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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 391 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
1–6 Sept
4.99 out of 5 average rating, 112 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Home in Islamorada
Oceanfront Estate - Private Beach, Pool, & Dock
5 bedrooms, 7 beds, 4 bathrooms
1–8 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • Marina, dining & fun!
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds, 3.5 bathrooms
5–12 Sept
4.95 out of 5 average rating, 22 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Flat in Tavernier
Oceanfront Bliss • Wall-to-Wall Water Views + Pool
2 bedrooms, 3 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Townhouse in Key Largo
Good Vibes Only!!! 2 bedroom/2 bath townhouse
2 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 55 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
1–6 Sept
4.8 out of 5 average rating, 5 reviews
Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Apartment in Tavernier
Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
1 bedroom, 2 beds, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 250 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
1–7 Sept
4.97 out of 5 average rating, 34 reviews