Meadows Vacation Rentals & Ski-in/Ski-out Homes
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
Oceanfront
Parking
Pool
Ocean View
US $524/Night
7 Nights - US $3,670
New
Apartment
- Key West
- ·
- The Meadows
- 0.12 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
602.78 ft²
- Parking
- Pool
Balcony/Terrace
View
US $405/Night
7 Nights - US $2,835
Bed & Breakfast
- Key West
- ·
- The Meadows
- 0.12 mi to center
9.2Exceptional
(1047 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 $307/Night
7 Nights - US $2,146
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
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1283 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $437/Night
7 Nights - US $3,061
Apartment
10.0Exceptional
(4 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 $398/Night
7 Nights - US $2,788
Luxury Places to Stay in Meadows
Over 135+ Luxury Places to Stay in or Near 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 $2,100/Night
7 Nights - US $14,700
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 Vacation Rentals with a Pool in Meadows
Over 110+ Top-Rated Vacation Rentals with a Pool in or Near Meadows
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1642 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $253/Night
7 Nights - US $1,771
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 $344/Night
7 Nights - US $2,405
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 $340/Night
7 Nights - US $2,383
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
1800 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $887/Night
7 Nights - US $6,208
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 $1,140
House
9.8Exceptional
(156 Reviews)
4 Bedrooms
3 Baths
10 Guests
2898 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,095/Night
7 Nights - US $7,667
House
9.8Exceptional
(147 Reviews)
5 Bedrooms
4 Baths
12 Guests
3605 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,167/Night
7 Nights - US $8,169
House
9.8Exceptional
(137 Reviews)
4 Bedrooms
3 Baths
10 Guests
2898 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $904/Night
7 Nights - US $6,328
Condo
9.8Exceptional
(135 Reviews)
4 Bedrooms
4 Baths
8 Guests
1498 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $746/Night
7 Nights - US $5,222
Pet-Friendly Vacation Rentals in Meadows
Over 56+ Pet-Friendly Vacation Rentals in or Near 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 $1,203
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
- Key West
- ·
- The Meadows
- 0.11 mi to center
9.8Exceptional
(125 Reviews)
1 Bedroom
1 Bath
4 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $177/Night
7 Nights - US $1,239
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
Condo
9.8Exceptional
(39 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $393/Night
7 Nights - US $2,749
Condo
9.8Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
8 Guests
1350 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $711/Night
7 Nights - US $4,978
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 $328/Night
7 Nights - US $2,299
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 $174/Night
7 Nights - US $1,218
Condo
9.6Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $577/Night
7 Nights - US $4,041
Large Vacation Homes & Villas in Meadows
Over 16+ Large Vacation Homes & Villas in or Near Meadows
House
9.8Exceptional
(92 Reviews)
4 Bedrooms
3 Baths
10 Guests
2829 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $973/Night
7 Nights - US $6,813
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 $694/Night
7 Nights - US $4,860
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
(15 Reviews)
5 Bedrooms
4 Baths
12 Guests
3417 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,036/Night
7 Nights - US $7,252
Condo
9.6Exceptional
(42 Reviews)
4 Bedrooms
4 Baths
16 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $934/Night
7 Nights - US $6,541
Condo
9.6Exceptional
(38 Reviews)
4 Bedrooms
4 Baths
16 Guests
2000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $581/Night
7 Nights - US $4,066
Condo
9.6Exceptional
(35 Reviews)
4 Bedrooms
4 Baths
15 Guests
2400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $581/Night
7 Nights - US $4,066
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 $1,301/Night
7 Nights - US $9,105
Wheelchair Accessible Vacation Homes in Meadows
Over 18+ Wheelchair Accessible Vacation Homes in or Near Meadows
Condo
9.6Exceptional
(73 Reviews)
2 Bedrooms
1 Bath
4 Guests
693 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $412/Night
7 Nights - US $2,881
Condo
9.6Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $656/Night
7 Nights - US $4,589
Condo
9.4Exceptional
(152 Reviews)
2 Bedrooms
2 Baths
8 Guests
1215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $626/Night
7 Nights - US $4,383
Condo
9.4Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $421/Night
7 Nights - US $2,944
Condo
9.4Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $368/Night
7 Nights - US $2,574
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
9.0Exceptional
(108 Reviews)
2 Bedrooms
2 Baths
6 Guests
1215 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $495/Night
7 Nights - US $3,465
New
Condo
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $404/Night
7 Nights - US $2,830
Condo
9.8Exceptional
(111 Reviews)
4 Bedrooms
4 Baths
8 Guests
1454 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $739/Night
7 Nights - US $5,173
Meadows Resorts and Airbnb Homes Under $200
Over 7+ 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 $1,147
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 $151/Night
7 Nights - US $1,059
Condo
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $191/Night
7 Nights - US $1,339
House
- Key West
- ·
- The Meadows
- 0.06 mi to center
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $190/Night
7 Nights - US $1,328
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
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 $197/Night
7 Nights - US $1,377
Instantly Bookable Vacation Homes in Meadows
Over 44+ Instantly Bookable Vacation Homes in or Near Meadows
House
- Key West
- ·
- The Meadows
- 0.12 mi to center
9.2Exceptional
(74 Reviews)
1 Bedroom
1 Bath
4 Guests
460 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $492/Night
7 Nights - US $3,446
Boat Rental
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
Bedding/Linens- Security/Safety
US $824/Night
7 Nights - US $5,770
Condo
9.8Exceptional
(84 Reviews)
4 Bedrooms
4 Baths
8 Guests
1453 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $906/Night
7 Nights - US $6,344
Condo
9.6Exceptional
(101 Reviews)
4 Bedrooms
4 Baths
8 Guests
1509 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $885/Night
7 Nights - US $6,193
Condo
9.6Exceptional
(97 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 $724/Night
7 Nights - US $5,065
Condo
9.6Exceptional
(80 Reviews)
3 Bedrooms
3 Baths
6 Guests
1192 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $728/Night
7 Nights - US $5,096
Condo
9.6Exceptional
(67 Reviews)
4 Bedrooms
3 Baths
8 Guests
1237 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $857/Night
7 Nights - US $6,001
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
Book a Last Minute Place to Stay in Meadows
About Meadows Vacation Rentals
Explore over 144 vacation rentals in 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 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 Meadows. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Meadows tailored to your preferences. On average, these rentals offer 1266.1 ft² of space, and are priced at an average of US $710 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Meadows at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Meadows
| Type | Count |
|---|---|
| Vacation Homes | 89 |
| Holiday Apartments | 9 |
| Unique Vacation Rentals | 2 |
| B&B | 1 |
Use these Quick Filters to Find a Vacation Rental in Meadows
★ Pro Tip: Discover Your Ideal Vacation Rental in 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 Meadows, FL
View the weather forecast for Meadows before booking your 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 Meadows, FL
Complexes around Meadows, FL
Frequently Asked Questions About Meadows?
What are the top vacation rentals in Meadows?
When organizing your trip to 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 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 | Historic Charm Private Pool & Effortless Island Style 2BD/2.5BA
- Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
- The Margaret Suite
- PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
- 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
- Turtle Nest Condo - Pool - 2nd Floor
How many vacation rentals have private pools in Meadows?
Uncover 29 vacation rentals boasting private pools near Meadows. Explore top-rated RBO homes offering access to a swimming pool:
- WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/Pool!
- Historic "Old Town" Charm
- Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
- *SOUTHERN STAR @ THE MEADOWS* Home & Pool + Last Key White Glove Service.
Which vacation homes or resorts in Meadows are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in 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
- WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/Pool!
How many SunSkiResorts vacation rentals or resorts are available in Meadows?
Discover the ideal vacation rental in Meadows with SunSki Resorts™. We provide an extensive selection of over 144 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Meadows.
Nearby Neighborhood (3)
| Neighborhood | Property Count |
|---|---|
| Old Town Vacation Rentals in Key West, Florida | 2050 |
| The Meadows Vacation Rentals in Key West, Florida | 103 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4473 |
Map
