Key West

Key West Hotels with Pools

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Best Key West Hotels with Swimming Pools

Check out our selection of Key West hotels with Pools
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotel near Downtown Key West,Key West
A stay at Silver Palms Inn & Historic Homes places you in the heart of Key West, within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. This hotel is 0.7 mi (1 km) from Florida Keys Beaches and 0.7 mi (1.2 km) from South Beach. Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a television in a common area. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Make yourself at home in one of the 50 individually furnished guestrooms, featuring refrigerators and LCD televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wired and wireless internet access keeps you connected, while iPod docking stations help you enjoy your music in the comfort of your room. Bathrooms have showers and hair dryers.

"The second time I came to Key West, the southernmost town in the United States, the hotel was not in the center of the old town, but it was quiet in the middle of the noisy, it was convenient to go anywhere, the breakfast was simple, but the room was very comfortable, and the former residence of Hemingway was worth seeing."
Very Good
118 reviews
8.9/10
1 night
From TWD 2,223
Check Availability
99+
Hotel near Downtown Key West,Key West
Featured facilities: Exclusive Beach Area, Bar, Spa
Very Good
109 reviews
8.9/10
1 night
From TWD 7,502
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94
Hotels in Key West
With a stay at Authors of Key West Guest House in Key West (Key West Historic District), you'll be within a 5-minute drive of Key West Lighthouse and Keeper's Quarters Museum and Duval Street. This bed & breakfast is 1 mi (1.5 km) from Ernest Hemingway Home and Museum and 1 mi (1.6 km) from Clarence S. Higgs Memorial Beach Park. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. Additional amenities at this bed & breakfast include complimentary wireless internet access, concierge services, and a picnic area. A complimentary continental breakfast is served daily from 8:00 AM to 10:30 AM. Featured amenities include complimentary newspapers in the lobby and a water dispenser. Make yourself at home in one of the 13 air-conditioned rooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and hair dryers. Conveniences include irons/ironing boards, and housekeeping is provided daily.

"This is a very cute mini inn. On white road, not far from Hemingway's former residence, lighthouse, Western Reef Cemetery, Duval Street. The room was lovely and there was a mini pool (similar to a jacuzzi) The artist room faces the street, and there are motorcycles blowing the street at night, and there is unavoidable noise. The ”Hemingway House” should be better. Breakfast is very simple, all bought now. Don't expect too much. (Last picture) Parking is free, very good. Overall very satisfied."
Great
109 reviews
9.0/10
1 night
From TWD 3,145
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Spa
Very Good
107 reviews
8.1/10
1 night
From TWD 3,207
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Fitness Room
Great
101 reviews
9.2/10
1 night
From TWD 8,538
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Massage Room, Fitness Room
Very Good
101 reviews
8.9/10
1 night
From TWD 8,300
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99+
Hotel near Duval,Key West
Featured facilities: Bar
Great
101 reviews
9.1/10
1 night
From TWD 3,801
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62
Hotels in Key West
Featured facilities: Public Beach, Bar
Great
105 reviews
9.2/10
1 night
From TWD 10,224
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62
Hotel near Duval,Key West
Featured facilities: Public Beach, Bar, Massage Room
Amazing
101 reviews
9.6/10
1 night
From TWD 8,623
Check Availability
99+
Hotel near Duval,Key West
Featured facilities: Bar
Very Good
102 reviews
8.7/10
1 night
From TWD 5,948
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See All Hotels with Pools in Key West

Top rated hotels in Key West

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Explore genuine reviews and ratings from real travellers to find the perfect accommodation for your needs.

Paradise Inn - Adult Exclusive

9.0/10
Great
Posted on May 13, 2025
TiChatton
Nice and spacious room included Nespresso pods. Central location, not too far from Duval st. Breakfast included was alright, included hard boiled eggs, cereal, waffle machine, bagels and toast with jam, PB, and cream cheese. Starbucks coffee machine and water machine available throughout the day. Air conditioning fan is a bit loud as the air handler is in the room. No one in the lobby to handle noise complaints at night, especially drunks using the pool after returning from a night out being obnoxious. Charging a resort fee of $34.99, then charging $30 for parking is just an absolute money grab. Should've went with the other options that included the parking, but didn't include breakfast as that breakfast was not worth $34.99...
Price per night from:TWD 4,409

Coco Plum Inn

8.9/10
Very Good
Posted on Mar 4, 2026
Selina seet
Fantastic location by the green parrot and u don’t hear the party noise on the street. Good size room and cute little patio- but the ac just blew air like a fan and did not lower the temp. Way too humid and couldn’t sleep well. The breakfast situation was not good. Groups would claim all 3 tables with personal items and you would have to wait. Works if you r not there for work. I popped my head in to the cook in the kitchen to say hi there’s 2 more of us and he snapped at me saying can’t u see there’s others waiting? lol. He went table to table to ask what they wanted- even tho it was the one item on the menu for the day. So it was a slow process- ended up grabbing outside food.
Price per night from:TWD 4,300

Hampton Inn Key West

8.8/10
Very Good
Posted on Oct 5, 2024
Guest User
The room was big, comfortable and quiet. Although it was in the airport area, we couldn't hear any airplane sounds. We drove ourselves, and it was convenient to stay anywhere with a car. We didn't have to choose a hotel in the city, after all, the city was so small.
Price per night from:TWD 4,247

Blue Flamingo Resort Key West

8.8/10
Very Good
Posted on Feb 7, 2026
Guest User
The front desk was wonderful, room was good, pool area very nice. The problem was the cleaning crew. We wanted to stay until checkout at 11:00, as our flight didn’t leave until 2:30. At 10:00, two cleaning ladies with their cart parked directly outside our window, constantly looking into our window, just waiting for us to leave. We were extremely uncomfortable! No one likes to be watched from a peeping Tom outside their window. It was terrible. When we were finally left, we couldn’t get out the door because their cart was blocking the way.
Price per night from:TWD 4,414

La Concha Key West

8.8/10
Very Good
Posted on Dec 18, 2022
Guest User
La concha is a beautiful & historic hotel in the heart of beautiful Key West. The location is unbeatable & the balcony rooms, while smaller than other standard rooms, offers excellent people watching & beautiful blue sky views. A parking space is included, which is great to have right on Duval & Fleming Streets. The staff was mostly very friendly, but the service level varied. At one point in our stay, the front desk went out of their way to make us a key card to use the microwave located in the conference room. When I asked to use it the next day, another staff member says there wasn't one in the building. I went & took a photo through the window to show him. He then said he could not grant me access as the desk had previously done. No biggie but a little frustrating. Our main issue with the hotel was HIDDEN FEES. Upon arrival, we were told we would be charged a fee of over $80 per room as a ”destination fee,” which was never explicitly disclosed & was certainly not fairly advertised. I asked about waiving this fee & the night desk said it was possible to check & see with day manager. The next day, they insisted the fee could not be waived & were unwilling to help with it further. I let them know I booked through a 3rd party prepaid, it said fees & taxes were included. They said read the fine print. They charged my card for the fees. Not being forthcoming and clear about the destination fee was the issue I had. And having parts of the hotel amenities, including outdoor areas, being closed off during the stay make this resort/destination fee more of a slap in the face. To highlight this point, the staff at this ”destination” hotel warned us that if we see some stuff a little run down or not in operation, its because the hotel just got bought & things wouldn't get straightened out until the new company takes over. Also minor issues for such a pricey hotel included missing slats on the inner balcony door & similar minor cosmetic issues. Other than that it is a beautiful building & top-notch location. Overall the experience was very enjoyable. P.S. The awesome bar tender makes delicious key lime martinis!
Price per night from:TWD 7,340

Havana Cabana at Key West

8.7/10
Very Good
Posted on Nov 22, 2025
Slien3
Great! What a nice hotel! Entry looks great, beautiful Cuban atmosphere. It smells great. The staff is awfully good. Nice pool with a number of leguans as residents. Nice clean large rooms, good beds. Resort fee, but you'll get the following for it: Gratis parkeren Pendelbus to Duval street Daily cleaning 2 welcome drinks at the outdoor bar Every day 2 bottles of water on the room Handdoes, sunburn, water at the pool 12.00 hour smoothy 14.00 hour jell-shots 16.00-18.00 hour snacks (Churro's!) We had booked three nights, but we were so happy to have booked a few nights. We're coming back!!
Price per night from:TWD 4,813

DoubleTree by Hilton Hotel Grand Key - Key West

8.6/10
Very Good
Posted on Nov 14, 2025
Guest User
Very welcoming hotel, complimentary welcome pack with cookie, bottled water, and reusable water bottle upon arrival. Friendly receptionist who speaks French. The pool area and bar/restaurant are very pleasant. Delicious meals and cocktails. Free shuttle to the city center every hour. Highly recommend this hotel 😉
Price per night from:TWD 4,095

The Cabana Inn Key West - Adult Exclusive

8.4/10
Very Good
Posted on May 14, 2025
Guest User
Great hotel, very cozy. All entertainment and attractions are nearby, but the hotel itself is not noisy. Good breakfast, happy hour in the evening with wine, cheese and snacks. If there is not enough space for parking near the hotel, then a couple of blocks away you can park for $ 15 per day. Of the nuances - noisy air conditioning in the room and a dirty pool (lots of leaves).
Price per night from:TWD 4,837

Hilton Garden Inn Key West/The Keys Collection

8.2/10
Very Good
Posted on Feb 7, 2024|Queen Bed Studio with Sofabed
USGuest User
Nice place. Great location. Friendly staff. Comfortable room. Parking is NOT included. I'm a bit annoyed about that because I didn't find anything about that when reserving the room. I even called and left a message on the concierge line asking about parking but never got a callback.
Price per night from:TWD 3,445

Casa Marina Key West, Curio Collection by Hilton

8.1/10
Very Good
Posted on Mar 4, 2024
Nanjipangqie
The location of the hotel is of high quality, and the facilities and environment are good. The bedding is clean and comfortable, and the typical American breakfast in the morning is very comfortable to sit outside and enjoy. Worth a visit!
Price per night from:TWD 8,908

Frequently Asked Questions

What's the best hotel with Swimming Pools in Key West?

What's the average price for hotels with Swimming Pools in Key West?

For hotels with Swimming Pools in Key West, the average price is TWD 18,094 on weekdays and TWD 22,199 on weekends (Friday–Saturday).

Which hotels with Swimming Pools in Key West have deals?

There are many deals available on Trip.com for both new and loyal users. Please check the promotions page to save your upcoming stays.

What's the best luxury hotel with Swimming Pools in Key West?

Key West has many luxury hotels with Swimming Pools. Casa Marina Key West, Curio Collection by Hilton (from TWD 5,910) is a popular option.

Key West Hotels with Pools Information

Total properties152
Number of reviews9,042
Highest priceTWD 73,081
Lowest priceTWD 5,635
Weekday Avg. PriceTWD 18,094
Weekend Avg. PriceTWD 22,199