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Search results; Over 1,000 homes in Islamorada

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Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 private bathroom
16–21 Sept
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4.96 out of 5 average rating, 79 reviews
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Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
19–24 Sept
4.93 out of 5 average rating, 393 reviews
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Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds
24–29 Sept
4.96 out of 5 average rating, 142 reviews
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Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds
16–23 Sept
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Townhouse in Key Largo
Good Vibes Only!!! 2 bedroom/2 bath townhouse
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 72 reviews
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Top guest favourite
Flat in Tavernier
Keys Sunset Sanctuary
2 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Townhouse in Islamorada
Luxury Island Retreat • Speakeasy Lounge & Dock
3 bedrooms, 4 beds
16–22 Sept
5.0 out of 5 average rating, 17 reviews
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Top guest favourite
Home in Tavernier
Islamorada Reef Canal & Pool home off Tav Creek-
3 bedrooms, 3 beds
16–21 Sept
5.0 out of 5 average rating, 31 reviews
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Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds
16–23 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
2 bedrooms, 2 king beds
19–26 Sept
4.97 out of 5 average rating, 64 reviews
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Guest favourite
Flat in Tavernier
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
2 bedrooms, 3 beds
16–21 Sept
4.97 out of 5 average rating, 221 reviews
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Luxe
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Luxe
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
6–11 Oct
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Guest favourite
Townhouse in Key Largo
Sunrise Retreat: Ocean & Pool Views, Gym, PB Court
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.9 out of 5 average rating, 70 reviews
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Top guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds
16–21 Sept
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Home in Key Largo
Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
5 bedrooms, 9 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 159 reviews
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Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds
19–26 Sept
5.0 out of 5 average rating, 21 reviews
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Guest favourite
Flat in Tavernier
Oceanfront Bliss • Wall-to-Wall Water Views + Pool
2 bedrooms, 3 beds
18–23 Sept
5.0 out of 5 average rating, 43 reviews