Key West

Hotels with Rooftop Pools in Key West

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91 Key West Hotels with Rooftop Pools Found for You

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Andrews Inn & Garden Cottages
Andrews Inn & Garden CottagesAndrews Inn & Garden CottagesAndrews Inn & Garden CottagesAndrews Inn & Garden CottagesAndrews Inn & Garden CottagesAndrews Inn & Garden Cottages
99+
Hotel near Duval,Key West
With a stay at Andrews Inn & Garden Cottages in Key West (Old Town Key West), you'll be steps from Duval Street and 2 minutes by foot from Ernest Hemingway Home and Museum. This bed & breakfast is 0.3 mi (0.5 km) from Florida Keys Beaches and 0.4 mi (0.6 km) from Southernmost Point. Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional amenities at this Colonial bed & breakfast include complimentary wireless internet access, concierge services, and a vending machine. A complimentary self-serve breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include express check-in, express check-out, and luggage storage. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 6 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have showers and hair dryers. Conveniences include minibars and ceiling fans, and housekeeping is provided daily.
Amazing
51 reviews
9.6/10
1 night
From US$282
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Fairfield Inn & Suites Key West at the Keys Collection
Fairfield Inn & Suites Key West at the Keys CollectionFairfield Inn & Suites Key West at the Keys CollectionFairfield Inn & Suites Key West at the Keys CollectionFairfield Inn & Suites Key West at the Keys CollectionFairfield Inn & Suites Key West at the Keys CollectionFairfield Inn & Suites Key West at the Keys Collection
99+
Hotels in Key West
Discover the vibrant culture of the island at Fairfield Inn and Suites Key West at the Keys Collection. Conveniently located near Key West International Airport, your vacation begins the moment you land. We are thrilled to unveil our newly renovated downtown Key West hotel, bringing a fresh and contemporary look to your island experience. Explore local hotspots like Duval Street, Old Town and Mallory Square, all conveniently located near our NAS Key West hotel. Start your day in Key West, Florida with our complimentary breakfast, enjoy a workout in our fitness center or take a refreshing dip in our outdoor pool. With more than 11,000 square feet of event space, our hotel near Key West Airport remains the ideal choice for special celebrations, weddings and other events. At Fairfield Inn and Suites Key West at the Keys Collection, your comfort and satisfaction are our top priorities. In fact, we are proud to uphold the Fairfield 100 percent guarantee we promise you will be satisfied or we will make it right.

"There were an issue with the system but the the staff improved and resolve very fast. Very clean place, comfortable, quiet and Great location. I will definitely go back again"
Very Good
129 reviews
8.2/10
1 night
From US$101
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Duval House
Duval HouseDuval HouseDuval HouseDuval HouseDuval HouseDuval House
99+
Hotel near Duval,Key West
With a stay at Duval House in Key West (Old Town Key West), you'll be steps from Duval Street and 3 minutes by foot from Ernest Hemingway Home and Museum. This bed & breakfast is 0.5 mi (0.7 km) from Florida Keys Beaches and 0.5 mi (0.8 km) from South Beach. Take advantage of recreation opportunities such as bicycles to rent or take in the view from a terrace and a garden. Additional amenities at this bed & breakfast include concierge services, wedding services, and a picnic area. Featured amenities include express check-in, express check-out, and complimentary newspapers in the lobby. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 29 air-conditioned rooms featuring flat-screen televisions. Cable television is provided for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers.

"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."
Very Good
101 reviews
8.9/10
1 night
From US$148
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Key West
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Hyatt Centric Key West Resort and Spa
Hyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and SpaHyatt Centric Key West Resort and Spa
99+
Hotel near Downtown Key West,Key West
Caribbean style resort with open air piazza situated on the Gulf of Mexico in the heart of old town Key West. Offering 118 guest rooms with tiled entry foyers, private balconies, ceiling fans, some rooms offer a partial water view. The dress code throughout the island is casual resort wear.

"The hotel for more than 6,000 nights is only part of the sea view, and the rest is the small beach of other houses, simple cars, and the scenery. The room is clean and tidy, and the bed is big and comfortable, but the noise of the air conditioner seriously affects sleep. The hotel’s seaside restaurant is good, while enjoying the food, watching the sunset."
Very Good
108 reviews
8.6/10
1 night
From US$262
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The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key WestThe Perry Hotel & Marina Key WestThe Perry Hotel & Marina Key WestThe Perry Hotel & Marina Key WestThe Perry Hotel & Marina Key WestThe Perry Hotel & Marina Key West
99+
Hotels in Key West
When you stay at The Perry Hotel & Marina Key West in Key West, you'll be on the waterfront, within a 5-minute drive of Stock Island Yacht Club & Marina and Key West Golf Club. This hotel is 4.9 mi (7.9 km) from Clarence S. Higgs Memorial Beach Park and 5 mi (8.1 km) from Ernest Hemingway Home and Museum. Dip into one of the 2 outdoor swimming pools or enjoy other recreational amenities including a 24-hour fitness center and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite with seafood at Matt's Stock Island, one of the hotel's 2 restaurants. Wind down with a drink at one of the 2 bars/lounges or 2 poolside bars. Cooked-to-order breakfasts are available daily from 8:00 AM to 11:30 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Planning an event in Key West? This hotel has 700 square feet (65 square meters) of space consisting of conference space and a meeting room. Self parking (subject to charges) is available onsite. Stay in one of 100 guestrooms featuring flat-screen televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature designer toiletries and hair dryers.

"This time the departmental group went to Dujiangyan, and then chose this newly opened Hampton by Hilton hotel. The location of the hotel is very good. Chengdu has been driving for over an hour. The location is in Dujiangyan City. It is close to some must-see attractions, such as Nanqiao and Yulei Mountain Park. There are also a lot of food nearby, hot pot restaurants, barbecue. The room was unexpectedly comfortable and warm. The check-in efficiency at the front desk is also good, and there are three breakfast options to be delivered to the room during yq, which is very intimate. The price / performance ratio is also very high. I will still choose this place when I bring my family over next time ~"
Great
105 reviews
9.2/10
1 night
From US$107
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La Concha Key West
La Concha Key WestLa Concha Key WestLa Concha Key WestLa Concha Key WestLa Concha Key WestLa Concha Key West
99+
Hotel near Duval,Key West
Nestled in the heart of Key West, La Concha Key West is a beacon of timeless elegance and contemporary comfort. This iconic destination, celebrated for its rich historical significance and vibrant local culture, offers guests an unparalleled experience of luxury and adventure. From our luxurious accommodations and pet-friendly amenities to our outdoor pool and exclusive rooftop terrace for breathtaking sunsets and handcrafted cocktails, every detail is curated to captivate your senses and inspire unforgettable moments. Whether exploring Old Town's enchanting streets, basking in the sun at nearby Key West beaches, or walking to Mallory Square, Sunset Pier, and the nightlife on Duval Street, La Concha Key West is your gateway to the ultimate island escape. Home to Tropicado, Perla, and El Dom, offering Cuban-inspired culinary experiences that celebrate local flavor with a twist. Discover the perfect blend of historic charm and modern sophistication, all wrapped in the laid-back luxury Key West is famous for.

"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!"
Very Good
110 reviews
8.4/10
1 night
From US$233
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The Mermaid & The Alligator
The Mermaid & The AlligatorThe Mermaid & The AlligatorThe Mermaid & The AlligatorThe Mermaid & The AlligatorThe Mermaid & The AlligatorThe Mermaid & The Alligator
99+
Hotel near Downtown Key West,Key West
Located in Key West (Old Town Key West), The Mermaid & Alligator is within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. This guesthouse is 0.6 mi (0.9 km) from Florida Keys Beaches and 0.6 mi (1 km) from South Beach. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional amenities at this Victorian guesthouse include complimentary wireless internet access and concierge services. A complimentary full breakfast is served daily from 8:30 AM to 10:00 AM. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 9 air-conditioned guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms feature bathtubs or showers, hair dryers, and bathrobes. Conveniences include safes and ceiling fans, and housekeeping is provided daily.
Amazing
100 reviews
9.6/10
1 night
From US$208
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Hyatt Vacation Club at Windward Pointe
Hyatt Vacation Club at Windward PointeHyatt Vacation Club at Windward PointeHyatt Vacation Club at Windward PointeHyatt Vacation Club at Windward PointeHyatt Vacation Club at Windward PointeHyatt Vacation Club at Windward Pointe
57
Hotels in Key West
With a stay at Hyatt Vacation Club at Windward Pointe, Key West in Key West, you'll be near the airport, within a 15-minute walk of Fort East Martello Museum and Gallery and Key West Art and Historical Society. This hotel is 1.2 mi (1.9 km) from Smathers Beach and 3.5 mi (5.6 km) from Duval Street. Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and bicycles to rent. This hotel also features complimentary wireless internet access, concierge services, and babysitting (surcharge). You can enjoy a meal at the restaurant serving the guests of Hyatt Vacation Club at Windward Pointe, Key West, or stop in at the snack bar/deli. Featured amenities include a safe deposit box at the front desk and an elevator. Free self parking is available onsite. Make yourself at home in one of the 93 guestrooms, featuring kitchens with refrigerators and stovetops. Rooms have private balconies. Complimentary wireless internet access keeps you connected, and DVD players are provided for your entertainment. Bathrooms with separate bathtubs and showers feature jetted bathtubs and complimentary toiletries.

"It is the second time and as always very good . All staff very careful and friendly . Exceptional cleaning , just that the hydromassage bathroom did not work but as we were short time don't call the reception to say it , but everything else always perfect"
Great
104 reviews
9.2/10
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Eden House
Eden HouseEden HouseEden HouseEden HouseEden HouseEden House
99+
Hotel near Downtown Key West,Key West
Located in Key West (Key West Historic District), Eden House is within a 15-minute walk of Duval Street and Florida Keys Beaches. This hotel is 1.1 mi (1.7 km) from Mallory Square and 1.4 mi (2.2 km) from Southernmost Point. Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and bicycles to rent. This Art Deco hotel also features complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite with Mediterranean cuisine at Azur, a restaurant which features a bar/lounge. Dining is also available at the coffee shop/cafe. Wrap up your day with a drink at the poolside bar. Featured amenities include complimentary wired internet access, a computer station, and express check-in. Guests may use a ferry terminal shuttle for a surcharge, and limited parking is available onsite. Make yourself at home in one of the 39 individually decorated guestrooms, featuring microwaves and Smart televisions. Your room comes with a pillowtop bed. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and hair dryers.

"This was an awesome experience. Hotel was nice and quaint. Only thing I didn't like was we didn't have anyplace to hang our clothes up or put things away. Near Duval street and downtown. Pool area was well kept. Staff was very friendly. If I stay for longer than one night I will definitely look into a bigger room. Close to beaches, shops, dining. I would stay again for the price it was worth while."
Very Good
102 reviews
8.8/10
1 night
From US$134
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Margaritaville Beach House Key West
Margaritaville Beach House Key WestMargaritaville Beach House Key WestMargaritaville Beach House Key WestMargaritaville Beach House Key WestMargaritaville Beach House Key WestMargaritaville Beach House Key West
99+
Hotels in Key West
Located in Key West, Margaritaville Beach House Key West is by the ocean, within a 5-minute drive of Smathers Beach and Fort East Martello Museum and Gallery. This beach hotel is 1.3 mi (2 km) from Clarence S. Higgs Memorial Beach Park and 2.2 mi (3.5 km) from South Beach. Don't miss out on the many recreational opportunities, including an outdoor pool, a 24-hour fitness center, and bicycles to rent. This hotel also features concierge services and a banquet hall. Enjoy a meal at the restaurant, or stay in and take advantage of the hotel's room service (during limited hours). Quench your thirst with your favorite drink at the bar/lounge. Cooked-to-order breakfasts are available daily from 7:30 AM to 11:00 AM for a fee. Featured amenities include a business center, dry cleaning/laundry services, and a 24-hour front desk. This hotel has 3 meeting rooms available for events. Make yourself at home in one of the 186 air-conditioned rooms featuring microwaves. Digital television is provided for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include safes and complimentary bottled water, as well as phones with free local calls.

"It’s too far out from the main area although there’s a shuttle into town. All our clothes smelt damp after just 4 days of being there. The room felt very damp the bed especially. Pool is ok but I’m sure you’d struggle to get a sun bed in high season. The beach is nice across the street but the sunbeds are rentable from a company $$$"
Very Good
104 reviews
8.5/10
1 night
From US$171
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See All Hotels With Rooftop Pools in Key West

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Where can you find hotels with excellent breakfast in Key West?

What are some hotels with pools in Key West?

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Where can I find the best hotel discounts in Key West?

Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.

Which hotels are recommended near Key West in Key West?

For Key West hotels near Key West, many travelers recommend The Grand Guesthouse (from US$166), Fairfield Inn & Suites Key West (from US$144) and The Palms Hotel (from US$141) for their great location and service.

What is the average price of hotels in Key West for this weekend?

The average hotel prices in Key West for this weekend are as follows:
3-star hotels: US$814
4-star hotels: US$1,404
5-star hotels: US$884

What is the average price of hotels in Key West on weekdays?

On average, weekday hotel prices in Key West are:
3-star hotels– US$681
4-star hotels– US$1,228
5-star hotels– US$712