Charity De Souza is a Florida native and travel enthusiast. Traveling to over 50 countries abroad and residing in 6, she has a passion for exploring new cultures. While Central Florida is where she calls home, her favorite travel memories include skydiving in Switzerland and watching the sunset in Morocco.
Read full bio
Islamorada is a tropical paradise and a top destination in the Florida Keys. Just 90 minutes south of Miami, this “Sporting Capital of the World” offers endless outdoor recreation both on and near the water. Go deep-sea fishing, snorkeling, swimming at a beautiful beach, and hand-feed tarpon at Robbie’s of Islamorada, then take advantage of nearby seafood restaurants serving tasty tarpon sandwiches and conch fritters. Make the most of your visit by booking a stay at one of these top Islamorada Hotels, which boast on-site perks such as outdoor pools, ocean-view rooms, and easy access to water activities.
One of the best resorts in the Florida Keys, Cheeca Lodge and Spa is a tropical paradise in the Florida Keys. In addition to multiple fine dining restaurants, it features adult and family pools, a Jack Nicklaus-designed 9-hole par 3 golf course, and a pampering spa. Settle in at one of the elegant rooms and suites, which feature ocean views, large open-air balconies, and private soaking tubs in upgraded rooms, then kick back with an island-inspired cocktail at the tiki bar. Fishing enthusiasts can charter a boat, while other activities include snorkeling, sea kayaking, bicycling, and scuba diving.
Enjoy incredible water views from Islander Resort, a popular family-friendly resort in the Florida Keys sitting on 24 tropical acres from ocean to bay. The oceanside rooms and suites overlook the island’s largest beachfront, while spacious villas accommodate families and large groups with their townhome-style living spaces. Dine on fresh seafood at one of the on-site restaurants or bask in the sunshine at one of the two saltwater pools. If you’ve got the kids in tow, they’ll love the splash pad, water sports from the dock, beach games, and bikes. This resort is also pet-friendly, featuring a gourmet dog menu and an on-site dog park.
Postcard Inn Beach Resort & Marina is a Florida Keys favorite and a popular hotel in Islamorada for beach lovers and boaters. Located just minutes from Key Largo and a short drive from Miami, this iconic oceanfront resort features beachfront rooms with breezy balconies with Atlantic Ocean views. For extra luxury, stay in an airy Beach Cottage with a roomy living area. Start your day with Starbucks, then make your way to the oceanfront Raw Bar for fresh seafood sandwiches and live entertainment and unwind with rum runners at the tiki bar. Date night dinners are perfect at the Italian-inspired Ciao Hound. Paddleboards are included with your resort fee.
Amara Cay Resort is one of the best beach hotels in Florida for a reason. Not only does it have a private beach, sparkling outdoor pool, courtyard, and tiki bar where the Gulf of Mexico meets the Atlantic Ocean, but its resort fee also includes a long list of perks. You’ll have access to high-speed Wi-Fi, unlimited use of beach chairs and pool towels, a shuttle within a four-mile radius, and complimentary use of bicycles, kayaks, paddleboards, and lawn games. Enjoy the hotel’s beautiful waterfront setting in an oceanfront room, then enjoy island favorites at the on-site restaurant Reelcatch.
Escape to paradise at La Siesta Resort & Marina, which is set on the historic Overseas Highway and is one of the best spots in the Florida Keys. You can relax in your spacious room or suite, or upgrade to a beachfront cottage for the ultimate privacy just steps from the ocean. Experience laid-back island life at its finest at this pet-friendly hotel, which offers continental breakfast daily and includes snorkel gear, kayaks, and bicycles. The poolside Wild & Lime restaurant is tucked under shady palm trees just steps from the beach and is a popular gathering spot for drinks, light lunches, and snacks.
Casa Morada is nestled off a quiet side road in the Florida Keys and features beautiful suite boutiques in its two guest houses. This pet-friendly hotel in Islamorada boasts poolside service at lunch and sunset cocktails, while its garden grotto is the perfect place to enjoy a soothing massage. For a romantic excursion, hop on the two-hour sunset cruise before relaxing in your spacious suite with panoramic views of the water and private island. The nightly rate includes a host of alluring perks, such as complimentary breakfast, as well as complimentary use of the kayaks, paddleboards, snorkeling gear, and bicycles. You can also join free yoga classes.
Pines and Palms Resort is all about relaxation, where you can bask in the sunshine from a hammock or kick back poolside with easy access to the open water. This top Islamorada hotel has the perfect accommodation for families and large groups, with all rooms featuring a full kitchen and oceanfront cottages featuring one, two, and three-bedroom options. Take a dip in the heated freshwater pool or grab a cocktail at the tiki bar just inches from the Atlantic, while travelers can also bring their boat to enjoy free dockage and ramp usage.
Pelican Cove Resort & Marina embodies the laid-back lifestyle of the Florida Keys, transporting its guests to a tropical slice of paradise. Step onto your private balcony of one of the oceanfront rooms, where you can spot playful pelicans and dolphin pods splashing in the waters, then make your way to the saltwater lagoon. Active travelers can sign up for water sports and fishing charters, while some of Islamorada’s top attractions, such as shops, museums, art galleries, and nature parks are just a short walk away.
Sunset Inn describes itself as a fully renovated contemporary design with a dash of Florida flair and a nostalgic throwback to a simpler time. It’s a one-of-a-kind Islamorada resort, offering spacious, sun-filled rooms with island decor and modern amenities such as Wi-Fi, mini-fridges, and flat-screen TVs. Relax on a plush sun lounger at the climate-controlled full-size pool or hop on a loaner beach cruiser, then enjoy a relaxing in-room massage or take advantage of the outdoor BBQ grills and oversized chess, Jenga, and ping pong tables. The hotel is also within walking distance of popular shops and restaurants.
Fisher Inn Resort and Marina is a brand new boutique resort in Islamorada. Discover vibrant rooms with convenient amenities such as kitchenettes and free Wi-Fi, or go all out with an oceanfront Seaside Villa just steps from the sea. While staying here, resort perks include the use of stand-up paddleboards and kayaks, access to a private sandy waterfront, continental breakfast, and a heated pool overlooking the ocean. The hotel has boat parking and a boat ramp, while fish cleaning stations and BBQ grills allow you to cook your catch fresh.
The Caribbean Resort has won the hearts of many Florida Keys travelers, boasting panoramic ocean views, Caribbean-style homes, a fishing pier, and a beach-entry pool. Resort activities are included in your nightly rates, such as kayaking, bicycling, and paddleboarding, while fishing rods are available if you want to try your luck off the 450-foot fishing pier. The hotel’s award-winning pool is a hit with all ages, featuring a cooler microclimate that creates a natural oasis surrounded by tropical pineapple, palm, and banana trees and features a waterfall and private sun decks.
Matecumbe Resort boasts a beautiful oceanfront setting in Islamorada. Its recently remodeled units cater to couples, families, and groups alike, featuring in-suite kitchens, seating area, and all the essentials you’ll need for a memorable Florida Keys getaway. Along with 300 feet of stunning beachfront, you’ll have access to a sparkling outdoor pool, boat ramp, BBQ grills, and free use of kayaks and bicycles. There’s also a volleyball court, shuffleboard, and a playground for the kids.
Set midway between Miami and Key West, The Moorings Village is a private beachfront resort in Islamorada. Featuring tropical landscaping, the former coconut plantation features over 800 palms in addition to orchid-lined pathways that lead to the crystal clear waters. On-site amenities include an 80-foot-long swimming pool, kayaks, paddleboards, and bikes, as well as a fitness room and tennis court. Luxury one and three-bedroom cottages include fully-equipped kitchens, pillow-top mattresses, flat-screen TVs, and coffee makers, while the ultra-luxe Blue Charlotte vacation home is the ultimate escape with 6,000-square feet of space and a private pool.
Nestled along the shores of the Florida Straits between the Atlantic and Gulf of Mexico, Topsider Resort is a popular hotel with a private beach in Islamorada. It features unique octagon stilt houses and fabulous amenities, including a “T” shaped pier stretching out into the bay. Take advantage of the heated swimming pool, bubbling Jacuzzi, and tennis and shuffleboard courts, while bicycles and kayaks are also available for use. Two-bedroom villas feature full kitchens, a washer/dryer, and enough room to accommodate up to six guests.
A quaint oceanfront hotel in Islamorada, the Sands of Islamorada is set in the heart of the Florida Keys. This pet-friendly hotel features an outdoor pool and hot tub, as well as lounge chairs and BBQ grills, while spacious suites overlook the ocean and feature wrap-around porches shaded by palm trees. Boating, swimming with dolphins, kayaking, deep-sea fishing, and snorkeling are just some of the activities you can add to your itinerary when staying here.