Islamorada is a tropical paradise and a premier destination in the Florida Keys. Just 90 minutes south of Miami, this “Sports Capital of the World” offers endless outdoor recreation on and near the water. Go deep sea fishing, snorkeling, swimming off a beautiful beach, and hand-feeding tarpon at Robbie’s of Islamorada, then take advantage of nearby seafood restaurants serving delicious tarpon sandwiches and conch fritters. Finally, make the most of your visit by booking a stay at one of these best Islamorada hotels, featuring on-site perks like outdoor pools, ocean-view rooms, and easy access to water activities.
Beautiful Islamorada offers visitors an intimate and luxurious escape halfway up the Overseas Highway in the Florida Keys. Although small at only seven square miles, this pretty paradise has an impressive mix of art, history, and beautiful beaches.
Islamorada’s wide selection of fun attractions keeps visitors busy, and the wide variety of resorts makes it easy to find the perfect place to stay. In addition, Islamorada is known as the sport fishing capital of the world, so you’ll want to take up some fishing while you’re there.
Whether you want to build sand castles and splash around in emerald waters with your kids or want to enjoy a quiet beach vacation at a luxurious spa hotel, you’ll find a great place to rest in Islamorada.
Use our list of the best resorts in Islamorada to help you choose the right accommodation for your trip.
Note: Some businesses may be temporarily closed due to current global health and safety concerns.
1. Cheeca Lodge & Spa
A long wooden jetty juts out into the azure waters of the Atlantic off Cheeca Lodge & Spa’s white sand beach. She welcomes guests, including presidents and celebrities, to bask in the peaceful bliss enveloping this lush island.
Pillowtop mattresses adorn the comfortable beds in each spacious guest room and suite, adorned with tropical-themed decor and balconies. After wandering the sprawling 27-acre property, these rooms provide the perfect environment to unwind. Don’t worry; bikes are on hand to make it easy to get from place to place.
Three restaurants will satisfy your cravings as you indulge in ocean views as phenomenal as the entrees. If you choose to dine offsite, use the free shuttle service, which drops guests off anywhere within a two-mile radius of the resort.
Take the children with you. They’ll love the game room, Xbox Arcade, heated pools, and family-friendly activities, including beach bike rides and water sports. Camp Cheeca will keep them occupied while you spend time in the adults-only pool or indulge in the luxury Spa at the Cheeca Lodge.
While you’re here, take advantage of the other lush amenities: fish off the pier; play a game of pickleball, tennis, basketball, or shuffleboard; or try your hand at parity on the 9-hole golf course.
2. Islander Resort
It’s easy to see why so many guests fall in love with Islander Resort. Florida’s Best Resorts for Families, this lush location exudes natural beauty in the form of tall, verdant palms and 24 pristine acres, including a white-sand beach.
Kids will love jumping into the two heated saltwater pools and running around the on-site kiddy pool. Then, head to the beach for snorkeling, kayaking, paddle boarding, fishing, or bodysurfing – endless possibilities. Free bike rentals, basketball, volleyball, ping-pong, and shuffleboard are also available for land-based fun.
When hunger strikes, you’ll find something to tempt your palate at the property’s two restaurants: Beachside Tide and Elements Lounge & Restaurant. Insider tip: Visit Tides on a weekend afternoon for shows or a Thursday at dusk for family movie night.
If you’re looking for extra space, choose a specialty suite; it includes a kitchen, which makes it easier to feed toddlers.
3. Postcard Inn Beach Resort & Marina
Are you looking for a relaxing Florida getaway in an Instagram-worthy setting? You will find it at the Postcard Inn Beach Resort & Marina. The picturesque beach is where guests spend most of their time reclining on comfortable lounge chairs on the soft golden sand, which rises only to cool off in the emerald waves offshore or to take a dip in one of two crystal clear pools.
The daily resort fee includes beach chairs and towels, bike rentals, kayaks and paddleboards, snorkeling gear, and a shuttle within a four-mile radius of the complex. As for food, visitors can enjoy freshly brewed coffee at Starbucks coffee shops or a meal at one of four on-site restaurants.
When it comes to your nighttime retreat, choose from the many immaculate island-themed rooms or rent a cottage for a more exclusive and spacious escape.
Guests also have access to restaurants and amenities at the resort’s sister properties: La Siesta Resort & Marina, Amara Cay Resort, and the Pelican Cove Resort & Marina. Bring your favorite family members to join the fun – four-legged pals included.
4. Amara Cay Resort
The gorgeous Amara Cay Resort is also home to a pristine private beach, and boy, is it a beauty! Picturesque hammocks dot the sandy shore, suspended from swaying palm trees that offer shade from the scorching Florida sun. Relax in a thatched-roof hut, or take a dip in the zero-entry pool.
Relax in a swing chair or gather around a campfire in the evening to soak up the ambiance of this luxury resort carefree. Boutique Island Trendz makes it easy to shop for everything from beachwear to souvenirs.
Resort fees include water sports rentals such as kayaks and SUPs, beach chairs, towels, lawn games, bicycles, access to the fitness center, and a free shuttle to places within six kilometers of the hotel.
Unwind in a large room offering a relaxing blend of modern and tropical-themed luxury, with a furnished balcony. Grab breakfast at Dining Room or Reelburger or snack for lunch or dinner at Bar Tiki for poolside respite. Insider Tip: Dinner is served on Reelburger on Fridays and Saturdays.
5. La Siesta Resort & Marina
La Siesta Resort & Marina is home to a pristine private beach and a gorgeous heated oceanfront pool. The accommodations include spacious rooms, multi-bedroom suites, private chalets, and vacation homes with beach access and breathtaking views.
The daily resort fee includes breakfast, shuttle service, and fishing gear. Rental of bikes, kayaks, pedal boats and paddle boards are also free. As a bonus, guests can use amenities at La Siesta Postcard Inn’s sister resorts, Pelican Cove and Amara Cay.
Wild & Lime is the resort’s poolside restaurant, offering light lunches and afternoon snacks just steps from the beach. Breakfast is served at the Visitor Center, and dinner can be at a restaurant at one of the sister properties or cooked in your cottage kitchen.
An easy four-minute walk takes guests to nearby Indian Key Historic State Park, and the Museum of Diving History is just under three miles from the resort.
6. Purple House
Casa Morada is located on a quiet side street in the Florida Keys and features beautiful all-suite boutiques in its two guest houses. This pet-friendly hotel in Islamorada features poolside service at lunch and cocktails at sunset, while its garden cave is the perfect spot for a relaxing massage. For a romantic excursion, hop on the two-hour sunset cruise before relaxing in your spacious suite with sweeping water views and a private island. The nightly rate includes a host of attractive perks, like complimentary breakfast, as well as complimentary use of kayaks, paddleboards, snorkel gear, and bikes. You can also join free yoga classes.
7. Pine and palm resort
Pines and Palms Resort is about relaxation, where you can bask in the sun from a hammock or relax by the pool with easy access to the open water. This superior Islamorada hotel has the perfect accommodations for families and large groups, with all rooms featuring full kitchens and waterfront cottages with one, two, and three-bedroom options. Take a dip in the heated freshwater pool or have a cocktail at the tiki bar just inches from the Atlantic, while travelers can also bring their boat to enjoy free dockage and use of the ramp.
8. Pelican Cove Resort and Marina
Pelican Cove Resort & Marina embodies the relaxed lifestyle of the Florida Keys, transporting guests to a tropical paradise. Step out onto your private balcony from one of the oceanfront rooms, where you can watch playful pelicans and pods of dolphins splash in the waters, then head out to the saltwater lagoon. Active travelers can sign up for water sports and fishing charters, while some of Islamorada’s top attractions, including shopping, museums, art galleries, and wildlife parks, are just a short walk away.
9. Sunset Inn
Sunset Inn is a completely revamped contemporary design with a hint of Florida flair and a nostalgic throwback to a simpler time. It’s a one-of-a-kind Islamorada resort, offering spacious, sunny rooms with island décor and modern amenities like Wi-Fi, mini-fridges, and flat-screen TVs. Relax on a luxurious lounger by the full-size, climate-controlled pool or hop on a borrowed beach cruiser, then enjoy a soothing in-room massage or take advantage of the outdoor BBQ grills and tables for chess Jenga and oversized ping pong table. The hotel is also within walking distance of popular shops and restaurants.
10. Fisher Inn Resort and Marina
Fisher Inn Resort and Marina is a new boutique resort in Islamorada. Discover vibrant rooms with kitchenettes and free Wi-Fi, or treat yourself to an oceanfront Seaside Villa. Amenities include standing-up paddle boards and kayaks, a private sandy boardwalk, a continental breakfast, and a heated pool with ocean views.
11. The Caribbean Resort
Guests at the aptly named The Caribbean Resort to stay in one of many adorable, upscale homes rich in Caribbean charm—we’re talking teak and mahogany furnishings and brightly colored fabrics. Furnished porches only add to the island atmosphere, while the outdoor grill, built-in kitchen, and washer-dryer will make you feel truly at home in this lovely paradise. The only thing you will wish for is more vacation time!
Whether guests rent by the day, week, or month, they will have full access to resort amenities. These include a fantastic swimming pool kept cool near the surrounding garden full of palm, pineapple, and banana trees. In addition, a hot tub helps ease chilly nights, while waterfalls soothe visitors into an overall sense of calm.
Activities like stand-up paddleboarding, kayaking, and biking are also free. While you’re there, why not borrow a fishing rod and try your luck on the 45ft jetty? In a big one.
12. Matecumbe Resort
Matecumbe Resort boasts a beautiful beachfront setting in Islamorada. Their newly remodeled units cater to couples, families, and groups and feature in-suite kitchens, sitting areas, and all essentials for a Florida Keys getaway. Along with 300 feet of stunning waterfront, you’ll have access to a sparkling outdoor pool, boat ramp, BBQ grills, and free use of kayaks and bikes.
13. The town of moorings
Located midway between Miami and Key West, The Moorings Village is a private beachfront resort in Islamorada. With a tropical landscape, the former coconut plantation boasts more than 800 palm trees, plus orchid-lined paths that lead to the crystal clear waters. The resort’s benefits include an 80-foot-long pool, kayaks, paddleboards, bikes, and a fitness center and tennis court. In addition, one- and three-bedroom luxury cottages have fully equipped kitchens, pillow-top mattresses, flat-screen TVs, and coffee machines. All the while, this ultra-luxurious and lovely vacation home is the best escape, with 6,000 square feet of space and a private swimming pool.
14. Top Resort
Topsider Resort is a popular hotel with a private beach in Islamorada, located along the shores of the Straits of Florida, between the Atlantic and the Gulf of Mexico. It features unique octagonal stilt houses and fabulous amenities, including a “T” shaped pier that stretches out into the bay. Take advantage of the heated pool, bubbling hot tub, and tennis and shuffleboard courts, while bikes and kayaks are also available for your use. Two-bedroom villas feature full kitchens, a washer/dryer, and enough space to accommodate up to six people.
