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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! (1,007 reviews)

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

Travelers say...
"Perfect gateaway with my husband! THANKS EXPEDIA FOR A GREAT PRICE in a wonderful place! we enjoyed it every minute. WE will back soon!"

Reviewed on Jul 19, 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
$271 nightly
The price is $304 total per night from Aug 18 to Aug 19
$304 total
Aug 18 - Aug 19
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! (47 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
$320 nightly
The price is $361 total per night from Aug 20 to Aug 21
$361 total
Aug 20 - Aug 21
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! (1,134 reviews)

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

Travelers say...
"Amazing"

Reviewed on Jul 18, 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
$183 nightly
The price is $206 total per night from Aug 12 to Aug 13
$206 total
Aug 12 - Aug 13
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! (1,480 reviews)

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

Travelers say...
"Great view! Sweet ppl that work there!"

Reviewed on Jul 19, 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 21 to Jul 22
$279 total
Jul 21 - Jul 22
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! (1,000 reviews)

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

Travelers say...
"Completely renovated like new very well done. This is a little gem in Islamorada. I’ll be staying here every visit now. What a find!"

Reviewed on Jul 17, 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
$216 nightly
The price is $244 total per night from Aug 12 to Aug 13
$244 total
Aug 12 - Aug 13
Total includes taxes and fees
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a ...
8.8/10 Excellent! (1,237 reviews)

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

Travelers say...
"Cool atmosphere. Lobby/lounge area was cute and the bar looked nice. We're here in the off season so the hours for the tiki bar werent super ideal, but it was still nice."

Reviewed on Jul 16, 2025

Amara Cay Resort
Drop Anchor
Great for beach vacations

Drop Anchor

84959 Overseas Highway, 222, Islamorada, FL
$196 nightly
The price is $216 total per night from Jul 23 to Jul 24
$216 total
Jul 23 - Jul 24
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! (1,001 reviews)

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

Travelers say...
"This was our second stay in a month. Great location, beautiful property on the water. We love it here and cant wait to go back."

Reviewed on Jul 18, 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
$201 nightly
The price is $227 total per night from Aug 18 to Aug 19
$227 total
Aug 18 - Aug 19
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! (1,001 reviews)

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

Travelers say...
"Trudane from front desk is such a good employee. Took time to explain & has a concern for visitors comfort. Thanks trudane, you make our stay great!"

Reviewed on Jul 16, 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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