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Top Islamorada Beach Resorts & Hotels

Islander Resort
Great for beach vacations

Islander Resort

82100 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $504 total per night from Apr 12 to Apr 13
$504 total
per night
Apr 12 - Apr 13
A private beach, 3 restaurants, and 2 outdoor pools are all featured at this hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families ...
9.2/10 Wonderful! (1,008 reviews)

Travelers like: on the beach, cabanas, beach bars, beach umbrellas

Travelers say...
Beautiful place to stay!

Reviewed on Mar 16, 2026

Opens in a new windowIslander Resort
Cheeca Lodge & Spa
Great for beach vacations

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $645 total per night from Apr 12 to Apr 13
$645 total
per night
Apr 12 - Apr 13
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
9.2/10 Wonderful! (1,299 reviews)

Travelers like: on the beach, sun loungers, beach yoga, massages on beach

Travelers say...
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

Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort
Great for beach vacations

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $304 total per night from Apr 15 to Apr 16
$304 total
per night
Apr 15 - Apr 16
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
9.2/10 Wonderful! (1,671 reviews)

Travelers like: on the beach, sun loungers, beach towels, outdoor pools

Travelers say...
The room we stayed in needs shelf space in the bathroom. It had nowhere to put toiletries. The room was clean and good a/c.

Reviewed on Mar 16, 2026

Opens in a new windowChesapeake Beach Resort
Pines & Palms Resort
Great for beach vacations

Pines & Palms Resort

80401 Old Hwy Islamorada FL
The price is $504 total per night from Mar 23 to Mar 24
$504 total
per night
Mar 23 - Mar 24
The private beach and marina are among the highlights at this hotel. Enjoy a day at the beach snorkeling, or relax with sun loungers. Enjoy the outdoor pool ...
9.2/10 Wonderful! (1,000 reviews)

Travelers like: on the beach, sun loungers, beach bars, beach yoga

Travelers say...
The room was beautiful, the or

Reviewed on Mar 1, 2026

Opens in a new windowPines & Palms Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Great for beach vacations

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

84001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $391 total per night from Apr 15 to Apr 16
$391 total
per night
Apr 15 - Apr 16
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
9/10 Wonderful! (170 reviews)

Travelers like: on the beach, sun loungers, beach bars, beach towels

Travelers say...
Loved our stay! Beautiful property, comfortable beds. Should've stayed longer honestly. Only thing we'll do different next time is ask for a room in the 21+ area.

Reviewed on Mar 14, 2026

Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Amara Cay Resort
Great for beach vacations

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $339 total per night from Mar 26 to Mar 27
$339 total
per night
Mar 26 - Mar 27
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. If you want to take your pet along, this pet-friendly property offers everything ...
8.8/10 Excellent! (1,257 reviews)

Travelers like: on the beach, beach towels, outdoor pool

Travelers say...
Pool and beach area were extremely nice. The room was nice and clean, but you can tell it was an older hotel that they are working on remodeling. In some areas you could tell there was some deferred maintenance.

Reviewed on Mar 15, 2026

Opens in a new windowAmara Cay Resort
Drop Anchor
Great for beach vacations

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
The price is $409 total per night from Mar 23 to Mar 24
$409 total
per night
Mar 23 - Mar 24
An outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A business center, a garden, and a picnic area ...
8.8/10 Excellent! (1,007 reviews)

Travelers like: close to beach, sun loungers, beach umbrellas, beach towels

Travelers say...
Very pleasantly surprised with the location and quality of this resort. The water view is available throughout the property and this resort is well taken care of. The pool was exceptionally clean and refreshing.

Reviewed on Mar 14, 2026

Opens in a new windowDrop Anchor
La Siesta Resort & Villas
Great for beach vacations

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
The price is $329 total per night from Mar 22 to Mar 23
$329 total
per night
Mar 22 - Mar 23
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...
8.8/10 Excellent! (1,001 reviews)

Travelers like: on the beach, beach towels, outdoor pool

Travelers say...
We had a partial view of the ocean and pool. The location was great The pull out sofa tho was like sleeping on a chain link fence.

Reviewed on Mar 14, 2026

Opens in a new windowLa Siesta Resort & Villas
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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.

Top Beach Hotels where Kids Stay FREE

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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What are the cheapest hotels on the beach in Islamorada

  • Cheeca Lodge & Spa - Book Now
    • Located on Upper Matecumbe Key, Islamorada, Cheeca Lodge & Spa is less than a mile from the Hurricane Monument. It's a 2-minute drive to the History of Diving Museum, and 5 minutes to Theater of the Sea. Morada Way Arts & Cultural District is a 5-minute walk from the hotel.
    • 4.00 star rating.
  • Eager to Please in the Keys - 4 Br home by RedAwning - Book Now
    • 3.00 star rating.
  • Ed & Ellens Lodging Key largo - Book Now
    • Situated in Key Largo, this condo is within 2 mi (3 km) of MarineLab Undersea Laboratory, Dolphins Plus Bayside, and John Pennekamp Coral Reef State Park. Christ of the Deep and Dolphins Plus are also within 6 mi (10 km).
    • 3.00 star rating.

What’s better than a beautiful Islamorada hotel near the beach? Finding that hotel for a deal! Check out our amazing deals on stunning Islamorada beach hotel properties to find exactly what you’re looking for on your next trip to Islamorada.

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