Search for Cheap Deals on
Hotels in Islamorada

Choose from 2214 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 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)
"Good"

Reviewed on May 26, 2025

Chesapeake Beach 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
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! (1,084 reviews)
"love it"

Reviewed on May 27, 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! (1,192 reviews)
"Perfect location and amenities! Loved our stay"

Reviewed on May 22, 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 ...
9/10 Wonderful! (24 reviews)
Great weekend getaway
"Love the new renovations, staff is friendly and hopeful, great place for families or just to get away."

Reviewed on May 19, 2025

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
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)
We will be back
"With the exception of the loud pool area music, it was a peaceful place to be. The staff was awesome and it was generally clean and well kept - except for the floors in our room which needed serious mopping. That being said, the music volume was lowered when we asked and the floors can be cleaned ..."

Reviewed on May 26, 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! (1,000 reviews)
Great place...food questionable?
"Loved this location. We've stayed at several resorts in the Keys and this was one of the best yet! Renovated rooms with an awesome waterfront beach. Loved everything about it....except...my dining experience fell short. My club sandwich was made on regular "small" slices of bread and at the most ..."

Reviewed on May 21, 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! (1,003 reviews)
"For a quick one day or two day vacy, your good."

Reviewed on May 26, 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! (781 reviews)
"Very friendly staff.beutiful pool.will come back again"

Reviewed on May 18, 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! (480 reviews)
"The room we stayed in was beautiful and newly renovated."

Reviewed on May 25, 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! (49 reviews)
"The resort was nice and well maintained. It could use a little updating but we werent there that much so it fit our needs perfectly. The negatives was a never ending fire alarm chirping in our room even after a battery change and a too soft mattress."

Reviewed on May 27, 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.

Find cheap hotels in Islamorada

You’re not an average traveler—and Hotwire knows it. Your wanderlust takes you off the beaten path to discover unique adventures and every travel destination’s lesser-known tourist scenes. Hotwire has the hookup! Book your Islamorada hotel with Hotwire to complete your one-of-a-kind travel checklist.

For you, intrepid voyager, Hotwire has a large selection of the best hotels in Islamorada.

Choosing the right hotel in Florida has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Islamorada’s 2,214 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $145. 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.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Islamorada. No matter your reason for visiting Islamorada, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Islamorada hotels

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

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Islamorada for as low as $145.

How many hotels are there in Islamorada?

With over 2,214 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 $145.

How to find cheap car rentals in Islamorada?

Finding a cheap car rental deal in Islamorada is as easy as scoring cheap hotels in Islamorada. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.