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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
$434 nightly
The price is $488 total per night from Mar 2 to Mar 3
$488 total
Mar 2 - Mar 3
Total with taxes and fees
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! (1,000 reviews)

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

Travelers say...
Nice size room, beautiful grounds

Reviewed on Feb 10, 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
$421 nightly
The price is $474 total per night from Feb 22 to Feb 23
$474 total
Feb 22 - Feb 23
Total with taxes and fees
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! (1,300 reviews)

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

Travelers say...
View and ambience

Reviewed on Feb 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
$463 nightly
The price is $521 total per night from Mar 1 to Mar 2
$521 total
Mar 1 - Mar 2
Total with taxes and fees
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! (1,675 reviews)

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

Travelers say...
Nice stay

Reviewed on Feb 10, 2026

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

Pines & Palms Resort

80401 Old Hwy Islamorada FL
$538 nightly
The price is $605 total per night from Feb 23 to Feb 24
$605 total
Feb 23 - Feb 24
Total with taxes and fees
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...
Beautiful rooms and facility! So clean! Friendly staff!!

Reviewed on Jan 30, 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
$509 nightly
The price is $572 total per night from Mar 8 to Mar 9
$572 total
Mar 8 - Mar 9
Total with taxes and fees
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! (146 reviews)

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

Travelers say...
The property is stunning and expansive with a friendly staff. Dinner at Kindler was delicious. We removed one star because of a series of details that added up. Our first room smelled like must/mold. The second room had a visibly damaged dresser, a broken screen lock and no hot water in the sink ...

Reviewed on Feb 10, 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
$423 nightly
The price is $476 total per night from Feb 25 to Feb 26
$476 total
Feb 25 - Feb 26
Total with taxes and fees
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! (1,254 reviews)

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

Travelers say...
Room was clean. Daily care was timely and immaculate. Staff was incredible. The atmosphere was delightful. We had such an amazing time.

Reviewed on Feb 15, 2026

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

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
$244 nightly
The price is $270 total per night from Feb 22 to Feb 23
$270 total
Feb 22 - Feb 23
Total with taxes and fees
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 ...
8.6/10 Excellent! (1,003 reviews)

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

Travelers say...
Loved this place

Reviewed on Feb 2, 2026

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

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL
$432 nightly
The price is $487 total per night from Mar 1 to Mar 2
$487 total
Mar 1 - Mar 2
Total with taxes and fees
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, ...
8.6/10 Excellent! (1,003 reviews)

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

Travelers say...
Yes

Reviewed on Feb 12, 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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