1208+ Luxury Vacation Rentals & Cabins in Windward |
Windward Cabin Rentals
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.88 mi to center
3 Bedrooms
3 Baths
6 Guests
Oceanfront
Fireplace/Heating
Ocean View
View
US $647/Night
7 Nights - US $4,531
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
New
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.46 mi to center
3 Bedrooms
3 Baths
6 Guests
2498 ft²
Pet Friendly
Internet
Child Friendly
Security/Safety
US $600/Night
7 Nights - US $4,199
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 $273/Night
7 Nights - US $1,911
House
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.20 mi to center
3 Bedrooms
4 Baths
8 Guests
Air Conditioner- Internet
- Child Friendly
Laundry
US $299/Night
7 Nights - US $2,091
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.54 mi to center
3 Bedrooms
2 Baths
6 Guests
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $249/Night
7 Nights - US $1,741
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.28 mi to center
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $249/Night
7 Nights - US $1,740
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.65 mi to center
3 Bedrooms
2 Baths
5 Guests
1700 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $188/Night
7 Nights - US $1,313
Luxury Places to Stay in Windward
Over 1199+ Luxury Places to Stay in or Near Windward
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.12 mi to center
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
1860 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $806/Night
7 Nights - US $5,645
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.20 mi to center
8.8Fabulous
(25 Reviews)
5 Bedrooms
3 Baths
10 Guests
3600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $595/Night
7 Nights - US $4,167
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.44 mi to center
9.2Exceptional
(34 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $571/Night
7 Nights - US $3,997
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.77 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $558/Night
7 Nights - US $3,907
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.87 mi to center
9.8Exceptional
(99 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $524/Night
7 Nights - US $3,670
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.26 mi to center
10.0Exceptional
(27 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
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $468/Night
7 Nights - US $3,278
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.49 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $466/Night
7 Nights - US $3,265
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.94 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $459/Night
7 Nights - US $3,213
Top-Rated Cabins with a Pool in Windward
Over 800+ Top-Rated Cabins with a Pool in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.14 mi to center
10.0Exceptional
(113 Reviews)
3 Bedrooms
2 Baths
8 Guests
1702 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $427/Night
7 Nights - US $2,988
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 $234/Night
7 Nights - US $1,636
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.89 mi to center
10.0Exceptional
(76 Reviews)
3 Bedrooms
2 Baths
6 Guests
1550 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $312/Night
7 Nights - US $2,184
House
- Port Charlotte - Charlotte Harbor
- ·
- Broadmoor
- 0.60 mi to center
10.0Exceptional
(46 Reviews)
3 Bedrooms
2 Baths
8 Guests
2100 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $213/Night
7 Nights - US $1,490
House
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.50 mi to center
10.0Exceptional
(25 Reviews)
3 Bedrooms
1 Bath
9 Guests
2040 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $273/Night
7 Nights - US $1,909
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Long Meadow
- 0.30 mi to center
10.0Exceptional
(24 Reviews)
3 Bedrooms
2 Baths
6 Guests
2390 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $237/Night
7 Nights - US $1,659
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.80 mi to center
10.0Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
6 Guests
2200 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $225/Night
7 Nights - US $1,573
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 $342/Night
7 Nights - US $2,391
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.30 mi to center
10.0Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
6 Guests
1423 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $424/Night
7 Nights - US $2,966
Pet-Friendly Cabins in Windward
Over 416+ Pet-Friendly Cabins in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.27 mi to center
10.0Exceptional
(166 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $438/Night
7 Nights - US $3,066
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
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.27 mi to center
10.0Exceptional
(158 Reviews)
2 Bedrooms
2 Baths
6 Guests
1150 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $456/Night
7 Nights - US $3,195
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
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.58 mi to center
10.0Exceptional
(101 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $370/Night
7 Nights - US $2,587
Cabin
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.38 mi to center
10.0Exceptional
(69 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $314/Night
7 Nights - US $2,195
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(65 Reviews)
2 Bedrooms
1 Bath
6 Guests
768 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $298/Night
7 Nights - US $2,085
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(57 Reviews)
3 Bedrooms
1 Bath
6 Guests
768 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $299/Night
7 Nights - US $2,092
Large Cabins in Windward
Over 237+ Large Cabins 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 $466/Night
7 Nights - US $3,264
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 $448/Night
7 Nights - US $3,136
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 $392/Night
7 Nights - US $2,742
New
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 $359/Night
7 Nights - US $2,515
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 $324/Night
7 Nights - US $2,267
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
9.6Exceptional
(126 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $480/Night
7 Nights - US $3,357
Wheelchair Accessible Cabins in Windward
Over 89+ Wheelchair Accessible Cabins in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.83 mi to center
10.0Exceptional
(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $325/Night
7 Nights - US $2,274
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
- 1.20 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
1111 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $449/Night
7 Nights - US $3,141
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
- ·
- 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
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 $249/Night
7 Nights - US $1,746
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 $168/Night
7 Nights - US $1,179
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.62 mi to center
9.8Exceptional
(73 Reviews)
2 Bedrooms
2 Baths
6 Guests
1138 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $226/Night
7 Nights - US $1,581
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 $320/Night
7 Nights - US $2,242
Windward Cabins Under $200
Over 223+ Windward Cabins 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 $133/Night
7 Nights - US $933
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
- ·
- Pebble Beach
- 0.37 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1385 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $186/Night
7 Nights - US $1,304
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
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.59 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
8 Guests
1460 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $162/Night
7 Nights - US $1,137
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 6.72 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $179/Night
7 Nights - US $1,252
House
- Port Charlotte - Charlotte Harbor
- ·
- Long Meadow
- 0.39 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
1688 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $190/Night
7 Nights - US $1,330
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 $152/Night
7 Nights - US $1,062
Instantly Bookable Cabins in Windward
Over 703+ Instantly Bookable Cabins in or Near Windward
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 4.20 mi to center
10.0Exceptional
(115 Reviews)
2 Bedrooms
3 Baths
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $508/Night
7 Nights - US $3,559
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
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 4.09 mi to center
10.0Exceptional
(86 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $473/Night
7 Nights - US $3,310
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.61 mi to center
10.0Exceptional
(65 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $292/Night
7 Nights - US $2,045
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.25 mi to center
10.0Exceptional
(56 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $464/Night
7 Nights - US $3,250
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(53 Reviews)
2 Bedrooms
1 Bath
4 Guests
768 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $298/Night
7 Nights - US $2,085
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(49 Reviews)
2 Bedrooms
1 Bath
4 Guests
768 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $298/Night
7 Nights - US $2,085
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 $302/Night
7 Nights - US $2,116
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.95 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Air Conditioner
US $347/Night
7 Nights - US $2,430
Book a Last Minute Place to Stay in Windward
About Windward Vacation Rentals
There are more than 1208 incredible getaway rentals that are available in Windward. These choices include cabins, 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. Stay Close to Nature with Cabinns.com and uncover great stays in Windward.
Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin 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 Cabinns.com 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 Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Windward. Places to stay near Windward are 1071.14 ft² on average, with prices averaging US $330 a night.
Cabinns.com helps you find the ideal holiday rental to create a lifetime of 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 cabin retreat today.
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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Windward
| Type | Count |
|---|---|
| Vacation Homes | 853 |
| Villas | 151 |
| Holiday Apartments | 31 |
| Cottages | 18 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Windward
★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts 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 Cabinns.com.
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 cabins, lake houses & summer homes 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 cabin resort or 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
- Waterfront, Gulf View, pool, tennis, pickleball, kayaks, SUP, dock
- A Little Slice of Paradise
- Seeing is Believing! Incredible Boca Vista Harbor Waterfront Condo!
- Little Gasparilla Island: WATERFRONT Cabin, Boat dock at front door!
- Your Florida home away from home. Restaurants, entertaining, pool and beach.
- Pet friendly, on the beach, paddle boards, kayaks, bikes
- Luxurious & Spacious Canal Home with Heated Pool
- Fabulous private villa with superb south-facing golf course views
- Tropical Retreat - Oversized heated pool, golf, pickle-ball, tennis, bikes,
How many cabin rentals and resorts have private pools in Windward?
We have 445 cabins, luxury resorts, and holiday home rentals featuring 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, pool, close to everything!
- Manna Beach House
- Spacious Ocean Cove House On the Golf Course *HEATED POOL*
- Waterfront Island Home with Heated Pool & Dock – Walk to Pristine Beach - Kayaks
Which cabin rental, resort, or holiday home in Windward is best for families?
Searching for a family-friendly cabin in Windward? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.
- "She Sells Seashells" GULF VIEW Free Ferry ,Parking, Heated Pool, Boat Slip
- Near Golf & Beaches: Luxe Home in Rotonda West!
- Florida Gulf Coast Getaway: Pool + Screened Lanai!
How many hotels, resorts, or cabin rentals are available in Windward?
Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2026 is over 1208 in the Windward area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com 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 Cabins and Private Getaways in Florida | 52 |
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