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Halfway Between Miami and Key West is this Beautiful and Relaxing Retreat!

The Chesapeake Beach Resort in the Florida Keys is a tropical hideaway with a family-friendly vibe. More than 700 feet of oceanfront beach surround an expansive saltwater lagoon, the kind you've always pictured in a Florida Keys vacation. You'll also find two heated swimming pools and a waterfront whirlpool as well as tennis, an outdoor gym and plenty of water sports. Take out a dive boat or a back country charter fishing boat for a day full of sun, surf and Florida Keys adventure. Completing your experience is a 44-room, eight-suite hotel with 13 luxury villas. Guest rooms come with a full range of amenities including black-out drapes and sheers, a mini fridge, coffee maker, and a 37” HDTV. Plus you can enjoy continental breakfast each morning! Enjoy the finest amenities on this 6.5-acre sanctuary – it's the perfect destination for your Florida getaway.

Villas and Condos
Beach at Chesapeake Beach Resort. Amid swaying palms and ocean breezes lies one of the best stretches of beach in the Florida Keys! This 700-foot sunning beach – and all of the Keys – is yours for exploration and relaxation at Chesapeake Beach Resort. Spend hours playing in the sand, soaking up the sun or kayaking just off shore. The resort also has paddle boats and Hobie Cats available for guest use.
Outdoor pool at Chesapeake Beach Resort. Chesapeake Beach Resort brings vibrant tropical tranquility into your Florida Keys family vacation. Introduce your kids to the friendly surf, sun and sand of the Florida Keys! Play on the playground and enjoy spacious accommodations and access to bicycles, water bikes and either of two heated pools. Plus there are great family-friendly attractions nearby like Theater of the Sea!
Groups at Chesapeake Beach Resort. Groups at Chesapeake Beach Resort. Bring your team to the beautiful oceanfront Chesapeake Beach Resort. Here, you'll find 700 feet of stunning beach and incredible views of the waters, sure to inspire and refresh your whole group. Their professional staff can happily assist you in planning a meeting, seminar, or something completely different, plus arrange for accommodations, catering and more.
Reunions at Chesapeake Beach Resort. Known for their spacious guest rooms and villas, as well as exceptional dining and entertainment adjacent to the resort, it is no wonder Chesapeake Beach Resort has been a favorite family resort for 50 years. Plan your next reunion at this great destination, where your family can come and relax in one of their two heated pools, enjoy water sports, tennis, and shuffleboard court. Hit the water in your own boat or take a fishing charter to some of the best fishing areas in the entire world. There's fun for the whole family!
Groups at Chesapeake Beach Resort. Groups at Chesapeake Beach Resort. Let the staff at Chesapeake Beach Resort help you plan the perfect wedding. Say "I Do" on a beautiful beach surrounded by lush tropical gardens with the calming waves as a soundtrack. The resort has close relationships with a multitude of wedding resources from caterers to cake makers to wedding officials to help make your event as stress-free as possible. Whether you're planning an small, intimate ceremony, or a more extravagant celebration, Chesapeake Beach Resort will make your dream wedding a reality!
Dolphins at Chesapeake Beach Resort. Diving at Chesapeake Beach Resort. Snorkeling at Chesapeake Beach Resort. Experience 700 feet of beach shores when you stay at Chesapeake Beach Resort in the beautiful Florida Keys! Enjoy crystal clear blue water, white sand and palm trees. It's a whole new kind of nature when you stay at this tropical paradise!
Aerial view of Chesapeake Beach Resort. Whether you bring your own boat or hire an onsite deep water fishing or back country fishing charter, Chesapeake Beach Resort overlooks some of the best sport fishing in the entire world. Sport fishing is king in the Keys and you're bound to come away with a trophy. Bonefish, swordfish, shark and more are yours for the catching!
Sunset at Chesapeake Beach Resort. With 700 feet of beautiful beaches, incredible ocean views from the comfort of your private room, and a variety of activities right onsite, the Chesapeake Beach Resort is the perfect place to escape to with your sweetheart. Here, you can unwind together out on the sand, indulge in delicious meals just a short walk away, or discover the world underwater with diving trips with Key Dives. It's the unforgettable romantic vacation you've been looking for!
Guest room at Chesapeake Beach Resort. Guest room at Chesapeake Beach Resort. Savor the lavish surroundings at Chesapeake Beach Resort. Here, you can feel right at home in a spacious villa, relax on your private terrace or lounge in the tiki hut. The beautiful oceanfront setting lets you sink your toes in the sand or unwind in a swaying hammock. With two onsite pools, outdoor exercise equipment, a tennis court and much more, you're sure to discover a brand of Florida Keys luxury that's uniquely Chesapeake Beach Resort and uniquely yours.
Aerial view of Chesapeake Beach Resort. Head to Chesapeake Beach Resort and learn all about the Florida Keys! Find out what the area was used for in the early days. Check out one of the local marinas and learn a little bit about the maritime history. You'll be happy you learned a thing or two on your next vacation.
Exterior view of Chesapeake Beach Resort. After the excitement of your wedding, there's nothing more satisfying than a soothing retreat somewhere special. At Chesapeake Beach Resort, you and your new spouse will discover a beautiful Florida Keys vacation that's just what you need for fun and relaxation. Unwind on the soft sand beaches, or explore the waters on a thrilling diving trip!
Snorkeling at Chesapeake Beach Resort. Diving at Chesapeake Beach Resort. Snorkeling at Chesapeake Beach Resort. Dive into the crystal clear blue water at the Florida Keys during your Chesapeake Beach Resort Vacation! Ask the friendly staff about chartering a diving boat and instructor. Make sure you have all the proper equipment and licenses required and then experience something you'll never forget! Swim among the fishes during your next vacation.
Balcony view at Chesapeake Beach Resort. Escape winter and head to the Florida Keys for your next Christmas or Thanksgiving vacation! Rather than fighting the crowds at the mall, enjoy 700 miles of beach with a good book. Take a diving adventure instead or go for a fishing cruise to enjoy Labor or Memorial Day. No matter what the holiday, Chesapeake Beach Resort is the perfect destination.
Exterior view of Chesapeake Beach Resort. As part of the Florida Keys, Islamorada is the Sport Fishing Capital of the World. But if you're not into fishing, there are plenty of other things to do on the island. Of course, you can spend your days relaxing on the beautiful white sand beaches, or maybe catch an Adventure Boat Tour for some whale and dolphin watching. Plus there are three State Parks nearby!
Guest room at Chesapeake Beach Resort. At Chesapeake Beach Resort, 13 private villas offer all the amenities of home in a spectacular Florida Keys setting. Enjoy fully-equipped kitchens, lavish bath amenities, granite counters and new kitchen cabinets. Plus, with your own private terrace and beautiful ocean views, you're sure to have everything you need for a truly unforgettable vacation.
Open Dates
  • All Year
Property Size
  • 65 units
Nearby City
  • Islamorada
Nearby Water
  • Atlantic Ocean
  • Bicycles
  • Gift Shop
  • Swimming Pool
  • Flatscreen TV
  • Internet
  • Satellite TV
  • Wireless Internet
Food & Drink
  • Continental Breakfast
  • Ice Machine
  • Gourmet Dining
  • Air Conditioning
  • Coffee Maker
  • In Room Safe
  • Jacuzzi
  • Microwave
  • Refrigerator
  • Sundeck
  • Whirlpool
  • Arts and Crafts
  • Photography
  • Shopping
  • Shuffle Board
  • Sightseeing
  • Swimming
  • Tennis
  • Beach
  • Boat Docks
  • Canoeing
  • Fly Fishing
  • Outdoor Grill(s)
  • Kayaking
  • Marina
  • Picnic Table(s)
  • Play Ground
  • Sailing
  • Saltwater Fishing
  • Scuba Diving
  • Snorkeling
  • Free Parking
  • A/V Equipment
  • Catering
  • Fishing Guides
  • Fitness Programs
  • Room Service
  • Handicap Access
  • Children Welcome
  • Pet Friendly
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