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Islamorada Area Vacation Rentals By Owner
Escape to the laid-back allure of the Islamorada area in the Florida Keys with our handpicked vacation rentals by owner. Choose from waterfront hideaways to tropical retreats, ensuring an unforgettable stay in this paradise between the Atlantic Ocean and the Gulf of Mexico. Start saving your favorites below.
Neighborhoods in Islamorada Area Vacation Rentals
Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft | 4 Bed + Den | 5 Bath | Dockage
Islamorada Vacation Rentals
Luxury High End Islamorada Private Sandy Beach Access Hammocks, Kayaks, & More!
Islamorada Vacation Rentals
Next availability May 24th 2025 -OCEANFRONT - 6 Bed/6.5 Bath PRIVATE 2 ACRE ESTATE | HEATED POOL | FISHING DOCK
Islamorada Vacation Rentals
4/3 Waterfront House, Private Beach & Boat Ramp, 100ft+ Dock - Monthly Stays Only
Islamorada Area Vacation Rentals
Waterfront Paradise with Free Dockage - Contact us to price your stay!!
Islamorada Area Vacation Rentals
Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.
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Islamorada Vacation Rentals
Gracing the Florida Keys, Islamorada welcomes you to a tropical haven where relaxation and adventure converge. Vacation rentals in Islamorada present a range of choices, from luxurious waterfront beach houses to cozy island bungalow retreats. Dive into the crystal-clear waters, embark on fishing excursions, or savor fresh seafood at local eateries. With its unique blend of island charm and natural beauty, Islamorada welcomes you to relax, fully immerse yourself in coastal living, and craft unforgettable moments at the heart of the Florida Keys.