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Search results; Over 1,000 homes in Islamorada

Guest favourite
Villa in Islamorada
Angler’s Reef home • Pool • Kayaks • Paddle boards
2 bedrooms, 4 beds, 2.5 private bathrooms
4–11 Sept
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4.92 out of 5 average rating, 24 reviews
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
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
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
4–9 Sept
4.96 out of 5 average rating, 27 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
3–10 Sept
New place to stay
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
4–11 Sept
5.0 out of 5 average rating, 23 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
Guest favourite
Townhouse in Key Largo
Good Vibes Only!!! 2 bedroom/2 bath townhouse
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 19 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
11–16 Sept
Guest favourite
Home in Islamorada
Waterfront / Ocean Access Canal / Kamp Key
3 bedrooms, 3 king beds, 3 bathrooms
23–28 Sept
5.0 out of 5 average rating, 7 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
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 Marathon
NEW!The Hideaway~Pool~Pickleball~Putt-Putt~Kayaks!
3 bedrooms, 4 beds, 2 bathrooms
5–12 Sept
4.92 out of 5 average rating, 84 reviews
Home in Islamorada
Oceanfront Estate - Private Beach, Pool, & Dock
5 bedrooms, 7 beds, 4 bathrooms
4–11 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Tavernier
Atlantic Serenity 2407 Ocean Pointe 2 BA 2 BR
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Key Largo
Your Keys Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Sept
4.9 out of 5 average rating, 464 reviews
Home in Tavernier
Mojito Breeze Getaway
4 bedrooms, 6 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews