Explore beach hotels in Islamorada, FL from $181

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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
$380 nightly
The price is $428 total per night from Jan 29 to Jan 30
$428 total
Jan 29 - Jan 30
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! (1,008 reviews)

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

Travelers say...
Really liked this place! Had a few issues with hot water and the shower. They were definitely responsive about fixing but there were some language barriers which made that a little difficult. Some of the furniture around the pool needed some love. And there was a lot of empty space on the property ...

Reviewed on Jan 13, 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
$346 nightly
The price is $390 total per night from Jan 21 to Jan 22
$390 total
Jan 21 - Jan 22
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! (1,290 reviews)

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

Travelers say...
Overall our stay was fabulous. Some small gripes are the shower heads were built up with mineral deposits and didn’t spray properly and there was a leak in our ceiling above the toilet. However it is a beautiful resort. Lots of amenities, fun for the whole family

Reviewed on Jan 11, 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
$223 nightly
The price is $251 total per night from Jan 25 to Jan 26
$251 total
Jan 25 - Jan 26
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! (1,626 reviews)

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

Travelers say...
Very clean and nice. Not a 5 star resort. But nice. Breakfast was good

Reviewed on Jan 11, 2026

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

Pines & Palms Resort

80401 Old Hwy Islamorada FL
$328 nightly
The price is $369 total per night from Jan 25 to Jan 26
$369 total
Jan 25 - Jan 26
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 ...
9/10 Wonderful! (1,008 reviews)

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

Travelers say...
Lovely people, peaceful resort, beautiful accommodations, great walkability.

Reviewed on Jan 11, 2026

Opens in a new windowPines & Palms Resort
Amara Cay Resort
Great for beach vacations

Amara Cay Resort

80001 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$273 nightly
The price is $308 total per night from Jan 27 to Jan 28
$308 total
Jan 27 - Jan 28
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! (1,263 reviews)

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

Travelers say...
Amazing place to stay. Staff was great

Reviewed on Jan 16, 2026

Opens in a new windowAmara Cay 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
$347 nightly
The price is $391 total per night from Jan 22 to Jan 23
$391 total
Jan 22 - Jan 23
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 ...
8.8/10 Excellent! (125 reviews)

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

Travelers say...
We had a wonderfull time. Everyone was very attentive and helpful.

Reviewed on Jan 11, 2026

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

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
$192 nightly
The price is $212 total per night from Jan 19 to Jan 20
$212 total
Jan 19 - Jan 20
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! (1,000 reviews)

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

Travelers say...
Great

Reviewed on Jan 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
$361 nightly
The price is $407 total per night from Feb 5 to Feb 6
$407 total
Feb 5 - Feb 6
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! (1,005 reviews)

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

Travelers say...
The kitchen had nothing in it, so plan ahead. No silverware at all. The room was as pictured, and the pool.and beach areas were very nice. Lots of restaurants super close. Shopping nearby as well

Reviewed on Jan 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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Pet-friendly Beach Hotels in Islamorada

Islamorada Beach Hotels with Restaurants

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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