Islamorada Area Vacation Rentals

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.


Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool

Islamorada Vacation Rentals
4/BR 5/BA SLEEPS 12

Amazing Sunset Views

Islamorada Area Vacation Rentals
2/BR 2/BA SLEEPS 4

FULLY BOOKED UNTIL AUG 2024 - OCEANFRONT - PRIVATE 2 ACRE ESTATE | HEATED POOL

Islamorada Vacation Rentals
6/BR 6.5/BA SLEEPS 14

Beautiful Islamorada Renovated Condo MM 76.5

Islamorada Vacation Rentals
1/BR 1/BA SLEEPS 5

Luxury High End Islamorada Private Sandy Beach Access Hammocks, Kayaks, & More!

Islamorada Vacation Rentals
3/BR 2/BA SLEEPS 6

4/3 Waterfront House, Private Beach & Boat Ramp, 100ft+ Dock - Monthly Stays Only

Islamorada Area Vacation Rentals
4/BR 3/BA SLEEPS 10

Waterfront 33 Family and Boat Friendly Home, Great Views - Monthly Stays Only

Lower Matecumbe Key Vacation Rentals
3/BR 3/BA SLEEPS 8

Direct Ocean Front Estate on 3.5 acres, HUGE salt pool & Hot tub, Private Basin 100s feet of Dockage

Islamorada Vacation Rentals
5/BR 5/BA SLEEPS 14

Gated Ocean front condo with protected boat dock. Immediate access.

Long Key Vacation Rentals
3/BR 2/BA SLEEPS 6

Waterfront Paradise with Free Dockage - Contact us to price your stay!!

Islamorada Area Vacation Rentals
1/BR 1/BA SLEEPS 2

Waterfront Paradise on Canal W/New Pool

Lower Matecumbe Key Vacation Rentals
3/BR 2/BA SLEEPS 10

Spacious Islamorada home on canal with dock- 4000 square feet 5 bed/4 bath - Tennis, Pool and More

Islamorada Area Vacation Rentals
5/BR 4/BA SLEEPS 12

Gorgeous Updated Condo in Oceanfront Building

Islamorada Vacation Rentals
2/BR 2/BA SLEEPS 6

Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.

Islamorada Vacation Rentals
2/BR 2/BA SLEEPS 6

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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.

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