Lodging In the Upper keys

Islamorada and the Upper Keys offers a variety of comfortable lodging options  in convenient locations. From small, moderate and luxurious waterfront resorts  to economy accommodations.  Whether for one night or multiple nights, for single anglers or large  groups, Islamorada resorts can fulfill your expectations.

Lodging in the Upper Keys

Luxury | Moderate | Economy

(Luxury)
Cheeca Lodge and Spa

305-664-4651
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81801 Overseas Highway · Islamorada, FL 33036
Just 90 minutes south of Miami and nestled on 27 acres of lush tropical gardens, Cheeca Lodge & Spa is world-renowned for its luxurious accommodations, world-class amenities and spectacular oceanfront setting. Cheeca's 214 spacious rooms and suites feature luxurious West Indies styled décor, marble baths, fine linens, plasma TVs and wireless DSL. The Spa at Cheeca offers soothing massage therapies, skincare, signature body treatments and a fitness center. Cheeca offers award-winning fine dining and casual fare in three restaurants, the Chart Room and an oceanfront Tiki Bar. Outdoor venues for weddings, meetings and special events are spectacular and the resort offers full service wedding planning and conference services departments along with 4,600 square feet of meeting space. Cheeca features a 1,100' palm-lined beach, a 525' wooden fishing pier, two swimming pools and a saltwater lagoon, Camp Cheeca for kids, tennis, 9-hole golf course and a full service watersports facility. www.cheeca.com

Hawks Cay Resort

305-743-7000 · 800-432-2242
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61 Hawks Cay Blvd. · Duck Key, Florida 33050
Luxury resort accommodations, premier boating facilities and endless activities on secluded Duck Key www.hawkscay.com

Moorings Village

305-664-4708
123 Beach Road · Islamorada, FL 33036
Situated in the heart of Islamorada; halfway between Miami and Key West, The Moorings is an 18-acre property harboring 18 cottages and homes on what was once a coconut plantation. Ranging from one to three bedrooms, each residence is self-sufficient with its own well equipped kitchen, television, telephone, and in most cases, a washer and dryer. A short walk from your doorstep lies 1,100 feet of crystalline white sand- one of the largest and most beautiful private beaches in The Florida Keys. From the beach you can experience the thrill of wind surfing or the serenity of kayaking across the aquamarine waters of the Atlantic. While watching these waters you may catch a glimpse of the elusive gray ghost, known as the Bonefish, tailing across the flats tempting you to cast a fly his way. Islamorada, known as "The Sportfishing Capital of the World", offers two distinctly different types of fishing. If it's the Bonefish or Tarpon you're after, the back country or Gulf is for you, whereas if you're looking for Sailfish, Marlin or perhaps Dolphin (Mahi-Mahi), deep sea fishing might be more your style. If you prefer to be in the water rather than on top of it, our area has some of the best diving and snorkeling in the Keys, offering everything from shallow or mid-range reefs to steep wall and numerous wrecks. If it's on-land activities you are looking for, you will find a tennis court. www.mooringsvillage.com

Chesapeake Beach Resort

305-664-4662 · 800-338-3395
83409 Overseas Highway · Islamorada, FL 33036
Islamorada's famous beach and fishing destination, Chesapeake Beach Resort, rests on 6.5 acres of oceanfront sands and gardens halfway between Miami and Key West, in the Florida Keys. Our property is now exquisitely remodeled to deliver state-of-the-art amenities and luxurious accommodations to our guests. We are proud to offer 37" HDTV, Stereo radio/CD/alarm with MP3 docking capabilities and wireless internet connection, along with new carpeting, furniture and remodeled bathrooms and kitchens including granite countertops and vanities; all to make your stay more enjoyable and relaxing. Known for our spacious guest rooms and villas, as well as exceptional dining and entertainment adjacent to the resort,( limited room service provided by Whale Harbor's Wahoo's, it is no wonder we have been a favorite fishing and family resort for 50 years. So come and relax in one of our two heated pools, enjoy our water sports, outdoor exercise equipment shaded by a Tiki Hut, tennis, and shuffleboard court or hit the water in your own boat or take a fishing charter to some of the best fishing areas in the entire world. www.chesapeake-resort.com

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(Moderate)
Coconut Cove Resort & Marina

305-664-0123
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84801 Overseas Highway · Islamorada, FL 33036
Florida Keys beach hotel resort with accommodations, marina, restaurant for first class Florida Keys weddings. Owner Paul Bates has created a one of a kind Old-Style Florida Keys Resort hotel with lodging and many up to the minute activities in the village of Islamorada, in the heart of the Florida Keys. www.coconutcove.net

Islander Resort, a Guy Harvey Outpost

305-664-2031 · 800-753-6002
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82100 Overseas Highway · Islamorada, FL 33036
Islander Resort, a Guy Harvey Outpost gives you the perfect resort accommodation options for spending a long weekend or spending a long winter. A beautiful oceanfront resort boasts a new conference center, a pristine private beach with complete water sports offerings, as well as, two oceanfront swimming pools, a hot tub, shuffleboard, volleyball and a lighted, 200-foot fishing pier with amazing views of local marine life and is the home of Guys Beachside Bar & Grill. Their self-catering bayside townhomes feature fully equipped gourmet kitchens, a gulf front pool, beach, picnic area and a 14-slip marina basin. All Islander accommodations offer full kitchens and complimentary wireless internet. They never charge resort fees. www.GuyHarveyOutpostIslamorada.com

KonTiki Resort

305-664-4702
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81200 Overseas Hwy · Islamorada, FL 33036
Bayside property has boat basin, pool. Efficiencies available, Moderate Pricing www.kontiki-resort.com

La Siesta Resort

305-664-2132 · 877-278-0369
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80241 Overseas Highway · Islamorada, FL 33036
Oceanfront resort with lovely grounds, fishing charter boats, watersports, wedding location available, moderate room rates.www.lasiestaresort.com

Lookout Lodge Resort

305-852-9915
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87770 Overseas Highway · Islamorada, FL 33036
Escape the daily grind and revel in the spacious suites and natural beauty found at Lookout Lodge Resort in the Florida Keys. Located at Mile Marker 88 in Islamorada, Lookout Lodge Resort invites you to relax and enjoy your stay at their waterfront hotel. As the State of Florida's first certified Green Lodging with a certified Clean Marina, Lookout Lodge allows you to enjoy waterfront views with minimal impact to the environment. Lookout Lodge Resort can provide the perfect venue and accommodations for beautiful sunset weddings, memorable family reunions or other group events. www.lookoutlodge.com

Mitchell's Islamorada Villas

305-301-3947
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82236 Overseas Highway · Islamorada, FL 33036
Vacation rental villa on the bay, free marina, sleeps four (king bed, queen sleeper sofa) canopied acre, clean, trailer parking and ramp, fully furnished, sheets, towels, complete kitchen. Located at the 82.2 mile marker Bayside. www.Keysvilla.com

Pines And Palms Resort

305-664-4343 - 800-624-0964
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80401 Old Highway · Islamorada, FL 33036
Oceanfront Cottages, Full Kitchens, Pool, Dockage, Boat Ramp, Kayak & Bike Rentals. www.pinesandpalms.com

The Islamorada Resort

305-664-0073
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80001 Overseas Hwy · Islamorada, Florida 33036
Luxury lodging. Tiki bar, Diving, Fishing, Watersports, Dockage, Boat ramp, restaurant on premises. www.theislamoradaresort.com

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(Economy)
Key Lantern Motel

305-664-4572
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82150 Overseas Highway · Islamorada, FL 33036
Central location with modest prices. Off season midweek special: Rooms starting at $45. 3-nite minimum for holidays. Right next door to the famous sunset celebration at the Lorelei Restaurant. The most practical handicap access room in Islamorada, complete with roll-in shower www.keylantern.com

Drop Anchor Resort & Marina

305-664-4863
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84959 Overseas Highway (mm 85 oceanside) · Islamorada, FL 33036
Newly remodeled rooms. Oceanfront property with marina. They do weddings! Drop Anchor was the winner of the 2009 Community Character Award in Islamorada. This resort was chosen for its beautifully landscaped grounds and its brightly colored Bahama style bungalows. Drop in the Drop Anchor! 
www.dropanchorresort.com

Sunset Inn

305-664-3454
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82200 Overseas Highway · Islamorada, FL 33036
A little bit of paradise at affordable rates. Restaurant,pool, standard and efficiency rooms. Off season rate starting at $55 per night are available Sunday through Thursday. www.sunsetinnkeys.com

 Ragged Edge Resort & Marina

305-852-5389 · 800-436-2023
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243 Treasure Harbor Rd · Islamorada, FL 33036
Oceanside resort has pier, dockage, and plenty of privacy! Observation tower, shuffleboard, free bike use, boat basin. www.ragged-edge.com

Get Directions

  • In most cases I'll be meeting you at one of these boat ramps:
  • The Lorelei, Islamorada
    Directions
  • John Pennycamp State Park, Key Largo
    Directions
  • Whitewater Bay Boat Ramp. Flamingo
    Directions

 

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