Hotels with a Pool in Florida Keys
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Florida Keys Hotels with Pool

Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Free Cancellation
$253 nightly
The price is $285 total per night
$285 total
Dec 18 - Dec 19
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with concierge services, dry cleaning/laundry, and luggage storage. Other amenities at this beach hotel include conference space, a 24-hour business center, and coffee/tea in a common area.

Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$175 nightly
The price is $197 total per night
$197 total
Dec 18 - Dec 19
Total with taxes and fees
Blue Flamingo Resort Key West features 2 outdoor pools, karaoke, and a 24-hour gym. If you drive, self parking is USD 15.00 per night, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with luggage storage and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this family-friendly hotel include free WiFi in public areas, a hot tub, and meeting rooms.

Hampton Inn Key West FL
3755 S Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $280 total per night
$280 total
Dec 18 - Dec 19
Total with taxes and fees
At Hampton Inn Key West FL, guests enjoy features like an outdoor pool, a 24-hour gym, and free WiFi in public areas. Self parking is available for USD 15 per day. The front desk is staffed 24/7 to help with luggage storage, concierge services, and dry cleaning/laundry. Additional amenities include coffee/tea in a common area, express check-out, and free newspapers.
Pool
Breakfast included

Amara Cay Resort
80001 Overseas Hwy Islamorada FL
$228 nightly
The price is $257 total per night
$257 total
Dec 18 - Dec 19
Total with taxes and fees
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a gym. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include a meeting room, a terrace, and laundry facilities.

Parrot Key Hotel & Villas
2801 N Roosevelt Blvd Key West FL
$215 nightly
The price is $242 total per night
$242 total
Dec 18 - Dec 19
Total with taxes and fees
Guests staying at Parrot Key Hotel & Villas enjoy access to 4 outdoor pools, a gym, and free WiFi in public areas. Valet parking is available for USD 32.25 per day, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and dry cleaning/laundry. Other amenities at this beach hotel include a business center, a terrace, and a garden.
Pool
Pet friendly

Silver Palms Inn
830 Truman Ave Key West FL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $235 total per night
$235 total
Dec 18 - Dec 19
Total with taxes and fees
Guests staying at Silver Palms Inn enjoy an outdoor pool, free WiFi in public areas, and a vending machine. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include an ATM and a TV in a common area.
Pool
Breakfast included

Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
At Margaritaville Beach House Key West, guests enjoy an outdoor pool, a 24-hour gym, and a hot tub. You can take advantage of free parking, along with an airport shuttle (available 24 hours). The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. Other amenities at this beach hotel include conference space, a 24-hour business center, and a computer station.
Pool
Hot Tub

Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd Key West FL
$174 nightly
The price is $196 total per night
$196 total
Dec 18 - Dec 19
Total with taxes and fees
Guests of Fairfield Inn and Suites by Marriott Key West have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, self parking is USD 11.25 per day, and there's also a beach shuttle. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a computer station.

Islander Resort
82100 Overseas Highway Islamorada FL
Free Cancellation
Reserve now, pay when you stay
$262 nightly
The price is $294 total per night
$294 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
Guests of Islander Resort have access to a private beach, 2 outdoor pools, and a 24-hour gym. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, dry cleaning/laundry, and luggage storage. Other amenities at this beach hotel include free WiFi in public areas, meeting rooms, and a conference center.

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
1996 Overseas Highway Marathon FL
Free Cancellation
Reserve now, pay when you stay
$232 nightly
The price is $262 total per night
$262 total
Dec 18 - Dec 19
Total with taxes and fees
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton features a marina, a full-service spa, and 4 outdoor pools. Self parking is offered for USD 21.50 per day. The 24-hour front desk has staff standing by to help with securing valuables, luggage storage, and concierge services. Other amenities at this beach resort include a 24-hour gym, a steam room, and free WiFi in public areas.
Pool
Spa

The Southernmost Inn - Adults Only
525 United Street Key West FL
$189 nightly
The price is $213 total per night
$213 total
Dec 18 - Dec 19
Total with taxes and fees
Guests of The Southernmost Inn - Adults Only enjoy features like 2 outdoor pools, a hot tub, and coffee in a common area. Self parking is available for USD 32.25 per day. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Other amenities at this adults-only hotel include a microwave in a common area, express check-out, and a terrace.

Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue Key West FL
$236 nightly
The price is $265 total per night
$265 total
Dec 18 - Dec 19
Total with taxes and fees
Guests of Oceans Edge Key West Resort, Hotel & Marina have access to a marina, 6 outdoor pools, and a 24-hour gym. If you drive, self parking is USD 32.63 per night, and there's also an area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this luxury hotel include free WiFi in public areas, meeting rooms, and free use of bicycles.
Pool
Pet friendly

Fairfield Inn & Suites by Marriott Key West at the Keys Collection
3852 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $201 total per night
$201 total
Dec 18 - Dec 19
Total with taxes and fees
At Fairfield by Marriott Inn & Suites Key West at The Keys Collection, guests enjoy an outdoor pool, a gym, and free WiFi in public areas. Self parking is offered for USD 14.00 per day. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include meeting rooms, a 24-hour business center, and coffee/tea in a common area.

Lime Tree Bay Resort
68500 Overseas Hwy Long Key FL
$165 nightly
The price is $186 total per night
$186 total
Dec 18 - Dec 19
Total with taxes and fees
At Lime Tree Bay Resort, guests have access to a private beach, 3 outdoor pools, and free WiFi in public areas. If you drive, take advantage of free parking. The front desk has multilingual staff that can help with tours/tickets and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach resort include an outdoor tennis court, coffee/tea in a common area, and free use of bicycles.

Hawks Cay Resort
61 Hawks Cay Blvd Marathon FL
$272 nightly
The price is $305 total per night
$305 total
Dec 18 - Dec 19
Total with taxes and fees
Hawks Cay Resort features a private beach, a marina, and a full-service spa. Parking is available for USD 28.13 per day (USD 45.00 per day for valet parking), and there's also limo/town car service. The 24-hour front desk has multilingual staff ready to assist with securing valuables and concierge services. Other amenities at this beach hotel include 5 outdoor pools, a children's pool, and a gym.
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.
Florida Keys hotels essential information
Accommodation | 8,415 hotels |
|---|---|
Lowest Price | $186 |
Highest Price | $305 |
Popular hotels | Southernmost Beach Resort and Guesthouses, Blue Flamingo Resort Key West, Hampton Inn Key West FL, Amara Cay Resort, Parrot Key Hotel & Villas, Silver Palms Inn, Margaritaville Beach House Key West, Fairfield Inn and Suites by Marriott Key West, Islander Resort, Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton, The Southernmost Inn - Adults Only, Oceans Edge Key West Resort, Hotel & Marina, Fairfield Inn & Suites by Marriott Key West at the Keys Collection, Lime Tree Bay Resort, Hawks Cay Resort |
Recent Hotels with Pool Reviews

Lime Tree Bay Resort
5/5 Excellent
"Just the best!"
A verified traveler stayed at Lime Tree Bay Resort
Posted 2 days ago


