Vacation Rentals (25)
Maison Matecumbe #306
Luxury vacation rental, private beach, secluded, gated, heated pool... more
Sea Gull Condos
The Sea Gull condos are a great home base for your Florida Keys vacation. Ocean views, pool, and close to everything in Islamorada.... more
Turtle Bay
Mile Marker 86 Venetian Shores. Private home featuring Three bedrooms and three baths. Anglers dream with a 100 ft. deep water DOCK and sparkling pool, Venetian Shores boat marina in front PLUS great views of the wide canal in back, creating water views throughout.... more
Maison Matecumbe Condominums
Units 301, 304, 309 located within Maison Matecumbe gated community. Mile Marker 81. 3 bedrooms, 3 baths, 2 stories sleeps 6, pool, sandy beach. New stainless steel appliances.... more
The Beach House
MM 81. Situated right on the Atlantic Ocean right on the old road in The Heart of Islamorada! A view of the water from most rooms, the Main house has 3 bed/3baths. Guest cottage has 1bd/1ba.... more
148 Anglers Reef
MM 85. Beautiful ocean and garden views from these island-style detached villas. Nestled amidst quaint streets and walking paths, their design takes inspiration from Native Conch and Key West themes. Swimming pool and deep water dockage make these an anglers' paradise and a family playground.... more
Mile Marker 88. Four bedroom/three baths. Sleeps 8. Ocean front estate, heated pool and deep water dockage. Exclusive Community. Vacation Rental License #VR-09-82.... more
Sunset Dream
Mile Marker 83. Five bedroom/four bath. Bayfront, pool and dockage.... more
Mile Marker 83. Four bedroom/four bath. Sleeps 8-10. Bay front, pool, dockage.... more
Green Turtle Beach
Ocean front estate located on 4 acres, five bedroom/five 1/2 baths. Sleeps 10. Sandy beach and heated pool with jacuzzi. 24 hour security.... more
Sea Ranch
Cottage 1: oceanfront, one bedroom/ one bath upstairs. One bedroom/one bath downstairs with separate entrance. Sleeps 4-6. Cottage 2: Two bedroom/one bath. Sleeps 4-8. Private beach, observing pier, wet bar, pool table & newly remodeled. #VR-09-132... more
Island Villa Office
Patti Stanley's Island Villa is your connection to finding inviting FL Keys vacation properties from Key Largo to Tavernier to Islamorada and beyond. We are dedicated to helping you find your perfect Islamorada vacation rental home, Tavernier canal front condo or Key Largo rental retreat for your family. Whether you're planning a vacation or destination wedding, we can help you find your ideal Florida Keys vacation rental.... more
FL Keys Rental at Anglers Reef Islamorada
A wonderful house in Islamorada in OceanFront gated community with swimming pool and private boat dock. ... more
Caloosa Cove Resort and Timeshares -
Caloosa Cove Resort and Marina is located on a tropical 10-acre estate caressed by the beautiful alluring waters of the Atlantic Ocean and offers 30 luxuriously furnished suites with private balconies, full-service marina, bait & tackle shop, boat rentals, tennis, heated swimming pool, white sandy beach, restaurant & lounge. more
Keys Condo Rental
Vacation rental. Two bedroom waterfront condo with two master bedrooms. Heated pool, hot tub, tennis courts, fitness center. Private deep water boat dock included in rental.... more
Freewheeler Vacations, Inc.
86.0 Bayside Freewheeler Vacations has been offering vacation rental homes and condos on the Upper Keys for more than 25 years. Our vacation properties, available for a week or longer, have all the amenities of home. Just bring your toothbrush & bathing suit!... more
The Last Resort, Islamorada
Historic Oceanfront home with overwhelming views of the Atlantic, large open verandahs, private sandy beach, 15 x 30 foot heated swimming pool. Quiet seclusion awaits you at this unique destination.... more
Futura Yacht Club Condo
2 Bayview Condos avaialble with dock, weekely rentals. Each units has 2 bedrooms with 2 baths.... more
Special Old Keys Apartment on Wooded Acre Estate
Private cozy apartment on gated acre estate offers the viewing of sunsets on a private beach adjoining a boat dock with a boat house. A perfect spot for relaxation, and enjoying the fun and beauty of the Florida Keys !!! ... more
Imagine Rentals
P.O. BOX 575 Islamorada FL 33036 305-396-9002 Website Imagine Rentals is about vacationing inspired! We are excited to tell you about who we are… ... more

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