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Search results; Over 1,000 homes in Islamorada

Guest favourite
Apartment in Islamorada
Just a Few Friends - Ocean View and Bring your Boa
2 bedrooms, 2 beds, 2.5 private bathrooms
22–29 Sept
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4.94 out of 5 average rating, 33 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
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
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
19–24 Sept
4.93 out of 5 average rating, 393 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
20–26 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
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
13–18 Sept
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Townhouse in Islamorada
Oceanfront Dock 3-Bed Home, Pool & Speakeasy Bar
3 bedrooms, 4 beds
13–19 Sept
5.0 out of 5 average rating, 17 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
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
26 Sept – 3 Oct
4.97 out of 5 average rating, 219 reviews
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds
13–20 Sept
New place to stay
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds
11–16 Oct
5.0 out of 5 average rating, 100 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds
26 Sept – 3 Oct
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
4 bedrooms, 4 beds
30 Oct – 4 Nov
4.87 out of 5 average rating, 47 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
3 bedrooms, 10 beds
14–19 Sept
4.87 out of 5 average rating, 181 reviews
Home in Islamorada
Bayview Isle Place
4 bedrooms, 5 beds
30 Jan – 4 Feb
Superhost
Apartment in Islamorada
Ocean View Luxury Condo + 30' Boat Slip & Lift
3 bedrooms, 3 king beds
16–21 Sept
Top guest favourite
Apartment in Tavernier
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
2 bedrooms, 1 sofa bed
29 Sept – 4 Oct
4.94 out of 5 average rating, 160 reviews