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Hotels in Islamorada

Choose from 2198 Islamorada Hotel Deals

Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
  • 22 min walk from Theater of the Sea
The price is $291 per night from Apr 28 to Apr 29
$291
includes taxes & fees
Apr 28 - Apr 29
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
9/10 Wonderful! (1,427 reviews)
Nice Resort for the Money
"I was looking for a one night stay in Islamorada that wouldn't break the bank, but still be comfortable and clean. The Chesapeake Resort fit the bill! Rooms have been updated and resort was clean and quiet. It has a nice area for sunning and two pools. There isn't a restaurant or bar on site, but ..."

Reviewed on Apr 14, 2025

Chesapeake Beach Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
  • 10 min walk from Theater of the Sea
The price is $371 per night from May 12 to May 13
$371
includes taxes & fees
May 12 - May 13
Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (12 reviews)
"Our stay here was great for the most part! 2 hicupps; the room we were assigned, the shower door leaked all over the floor! However, when letting the fromt desk know, they upgradedus to a room right off the beach ground floor so we were very happy!"

Reviewed on Apr 12, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
  • 8 min drive from Theater of the Sea
The price is $370 per night from May 11 to May 12
$370
includes taxes & fees
May 11 - May 12
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9/10 Wonderful! (1,063 reviews)
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Reviewed on Apr 12, 2025

Cheeca Lodge & Spa
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
  • 12 min drive from Theater of the Sea
The price is $310 per night from May 4 to May 5
$310
includes taxes & fees
May 4 - May 5
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,194 reviews)
"Lobby was cool. Overall design"

Reviewed on Apr 12, 2025

Amara Cay Resort
La Siesta Resort & Villas
La Siesta Resort & Villas
4 out of 5
80241 Overseas Highway, Islamorada, FL
  • 11 min drive from Theater of the Sea
The price is $293 per night from May 4 to May 5
$293
includes taxes & fees
May 4 - May 5
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.6/10 Excellent! (1,004 reviews)
"Very nice place for family vacation"

Reviewed on Apr 10, 2025

La Siesta Resort & Villas
Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
  • 7 min drive from Theater of the Sea
The price is $332 per night from May 4 to May 5
$332
includes taxes & fees
May 4 - May 5
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,003 reviews)
"Beach, paths, plantings are exceptional! Loved all of the beautiful outdoor furniture."

Reviewed on Apr 12, 2025

Islander Resort
Fisher Inn Resort & Marina
Fisher Inn Resort & Marina
3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
  • 6 min walk from Theater of the Sea
The price is $256 per night from Apr 28 to Apr 29
$256
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,002 reviews)
"We stayed for two days. Sunrises were amazing. A lot of things were in walking distance. We took the bikes from the resort all over town."

Reviewed on Apr 10, 2025

Fisher Inn Resort & Marina
Hadley Resort and Marina
Hadley Resort and Marina
3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
  • 5 min drive from Theater of the Sea
The price is $247 per night from May 14 to May 15
$247
includes taxes & fees
May 14 - May 15
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
7.8/10 Good! (1,005 reviews)
"Very clean and the ocean front has a beautiful view."

Reviewed on Apr 8, 2025

Hadley Resort and Marina
Matecumbe Resort
Matecumbe Resort
2 out of 5
76261 Overseas Hwy, Islamorada, FL
  • 21 min drive from Theater of the Sea
The price is $213 per night from May 6 to May 7
$213
includes taxes & fees
May 6 - May 7
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key ...
9/10 Wonderful! (24 reviews)
On the road again
"This is a wonderful resort! We stopped here for 2 nights on our way further down the keys and what a gem! Our little apartment was so comfy with a full kitchen and a huge porch overlooking the garden, which is beautiful by the way. A large living room and dining area with a T.V. in the living room ..."

Reviewed on Apr 14, 2025

Matecumbe Resort
Treasure Harbor
Treasure Harbor
2 out of 5
200 Treasure Harbor Dr, Islamorada, FL
  • 5 min drive from Theater of the Sea
The price is $343 per night from Apr 27 to Apr 28
$343
includes taxes & fees
Apr 27 - Apr 28
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.2/10 Wonderful! (67 reviews)
"Staying in a houseboat was a new experience for us. It was comfortable and clean. Toni at the desk was wonderful and very attentive. The price for the Keys was better than average. We're glad we made the choice!"

Reviewed on Apr 6, 2025

Treasure Harbor
Breezy Palms Resort
Breezy Palms Resort
2.5 out of 5
80015 Overseas Highway, Islamorada, FL
  • 12 min drive from Theater of the Sea
The price is $183 per night from Apr 16 to Apr 17
$183
includes taxes & fees
Apr 16 - Apr 17
Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (446 reviews)
"Breezy palms resort was beautiful & so picturesque. We really enjoyed the sunrise & gorgeous views."

Reviewed on Apr 14, 2025

Breezy Palms Resort
The Islands of Islamorada
The Islands of Islamorada
4 out of 5
82779 Old Hwy, Islamorada, FL
  • 5 min drive from Theater of the Sea
The price is $729 per night from May 4 to May 5
$729
includes taxes & fees
May 4 - May 5
Stay at this 4-star beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ...
9.6/10 Exceptional! (55 reviews)
"Absolutely outstanding resort. Legitimate 5 star property."

Reviewed on Apr 13, 2025

The Islands of Islamorada
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find cheap hotels in Islamorada

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How many hotels are there in Islamorada?

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