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Search results; Over 1,000 homes in Islamorada

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
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Featured hotel
Room in Key Largo
Cottage 1
2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds, 4 bathrooms
13–18 Sept
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
9–14 Sept
4.93 out of 5 average rating, 392 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 9 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
Guest favourite
Townhouse in Key Largo
Good Vibes Only!!! 2 bedroom/2 bath townhouse
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 72 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
11–16 Sept
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
4.99 out of 5 average rating, 112 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
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
Home in Key Largo
El Encanto | Private pool & tropical tiki
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
8–14 Sept
4.97 out of 5 average rating, 35 reviews
Featured hotel
Room in Islamorada
Studio suite garden view two queen accessible
3 queen beds, 1 bathroom
10–15 Nov
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 142 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
12–19 Sept
4.97 out of 5 average rating, 219 reviews
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 7 reviews