Directory of Islamorada Vacation Rentals
We encourage travelers, in order to avoid potential hazards, or scams targeting those searching for and booking online vacation home rentals in the Florida Keys, to seek out legitimate, licensed vacation rentals, which are listed on this website. Click here for helpful information on how to spot and avoid fraudulent offers, as well as better understand the guidelines legal vacation rentals must follow.
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.




- 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!
- 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.




- LA SIESTA RESORT & MARINA
- 80241 Overseas Hwy Mile Marker 80.2 Oceanside Islamorada FL 33036
- (888) 313-6200 E-mail Website
- Watch our video Facebook Twitter Instagram TripAdvisor
- Enjoy all the comforts of home elevated at La Siesta, with full kitchens, living and dining areas, furnished patios and more in our oceanfront cottages and beach houses—plus resort amenities including a private beach, pool, water sports and bicycles.
- Book now!


- Osprey Bay Villa
- 82754 Overseas Highway Islamorada FL 33036
- (305) 393-2995 E-mail Website
- Watch our video
- Wonderful Bay front home in the heart of Islamorada for rent by the week or month, sleeps 10. Spectacular sunsets & incredible panoramic views of Florida Bay! Walk to restaurants & shopping. Enjoy private pool, hot tub, beach, dockage/boat basin & more!
- Book now!




- ANGLER HOUSE VILLA
- 80500 Overseas Hwy Islamorada FL 33036
- (305) 664-5247 E-mail Website
- Facebook Instagram
- For a truly relaxing Keys-style experience, come stay on one of our 3 floating Villas – custom 50’, 2 bedroom/2 bath houseboats with full kitchen and sun deck. Enjoy our pool, paddleboards, boat ramp, fishing, cocktails at the Canoe Club and so much more!
- Book now!




- FLORIDA KEYS BREWING CO. B&B
- 81611 Old Highway Islamorada FL 33036
- (305) 664-9722 E-mail Website
- Facebook Twitter Instagram
- Stay in the heart of the Keys in our island shabby chic 2 bed/1 bath apartment above Florida Keys Brewing Co. Taproom. Walk/bike to the best restaurants, bars, shops & fishing Islamorada has to offer. Affordable, family/pet friendly in the best location!
- Book now!




- FLORIDA KEYS VACATION RENTALS, INC.
- 85996 Overseas Hwy Islamorada FL 33036
- (800) 207-4160 (305) 664-4470 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!
- 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
- Tarpon Oasis
- 236 Tarpon Street Islamorada FL 33070
- (561) 504-2640