Midway along the Overseas Road in the stunning Florida Keys, Islamorada offers travelers a private and luxurious getaway. This charming haven, Islamorada, Florida, although small (it’s just around seven square miles in size), has a remarkable combination of art, history, wonderful beaches, and a nice range of exclusive and opulent resorts.

Visitors to Islamorada Florida will never run out of things to do, and the wide choice of resorts makes it simple to locate the ideal spot to stay. You should go fishing while you’re in Islamorada since it is the sportfishing capital of the world. Numerous charters and boat rentals are available here to assist you; some are even associated with the top resorts and have concierge personnel to help you with arrangements while you’re there.

Our selection of the top resorts in Islamorada Florida will help you discover the perfect place to lay your head, whether you’re looking to spend time building sandcastles and splashing about in the green seas with your children or you want to have a relaxing beach vacation as a couple in a luxurious hotel with a spa.

#1. Casa Morada

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Casa Morada is one of the must-visit resorts in Islamorada Florida. A beautiful, privately owned resort with sixteen rooms, was built with the laid-back attitude of the Caribbean. Privateness, serenity, and calm characterize the environment. The staff is famous for their warmth and professionalism. Raymond Jungles, a well-known Miami landscape architect known for his lush, natural landscapes, designed the property’s award-winning garden settings. The stunning private island of Casa Morada is the resort’s main attraction. 

Furthermore, the island contains a fresh pool, an exclusive cabana, and an open-air gazebo bar with incredible views of the Gulf of Mexico. Only a beautiful footbridge leads to it. Casa Morada is 90 minutes south of Miami International Airport, whereas Key West is 90 minutes north. For visitors to Casa Morada, boat transportation is also offered. The Casa Morada welcomes guests with pets that are 16 years of age or older.

Read Also: BEST PLACES TO STAY IN FLORIDA: Neighborhoods & Hotels

#2. Chesapeake Beach Resort

resorts in islamorada florida
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Dreams are made of the vistas of the Atlantic from the Chesapeake Beach Resort. Sugar-white beaches, towering palm trees, green lakes, and a sky so blue that it seems unreal are all present together. Though it is! This freshly renovated resort, which had its most recent renovation in 2023, is light, airy, and modern. This 3-star resort has naturally furnished hotel rooms and balconies where visitors can take a breath of salty air while being cooled by coastal breezes.

All accommodations have a balcony with either an ocean or an island view; you can’t go wrong with either. Choose a villa if you’re vacationing with children. You’ll appreciate the extra room as well as the exclusivity. The resort’s private beach is nestled in a peaceful, sheltered bay, making it a perfect holiday spot for families with small children. The calm, sheltered waters make it safer for children to enjoy themselves. On a hot day, the two beachfront pools are ideal for cooling down.

#3. Cheeca Lodge and Spa

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Cheeca Lodge & Spa, known as the “Queen of the Florida Keys,” has been an exclusive retreat for celebrities, business leaders, and U.S. presidents for over 70 years. A porte-cochere entrance, classic Florida Keys design, and a tradition of “barefoot elegance” are all features of the 27-acre Cheeca resort in Islamorada. In addition to a cafe and a luxurious lobby bar, Cheeca boasts three different restaurants.

The flagship restaurant of Cheeca, Atlantic’s Edge, offers a seasonal fine-dining menu with fresh local seafood, prime steaks, as well as organic local produce. Nikai Sushi Bar and Restaurant offers the freshest sushi in the Florida Keys, Asian-inspired cuisine, and an unusual selection of Japanese sake and wine. Mia Cucina, a family-friendly restaurant, transports Naples, Italy, into the heart of Islamorada and serves made-to-order artisan pizzas, pasta, and salads.

#4. Islander Resort

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Image Source: TripAdvisor

It’s easy to understand why the 3-star Islander Resort is so popular with visitors. This delicious Atlantic-facing site radiates natural beauty in the shape of towering, green palm trees and a pristine 24 acres featuring a white, sandy beach, making it one of the top Islamorada Florida Keys resorts for families. The two heated saltwater pools and the on-site splash pad will keep the kids entertained. Go snorkeling, kayaking, paddle boarding, fishing, or bodysurfing at the beach; the options are unlimited. Land-based activities include free bike rentals, basketball, volleyball, ping pong, and shuffleboard.

Moreover, the Islander Resort offers two restaurants, a specialty suite with a kitchen, and a dog park. It also has a 7,500-square-foot museum featuring intriguing exhibits and a $2 discount on entrance. Pets are welcome, and there is a dog park on the grounds. The Florida Keys History and Discovery Center is located on the resort’s north end and features intriguing exhibits.

#5. Amara Cay Resort

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The laid-back manner and carefree environment that have made Islamorada the Sport Fishing Capital of the World are at the heart of Amara Cay Resort. Amara Cay Resort harmoniously merges activity and leisure, reflecting the relaxed serenity of the Upper Keys. A dazzling beachfront pool greets early risers as hammocks dot the sandy shoreline and palm trees sway in the air. It’s no surprise that Amara Cay was voted the winner of the International Interior Design Association’s 2015 Sandi Design Award for Design Excellence Hospitality, which highlighted our adept blend of a calm environment and elegant elegance.

#6. The Caribbean Resort

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One of the luxurious resorts in Islamorada Florida is this. Guests at Upper Matecumbe Key’s appropriately titled The Caribbean Resort stay in one of a number of charming, upmarket houses filled with Caribbean flair (think teak and mahogany furnishings and vividly colored textiles). This popular 3-star resort also has furnished porches, which contribute to the island vibe, while the outdoor grill, in-unit kitchen, and washer/dryer make it simple to feel at home in this lovely paradise. Your sole wish will be for more vacation time.

The resort’s facilities are available to renters, whether they want to stay for a day, a week, or a month. These include a stunning pool that is kept cool by the tropical landscape that is teeming with banana, pineapple, and palm trees. Cool evenings are made more bearable by a hot pool, and tourists are generally calmed by waterfalls. Additionally, pursuits like bicycle riding, kayaking, and stand-up paddleboarding are free. Why not try your luck fishing while you’re there at the 5-foot pier by borrowing a fishing rod? Dawn is the best time to catch a large fish, according to a fishing insider.

#7. Pelican Cove Resort and Marina

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The laid-back way of life in the Florida Keys is exemplified by Pelican Cove Resort and Marina. The resort instantly transforms guests into a tropical paradise with its 63 waterside rooms and suites, pool, saltwater lagoon, cabana bar and café, marina, and water sports and fishing excursions. Visitors can engage in as much activity as they like while enjoying the laid-back atmosphere of a remote luxury vacation thanks to the abundance of activities available on the property and on the adjacent islands. 

Pelican Cove Resort is the “key” location to unwind and alter your location as well as your attitude because there are several palm trees and areas of shade to retreat to. So, Pelican Cove Resort is the spot you want to be if you enjoy lazing around in the sun and looking at the Atlantic Ocean’s sparkling blue seas.

#8. Postcard Inn Beach Resort and Marina

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Looking for a peaceful Florida vacation in a beautiful location? It can be found at Holiday Isle’s 3-star Postcard Inn Beach Resort & Marina. Guests spend the majority of their time relaxing on the resort’s lovely beach, laid out on plush lounge chairs on the soft, golden sand. They only get up to cool down in the green waves off-shore or take a plunge in one of the two crystal-clear pools.

Furthermore, the daily resort fee covers shuttle service within a four-mile area of the resort, bicycle rentals, use of kayaks and paddleboards, beach chairs, and towels. Visitors can eat at one of the four on-site restaurants or have a freshly made coffee at the Starbucks café. Choose from one of the many clean, island-themed guest rooms for your daily refuge, or rent a cottage for a more private and spacious haven.

The resort’s sister properties, La Siesta Resort & Marina, Amara Cay Resort, as well as Pelican Cove Resort & Marina, all give guests access to their dining establishments and other facilities. Bring your favorite family members, including your four-legged friends, to join in the excitement.

#9. La Siesta Resort and Villas

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La Siesta Resort and Villas have a lovely beachfront pool that is heated, as well as a private beach that is in excellent condition. The lodgings are huge and lovely here. They consist of large guest rooms and multi-bedroom suites, as well as cheerfully decorated private cottages and getaway properties with easy access to the beach and stunning views of the Atlantic. Not bad at all!

A shuttle service, breakfast, and fishing supplies are all included in the daily resort fee. Rentals of bicycles, kayaks, paddle boats, and paddleboards are also free. Another benefit is that visitors can utilize the facilities of Postcard Inn, Pelican Cove, and Amara Cay, the sister resorts of La Siesta.

La Siesta Resort & Villas offers an immaculate private beach and a heated beachfront pool. The accommodations are large and beautiful, with easy access to the beach and stunning views of the Atlantic Ocean. Breakfast, a shuttle, and fishing gear are included in the daily resort charge, as are free rentals of bicycles, kayaks, paddle boats, and paddleboards. Additionally, in this Islamorada Florida resort visitors can take advantage of the facilities of Postcard Inn, Pelican Cove, and Amara Cay, sister resorts of La Siesta.

#10. Pines and Palms Resort

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Who desires to spend their holiday crammed into a little hotel room? Not us. You will enjoy your stay at Pines & Palms Resort if you enjoy a bit of additional room while on vacation, especially if you have young children with you. Spacious apartments and cottages with one, two, or three bedrooms are available at this five-acre resort, and each one has a full kitchen. Along with a heated freshwater pool and tiki bar, the resort has a village-like feel.

Schedule a yoga session, go fishing from the pier, or take out a bicycle, kayak, or paddleboard for a loan. For some peace and quiet, go to the orchid nursery, then relax by the beach to get some rays. Nobody will be mad at you for relaxing in a hammock under a canopy of palms. Getting there by boat? The resort offers free docking for your boat.

#11. The Moorings Village

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The Moorings Village offers a serene atmosphere with a hammock on the oceanfront. This lovely location, which was formerly a coconut farm, is a natural wonderland with more than 800 palm trees, paths covered in orchids, and shimmering ocean waves. The property is scattered with opulent villas that provide guests with a sumptuous escape from reality. These lovely rooms are spacious and light, and they include kitchens in addition to a very welcome sense of rest.

There are kayaks, paddleboards, bikes, a fitness center, tennis courts, as well as a swimming pool available to guests. Although there are no restaurants on-site, a lot of dining establishments are close by, and the staff can readily make dinner reservations on your behalf. It’s not difficult to walk to the great seafood restaurant, Chef Michael’s, which offers fresh fish daily.

Is There a Town in Islamorada?

The lovely Florida Keys are home to Islamorada, the Village of Islands. Mile Markers (MM) 90 to 72 roughly correspond to the borders. A tourist-focused neighborhood an hour south of Miami, Islamorada is made up of four islands that cover 18 linear miles of land and have a total size of around 3,900 acres.

Where is Islamorada Florida Keys?

Islamorada is an officially recognized community in Florida’s Monroe County (also known as Islas Morada on occasion). On five islands in the Florida Keys (Tea Table Key, Lower Matecumbe Key, Upper Matecumbe Key, Windley Key, and Plantation Key), it is situated immediately between Miami and Key West.

Is Islamorada Expensive?

Our cost of living calculator indicates that Islamorada is 55% more costly than the US average and 46% more expensive than the typical city in Florida to live in. This is based on a 2 bedroom apartment and a $72,000 yearly wage. The price of food in Islamorada is more expensive than the national average.

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