Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 590,000 properties worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Florida Keys Hotels with a Pool

See all 1,095 Hotels in Florida Keys
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West
4.5 out of 5.0
4.5 out of 5 (3,194 reviews)
Amazing beach vacationIt was the best vacation!!! Our first time in key west and we loved it everyone at the hotel was amazing!! Super clean gorgeous pools and views
 cara Aug 23, 2017

$344

$344
24 North Hotel Key West

24 North Hotel Key West

3820 North Roosevelt Boulevard, Key West
4.5 out of 5.0
4.1 out of 5 (1,116 reviews)
Great pool, friendly staff.A great getaway. Sleek and modern. Live music by the pool.
  Feb 10, 2016

$254

$254
Best Western Key Ambassador Resort Inn

Best Western Key Ambassador Resort Inn

3755 S Roosevelt Blvd, Key West
3.0 out of 5.0
4.0 out of 5 (1,643 reviews)
Great location, clean, friendly staff, great poolVery happy here, we had a lovely break with our 1yr old.
  Aug 27, 2015

$271

$271
The Gates Hotel Key West

The Gates Hotel Key West

3824 N Roosevelt Blvd, Key West
4.5 out of 5.0
4.3 out of 5 (1,120 reviews)
Lovely clean, modern hotelOne of the nicest hotels in Key West.Great rooms, friendly staff, lovely pool. All on all would highly recommend.
 Mark Oct 19, 2015

$254

$254
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
4.0 out of 5.0
4.3 out of 5 (1,221 reviews)
nice hotelGreat location, nice pool, recently remodeled. hhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhhh
 Troy Apr 30, 2017

$321

$321
Parrot Key Hotel & Resort

Parrot Key Hotel & Resort

2801 N Roosevelt Blvd, Key West
4.5 out of 5.0
4.2 out of 5 (2,191 reviews)
A little bit of ParadiseIf this Hotel had access to the beach it would be complete heaven. Its pretty close already. Beautiful private rooms and gorgeous pools. We will surely be back!
 Cara Aug 5, 2013
Silver Palms Inn

Silver Palms Inn

830 Truman Ave, Key West
4.0 out of 5.0
4.4 out of 5 (1,815 reviews)
Nice hotel in historic districtGood parking, good breakfast, convenient to all sites. Felt safe and comfortable. Clean, nice pool, friendly service.
 Gail Feb 1, 2015

$309

$309
Sheraton Suites Key West

Sheraton Suites Key West

2001 S Roosevelt Blvd, Key West
4.0 out of 5.0
4.2 out of 5 (2,078 reviews)
Beautiful hotel for a relaxing vacationEnjoyed our stay!! Lovely room, beautiful pool & friendly, hospitable staff!
  Mar 24, 2017

$299

$299
Fairfield Inn and Suites by Marriott Key West

Fairfield Inn and Suites by Marriott Key West

2400 N Roosevelt Blvd, Key West
3.0 out of 5.0
4.1 out of 5 (1,483 reviews)
Key West at ChristmasNice clean hotel great pool area, friendly and helpful staff. Close to center of town would be a 30 minute walk so required taxi or car. Happy hour in the afternoon like most bars in Key West but snacks at the bar were limited. Good breakfast very polar in the morning.
 Mike Dec 29, 2013
Islander Resort

Islander Resort

82100 Overseas Highway, Islamorada
3.5 out of 5.0
4.2 out of 5 (1,745 reviews)
Nice hotel close to everything. Staff was greatClean rooms beautiful pools and lovely view. Front desk staff went above and beyond to help. Marleen at the front desk was exceptional Located next to the Theater by the Sea, several Marinas located close by.
 Myra  Sep 1, 2017
Hyatt Place Marathon Florida Keys

Hyatt Place Marathon Florida Keys

1996 Overseas Highway, Marathon
3.5 out of 5.0
4.5 out of 5 (1,365 reviews)
brand new 10 day old hotel. beautifulAn excellent hotel in a great spot. Five star in every respect. Hated to check out. Beautiful pool, great location, great staff.
 Jerry Dec 29, 2014

$214

$214
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West
3.0 out of 5.0
4.1 out of 5 (888 reviews)
Great getawayLovely warm pool- beautiful grounds! The staff was very friendly.i loved our stay! The parking may be an issue - not enough- had to keep pumping the meter for on-street parking
 linda Jan 24, 2015

$299

$299
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West
4.5 out of 5.0
4.5 out of 5 (379 reviews)
Good overall. A place with beautiful pools, boats.
  Nov 22, 2017

$305

$305
Fairfield Inn & Suites by Marriott Key West, Keys Collection

Fairfield Inn & Suites by Marriott Key West, Keys Collection

3852 North Roosevelt Boulevard, Key West
3.5 out of 5.0
4.0 out of 5 (920 reviews)
within distance to everythingHotel was great. Worked out well for our trip.Room cleaning could be earlier in the day. 5 pm is late for your room to be cleaned. 2 days we were out all afternoon and did not mind. 2 days it was problem. Great pool and staff great and helpful.
 scott Aug 29, 2016

$279

$279
Lime Tree Bay Resort

Lime Tree Bay Resort

68500 Overseas Hwy, Long Key
4.0 out of 5.0
4.1 out of 5 (581 reviews)
Great waterfront with sunset viewsStayed in one of the canal front units off resort but was within a short walk of main resort. Sometimes challenging to cross the busy street. Clean but could use a little TLC. Also noticed some mold around AC ducts. Right next to busy Rt 1 also so a lot of road noise and could hear people in other ...
 B Mar 5, 2017

$253

$253
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd, Duck Key
4.5 out of 5.0
4.2 out of 5 (1,930 reviews)
Nice hotel but, everything is expensiveLoved laying by the lagoon watching the dolphins. Beautiful views and excellent pools. Don't go if you're looking for a great beach. There really aren't any great beaches in the keys. The lagoon does have sand and is connected to salt water. It's a great place to go if you're just wanting to relax. ...
 D.G Nov 1, 2013
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

3990 S Roosevelt Blvd, Key West
4.0 out of 5.0
4.2 out of 5 (1,998 reviews)
nice pool good staffHave been here twice in four years buffet breakfast is a good deal had lunch and dinner here also food was plentiful and good
  Mar 22, 2014

$278

$278
Marina Del Mar Resort and Marina

Marina Del Mar Resort and Marina

527 Caribbean Drive, Key Largo
2.5 out of 5.0
3.6 out of 5 (1,849 reviews)
Great location with friendly staff and nice pool area. The rooms are clean and the rate was excellent.
  Nov 21, 2017

$179

$179
Holiday Inn Key Largo

Holiday Inn Key Largo

99701 Overseas Hwy, Key Largo
3.5 out of 5.0
3.9 out of 5 (1,184 reviews)
Great placeFriendly informative staff, clean great pool and awesome evening bartender! Great experience beautiful grounds :)
 Jessi Mar 22, 2014

$179

$179
Map

Recently booked Hotels with a Pool in Florida Keys

Anchorage Resort & Yacht Club
3.5 out of 5.0
Last booking: 7 minutes ago
Heron House - Adult Only
4.0 out of 5.0
Last booking: 9 minutes ago
Albury Court Hotel - Key West
3.5 out of 5.0
Last booking: 9 minutes ago
Fairfield Inn and Suites by Marriott Key West
3.0 out of 5.0
Last booking: 4 hours ago
Blackfin Resort and Marina
2.0 out of 5.0
Last booking: 4 hours ago
Southernmost Beach Resort
4.5 out of 5.0
Last booking: 5 hours ago
Best Western Key Ambassador Resort Inn
3.0 out of 5.0
Last booking: 5 hours ago
Holiday Inn Express Hotel & Suites Marathon
2.5 out of 5.0
Last booking: 6 hours ago
Casa Marina, A Waldorf Astoria Resort
4.5 out of 5.0
Last booking: 6 hours ago

Pocket Guide: Hotels with a Pool in Florida Keys

Search for hotels in Florida Keys on Expedia. You can easily find your hotels in Florida Keys using one of the methods below:

  • View our selection of featured hotels in Florida Keys
  • Use the map to find hotels in the Florida Keys neighborhood you prefer
  • Use the filters to see hotels in a specific area of Florida Keys, select a specific theme, brand, or hotel class from basic (1 Star) to luxury hotels (5 Stars) in Florida Keys
  • Enter your travel dates to view the best deals on hotels in Florida Keys - while they last