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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 private bathroom
10–15 Sept
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4.96 out of 5 average rating, 151 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds, 3 bathrooms
10–16 Sept
5.0 out of 5 average rating, 17 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
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
10–17 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 9 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
10–15 Sept
5.0 out of 5 average rating, 20 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
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
Flat in Tavernier
When Paradise is Key: Tropical Oceanfront Condo
2 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.88 out of 5 average rating, 101 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
10–17 Sept
5.0 out of 5 average rating, 3 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
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Tavernier
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
2 bedrooms, 3 beds, 2 bathrooms
10–15 Sept
4.97 out of 5 average rating, 221 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
10–17 Sept
New place to stay
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
11–18 Sept
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
11–18 Sept
5.0 out of 5 average rating, 15 reviews
Flat in Key Largo
New Key Largo Kawama • 2 Kings •Marina •Pickleball
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
New place to stay