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.

From/Per night^$2071

Next availability May 24th 2025 -OCEANFRONT - 6 Bed/6.5 Bath PRIVATE 2 ACRE ESTATE | HEATED POOL | FISHING DOCK

Islamorada Vacation Rentals

6/BR 6.5/BA SLEEPS 14

From/Per night^$1397

Islamorada - Oceanfront - Private 1 acre Estate | Heated Pool - 4000 sq.ft | 4 Bed + Den | 5 Bath | Dockage

Islamorada Vacation Rentals

4/BR 5/BA SLEEPS 12

From/Per night^$643

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

Islamorada Vacation Rentals

3/BR 2/BA SLEEPS 6

From/Per night^$300

Gorgeous waterfront home

Islamorada Vacation Rentals

3/BR 2.5/BA SLEEPS 8

From/Per night^$171

Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.

Islamorada Vacation Rentals

2/BR 2/BA SLEEPS 6

Looking for more? Search these Neighborhoods near Islamorada Vacation Rentals

Lower Matecumbe Key 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!

Florida Rentals by Owner

Islamorada Vacation Rentals