Key West

Hotels with Rooftop Pools in Key West

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86 Key West Hotels with Rooftop Pools Found for You

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Closest to downtown
Highest Rated
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.

"I had a hard time locating the hotel because the address is N. Roosevelt, but the entrance to the hotel is after the road becomes S. Roosevelt. When I walked around my room barefoot, I got dirt on my feet that the carpet hid. The lighting in the bathroom wasn't bright enough to see my face closely enough to shave. The breakfast was good. The pool was nice. I was concerned when I saw earplugs on my nightstand with a card saying the neighbors could get a little noisy; thankfully I had a quiet night."
Very Good
133 reviews
8.4/10
1 night
From US$143
Check availability
99+
Hotels in Key West
Nestled along the Florida Bay, a short drive from historic Old Town Key West, Florida, this property offers an outdoor pool, casual cafe and a variety of activities.Parrot Key Hotel & Villas is surrounded by lush landscaping and gardens. Guests can go for a swim in one of the 4 outdoor pools, then enjoy a snack from the poolside The Grove Kitchen & Bar. The property is completely nonsmoking.Guests at the Parrot Key Hotel & Villas can spend the day kayaking. After a kayaking trip, guests can relax with an on-site massage or take the complimentary shuttle to the historic Key West old town city center.A 55-inch flat-screen TV and small fridge are featured in each accommodations at the Parrot Key Hotel & Villas. Guests can relax on their private terrace and enjoy views of the ocean and tropical landscape.

"I stayed here for one night. It is a little far from the old town, which is the center of tourism, but if you plan on spending time at the pool, it's fine. The facilities are new, the room was clean and comfortable, but the water pressure in the bathroom felt a little weak."
Very Good
119 reviews
8.3/10
1 night
From US$147
Check availability
99+
Hotels in Key West
Daily Resort Charge includes: Shuttle service to Old Town Key West; two daily in-room bottled waters; beach amenities (chairs, umbrella & cooler); 20% off bicycle rentals for two; 10% off golf cart rentals; arts & crafts for kids. The best of Key West in easy reach We're off Highway 1, three miles from Duval Street and Smathers Beach, and walking distance from restaurants. The Ernest Hemingway House and Old Town can be reached in about 10 minutes, and Mallory Square is only four miles from our door. Enjoy our restaurant, outdoor pool bar, available downtown shuttle service, and 24-hour convenience shop.

"The shuttle bus runs once an hour. You need to make an appointment for the outbound trip. The return trip will be full if it is too crowded. The room is very old and stained everywhere. It is a cheap hotel on the island. The quality is average. Breakfast is 18 yuan per person. There is no need to buy it. It is not cost-effective."
Very Good
129 reviews
8.2/10
1 night
From US$123
Check availability
99+
Hotels in Key West
With a stay at Havana Cabana at Key West in Key West (New Town), you'll be a 5-minute drive from Florida Keys Beaches and 6 minutes from Duval Street. This hotel is 3.2 mi (5.1 km) from Southernmost Point and 3.4 mi (5.5 km) from Mallory Square. Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and complimentary use of a nearby fitness facility. You can enjoy a meal at Floridita Food Truck serving the guests of Havana Cabana at Key West , or stop in at the snack bar/deli. Relax with your favorite drink at the bar/lounge or the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 10 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Free self parking is available onsite. Make yourself at home in one of the 106 individually decorated guestrooms, featuring refrigerators and microwaves. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include safes and desks, and housekeeping is provided daily.

"Hotel had a great vibe, filled with plants and was very colorful in the lobby, a true feeling to the name, Havana cabana. The pool was the best part, so clean and had inner tubes to float around and relax. Two complimentary drink passes during check in was a plus. Food was excellent for lunch and breakfast. We went as a family trip so the only downside was there weren't a lot of kids. At one point we thought it was ”adult only” but then towards the later afternoon we started to see more kids. Rooms were clean and service was good. Definitely will stay again."
Very Good
112 reviews
8.6/10
1 night
From US$151
Check availability
99+
Hotel near Downtown Key West,Key West
With a stay at Opal Key Resort & Marina, Key West, you'll be centrally located in Key West, steps from Mallory Square and 3 minutes by foot from Duval Street. This hotel is 0.3 mi (0.5 km) from Florida Keys Beaches and 0.7 mi (1.1 km) from Ernest Hemingway Home and Museum. Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a 24-hour fitness center. This hotel also features concierge services and a banquet hall. At Opal Key Resort & Marina, Key West, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 7:00 AM to 10:00 AM for a fee. Featured amenities include a 24-hour business center, dry cleaning/laundry services, and a 24-hour front desk. This hotel has 11 meeting rooms available for events. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 178 air-conditioned rooms featuring flat-screen televisions. Cable television is provided for your entertainment. Bathrooms feature bathtubs or showers with rainfall showerheads and complimentary toiletries. Conveniences include safes and desks, as well as phones with free local calls.

"This hotel is a kind of more lively hotel, just at the cruise terminal. In the morning breakfast, there will be cruise ships of major cruise companies coming and parked, and will drive away in the afternoon! The hotel's people are all foreign friends and buddies come together for a holiday party, the pool is very lively, the pool view room will be noisy at night! Sea view room is ok! I feel that it is not so suitable for a family to bring children, if a few families bring children together! It's convenient to go anywhere, needless to say! But to say that it is convenient, there is not much in the center of Key West, which is very convenient! The hotel is good because of its location, so the price is not high! Nothing else to say, the service level is first class! Sea view room can see the setting sun!"
Great
100 reviews
9.0/10
1 night
From US$265
Check availability
99+
Hotels in Key West
Daily Resort Charge includes: Guest internet access; shuttle service to airport, downtown and beach; access to Sunset Watersport Beach Club; 2 reusable water bottles refillable at stations throughout resort; morning coffee bar in the lobby. Enjoy the laid back atmosphere of the Florida Keys, one of the world's most popular destinations. Surrounded by the tropical beauty, charm, and colorful character of Key West, business travelers and vacationers alike appreciate the resort's 216 guest rooms and suites. Enjoy the comforts of home and all the conveniences of a full-service resort. DoubleTree by Hilton Grand Key Resort features on-site dining and a tiki bar, zero entry pool and cabanas, full convention and catering facilities with function space for up to 200, a shuttle service, 24-hour fitness center, and ample parking.

"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 😉"
Very Good
45 reviews
8.6/10
1 night
From US$127
Check availability
56
Hotels in Key West
With a stay at The Laureate Key West in Key West (New Town), you'll be within a 10-minute drive of Duval Street and Florida Keys Beaches. This beach hotel is 3.4 mi (5.4 km) from Southernmost Point and 2.8 mi (4.5 km) from Smathers Beach. Enjoy recreational amenities such as an outdoor pool and an indoor pool. This hotel also features concierge services, gift shops/newsstands, and a television in a common area. Featured amenities include a 24-hour business center, express check-out, and complimentary newspapers in the lobby. Make yourself at home in one of the 64 individually decorated guestrooms, featuring kitchenettes with refrigerators and stovetops. 55-inch flat-screen televisions are provided, with digital programming available. Conveniences include safes and desks, as well as phones with free local calls.

"The room has a very beautiful color scheme. The sea is just across the road from the window. The view is beautiful and not noisy at night. There is a small living room (with a sofa bed) and a kitchen. The kitchenware is complete and very practical. There is a free parking space and it is also close to the supermarket. It only costs a dozen dollars to take a taxi to popular attractions (such as Hemingway's former residence). The only problem is that the quilt at night is very thin, similar to a blanket, and it is a bit cold. You need to ask the hotel for an extra quilt. But overall, I am very satisfied and I will probably come again next time."
Very Good
111 reviews
8.9/10
1 night
From US$159
Check availability
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 Ernest Hemingway Home and Museum. This bed & breakfast is 0.5 mi (0.8 km) from Florida Keys Beaches and 0.5 mi (0.7 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."
Great
101 reviews
9.0/10
1 night
From US$127
Check availability
95
Hotels in Key West
Welcome to our oceanfront property, located just moments from Key West International Airport and Smathers Beach. We offer convenient and affordable accommodations for travelers looking to experience the beauty of the coast without sacrificing comfort or amenities. Take advantage of our complimentary shuttle service, which will transport you up to four miles to downtown attractions like Fort Zachary Taylor, Mallory Square, and the Southernmost Point of the Continental US. When you're ready to unwind, relax at Cheekie Hut, our poolside bar and grill. We offer a free hot breakfast and complimentary WiFi, so you can stay connected and energized throughout your stay. And, of course, you'll be treated to breathtaking views of the ocean from your room or suite. While we may not be situated directly on the beach, our location and amenities make us the perfect choice for your next Key West adventure.

"I chose the hotel instead of one in Key West because it offers a shuttle service to the center and has a larger pool. However, it was fully booked on our evening. We had to wait 2 hours and let 3 buses go. The shuttle back was just as full. We walked the long way back to the meeting point and then it left right in front of us without us. So if you're only staying 1-2 days, you're out of luck. The room was ultra dark but large. You can hear the planes very clearly during the day, and directly. They're big planes and they fly every 20 minutes. Otherwise, it's OK. Don't expect much from the breakfast, coffee is available all day in the lobby"
Very Good
116 reviews
8.7/10
1 night
From US$185
Check availability
65
Hotel near Downtown Key West,Key West
Minutes from the Key West Historic Seaport Fitch Lodge welcomes on-the-go explorers to authentic conch-house lodging in a neighborhood setting. Return from reef diving or deep-sea fishing to informal bohemian accommodations and a refreshing pool.
Very Good
100 reviews
8.6/10
1 night
From US$136
Check availability
See All Hotels With Rooftop Pools in Key West

FAQs

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

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Key West this weekend is US$585 per night. For a 4-star hotel, the average cost is US$1,357 per night. If you're looking for a luxury experience, 5-star hotels in Key West this weekend typically cost US$587 per night.

How much do hotels in Key West cost per night during weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Key West during weekdays is US$467 per night. For a 4-star hotel, you can expect to pay around US$998 per night. If you're seeking a luxury stay, 5-star hotels in Key West generally cost US$448 per night on weekdays.

What are the best places to stay in Key West?

Some of the best places to stay in Key West are near popular attractions like Key West, The Hemingway Home and Museum and Truman Little White House, offering easy access to key sights and amenities.

What are the top hotels in Key West near Key West?

Some of the top hotels in Key West near Key West include Authors Key West Guesthouse (from US$120), Casa Marina Key West, Curio Collection by Hilton (from US$180) and Silver Palms Inn (from US$130), all offering easy access to Key West, making them ideal for visitors looking to explore the area.

What is the best spa hotel in Key West?

What are some hotels with pools in Key West?

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

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.