The Best Florida Keys Hotels with Pools from $114 - Hotels with indoor pools in Florida Keys

A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check availability on Florida Keys Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Florida Keys hotels with a pool

A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.

A beach with palm trees and lounge chairs.

A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.

1. Chesapeake Beach Resort

Matecumbe

Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.

$188 nightly

$212 total

Oct 5 - Oct 6

Total with taxes and fees

A pool area with a view of the ocean, surrounded by palm trees and a clear sky.

A beach with palm trees, lounge chairs, and a view of the ocean.

A covered outdoor area with a view of a beach and palm trees.

A wooden dock with a boat docked at the pier, a thatched umbrella, and calm water.

2. Rock Reef Resort

Rock Harbor

Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views.

$101 nightly

$114 total

Oct 4 - Oct 5

Total with taxes and fees

A blue chair with a sign reading "CaptainPips.com" and a website address.

A waterfront dock with boats and a sunset.

A room with a wooden table and chairs, a sliding glass door leading to a balcony, and a blue cooler on the floor.

A beach with a wooden pier, palm trees, and a clear blue sky.

3. Captain Pips Marina & Hideaway

Marathon

Dive into poolside paradise with water activities galore at this Florida Keys getaway.

$135 nightly

$152 total

Oct 3 - Oct 4

Total with taxes and fees

A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.

A couple holding hands in a tropical setting with palm trees and greenery.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

4. Blue Flamingo Resort Key West

New Town

Float in paradise at two scenic pools with cabanas, surrounded by stunning sunset views and tropical relaxation.

$168 nightly

$189 total

Oct 4 - Oct 5

Total with taxes and fees

A balcony with a view of a body of water, a pool, and outdoor seating.

A waterfront property with a large building, a smaller structure with a thatched roof, and several boats docked.

A bar area with a long counter, bar stools, and a view of the water.

An outdoor dining area with tables and chairs, overlooking a body of water.

5. Fairfield Inn & Suites by Marriott Marathon Florida Keys

Marathon

Float away in a paradise with two outdoor pools, poolside dining, and marina views.

$134 nightly

$151 total

Oct 25 - Oct 26

Total with taxes and fees

A large swimming pool with lounge chairs and palm trees.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

6. Hilton Garden Inn Key West / The Keys Collection

New Town

Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.

$136 nightly

$153 total

Oct 8 - Oct 9

Total with taxes and fees

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.

A balcony with wicker furniture, a view of the sea, and a spiral staircase.

A balcony with wicker furniture, a view of the water, and a railing.

A beach view with a wooden pier, palm trees, and a sunset over the water.

7. Beachside Resort & Residences

Key West

Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.

$185 nightly

$208 total

Oct 4 - Oct 5

Total with taxes and fees

A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

A hotel with a central courtyard, palm trees, and a fountain.

An outdoor patio with tables and chairs, umbrellas, and palm trees.

8. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Splash into tropical paradise at this resort's cabana-lined pool with views and poolside cocktails.

$153 nightly

$172 total

Oct 11 - Oct 12

Total with taxes and fees

View all properties

Choose what matters most at hotels with a pool in Florida Keys

Breakfast included

4 stars

5 stars

Hot tub

Spa

Hotels with pools and free breakfast in Florida Keys

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

A modern office space with a reception desk, computer, and seating area.

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town

$154 nightly

$173 total

Oct 4 - Oct 5

Total with taxes and fees

Blue Flamingo Resort Key West

New Town

$168 nightly

$189 total

Oct 4 - Oct 5

Total with taxes and fees

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

A two-story yellow house with a porch, white railings, and green shutters.

The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

Silver Palms Inn & Historic Homes

Old Town Key West

$179 nightly

$201 total

Oct 7 - Oct 8

Total with taxes and fees

DoubleTree Resort by Hilton Grand Key - Key West

Key West

$153 nightly

$172 total

Oct 11 - Oct 12

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

A hotel room with a balcony, a bed, a desk, and two chairs.

A bar area with a thatched roof, wooden chairs, and a poolside view.

Hampton Inn Key West FL

Key West

$152 nightly

$171 total

Oct 7 - Oct 8

Total with taxes and fees

A swimming pool surrounded by palm trees and a natural rock formation.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

A covered outdoor seating area with a pool in the background.

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

Havana Cabana at Key West

New Town

$184 nightly

$207 total

Nov 1 - Nov 2

Total with taxes and fees

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

A tall palm tree with a white building in the background.

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

Parrot Key Hotel & Villas

Northside Resort

$173 nightly

$195 total

Oct 13 - Oct 14

Total with taxes and fees

An outdoor bar area with wooden tables and blue stools, a bar counter, and a sign that reads "Liqour Store".

A motel with a porch, white chairs, and a signboard.

A modern kitchen with a coffee station, a television, and a display case with baked goods.

A modern kitchen with a granite countertop, white cabinetry, and a coffee machine.

Southwinds Motel

Old Town Key West

$169 nightly

$190 total

Oct 5 - Oct 6

Total with taxes and fees

A hotel with a swimming pool, balconies, and a view of the sea.

A marina with jet skis docked in front of a hotel with a dock and a boat in the background.

A beach wedding setup with white chairs, a wooden arch, and lanterns.

A balcony with a view of the ocean, a table, chairs, and a railing.

Hyatt Centric Key West Resort and Spa

Key West Historic District

$290 nightly

$326 total

Oct 4 - Oct 5

Total with taxes and fees

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.

A building with a sign reading "ALMOND Frog & Toad Inn" and a "VACANCY" sign below it.

A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

$204 nightly

$230 total

Oct 5 - Oct 6

Total with taxes and fees

View all properties

4-star hotels with pools in Florida Keys

A hotel with a covered entrance, multiple balconies, and palm trees.

A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.

A waterfront hotel with multiple balconies, a dock, and boats.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

Opal Key Resort & Marina, Key West

Old Town Key West

$294 nightly

$331 total

Oct 4 - Oct 5

Total with taxes and fees