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

Find Hotels with a Pool in Florida Keys

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Check availability on Florida Keys Hotels with a Pool

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Sep 1 - Sep 2
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Sep 2 - Sep 3
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Sep 4 - Sep 6
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Sep 11 - Sep 13

Our top choices for Florida Keys hotels with a pool

A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.
A bathroom with a shower, toilet, and sink, featuring a black and white hexagonal tile pattern on the floor and walls.

1. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
  • Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.
$134 nightly
$151 total
Sep 3 - Sep 4
Total with taxes and fees
Silver Palms Inn & Historic Homes
A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.
A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.

2. Eden House

Eden House
Key West Historic District
$99 nightly
$111 total
Sep 27 - Sep 28
Total with taxes and fees
Eden House
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A balcony with wicker furniture, a view of the water, and a railing.
A balcony with wicker furniture, a red chair, and a lamp.
A beach view with a wooden pier, palm trees, and a sunset over the water.

3. Beachside Resort & Residences

Beachside Resort & Residences
Key West
  • Plunge into paradise with sun-kissed loungers and poolside cocktails at this waterfront hotel.
$185 nightly
$208 total
Sep 3 - Sep 4
Total with taxes and fees
Beachside Resort & Residences
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a balcony, a bed, a desk, and two chairs.
A balcony with wicker furniture and a view of the ocean and palm trees.

4. Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
  • Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
$139 nightly
$157 total
Sep 20 - Sep 21
Total with taxes and fees
Hampton Inn Key West FL
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A hotel room with a bed, a bedside table with a lamp, a small table with a basket, a blue and white striped ottoman, and a balcony with a view of palm trees and the ocean.
A balcony with two blue lounge chairs, a wooden ceiling, and a view of the ocean and palm trees.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.

5. Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
  • Splash into paradise with two stunning outdoor pools overlooking a private white sand beach.
$165 nightly
$186 total
Sep 21 - Sep 22
Total with taxes and fees
Chesapeake Beach Resort
A poolside area with lounge chairs and a view of boats in the background.
A clear view of turquoise ocean water and a blue sky with clouds.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A hotel room with a balcony overlooking a marina and the ocean.

6. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
  • Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.
$167 nightly
$188 total
Sep 8 - Sep 9
Total with taxes and fees
Hilton Key West Resort & Marina
A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.
A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.
A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

7. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
Key West
  • Oceanfront relaxation awaits with heated pool sanctuary and hot tub retreat, mere steps from Key West's beautiful Smathers Beach.
$209 nightly
$235 total
Sep 15 - Sep 16
Total with taxes and fees
Hyatt Vacation Club at Windward Pointe, Key West
A swimming pool with yellow lounge chairs, palm trees, and a white building in the background.
A reception desk with a marble countertop, a Toshiba laptop, a vase with white flowers, and a sign indicating an office.
A covered outdoor area with a view of a pool and palm trees.
A covered outdoor seating area with a round table and two chairs, overlooking a garden with palm trees.

8. Kingsail Resort

Kingsail Resort
Marathon
  • Sleek outdoor pool with marina views makes waterfront adventures a dream at Kingsail resort.
$74 nightly
$83 total
Sep 20 - Sep 21
Total with taxes and fees
Kingsail Resort
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 modern living room with a sectional sofa, a small round table, and a potted plant.

9. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
  • Poolside bliss awaits with cocktails, sun loungers, and a hot tub for ultimate relaxation.
$135 nightly
$151 total
Sep 14 - Sep 15
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
A resort with a swimming pool, lounge chairs, and palm trees.
A spacious living area with a large island, wooden furniture, and a ceiling fan.
A balcony with wicker furniture and a view of the ocean and palm trees.

10. Lime Tree Bay Resort

Lime Tree Bay Resort
Long Key
  • A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort.
$172 nightly
$194 total
Sep 7 - Sep 8
Total with taxes and fees
Lime Tree Bay Resort
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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 swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.
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.

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
$134 nightly
$151 total
Sep 3 - Sep 4
Total with taxes and fees
Silver Palms Inn & Historic Homes
A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.
A pink building with a white door, a balcony with a white railing, and a view of a pool area.
A hotel with a white facade, multiple balconies, and lush tropical landscaping.
A row of bicycles parked in front of a building with a white balcony and a palm tree.

The Palms Hotel

The Palms Hotel
Old Town Key West
$143 nightly
$161 total
Sep 29 - Sep 30
Total with taxes and fees
The Palms Hotel
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 modern kitchen with a marble island, wooden cabinets, and pendant lighting.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
$139 nightly
$157 total
Sep 20 - Sep 21
Total with taxes and fees
Hampton Inn Key West FL
A beach with palm trees and lounge chairs.
A swimming pool with clear blue water, surrounded by a white deck and a black metal fence.
A waterfront hotel with multiple floors, palm trees, and a calm reflective pool.
A hotel room with a large bed, a ceiling fan, a nightstand with a lamp, and a view of the beach through the window.

Chesapeake Beach Resort

Chesapeake Beach Resort
Matecumbe
$165 nightly
$186 total
Sep 21 - Sep 22
Total with taxes and fees
Chesapeake Beach Resort
A clear view of turquoise ocean water and a blue sky with clouds.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A hotel room with a balcony overlooking a marina and the ocean.

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
$167 nightly
$188 total
Sep 8 - Sep 9
Total with taxes and fees
Hilton Key West Resort & Marina
A 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 modern living room with a sectional sofa, a small round table, and a potted plant.

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
$135 nightly
$151 total
Sep 14 - Sep 15
Total with taxes and fees
Hilton Garden Inn Key West / The Keys Collection
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
A spacious living room with a wooden ceiling, white sofas, a patterned armchair, a glass coffee table, and a large painting on the wall.
A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.
A spacious living room with a sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly

Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
Old Town Key West
$143 nightly
$161 total
Sep 8 - Sep 9
Total with taxes and fees
Alexanders Guesthouse - Adult Exclusive, LGBTQ Friendly
A building with a white exterior, a large red awning, and a gated entrance.
A spacious kitchen with a dining area, large windows, and a view of the outdoors.
A pool area with lounge chairs and a lifebuoy.
A paved pathway lined with various plants and trees, leading to a building with a beige exterior.

Authors of Key West Guest House

Authors of Key West Guest House
Key West Historic District
$84 nightly
$95 total
Sep 3 - Sep 4
Total with taxes and fees
Authors of Key West Guest House
A swimming pool surrounded by palm trees and a natural rock formation.
An outdoor dining area with round tables and chairs, surrounded by greenery and a mural.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

Havana Cabana at Key West

Havana Cabana at Key West
New Town
$166 nightly
$187 total
Sep 16 - Sep 17
Total with taxes and fees
Havana Cabana at Key West
A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.
A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.
A beachside lounge with chairs and umbrellas, overlooking the ocean.
A beachfront resort with a prominent sign, white balconies, and tropical landscaping.

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
View all properties

4-star hotels with pools in Florida Keys

A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.
A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.
A cozy cabin with a wooden interior, a bed, a TV, and a kitchenette.
A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

Eden House

Eden House
Key West Historic District
$99 nightly
$111 total
Sep 27 - Sep 28
Total with taxes and fees
Eden House
A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.
A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.
A beachside lounge with chairs and umbrellas, overlooking the ocean.
A beachfront resort with a prominent sign, white balconies, and tropical landscaping.

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
Old Town Key West
$210 nightly
$237 total
Sep 8 - Sep 9
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
A clear view of turquoise ocean water and a blue sky with clouds.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A hotel room with a balcony overlooking a marina and the ocean.

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
$167 nightly
$188 total
Sep 8 - Sep 9
Total with taxes and fees
Hilton Key West Resort & Marina
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.
A large, two-story house with a prominent tower and a covered porch.
A grand staircase with ornate railings and a chandelier.

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Old Town Key West
$259 nightly
$291 total
Sep 7 - Sep 8
Total with taxes and fees
Southernmost House - Adult Exclusive
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 beach with palm trees, lounge chairs, and umbrellas.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
$191 nightly
$215 total
Sep 14 - Sep 15
Total with taxes and fees
Parrot Key Hotel & Villas
A swimming pool surrounded by palm trees and a natural rock formation.
An outdoor dining area with round tables and chairs, surrounded by greenery and a mural.
A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

Havana Cabana at Key West

Havana Cabana at Key West
New Town
$166 nightly
$187 total
Sep 16 - Sep 17
Total with taxes and fees
Havana Cabana at Key West
A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
A hotel with a central courtyard, palm trees, and a fountain.
A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.
An outdoor patio with tables and chairs, umbrellas, and palm trees.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
$141 nightly
$159 total
Sep 27 - Sep 28
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
A beach with a wooden pier, palm trees, and beach umbrellas.
A modern bar area with a central island, white bar stools, and a view of the ocean.
An outdoor dining area with tables and chairs, overlooking the ocean.
An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
Old Town Key West
$256 nightly
$288 total
Sep 28 - Sep 29
Total with taxes and fees
The Reach Key West, Curio Collection by Hilton
A hotel with a swimming pool, balconies, and a view of the sea.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
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

Hyatt Centric Key West Resort and Spa
Key West Historic District
$263 nightly
$296 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Centric Key West Resort and Spa
A wooden deck with a pool and chairs overlooking a beach with palm trees.
A pool area with palm trees and a view of the ocean.
A bar area with stools, a counter, and hanging lanterns.
A hotel room with a sofa, a desk, a chair, a TV, and a balcony with curtains.

Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club
Marathon
$215 nightly
$241 total
Sep 9 - Sep 10
Total with taxes and fees
Grassy Flats Resort & Beach Club
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.
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Top Florida Keys Hotel Reviews

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

8/10 Good
"Loved the overall Resort! The beach thenchair"
Julie Marie 4-night trip
Posted 8 hours ago
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Bayside Inn Key Largo

Bayside Inn Key Largo

10/10 Excellent
"The place is beautiful and clean and affordable. I would definitely be willing to stay there again. The little Inlet gives us time to be by the water and fish or swim or paddle boat for free. Already wanting to make plans for next year thank you Bayside for a wonderful visit."
Debbie Lynn 3-night trip
Posted 9 hours ago
Bayside Inn Key Largo
Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Me encantó mi estadía. El lugar estaba muy limpio, cómodo y tranquilo. El personal fue muy amable y atento. El desayuno estuvo muy bueno y disfrutamos mucho de las instalaciones. Todo estuvo excelente y definitivamente volvería. ¡Lo recomiendo 100%!"
Yamirka 4-night trip
Posted 10 hours ago
Lime Tree Bay Resort
Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"It was a wonderful experience all around!!"
Natalie 4-night trip
Posted 10 hours ago
Amara Cay Resort
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

10/10 Excellent
"Perfection!"
Lauren 3-night trip
Posted 13 hours ago
Playa Largo Resort & Spa, Autograph Collection
Waterside Suites & Marina

Waterside Suites & Marina

10/10 Excellent
"Rainbow Reef is next door. Huge patio to dry gear. Scuba divers perfect spot!"
Marcy 4-night trip
Posted 1 day ago
Waterside Suites & Marina
Islander Resort

Islander Resort

8/10 Good
"Great property with an amazing concept, especially in an area where there aren’t many high-end properties offering this style and experience. The facilities are excellent, and overall we really enjoyed our stay. My only negative feedback is that a few members of staff were constantly on their phones watching clips and videos, often with the volume turned up. We found this quite annoying, particularly when trying to relax quietly by the pool. It would be great if staff could be reminded to use headphones or keep phone use to a minimum in guest relaxation areas. Room maintaince could also be better."
Asoka 2-night trip
Posted 1 day ago
Islander Resort
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

10/10 Excellent
"The staff was amazing and very, very helpful! Amazing at trouble shooting and went over the top to help us out! The breakfast was very good, better than you would expect for a hotel and we really enjoyed the waterfront area."
Rebecca 4-night trip
Posted 1 day ago
Hampton Inn Key Largo Manatee Bay
Hawks Cay Resort

Hawks Cay Resort

10/10 Excellent
"Great place. Loved the area, the staff very helpful and nice. The villa could used a better cleaning but overall was a great stay, will definitely be back!!!"
Clara 3-night trip
Posted 2 days ago
Hawks Cay Resort

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