Explore beach hotels in Islamorada, FL from $142

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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
$324 nightly
The price is $365 total per night from Dec 18 to Dec 19
$365 total
Dec 18 - Dec 19
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! (1,021 reviews)

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

Travelers say...
The room was perfect and the outdoor space was great for morning coffees and reading!

Reviewed on Nov 29, 2025

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
$224 nightly
The price is $253 total per night from Dec 17 to Dec 18
$253 total
Dec 17 - Dec 18
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! (1,591 reviews)

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

Travelers say...
Great place

Reviewed on Nov 28, 2025

Opens in a new windowChesapeake Beach 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
$317 nightly
The price is $357 total per night from Dec 17 to Dec 18
$357 total
Dec 17 - Dec 18
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. ...
9/10 Wonderful! (1,278 reviews)

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

Travelers say...
Property is beautiful with tons of amenities. The room was very nice and overall we were very happy. Here are a few of the issues we had though for full transparency. The beach is sand, but it's hard in a way that's a bit unnatural and doesn't flow into the water. There were weddings on two nights ...

Reviewed on Dec 3, 2025

Opens in a new windowCheeca Lodge & Spa
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 Dec 8 to Dec 9
$279 total
Dec 8 - Dec 9
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! (1,005 reviews)

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

Travelers say...
Bed and bedding were clean and super comfortable. Kitchen had everything we needed to make our dinner on the grill (which was delivered 😊). View was specular! Right on the beach. Front desk staff was welcoming and helpful.

Reviewed on Nov 29, 2025

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
$250 nightly
The price is $282 total per night from Dec 11 to Dec 12
$282 total
Dec 11 - Dec 12
Total with taxes and fees
A private beach and a restaurant are featured at this resort. If you want to take your pet along, this pet-friendly property offers everything you'll need for ...
8.8/10 Excellent! (1,269 reviews)

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

Travelers say...
Loved the resort

Reviewed on Nov 21, 2025

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
$254 nightly
The price is $285 total per night from Dec 17 to Dec 18
$285 total
Dec 17 - Dec 18
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! (112 reviews)

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

Travelers say...
Beautiful room, stunning views

Reviewed on Nov 19, 2025

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
$130 nightly
The price is $142 total per night from Dec 7 to Dec 8
$142 total
Dec 7 - Dec 8
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...
The staff was very nice. Thanks

Reviewed on Nov 24, 2025

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
$218 nightly
The price is $246 total per night from Dec 15 to Dec 16
$246 total
Dec 15 - Dec 16
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! (1,000 reviews)

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

Travelers say...
Great stay and beautiful space

Reviewed on Dec 1, 2025

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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