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Search results; Over 1,000 homes in Islamorada

Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds, 2.5 private bathrooms
5–12 Sept
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4.98 out of 5 average rating, 91 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
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
7–13 Sept
4.97 out of 5 average rating, 35 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds, 4 bathrooms
5–10 Oct
4.87 out of 5 average rating, 47 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
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
Featured hotel
Room in Islamorada
One bedroom standard view suite two queens
3 queen beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 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, 392 reviews
Top guest favourite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 bedroom, 1 king bed, 1 bathroom
27 Jun – 2 Jul
4.97 out of 5 average rating, 71 reviews
Top guest favourite
Home in Islamorada
OceanView 2/2.5 w Beach Pool & Marina Islamorada
2 bedrooms, 2 beds, 2.5 bathrooms
19–26 Sept
5.0 out of 5 average rating, 21 reviews
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 Key Largo
Oceanfront Key Largo Escape: Kayaks, Hot Tub, Pool
3 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
4.91 out of 5 average rating, 54 reviews
Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 beds & pool
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.95 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Islamorada
The HMH House
1 bedroom, 2 beds, 1 bathroom
10–15 Sept
4.97 out of 5 average rating, 58 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds, 3 bathrooms
16–21 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
6–13 Sept
5.0 out of 5 average rating, 15 reviews
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.84 out of 5 average rating, 122 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.86 out of 5 average rating, 271 reviews