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Choose from 2118 Islamorada Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
  • 21 min drive from Anne's Beach
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 ...
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
  • 25 min drive from Anne's Beach
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. ...
9.4/10 Exceptional! (1,819 reviews)
"I loved having a balcony to sit on to view the water. It was perfect for morning coffee or an afternoon to read. The breakfast every morning was perfect, and provided healthy options like fruit and yogurt. I tried a bite of my husband’s omelette and it was excellent. All the staff was friendly and ..."

Reviewed on Nov 12, 2026

Chesapeake Beach 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
  • 27 min drive from Anne's Beach
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 ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
  • 16 min drive from Anne's Beach
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 ...
Amara Cay Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway Islamorada FL
  • 22 min drive from Anne's Beach
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. ...
9.4/10 Exceptional! (1,166 reviews)
"Great stay, will definitely recommend"

Reviewed on Nov 13, 2026

Islander Resort
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy Islamorada FL
  • 29 min drive from Anne's Beach
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! (1,002 reviews)
"A+"

Reviewed on Nov 12, 2026

Fisher Inn Resort & Marina
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
  • 16 min drive from Anne's Beach
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 ...
9/10 Wonderful! (785 reviews)
"Rooms werent cleaned daily however the facilities were clean. Beach and pool on-site were excellent"

Reviewed on Nov 9, 2026

Breezy Palms Resort
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
  • 33 min drive from Anne's Beach
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! (185 reviews)
"Great experience"

Reviewed on Nov 13, 2026

Treasure Harbor
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway Islamorada FL
  • 22 min drive from Anne's Beach
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. ...
La Jolla Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway Islamorada FL
  • 17 min drive from Anne's Beach
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! (1,003 reviews)
"Great first time experience and lovely property"

Reviewed on Nov 12, 2026

La Siesta Resort & Villas
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

3 out of 5
84801 Overseas Highway Islamorada FL
  • 28 min drive from Anne's Beach
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! (309 reviews)
"This is my second time staying here. It's a laid-back, extremely quiet place, so if you're looking for the party vibe, definitely not for you. The "beach" is really no more than a mangrove swamp, but that's typical of the Keys. For beaches, look elsewhere in Florida. The pool makes up for it, though. ..."

Reviewed on Nov 13, 2026

Coconut Cove Resort and Marina
Casa Morada

Casa Morada

3.5 out of 5
82200 overseas HWY Islamorada FL
  • 22 min drive from Anne's Beach
Book a stay at this beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Casa Morada
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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If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $159. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Islamorada hotel deals at the last minute.

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Frequently Asked Questions About Islamorada hotels

Where can I find the best last-minute travel deals?

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How many hotels are there in Islamorada?

With over 2,118 hotels in Islamorada, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $159.

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