Directory of Islamorada Vacation Rentals
Book your Islamorada accommodations now!
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
- Facebook Instagram TripAdvisor
- This oceanfront resort on the sunrise side of Islamorada features cottages and homes. Enjoy amenities such as the poolside bar, daily breakfast and access to snorkel gear, bikes and kayaks. Resort guests also receive access to all four Islamorada Resorts.
- 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!
- Coastal Vacation Rentals of the Florida Keys
- 82889 Overseas Hwy Islamorada FL 33036
- (305) 664-0077 E-mail Website
- Watch our video Facebook Instagram
- Providing high quality, personalized service to accompany our array of homes. Weekly & monthly rentals, condos, villas, estates, corporate retreats, wedding parties, oceanfront, bayfront, our inventory is endless. Let us share our "Keys" with you!
- 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.
- 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
