Tree House Rentals in The Meadows
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
Oceanfront
Parking
Pool
Ocean View
US $589/Night
7 Nights - US $4,122
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Parking
- Pool
View
Air Conditioner
US $406/Night
7 Nights - US $2,844
Bed & Breakfast
- Key West
- ·
- The Meadows
- 0.12 mi to center
9.2Exceptional
(1022 Reviews)
1 Bedroom
1 Bath
Breakfast- Pool
Balcony/Terrace
Kitchen
US $134/Night
7 Nights - US $937
House
- Key West
- ·
- The Meadows
- 0.13 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1020 ft²
Private Pool- Parking
- Pool
- Balcony/Terrace
US $277/Night
7 Nights - US $1,939
House
9.9Exceptional
(16 Reviews)
2 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $785/Night
7 Nights - US $5,494
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1283 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $449/Night
7 Nights - US $3,140
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $562/Night
7 Nights - US $3,936
Boat Rental
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $507/Night
7 Nights - US $3,546
Apartment
- Key West
- ·
- The Meadows
- 0.12 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $278/Night
7 Nights - US $1,949
Luxury Tree House Rentals in The Meadows
Over 134+ Luxury Tree House Rentals in or Near The Meadows
House
1 Bedroom
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $2,792/Night
7 Nights - US $19,544
House
9.6Exceptional
(17 Reviews)
4 Bedrooms
4 Baths
8 Guests
2444 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $2,227/Night
7 Nights - US $15,590
House
4 Bedrooms
4 Baths
10 Guests
2830.91 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $2,086/Night
7 Nights - US $14,605
House
8.1Excellent
(13 Reviews)
4 Bedrooms
4 Baths
16 Guests
2002.09 ft²
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
US $2,063/Night
7 Nights - US $14,441
House
9.3Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
16 Guests
2002.09 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $2,063/Night
7 Nights - US $14,441
House
8.9Fabulous
(12 Reviews)
4 Bedrooms
4 Baths
16 Guests
2400.35 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $2,063/Night
7 Nights - US $14,441
House
4 Bedrooms
4 Baths
8 Guests
2443.41 ft²
Child Friendly
Security/Safety
US $1,986/Night
7 Nights - US $13,904
House
4 Bedrooms
3 Baths
10 Guests
2895.49 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $1,832/Night
7 Nights - US $12,826
House
9.2Exceptional
(9 Reviews)
4 Bedrooms
4 Baths
15 Guests
2400.35 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,672/Night
7 Nights - US $11,704
Top-Rated Treehouses with a Pool in The Meadows
Over 109+ Top-Rated Private Treehouses with a Pool in or Near The Meadows
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1642 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $250/Night
7 Nights - US $1,750
House
- Key West
- ·
- The Meadows
- 0.08 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1596 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $339/Night
7 Nights - US $2,374
Condo
- Key West
- ·
- The Meadows
- 0.13 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
455 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $558/Night
7 Nights - US $3,903
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1800 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $908/Night
7 Nights - US $6,358
Condo
- Key West
- ·
- The Meadows
- 0.13 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
427 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $163/Night
7 Nights - US $1,143
House
9.8Exceptional
(156 Reviews)
4 Bedrooms
3 Baths
10 Guests
2898 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,344/Night
7 Nights - US $9,409
House
9.8Exceptional
(147 Reviews)
5 Bedrooms
4 Baths
12 Guests
3605 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,428/Night
7 Nights - US $9,999
House
9.8Exceptional
(146 Reviews)
3 Bedrooms
3 Baths
8 Guests
2849 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,016/Night
7 Nights - US $7,110
House
9.8Exceptional
(136 Reviews)
4 Bedrooms
3 Baths
10 Guests
2898 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,077/Night
7 Nights - US $7,538
Pet-Friendly Treehouses in The Meadows
Over 53+ Pet-Friendly Private Treehouses in or Near The Meadows
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
639 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
US $172/Night
7 Nights - US $1,204
House
9.4Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
8 Guests
1205.56 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $919/Night
7 Nights - US $6,433
House
- Key West
- ·
- The Meadows
- 0.11 mi to center
9.8Exceptional
(124 Reviews)
1 Bedroom
1 Bath
4 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $190/Night
7 Nights - US $1,328
House
9.2Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
8 Guests
1345.49 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $684/Night
7 Nights - US $4,788
Condo
9.8Exceptional
(39 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $530/Night
7 Nights - US $3,713
Condo
9.8Exceptional
(27 Reviews)
2 Bedrooms
2 Baths
8 Guests
1350 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $572/Night
7 Nights - US $4,003
House
- Key West
- ·
- The Meadows
- 0.07 mi to center
9.8Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
1142 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $313/Night
7 Nights - US $2,188
House
- Key West
- ·
- The Meadows
- 0.11 mi to center
9.6Exceptional
(117 Reviews)
1 Bedroom
1 Bath
2 Guests
612 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $180/Night
7 Nights - US $1,260
Condo
9.6Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $727/Night
7 Nights - US $5,088
Large Private Treehouses in The Meadows
Over 16+ Large Treehouses in or Near The Meadows for Groups and Families
House
9.8Exceptional
(91 Reviews)
4 Bedrooms
3 Baths
10 Guests
2829 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,167/Night
7 Nights - US $8,166
House
- Key West
- ·
- The Meadows
- 0.12 mi to center
8.8Fabulous
(970 Reviews)
16 Bedrooms
13 Baths
31 Guests
266.61 ft²
- Pool
- Balcony/Terrace
- View
- Air Conditioner
US $159/Night
7 Nights - US $1,113
Condo
9.8Exceptional
(32 Reviews)
4 Bedrooms
4 Baths
16 Guests
2400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $835/Night
7 Nights - US $5,843
House
4 Bedrooms
3 Baths
10 Guests
2895.49 ft²
- Hot Tub
- Breakfast
- Parking
- Pool
US $1,652/Night
7 Nights - US $11,561
House
9.8Exceptional
(13 Reviews)
5 Bedrooms
4 Baths
12 Guests
3417 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,028/Night
7 Nights - US $7,193
Condo
9.6Exceptional
(41 Reviews)
4 Bedrooms
4 Baths
16 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,008/Night
7 Nights - US $7,054
Condo
9.6Exceptional
(37 Reviews)
4 Bedrooms
4 Baths
16 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,353/Night
7 Nights - US $9,468
Condo
9.6Exceptional
(35 Reviews)
4 Bedrooms
4 Baths
15 Guests
2400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $835/Night
7 Nights - US $5,843
House
- Key West
- ·
- The Meadows
- 0.03 mi to center
5 Bedrooms
3 Baths
12 Guests
3316 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,305/Night
7 Nights - US $9,137
Wheelchair Accessible Holiday Homes in The Meadows
Over 18+ Wheelchair Accessible Treehouses and Holiday Homes in or Near The Meadows
Condo
9.6Exceptional
(72 Reviews)
2 Bedrooms
1 Bath
4 Guests
693 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $478/Night
7 Nights - US $3,343
Condo
9.6Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $556/Night
7 Nights - US $3,895
Condo
9.4Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $558/Night
7 Nights - US $3,905
Condo
9.2Exceptional
(109 Reviews)
2 Bedrooms
2 Baths
8 Guests
1215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $495/Night
7 Nights - US $3,463
Condo
9.2Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $575/Night
7 Nights - US $4,027
Condo
9.0Exceptional
(108 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $495/Night
7 Nights - US $3,465
Condo
9.8Exceptional
(135 Reviews)
4 Bedrooms
4 Baths
8 Guests
1498 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,090/Night
7 Nights - US $7,628
Condo
9.8Exceptional
(83 Reviews)
4 Bedrooms
4 Baths
8 Guests
1453 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,094/Night
7 Nights - US $7,658
Condo
9.8Exceptional
(66 Reviews)
4 Bedrooms
3 Baths
8 Guests
1237 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,004/Night
7 Nights - US $7,031
The Meadows Treehouses, Airbnb and Holiday Homes Under $200
Over 7+ The Meadows Private Treehouses, Airbnb and Holiday Homes Under $200
Condo
- Key West
- ·
- The Meadows
- 0.13 mi to center
8.8Fabulous
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
427 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $163/Night
7 Nights - US $1,144
House
- Key West
- ·
- The Meadows
- 0.12 mi to center
9.0Exceptional
(1017 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $193/Night
7 Nights - US $1,354
Condo
7.6Very Good
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Pool
- Kitchen
- Air Conditioner
Internet
US $150/Night
7 Nights - US $1,049
House
- Key West
- ·
- The Meadows
- 0.06 mi to center
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $198/Night
7 Nights - US $1,385
New
House
- Key West
- ·
- The Meadows
- 0.09 mi to center
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $195/Night
7 Nights - US $1,362
Condo
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $191/Night
7 Nights - US $1,339
Condo
- Key West
- ·
- The Meadows
- 0.12 mi to center
9.2Exceptional
(131 Reviews)
1 Bedroom
1 Bath
4 Guests
455 ft²
- Oceanfront
- Hot Tub
- Pool
Spa
US $165/Night
7 Nights - US $1,155
Instantly Bookable Treehouse Rentals in The Meadows
Over 44+ Instantly Bookable Private Treehouses in or Near The Meadows
Boat Rental
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
Bedding/Linens- Security/Safety
US $1,073/Night
7 Nights - US $7,513
Condo
9.6Exceptional
(110 Reviews)
4 Bedrooms
4 Baths
8 Guests
1454 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,042/Night
7 Nights - US $7,296
Condo
9.6Exceptional
(101 Reviews)
4 Bedrooms
4 Baths
8 Guests
1509 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,049/Night
7 Nights - US $7,340
Condo
9.6Exceptional
(96 Reviews)
3 Bedrooms
2 Baths
6 Guests
1155 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $720/Night
7 Nights - US $5,042
Condo
9.6Exceptional
(84 Reviews)
3 Bedrooms
3 Baths
6 Guests
1180 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $832/Night
7 Nights - US $5,827
Condo
9.6Exceptional
(79 Reviews)
3 Bedrooms
3 Baths
6 Guests
1192 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $838/Night
7 Nights - US $5,866
House
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1652 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $297/Night
7 Nights - US $2,076
House
- Key West
- ·
- The Meadows
- 0.07 mi to center
9.4Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
9 Guests
1628 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $405/Night
7 Nights - US $2,835
Condo
9.0Exceptional
(75 Reviews)
4 Bedrooms
3 Baths
8 Guests
1224 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $973/Night
7 Nights - US $6,813
Book a Last Minute Place to Stay in The Meadows
About The Meadows Treehouse Rentals
Explore more than 143 treehouses in The Meadows. 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 The Meadows.
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 The Meadows. 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 The Meadows offer approximately 1266.53 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 The Meadows typically ranges around US $742.
Treehouse Rentals offers a secure and convenient platform to compare and book the best treehouses in The Meadows. 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 The Meadows
| Type | Count |
|---|---|
| Vacation Homes | 88 |
| Holiday Apartments | 9 |
Use these Quick Filters to Find a Vacation Rental in The Meadows
★ 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 The Meadows.
Weather in The Meadows, FL
View the weather forecast for The Meadows before booking your The Meadows 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
Other Places to Stay in The Meadows, FL
Frequently Asked Questions About The Meadows?
What are the top treehouse rentals in The Meadows?
Looking for a place to stay in The Meadows? Explore these highly-rated treehouses for a one-of-a-kind retreat surrounded by nature:
- Waterfront Dock Pool Key West Near Duval
- Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location
- Shady Palms | Historic Charm Private Pool & Effortless Island Style 2BD/2.5BA
- Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
- PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
- The Margaret Suite
- The Crystalmarine Suite – Rustic Luxury on the Sea
- Tropical Heron Hideaway w/Hot Tub + Pool
- Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
- Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
How many treehouses with private pools are available in The Meadows?
Find exceptional treehouses with private pools near The Meadows 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.
- Historic "Old Town" Charm
- Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
- *SOUTHERN STAR @ THE MEADOWS* Private Home & Pool + LAST KEY SERVICES.
- *MODERN IN THE MEADOWS* Modern Home & Pool + Last Key White Glove Service.
What are the top-rated treehouses in The Meadows for family stays?
Searching for a family-friendly treehouse in The Meadows? Discover these top-rated options, each loved by families and groups who have stayed in The Meadows:
- Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Upper Bayview South
- Historic "Old Town" Charm
How many treehouses are available in The Meadows?
Treehouse Rentals, as of 2026, features over 143 unique treehouse, cabins and forest homes in The Meadows. Choose from treetop hideaways, eco-friendly lodges, and off-grid properties, with new options added frequently.
By 2026, Treehouse Rentals has curated over 143 stunning properties in The Meadows, sourced from trusted platforms. Plan your nature-inspired getaway now.
For 2026, Treehouse Rentals provides access to over 143 premier accommodations in The Meadows. Find your ideal escape among the treetops today.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2112 |
| Old Town Vacation Rentals in Key West, Florida | 2007 |
| Meadows Vacation Rentals in Key West, Florida | 101 |
| Midtown Vacation Rentals in Key West, Florida | 41 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4477 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4473 |
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