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Hotels with a Pool in Key West
1. Hampton Inn Key West FL
Hampton Inn Key West FLKey West
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
$110
$124 total
includes taxes & fees
Sep 23 - Sep 24
2. Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic HomesOld Town Key West
- Outdoor pool
- Near the beach
$89
$168 total
includes taxes & fees
Sep 20 - Sep 21
$95
$128 total
includes taxes & fees
Sep 20 - Sep 21
4. Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key WestKey West
- Outdoor pool
- Near the beach
- Hot tub
$183
$251 total
includes taxes & fees
Oct 4 - Oct 5
$229
$313 total
includes taxes & fees
Sep 20 - Sep 21
6. Havana Cabana at Key West
Havana Cabana at Key WestNew Town
- Outdoor pool
- Poolside bar
- Pool loungers
- Hot tub
$119
$197 total
includes taxes & fees
Oct 4 - Oct 5
7. Beachside Resort & Residences
Beachside Resort & ResidencesKey West
- Outdoor pool
- Poolside bar
- Pool loungers
- On private beach
- Hot tub
$100
$208 total
includes taxes & fees
Sep 20 - Sep 21
8. Blue Flamingo Resort Key West
Blue Flamingo Resort Key WestNew Town
- 2 outdoor pools
- 2 poolside bars
- Pool loungers
- Hot tub
$110
$180 total
includes taxes & fees
Sep 20 - Sep 21
9. DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
$103
$150 total
includes taxes & fees
Sep 27 - Sep 28
10. Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Beach House, Key WestKey West
- Outdoor pool
- Hot tub
$186
$255 total
includes taxes & fees
Oct 7 - Oct 8
$90
$111 total
includes taxes & fees
Sep 21 - Sep 22
$159
$207 total
includes taxes & fees
Sep 19 - Sep 20
$109
$148 total
includes taxes & fees
Sep 20 - Sep 21
14. Pier House Resort & Spa
Pier House Resort & SpaKey West Historic District
- Outdoor pool
- Poolside bar
- Pool loungers
- On private beach
- Hot tub
$246
$346 total
includes taxes & fees
Sep 28 - Sep 29
15. Ibis Bay Beach Resort
Ibis Bay Beach ResortNorthside Resort
- Outdoor pool
- Poolside bar
- Pool loungers
- On private beach
$101
$146 total
includes taxes & fees
Sep 20 - Sep 21
16. The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key WestStock Island
- 2 outdoor pools
- 2 poolside bars
- Pool loungers
$114
$189 total
includes taxes & fees
Sep 20 - Sep 21
17. Parrot Key Hotel & Villas
Parrot Key Hotel & VillasNorthside Resort
- 4 outdoor pools
- Poolside bar
- Pool loungers
$124
$197 total
includes taxes & fees
Sep 24 - Sep 25
18. Ocean Key Resort - A Noble House Resort
Ocean Key Resort - A Noble House ResortKey West Historic District
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
- Full-service spa
$259
$369 total
includes taxes & fees
Sep 29 - Sep 30
19. Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaKey West Historic District
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
- Full-service spa
$226
$324 total
includes taxes & fees
Oct 5 - Oct 6
20. Almond Tree Inn Hotel - Adults Only
Almond Tree Inn Hotel - Adults OnlyOld Town Key West
- Outdoor pool
- Poolside bar
- Pool loungers
- Near the beach
- Hot tub
$193
$217 total
includes taxes & fees
Sep 30 - Oct 1
Hotels with pools and free breakfast in Key West
$110
$124 total
includes taxes & fees
Sep 23 - Sep 24
$89
$168 total
includes taxes & fees
Sep 20 - Sep 21
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
$103
$150 total
includes taxes & fees
Sep 27 - Sep 28
$101
$146 total
includes taxes & fees
Sep 20 - Sep 21
$110
$180 total
includes taxes & fees
Sep 20 - Sep 21
$119
$197 total
includes taxes & fees
Oct 4 - Oct 5
$124
$197 total
includes taxes & fees
Sep 24 - Sep 25
$193
$217 total
includes taxes & fees
Sep 30 - Oct 1
$110
$174 total
includes taxes & fees
Oct 1 - Oct 2
4-star hotels with pools in Key West
Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaKey West Historic District
$226
$324 total
includes taxes & fees
Oct 5 - Oct 6
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key WestKey West
$103
$150 total
includes taxes & fees
Sep 27 - Sep 28
Ocean Key Resort - A Noble House Resort
Ocean Key Resort - A Noble House ResortKey West Historic District
$259
$369 total
includes taxes & fees
Sep 29 - Sep 30
$189
$276 total
includes taxes & fees
Sep 27 - Sep 28
$160
$253 total
includes taxes & fees
Sep 28 - Sep 29
$124
$197 total
includes taxes & fees
Sep 24 - Sep 25
$259
$331 total
includes taxes & fees
Sep 20 - Sep 21
The Reach Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by HiltonOld Town Key West
$178
$267 total
includes taxes & fees
Sep 29 - Sep 30
La Concha Key West, Autograph Collection
La Concha Key West, Autograph CollectionKey West Historic District
$161
$215 total
includes taxes & fees
Oct 1 - Oct 2
Casa Marina Key West, Curio Collection by Hilton
Casa Marina Key West, Curio Collection by HiltonOld Town Key West
$220
$315 total
includes taxes & fees
Sep 27 - Sep 28
Hotels with pools and hot tubs in Key West
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key WestKey West
$183
$251 total
includes taxes & fees
Oct 4 - Oct 5
$100
$208 total
includes taxes & fees
Sep 20 - Sep 21
$193
$217 total
includes taxes & fees
Sep 30 - Oct 1
$110
$180 total
includes taxes & fees
Sep 20 - Sep 21
$186
$255 total
includes taxes & fees
Oct 7 - Oct 8
$119
$197 total
includes taxes & fees
Oct 4 - Oct 5
$110
$174 total
includes taxes & fees
Oct 1 - Oct 2
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys CollectionNew Town
$105
$146 total
includes taxes & fees
Oct 4 - Oct 5
$187
$210 total
includes taxes & fees
Sep 23 - Sep 24
Top neighborhoods in Key West
Old Town Key West
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Photo by Ronaldo Esteves
New Town
New Town gives you a quieter slice of Key West living away from the tourist crowds. This peaceful residential area offers wide streets for strolling and a glimpse into authentic island life. Nearby Smathers Beach and the Key West Tropical Forest provide natural escapes when you need a break from the bustle. Budget-friendly chain hotels and vacation rentals make this area wallet-friendly for longer stays. Cuban-American eateries and family restaurants offer affordable meals, while shopping plazas with grocery stores help you feel right at home. A car is handy, but free parking is plentiful throughout the neighborhood.
Downtown Key West
Downtown Key West dazzles with its historic charm and non-stop energy. Wander Duval Street's lively scene, visit Hemingway's famous six-toed cat sanctuary, or catch the sunset celebration at Mallory Square where fire-breathers and musicians perform against stunning Gulf backdrops. The neighborhood's Victorian mansions with gingerbread trim and weathered coral stone churches create a unique tropical atmosphere. The area serves up fresh seafood from casual waterfront joints to upscale restaurants. Most attractions sit within a walkable six-block radius, though you can hop on the Conch Tour Train when your feet need a break. Boutique hotels and historic inns with tropical courtyards offer charming places to crash after experiencing the legendary bar scene.
Key West Historic District
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
Uptown - Upper Duval
Key West's Uptown - Upper Duval neighborhood has a host of places to visit such as Duval Street and Florida Keys Beaches.
Top landmarks in Key West
Duval Street
9.2/10 (20,928 reviews)
If you want to give your credit card some exercise, head out to Duval Street, a popular place for shoppers in Key West Historic District. Splash some more cash at Mallory Dock and We Cycle Key West.
Southernmost Point
8.8/10 (17,214 reviews)
If you're planning a bit of sightseeing head to Southernmost Point— just one of the monuments in Old Town Key West. Why not take a stroll along the beaches and watch the sunset while you're here?
Mallory Square
9.2/10 (15,939 reviews)
Mallory Square is worth passing through for a few pics when in Key West Historic District. Why not take a stroll along the beaches and watch the sunset while you're here?
Smathers Beach
8.4/10 (8,320 reviews)
Whether you want to collect beach glass or watch the sunset, Smathers Beach is a spot you might want to check out, located 1.7 mi (2.8 km) from central Key West. If you want to continue walking by the waves, head to Clarence S. Higgs Memorial Beach Park located nearby.
Ernest Hemingway Home and Museum
9.2/10 (8,543 reviews)
Ernest Hemingway Home and Museum is just one of the attractions in Old Town Key West, Key West so you might want to stop by during your trip. Why not take a stroll along the beaches and watch the sunset while you're here? If you want to experience more of the culture Key West has to offer, head to Key West Lighthouse and Keeper's Quarters Museum, Duval Street, and Key West Butterfly and Nature Conservatory.
Fort Zachary Taylor Historic State Park
9.0/10 (4,544 reviews)
Fort Zachary Taylor Historic State Park is 0.6 mi (1 km) from central Key West, why not stop by during your stay. Why not take a stroll along the beaches and watch the sunset while you're here?
South Beach
8.4/10 (5,461 reviews)
If being by the water is a major draw, South Beach is a spot you might want to check out, located 0.7 mi (1.1 km) from central Key West. Catch the sunset by the shore at Simonton Beach, just a short walk away.
About the destination
Visitors speak favorably about all that Key West has to offer, including its seaside, live music, bars, and festivals. Activities like biking give you a chance to enjoy the outdoors while you're in town. Beachcombers can spend the day at Florida Keys Beaches when the weather is nice. While you're here, make time to enjoy other sights such as Duval Street.