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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
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4.78 out of 5 average rating, 172 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
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
19–26 Aug
New place to stay
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 5 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
20–25 Aug
4.93 out of 5 average rating, 391 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
21–28 Aug
New place to stay
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 5 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
28 Aug – 4 Sept
New place to stay
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
15–22 Sept
5.0 out of 5 average rating, 55 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
22–29 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 7 reviews
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, 26 reviews
Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
Guest favourite
Villa in Islamorada
Bayberry Key: FREE Boat Dockage Sep-Oct Only!
3 bedrooms, 3 beds, 3.5 bathrooms
26 Sept – 3 Oct
5.0 out of 5 average rating, 7 reviews
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
7 bedrooms, 7 king beds, 7 bathrooms
20–25 Aug
New place to stay
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds, 7.5 bathrooms
8–15 Sept
4.86 out of 5 average rating, 36 reviews
Cottage in Islamorada
The Flagler, Floating Villa, 2 Bedroom, Full Bath
2 bedrooms, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Marathon
Luxury Boating Paradise+Pool+Sailing Kayaks
4 bedrooms, 8 beds, 3 bathrooms
24–31 Oct
5.0 out of 5 average rating, 88 reviews