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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 private bathroom
8–13 Sept
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4.95 out of 5 average rating, 105 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
9–14 Sept
4.93 out of 5 average rating, 392 reviews
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
24–29 Sept
4.96 out of 5 average rating, 142 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
8–14 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Key Largo
Las Olas
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
8–15 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 20 reviews
Superhost
Home in Key Largo
Exclusive! 16 Guest Twin Villas at Mariners Club
6 bedrooms, 12 beds, 8 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
11–16 Sept
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
9–16 Sept
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds, 3.5 bathrooms
8–15 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
2 bedrooms, 2 king beds, 2.5 bathrooms
12–19 Sept
4.97 out of 5 average rating, 64 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
8–15 Sept
New place to stay
Guest favourite
Home in Marathon
NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!
3 bedrooms, 4 beds, 2 bathrooms
12–19 Sept
4.92 out of 5 average rating, 84 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
3 bedrooms, 10 beds, 3 bathrooms
14–19 Sept
4.87 out of 5 average rating, 181 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds, 4.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
4.96 out of 5 average rating, 48 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Home in Islamorada
Oceanfront Estate - Private Beach, Pool, & Dock
5 bedrooms, 7 beds, 4 bathrooms
9–16 Sept
5.0 out of 5 average rating, 4 reviews