join Orbitz Rewards

By clicking, I agree to the terms

Islamorada hotels

Search 12 Islamorada Hotels

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

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
Postcard Inn Beach Resort & Marina at Holiday Isle 2 hours ago 4 stars $179
Pelican Cove Resort and Marina 7 hours ago 4 stars $161
La Siesta Resort and Marina 1 day ago 3 stars $172
Islander Resort, a Guy Harvey Outpost 3 days ago 3 stars $245
Chesapeake Resort 3 days ago 3 stars $189
Creekside Inn 4 days ago 3 stars $149
Pines and Palms Resort 4 days ago 3 stars $179
Cheeca Lodge and Spa 5 days ago 5 stars $179
Casa Morada 7 days ago 3 stars $419

Recently Rated Islamorada Hotels

Hotel Reviews Stars Price from
Cheeca Lodge and Spa
4.2 / 5
71 reviews
5 stars $179
Pines and Palms Resort
4.2 / 5
13 reviews
3 stars $179
Postcard Inn Beach Resort & Marina at Holiday Isle
3.7 / 5
91 reviews
4 stars $179
Pelican Cove Resort and Marina
3.8 / 5
52 reviews
4 stars $161
Chesapeake Resort
3.5 / 5
30 reviews
3 stars $189
Islander Resort, a Guy Harvey Outpost
3.8 / 5
67 reviews
3 stars $245
La Siesta Resort and Marina
3.7 / 5
19 reviews
3 stars $172
Islander Bayside
4.0 / 5
1 reviews
3 stars $379
Casa Morada
4.7 / 5
3 reviews
3 stars $419
Amara Cay Resort
3.3 / 5
9 reviews
3 stars Choose dates

Islamorada hotels

  • Hotels

Featured Islamorada Hotels

From $179

1 Cheeca Lodge and Spa

5 stars
4.2 / 5 71 reviews

81801 Overseas Hwy Map

Luxury guest rooms, fine dining, private-beach location in IslamoradaCheeca Lodge & Spa sits on 27 oceanfront acres of Upper Matecumbe Key in the village of Islamorada. It's located 78 miles... More

great trip
it was well worth the money great view friendly people
Jan 28, 2015
From $245

2 Islander Resort, a Guy Harvey Outpost

3 stars
3.8 / 5 67 reviews

82100 Overseas Highway Map

Comfortable, kitchen-equipped rooms on private beach in IslamoradaDesigned with vintage 1950s flavor, the Islander Resort offers cottage-style rooms and suites in Islamorada. Located among the palm... More

Have a good time there
Got a good deal for this hotel. This resort hotel has a nice facilities. Love beach areas. Good location between Key West and Miami.
Dec 29, 2014
From $172

3 La Siesta Resort and Marina

3 stars
3.7 / 5 19 reviews

80241 Overseas Hwy Map

Stay 3 or 4 Nights, Save 10% Off

A full tropical experience with water-based sports and heated pool La Siesta Resort & Marina in Florida is on a natural, usually full beach, but there are plenty of activities to take advantage... More

nice but needs more customer service
this is a very nice place with a good location but the room was only cleaned once in three days, the water pressure in shower was very low and the air conditioner was very loud. I complained three...
May 7, 2014
From $189

4 Chesapeake Resort

3 stars
3.5 / 5 30 reviews

83409 Overseas Highway Map

Ocean-view rooms and villas on Islamorada beachChesapeake Beach Resort rests on 6.5 acres of oceanfront beach and gardens, located in Islamorada, halfway between Miami and Key West. Newly... More

It's ok
Upon arriving we found all of our towels in a garbage bag outside of our room. We had to question if they were clean or dirty. The room was clean. The wifi was free but so limited that we couldn't...
Dec 30, 2014
From $179

5 Postcard Inn Beach Resort & Marina at Holiday Isle

4 stars
3.7 / 5 91 reviews

84001 Overseas Highway Map

Stay 3 or 4 Nights, Save 10% Off

Marina and Florida Keys accommodations on a lively beachfront The Holiday Isle Resorts & Marina offers the classic Florida Keys experience of cocktails and marina life with great views across... More

great couple getaway
Loved the Tiki Bar... (Amber & Vince were awesome behind the bar!), was a Bit upset that the other bar RumRunners featured on site was closed for renovations since there was no mention of this when...
Jan 24, 2015
From $161

6 Pelican Cove Resort and Marina

4 stars
3.8 / 5 52 reviews

84457 Old Overseas Highway Map

Stay 3 or 4 Nights, Save 10% Off

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... More

Was a great hotel for the price
We have stayed at Pelican Cove numerous times. It was a great hotel for the price, however, since our last stay in Feb 2014 the price has gone up significantly and is no longer affordable.
Jan 19, 2015
From $379

7 Islander Bayside

3 stars
4.0 / 5 1 reviews

81450 Overseas Highway Map

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... More

Wedding in the Keys
It was fabulous. We would definitely stay there again.
Oct 17, 2014

8 Amara Cay Resort

3 stars
3.3 / 5 9 reviews

80001 Overseas Highway Map

Stay 3 or 4 Nights, Save 10% Off

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.... More

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 $509

9 The Moorings Village and Spa

3 stars
Not yet reviewed

123 Beach Road Map

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... More

From $419

10 Casa Morada

3 stars
4.7 / 5 3 reviews

136 Madeira Road Map

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. More

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 $179

11 Pines and Palms Resort

3 stars
4.2 / 5 13 reviews

80401 Old Highway Map

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... More

Great Place to Relax
The hotel is lovely. Its a bit rustic and on the water which makes it a great place to relax. You can swim in the ocean or a heated pool and there is lots to do nearby.
Jan 28, 2015
From $149

12 Creekside Inn

3 stars
Not yet reviewed

90611 Old Highway, Map

24hrs SAle 15%

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