Vacation Rentals

Islamorada has many great rental homes available. From large waterfront homes with swimming pools to quaint bungalows, Islamorada has options for all budgets and family sizes.

Paradise Cove 2bed/2bath winter rental in Lower Matecombe available October 1st - May 31st

Email: vacationrentalsofthefloridakeys@gmail.com

Paradise Cove is a stunning 2bed/3bath condo with open water views in a quiet neighborhood. This townhouse has all the amenities for you to enjoy a Keys winter! Downstairs on the first floor, there is a gaming area with a ping pong table, foosball table, TV with bar, futon, bathroom, washer & dryer plus tons of storage for all your gear. Upstairs on the second level, is the main living space with the kitchen and living room. There is also one bedroom and one bathroom on this floor. And finally the master suite is located on the 3rd level with stunning open water views and its own private balcony. Outside there will be tons of lounge seating on the balconies as well as on the ground level. This space will allow you to enjoy the backyard and watch boats pass by. There is a private boat dock for your use that can hold up to a 28ft boat.Read More
Villa 110 Anglers Reef

Email: gr@atlasinvestmentgroupllc

2 Bed & 2.5 Bath Villa in Anglers Reef Islamorada.  Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: private beach and heated resort style pool in walking distance. Each Villa has its own back terrace with barbecue, front porch seating, balconies, kayaks, and bikes. This Villa is one of the biggest in the community with 1,552 Square Feet of Living Space. Beautiful cherry hardwood floors, fully equipped kitchen with stainless steel appliances and granite counter tops.  Sleeper Sofa in Living Room with full entertainment center, with cable tv and wireless internet.   Master bedroom has a king size bed and the guest room has 2 twin beds each room has its own full private bathroom. Each Villa has special accommodations for families such as: playpen, high chair, and security gate for stairs.  Extra fresh linens and bedding included. Laundry room also available inside Villa. Visit VRBO listing number 7096733 or call direct to avoid all those annoying fees.Read More
Island Villa

Email: rentals@islandvilla.com

Vacation Rentals, Destination Weddings, Film/Production Locations. For more than fifteen years, Island Villa Rentals with Patti Stanley charting its course has been the trusted source for Islamorada vacation rentals, Tavernier and Key Largo rentals and destination wedding properties. Whether you’re planning a vacation or destination wedding, we can help you find your ideal Florida Keys vacation rental. Island Villa is the name synonymous with idyllic Islamorada rentals, Key Largo rentals, destination wedding sites, luxury home building, and much more!Read More
Anglers Reef 102 Islamorada Times

Email: info@islamoradatimes.com

This lovely two bedroom two bathroom sleeps 6 oceanfront home is at Mile Marker 85 in exclusive Angler’s Reef – 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500′ of stunning private beach. Protected deep water marina with a deep channel out to the Atlantic. Brand new Ocean Kayak 12 foot Tandem available for your use. Launch kayak from the private beach and try your luck at Isalmorada’s famed bone fishing in the flats right out front. Brand new in 2008, this home is fully equipped. Tile showers, Stainless appliances, granite kitchen counters, 3 Flat Screen TVs, & more. Visit www.vrbo.com listing  number 4208345 for more information and to reserve or call us direct at 484-919-2133 to avoid all those annoying fees.Read More
Barefeet Vacation Rentals

Email: info@barefeetrentals.com

Barefeet Rentals specializes in Vacation Rental Homes in the Upper Florida Keys. Boaters, fishermen, scuba divers, sun worshipers and snowbirds…welcome to the fabulous Florida Keys…what’s your pleasure? Our Key Largo vacation rentals are situated just a short drive to Islamorada and surrounded by beachfront views of the azure waters of the Atlantic and the calm waters of the northern Gulf of Mexico, known locally as the Florida Bay. Barefeet Rentals offers Florida Keys vacation rentals to fit any budget. Private rental homes and condos – modest to magnificent. We even offer Key Largo vacation homes with docks.Read More
Anglers Reef 130 Tequila Sunrise

Email: info@islamoradatimes.com

Angler’s Reef is a private, gated residential community in the “Fishing Capital of the World” of Islamorada FL.  Our community consists of 52 private homes, as well as, a 36 slip marina on the Atlantic.  Our amenities consist of two beaches and a waterfront pool. This lovely two bedroom two bathroom sleeps 6 oceanfront home is located at Mile Marker 85.Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on the 500′ of stunning private beach. Protected deep water marina with a deep channel out to the Atlantic. Brand new Ocean Kayak 12 foot Tandem available for your use. Launch kayak from the private beach and try your luck at Isalmorada’s famed bone fishing in the flats right out front. Brand new in 2008, this home is fully equipped. Tile showers, Stainless appliances, granite kitchen counters, 3 Flat Screen TVs, & more. Visit www.vrbo.com listing number 3788659 for more information and to reserve or call us direct at 484-919-2133 to avoid all those annoying fees.Read More