LODGING

Luxury Hotels & Resorts

• Cheeca Lodge & Spa
  81801 Overseas Highway, Mile Marker 82 • Islamorada, FL 33036
  305-664-4651, 800-327-2888 (Reservations)
  Situated on 27 acres, this luxury oceanfront resort in the Florida Keys offers 199 guestrooms, suites and beach bungalows. All guest rooms feature fantastic views of the Atlantic Ocean or lagoon, Italian-marble baths, and plasma TVs. On-site amenities include a full-service 4,200 square foot spa, a nine-hole, Par 3 Jack Nicklaus golf course, swimming pools, a fully-equipped fitness studio, fishing pier, restaurants, and six tennis courts.  map

• Holiday Isle Beach Resort and Marina
  84001 Overseas Highway • Islamorada, FL 33036
  305-664-2321
  A four resort complex that offers 176 accommodations with your choice of hotel rooms, efficiencies, cottages, and suites available. The resort is nestled alongside the beautiful turquoise waters and white sandy beaches and guests can enjoy tropical pools, fine restaurants, night life entertainment, a variety of tropical shops, watersports, and a full service marina while staying here. Fishing, diving, and snorkeling opportunities are also available.  map

• Lookout Lodge Resort
  87770 Overseas Highway • Islamorada, FL 33036
  305-852-9915
  One and two bedroom suites with beach front sunset views are their specialty. Their resort offers private swimming & sunbathing areas, with its chickee huts, lounges, and lagoon. Swimmers, sunbathers, and kayakers will enjoy quiet pleasurable hours in the Florida island sun. more...  map

• Pelican Cove Resort
  84457 Old Overseas Highway • Islamorada, FL 33036
  305-664-4435
  Vacation in paradise amidst spectacular ocean views and secluded tropical island gardens while at this resort that offers tastefully furnished accommodations with your choice of hotel rooms, studio efficiencies, and oceanfront Jacuzzi suites available with all accommodations including spacious balconies overlooking the ocean. Guests can enjoy a private sandy beach, tennis courts, an oceanfront Jacuzzi, an outdoor freshwater pool, and a Cabana Club while staying here, as well as a continental breakfast each morning.  more...

Bed & Breakfast Guides and Directories

• BedandBreakfast.com
  is a leading directory of bed and breakfasts, inns, and boutique lodgings throughout Islamorada and neighboring Florida towns. Shop, compare, and book from their large selection of Islamorada B&B properties with many exclusive deals offered. Gift certificates are also available. BedandBreakfast.com has nearly 7,000 property listings throughout the United States with 50,000 reviews, 80,000 property photos, and interactive maps.

Condos & Vacation Rentals

• Islamorada, FL,Vacation Rentals By Owner on VRBO®
  Renting a private vacation home offers the affordability, exceptional value, and personal attention that you deserve. Most private vacation homes offer considerably more space than you will find in the typical hotel room often at a reduced cost. Now, families can vacation together and still have room to breathe. View their list of vacation rentals now...

• HomeAway Vacation Rentals in Islamorada, FL
  Forget ordinary hotel rooms! Finding the perfect vacation getaway in Islamorada, FL is easy on HomeAway.com. Choose from 75,000 homes, condos, guesthouses, cottages, and cabins worldwide, and inquire directly with property owners through the site. HomeAway.com vacation rentals offer a unique local experience, often less expensive and more spacious than hotel rooms.

• Rentalo.com
  saves you time! Click to inquire & compare offers from Vacation Rentals, Hotels, and Bed & Breakfasts in Islamorada, FL. Find the best deals on short term accommodations using this award-winning, traveler-tested website. Browse our extensive inventory offering leisure and business travelers a wide variety of lodging options; from a budget studio to a luxury villa on a private island, from a small boutique hotel or bed and breakfast to a 5 star resort. Find the perfect place to stay for every occasion including family vacations, romantic getaways, business trips, ski, beach or golf vacations.

• Islamorada, FL Vacation Rentals by AlwaysOnVacation.com
  Find the perfect vacation rental to match your budget without compromising on luxury and comfort. Search from a wide selection of vacation homes, villas, condos and other property types. Browse photos, rates, availability and book properties directly from owner in Islamorada and surrounding areas.

• Islamorada, FL, Vacation Rentals on Vacation Rentals.com
  Are you still making hotel reservations? At VacationRentals.com, customize your next vacation and take advantage of off-season discounts, last minute deals, and freebies! No matter what destination or property type or number of bedrooms you’re looking for, you can find an affordable vacation rental that will suit the needs of you and your fellow travelers. So, what are you waiting for? No matter how tight your budget, you can book your dream vacation on VacationRentals.com today!

• Imagine Rentals
  81167 OverSeas Highway • Islamorada, FL 33036
  PO BOX 9228
  305-396-9002
  Imagine Rentals is pleased to present the best selection of Florida Keys vacation rentals to all its guests. Private homes, including some of the most alluring and tropical settings, offer sultry island flare, luxurious style and absolute comfort.  more...  map

Motels/Hotels

• Islander Resort
  82101 Overseas Highway • Islamorada, FL 33036
  305-664-2031
  Escape reality on the 1100 foot coral sand beach. Whether you choose to lounge oceanfront, in one of two pools or at the Tiki bar you will find the Caribbean feel of a traditional beach resort and all of the offerings of a four star hotel. Enjoy high seas adventure in the Sportfishing Capital of the World, scuba dive on Americas only living coral reef, dine in fabulous restaurants, visit quaint shops and galleries. Islamorada is the convenient Caribbean Island and the Islander Resort gives you island charm with every modern convenience.   map

• Key Islamorada Days Inn & Suites
  82749 Overseas Highway • Islamorada, FL 33036
  305-664-3681
  Welcome to the Days Inn and Suites Key Islamorada - gateway to the tropical Florida Keys. A peaceful relaxing hotel with personal service, the 36-unit Islamorada-Days Inn offers large rooms and suites overlooking the Atlantic Ocean. Guest rooms also available courtyard and poolside. All guest rooms are comfortably furnished and amenities in the suites include kitchens and washer/dryers. For your convenience, small boat dockage, up to 20 feet, is available.   map

• Ocean Dawn Suites
  82885 Old Highway • Islamorada, FL 33036
  Located Behind the Islamorada Post Office
  305-664-4844
  Quaint, luxury oceanfront hotel with concierge service and a staff that makes you feel right at home. more...

• Pines And Palms Resort
  80401 Old Highway • Islamorada, FL 33036
  305-664-4343
  Cottages, suites and duplexes in a tropical setting on the Atlantic Ocean in Islamorada. Each one-bedroom unit comes with a king or queen bed, a fully equipped kitchen, living room with sofa bed and patio or balcony. Tastefully decorated with tropical style furniture. Two and three bedroom units also available. Reserved boat dockage, ramp and trailer storage for boats up to about 25 feet depending on draft.   map