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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 bed, 1 private bathroom
27 Jun – 2 Jul
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4.97 out of 5 average rating, 71 reviews
Featured hotel
Hotel in Key Largo
Diver den 1
1 bedroom, 1 queen bed, 1 bathroom
22–27 Sept
Featured hotel
Hotel in Key Largo
Cottage 2 queen beds
1 bedroom, 2 queen beds, 1 bathroom
16–21 Sept
5.0 out of 5 average rating, 3 reviews
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
Featured hotel
Hotel in Islamorada
Studio suite ocean front one king
1 bedroom, 2 king beds, 1 bathroom
7–12 Nov
Featured hotel
Hotel in Islamorada
One bedroom suite garden view two queen
1 bedroom, 3 queen beds, 1 bathroom
31 Oct – 5 Nov
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
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
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds, 3 bathrooms
15–21 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 23 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
15–22 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
23–28 Sept
4.95 out of 5 average rating, 105 reviews
Luxe
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
15–20 Sept
Guest favourite
Flat in Tavernier
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
2 bedrooms, 3 beds, 2 bathrooms
15–20 Sept
4.97 out of 5 average rating, 221 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
15–20 Sept
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Home in Key Largo
Ocean view, seaside paradise with golf cart.
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 77 reviews
Luxe
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews