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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
$303 nightly
The price is $340 total per night from Nov 15 to Nov 16
$340 total
Nov 15 - Nov 16
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! (1,153 reviews)

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

Travelers say...
"Quiet and beautiful"

Reviewed on Oct 28, 2026

Opens in a new windowIslander Resort
Chesapeake Beach Resort
Great for beach vacations

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
$188 nightly
The price is $212 total per night from Nov 4 to Nov 5
$212 total
Nov 4 - Nov 5
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 ...
9.4/10 Exceptional! (1,800 reviews)

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

Travelers say...
"We loved the pools and hot tub. Tiki bar was a huge plus."

Reviewed on Oct 29, 2026

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

Pines & Palms Resort

80401 Old Hwy Islamorada FL
$272 nightly
The price is $306 total per night from Nov 19 to Nov 20
$306 total
Nov 19 - Nov 20
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! (1,003 reviews)

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

Travelers say...
"We stayed at one of the bungalows which were very new, cozy and comfortable. It had 3 bedrooms which was perfect for us!"

Reviewed on Oct 23, 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
$272 nightly
The price is $306 total per night from Nov 29 to Nov 30
$306 total
Nov 29 - Nov 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! (304 reviews)

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

Travelers say...
"The view from our room was outstanding. However, there was a horrible smell that kept floating on the wind from another part of the property- it smelled like sewage. The cleaning staff weren't great, and the woman who checked us in didn't give us any info on how to find our room. The rest of the ..."

Reviewed on Oct 29, 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
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $245 total per night from Nov 29 to Nov 30
$245 total
Nov 29 - Nov 30
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 ...
Opens in a new windowAmara Cay 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
$207 nightly
The price is $233 total per night from Nov 1 to Nov 2
$233 total
Nov 1 - Nov 2
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. ...
Opens in a new windowCheeca Lodge & Spa
Drop Anchor
Great for beach vacations

Drop Anchor

84959 Overseas Highway, 222 Islamorada FL
$215 nightly
The price is $237 total per night from Nov 1 to Nov 2
$237 total
Nov 1 - Nov 2
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
La Siesta Resort & Villas
Great for beach vacations

La Siesta Resort & Villas

80241 Overseas Highway Islamorada FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $265 total per night from Nov 29 to Nov 30
$265 total
Nov 29 - Nov 30
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, ...
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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