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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 beds, 2 private bathrooms
29 Oct – 3 Nov
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4.98 out of 5 average rating, 62 reviews
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
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
15–22 Sept
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
14–21 Sept
5.0 out of 5 average rating, 23 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
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
Home in Islamorada
Islamorada Getaway Bayfront Home with Dock
3 bedrooms, 6 beds, 2 bathrooms
17–22 Dec
4.88 out of 5 average rating, 8 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
14–21 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
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
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
14–20 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
2 bedrooms, 2 king beds, 2.5 bathrooms
19–26 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 20 reviews
Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Boat in Islamorada
HOUSEBOAT 2BD, 1 BATH PRIVATE KEYS COTTAGE MULLET
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.83 out of 5 average rating, 220 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
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
14–19 Sept
Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds, 3 bathrooms
17–24 Sept
5.0 out of 5 average rating, 27 reviews