Islamorada hotels

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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
Great place for fishing or just playing on the beautiful waters. The dinning selections are excellent!
James F. Jun 28, 2015

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 Orbitz.com, 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 Orbitz.com.

Recently booked Islamorada hotels

Hotel Last booked Stars Price from
La Siesta Resort and Marina 4 hours ago 3 stars $191
Cheeca Lodge and Spa 4 hours ago 5 stars $201
The Moorings Village and Spa 1 day ago 5 stars $472
Pelican Cove Resort and Marina 2 days ago 4 stars $151
Creekside Inn 2 days ago 3 stars $118
Islander Resort, a Guy Harvey Outpost 3 days ago 3 stars $159
Chesapeake Resort 3 days ago 3 stars $143
Pines and Palms Resort 5 days ago 3 stars $129
Postcard Inn Beach Resort & Marina at Holiday Isle 6 days ago 4 stars $155
Amara Cay Resort 11 days ago 3 stars $282

Recently Rated Islamorada Hotels

Hotel Reviews Stars Price from
Cheeca Lodge and Spa
4.3 / 5
75 reviews
5 stars $201
Islander Resort, a Guy Harvey Outpost
3.9 / 5
67 reviews
3 stars $159
Islander Bayside
4.5 / 5
2 reviews
3 stars $296
Pines and Palms Resort
4.2 / 5
17 reviews
3 stars $129
La Siesta Resort and Marina
3.7 / 5
22 reviews
3 stars $191
Postcard Inn Beach Resort & Marina at Holiday Isle
3.7 / 5
99 reviews
4 stars $155
Pelican Cove Resort and Marina
3.9 / 5
56 reviews
4 stars $151
Chesapeake Resort
3.4 / 5
28 reviews
3 stars $143
Casa Morada
4.7 / 5
3 reviews
3 stars $299
Amara Cay Resort
3.3 / 5
9 reviews
3 stars $282

Featured Islamorada Hotels

From $201

1 Cheeca Lodge and Spa

5 stars
4.3 / 5 75 reviews

81801 Overseas Hwy

Cheeca Lodge & Spa sits on 27 oceanfront acres of Upper Matecumbe Key in the village of Islamorada. It's located 78 miles from Miami International Airport and 80 miles from Key West. For 55...

4 Ladies Pampered to the MAX
I convinced my friends we should cut our annual vacation in Key West short so that we could explore other destinations located in the Keys. I found Cheeca Lodge and Spa online and WOW did it...
Jul 1, 2015
From $159

2 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 $191

3 La Siesta Resort and Marina

3 stars
3.7 / 5 22 reviews

80241 Overseas Hwy

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 $151

4 Pelican Cove Resort and Marina

4 stars
3.9 / 5 56 reviews

84457 Old Overseas Highway

Every one of our tropical standards and suites captures a breathtaking water view. Relax on your private balcony that overlooks either the magnificent Atlantic Ocean or Pelican Coves own sheltered...

Pathetic hotel
Unfortunately I did not review this hotel when my memory was fresh. As best I remember now It had no table of any kind in the room, the refrig. did not work because it was in a cabinet and...
May 22, 2015
From $143

5 Chesapeake Resort

3 stars
3.4 / 5 28 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...

First trip to the keys
The hotel itself could use some renovations. The paint was peeling in the bathroom, the fan in the bathroom doesn't work, had a few issues with the toilet not flushing. The porch is screened in but...
Feb 3, 2015
From $155

6 Postcard Inn Beach Resort & Marina at Holiday Isle

4 stars
3.7 / 5 99 reviews

84001 Overseas Highway

The Holiday Isle Resorts & Marina offers the classic Florida Keys experience of cocktails and marina life with great views across the ocean. With a busy beachfront, outdoor tiki bar and a...

Great for all travellers
This hotel was low key and had just the right amount of fun mixed with relaxation. The beach is small and they kick you off if there is a wedding, but there is a nice pool and plenty of other...
Jun 20, 2015
From $129

7 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
From $296

8 Islander Bayside

3 stars
4.5 / 5 2 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...

What a fantastic place!
Between the location and the amenities you get staying here I can't say enough good words about the Islander Bayside. The only warning I could mention is that there are two units a little close to...
Jul 20, 2015
From $282

9 Amara Cay Resort

3 stars
3.3 / 5 9 reviews

80001 Overseas Highway

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....

Great Room - a little loud
Our room was great - the hotel was clean and the pool was great. Only small complaint we had was the room was pretty loud on busy nights - could hear everything through the walls.
Jul 28, 2014
From $472

10 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 $299

11 Casa Morada

3 stars
4.7 / 5 3 reviews

136 Madeira Road

Guests of Casa Morada enjoy the seclusion of a private tropical island but are only minutes away from some of the best dining and outdoor activities in the Florida Keys.

Perfect couples retreat
Had a wonderful time at Casa Morada. Staff was warm and friendly from the moment we arrived. Ross the bartender was friendly and helpful throughout our entire stay. We felt like we were on our own...
Aug 15, 2014
From $118

12 Creekside Inn

3 stars
Not yet reviewed

90611 Old Highway,

Flash Sale, 20% Off

Strategically located ocean side of Tavernier Creek Bridge, with direct access to the Atlantic Ocean or Florida Bay, we are at the heart of everything. We have casual and fine-dining restaurants,...