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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
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
12–19 Sept
4.97 out of 5 average rating, 219 reviews
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
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, 16 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
7–13 Sept
4.97 out of 5 average rating, 35 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
Top guest favourite
Flat in Tavernier
Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
2 bedrooms, 3 beds
12–17 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
30 Sept – 5 Oct
4.96 out of 5 average rating, 79 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
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Guest favourite
Villa in Islamorada
Has canal ocean sbigdavechartersandtours.comm-1m
4 bedrooms, 10 beds
15–20 Sept
4.99 out of 5 average rating, 68 reviews
Superhost
Home in Key Largo
Casa Mar | Private beach, pool & kayaks
4 bedrooms, 5 beds
13–18 Sept
Top guest favourite
Home in Islamorada
Exceptional vaca in Angler's Reef Islamorada
2 bedrooms, 3 beds
12–19 Sept
5.0 out of 5 average rating, 28 reviews
Apartment in Tavernier
Coastal Retreat, Pool, Marina, Ocean View, FL Keys
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Townhouse in Islamorada
Bayside Townhome in Islamorada with Boat Slip
2 bedrooms, 4 beds
5–12 Sept
4.98 out of 5 average rating, 91 reviews
Guest favourite
Cottage in Key Largo
Kampground Paradise w/Kayaks, Heated Pool & Marina
2 bedrooms, 3 beds
20–25 Sept
4.96 out of 5 average rating, 78 reviews
Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed
21–26 Sept
4.94 out of 5 average rating, 158 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
24 Apr – 1 May
5.0 out of 5 average rating, 56 reviews
Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
2 bedrooms, 2 beds
14–19 Sept
4.89 out of 5 average rating, 18 reviews