Tree House Rentals in Windward, FL
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.43 mi to center
2 Bedrooms
2 Baths
4 Guests
Ocean View
View
Kitchen
Air Conditioner
US $556/Night
7 Nights - US $3,892
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
Parking
Pool
Balcony/Terrace
Internet
US $308/Night
7 Nights - US $2,156
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.34 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $298/Night
7 Nights - US $2,086
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.43 mi to center
2 Bedrooms
2 Baths
4 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $493/Night
7 Nights - US $3,449
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.62 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1636.11 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $235/Night
7 Nights - US $1,647
New
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.60 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
Private Pool
Hot Tub- Parking
- Pool
US $599/Night
7 Nights - US $4,195
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.58 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $331/Night
7 Nights - US $2,319
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.27 mi to center
10.0Exceptional
(179 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $476/Night
7 Nights - US $3,334
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.23 mi to center
10.0Exceptional
(106 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $399/Night
7 Nights - US $2,791
Luxury Tree House Rentals in Windward
Over 1271+ Luxury Tree House Rentals in or Near Windward
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.65 mi to center
3 Bedrooms
2 Baths
7 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $6,509/Night
7 Nights - US $45,560
New
House
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.54 mi to center
3 Bedrooms
2 Baths
6 Guests
3003.13 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $5,105/Night
7 Nights - US $35,738
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.73 mi to center
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,821/Night
7 Nights - US $19,748
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.06 mi to center
5 Bedrooms
6 Baths
12 Guests
- Hot Tub
- Parking
- Ocean View
- View
US $2,040/Night
7 Nights - US $14,280
New
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.78 mi to center
10.0Exceptional
(4 Reviews)
5 Bedrooms
6 Baths
12 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,855/Night
7 Nights - US $12,985
House
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(17 Reviews)
6 Bedrooms
1 Bath
20 Guests
3072 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,549/Night
7 Nights - US $10,846
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.06 mi to center
5 Bedrooms
6 Baths
12 Guests
10763.91 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $1,440/Night
7 Nights - US $10,080
New
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.89 mi to center
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,438/Night
7 Nights - US $10,067
New
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.89 mi to center
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $1,437/Night
7 Nights - US $10,060
Top-Rated Treehouses with a Pool in Windward
Over 807+ Top-Rated Private Treehouses with a Pool in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.51 mi to center
10.0Exceptional
(100 Reviews)
2 Bedrooms
2 Baths
6 Guests
1138 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $269/Night
7 Nights - US $1,885
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.16 mi to center
10.0Exceptional
(98 Reviews)
3 Bedrooms
2 Baths
5 Guests
1748 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $177/Night
7 Nights - US $1,238
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.57 mi to center
10.0Exceptional
(97 Reviews)
3 Bedrooms
2 Baths
6 Guests
2044 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $230/Night
7 Nights - US $1,612
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.15 mi to center
10.0Exceptional
(93 Reviews)
3 Bedrooms
3 Baths
6 Guests
1800 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $248/Night
7 Nights - US $1,737
House
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.32 mi to center
10.0Exceptional
(85 Reviews)
3 Bedrooms
3 Baths
6 Guests
2200 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $296/Night
7 Nights - US $2,075
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.89 mi to center
10.0Exceptional
(77 Reviews)
3 Bedrooms
2 Baths
6 Guests
1550 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $323/Night
7 Nights - US $2,261
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.39 mi to center
10.0Exceptional
(77 Reviews)
3 Bedrooms
2 Baths
7 Guests
1750 ft²
- Pool
- Ocean View
- View
- Kitchen
US $227/Night
7 Nights - US $1,591
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.54 mi to center
10.0Exceptional
(75 Reviews)
3 Bedrooms
2 Baths
10 Guests
2300 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $323/Night
7 Nights - US $2,262
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(71 Reviews)
2 Bedrooms
1 Bath
6 Guests
768 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $287/Night
7 Nights - US $2,008
Pet-Friendly Treehouses in Windward
Over 447+ Pet-Friendly Private Treehouses in or Near Windward
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(64 Reviews)
3 Bedrooms
1 Bath
6 Guests
768 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $323/Night
7 Nights - US $2,264
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
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $229/Night
7 Nights - US $1,606
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.70 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $386/Night
7 Nights - US $2,702
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.62 mi to center
10.0Exceptional
(62 Reviews)
3 Bedrooms
2 Baths
6 Guests
1550 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $500/Night
7 Nights - US $3,497
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.39 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463.89 ft²
- Parking
- Pool
Spa- Balcony/Terrace
US $227/Night
7 Nights - US $1,591
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.25 mi to center
10.0Exceptional
(61 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $517/Night
7 Nights - US $3,622
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
768 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $287/Night
7 Nights - US $2,008
Apartment
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.02 mi to center
10.0Exceptional
(51 Reviews)
2 Bedrooms
1 Bath
4 Guests
768 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $299/Night
7 Nights - US $2,092
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.14 mi to center
10.0Exceptional
(46 Reviews)
2 Bedrooms
2 Baths
8 Guests
1812 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $392/Night
7 Nights - US $2,742
Large Private Treehouses in Windward
Over 235+ Large Treehouses in or Near Windward for Groups and Families
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
- Hot Tub
- Parking
- Pool
US $334/Night
7 Nights - US $2,341
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.34 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
10 Guests
1496.18 ft²
- View
- Air Conditioner
- Internet
- Child Friendly
US $591/Night
7 Nights - US $4,135
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.06 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $194/Night
7 Nights - US $1,358
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.15 mi to center
10.0Exceptional
(57 Reviews)
4 Bedrooms
4 Baths
8 Guests
2900 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $288/Night
7 Nights - US $2,013
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.12 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
10 Guests
2002.09 ft²
- Private Pool
- Parking
- Pool
- View
US $158/Night
7 Nights - US $1,108
House
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.26 mi to center
10.0Exceptional
(50 Reviews)
4 Bedrooms
2 Baths
10 Guests
2200 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $271/Night
7 Nights - US $1,894
Villa
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.30 mi to center
10.0Exceptional
(46 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $238/Night
7 Nights - US $1,663
House
- Port Charlotte - Charlotte Harbor
- ·
- Broadmoor
- 0.48 mi to center
10.0Exceptional
(31 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $734/Night
7 Nights - US $5,135
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.69 mi to center
10.0Exceptional
(28 Reviews)
4 Bedrooms
4 Baths
10 Guests
3200 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $911/Night
7 Nights - US $6,374
Wheelchair Accessible Holiday Homes in Windward
Over 91+ Wheelchair Accessible Treehouses and Holiday Homes in or Near Windward
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.20 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1111 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $519/Night
7 Nights - US $3,635
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- Parking
- Ocean View
- Balcony/Terrace
US $173/Night
7 Nights - US $1,213
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.16 mi to center
10.0Exceptional
(10 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $1,127/Night
7 Nights - US $7,888
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
- Parking
- Pool
- Spa
US $151/Night
7 Nights - US $1,057
House
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.00 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
2300 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $183/Night
7 Nights - US $1,281
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 5.22 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $181/Night
7 Nights - US $1,269
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 1.18 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1700 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $300/Night
7 Nights - US $2,100
House
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 1.13 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $623/Night
7 Nights - US $4,360
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 1.88 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $311/Night
7 Nights - US $2,180
Windward Treehouses, Airbnb and Holiday Homes Under $200
Over 173+ Windward Private Treehouses, Airbnb and Holiday Homes Under $200
House
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.14 mi to center
10.0Exceptional
(29 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $196/Night
7 Nights - US $1,369
House
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 6.89 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1227.09 ft²
- Parking
- Pool
- Balcony/Terrace
- Internet
US $85/Night
7 Nights - US $597
Villa
- Port Charlotte - Charlotte Harbor
- ·
- Englewood
- 7.06 mi to center
6.0Good
(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Hot Tub
- Parking
- Pool
US $194/Night
7 Nights - US $1,358
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.58 mi to center
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $193/Night
7 Nights - US $1,348
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.37 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
6 Guests
1388.54 ft²
- Parking
- Pool
- Spa
- Balcony/Terrace
US $193/Night
7 Nights - US $1,349
House
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.59 mi to center
10.0Exceptional
(19 Reviews)
2 Bedrooms
2 Baths
8 Guests
1460 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $175/Night
7 Nights - US $1,227
House
- Port Charlotte - Charlotte Harbor
- ·
- Pebble Beach
- 0.45 mi to center
10.0Exceptional
(17 Reviews)
3 Bedrooms
2 Baths
8 Guests
2100 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $196/Night
7 Nights - US $1,375
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Al Lago Village
- 0.03 mi to center
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
1540 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $189/Night
7 Nights - US $1,324
House
- Port Charlotte - Charlotte Harbor
- ·
- Al Lago Village
- 0.09 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $159/Night
7 Nights - US $1,112
Instantly Bookable Treehouse Rentals in Windward
Over 747+ Instantly Bookable Private Treehouses in or Near Windward
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 4.09 mi to center
10.0Exceptional
(89 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $509/Night
7 Nights - US $3,561
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.44 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $420/Night
7 Nights - US $2,943
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
- Parking
- Pool
- Balcony/Terrace
US $295/Night
7 Nights - US $2,068
House
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.81 mi to center
10.0Exceptional
(51 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $424/Night
7 Nights - US $2,968
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.48 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
2 Baths
4 Guests
946 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $354/Night
7 Nights - US $2,475
Condo
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.61 mi to center
10.0Exceptional
(41 Reviews)
2 Bedrooms
2 Baths
6 Guests
926 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $350/Night
7 Nights - US $2,449
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Placida
- 3.79 mi to center
10.0Exceptional
(38 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $351/Night
7 Nights - US $2,455
House
- Port Charlotte - Charlotte Harbor
- ·
- Al Lago Village
- 0.09 mi to center
10.0Exceptional
(36 Reviews)
3 Bedrooms
2 Baths
6 Guests
1350 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $348/Night
7 Nights - US $2,436
Cottage
- Port Charlotte - Charlotte Harbor
- ·
- Oakland Hills
- 0.42 mi to center
10.0Exceptional
(35 Reviews)
3 Bedrooms
2 Baths
8 Guests
2100 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $356/Night
7 Nights - US $2,490
Book a Last Minute Place to Stay in Windward
About Windward Treehouse Rentals
Explore more than 1280 treehouses in Windward. From luxurious treetop retreats to cozy forest homes, cabins and off-grid properties, each offers premium amenities designed for families, groups, and adventurers. Enjoy exceptional comfort and a one-of-a-kind nature experience with these incredible accommodations. Perfect for tranquil escapes, adventurous retreats, or nature-inspired getaways, these treehouses provide style and comfort in Windward.
Looking for last-minute deals or the best offers on treehouses, cozy forest homes, cabins and off-grid properties? Treehouse Rentals makes it easy to compare options in Windward. Choose from spacious family-friendly stays, charming woodland escapes, or luxurious treetop getaways tailored for ultimate relaxation and adventure
Find spacious family-friendly accommodations, cozy forest homes, or luxurious treetop stays—all designed for maximum comfort and convenience during your visit.On average, treehouses in Windward offer approximately 1158.63 ft² of space, giving you and your group plenty of room to relax and enjoy the stunning natural surroundings.
The average nightly rate for treehouses in Windward typically ranges around US $386.
Treehouse Rentals offers a secure and convenient platform to compare and book the best treehouses in Windward. Explore a wide range of properties at unbeatable rates, and enjoy a unique stay immersed in nature with us.
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Top Treehouse Accommodation Types in Windward
| Type | Count |
|---|---|
| Vacation Homes | 907 |
| Villas | 143 |
| Holiday Apartments | 32 |
| Cottages | 28 |
Use these Quick Filters to Find a Vacation Rental in Windward
★ Pro Tip: Treehouse Rentals simplifies your search for the best treehouse accommodations from leading vacation rental OTAs like Booking.com and more. Use our Advanced Filter to explore treehouses, cozy cabins, secluded forest homes and off-grid properties. Filter by availability, pricing, cancellation options, and amenities to discover the ideal treehouse getaway in Windward.
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 treehouse rentals in Windward?
Looking for a place to stay in Windward? Explore these highly-rated treehouses for a one-of-a-kind retreat surrounded by nature:
- Charming Tropical Treehouse with Kayaks near Little Gasparilla Island, Florida
- Key2TheSea: Tropical treehouse with lots of decks, porches and privacy!
- Gulf Front on a ISLAND, 1 pet, tennis, pickleball,sup,kayak. POOL is CLOSED
- 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
- Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa.
How many treehouses with private pools are available in Windward?
Find exceptional treehouses with private pools near Windward on Treehouse Rentals. Relax in serene treetop accommodations with exclusive pool access and picturesque nature views. Whether it's a spacious treehouse or a secluded forest retreat, these properties provide the ideal mix of luxury and adventure.
- Your Florida home away from home. Restaurants, entertaining, pool and beach.
- Manna Beach House
- Spacious Ocean Cove House On the Golf Course *HEATED POOL*
- Nature's Splendor! Lovely Setting.
What are the top-rated treehouses in Windward for family stays?
Searching for a family-friendly treehouse in Windward? Discover these top-rated options, each loved by families and groups who have stayed in Windward:
- Cloud 9 on LGI Beach! No Roads. No Cars. Just Island Life w/Beach to Bay Views.
- Beachfront Island Condo on Florida Gulf Coast
- Pool + Screened Lanai! Florida Gulf Coast Getaway
How many treehouses are available in Windward?
Treehouse Rentals, as of 2026, features over 1280 unique treehouse, cabins and forest homes in Windward. Choose from treetop hideaways, eco-friendly lodges, and off-grid properties, with new options added frequently.
By 2026, Treehouse Rentals has curated over 1280 stunning properties in Windward, sourced from trusted platforms. Plan your nature-inspired getaway now.
For 2026, Treehouse Rentals provides access to over 1280 premier accommodations in Windward. Find your ideal escape among the treetops today.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cape Haze Vacation Rentals in Florida | 59 |
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