Key West

Key West Hotels with Pools

Find Key West hotels with a sprawling Pools.

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Top Hotels with Pools in Key West

Seek out top Key West hotels with proistine 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 CAD 82
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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 CAD 366
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99+
Hotels in Key West
Featured facilities: Bar, Gym
Very Good
116 reviews
8.8/10
1 night
From CAD 149
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Gym
Great
101 reviews
9.2/10
1 night
From CAD 370
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99+
Hotel near Duval,Key West
Featured facilities: Spa
Great
105 reviews
9.0/10
1 night
From CAD 191
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar, Massage room, Gym
Very Good
101 reviews
8.9/10
1 night
From CAD 360
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Bar
Great
101 reviews
9.0/10
1 night
From CAD 124
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99+
Hotels in Key West
Featured facilities: Bar, Gym
Very Good
120 reviews
8.9/10
1 night
From CAD 212
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99+
Hotel near Duval,Key West
Featured facilities: Bar, Massage room
Amazing
105 reviews
9.6/10
1 night
From CAD 248
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99+
Hotel near Downtown Key West,Key West
Featured facilities: Private beach area, Bar, Spa
Very Good
107 reviews
8.9/10
1 night
From CAD 325
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Latest Reviews for Key West Hotels

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Read genuine traveler ratings & reviews to find your perfect stay.

Duval House

9.3/10
Great
Posted on Jul 22, 2025
Guest User
Great place to stay for escape room lovers… Check-in closes at 9pm, and staff clock out. There isn’t a 24hours reception desk, so if you’re driving down be sure to leave plenty of time and get in contact so that you receive your late check-in instructions, unlike us. We arrived at 10pm, to a locked gate, with no idea what the code to get in was, and as we do not have US phones, were unable to call the staff. A guest kindly let us into the resort, and there is a phone on top of a mail box with an out of hours number. After calling, staff were able to talk us through how to get our keys, but the series of steps definitely made it feel like an escape room. Room: Small and compact room. This hotel is laid out like a series of small cabin style huts. To be fair it had all the essentials, and was clean. The sink was in the room separate from the toilet and shower which was a bit strange. All amenities provided. Unfortunately, the AC unit is very loud, but there is also a fan, which is quieter, and tolerable to have on when sleeping. It is hard to sleep with the AC on. Staff were very pleasant and accommodating. Free drinks on check in and check out, no nasty surprises with the resort fee, which is $21.50. Breakfast options were limited, consisting of fruit (melon and pineapple), mini-pastries, granola yoghurt pots and waffles. Instant coffee in flasks. Waffles were made fresh by the staff. Plenty of cats were roaming around the resort. Extras: Only a small car park was available, with about 6 spaces. It costs $30 to park here overnight, but there is street parking available outside for $6/hr between 8am-10pm. You can hire bikes to explore Key West for $15 per day. Location: Very lively location, best location, right in the heart of all the shops, bars and cafes, walking distance to all the attractions.
Price per night from:CAD 155

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:CAD 186

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:CAD 191

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:CAD 318

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:CAD 209

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:CAD 171

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:CAD 158

The Reach Key West, Curio Collection by Hilton

8.4/10
Very Good
Posted on Oct 30, 2025
Guest User
The hotel was great, clean and with all the necessary. The service at the restaurant was rather slow. The main remark relates to lack of clarity from Trip and the hotel on added costs: valet parking is ”mandatory” as the hotel doesn't allow guests to self park. This comes at a (hidden) cost of 50 usd per day plus taxes. The manager didn't mention this when we asked about the big deposit they were taking on our credit card. Unfortunate surprise contrasting with the wonderful time we had at the hotel.
Price per night from:CAD 246

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:CAD 149

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:CAD 300

Frequently Asked Questions

What are the best hotels with Swimming Pools in Key West?

How much is a hotel with Swimming Pools in Key West?

For hotels with Swimming Pools in Key West, the average price on weekdays is CAD 790, and on weekends (Friday–Saturday) is CAD 918.

What available deals for hotels with Swimming Pools in Key West?

Trip.com always provides various promotions and discounts for both new and loyal users. You can check the promotions page to figure out what promotions are available for your stay.

What are some of the best luxury hotels with Swimming Pools in Key West?

There are many luxury hotels with Swimming Pools in Key West. Casa Marina Key West, Curio Collection by Hilton (from CAD 256) is very popular.

Key West Hotels with Pools Information

Total properties156
Number of reviews8,653
Highest priceCAD 3,285
Lowest priceCAD 185
Weekday Avg. PriceCAD 790
Weekend Avg. PriceCAD 918