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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 private bathroom
7–12 Sept
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4.93 out of 5 average rating, 391 reviews
Featured hotel
Room in Islamorada
One bedroom standard view suite two queens
3 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
5–12 Sept
4.96 out of 5 average rating, 27 reviews
Featured hotel
Room in Islamorada
One bedroom suite garden view two queen
3 queen beds, 1 bathroom
31 Oct – 5 Nov
Featured hotel
Hotel in Islamorada
Deluxe ocean view two queen room
1 bedroom, 2 queen beds, 1 bathroom
21–26 Sept
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
4–11 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 40 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
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
11–16 Sept
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
4–11 Sept
New place to stay
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.96 out of 5 average rating, 141 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
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
8–15 Sept
New place to stay
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 beds & pool
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 105 reviews
Featured hotel
Rooms in Marathon
Superior two bedroom suite
2 bedrooms, 1 bathroom
18–23 Sept
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 112 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews