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Search results; Over 1,000 homes in Islamorada

Guest favourite
Home in Islamorada
Islamorada Waterfront Escape
3 bedrooms, 5 beds, 3 private bathrooms
22–29 Aug
,
4.94 out of 5 average rating, 18 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
21–26 Aug
New place to stay
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
21–28 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
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
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
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
Superhost
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds, 3.5 bathrooms
5–12 Sept
5.0 out of 5 average rating, 4 reviews
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 Islamorada
4-Bedroom Coastal Retreat *Special Fall Rates*
4 bedrooms, 4.5 bathrooms
24–31 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Marathon
Paradise Villa: a luxury retreat
7 bedrooms, 8 beds, 7.5 bathrooms
8–15 Sept
4.81 out of 5 average rating, 37 reviews
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
7 bedrooms, 7 king beds, 7 bathrooms
21–26 Aug
New place to stay
Superhost
Home in Marathon
Mar de Cielo - Waterfront - Heated Pool - Dock
4 bedrooms, 9 beds, 3 bathrooms
21–28 Aug
New place to stay
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
Flat in Islamorada
Elevated Retreat | Sunset Access + Boat Basin
2 bedrooms, 2 king beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 61 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
23–30 Aug
New place to stay
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
Flat in Islamorada
Poolside 2 queen Apartment
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.8 out of 5 average rating, 51 reviews