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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
19–24 Sept
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4.93 out of 5 average rating, 393 reviews
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 8 reviews
Featured hotel
Room in Key Largo
Cottage 1
2 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Featured hotel
Room in Islamorada
Matacumbe courtyard view room king Lanai
1 king bed, 1 bathroom
13–18 Sept
Featured hotel
Hotel in Islamorada
Deluxe ocean view two queen room
1 bedroom, 2 queen beds, 1 bathroom
21–26 Sept
Featured hotel
Room in Islamorada
One bedroom suite garden view two queen
3 queen beds, 1 bathroom
31 Oct – 5 Nov
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
11–17 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
11–18 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
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
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
2 bedrooms, 2 king beds, 2.5 bathrooms
12–19 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
3 bedrooms, 3 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 31 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 Marathon
Deluxe king
1 king bed, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
11–18 Sept
5.0 out of 5 average rating, 3 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
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