Islamorada hotels

Room 1
*Ages of children at time of trip (for pricing, discounts)

What travelers to Islamorada are saying

My wife and I visited the Florida Keys for our first time. We stayed at Marathon, Key West and Islamorada. Islamorada was our favorite! We did a lot of fun stuff at Key West, but we only had 2 days on Islamorada. Next time, we're going to spend most of our trip on that island. Go to the Full Moon Party at the Islamorada Cafe! Next time, we will do some sport fishing and scuba and/or snorkel diving too. Our only regret was wasting 2 days and nights on Marathon, and not spending them here!
Jensen E. May 4, 2015
Islamorada was a great place to stay! We stayed on the lower end, closer to the middle Keys, and were within an easy drive in either direction, which was great since we had a limited time frame and wanted to visit all the major parts of the Keys. We were able to make it over to Key West within about an hour and a half, and Key Largo and Marathon were both within a quick drive. There was plenty to do and see just in Islamorada. No shortage of restaurants and things to do for everyone!
April J. Jul 17, 2015
Islamorada has everything! from shops to CVS to Robbies tarpon feeding!
Alicia R. Aug 31, 2015


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Getting Away to Islamorada

Known as the Sport Fishing Capital of the World, Islamorada is actually a village of islands that offers visitors a wealth of activities to enjoy, including beautiful beaches, a wide array of tropical marine life, and excellent diving. By searching, visitors can find the best rates on Islamorada hotels.

Life on Lower Matecumbe Key

One of the most popular neighborhoods in Islamorada is Lower Matecumbe Key. Visitors will find a host of activities and attractions to enjoy in Lower Matecumbe Key, including the Florida National High Adventure Sea Base and Anne’s Beach. There are numerous accommodation options in Lower Matecumbe Key. Cheeca Lodge, located at Overseas Highway Mile Marker 82, is one of the most popular accommodations in the area. This luxury oceanfront resort offers bungalows, rooms, and suits complete with full kitchens. Visitors can enjoy 27 acres of tropical gardens, tennis courts, a nine-hole pitch and putt golf course, private beach, swimming pools, and a lagoon. There are also two bars and three restaurants located onsite. The number for Cheeca Lodge is 305-664-4651. Rooms start at about $190 per night.

A wide range of dining options is available on Lower Matecumbe, including seafood restaurants inspired by Cuban and Spanish influences. Habanos Oceanfront is located near Caloosa Cove Marina and offers not only ample selections of Cuban favorites but also daily fresh catch specials. Other nearby dining options includes pizza, gourmet dining, and casual island restaurants.

Relaxing on Windley Key

Windley Key is situated between Upper Matecumbe Key and Plantation Key in Islamorada. Attractions in the local area include Theater of the Sea, History of Driving Museum, Mangrove Marina, Everglades Alligator Farm, Joan Purcell Gallery, and the Crane Point Museum and Nature Center. Visitors can also enjoy snorkeling, diving, and fishing in the local area. Snorkeling and diving enthusiasts will find there are numerous sites to explore, including shallow coral reefs, shipwrecks, and mini-walls.

Holiday Isle Hotel offers visitors waterfront views and a convenient location for ocean swimming. Amenities here include a fitness center, hot tubs, two freshwater swimming pools, hot tubs, and a full-service marina. The hotel is also known to offer some of the best nightlife on the entire island. To contact the hotel, visitors can call 305-664-2321. Rates start at about $175 per night. Coconut Grove Resort and Marina is situated near the beach and offers a zero-entry outdoor swimming pool complete with rock formations and a waterfall. The resort also features a private beach, tiki bar, beach chapel, and fitness center. Rates start at $165 per night. The resort’s telephone number is 305-664-0123. Throughout the local area there are numerous dining options featuring an array of diverse cuisine options. Whether travelers are searching for fresh seafood or an upscale gourmet restaurant, there are plenty of choices available.

Islamorada Has It All

Whether you are in the mood to explore the depths of the coral reef, reel in a big one, or soak up some sun on the beach, Islamorada has something to offer everyone. Visitors can find the best prices on Islamorada hotels by searching several different hotels at the same time on

Recently booked Islamorada hotels

Hotel Last booked Stars Price from
Postcard Inn Beach Resort & Marina at Holiday Isle 6 hours ago 4 stars $245
Cheeca Lodge and Spa 1 day ago 5 stars $420
La Siesta Resort and Marina 2 days ago 3 stars $183
Creekside Inn 3 days ago 3 stars $148
Pelican Cove Resort and Marina 3 days ago 4 stars $246
Amara Cay Resort 10 days ago 3 stars $343
Chesapeake Resort 12 days ago 3 stars $199
Islander Bayside 19 days ago 3 stars $379
The Moorings Village and Spa 19 days ago 5 stars Choose dates
Islander Resort, a Guy Harvey Outpost 26 days ago 3 stars $190

Recently Rated Islamorada Hotels

Hotel Reviews Stars Price from
Creekside Inn
4.0 / 5
2 reviews
3 stars $148
Cheeca Lodge and Spa
4.3 / 5
79 reviews
5 stars $420
Chesapeake Resort
3.5 / 5
30 reviews
3 stars $199
Postcard Inn Beach Resort & Marina at Holiday Isle
3.7 / 5
102 reviews
4 stars $245
Islander Bayside
4.7 / 5
3 reviews
3 stars $379
Pelican Cove Resort and Marina
3.9 / 5
61 reviews
4 stars $246
Amara Cay Resort
3.4 / 5
10 reviews
3 stars $343
Islander Resort, a Guy Harvey Outpost
3.9 / 5
67 reviews
3 stars $190
Pines and Palms Resort
4.2 / 5
17 reviews
3 stars $199
La Siesta Resort and Marina
3.7 / 5
22 reviews
3 stars $183

Featured Islamorada Hotels

From $183

1 La Siesta Resort and Marina

3 stars
3.7 / 5 22 reviews

80241 Overseas Hwy

Stay 5 nights, Save 20%

La Siesta Resort & Marina in Florida is on a natural, usually full beach, but there are plenty of activities to take advantage of within the hotel itself, from the poolside Cantina grill to the...

Great place to stay during our fishing trip!
We both liked this hotel because it is neat, clean and has the old keys mom and pop feel. The rooms have a small kitchen where you can prepare a meal and full size frig. where you can freeze your...
Jun 29, 2015
From $245

2 Postcard Inn Beach Resort & Marina at Holiday Isle

4 stars
3.7 / 5 102 reviews

84001 Overseas Highway

Stay 3 nights, Save 15%

The Postcard Inn Beach Resort & Marina at Holiday Isle in Islamorada, located in the Florida Keys, offers a delightful and affordable holiday for those looking to get away from it all. All...

Great location
Room was very nice clean and updated The website didn't say that the tiki hut was closed for remodel ( the reason we wanted to stay their) which was a deal killer if you wanted to party a little
Nov 23, 2015
From $420

3 Cheeca Lodge and Spa

5 stars
4.3 / 5 79 reviews

81801 Overseas Hwy

You'll never have to worry about finding something fun to do during your stay at the Cheeca Lodge and Spa in Islamorada, Florida. Cheeca Lodge and Spa has its own nine-hole golf course that was...

Wedding trip
Great time had by us. Great comfort, good food. Little pricey on the food side but that's the keys for ya.
Nov 17, 2015
From $246

4 Pelican Cove Resort and Marina

4 stars
3.9 / 5 61 reviews

84457 Old Overseas Highway

Stay 3 nights, Save 15%

Featuring a private beach and stunning ocean views, Pelican Cove Resort and Marina offers guests everything they need for a perfect holiday. Located in Islamorada, the hotel boasts 63...

Great family getaway
The hotel was comfortable, very nice rooms. Lovely view. Hotel breakfast was a little disappointing, could have been better.
Oct 16, 2015
From $190

5 Islander Resort, a Guy Harvey Outpost

3 stars
3.9 / 5 67 reviews

82100 Overseas Highway

Designed with vintage 1950s flavor, the Islander Resort offers cottage-style rooms and suites in Islamorada. Located among the palm trees on more than 25 acres of oceanfront property, the resort...

Perfect Location!
This is my third year staying at this resort and we will come back again next year!! It is situated perfectly along the Keys. The fishing dock si great to see and catch many fish and sharks from....
Jul 28, 2015
From $199

6 Chesapeake Resort

3 stars
3.5 / 5 30 reviews

83409 Overseas Highway

Chesapeake Beach Resort rests on 6.5 acres of oceanfront beach and gardens, located in Islamorada, halfway between Miami and Key West. Newly remodeled, the resort offers state-of-the-art amenities...

Loved it
Stayed for 4 nights during Thanksgiving week and had a very nice time with family.. The kids really loved it. Hotel staff were very nice and friendly. Very nice place to stay would recommend to...
Nov 28, 2015
From $379

7 Islander Bayside

3 stars
4.7 / 5 3 reviews

81450 Overseas Highway

Guests of Islander Bayside are welcome to enjoy the amenities of our sister property Islander Resort, located at mile marker 82.1 on the ocean side. Islander Resort has two pools, a Jacuzzi, 1100...

the finest stay in the keys
room was perfect, the staff was exceptional, unfortunately i had to leave a day early, my grandson was hit by a car, my daughter was frantic!! but everything turned out good. i will return again-
Nov 21, 2015
From $199

8 Pines and Palms Resort

3 stars
4.2 / 5 17 reviews

80401 Old Highway

Cottages, suites and duplexes in a tropical setting on the Atlantic Ocean in Islamorada. Each one-bedroom unit comes with a king or queen bed, a fully equipped kitchen, living room with sofa bed...

Great base to explore the keys
We loved this place. We had a nice kitchen and enjoyed the area. The room was clean and roomy enough. The pool area was great, with a little bar and nice views. The staff were helpful when we...
Jul 19, 2015

9 The Moorings Village and Spa

5 stars
Not yet reviewed

123 Beach Road

Situated in the heart of Islamorada halfway between Miami and Key West The Moorings is an 18-acre property harboring 18 cottages and homes on what was once a coconut plantation. Ranging from one to...

From $343

10 Amara Cay Resort

3 stars
3.4 / 5 10 reviews

80001 Overseas Highway

Advance Purchase - Save 10%

Anchored in the laid-back style and carefree atmosphere that make Islamorada the sport fishing capital of the world, the new Islamorada Resort introduces a new level of luxury to the Upper Keys....

anniversary weekend
Hotel was nice....friendly staff but under construction. we chose it for the location to Bud and Marys- within walking distance. we never ate at restaurant but food looked tasty. When we checked...
Sep 9, 2015