center
5 Bedrooms
6 Baths
12 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,649/Night
7 Nights - US $11,540
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.10 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
6 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,608/Night
7 Nights - US $11,255
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.45 mi to center
3 Bedrooms
2 Baths
6 Guests
1700.7 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $1,563/Night
7 Nights - US $10,944
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.06 mi to center
5 Bedrooms
6 Baths
12 Guests
10763.91 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $1,440/Night
7 Nights - US $10,080
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.73 mi to center
3 Bedrooms
3 Baths
6 Guests
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
US $1,234/Night
7 Nights - US $8,638
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.10 mi to center
9.8Exceptional
(13 Reviews)
5 Bedrooms
4 Baths
10 Guests
3461 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,018/Night
7 Nights - US $7,127
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.16 mi to center
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $968/Night
7 Nights - US $6,776
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.47 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1670 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $938/Night
7 Nights - US $6,566
Top-Rated Vacation Rentals with a Pool in Windward
Over 805+ Top-Rated Vacation Rentals with a Pool in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.58 mi to center
10.0Exceptional
(102 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $366/Night
7 Nights - US $2,564
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.51 mi to center
10.0Exceptional
(100 Reviews)
3 Bedrooms
2 Baths
6 Guests
1138 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $246/Night
7 Nights - US $1,723
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.57 mi to center
10.0Exceptional
(92 Reviews)
3 Bedrooms
2 Baths
6 Guests
2044 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $250/Night
7 Nights - US $1,752
House
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.32 mi to center
10.0Exceptional
(84 Reviews)
3 Bedrooms
3 Baths
6 Guests
2200 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $283/Night
7 Nights - US $1,983
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.89 mi to center
10.0Exceptional
(77 Reviews)
3 Bedrooms
2 Baths
6 Guests
1550 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $321/Night
7 Nights - US $2,246
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.54 mi to center
10.0Exceptional
(71 Reviews)
3 Bedrooms
2 Baths
10 Guests
2300 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $334/Night
7 Nights - US $2,341
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.61 mi to center
10.0Exceptional
(66 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $346/Night
7 Nights - US $2,424
Villa
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.46 mi to center
10.0Exceptional
(65 Reviews)
3 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $334/Night
7 Nights - US $2,335
House
- Port Charlotte - Charlotte Harbor
- ·
- Pinehurst
- 0.22 mi to center
10.0Exceptional
(58 Reviews)
3 Bedrooms
2 Baths
6 Guests
1920 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $226/Night
7 Nights - US $1,582
Pet-Friendly Vacation Rentals in Windward
Over 417+ Pet-Friendly Vacation Rentals in or Near Windward
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.14 mi to center
10.0Exceptional
(39 Reviews)
3 Bedrooms
2 Baths
8 Guests
1812 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $378/Night
7 Nights - US $2,646
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.54 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1345.49 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,645
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.49 mi to center
9.2Exceptional
(14 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $244/Night
7 Nights - US $1,708
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.79 mi to center
10.0Exceptional
(32 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $353/Night
7 Nights - US $2,472
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.78 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
812.67 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $192/Night
7 Nights - US $1,344
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.26 mi to center
10.0Exceptional
(30 Reviews)
2 Bedrooms
2 Baths
6 Guests
1344 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $484/Night
7 Nights - US $3,388
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.81 mi to center
10.0Exceptional
(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $361/Night
7 Nights - US $2,527
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.59 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
8 Guests
1460 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $162/Night
7 Nights - US $1,137
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.77 mi to center
10.0Exceptional
(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $520/Night
7 Nights - US $3,639
Large Vacation Homes & Villas in Windward
Over 233+ Large Vacation Homes & Villas in or Near Windward
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.18 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $453/Night
7 Nights - US $3,173
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.61 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
10 Guests
2152.78 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
US $280/Night
7 Nights - US $1,960
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.06 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $194/Night
7 Nights - US $1,358
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.49 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
Spa- Fireplace/Heating
- Pool
US $430/Night
7 Nights - US $3,013
House
- Port Charlotte - Charlotte Harbor
- ·
- Long Meadow
- 0.38 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
10 Guests
2604.87 ft²
- Private Beach
- Oceanfront
- Pool
- Ocean View
US $221/Night
7 Nights - US $1,544
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.40 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $377/Night
7 Nights - US $2,642
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.31 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $345/Night
7 Nights - US $2,413
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
9.8Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $322/Night
7 Nights - US $2,252
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.50 mi to center
9.6Exceptional
(88 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $271/Night
7 Nights - US $1,897
Wheelchair Accessible Vacation Homes in Windward
Over 86+ Wheelchair Accessible Vacation Homes in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.38 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $144/Night
7 Nights - US $1,006
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.48 mi to center
9.0Exceptional
(1 Review)
1 Bedroom
2 Baths
4 Guests
1054.86 ft²
- Private Beach
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $173/Night
7 Nights - US $1,213
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.18 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $406/Night
7 Nights - US $2,841
Villa
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.50 mi to center
8.6Fabulous
(5 Reviews)
3 Bedrooms
1 Bath
6 Guests
2303.48 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $151/Night
7 Nights - US $1,057
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 5.22 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $167/Night
7 Nights - US $1,171
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.57 mi to center
9.8Exceptional
(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $314/Night
7 Nights - US $2,195
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
9.6Exceptional
(21 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $353/Night
7 Nights - US $2,469
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
9.4Exceptional
(140 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $352/Night
7 Nights - US $2,467
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.98 mi to center
9.4Exceptional
(6 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $245/Night
7 Nights - US $1,717
Windward Resorts and Airbnb Homes Under $200
Over 239+ Windward Resorts and Airbnb Homes Under $200
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.58 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $124/Night
7 Nights - US $870
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Grove City
- 0.90 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Private Beach
- Oceanfront
- Ocean View
- View
US $116/Night
7 Nights - US $814
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.20 mi to center
8.0Excellent
(3 Reviews)
1 Bedroom
1 Bath
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $167/Night
7 Nights - US $1,169
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.40 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $141/Night
7 Nights - US $989
House
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 6.89 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1227.09 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Parking
US $85/Night
7 Nights - US $597
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.19 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $135/Night
7 Nights - US $946
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.31 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $122/Night
7 Nights - US $856
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 6.71 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
1010 ft²
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $116/Night
7 Nights - US $815
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.65 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $176/Night
7 Nights - US $1,232
Instantly Bookable Vacation Homes in Windward
Over 705+ Instantly Bookable Vacation Homes in or Near Windward
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.95 mi to center
10.0Exceptional
(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $341/Night
7 Nights - US $2,385
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.55 mi to center
9.6Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $323/Night
7 Nights - US $2,262
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.48 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
946 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $320/Night
7 Nights - US $2,243
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.19 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
3 Baths
6 Guests
1024 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $411/Night
7 Nights - US $2,875
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 4.04 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
3 Baths
8 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $393/Night
7 Nights - US $2,754
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.23 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1160 ft²
- Private Pool
- Pool
- Pet Friendly
- Internet
US $500/Night
7 Nights - US $3,503
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.26 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $244/Night
7 Nights - US $1,709
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.47 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $416/Night
7 Nights - US $2,912
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.25 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1459 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $211/Night
7 Nights - US $1,477
Book a Last Minute Place to Stay in Windward
About Windward Vacation Rentals
Explore over 1208 vacation rentals in Windward with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Windward for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Windward. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Windward tailored to your preferences. On average, these rentals offer 1071.06 ft² of space, and are priced at an average of US $333 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Windward at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Windward
| Type | Count |
|---|---|
| Vacation Homes | 856 |
| Villas | 149 |
| Holiday Apartments | 31 |
| Cottages | 17 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Windward
★ Pro Tip: Discover Your Ideal Vacation Rental in Windward with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
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 vacation rentals in Windward?
When organizing your trip to Windward, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Windward. Peruse our collection of highly-rated properties and secure your reservation today.
- 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
- Waterfront 2BR beach & lagoon retreat. Dock, pool, dog-friendly. Incommunicado!
- A Little Slice of Paradise
- Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
- Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa.
- Seeing is Believing! Incredible Boca Vista Harbor Waterfront Condo!
- Savannah House Gulf Front, 2 Bd, 2 1/2 Bath Townhouse with Fantastic Sunsets!
- Cloud 9 on LGI Beach! No Roads. No Cars. Just Island Life w/Beach to Bay Views.
- Island Breeze
How many vacation rentals have private pools in Windward?
Uncover 445 vacation rentals boasting private pools near Windward. Explore top-rated RBO homes offering access to a swimming pool:
- Canal home, pool, close to everything!
- Manna Beach House
- Spacious Ocean Cove House On the Golf Course *HEATED POOL*
- Remodeled Tropical Paradise! Livin' The Dream HBBC - Little Gasparilla Island
Which vacation homes or resorts in Windward are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Windward. Enjoy great views, locations and save money with SunSki Resorts.™
- Savannah House Gulf Front, 2 Bd, 2 1/2 Bath Townhouse with Fantastic Sunsets!
- Near Golf & Beaches: Luxe Home in Rotonda West!
- Spacious Ocean Cove House On the Golf Course *HEATED POOL*
How many SunSkiResorts vacation rentals or resorts are available in Windward?
Discover the ideal vacation rental in Windward with SunSki Resorts™. We provide an extensive selection of over 1208 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Windward.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cape Haze Vacation Rentals in Florida | 61 |
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