filters

Search results; Over 1,000 homes in Islamorada

Photo 1 of 29
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 private bathroom
16–21 Sept
,
4.96 out of 5 average rating, 79 reviews
Photo 1 of 25
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, 14 reviews
Photo 1 of 29
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
25 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Featured hotel
Hotel in Islamorada
One bedroom standard view suite two queens
1 bedroom, 3 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
17–24 Sept
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
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
Photo 1 of 21
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
26 Sept – 3 Oct
4.97 out of 5 average rating, 219 reviews
Photo 1 of 29
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
19–24 Sept
4.84 out of 5 average rating, 123 reviews
Photo 1 of 29
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Photo 1 of 29
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
20–25 Sept
4.97 out of 5 average rating, 35 reviews
Photo 1 of 29
Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
16–22 Sept
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Guest favourite
Apartment in Islamorada
5-Star Sandy Beach Sunsets & Pool in Best Location
4 bedrooms, 7 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 19 reviews
Photo 1 of 12
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
12–17 Oct
4.83 out of 5 average rating, 6 reviews
Photo 1 of 29
Top guest favourite
Home in Islamorada
4-Bedroom Heart of Islamorada *Last Minute Deals*
4 bedrooms, 5 beds, 4.5 bathrooms
6–11 Oct
5.0 out of 5 average rating, 12 reviews
Photo 1 of 29
Guest favourite
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 7 reviews
Photo 1 of 28
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 16 reviews
Photo 1 of 29
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
16–23 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 101 reviews
Photo 1 of 27
Home in Islamorada
Charming Beach House directly ON the beach
4 bedrooms, 6 beds, 3 bathrooms
1–8 Oct
5.0 out of 5 average rating, 6 reviews