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Choose from 2208 Islamorada Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 8 min drive from Theater of the Sea
Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,298 reviews)
We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window

Reviewed on Mar 12, 2026

Cheeca Lodge & Spa
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 free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (1,666 reviews)
We upgraded to an Ocean View and it was fantastic! Nice quiet vacation and great location with walkable restaurants and bars. Breakfast was special with awesome omlets by Chris!!

Reviewed on Mar 13, 2026

Chesapeake Beach Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
  • 12 min drive from Theater of the Sea
Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ...
8.8/10 Excellent! (1,251 reviews)
We had a partial view of ocean from our room. We did not use the pool but it was a decent looking. The staff was kind and professional. The room we had smelled of mold strongly.

Reviewed on Mar 12, 2026

Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
  • 7 min drive from Theater of the Sea
Book a stay at this 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. ...
9.2/10 Wonderful! (1,004 reviews)
We had a beautiful time during our stay. The rooms are so comfortable and have beautiful views. The staff was kind and even checked on us to see if we needed more coffee. The views were perfect day and night. We enjoyed the pool and played some golf and relaxed. Best week ever!

Reviewed on Mar 14, 2026

Islander Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
84001 Overseas Hwy Islamorada FL
  • 10 min walk from Theater of the Sea
Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (169 reviews)
Overpriced for a view of the parking lot on the ground floor.

Reviewed on Mar 7, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio 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
Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
8.8/10 Excellent! (1,000 reviews)
Great place

Reviewed on Mar 6, 2026

La Siesta Resort & Villas
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
  • 5 min walk from Theater of the Sea
Book a stay at this beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
8.4/10 Very Good! (1,002 reviews)
The room is smaller than in the photos and rooms are more run down. WiFi never worked during our stay and we did not receive the complimentary cocktail and snack upon arrival as promised. Staff wasn't great but they did fix the broken shower head the day before we left. It was fine but not as great ...

Reviewed on Mar 11, 2026

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
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 ...
7.6/10 Good! (1,003 reviews)
We were suppose to have pool villa. No view of the pool from our room. Did get $100 off our stay. Pool was dirty. Continental breakfast was good. Need railings in room for stairs. Need table lamp in living room. Shared balcony. Was woken up by loud music on balcony at 11 pm one night.

Reviewed on Mar 13, 2026

Hadley Resort and Marina
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 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. ...
9/10 Wonderful! (216 reviews)
This property is not at all as it appears on Expedia. While the Front Office Manager was lovely, the property is very dated and tired looking. When we walked into our room we were overwhelmed by the smell of mildew such that we could not stay. We left the key on the counter and searched for another ...

Reviewed on Mar 12, 2026

Coconut Cove Resort and Marina
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
  • 5 min drive from Theater of the Sea
Stay at this houseboat in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (143 reviews)
Great A/C and the house boats are really nice. close to things to do

Reviewed on Mar 12, 2026

Treasure Harbor
Sunset Inn

Sunset Inn

3 out of 5
82200 Overseas Hwy Islamorada FL
  • 6 min drive from Theater of the Sea
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the pool and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,001 reviews)
Yes pool was great! Very clean nice rooms, close to walk to a lot of fun things! Loved the bikes you can use

Reviewed on Mar 11, 2026

Sunset Inn
Drop Anchor

Drop Anchor

3 out of 5
84959 Overseas Highway, 222 Islamorada FL
  • 8 min walk from Theater of the Sea
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,006 reviews)
Not our room.

Reviewed on Mar 13, 2026

Drop Anchor
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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