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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.8 out of 5 average rating, 91 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
17–22 Aug
New place to stay
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
17–22 Aug
4.93 out of 5 average rating, 388 reviews
Superhost
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds
25–30 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
15–22 Aug
4.97 out of 5 average rating, 218 reviews
Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds
24–29 Aug
4.9 out of 5 average rating, 274 reviews
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed
12–17 Aug
4.91 out of 5 average rating, 34 reviews
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed
10–15 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Apartment in Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
2 bedrooms, 2 beds
28 Aug – 2 Sept
4.86 out of 5 average rating, 269 reviews
Top guest favourite
Boat in Tavernier
Island Sanctuary Islamorada
2 bedrooms, 2 beds
10–15 Aug
4.92 out of 5 average rating, 401 reviews
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed
16–21 Aug
4.8 out of 5 average rating, 51 reviews
Apartment in Tavernier
Friends' Getaway 1BR w/ Ocean View, Pool & Beach
1 bedroom, 2 beds
23–28 Aug
Superhost
Tiny home in Key Largo
Key Largo Tiny House, Marina, Beach + Pool Access
2 bedrooms, 2 beds
31 Aug – 5 Sept
New place to stay
Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds
22–29 Aug
4.98 out of 5 average rating, 90 reviews
Home in Marathon
Marlin House | Waterfront Pool Home Near Marina
2 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 4 reviews
Featured hotel
Room in Islamorada
Matacumbe courtyard view room king Lanai
16–21 Aug
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
10–16 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Guest house in Key Largo
Romantic Bayside Guesthouse peaceful beach sunsets
1 bedroom, 1 queen bed
25–30 Aug
4.85 out of 5 average rating, 516 reviews