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Hotels in Islamorada

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Choose from 2214 Islamorada Hotel Deals

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
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! (1,089 reviews)
"Trip was amazing. Service was top tier food was amazing and a Beautiful Ocean view. Highly recommend and I'll definitely be back."

Reviewed on May 29, 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
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
8.8/10 Excellent! (1,194 reviews)
"Beautiful clean and well maintained outdoor and indoor areas. The outdoor dining, tiki hut bar, and beach areas have a tropical Hawaii type feeling to it. Would love to stay there again."

Reviewed on May 29, 2025

Amara Cay 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
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 ...
9.2/10 Wonderful! (27 reviews)
"friendly convenient"

Reviewed on May 26, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Chesapeake Beach Resort
Chesapeake Beach Resort
3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
  • 22 min walk from Theater of the Sea
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! (1,450 reviews)
"We love coming the resort. We stay at least twice each summer and the staff is so friendly and helpful."

Reviewed on May 28, 2025

Chesapeake Beach 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
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! (1,003 reviews)
"We loved our stay here but unfortunately didn't get to enjoy sitting in the balcony much due to guests next door smoking but other than that we loved it !"

Reviewed on May 30, 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
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! (1,001 reviews)
"We had such a memorable stay at the Islander Resort. We truly loved every second of it! The staff was warm, attentive, and always helpful without being overbearing. The rooms are spacious, beautifully kept, and having a private patio was the cherry on top. Everything from the beach to the pool, movie ..."

Reviewed on May 29, 2025

Islander Resort
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
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! (1,001 reviews)
"A very special place in the heart of the keys,convenient for sho and dinner, water sports rental for a jet ski or a boat."

Reviewed on May 28, 2025

Hadley Resort and Marina
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
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! (998 reviews)
"Very simple but clean and nice little hotel. It’s been recently renovated."

Reviewed on May 19, 2025

Fisher Inn Resort & Marina
Coconut Cove Resort and Marina
Coconut Cove Resort and Marina
2.5 out of 5
84801 Overseas Highway, Islamorada, FL
  • 2 min walk from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
7.6/10 Good! (782 reviews)
"I love"

Reviewed on May 29, 2025

Coconut Cove Resort and Marina
Breezy Palms Resort
Breezy Palms Resort
2.5 out of 5
80015 Overseas Highway, Islamorada, FL
  • 12 min drive from Theater of the Sea
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! (482 reviews)
"Our stay was pleasant. The staff is friendly. The property is an older property but fairly well maintained. Our unit was updated and clean. The only complaint I have is the hot water in the shower wouldn't hold steady."

Reviewed on May 28, 2025

Breezy Palms Resort
Matecumbe Resort
Matecumbe Resort
2 out of 5
76261 Overseas Hwy, Islamorada, FL
  • 21 min drive from Theater of the Sea
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 ...
8.8/10 Excellent! (51 reviews)
"We had a beautiful view and enough space in the apartment for our group of 5. It was nice that they had kayaks and bikes available but it was hard to actually use them trying to coordinate when staff was there and allowing to have them 2 hours. I just didn’t feel like the front office was there to ..."

Reviewed on May 30, 2025

Matecumbe 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
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! (61 reviews)
"Great property. Very comfortable and luxurious. The bar and food options can delivered to the room and very tasty! Really enjoyed the stay. Charlene was a great bartender by the pool!"

Reviewed on May 4, 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.

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