Known as America’s Caribbean, Key West and the Florida Keys offer a tropical paradise to visitors seeking a holiday filled with rest and relaxation interspersed with awesome water adventures. Here, the vibe is completely laid back and free-living is highly encouraged so much so that you do not really need to be doing anything in particular to have a great time!

However, there is so much to do and see around here, apart from enjoying lazy days by the beach and watching one glorious sunset after another. Each region of the Keys has its own personality and unique charm, giving you lots of individual experiences that will enrich your stay.

The best has got to be the water activities. The sparkling ocean surrounding the island offers generous opportunities for every possible water activity – above the water, on the water, or underwater!

Sportfishing is mighty popular here – some of the best in the world! Sailing is another great treat, along with scuba diving, snorkeling, dolphin encounter programs, and watersports activities like jet ski, kayak, paddleboard, and so much more.

But in case you tire of the water, there are lots to discover on land, too. Historic sites abound, plus nature trails, state parks, and rainforests. Everything is here!

Also, the food is great. It is largely Caribbean-inspired, and the local seafood is amazing. Of course, the legendary key lime pie must be mentioned, too! You can pretty much get it everywhere, and you can even go on an impossible task of finding the best one on the island!

Entertainment-wise, you cannot go wrong with Duval Street and Mallory Square. These places are bursting with life and color whether you come by during the day or night. Lots of tours are available, too. Simply put, it is truly difficult to become bored here. There are just too many good things happening around!

Make your stay a truly awesome one and select from any of the best accommodation in Key West and the rest of the Florida Keys below. You are sure to have a great time whichever you pick.

Best Hotels in Key West

Warm, laid-back and effortlessly relaxing, Key West is the southernmost city in the US It’s lovely tropical weather attracts tourists year-round and its sparkling waters keep them coming back for more.

The beaches and watersports activities keep you entertained every second of the day, while the lively nightlife and historic sites add an extra charm to this popular destination.

Food-wise, there is an abundance of fresh seafood and key limes. Lobster, shrimp and grits, and key lime pie are all must-tries that will challenge your adherence to your diet!

Meanwhile, accommodation options spoil you with oceanfront views, refreshing swimming pools, and endless opportunities for water activities – exactly what you came to Key West for. Below are the most recommended options for you:

Margaritaville Key West Resort & Marina

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Island time finds more meaning at Margaritaville Key West Resort & Marina. Here, the order of the day is to relax and fall into a slower pace of life. As it is located in the heart of the Old Town facing the pier, the rooms have magical views from the balcony where you can witness daily water activities or simply breathe the refreshing ocean breeze. Meanwhile, soothing massages are available from the spa while watersports activities like diving, snorkeling, kayaking, sailing, fishing, and diving are all waiting for you at the marina. There are three dining options on-site but you are never too far away from everything the Old Town offers should you prefer to venture out!

The Gates Hotel Key West

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The problem with The Gates Hotel Key West is it makes it difficult for you to leave! It has everything – plush accommodation, excellent facilities, good food, and even a Cuban cigar lounge and its own private-label selection of specialty rums and handcrafted cocktails served at the Cuban-style bar. Talk about getting spoiled! Life is a party here – as evidenced by the daily pool parties in front of its in-house food truck that offers tapas-style food. Rooms are modern yet rustic and eco-friendly too, featuring reclaimed whitewashed beams and pine platform beds. Leather chairs and hardwood floors create a stylish and classy look while deluxe amenities like Peshtemal bathrobes, Turkish towels, Key West Aloe bath amenities ensure your comfort.

Oceans Edge Key West Hotel & Marina

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Elegant, minimalistic, and laid-back, Oceans Edge Key West Hotel & Marina is the first full service, luxury hotel ever built on Stock Island. Sophisticated in every way, its plush rooms present 100% ocean views best enjoyed from the private balcony. Within the property are six amazing pools and a fully functioning marina, too. A slew of adventurous water activities are also available on-site like scuba diving, snorkel trips, jetpack adventures, sunset cruises, sportfishing, dolphin watching and parasailing. Meanwhile, the Yellowfin Bar and Grill serves American-Caribbean influenced cuisine. But there are many restaurants nearby, as well as popular area attractions, making the hotel an excellent base.

Ibis Bay Resort

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Ibis Bay Resort delights with its collection of coral stone beachside bungalows on the shores of a serene bay, lined with mangroves. The accommodation mixes contemporary elements with a period charm featuring Cuban artwork, bold colors, and modern amenities. Also, don’t miss the in-house restaurant, The Stoned Crab! It is an island gem, serving their daily catch from two fishing boats. This is as fresh as it can get! The best dish to have? The seasonal Florida delicacy – Stone Crab claws. It is delicious and very sustainable. Try the three-tiered hot seafood tower, too. It is two trays filled with a selection of almost every type of seafood on the menu! Meanwhile, if you want to sink your feet deeper into the heart of Key West, it will not be a problem as the excellent location of the resort makes everything accessible. Bay Beach takes a five-minute walk while Duval Street is reached in a 10-minute drive.

Note: Another option for your trip to Key West is the Galleon Resort timeshare. This timeshare resort is highly regarded for its beautiful views of the Gulf, central location in Old Town and 90-slip marina. It has a pool, private beach, tiki bar and more! You can book either a standard studio timeshare unit, or a one- or two-bedroom condo.

Best Hotels in Islamorada

Known for world-class sportfishing, Islamorada is located 90 minutes south of Miami. This island paradise in the Florida Keys is comprised of six islands that have a true village ambiance. It is laid back, relaxed, and surrounded by clear and clean water.

Fishing is the top activity here. Whatever kind you fancy, there is never a shortage of opportunities everywhere you look. You can sail on your own or go on a guided tour. All sorts of water activities are available, too. Snorkel, dive, swim with marine life or get an adrenaline rush from various water sports.

Obviously, seafood is king in this destination, too. After all, there is nowhere else you can get is as fresh! Pair it with a frozen tropical drink, and there is no mistaking you are on a fantastic holiday. Catch the best experience of Islamorada from the following accommodation:

Casa Thorn

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Eclectic rooms, unique atmosphere, kind service, friendly staff – the list of things to love about Casa Thorn just goes on and on. This bed and breakfast charms with elegant and quirky accommodation and its unique cozy home feel. Each room is spacious with indulgent beds and baths. The pool, sun terrace, and garden are lovely facilities, and the free breakfast is simply the best!

Cheeca Lodge & Spa

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Deliciously sun-drenched, Cheeca Lodge & Spa in Islamorada, Florida Keys, Florida is located on a 1000 ft palm-lined private beach, along with 27 acres of beautiful gardens. It features a 525-foot wooden fishing pier, the longest in the area, and it is also a haven for watersports and activities, particularly sports fishing. The resort has a deluxe spa, two heated swimming pools and one salt water lagoon, 9-hole par three golf course designed by Jack Nicklaus, and six lighted tennis courts. Three restaurants and bars are on-site, too. Meanwhile, the spacious rooms have an elegant yet cozy finish, adorned in a West Indies style design. Each offers beautiful views and are fitted with luxurious amenities.

Postcard Inn Beach Resort & Marina

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Postcard Inn Beach Resort & Marina is an oceanfront dream. It is just like having your own boathouse! The vibe is nautical with white beddings and the many shades of blue in the overall sleek design. It calls to mind an old-school American beach vacation, perfect for families trying to bond over a much-deserved holiday. The rooms are expansive with mesmerizing ocean views and close to the beach or pools. Also, all sorts of adventures can be experienced here with the many non-motorized water sports facilities. Try the floating trampoline, paddle boards, peddle boats, bicycles, or kayaks and have fun by the water all day long. Be sure to drop by the Holiday Isle Tiki Bar too – the original home of the rum runner cocktail invented here in 1972!

Best Hotels in Marathon

A most family-friendly destination in the Florida Keys, Marathon has something for everyone. The white-sand beach is always a treat. Alternatively, go sailing or swim with dolphins for a relaxed but enjoyable time.

But if you want more activity, take on the many water sports options like stand up paddling or kayaking. Underwater adventures are plenty, too. The sites for diving and snorkeling here are world-class quality!

But there are land activities to keep you busy, too. Explore the hardwood hammock and rainforest areas of Crane Point Hammock and wander along the entertaining and educational Museum of Natural History of The Florida Keys and the Children’s Museum.

Other attractions include the historical Pigeon Key and the longest segmental bridge in the world, the Seven Mile Bridge. These can all be explored easily from the best hotels in the area:

Tranquility Bay

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The beach alone in front of Tranquility Bay is enough to make you fall in love with this hotel. It is really beautiful! Additionally, its secluded, oceanfront location, combined with the tropical gardens and towering coconut palms, place you into quick holiday mode within minutes of your arrival. This sun-soaked paradise offers deluxe beach houses and guest rooms that ooze luxury and provide lots of space. Facilities include three swimming pools, mini-golf, swimming beach, water activities, and spa. There is a restaurant on-site that is popular for seafood and it also has a special child menu and gluten-free food options The bar is a popular hangout at sunset where you can drink tropical drinks after a long day in the sun.

The Reach, A Waldorf Astoria Resort

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The Caribbean flair of Key West is in full bloom at The Reach, A Waldorf Astoria Resort. Lavish and dedicated to pampering, guests enjoy a 450 ft private beach, two water-front pools, gourmet steakhouse, and an excellent location a mere block from Duval Street. The rooms are lovely, expansive, and decorated in Caribbean-style. The balconies overlook the ocean, town, or courtyard. Amenities include plush pillow top bedding, Italian tile floors, Internet access, and flat-screen TV with cable channels. In between relaxing in your luxurious retreat, go on water adventures and try snorkeling, diving, jet ski tours, or deep-sea fishing. At night, explore Duval Street. You are sure to experience the best of Key West from the awesome location of this boutique resort!

Coral Lagoon Resort and Marina

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Recognized as the best child-friendly hotel in the Florida Keys, Coral Lagoon Resort and Marina feature 25 homey Conch-style cottages that are spacious as it gets. Each is spread through six acres of tropical paradise. The accommodation in this waterfront hotel is super clean and have full kitchens, family-size dining tables, two bathrooms, balconies, and complete entertainment systems. There is a heated swimming pool, full-service marina, free parking, and Internet access. Popular attractions nearby include Captain Hooks Marina and Dive Center, Conch Air, Island Hoppers Aerial Adventures, Sombrero Beach, and Dolphin Research Center.

Best Hotels in Big Pine Key & the Lower Keys

Known as the Natural Keys, Big Pine Key & the Lower Keys are dedicated to the preservation and conservation of its abundant terrestrial and marine wildlife.

Here, the usual chaos of city life disappears and is replaced by a slower-paced and relaxing experience of nature. One of the most enjoyable is a nature tour from a kayak! It creates a memorable experience as you see birds in their natural habitat, as well as the other flora and fauna unique to this destination.

If you are into diving, you will particularly love Looe Key and its spectacular marine life. But if you want to have some land adventure, go camping or visit the National Key Deer Refuge and learn about the white-tail Key deer native to the area.

In between all the activity, luxuriate in any of these retreats and find the best of comfort and relaxation in town:

Little Palm Island Resort & Spa

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Romantic, secluded, and over-the-top high class, Little Palm Island Resort & Spa offers the ultimate in luxury accommodation in the Florida Keys. It is so exclusive it can only be reached by seaplane or boat. Upon arrival, the island captivates with its stunning landscape, wildlife, and buildings. Everywhere you look, there are tropical flowers, palm trees, and sandy beaches that inspire the most awesome vacation. The comfort and opulence of the air-conditioned thatched roof bungalow suites with custom-made beds, vaulted ceilings, and private decks are unparalleled, too. Each accommodation further delights with an outdoor shower, private hot tub, separate living room, and island-inspired furnishing. The in-house restaurant is nothing but elegant, and the spa is every bit delightful. Staying here is a one-of-a-kind experience that simply creates memories that last a lifetime.

Parmer’s Resort

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Located on the waterfront, Parmer’s Resort lets you experience the laid back lifestyle that made the Keys famous. Individually decorated rooms spread over five acres welcome you on arrival. You can select from cottages, suites, or guest rooms and find the comfort and privacy that you need. Amenities include a balcony, refrigerators, cable TV, bathtub or shower, and free Wi-Fi access. Some rooms look out to the water. There is a marina on-site, plus a garden and an outdoor pool with sun loungers and umbrellas. Popular attractions nearby include beaches of Bahia Honda State Park and diving at Looe Key Reef. There are plenty of opportunities for backcountry, reef, and deep water fishing, too.

Looe Key Reef Resort and Dive Center

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A haven for snorkeling and diving, Looe Key Reef Resort and Dive Center has been sharing the best of Looe Key National Marine Sanctuary since 1978. If you came to Key West for diving, there is no better place to be! The resort features a full-service dive center with excellent dive instruction and local dive trips. Sunset cruises and boat rentals are available, too. Moreover, there is an outdoor swimming pool on-site, as well as a casual restaurant and Tiki Bar popular for local seafood and burgers. Rooms are traditionally decorated and equipped with sitting areas, free Wi-Fi access, flat-screen TVs, mini-fridges, and microwaves.

Best Hotels in Key Largo

Key Largo is the first and largest section of the Keys. It is a diver’s haven and is home to the largest artificial reef in the world, the 510 ft USS Spiegel Grove.

Some of the best activities to do here are scuba diving, snorkeling, sportfishing, and dolphin encounter programs. The beaches, nature trails, and expansive parks are awesome, too.

But really, you can just stay in one of the accommodations below, watch the beautiful sunsets, and your holiday will still be nothing short of amazing.

Ocean Pointe Suites At Key Largo

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Overlooking the Atlantic, Ocean Pointe Suites At Key Largo is a bright, beachfront resort that offers all-suite properties interspersed on 60 acres of paradise. The suites are individually styled and feature separate living areas, private bathrooms, full kitchens, and pull-out sofas. The balconies overlook the ocean or mangroves, perfect for rest, especially during sunset. Meanwhile, a variety of water activities is available for you to enjoy. There is a beach, boardwalk, and a private marina. Fishing, diving, and sailing are all pleasurable pursuits should you wish to venture out. An outdoor heated pool is on-site, plus tennis facilities, a waterfront restaurant and bar, kayak and snorkel rentals, and grilling areas. You will never get bored around here!

Hilton Key Largo Resort

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The location alone of Hilton Key Largo Resort guarantees a spectacular holiday. It is bordered by the Florida Bay and the Gulf of Mexico. It enjoys a private beach and is set on 12.5 acres of tropical forest with lush landscaping and nature trails. Really, how can you not have a wonderful stay here? Calm and ease pervade in the accommodation with contemporary amenities custom-designed beds, mini-fridges, and whirlpool tubs. The private balconies open to stunning views and a cooked-to-order breakfast is available. On top of that, a Carribean-inspired restaurant is on-site, plus two outdoor swimming pools and a poolside bar, gym, and sauna, and spacious meeting space. This island resort hotel truly knows how to spoil guests!

Key Largo Bay Marriott Beach Resort

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Sportfishing, coral reef diving, and watersports activities take center stage in this wonderful waterfront beach resort hotel that is also near a coral reef state park. The property is expansive, set on a sandy beach and a total of 17 acres bayside. Further, West-Indies and Caribbean-inspired accommodation give you the best of comfort and luxury. Romantic and contemporary, the suites are equipped with flat-screen TVs with premium channels, mini-fridges, Wi-Fi, and balconies with beautiful waterfront views. As mentioned, plenty of water activities will keep you busy here. There is a full-service dive shop on-site, a large outdoor pool and poolside lounge, hot tub, luxe open-air day spa, gym, shuffleboard, and basketball court. Other facilities include a marina, seafood restaurant and Tiki bar with live music, and free parking.

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