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Search results; Over 1,000 homes in Islamorada

Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 private bathrooms
2–9 Sept
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4.92 out of 5 average rating, 24 reviews
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 141 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 391 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
4–11 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
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
1–6 Sept
New place to stay
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
Luxe
Home in Marathon
Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys
5 bedrooms, 5 bathrooms
1–8 Sept
5.0 out of 5 average rating, 3 reviews
Home in Islamorada
Anglers Reef oceanview home-marina, beach, & pool
2 bedrooms, 3 beds, 3 bathrooms
2–7 Sept
New place to stay
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
2–7 Sept
4.96 out of 5 average rating, 27 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
3 bedrooms, 10 beds, 3 bathrooms
1–6 Sept
4.87 out of 5 average rating, 181 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
2–9 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Apartment in Tavernier
Lux Suite Open Ocean Views- 2 Balconies+Pool & Bar
2 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.91 out of 5 average rating, 166 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 105 reviews
Top guest favourite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
2 bedrooms, 2 king beds, 2.5 bathrooms
5–12 Sept
4.97 out of 5 average rating, 64 reviews
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