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May 29 - May 31

Top Rated Islamorada Hotels

Cheeca Lodge & Spa
Cheeca Lodge & Spa
4.0 out of 5.0 81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
$349
4.4/5 (109 reviews)

Beautiful grounds in the best location the staff are the best in the Keys

Reviewed on Mar 27, 2020
Cheeca Lodge & Spa features a private beach, a golf course, and a full-service spa. Free valet and self parking are available, and there's also limo/town car ...
Amara Cay Resort
Amara Cay Resort
3.5 out of 5.0 80001 Overseas Hwy, Islamorada, FL
Free Cancellation
$177
4.3/5 (52 reviews)

From the moment we walked into the lobby we were greeting by the warm & welcoming staff. The lobby is absolutely gorgeous. The rooms are clean and very comfortable. You have a refrigerator and microwave. The pool and beach area are extremely well maintained and beautiful. The restaurant The Reel ...

Reviewed on Mar 18, 2020
At Amara Cay Resort, guests enjoy a private beach, an outdoor pool, and a fitness center. You can take advantage of free parking, along with a free area shuttle. ...
Pelican Cove Resort & Marina
Pelican Cove Resort & Marina
3.0 out of 5.0 84457 Overseas Highway, Islamorada, FL
Free Cancellation
$150
4.0/5 (87 reviews)

This is a very nice property however definitely not worth the$444/night I paid. It was spring break so the prices were inflated. The restaurant on property is closed so you had to go out to eat. The room was lovely clean and had a partial ocean view. The resort fee covered a lot and having access ...

Reviewed on Mar 20, 2020
Guests of Pelican Cove Resort & Marina have access to a private beach, a marina, and an outdoor pool. If you drive, put free parking to good use. The 24-hour ...
Postcard Inn Beach Resort & Marina
Postcard Inn Beach Resort & Marina
3.0 out of 5.0 84001 Overseas Hwy, Islamorada, FL
Free Cancellation
$174
3.9/5 (146 reviews)

A slice of tropical heaven. Many amenities included.

Reviewed on Mar 10, 2020
Postcard Inn Beach Resort & Marina features a private beach, a marina, and 2 outdoor pools. Transportation is made easy with a free area shuttle. The 24-hour ...
La Siesta Resort & Marina
La Siesta Resort & Marina
3.0 out of 5.0 80241 Overseas Highway, Islamorada, FL
Free Cancellation
$175
3.8/5 (39 reviews)

Location was nice. Ability to visit other hotels is plus.

Reviewed on Jan 2, 2020
Guests of La Siesta Resort & Marina have access to a private beach, a marina, and an outdoor pool. You can put free parking to good use if you drive. The 24-hour ...
Sunset Inn
Sunset Inn
3.0 out of 5.0 82200 Overseas Hwy, Islamorada, FL
Free Cancellation
$128
4.6/5 (14 reviews)

The location was excellent. It was very clean. No bedbugs. The staff was aweseome.

Reviewed on Mar 20, 2020
Guests of Sunset Inn enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. A stay here includes free parking. Front-desk ...
Drop Anchor
Drop Anchor
3.0 out of 5.0 84959 Overseas Highway, 222, Islamorada, FL
$191
4.5/5 (33 reviews)

We thoroughly enjoyed our 5 night stay at Drop Anchor.

Reviewed on Jan 11, 2020
Guests of Drop Anchor enjoy an outdoor pool, free WiFi in public areas, and coffee in a common area. If you drive, put free parking to good use. Friendly staff ...
The Caribbean Resort
The Caribbean Resort
3.5 out of 5.0 117 Carroll St, Islamorada, FL
Get Rates
5.0/5 (1 reviews)

Amazing resort, staff was incredibly friendly, pool & grounds were impeccable & our home was beautiful. We enjoyed our stay & will definitely be back!

Reviewed on Nov 30, 2018
Guests staying at The Caribbean Resort enjoy access to a marina, an outdoor pool, and a spa tub. The front desk is staffed 24 hours a day to help with tours/tickets ...
Hadley House Islamorada
Hadley House Islamorada
3.5 out of 5.0 82749 Overseas Hwy, Islamorada, FL
Free Cancellation
$138
4.1/5 (18 reviews)

Fantastic room and view. Julia at the desk was fantastic, so consistently cheerful.

Reviewed on Feb 28, 2020
Guests of Hadley House Islamorada have access to a private beach, a marina, and an outdoor pool. If you drive, put free parking to good use. The 24-hour front ...

Luxury Hotels in Islamorada

See all 613 Properties in Islamorada

Pet Friendly Islamorada Hotels

See all 613 Properties in Islamorada

Where should you stay in Islamorada?


What are some of the best cheap hotels in Islamorada?

Check out the 11 budget-friendly hotels in Islamorada to find a good rate. Fisher Inn Resort & Marina is a 3.5-star property with free breakfast, free WiFi, and free parking. Another option is Islander Resort, a 3-star resort with free WiFi, free parking, and 3 outdoor pools. You'll also find Cheeca Lodge & Spa, which is a resort offering freebies like WiFi, valet parking, and bicycle rentals.


What are some favorite hotels in downtown Islamorada?

These are some of the most popular hotels in downtown Islamorada:

  • Postcard Inn Beach Resort & Marina is a 3-star resort with a marina, 2 outdoor pools, and a private beach.
  • La Jolla Resort is a hotel offering a private beach, an outdoor pool, and free WiFi.
  • Hadley House Islamorada is a 3-star hotel with a marina, a private beach, and free breakfast.

You'll love Islamorada for its great entertainment, scenic seaside and popular seafood restaurants. In the heart of Islamorada, be sure to visit the well-known Theater of the Sea.


What are the best hotels near Theater of the Sea?

You can get tickets for a performance at this beloved theater, 1.4 mi from central Islamorada. You'll find 32 hotels within a mile of Theater of the Sea, giving you plenty to choose from, and here are some of the top ones:

  • Postcard Inn Beach Resort & Marina: Located 0.5 mi away, this 3-star resort features a marina, 2 outdoor pools, and a private beach.
  • Pelican Cove Resort & Marina: Located 0.3 mi away, this 3-star hotel features a marina, a private beach, and free breakfast.
  • Drop Anchor : Located 0.3 mi away, this 3-star hotel features an outdoor pool, free WiFi, and free parking.

Recent Reviews

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.