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

Search 321,000 hotels worldwide.

Get the best price available for your trip.

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


Featured Florida Keys Hotels with Pool

See all 511 Hotels in Florida Keys
The Inn at Key West

The Inn at Key West

3420 N Roosevelt Blvd, Key West
3.5 out of 5.0
4.1 out of 5 (4,564 reviews)
Very nice hotel with shuttle service We enjoyed our brief stay, that was cut short due to Hurricane Irma evacuation. The room was very nicely appointed except for the rock hard pillows. The hotel provided shuttle service to near Mallory Square. A huge plus. Don't forget to tip the driver. The hotel concierge desk provided us with some ...
  9 Sep 2017
The Gates Hotel Key West

The Gates Hotel Key West

3824 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.3 out of 5 (1,063 reviews)
great experience...loved the complimentary rum punch 😁
  21 Nov 2017

£127

£127
Parrot Key Hotel & Resort

Parrot Key Hotel & Resort

2801 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.3 out of 5 (2,946 reviews)
Nice hotel. Close to the water. Nice staff.Pro: Room is large and comfortable. Location is convenient. Staff are nice. It also has complementary shuttle service to downtown if you need transportation. Con: This property seems to be relatively old and is NOT sound-proof. If you're a light sleeper, or you really care about noise level - or ...
  14 Sep 2017
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd, Duck Key
4.0 out of 5.0
4.2 out of 5 (2,102 reviews)
Nice resort with its own beach and 2 pools We love staying at Hawk's Cay. I love that they have heir own little private beach/lagoon area. Main pool is beautiful, but when you want to get away from other people's kids, there is an adult pool as well. It's a little older but still really nice. My only complaint is that is that the menus have ...
  17 Sep 2017
Best Western Key Ambassador Resort Inn

Best Western Key Ambassador Resort Inn

3755 S Roosevelt Blvd, Key West
2.5 out of 5.0
4.0 out of 5 (1,919 reviews)
Nice Hotel!Really Nice hotel and Room, just a little noisy from the airport
  18 Nov 2017

£129

£129
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West
4.0 out of 5.0
4.5 out of 5 (3,089 reviews)
Great HotelGreat Hotel! Has a lot of options for everyone. 2 Beach options, 3 pools, restaurant on/near site and right on Duval street. The rooms had character and were some of the nicest we've been in. Staff was friendly and helpful. Our only negative was the extra fees not included in room rate - (parking, ...
  20 Nov 2017

£157

£157
Holiday Inn Key Largo

Holiday Inn Key Largo

99701 Overseas Hwy, Key Largo
3.0 out of 5.0
3.9 out of 5 (1,160 reviews)
Nice hotel, pool, and tiki bar!The only complaint is there is no elevator and the room was a little musty smelling. Overall it was a nice hotel.
  11 Nov 2017

£102

£102
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West
2.5 out of 5.0
4.1 out of 5 (837 reviews)
Great location.Lovely hotel in the middle of the Old Town. I had a great stay in this hotel. It is also a short walk to the beach.
  23 Nov 2017

£112

£112
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
3.5 out of 5.0
4.3 out of 5 (1,197 reviews)
awesome placeeverything looks new condition, very clean, ac very cold.
  5 Sep 2017

£214

£214
Islander Resort

Islander Resort

82100 Overseas Highway, Islamorada
3.0 out of 5.0
4.2 out of 5 (1,748 reviews)
No clean towels for the second day, internet not good. No paper towel either.
  9 Sep 2017
Map

Recently booked Florida Keys hotels

Amy Slate's Amoray Dive Resort
2.0 out of 5.0
Last booking: 24 minutes ago
The Caribbean Resort
3.5 out of 5.0
Last booking: 38 minutes ago
Holiday Inn Key Largo
3.0 out of 5.0
Last booking: 59 minutes ago
Amara Cay Resort
3.5 out of 5.0
Last booking: 1 hour ago
The Gates Hotel Key West
4.0 out of 5.0
Last booking: 1 hour ago
Southernmost Beach Resort
4.0 out of 5.0
Last booking: 1 hour ago
Pegasus International Hotel
2.5 out of 5.0
Last booking: 3 hours ago
Creekside Inn Islamorada
2.5 out of 5.0
Last booking: 5 hours ago
24 North Hotel Key West
3.5 out of 5.0
Last booking: 5 hours ago

Hotels with Pools in Florida Keys

Whatever time of year you visit the Florida Keys, chances are the weather will be fantastic. Sunshine and balmy temperatures are pretty much par for the course on these islands. And despite the world-class diving, stunning scenery and eco-tourism in Florida Keys, it’s ultimately the warm sunny forecasts that draw in the crowds. This is the Sunshine State, after all. And thanks to its reliably stunning weather, there is no shortage of hotels with pools in Florida Keys designed to make the most of it.

Choosing a Pool Hotel in Florida Keys

Pools come as standard with most accommodation in Florida Keys, whether it’s a relaxing adults-only infinity pool or a kid-friendly family pool. Even some of the budget motels and hostels have a basic outdoor pool and sun terrace. Go for a mid-range hotel or guesthouse and enjoy a pool with loungers, parasols and a pool bar. Upgrade to a luxury resort and you could be treated to anything from a pool in a secluded palm-lined tropical oasis, to one with built-in waterfalls and lined with cabana day beds.

Temperatures can soar in Florida Keys on summer days, so the best place to spend them is at an ocean-view pool with a cooling sea breeze. You can book a pool hotel with sea views in any price bracket, with hotels with infinity pools usually at the top end. The ultimate sea-view hotel pool is a saltwater lagoon, a pool fed directly by the ocean and raises and lowers with the tide. They are unusual, but if you book a hotel with a saltwater lagoon, you’ll find they are superb for snorkelling and paddleboarding.

Sights and Attractions in the Florida Keys

Thanks to the sheer number of hotels with pools available in Florida Keys, you can cherry pick a place to stay that is right on the doorstep of your must-sees. From Key Largo in the north all the way down to Key West, there is a hotel with a pool for every taste and budget.