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Search results; Over 1,000 homes in Islamorada

Guest favourite
Apartment in Islamorada
Just a Few Friends - Ocean View and Bring your Boa
2 bedrooms, 2 beds, 2.5 private bathrooms
23–30 Aug
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4.94 out of 5 average rating, 33 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
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds, 3 bathrooms
16–22 Aug
5.0 out of 5 average rating, 16 reviews
Superhost
Flat in Islamorada
Isla Santorini | Islamorada Waterfront Condo, Pool
2 bedrooms, 3 beds, 2.5 bathrooms
21–28 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, 87 reviews
Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds, 3 bathrooms
30 Jan – 4 Feb
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, 54 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
20–27 Aug
5.0 out of 5 average rating, 12 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, 15 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, 6 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
16–22 Aug
4.97 out of 5 average rating, 34 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
16–23 Aug
New place to stay
Guest favourite
Home in Marathon
Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront
5 bedrooms, 5 beds, 4 bathrooms
22–29 Aug
4.93 out of 5 average rating, 46 reviews
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds, 3.5 bathrooms
29 Aug – 5 Sept
5.0 out of 5 average rating, 12 reviews
Superhost
Villa in Islamorada
Sirens Cove - Game Room, Pool - Dock Access
3 bedrooms, 5 beds, 3 bathrooms
18–25 Aug
New place to stay
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.93 out of 5 average rating, 389 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
Superhost
Home in Marathon
*NEW* Reel Escape~Dock!~Lift!~Pet Friendly~Grill!
3 bedrooms, 3 beds, 2 bathrooms
22–29 Aug
New place to stay