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

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

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


Featured Florida Keys Hotels with Pool

See all 399 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
4.0 out of 5 (2,065 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 (318 reviews)
Nice hotel within minutes of downtownThe location is perfect because it is within minutes of everything. The staff is great and very professional. My boyfriend was worried he lost his vacation mug, but the staff located it and put it aside for him because they knew who it was for. They even offer a free shuttle service to and from downtown, ...
  12 Oct 2017

£138

£138
Parrot Key Hotel & Resort

Parrot Key Hotel & Resort

2801 N Roosevelt Blvd, Key West
4.0 out of 5.0
4.2 out of 5 (1,154 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

£159

£159
Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd, Duck Key
4.0 out of 5.0
4.1 out of 5 (1,140 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 (646 reviews)
Nice hotel! We especially enjoyed the pool and tiki hut bar.
  3 Sep 2017

£127

£127
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West
4.0 out of 5.0
4.5 out of 5 (1,494 reviews)
Nice place and great locationWe enjoyed our stay. They were very accommodating with our flight in and out. The location was perfect.. close to so many things.
  12 Oct 2017

£210

£210
Holiday Inn Key Largo

Holiday Inn Key Largo

99701 Overseas Hwy, Key Largo
3.0 out of 5.0
3.8 out of 5 (372 reviews)
Very nice hotel with luxuryDuring our stay at the keys, we spend some time in this very nice hotel with all kinds of luxury. A very good place to stay when you look for a hotel.
  25 Aug 2017

£107

£107
The Southernmost Inn

The Southernmost Inn

525 United Street, Key West
2.5 out of 5.0
4.0 out of 5 (332 reviews)
Right off Duval Dan was an amazing innkeeper. Helped with our excursion coordination and gave us an excellent breakfast recommendation. Pools and hot tub were great. Within walking distance of all the fun of Duval Street.
  17 Oct 2017

£97

£97
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
3.5 out of 5.0
4.2 out of 5 (477 reviews)
awesome placeeverything looks new condition, very clean, ac very cold.
  5 Sep 2017

£140

£140
Islander Resort, a Guy Harvey Outpost

Islander Resort, a Guy Harvey Outpost

82100 Overseas Highway, Islamorada
3.0 out of 5.0
4.2 out of 5 (673 reviews)
No clean towels for the second day, internet not good. No paper towel either.
  9 Sep 2017
Map

Recently booked Florida Keys hotels

Parmer's Resort
2.5 out of 5.0
Last booking: 11 minutes ago
Sands of Islamorada
2.5 out of 5.0
Last booking: 24 minutes ago
Southernmost Beach Resort
4.0 out of 5.0
Last booking: 32 minutes ago
Fairfield Inn and Suites Key West
2.5 out of 5.0
Last booking: 35 minutes ago
Key Lime Inn - Key West
3.0 out of 5.0
Last booking: 41 minutes ago
Playa Largo Resort & Spa, Autograph Collection
3.5 out of 5.0
Last booking: 43 minutes ago
Duval Inn
3.0 out of 5.0
Last booking: 49 minutes ago
Southwinds Motel
2.0 out of 5.0
Last booking: 1 hour ago
La Concha Hotel & Spa
3.5 out of 5.0
Last booking: 1 hour 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.