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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 $312 total per night from Jun 8 to Jun 9
$312 total
per night
Jun 8 - Jun 9
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! (1,023 reviews)

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

Travelers say...
"I wasn't able to enjoy as much as I would have liked. Unfortunately, the waterfront seemed to be a magnet for seaweed. The food and portions wer great along with all the staff that I came in contact with"

Reviewed on Jun 1, 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 $297 total per night from Jun 3 to Jun 4
$297 total
per night
Jun 3 - Jun 4
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! (1,313 reviews)

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

Travelers say...
"great place to be"

Reviewed on Jun 1, 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 $270 total per night from Jun 8 to Jun 9
$270 total
per night
Jun 8 - Jun 9
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! (1,736 reviews)

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

Travelers say...
"This place is perfect"

Reviewed on Jun 1, 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 $347 total per night from Jun 15 to Jun 16
$347 total
per night
Jun 15 - Jun 16
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! (1,001 reviews)

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

Travelers say...
"Great place to relax and no crowds."

Reviewed on May 31, 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 $359 total per night from Jun 29 to Jun 30
$359 total
per night
Jun 29 - Jun 30
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! (202 reviews)

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

Travelers say...
"The property was beautiful as soon as we pulled up we were greeted by a woman on a golf cart. She was so happy and helpful. It made us feel comfortable right away, showed us to the front desk and she was also so very friendly. I wish I remembered their names. We got an ocean view. It also overlooked ..."

Reviewed on May 30, 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
The price is $309 total per night from Jun 8 to Jun 9
$309 total
per night
Jun 8 - Jun 9
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! (1,287 reviews)

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

Travelers say...
"Muy buen plan en familia para ir a los cayos. Buena atención y limpieza"

Reviewed on Jun 1, 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 $215 total per night from Jun 11 to Jun 12
$215 total
per night
Jun 11 - Jun 12
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! (1,004 reviews)

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

Travelers say...
"Muy mal trato del personal que te recibe en la propiedad"

Reviewed on May 31, 2026

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

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL
The price is $284 total per night from Jun 14 to Jun 15
$284 total
per night
Jun 14 - Jun 15
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! (1,004 reviews)

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

Travelers say...
"Fantastic property. Quiet and family friendly."

Reviewed on Jun 2, 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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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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