Directory of Islamorada Vacation Rentals
We encourage travelers to avoid online scams targeting those booking vacation home rentals. Legal, licensed vacation rentals available in the Florida Keys are listed on this website. Click here for helpful information on how to spot and avoid fraudulent offers and illegal vacation rentals.
Staying in a Keys vacation home or condo rental is a great way to experience off-the-beaten-path neighborhoods and communities in our island paradise.
We urge visitors to be considerate and respect their neighbors. Since vacation rentals are typically located in residential communities, municipal or county noise ordinances apply. The same serenity and environmental qualities that attract visitors to the Keys are the reasons why many choose to live here on a year-round or part-time basis.
- LITTLE BASIN VILLAS
- 84 Johnston Rd Islamorada FL 33036
- (305) 363-8999 E-mail Website
- Keys Coupon Available Watch our video Facebook
- Located in the trendy Art District of Islamorada at MM 81.8 bayside. Little Basin Villas offer waterfront vacation rentals featuring free Wi-Fi, swimming pool, washer/dryer, dock, beach access and tiki hut! You'll be sure to feel at peace in paradise!
- Book now!
- Marlin House at Tarpon Point
- Islamorada FL 33036
- (305) 664-5152 E-mail Website
- Watch our video
- A luxury 3 story oceanfront home with spectacular ocean views! Top of the line finishes only surpassed by the incredible views from this 4 bedroom, 4 bath home! Watch the Sunrise from the oceanfront balconies. Community: gated, pool, beach, & pier dock.
- Osprey Bay Villa
- 82754 Overseas Highway Islamorada FL 33036
- (305) 393-2995 E-mail Website
- Watch our video
- Osprey Bay Villa fared great in Irma. We're just refurbishing the landscaping. The pool, hot tub, sun-decks, dockage are all in tip-top shape. The sunsets are still Fabulous and the Fishing is Great!
- Book now!
- THE OSPREY NEST AT HOLIDAY HOUSE RESORT CONDOMINIUMS
- MM 82.3 Islamorada FL 33036
- E-mail Website
- A LITTLE CONCH VILLAGE - Private and secluded waterfront flat with spectacular view of Florida Bay. Sleeps 4. Free boat ramp & dockage, Weekly rental Saturday-Saturday. Book direct with owner.
- Book now!
- Coastal Vacation Rentals of the Florida Keys
- 81927 Overseas Hwy Islamorada FL 33036
- (305) 664-0077 E-mail Website
- Watch our video Facebook Instagram
- We understand what makes a vacation home right for our guests, and make it our business to find those of the highest standard that go above and beyond expectations. By providing the finest in vacation rentals we ensure our guest's vacation is a success!
- Book now!
- FLORIDA KEYS LUXURY VACATION RENTALS - Premier Vacation Rentals
- Islamorada FL 33036
- (877) FLA-KEYS E-mail Website
- Pet-Friendly
- Specializing in upscale waterfront homes and elite properties. We set the standard for quality of inventory, depth of experience, extraordinary local knowledge, island hospitality - and attentive, innovative, friendly service.
- Florida Keys Rental Store
- MM 82 Overseas Hwy (on Bayside) P.O. Box 353 Islamorada FL 33036
- (305) 664-5152 E-mail Website
- Let us Fulfill Your Perfect Vacation Wishes! Floridakeysrentalstore.com is dedicated to creating the perfect Keys getaway. Specializing in Florida Keys vacation rental homes and condos in Key Largo and Islamorada in the Upper Keys.
- FLORIDA KEYS VACATION RENTALS, INC.
- 85996 Overseas Hwy Islamorada FL 33036
- (800) 207-4160 E-mail Website
- Facebook Twitter
- Hundreds of homes, condos, townhomes & cottages located between Key Largo & Key West, most with waterfront locations. Preview them on our website & chat online or let our rental managers help you find your ideal vacation spot. Weekly & monthly rentals.
- Florida Rentals.com- Islamorada
- Islamorda FL 33036
- Website
- FloridaRentals.com offers a large assortment of Islamorda rentals. Take your next trip knowing you aren't paying a penny more than you have to by renting direct from the owner. Find the vacation rental you've been searching for!
- Book now!
- Freewheeler Vacations
- 85992 Overseas Highway Islamorada FL 33036
- (866) 664-2075 E-mail Website
- Watch our video Facebook Twitter Instagram
- Find Your Special Place in the Sun with Islamorada's largest & most established Vacation Rental Company. Let Freewheeler find you anything from a luxury estate to a quaint villa. Beaches, pools, dockage, cable, Wifi & more. Stay for a week to a season!
- ISLAND VILLA RENTAL PROPERTIES
- 81681 Overseas Hwy. Islamorada FL 33036
- (305) 664-3333 E-mail Website
- Keys Coupon Available Pet-Friendly Watch our video Facebook Twitter
- Private little cottages, luxury condo villas, prestigious oceanfront estates...we offer a "home away from home". Dock your yacht (or skiff) at the back door! Privately owned...all very special places...in the warm Florida Keys sun!
- KEYS GETAWAYS VACATION RENTALS, INC.
- Islamorada FL 33036
- (305) 852-8040 E-mail Website
- We offer The Florida Keys most desirable luxury vacation rental accommodations! Beautifully appointed & maintained as private residences. Completely move-in ready & located at the best getaway locations! Your Home Sweet Vacation Home, away from Home!
- KEYSCARIBBEAN ANGLER'S REEF RESORT VILLAS & MARINA
- 84977 Overseas Highway Islamorada FL 33036
- (305) 853-5000 E-mail Website
- Keys Coupon Available
- Located just west of the only living barrier reef in the continental U.S., is a fishing village-styled retreat dotted with 2 & 3 bedroom charming Villas with a pool and private sunning beach.
- Tarpon Oasis
- 236 Tarpon Street Islamorada FL 33070
- (561) 504-2640
- Vacation Properties in the Florida Keys
- 91495 Overseas Highway Tavernier FL 33070
- (888) 464-3133
- Keys Holiday Rentals, INC
- 83247 Overseas Highway Islamorada FL 33036
- (305) 664-8808
