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Search results; Over 1,000 homes in Islamorada

Guest favourite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 bedrooms, 2 beds, 1 private bathroom
8–13 Sept
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4.95 out of 5 average rating, 105 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds
8–14 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
16–23 Sept
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds
18–25 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds
13–20 Sept
4.91 out of 5 average rating, 23 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
12–19 Sept
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
8–14 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Islamorada
TheSandbar: Partial Ocean view,Pool,Free Dockage
3 bedrooms, 5 beds
17–24 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 14 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds
8–13 Sept
4.96 out of 5 average rating, 151 reviews
Featured hotel
Room in Islamorada
One bedroom standard view suite two queens
3 queen beds
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds
18–23 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki
3 bedrooms, 4 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 22 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
11–16 Sept
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
Guest favourite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds
13–18 Sept
4.84 out of 5 average rating, 123 reviews
Top guest favourite
Apartment in Tavernier
Tequila Sunrise
2 bedrooms, 2 beds
10–15 Sept
4.99 out of 5 average rating, 112 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
9–14 Sept
4.93 out of 5 average rating, 392 reviews
Top guest favourite
Home in Marathon
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
4 bedrooms, 4 beds
3–10 Oct
5.0 out of 5 average rating, 5 reviews