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Hotels in Islamorada

Choose from 2200 Islamorada Hotel Deals

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! (1,735 reviews)
Amazing breakfast! Location very good. Attentive staff, plenty of wild life such as iguanas, sharks (we spotted a baby shark and a bigger one!), fish, birds etc. The nice thing is that you can use 2 hours per day a sub, kajak, fishing rod, bicycle and more for free!

Reviewed on May 11, 2026

Chesapeake Beach Resort
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! (1,330 reviews)
Exelente service but the room need more clean and attention

Reviewed on May 11, 2026

Cheeca Lodge & Spa
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! (1,013 reviews)
Everything about this property was excellent, from the wonderful staff to the kid-friendly atmosphere. We loved the breakfast brunch and the overall vibe of the place. However, dinner at The Drift was a letdown. For the price, the quality just wasn't there. I’d highly recommend the stay, but I suggest ...

Reviewed on May 10, 2026

Islander 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! (1,280 reviews)
Unfortunately I had a bad experience regarding a fish I ate at the restaurant on property. It was spoiled and I ended up having to go to a nearby hospital due to the terrible spoiling effects of the food.

Reviewed on May 11, 2026

Amara Cay 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! (194 reviews)
The resort, staff and facilities are excellent. The location in Islamorada is great either for a few days in the keys or as a stopping point to or from Key West. We didn’t get time to use all of the facilities but there are restaurants on site, kayaks, pools, a lively beach and breakfast so you don’t ...

Reviewed on May 10, 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 ...
8.6/10 Excellent! (1,009 reviews)
This place is a sanctuary I love this hotel and with my mom and my child the best Mother’s Day ever 😍👍

Reviewed on May 11, 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 ...
8.2/10 Very Good! (1,007 reviews)
This is a pretty property that is near the water and several restaurants. Our room was overlooking the boat ramp, which we weren't expecting and someone was cleaning their boat right below us for several hours. For some reason they have speakers all around the property that were planning music until ...

Reviewed on May 6, 2026

Fisher Inn Resort & 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! (259 reviews)
The room was clean and spacious however it had a very strong smell (intentional deodorizer) that was a little overwhelming. The ac was set to 65, mini split “said” 70 and it was absolutely freezing!!! I couldn’t figure out how to turn it up at 1am! Also that same ac unit made a noise every 10 minutes ...

Reviewed on May 10, 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! (153 reviews)
This place is absolutely incredible. It offers a perfect harmony with nature—you immediately feel relaxed and at peace as soon as you arrive. The atmosphere is calm, quiet, and truly refreshing, making it the perfect escape from everyday stress. The fishing experience here is amazing. Whether you're ...

Reviewed on May 3, 2026

Treasure Harbor
Bayside Villas by Islander Resort

Bayside Villas by Islander Resort

3.5 out of 5
81450 Overseas Highway Islamorada FL
  • 9 min drive from Theater of the Sea
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 3 restaurants. Popular attractions Hurricane Monument and MoradaWay Arts & ...
8.8/10 Excellent! (427 reviews)
La propiedad me encantó, muy limpia y bonita. Para el precio está muy bien, sin duda volvería

Reviewed on May 10, 2026

Bayside Villas by Islander Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
  • 6 min drive from Theater of the Sea
Stay at this hotel in Islamorada. Enjoy free WiFi, a private beach, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. ...
9/10 Wonderful! (1,008 reviews)
For the price it could be better. Rooms close to road are load. Bathroom needs updating

Reviewed on May 10, 2026

La Jolla Resort
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! (1,003 reviews)
Excellent

Reviewed on May 10, 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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