Islamorada Vacation Rentals

Islamorada Vacation Rentals By Owner

Live like an islander in the tropical paradise of Islamorada, Florida, with our selection of vacation rentals by owner. From waterfront escapes to charming cottages, discover a diverse collection and secure your ideal retreat, where the turquoise waters and laid-back atmosphere of Islamorada create the perfect setting for an unforgettable Florida Keys getaway. Find your holiday house below.

Gorgeous Updated Condo in Oceanfront Building

Islamorada Vacation Rentals
2/BR 2/BA SLEEPS 6

Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft

Islamorada Vacation Rentals
4/BR 5/BA SLEEPS 12

FINAL WEEK AVAILABLE FOR 2024 - Aug 24th - 31st - OCEANFRONT - PRIVATE 2 ACRE ESTATE | HEATED POOL

Islamorada Vacation Rentals
6/BR 6.5/BA SLEEPS 14

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

Islamorada Vacation Rentals
3/BR 2/BA SLEEPS 6

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

Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.

Islamorada Vacation Rentals
2/BR 2/BA SLEEPS 6

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Islamorada Vacation Rentals

Welcome to Islamorada, a tropical paradise in the Florida Keys. Whether you're looking for a long-term retreat or a monthly escape, our vacation rentals offer the perfect island experience. From houses with private pools to condos with waterfront access, you'll find the ideal accommodation for your stay. Discover the beauty of Islamorada and make memories that will last a lifetime. Bring your boat!

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