Hotels in Islamorada

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Popular hotels in Islamorada

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82100 Overseas Highway, Islamorada, FL, United States
Islander Resort is a unique destination in Islamorada featuring guest rooms and an unrivaled collection of premier suites inspired by the classic elegance of the Florida Keys. Nestled among the palm trees on more than 24 oceanfront acres in the Village of Islamorada, the resort includes 114 luxury guest rooms and suites that enhance the charm of our tropical destination. Guests enjoy access to a variety of on-site amenities including two oceanfront pools, beachside hammocks, complimentary bikes, and Seaside Sports your hub for games and activities under the sun. Dine oceanside at Tides Beachside Bar & Grill, enjoy fresh food with your toes in the sand at Coccoloba, grab a bite and a refreshing drink poolside at Sandys Beach Shack, or start your day with a gourmet coffee at Drift. From sunrise breakfasts to sunset happy hours, Islander Resort offers a laid-back taste of the Florida Keys. Just a short drive or shuttle ride away, Bayside Villas by Islander Resort offers 25 charming, contemporary cottages and 14 boat slips nestled amid lush tropical foliage. Guests enjoy access to all amenities at Islander Resort while staying in spacious villa accommodations complete with beautifully equipped gourmet kitchens, top-of-the-line stainless steel appliances, and granite countertops. When youre ready to explore, were steps away from the best sightseeing, dining, and shopping in the Florida Keys. Walk or bike to nearby boutiques, restaurants, historic sites, and museums. Bayside Villas is also home to Islander EcoAdventures, your connection to kayaking, paddleboarding, and on-the-water exploration. Our charming, contemporary resort, world-class amenities, and amazing location will make your stay a true escape from reality. With health and well-being top of mind, we have developed REST ASSURED, a 5-point program designed to ensure guests and staff may be put at ease while on property. Program standards, including advanced cleaning protocols, physical distancing, and transparent communication, are based on guidance from the Centers for Disease Control (CDC), World Health Organization (WHO), and American Hotel and Lodging Association (AHLA). No detail has been left unturned and we thank you for staying with us.
Free Wi-Fi
9.0
Excellent
1914 reviews
Location
0.5 km from city centre
84001 Overseas Highway, Islamorada, FL, United States
Welcome to Three Waters Resort & Marina, a one-of-a-kind destination named for the rare meeting of the Atlantic Ocean, Florida Bay, and the Gulf of Mexico. Set on 15 waterfront acres—the “Sportfishing Capital of the World”—our resort in Islamorada, Florida blends island adventure with serene relaxation. Relax in a range of island-inspired guestrooms and ocean view suites, or retreat to The Cove, our adults-only resort within a resort. Discover tropical beauty and the spirit of the Florida Keys, plus nine unique dining options—from the wood-fired warmth of Kindler to the iconic Tiki Bar. Cruise between experiences at our beachfront hotel in Islamorada aboard our water taxi, Rum Runner. At our full-service marina, a seasoned fleet of captains welcomes anglers of every level. Whether you’re seeking world-class fishing, a family vacation, romantic escape, upscale retreat, or a dream beach wedding, Three Waters Resort & Marina is your ultimate Florida Keys resort. 
Free Wi-Fi
8.3
Excellent
1457 reviews
Location
2.9 km from city centre
80241 Overseas Highway, Islamorada, FL, United States
Just off the Overseas Highway and in front of the ocean, this Islamorada hotel offers an on-site marina. The beachfront hotel features an outdoor pool. WiFi is included in the resort fee. The suites and cottages at La Siesta Resort & Villas are equipped with a cable TV and air conditioning. On site, SIDECAR bar serves light fares, beer, and wine daily. Activities such as boating, fishing, jet skiing and snorkeling can be arranged. The on-site marina offers both gulf-side and ocean-side slips while non-motorized watersports equipment and bicycles are provided for guests' use. Theater of the Sea is 3.7 mi away from the accommodations while Anne's Beach is located 6.7 mi away.
Parking
8.2
Excellent
1277 reviews
Location
3.3 km from city centre
83409 Overseas Highway, Islamorada, FL, United States
At Chesapeake Beach Resort, you can relax at one of the 2 outdoor swimming pools, play on the private white sand beach, or spend the day at a marina.
Free Wi-Fi
Parking
8.3
Excellent
1233 reviews
Location
2.0 km from city centre
80051 Overseas Highway, Islamorada, FL, United States
An outdoor pool, laundry facilities, and a garden are available at this hotel. Free WiFi in public areas and free self parking are also provided. Additionally, barbecue grills, a picnic area, and a front-desk safe are onsite.
Free Wi-Fi
Air conditioning
8.5
Excellent
754 reviews
Location
3.7 km from city centre
81450 Overseas Highway, Islamorada, FL, United States
Nestled in the heart of Islamorada amid lush tropical foliage sits twenty-five charming, contemporary cottages and 14 boat slips known as Bayside Villas by Islander Resort. Enjoy luxurious accommodations complete with beautifully equipped gourmet kitchens, featuring top-of-the-line stainless steel appliances and granite countertops. When youre ready to explore, we are only steps away from some of the best sightseeing, dining, and shopping experiences in the Florida Keys. Walk or bike to nearby boutique shops, restaurants, historical sites, and museums. Bayside Villas is also home to Islander EcoAdventures, your connection to kayaking, paddle boarding, and more. Guests of Bayside Villas also enjoy full access to the amenities of Islander Resort, located just across the street. The property offers 14 boat slips available to guests on a first-come, first-served basis. Bayside's convenient marina access makes it easy to enjoy the surrounding waters and plan your perfect day on the ocean. Our charming, contemporary resort, world-class amenities, and amazing location will make your stay a true escape from reality.
Free Wi-Fi
Parking
8.6
Excellent
520 reviews
Location
1.9 km from city centre
117 Carroll Street, Islamorada, FL, United States
Along with a marina, this hotel has an outdoor pool and a hot tub. Other amenities include free use of bicycles, laundry facilities, and wedding services.
Free Wi-Fi
Air conditioning
Location
0.7 km from city centre

Travel insights for hotels in Islamorada

Use these up-to-date, data-driven insights about booking a hotel in Islamorada including ideal times to book, pricing trends, and more.

What is the cheapest month to book a hotel in Islamorada?

The cheapest month to book a hotel in Islamorada is September ($564). Conversely, the most expensive month to stay in Islamorada is January ($1,464).

What is the cheapest day to stay in a hotel in Islamorada?

The cheapest day to stay in Islamorada is Wednesday ($505). On the other hand, travellers can expect to pay the most on Tuesday, when the average nightly price is $621.

How much is a hotel in Islamorada tonight?

Users have found prices for hotels in Islamorada tonight starting as low as $295, rising to an average cost of $644, based on searches in the last 72 hours. Prices start from $538 for a 4-star hotel in Islamorada for tonight.

How much is a Islamorada hotel room this weekend?

In the past 72 hours, we’ve seen prices for hotels in Islamorada this weekend for as little as $346/night. If you’re specifically looking for a 3-star hotel this weekend, our users have found prices as low as $346/night. For a 4-star hotel in Islamorada, the cheapest rate recently found was $610/night for this weekend.

How far ahead should you book a hotel in Islamorada?

Save money by booking a hotel at least 79 days before your trip to Islamorada. The lowest price found when booking 79 days ahead was $420 per night.

Cheapest hotels in Islamorada, Florida

These Islamorada properties charge the lowest price per night of those we've come across. If you have the flexibility, change the dates selected to compare prices.
243 Treasure Harbor Drive, Islamorada, FL, United States
6.6 km from city centre
Free Wi-Fi
$217
Avg. per night
84951 Overseas Highway, Islamorada, FL, United States
4.1 km from city centre
Free Wi-Fi
Parking
$219
Avg. per night
80015 Overseas Highway, Islamorada, FL, United States
3.8 km from city centre
Free Wi-Fi
$223
Avg. per night
76261 Overseas Highway, Islamorada, FL, United States
9.7 km from city centre
Free Wi-Fi
Parking
$223
Avg. per night
68500 Overseas Highway, Islamorada, FL, United States
21.9 km from city centre
Free Wi-Fi
Parking
$229
Avg. per night
82749 Overseas Highway, Islamorada, FL, United States
0.5 km from city centre
Free Wi-Fi
Parking
$233
Avg. per night
82200 Overseas Highway, Islamorada, FL, United States
0.2 km from city centre
Free Wi-Fi
Parking
$240
Avg. per night
84801 Overseas Highway, Islamorada, FL, United States
3.8 km from city centre
Free Wi-Fi
Parking
$256
Avg. per night
82216 Overseas Highway, Islamorada, FL, United States
0.1 km from city centre
Free Wi-Fi
Parking
$272
Avg. per night
81801 Overseas Highway, Mile Marker 82, Islamorada, FL, United States
1.0 km from city centre
Free Wi-Fi
$273
Avg. per night
136 Madeira Road, Islamorada, FL, United States
0.3 km from city centre
Free Wi-Fi
Parking
$290
Avg. per night
80401 Old Highway, Islamorada, FL, United States
3.2 km from city centre
Free Wi-Fi
$314
Avg. per night
84959 Overseas Highway, 222, Islamorada, FL, United States
4.2 km from city centre
Free Wi-Fi
Parking
$336
Avg. per night
80001 Overseas Highway, Islamorada, FL, United States
3.9 km from city centre
$340
Avg. per night
73801 Overseas Highway, Islamorada, FL, United States
13.8 km from city centre
Free Wi-Fi
Parking
$340
Avg. per night

Hotel prices in Islamorada

We've come across the following hotels in Islamorada with different price and hotel class options. We've also highlighted the most popular hotels and best value within each hotel class.
4 stars +
3 stars
84801 Overseas Highway, Islamorada, FL, United States
80401 Old Highway, Islamorada, FL, United States
81450 Overseas Highway, Islamorada, FL, United States
117 Carroll Street, Islamorada, FL, United States
68500 Overseas Highway, Islamorada, FL, United States
2 stars and under
76261 Overseas Highway, Islamorada, FL, United States

Other accommodation in Islamorada

82200 Overseas Highway, Islamorada, FL, United States
0.2 km from city centre
Free Wi-Fi
Parking
$240
Avg. per night
80051 Overseas Highway, Islamorada, FL, United States
3.7 km from city centre
Free Wi-Fi
Air conditioning
$387
Avg. per night
80015 Overseas Highway, Islamorada, FL, United States
3.8 km from city centre
Free Wi-Fi
$223
Avg. per night
82100 Overseas Highway, Islamorada, FL, United States
0.5 km from city centre
Free Wi-Fi
$467
Avg. per night
82216 Overseas Highway, Islamorada, FL, United States
0.1 km from city centre
Free Wi-Fi
Parking
$272
Avg. per night

Where to stay in Islamorada

Utilise the map to find properties close to the Islamorada area(s) or attractions you plan on visiting. You can find more information on a particular hotel within the map by clicking on its name.

About Islamorada

Swaying palms, sugar-white sand and rainbow-coloured coral reefs await in Islamorada. The lively Florida Keys village is made up of six islands sandwiched between the Florida Strait and Everglades National Park. Bask on the sand at Anne’s Beach and enjoy a picnic in palm-shaded Founders Park, also known as the Gem of Islamorada.

There are some great places to drink and dine in Islamorada, including excellent seafood restaurants and a hip craft brewery. The History of Diving Museum charts the village’s maritime heritage and showcases metal helmets, centuries-old treasure chests and other artefacts.

Day trips to Indian Key Historic State Park take you to a tiny island dotted with centuries-old ruins. The park can only be accessed by boat, with kayak rentals available from local outfitters in Islamorada. Eco tours depart from the marina and get you up close with dolphins, crocodiles and manatees. They’re also a great way to explore the lush mangrove forests that surround Islamorada.

Getting there

Islamorada is located in the Florida Keys, a two-hour drive from Miami and Key West. Rental cars offer the freedom to explore the Florida Keys at your own pace. Key West International Airport is a two-hour drive away.

Facts about staying in Islamorada

  • What are the best hotels in Islamorada?

    Chesapeake Beach Resort (8.3/10 from 1,233 reviews), Coconut Cove Resort and Marina (8.3/10 from 361 reviews), and Cheeca Lodge & Spa (8.4/10 from 1,485 reviews) are all highly rated places to stay in Islamorada.

  • How much is a cheap hotel in Islamorada?

    Over the last 3 days, Islamorada hotels have been found for as cheap as $173/night in searches by HotelsCombined users.

  • What are some other cities to stay in when visiting Florida?

    In addition to Islamorada, travellers opt to visit Orlando when visiting Florida. Miami Beach is also a popular choice to visit.

  • How many hotels are there in Islamorada?

    In total, there are 533 hotels to choose from in Islamorada, compared to 199,887 properties in Florida.

See more FAQs

Find better results for your stay in Islamorada

Consider these popular 3-star hotels in Islamorada