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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
$268 nightly
The price is $302 total per night from Aug 11 to Aug 12
$302 total
Aug 11 - Aug 12
Total includes 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 ...
9/10 Wonderful! (1,014 reviews)

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

Travelers say...
"Loved everything"

Reviewed on Jul 22, 2025

Islander 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
$210 nightly
The price is $237 total per night from Aug 19 to Aug 20
$237 total
Aug 19 - Aug 20
Total includes 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! (48 reviews)

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

Great, but eat off property
"Property and service were great. Food was not great. Very difficult to find options for a picky eater. Had to DoorDash Wendy’s several times."

Reviewed on Jul 2, 2025

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Cheeca Lodge & Spa
Great for beach vacations

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
$288 nightly
The price is $325 total per night from Aug 24 to Aug 25
$325 total
Aug 24 - Aug 25
Total includes 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. ...
9/10 Wonderful! (1,137 reviews)

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

Travelers say...
"Stayed here for one night. Unfortunately the weather wasn’t great so we didn’t get to experience the pool areas and such. We walked around the grounds at night in the rain and it was still breath taking. Would love to stay longer the next time I am back in the area."

Reviewed on Jul 20, 2025

Cheeca Lodge & Spa
Chesapeake Beach Resort
Great for beach vacations

Chesapeake Beach Resort

83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $253 total per night from Aug 11 to Aug 12
$253 total
Aug 11 - Aug 12
Total includes 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 ...
9/10 Wonderful! (1,486 reviews)

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

Travelers say...
"One of my favorite places to have a relaxing trip with the family"

Reviewed on Jul 21, 2025

Chesapeake Beach Resort
Pines & Palms Resort
Great for beach vacations

Pines & Palms Resort

80401 Old Hwy, Islamorada, FL
$248 nightly
The price is $279 total per night from Jul 29 to Jul 30
$279 total
Jul 29 - Jul 30
Total includes 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! (1,001 reviews)

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

Travelers say...
"Everything at Pine and Palms was perfect! Great location!!! Ate at Square Grouper for dinner. Ride our bikes there."

Reviewed on Jul 21, 2025

Pines & Palms Resort
Amara Cay Resort
Great for beach vacations

Amara Cay Resort

80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
$224 nightly
The price is $253 total per night from Aug 13 to Aug 14
$253 total
Aug 13 - Aug 14
Total includes 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! (1,241 reviews)

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

Travelers say...
"Espectacular"

Reviewed on Jul 21, 2025

Amara Cay Resort
Drop Anchor
Great for beach vacations

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL
$174 nightly
The price is $192 total per night from Jul 27 to Jul 28
$192 total
Jul 27 - Jul 28
Total includes 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! (1,002 reviews)

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

Travelers say...
"It was that keys feeling that everyone looks for"

Reviewed on Jul 21, 2025

Drop 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
$195 nightly
The price is $220 total per night from Jul 27 to Jul 28
$220 total
Jul 27 - Jul 28
Total includes 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...
"Marilyn in the lobby was amazing! She was so attentive and helpful. All the staff was super friendly and accommodating! I would definitely stay here again."

Reviewed on Jul 20, 2025

La 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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