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Top Islamorada Beach Resorts & Hotels

Islander Resort
Great for beach vacations

Islander Resort

82100 Overseas Highway Islamorada FL
$316 nightly
The price is $356 total per night from Jun 22 to Jun 23
$356 total
Jun 22 - Jun 23
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 ...
9.4/10 Exceptional! (1,056 reviews)

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

Travelers say...
"We were only there one night."

Reviewed on Jun 15, 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
$276 nightly
The price is $310 total per night from Jul 16 to Jul 17
$310 total
Jul 16 - Jul 17
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! (1,333 reviews)

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

Travelers say...
"We had a wonderful stay and really loved the resort. The room and balcony were absolutely perfect. My one suggestion would be to consider making one of the two beachfront pools adults-only. There is already an adults-only pool on the property, which is a nice option, but it’s located in the middle ..."

Reviewed on Jun 15, 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
$239 nightly
The price is $269 total per night from Jun 18 to Jun 19
$269 total
Jun 18 - Jun 19
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! (1,759 reviews)

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

Travelers say...
"Staff was very helpful and friendly. 2 pools are great as is free kayaks and paddle boards. Breakfast cooked to order and delicious. 6&4 yr old grandkids had a ball. This is our 2nd time staying here."

Reviewed on Jun 15, 2026

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

Pines & Palms Resort

80401 Old Hwy Islamorada FL
$308 nightly
The price is $347 total per night from Jun 30 to Jul 1
$347 total
Jun 30 - Jul 1
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! (1,006 reviews)

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

Travelers say...
"Wonderful property and friendly staff. Rooms were lovely and beds very comfortable"

Reviewed on Jun 15, 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
$336 nightly
The price is $378 total per night from Jun 29 to Jun 30
$378 total
Jun 29 - Jun 30
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! (209 reviews)

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

Travelers say...
"Clean room and friendly staff. Refrigerator wasn’t cold, no weather stripping in door was drafty forcing the A/C to run non stop. Shower pools water as the floor doesn’t slope to the drain."

Reviewed on Jun 15, 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
$264 nightly
The price is $297 total per night from Jul 8 to Jul 9
$297 total
Jul 8 - Jul 9
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! (1,312 reviews)

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

Travelers say...
"We had a wonderful stay at Amara Cay and recommend it for an unforgettable vacation. We were treated with great kindness, and the place is beautiful."

Reviewed on Jun 15, 2026

Opens in a new windowAmara Cay Resort
La Siesta Resort & Villas
Great for beach vacations

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $271 total per night from Jul 6 to Jul 7
$271 total
Jul 6 - Jul 7
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, ...
8.8/10 Excellent! (1,026 reviews)

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

Travelers say...
"location convenience"

Reviewed on Jun 15, 2026

Opens in a new windowLa Siesta Resort & Villas
Drop Anchor
Great for beach vacations

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
$174 nightly
The price is $192 total per night from Jun 30 to Jul 1
$192 total
Jun 30 - Jul 1
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 ...
Opens in a new windowDrop Anchor
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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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