A sign for the Key West Museum of Art & History at the Custom House.

Find Hotels with a Pool in Key West, FL

Q: What are some hotels with pools in Key West?

Blue Flamingo Resort Key West : Hotel located near Florida Keys Beaches. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. Ibis Bay Beach Resort : Hotel located near Florida Keys Beaches. Offers a private beach, an outdoor pool, and daily. Hilton Garden Inn Key West / The Keys Collection : Hotel located near Florida Keys Beaches. Provides 2 restaurants, a pool, and complimentary wired internet access. The Perry Hotel & Marina Key West : Hotel located near Smathers Beach. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. Parrot Key Hotel & Villas : Hotel located near Florida Keys Beaches. Offers a beach shuttle, 4 outdoor pools, and complimentary wireless internet access.

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November 2026

December 2026

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Our top choices for Key West hotels with a pool

A white outdoor seating area with a pool view, featuring white chairs and a small table with a vase of flowers.

1. Opal Key Resort & Marina, Key West

Old Town Key West

AED 1,215 total

includes taxes & fees

29 Nov - 30 Nov

A pool area with lounge chairs and a cabana.

2. Ocean Key Resort - A Noble House Resort

Key West Historic District

Float in the outdoor pool with Key West sunset views, poolside loungers, and bar service for luxury.

AED 1,348 total

includes taxes & fees

29 Nov - 30 Nov

A poolside area with wicker furniture, a covered seating area, and a white building with a balcony.

3. Lighthouse Hotel - Key West Historic Inns

Old Town Key West

Take a dip in Key West's serene outdoor pool oasis, where relaxation meets historic charm just steps from Duval Street.

AED 1,012 total

includes taxes & fees

30 Nov - 1 Dec

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

4. Hyatt Centric Key West Resort and Spa

Key West Historic District

AED 1,322 total

includes taxes & fees

1 Dec - 2 Dec

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

5. Silver Palms Inn & Historic Homes

Old Town Key West

Pristine waters in the outdoor pool offer relaxation after exploring Key West's vibrant attractions.

AED 876 total

includes taxes & fees

1 Dec - 2 Dec

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

6. Courtyard by Marriott Key West Waterfront

Northside Resort

Savor the sun in this poolside paradise with tropical gardens and a relaxing hot tub.

AED 757 total

includes taxes & fees

29 Nov - 30 Nov

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

7. Hampton Inn Key West FL

Key West

Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.

AED 698 total

includes taxes & fees

16 Nov - 17 Nov

A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.

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

New Town

Float in a tranquil oasis at this Key West hotel, where the outdoor pool beckons after adventures along nearby hiking trails.

AED 657 total

includes taxes & fees

29 Nov - 30 Nov

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

9. Pier House Resort & Spa

Key West Historic District

AED 1,658 total

includes taxes & fees

28 Nov - 29 Nov

A couple relaxing by a poolside lounge with a view of palm trees and a clear sky.

10. H2O Suites - Adults Only

Old Town Key West

AED 1,731 total

includes taxes & fees

30 Nov - 1 Dec

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Choose what matters most at hotels with a pool in Key West

Breakfast included

Hot tub

Hotels with pools and free breakfast in Key West

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

Havana Cabana at Key West

New Town

AED 803 total

includes taxes & fees

29 Nov - 30 Nov

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

DoubleTree Resort by Hilton Grand Key - Key West

Key West

AED 617 total

includes taxes & fees

17 Nov - 18 Nov

A two-story building with a covered entrance, palm trees, and a bench outside.

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

AED 930 total

includes taxes & fees

17 Nov - 18 Nov

Silver Palms Inn & Historic Homes

Old Town Key West

AED 876 total

includes taxes & fees

1 Dec - 2 Dec

A swimming pool with lounge chairs and palm trees.

Hilton Garden Inn Key West / The Keys Collection

New Town

AED 578 total

includes taxes & fees

17 Nov - 18 Nov

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

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

New Town

AED 657 total

includes taxes & fees

29 Nov - 30 Nov

A building with a white exterior, a large red awning, and a gated entrance.

Authors of Key West Guest House

Key West Historic District

AED 591 total

includes taxes & fees

30 Nov - 1 Dec

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Hotels with pools and hot tubs in Key West

Havana Cabana at Key West

New Town

AED 803 total

includes taxes & fees

29 Nov - 30 Nov

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

Alexander's Guesthouse - Adult Exclusive

Old Town Key West

AED 1,002 total

includes taxes & fees

12 Nov - 13 Nov

Hilton Garden Inn Key West / The Keys Collection

New Town

AED 578 total

includes taxes & fees

17 Nov - 18 Nov

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

AED 1,215 total

includes taxes & fees

29 Nov - 30 Nov

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

AED 917 total

includes taxes & fees

18 Nov - 19 Nov

A spacious room with a wooden floor, white furniture, and large windows.

Paradise Inn Key West - Adults Only

Old Town Key West

AED 922 total

includes taxes & fees

18 Nov - 19 Nov

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

Courtyard by Marriott Key West Waterfront

Northside Resort

AED 757 total

includes taxes & fees

29 Nov - 30 Nov

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

AED 1,029 total

includes taxes & fees

17 Nov - 18 Nov

View all properties

4-star hotels with pools in Key West

DoubleTree Resort by Hilton Grand Key - Key West

Key West

AED 617 total

includes taxes & fees

17 Nov - 18 Nov

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

The Perry Hotel & Marina Key West

Stock Island

AED 694 total

includes taxes & fees

30 Nov - 1 Dec

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

AED 930 total

includes taxes & fees

17 Nov - 18 Nov

A beach with a wooden pier, palm trees, and beach umbrellas.

The Reach Key West, Curio Collection by Hilton

Old Town Key West

AED 1,153 total

includes taxes & fees

30 Nov - 1 Dec

Ocean Key Resort - A Noble House Resort

Key West Historic District

AED 1,348 total

includes taxes & fees

29 Nov - 30 Nov

Hyatt Centric Key West Resort and Spa

Key West Historic District

AED 1,322 total

includes taxes & fees

1 Dec - 2 Dec

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

AED 1,182 total

includes taxes & fees

23 Nov - 24 Nov

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Top Key West Hotel Reviews

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

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

william

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

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...

Courtney

H2O Suites - Adults Only

Old Town Key West

10/10 Excellent

My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...

Erin

A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

The Marquesa Hotel

Old Town Key West

10/10 Excellent

David

A wooden deck with lush greenery and a pool area.

Douglas House - Adults Only

Old Town Key West

10/10 Excellent

Anthony

A couple walking along a poolside pathway surrounded by lush greenery.

The Gardens Hotel

Old Town Key West

10/10 Excellent

Anonymous traveler

A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.

Alexander's Guesthouse - Adult Exclusive

Old Town Key West

10/10 Excellent

Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.

Dominick

A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

Simonton Court Historic Inn & Cottages

Key West Historic District

10/10 Excellent

RADANA

A swimming pool with a hot tub, surrounded by a wooden deck and lush greenery.

Key West Villas

Old Town Key West

10/10 Excellent

Thys

A pool area with lounge chairs and a dining table, surrounded by palm trees and a house with a porch.

The Conch House Heritage Inn

Old Town Key West

10/10 Excellent

Nicholas

A pool area with lounge chairs and a wooden building with balconies.

Island City House Hotel

Key West Historic District

10/10 Excellent

Keith

A swimming pool with a mural of a dolphin and a butterfly, surrounded by lounge chairs and palm trees.

Duval House

Old Town Key West

10/10 Excellent

The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...

Sarah

A pool area with lounge chairs and palm trees.

Santa Maria Suites

Old Town Key West

10/10 Excellent

We stayed here for one night for my husband's 40th birthday. The hotel was aware we were celebrating an occasion and offered complimentary refreshment's in our room. We were able to check on early, got upgraded to pool view and also checked out late! When we arrived we were amazed with how huge the suite was. It was the same size as a condo. The decor was beautiful and the entire place was immaculate, including the outside. What we liked most was how quiet and relaxing the place was (there...

Val

Silver Palms Inn & Historic Homes

Old Town Key West

10/10 Excellent

Janice

A swimming pool with a white picket fence, surrounded by lounge chairs and potted plants.

Weatherstation Inn

Old Town Key West

10/10 Excellent

Tucked into the very quiet Truman Annex, the Weatherstation Inn was a great find. It is an old house, built in 1911. If you enjoy old, quiet inns with reconfigured spaces, then this is the place for you. If you are looking for uniform, sleek and modern, then head on down the road. The continental breakfast was just right with delicious pastries from local bakery and the bed was comfy. Perhaps the most perfect aspect of the inn is the parking space where we parked our vehicle upon arrival and did...

GaGirlWalking

A white house with a swimming pool, palm trees, and outdoor seating.

Ella's Cottages - Key West Historic Inns

Old Town Key West

10/10 Excellent

Cara

A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

Westwinds Inn

Key West Historic District

10/10 Excellent

The grounds of the property are absolutely beautiful. The gardens are well-maintained and we loved perusing them. Both pool areas are wonderful, and the amenities such as the bathhouse, lounge, library, and BBQ area are first rate. The room was to our liking and matched the aesthetic of Key West. Walking distance to nearby attractions was approximately 10 minutes and very easy, and the bakery just down the street was wonderful for breakfast, lunch, or a quick snack. We will absolutely stay again...

Daniel

Frequently Asked Questions

How many hotels with pools are there in Key West?

Expedia's 281 hotels in Key West give you a great choice for your poolside getaway.

What's it like visiting Key West?

If taking it easy by the pool is your idea of a great getaway, you might want to think about Key West, which has 281 places to stay with pools. While you're here, you can explore attractions like Duval Street and Florida Keys Beaches, and then relax and unwind poolside at one of the accommodations in Key West that guests like for their pools.

What are some hotels with pools in Key West?

Blue Flamingo Resort Key West: Hotel located near Florida Keys Beaches. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. Ibis Bay Beach Resort: Hotel located near Florida Keys Beaches. Offers a private beach, an outdoor pool, and daily. Hilton Garden Inn Key West / The Keys Collection: Hotel located near Florida Keys Beaches. Provides 2 restaurants, a pool, and complimentary wired internet access. The Perry Hotel & Marina Key West: Hotel located near Smathers Beach. Features 2 restaurants, 2 outdoor pools, and 2 pool bars. Parrot Key Hotel & Villas: Hotel located near Florida Keys Beaches. Offers a beach shuttle, 4 outdoor pools, and complimentary wireless internet access.

What is there to see and do in Key West?

Explore places like Duval Street and Florida Keys Beaches while you're in Key West. The picturesque setting of Key West Butterfly and Nature Conservatory and Southernmost Point showcase the area’s natural beauty. Key West appeals to visitors with its beautiful ocean views, great live music scene, and bar scene.

When is the best time to book a hotel with a pool in Key West?

Taking into account the local weather in Key West is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Key West is 38 inches.

Find Hotels with a Pool in Key West, FL

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Key West hotels with a pool

1. Opal Key Resort & Marina, Key West

2. Ocean Key Resort - A Noble House Resort

3. Lighthouse Hotel - Key West Historic Inns

4. Hyatt Centric Key West Resort and Spa

5. Silver Palms Inn & Historic Homes

6. Courtyard by Marriott Key West Waterfront

7. Hampton Inn Key West FL

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

9. Pier House Resort & Spa

10. H2O Suites - Adults Only

Choose what matters most at hotels with a pool in Key West

Hotels with pools and free breakfast in Key West

Havana Cabana at Key West

Hotels with pools and hot tubs in Key West

Havana Cabana at Key West

4-star hotels with pools in Key West

DoubleTree Resort by Hilton Grand Key - Key West

Top Key West Hotel Reviews

Almond Tree Inn Hotel - Adults Only

10/10 Excellent

Frequently Asked Questions

How many hotels with pools are there in Key West?

What's it like visiting Key West?

What are some hotels with pools in Key West?

What is there to see and do in Key West?

When is the best time to book a hotel with a pool in Key West?