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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 private bathroom
7–12 Sept
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4.95 out of 5 average rating, 105 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
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 reviews
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
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
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
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 141 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
8–13 Sept
4.8 out of 5 average rating, 5 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
8–15 Sept
New place to stay
Top guest favourite
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
5–10 Oct
4.98 out of 5 average rating, 61 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
Ocean view, seaside paradise with golf cart.
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 76 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
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
Serviced apartment in Islamorada
Proximity Ats its Best! 2 Units, Pool + Breakfast!
2 bedrooms, 4 double beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
2–9 Sept
New place to stay
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
11–16 Sept