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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 private bathroom
12–19 Sept
,
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 389 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
20–25 Aug
New place to stay
Guest favourite
Houseboat in Marathon
b watervibe
1 bedroom, 1 small double bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 90 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
20–25 Aug
4.96 out of 5 average rating, 78 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
17–24 Aug
New place to stay
Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds, 2.5 bathrooms
22–29 Aug
4.98 out of 5 average rating, 90 reviews
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
4.97 out of 5 average rating, 96 reviews
Top guest favourite
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 74 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Place to stay in Duck Key
Conch Key Villas #1. Fun, fishing & great sunsets
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 48 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.8 out of 5 average rating, 51 reviews
Guest favourite
Apartment in Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
2 bedrooms, 2 beds, 2 bathrooms
28 Aug – 2 Sept
4.86 out of 5 average rating, 269 reviews
Home in Marathon
Marlin House | Waterfront Pool Home Near Marina
2 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Guest house in Key Largo
Romantic Bayside Guesthouse peaceful beach sunsets
1 bedroom, 1 queen bed, 1 bathroom
25–30 Aug
4.85 out of 5 average rating, 517 reviews
Superhost
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Tavernier
Key Largo! Tavernier! Welcome to Paradise!
1 bedroom, 1 king bed, 1 bathroom
31 Aug – 5 Sept
4.98 out of 5 average rating, 349 reviews
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.9 out of 5 average rating, 275 reviews