Find hotels with pools in Meadows, Key West from $187

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Check availability on Meadows Hotels with a Pool

Our top choices for Meadows hotels with a pool

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Meadows
10.0 out of 10, Exceptional, (16)
"Really enjoyed the accommodations. "
United States
Timothy
$390 nightly
The price is $433
Dec 16 - Dec 17
Total with taxes and fees
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Old Town "Eleuthera" • 2BR Waterfront Corner Condo

Old Town "Eleuthera" • 2BR Waterfront Corner Condo
Meadows
10.0 out of 10, Exceptional, (28)
"Kim was a huge help and a great host. Great location. "
United States
James C.
$385 nightly
The price is $428
Dec 14 - Dec 15
Total with taxes and fees
Old Town "Eleuthera" • 2BR Waterfront Corner Condo

The Caroline Suite | 1 bed, 1 bath condo w/shared pool

The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Key West Historic District
9.0 out of 10, Wonderful, (18)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
United States
Sean A.
$584 nightly
The price is $648
Dec 13 - Dec 14
Total with taxes and fees
The Caroline Suite | 1 bed, 1 bath condo w/shared pool

Heron Hideaway

Heron Hideaway
Key West Historic District
$417 nightly
The price is $463
Dec 17 - Dec 18
Total with taxes and fees
Heron Hideaway

"Dominica" Key West 2BR • Dock, Pool, Pet-Friendly

"Dominica" Key West 2BR • Dock, Pool, Pet-Friendly
Meadows
10.0 out of 10, Exceptional, (2)
"Absolutely wonderful. Everyone was so helpful and the property is fantastic. We had the best time. "
United States
Collette B.
$945 nightly
The price is $1,052
Jan 9 - Jan 10, 2026
Total with taxes and fees
"Dominica" Key West 2BR • Dock, Pool, Pet-Friendly

Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations

Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations
2.0 star property
Key West Historic District
$684 nightly
The price is $759
Jan 3 - Jan 4, 2026
Total with taxes and fees
Poolside Hide-Away @ Palm Gardens offered by Rent Key West Vacations

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (114)
"Everything was as advertised! Pool was great to come back to after spending days roaming the streets of Key West. Facilities (kitchen, bathrooms, bedrooms) were all clean and comfortable. Would 100% recommend to anyone wishing to stay."
Canada
Brian M.
$1,746 nightly
The price is $1,939
Jan 2 - Jan 3, 2026
Total with taxes and fees
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

The Elizabeth Suite | 1 bed, 1 bath w/shared pool

The Elizabeth Suite | 1 bed, 1 bath w/shared pool
Key West Historic District
9.2 out of 10, Wonderful, (7)
"Great stay"
United States
Anonymous traveler
$584 nightly
The price is $648
Dec 13 - Dec 14
Total with taxes and fees
The Elizabeth Suite | 1 bed, 1 bath w/shared pool

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1171)
"Will be staying here every single time we visit! "
United States
Rebecca
$183 nightly
The price is $206
Dec 16 - Dec 17
Total with taxes and fees
The Perry Hotel & Marina Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town
8.0 out of 10, Very Good, (1756)
"Loved staying here and would again next time we are in Key West!!"
Canada
David
$166 nightly
The price is $187
Dec 14 - Dec 15
Total with taxes and fees
Blue Flamingo Resort Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Meadows Hotel Reviews

Frequently asked questions

What are some accommodations with pools in Meadows?
Beachside Resort & Residences: Hotel located near Florida Keys Beaches. Features a private beach, an outdoor pool, and 2 restaurants. Blue Flamingo Resort Key West: Hotel located near Florida Keys Beaches. Offers 2 restaurants, 2 outdoor pools, and 2 pool bars. Oceans Edge Key West Resort, Hotel & Marina: Hotel located near Smathers Beach. Provides complimentary bicycles, 6 outdoor pools, and complimentary wireless internet access. Hilton Garden Inn Key West / The Keys Collection: Hotel located near Florida Keys Beaches. Features 2 restaurants, a pool, and complimentary wired internet access. Margaritaville Beach House Key West: Hotel, 13-minute walk from Florida Keys Beaches. Offers a 24-hour fitness center, an outdoor pool, and televisions.
What is there to see and do in Meadows?
Explore places like Duval Street while you're in the area. Enjoy a stroll along the shore at Clarence S. Higgs Memorial Beach Park and South Beach.

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