A large red brick building with arched windows and a prominent entrance.

Find Hotels with a Pool in Key West Historic District, FL

Q: What are some accommodations with pools in Key West Historic District?

Winslow's Bungalows - Key West Historic Inns : Hotel, 5-minute walk from Duval Street. Features complimentary wireless internet access, 3 outdoor pools, and LED televisions. The Reach Key West, Curio Collection by Hilton : Resort, 3-minute walk from Duval Street. Offers a private beach, an outdoor pool, and a full-service spa. Opal Key Resort & Marina, Key West : Hotel steps from Mallory Square. Provides 3 bars, an outdoor pool, and spa services. La Concha Key West, Autograph Collection : Hotel, 1-minute walk from Duval Street. Features 3 restaurants, an outdoor pool, and 2 bars. Hyatt Centric Key West Resort and Spa : Resort, 1-minute walk from Florida Keys Beaches. Offers a full-service spa, a pool, and a snack bar/deli.

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November 2026

December 2026

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Our top choices for Key West Historic District 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

NT$10,857 total

includes taxes & fees

Nov 29 - Nov 30

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

2. Hyatt Centric Key West Resort and Spa

Key West Historic District

NT$11,833 total

includes taxes & fees

Dec 1 - Dec 2

A pool area with lounge chairs and a cabana.

3. 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.

NT$12,060 total

includes taxes & fees

Nov 29 - Nov 30

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

4. Silver Palms Inn & Historic Homes

Old Town Key West

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

NT$7,832 total

includes taxes & fees

Dec 1 - Dec 2

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

5. The Marker Key West Harbor Resort

Key West Historic District

Splash into bliss at this harbor resort offering three pools, a poolside bar, and daily live entertainment.

NT$10,741 total

includes taxes & fees

Nov 17 - Nov 18

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

6. H2O Suites - Adults Only

Old Town Key West

NT$15,493 total

includes taxes & fees

Nov 30 - Dec 1

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

7. The Marquesa Hotel

Old Town Key West

NT$16,904 total

includes taxes & fees

Nov 29 - Nov 30

A pool area with a pink canopy, lounge chairs, and a seating area with cushions.

8. La Concha Key West, Autograph Collection

Key West Historic District

Relaxing poolside retreat in vibrant Key West with easy access to Duval Street and walking distance to all attractions.

NT$8,751 total

includes taxes & fees

Dec 1 - Dec 2

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

9. Orchid Key Inn - Adults Only

Old Town Key West

NT$9,340 total

includes taxes & fees

Dec 1 - Dec 2

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

10. 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.

NT$9,059 total

includes taxes & fees

Nov 30 - Dec 1

View all properties

Compare popular hotels in Key West Historic District

Property	Property class	Guest rating
Silver Palms Inn & Historic Homes	3.5 star property	9.4 Exceptional 1,039 reviews	View
La Concha Key West, Autograph Collection	4.0 star property	8.8 Excellent 516 reviews	View
Duval House	3.0 star property	9.6 Exceptional 1,139 reviews	View
Lighthouse Hotel - Key West Historic Inns	3.5 star property	9.0 Wonderful 1,000 reviews	View
Ocean Key Resort - A Noble House Resort	4.0 star property	9.2 Wonderful 1,000 reviews	View

Top Key West Historic District 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

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

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 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

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 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

The Marquesa Hotel

Old Town Key West

10/10 Excellent

David

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 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 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

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

Frequently Asked Questions

How many hotels with pools will I find in Key West Historic District?

Expedia's 146 hotels in Key West Historic District give you a great choice for your poolside getaway.

What's it like visiting Key West Historic District?

If lounging next to a pool is your idea of the perfect getaway, you may want to consider Key West Historic District, which offers 146 places to stay with pools. While you're visiting, you can explore attractions like Duval Street and Florida Keys Beaches, and then relax poolside at one of the accommodations in Key West Historic District that guests like for their pools.

What are some accommodations with pools in Key West Historic District?

Winslow's Bungalows - Key West Historic Inns: Hotel, 5-minute walk from Duval Street. Features complimentary wireless internet access, 3 outdoor pools, and LED televisions. The Reach Key West, Curio Collection by Hilton: Resort, 3-minute walk from Duval Street. Offers a private beach, an outdoor pool, and a full-service spa. Opal Key Resort & Marina, Key West: Hotel steps from Mallory Square. Provides 3 bars, an outdoor pool, and spa services. La Concha Key West, Autograph Collection: Hotel, 1-minute walk from Duval Street. Features 3 restaurants, an outdoor pool, and 2 bars. Hyatt Centric Key West Resort and Spa: Resort, 1-minute walk from Florida Keys Beaches. Offers a full-service spa, a pool, and a snack bar/deli.

What is there to see and do in Key West Historic District?

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

Find Hotels with a Pool in Key West Historic District, FL

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Key West Historic District hotels with a pool

1. Opal Key Resort & Marina, Key West

2. Hyatt Centric Key West Resort and Spa

3. Ocean Key Resort - A Noble House Resort

4. Silver Palms Inn & Historic Homes

5. The Marker Key West Harbor Resort

6. H2O Suites - Adults Only

7. The Marquesa Hotel

8. La Concha Key West, Autograph Collection

9. Orchid Key Inn - Adults Only

10. Lighthouse Hotel - Key West Historic Inns

Compare popular hotels in Key West Historic District

Top Key West Historic District Hotel Reviews

Almond Tree Inn Hotel - Adults Only

10/10 Excellent

Frequently Asked Questions

How many hotels with pools will I find in Key West Historic District?

What's it like visiting Key West Historic District?

What are some accommodations with pools in Key West Historic District?

What is there to see and do in Key West Historic District?

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