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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.8 out of 5 average rating, 91 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
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
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.8 out of 5 average rating, 51 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 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
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
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
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 21 reviews
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
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
8–13 Sept
4.8 out of 5 average rating, 5 reviews
Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 18 reviews
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
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 78 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
Apartment in Tavernier
Condo in Tavernier
2 bedrooms, 3 beds, 2 bathrooms
12–17 Sept
4.96 out of 5 average rating, 53 reviews