The Meadows Vacation Rentals & Ski-in/Ski-out Homes
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
Oceanfront
Parking
Pool
Ocean View
US $511/Night
7 Nights - US $3,574
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Parking
- Pool
View
Air Conditioner
US $337/Night
7 Nights - US $2,360
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 $267/Night
7 Nights - US $1,872
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 Places to Stay in The Meadows
Over 134+ Luxury Places to Stay 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
9.8Exceptional
(147 Reviews)
5 Bedrooms
4 Baths
12 Guests
3605 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,893/Night
7 Nights - US $13,250
House
4 Bedrooms
3 Baths
10 Guests
2895.49 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $1,832/Night
7 Nights - US $12,826
Top-Rated Vacation Rentals with a Pool in The Meadows
Over 109+ Top-Rated Vacation Rentals 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 $407/Night
7 Nights - US $2,849
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)
2 Bedrooms
1 Bath
4 Guests
455 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $505/Night
7 Nights - US $3,536
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 $164/Night
7 Nights - US $1,148
House
9.8Exceptional
(153 Reviews)
4 Bedrooms
3 Baths
10 Guests
2898 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,150/Night
7 Nights - US $8,050
House
9.8Exceptional
(146 Reviews)
3 Bedrooms
3 Baths
8 Guests
2849 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,428/Night
7 Nights - US $9,996
House
9.8Exceptional
(134 Reviews)
4 Bedrooms
3 Baths
10 Guests
2898 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,258/Night
7 Nights - US $8,807
Condo
9.8Exceptional
(133 Reviews)
4 Bedrooms
4 Baths
8 Guests
1498 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,173/Night
7 Nights - US $8,209
Pet-Friendly Vacation Rentals in The Meadows
Over 53+ Pet-Friendly Vacation Rentals 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 $173/Night
7 Nights - US $1,214
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 $182/Night
7 Nights - US $1,274
House
9.2Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
8 Guests
1345.49 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $904/Night
7 Nights - US $6,325
Condo
9.8Exceptional
(38 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $484/Night
7 Nights - US $3,387
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 $173/Night
7 Nights - US $1,210
Condo
9.6Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $622/Night
7 Nights - US $4,354
Large Vacation Homes & Villas in The Meadows
Over 17+ Large Vacation Homes & Villas in or Near The Meadows
House
9.8Exceptional
(91 Reviews)
4 Bedrooms
3 Baths
10 Guests
2829 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,632/Night
7 Nights - US $11,425
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
Condo
9.8Exceptional
(31 Reviews)
4 Bedrooms
4 Baths
16 Guests
2400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $950/Night
7 Nights - US $6,650
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
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 $915/Night
7 Nights - US $6,408
Condo
9.6Exceptional
(36 Reviews)
4 Bedrooms
4 Baths
16 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $893/Night
7 Nights - US $6,254
Condo
9.6Exceptional
(33 Reviews)
4 Bedrooms
4 Baths
15 Guests
2400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $838/Night
7 Nights - US $5,864
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 Vacation Homes in The Meadows
Over 16+ Wheelchair Accessible Vacation 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 $584/Night
7 Nights - US $4,086
Condo
9.6Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $647/Night
7 Nights - US $4,528
Condo
9.4Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $556/Night
7 Nights - US $3,895
Condo
9.2Exceptional
(109 Reviews)
2 Bedrooms
2 Baths
8 Guests
1215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $495/Night
7 Nights - US $3,465
Condo
9.2Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $453/Night
7 Nights - US $3,173
Condo
9.0Exceptional
(107 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $378/Night
7 Nights - US $2,644
Condo
9.8Exceptional
(83 Reviews)
4 Bedrooms
4 Baths
8 Guests
1453 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,190/Night
7 Nights - US $8,328
Condo
9.6Exceptional
(109 Reviews)
4 Bedrooms
4 Baths
8 Guests
1454 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,133/Night
7 Nights - US $7,929
Condo
9.6Exceptional
(100 Reviews)
4 Bedrooms
4 Baths
8 Guests
1509 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,135/Night
7 Nights - US $7,944
The Meadows Resorts and Airbnb Homes Under $200
Over 7+ The Meadows Resorts and Airbnb 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 $164/Night
7 Nights - US $1,150
House
- Key West
- ·
- The Meadows
- 0.12 mi to center
9.0Exceptional
(1006 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $182/Night
7 Nights - US $1,275
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
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
House
- Key West
- ·
- The Meadows
- 0.06 mi to center
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $192/Night
7 Nights - US $1,342
Condo
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $137/Night
7 Nights - US $958
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 Vacation Homes in The Meadows
Over 43+ Instantly Bookable Vacation Homes in or Near The Meadows
Cottage
- Key West
- ·
- The Meadows
- 0.07 mi to center
9.8Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1320 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $577/Night
7 Nights - US $4,038
Condo
9.6Exceptional
(96 Reviews)
3 Bedrooms
2 Baths
6 Guests
1155 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $872/Night
7 Nights - US $6,105
Condo
9.6Exceptional
(84 Reviews)
3 Bedrooms
3 Baths
6 Guests
1180 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $993/Night
7 Nights - US $6,954
Condo
9.6Exceptional
(79 Reviews)
3 Bedrooms
3 Baths
6 Guests
1192 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $968/Night
7 Nights - US $6,778
Condo
9.6Exceptional
(64 Reviews)
4 Bedrooms
3 Baths
8 Guests
1237 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,085/Night
7 Nights - US $7,596
House
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1652 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $305/Night
7 Nights - US $2,135
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 $406/Night
7 Nights - US $2,844
Condo
9.0Exceptional
(75 Reviews)
4 Bedrooms
3 Baths
8 Guests
1224 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $1,015/Night
7 Nights - US $7,108
House
- Key West
- ·
- The Meadows
- 0.11 mi to center
4 Bedrooms
3 Baths
10 Guests
2500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $631/Night
7 Nights - US $4,416
Book a Last Minute Place to Stay in The Meadows
About The Meadows Vacation Rentals
Explore over 143 vacation rentals in The Meadows 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 The Meadows 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 The Meadows. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in The Meadows tailored to your preferences. On average, these rentals offer 1267.37 ft² of space, and are priced at an average of US $755 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in The Meadows 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 The Meadows
| Type | Count |
|---|---|
| Vacation Homes | 88 |
| Holiday Apartments | 9 |
| Unique Vacation Rentals | 2 |
| B&B | 1 |
| Cottages | 1 |
Use these Quick Filters to Find a Vacation Rental in The Meadows
★ Pro Tip: Discover Your Ideal Vacation Rental in The Meadows 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 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
Complexes around The Meadows, FL
Frequently Asked Questions About The Meadows?
What are the top vacation rentals in The Meadows?
When organizing your trip to The Meadows, 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 The Meadows. Peruse our collection of highly-rated properties and secure your reservation today.
- Waterfront Dock Pool Key West Near Duval
- Eliza Street Retreat, 2 bedroom, 2 bathrm, + loft, private pool, great location
- Shady Palms - Stay In Comfort- May - Aug 10% OFF - 2BD/2.5Bath - Private Pool
- 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
- Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
How many vacation rentals have private pools in The Meadows?
Uncover 26 vacation rentals boasting private pools near The Meadows. Explore top-rated RBO homes offering access to a swimming pool:
- Historic "Old Town" Charm
- *SOUTHERN STAR @ THE MEADOWS* Private Home & Pool + LAST KEY SERVICES.
- *MODERN IN THE MEADOWS @ The Meadows* Private Home & Pool + LAST KEY SERVICES…
- Boomerang Boathouse
Which vacation homes or resorts in The Meadows are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in The Meadows. Enjoy great views, locations and save money with SunSki Resorts.™
- Bright and Comfortable 3 bedroom/2.5 bath Classic Conch in the Meadows
- Upper Bayview South
- Historic "Old Town" Charm
How many SunSkiResorts vacation rentals or resorts are available in The Meadows?
Discover the ideal vacation rental in The Meadows with SunSki Resorts™. We provide an extensive selection of over 143 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to The Meadows.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2053 |
| Old Town Vacation Rentals in Key West, Florida | 1975 |
| Meadows Vacation Rentals in Key West, Florida | 102 |
| 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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