Islamorada

Islamorada Hotels with Rooftop Pools

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23 Islamorada Hotels with Rooftop Pools Found for You

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Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Islamorada
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be a 4-minute walk from Indian Key Historic State Park and 11 minutes by foot from 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.

"Check in super easy.  Nice resort."
Very Good
102 reviews
8.4/10
1 night
From €138
Check availability
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.

"Great trip! We enjoyed it a lot! Great service, we love our room (ocean front) the only issue that we had is that we didn’t have access to internet through wifi"
Great
109 reviews
9.1/10
1 night
From €232
Check availability
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 phones, as well as separate sitting areas and coffee/tea makers.

"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 €68
Check availability
99+
Hotels in Islamorada
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 4 minutes by foot from Lorelei Restaurant & Cabana Bar. This beach hotel is 0.4 mi (0.7 km) from Islamorada Brewery & Distillery and 0.4 mi (0.7 km) from Matecumbe United Methodist Church. 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 €228
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99+
Hotels in Islamorada
With a stay at Pines & Palms Resort in Islamorada (Matecumbe), you'll be a 3-minute walk from Indian Key Historic State Park and 12 minutes by foot from Bud n' Mary's Dive Center. This beach hotel is 1 mi (1.6 km) from Hurricane Monument and 1.2 mi (1.9 km) from Florida Keys Brewing Co.. Relax on the private beach or enjoy other recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and wedding services. Take advantage of the hotel's room service. Need to unwind? Take a break at the bar/lounge, the beach bar, or the poolside bar for a tasty beverage. Featured amenities include limo/town car service, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 26 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. 50-inch flat-screen televisions with digital programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, and housekeeping is provided daily.
Great
100 reviews
9.2/10
1 night
From €205
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99+
Hotels in Islamorada
With a stay at Casa Morada in Islamorada (Matecumbe), you'll be a 5-minute walk from Islamorada Brewery & Distillery and 6 minutes by foot from Lorelei Restaurant & Cabana Bar. This beach hotel is 0.5 mi (0.8 km) from Keys History & Discovery Center and 0.6 mi (1 km) from Matecumbe United Methodist Church. Pamper yourself with onsite massages or enjoy recreation amenities such as an outdoor pool. Additional features at this hotel include complimentary wireless internet access and concierge services. Take advantage of the hotel's room service (during limited hours). A complimentary continental breakfast is served daily from 7 AM to 10:30 AM. 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 16 individually decorated guestrooms, featuring minibars and DVD players. Rooms have private balconies or patios. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms have designer toiletries and hair dryers.
Great
84 reviews
9.3/10
1 night
From €153
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99+
Hotels in Islamorada
With a stay at Hadley Resort and Marina in Islamorada (Matecumbe), you'll be within a 10-minute walk of Islamorada Brewery & Distillery and History of Diving Museum. This beach hotel is 0.7 mi (1.2 km) from Lorelei Restaurant & Cabana Bar and 0.8 mi (1.3 km) from Keys History & Discovery Center. 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 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, multilingual staff, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 37 air-conditioned rooms featuring refrigerators. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers.
Good
100 reviews
7.6/10
1 night
From €112
Check availability
99+
Hotels in Islamorada
With a stay at La Jolla Resort in Islamorada (Matecumbe), you'll be steps from Islamorada Brewery & Distillery and 9 minutes by foot from Lorelei Restaurant & Cabana Bar. This hotel is 0.5 mi (0.9 km) from Keys History & Discovery Center and 0.6 mi (1 km) from Matecumbe United Methodist Church. 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."
Great
102 reviews
9.0/10
1 night
From €106
Check availability
99+
Hotels in Islamorada
With a stay at The Islands of Islamorada in Islamorada (Matecumbe), you'll be within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. This beach villa is 0.8 mi (1.3 km) from Keys History & Discovery Center and 0.9 mi (1.4 km) from Lorelei Restaurant & Cabana Bar. Dip into one of the 2 outdoor pools or enjoy other recreational amenities including a 24-hour fitness center and 2 outdoor pickleball courts. This villa also features complimentary wireless internet access, concierge services, and wedding services. Wrap up your day with a drink at the poolside bar. Cooked-to-order breakfasts are available daily from 9:00 AM to 11:00 AM for a fee. The front desk is staffed during limited hours. Free self parking is available onsite. Make yourself at home in one of the 30 individually decorated guestrooms, featuring microwaves and Smart 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. Bathrooms feature showers with rainfall showerheads and designer toiletries.
Amazing
45 reviews
9.4/10
1 night
From €482
Check availability
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
8.5/10
1 night
From €142
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Frequently Asked Questions

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 €453 per night. For a 4-star hotel, the average cost is €565 per night. If you're looking for a luxury experience, 5-star hotels in Islamorada this weekend typically cost €566 per night.

How much do hotels in Islamorada cost per night 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 €281 per night. For a 4-star hotel, you can expect to pay around €478 per night. If you're looking for a luxury stay, 5-star hotels in Islamorada generally cost €428 per night on weekdays.

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 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 €94), Islander Resort (from €214) and Casa Morada (from €150), all offering easy access to History of Diving Museum, making them ideal for visitors looking to explore the area.

What are the best hotels with a spa in Islamorada?

Plan a peaceful trip? Spa can be a wonderful experience when traveling. Cheeca Lodge & Spa (from €148) provides highly rated spa services.

What hotels in Islamorada provide swimming pools?

La Siesta Resort & Villas (from €148), Islander Resort (from €214) and Cheeca Lodge & Spa (from €148) are hotels with swimming pools. Book now and enjoy your swimming pool!

Which hotels in Islamorada have the best breakfast?

What hotel deals are available in Islamorada?

Trip.com offers multiple promotions and discounts all year round for both new users and loyal customers . Please check the promotions page to see what promotions are available now on Trip.com.