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Search results; Over 1,000 homes in Islamorada

Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
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4.93 out of 5 average rating, 392 reviews
Featured hotel
Room in Key Largo
Cottage 1
2 queen beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Featured hotel
Room in Islamorada
One bedroom suite garden view two queen
3 queen beds, 1 bathroom
31 Oct – 5 Nov
Featured hotel
Room in Islamorada
Matacumbe courtyard view room king Lanai
1 king bed, 1 bathroom
13–18 Sept
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed, 1 bathroom
13–18 Sept
4.86 out of 5 average rating, 7 reviews
Featured hotel
Hotel in Islamorada
Deluxe ocean view two queen room
1 bedroom, 2 queen beds, 1 bathroom
21–26 Sept
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 Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds, 4.5 bathrooms
6–13 Sept
4.96 out of 5 average rating, 27 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
Guest favourite
Home in Tavernier
Two Authentic Conch Houses Private Beach on FL BAY
4 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.96 out of 5 average rating, 142 reviews
Featured hotel
Room in Islamorada
Studio suite garden view king
2 king beds, 1 bathroom
11–16 Nov
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 151 reviews
Top guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
12–19 Sept
4.97 out of 5 average rating, 219 reviews
Guest favourite
Cottage in Islamorada Tavernier
Luxury Floating Cottage • FL Keys Waterfront Stay
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds, 2.5 bathrooms
5–12 Sept
New place to stay
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
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