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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
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
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
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
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
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
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
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
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 Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds, 3.5 bathrooms
24–31 Oct
5.0 out of 5 average rating, 13 reviews
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
Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds, 2 bathrooms
15–20 Sept
4.99 out of 5 average rating, 68 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
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
24 Apr – 1 May
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
2 bedrooms, 2 beds, 2 bathrooms
3–8 Oct
4.97 out of 5 average rating, 99 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
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds, 3 bathrooms
5–12 Sept
5.0 out of 5 average rating, 23 reviews