Islamorada

Hotels with Rooftop Pools in Islamorada

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23 Islamorada hotels with Rooftop Pools

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Closest to downtown
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56
Hotels in Islamorada
With a stay at Breezy Palms Resort in Islamorada (Matecumbe), you'll be within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park. This beach aparthotel is 1.4 mi (2.3 km) from Hurricane Monument and 1.6 mi (2.6 km) from Florida Keys Brewing Co.. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. This aparthotel also features complimentary wireless internet access, gift shops/newsstands, and tour/ticket assistance. Featured amenities include luggage storage, laundry facilities, and a safe deposit box at the front desk. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 40 guestrooms, featuring kitchens with full-sized refrigerators/freezers and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include separate sitting areas and coffee/tea makers, and housekeeping is provided weekly.

"We had an amazing relaxing time at Breezy Palms resort!!! We stayed in a 1st floor ocean front apartment that was recently updated, very clean and had a great view of the ocean. Nice to have the full kitchen-used every day. Bathroom was just right and had great shower! Bed was comfortable and great sheets!Screened lanai was perfect. Pool was wonderful, clean and warmer than the ocean! There is nice small beach with sand here. We didn’t get a chance to use the outdoor BBQs, but they looked well maintained, clean, and had everything for grilling. Office staff was friendly and helpful. Fully stocked on site store with bait, snacks, clothing, bottled soft drinks, Blue Bunny ice cream treats, and toiletries. Great maintenance throughout the resort. Although on Route 1, we didn’t hear the highway - lots of roosters and birds chirping. Iguanas were cool to see every day. They have a great dock to fish off of and we did fish for the last 3 days (got a 3 day salt water shore fishing license from nearby bait & tackle store) off the concrete dock and caught a grunt, pinfish, & 28” tarpon - all released. This location was great for seeing all of the keys because it’s a mile marker 80. Walking to nearby restaurants, marina and bridge to see sunset was within 1/4 mile - we could have used the bicycles, but didn’t bring the right footwear for biking. Breezy Palms resort was awesome!! Definitely a place for everyone - couples, families & solo travelers."
Very Good
101 reviews
8.4/10
1 night
From US$98
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99+
Hotels in Islamorada
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. This beach resort is 1 mi (1.7 km) from Hurricane Monument and 1.3 mi (2.1 km) from Florida Keys Brewing Co.. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and bicycles to rent. Additional amenities at this resort include wedding services and a picnic area. Guests can catch a ride to nearby destinations on the complimentary area shuttle. Take advantage of the resort's room service (during limited hours). Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 11:00 AM for a fee. Featured amenities include a 24-hour front desk and a water dispenser. Make yourself at home in one of the 55 individually decorated guestrooms, featuring kitchenettes with refrigerators and microwaves. Your pillowtop bed comes with Egyptian cotton sheets. Cable television is provided for your entertainment. Conveniences include phones, as well as safes and desks.

"Las instalaciones estaban un poco sucias y viejas y en la cocina no colocan ningún utensilio. Además estaban en remodelación."
Very Good
102 reviews
8.5/10
1 night
From US$216
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99+
Hotels in Islamorada
Welcome to Cheeca Lodge & SpaTurquoise water. Towering palms. Calm breezes. Imagine yourself whisked away to a tropical paradise where you indulge in mind, body, and spirit, as you rediscover an oasis called Cheeca Lodge & Spa. Romantic, serene, and dynamic, our Florida Keys Islamorada resort is a standard of excellence achieved by few. Be swept away by the casual elegance emanating from every detail and settle into the laid-back lifestyle of Islamorada.Stay in the Sportfishing Capital of the WorldLocated in the Sportfishing Capital of the World, Cheeca Lodge is a premier destination for serious anglers. Charter a boat and find over 500 species of fish within minutes from shore. The casual fisherman can cast a line from the end of our 525-foot pier – the longest in the Keys. A host of other activities can be found at our Islamorada luxury resort, including snorkeling, sea kayaking, bicycling, and scuba diving. Between activities, enjoy first-class dining at one of our three restaurants: Atlantic’s Edge, Mia Cucina, or Nikai Sushi.

"We had a wonderful stay at Cheeca Lodge! The staff was super friendly, the rooms very clean and the amenities were amazing! The food on resort was tasty and well made, too! We also indulged in a couples massage that was so relaxing - we will definitely be back!"
Great
105 reviews
9.1/10
1 night
From US$207
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64
Hotels in Islamorada
With a stay at Sunset Inn in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 8 minutes by foot from Keys History & Discovery Center. This hotel is 0.5 mi (0.9 km) from Matecumbe United Methodist Church and 0.8 mi (1.3 km) from History of Diving Museum. Enjoy recreation amenities such as an outdoor pool or take in the view from a garden. Additional features at this hotel include complimentary wireless internet access, a picnic area, and barbecue grills. Featured amenities include luggage storage and a safe deposit box at the front desk. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature complimentary toiletries and bidets. Conveniences include laptop-compatible safes and blackout drapes/curtains, and housekeeping is provided daily.

"Its decent but its not easy to find in the evening or night when its dark. Would help if it has a bright sign for the Inn. It has a pool at the back and you can hear the noise if people are partying out there but it seems to quiet down fortunately for us for the day we were there."
Very Good
102 reviews
8.6/10
1 night
From US$147
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99+
Hotels in Islamorada
With a stay at Caloosa Cove Resort by CoolVacay in Islamorada (Matecumbe), you'll be a 3-minute walk from Sunset Drive Beach and 6 minutes by foot from Anne's Beach. This condo is 3.9 mi (6.2 km) from Robbie’s of Islamorada and 4.2 mi (6.8 km) from Fiesta Key. Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and a picnic area. At Caloosa Cove Resort by CoolVacay, enjoy a satisfying meal at the restaurant. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 30 air-conditioned rooms featuring kitchens. Rooms have private balconies. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, as well as separate sitting areas and coffee/tea makers.
Very Good
43 reviews
8.9/10
1 night
From US$172
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99+
Hotels in Islamorada
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 7 minutes by foot from Islamorada Brewery & Distillery. This beach hotel is 0.4 mi (0.7 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from Florida Keys Brewing Co.. Spend the day on the private beach or dip into one of the 2 outdoor pools. Additional features at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite at Tides Beachside Bar, one of the hotel's 3 restaurants. Relax with a refreshing drink at the beach bar, the poolside bar, or one of 2 bars/lounges. Full breakfasts are available daily from 7:00 AM to 11:00 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Event facilities at this hotel consist of a conference center and 13 meeting rooms. Free self parking is available onsite. Stay in one of 114 guestrooms featuring Smart televisions. Rooms have private lanais. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.

"Nice hotel rooms that you can drive up to. Nice amount of space—although the bathroom is very small. Pool area is ok, not enough umbrellas. Didn’t get water everyday despite being told it was included with the resort fee. The access to the sea isn’t great. Yoga was fantastic."
Great
102 reviews
9.1/10
1 night
From US$246
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99+
Hotels in Islamorada
Welcome to Three Waters Resort & Marina, a one-of-a-kind destination named for the rare meeting of the Atlantic Ocean, Florida Bay, and the Gulf of Mexico. Set on 15 waterfront acres in Islamorada—the “Sportfishing Capital of the World”—our resort blends island adventure with serene relaxation. Relax in a range of island-inspired guestrooms and cottages, or retreat to The Cove, our adult-focused oasis with a private beach lagoon. Discover tropical beauty and the spirit of the Florida Keys, plus nine unique dining options—from the wood-fired warmth of Kindler to the iconic Tiki Bar. Cruise between experiences aboard our water taxi, Rum Runner. At our full-service marina, a seasoned fleet of captains welcomes anglers of every level. Whether you’re seeking world-class fishing, a family vacation, romantic escape, upscale retreat, or a dream beach wedding, Three Waters Resort & Marina is your ultimate Florida Keys escape.

"The resort was very beautiful and well maintained. The cottage we stayed in was spacious and we really liked the decor and how soft the beds were. The food was good but a little pricey. We were not impressed with the cabana rental. The cabana was not ready when we arrived. We had to wait for it to be cleaned and set up. The cabana was not labeled and we were confused on which cabana was ours as there were 2 next to each other. We asked when service would start and we were told 10am, then we asked again at 10:45, then went to the front office at 11:30 and when 12pm rolled around with no service we decided to leave and get our money back on the cabana. At that point all we paid for was a chair and towel which did not meet our expectation when spending $250.00 on a cabana for the day. I would recommend several things for the cabana. 1. Number the cabanas so you can clearly see the number. Telling us Cabana 2 does not help when they are beside each other. 2. Stock the min fridge with water. 3. Clearly explain on the cabana rental that food/service will not start until a certain time. We expected to at least get something to drink while in the cabana. 4. Install a call button or app that you can be in contact with someone when you need something. There was a significant delay on getting our refund. And we do appreciate the Manager helping us on Friday get that resolved before we checked out on Saturday morning. All in all, the resort was great. We loved the vibe and updates made to the property. The rooms were comfortable and fresh, and we loved the beds as they were very comfortable, and the sheets were so soft. Everyone was friendly and pleasant. We most enjoyed fish like a local with Patrick. We found that the pool in the middle of the property was less used and felt more quiet and more private therefore we spent our time with a good book. I would give the stay at 4.5 out of 5. Highly recommend trying out Three Waters Resort."
Very Good
79 reviews
8.9/10
1 night
From US$329
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99+
Hotels in Islamorada
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing Co.. This beach resort is 4.8 mi (7.6 km) from Windley Key Fossil Reef Geological State Park and 6.5 mi (10.4 km) from Anne's Beach. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and a fitness center. This resort also features gift shops/newsstands, wedding services, and a television in a common area. Grab a bite at ReelCatch, one of the resort's 2 restaurants, or stay in and take advantage of the room service (during limited hours). Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 6:00 AM to 11:00 AM for a fee. Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Make yourself at home in one of the 110 air-conditioned rooms featuring flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include safes and desks, as well as phones with free local calls.

"Ameracay is a very nice resort. It's not too far and easily accessible. It gas a nice tiki brand beach as well as a very nice courtyard with game areas and firepits. The resort is in an area that has iguanas. These are harmless if left alone. Make sure yiu balcony door is shut so a curious iguana does not visit. You also should ve aware that in case of a cold snap, iguanas fall from trees. As long as they don't hit you in the head again they are harmless. Visited the outside bar fi a sandwich. Everything in the Keys cost more so prices are moderate. We shared a sandwich with no issues. The lobby area is very nice with suspended swinging chairs. Decorations are ”islandish” which is appropriate. There is a selfie wall which has keys mounted. There is also a wall mounted magnetic Scrapple game. There are nice restaurants within walking distance. Both Midway and Lazy Boys were busy. If you go out for dinner, expect moderate wait. Staff was exceptionally nice and helpful. The resort has a very snLl gift shop. Not much for men unless you need a bathing suit. The only problem was the entire area was having water issues. There was no hot water in the room. I would stay again. It's about half the cost of staying in Key West. There are places very close by if you want to plY in, on, or under the water. It may be possible to book a ride out to Alligator Reef Lighthouse via a service near by. Lots of places to hop on a fishing boat. The water off Islamadora is a nationally protected coral reef. Make sure you know what you can and can't do on the reef. The resort does not allow drone flying on property. You might be able to fly from a nearby bridge. I will probably visit again."
Very Good
103 reviews
8.6/10
1 night
From US$184
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99+
Hotels in Islamorada
A stay at Fisher Inn Resort & Marina places you in the heart of Islamorada, a short 3-minute walk from Windley Key Fossil Reef Geological State Park and within 3 minutes by car from Rain Barrel Village. This beach motel is 1.9 mi (3.1 km) from History of Diving Museum and 2 mi (3.2 km) from Founders Park. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool. Additional amenities at this Art Deco motel include complimentary wireless internet access, concierge services, and gift shops/newsstands. A complimentary on-the-go breakfast is served daily from 8:00 AM to 10:30 AM. Featured amenities include express check-out, luggage storage, and coffee/tea in a common area. Free self parking is available onsite. Make yourself at home in one of the 22 individually decorated guestrooms, featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and irons/ironing boards, and housekeeping is provided on request.

"The reception staff were lovely, so welcoming and helpful. Little heated pool and nice sun loungers, just missing some umbrellas to make it perfect. The outside grill was great to use and clean. Room didn’t get cleaned during our two night stay though… 🤷🏼♀️"
103 reviews
7.5/10
1 night
From US$135
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99+
Hotels in Islamorada
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 10 minutes by foot from Keys History & Discovery Center. This hotel is 0.6 mi (1 km) from Matecumbe United Methodist Church and 0.7 mi (1.1 km) from History of Diving Museum. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities, which include an outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a picnic area. The front desk is staffed during limited hours. Limited parking is available onsite. Make yourself at home in one of the 20 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with showers are provided. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

"Bella struttura ristrutturata sapientemente, stanza ampia ed accogliente, zona esterna bella e suggestiva soprattutto al tramonto."
Very Good
102 reviews
8.9/10
1 night
From US$170
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See All Hotels With Rooftop Pools in Islamorada

FAQs

What are the top hotels in Islamorada near History of Diving Museum?

Some of the top hotels in Islamorada near History of Diving Museum include Hadley Resort and Marina (from US$140), Islander Resort (from US$242) and La Jolla Resort (from US$176), all offering easy access to History of Diving Museum, making them ideal for visitors looking to explore the area.

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

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Islamorada this weekend is US$512 per night. For a 4-star hotel, the average cost is US$661 per night. If you're looking for a luxury experience, 5-star hotels in Islamorada this weekend typically cost US$790 per night.

How much do hotels in Islamorada cost per day during weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Islamorada during weekdays is US$371 per night. For a 4-star hotel, you can expect to pay around US$575 per night. If you're seeking a luxury stay, 5-star hotels in Islamorada generally cost US$509 per night on weekdays.

What are the best hotels with a spa in Islamorada?

Planning a relaxing getaway? A spa experience can be the perfect addition to your trip. Cheeca Lodge & Spa (from US$221) provides highly rated spa services for ultimate relaxation.

Which hotels in Islamorada have pools?

Islander Resort (from US$242), Cheeca Lodge & Spa (from US$221) and La Siesta Resort & Villas (from US$251) are popular hotels with swimming pools. Stay at any of these hotels to enjoy a swimming pool!

What are the best places to stay in Islamorada?

Some of the best places to stay in Islamorada are near popular attractions like History of Diving Museum, Theater of the Sea and Founders Park Soccer Fields, offering easy access to key sights and amenities.

What hotels in Islamorada offer an especially good breakfast?

Cheeca Lodge & Spa (from US$221), Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort (from US$249) and Islander Resort (from US$242) offer an especially good breakfast to start your day. Begin your day with a tasty and satisfying breakfast!

How to get good deals on hotels in Islamorada?

Trip.com provides various promotions, discounts and special offers all year round. You can check the promotions page for the latest promotions on Trip.com.