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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
Serene Cozy Cottage in Islamorada with Heated Pool
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.8 out of 5 average rating, 91 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
Featured hotel
Room in Key Largo
Cottage queen bed
1 queen bed
7–12 Sept
4.86 out of 5 average rating, 7 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
5–12 Sept
4.97 out of 5 average rating, 219 reviews
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed
7–12 Sept
4.93 out of 5 average rating, 391 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
8–14 Sept
5.0 out of 5 average rating, 16 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
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
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
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
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, 98 reviews
Guest favourite
Home in Key Largo
Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
5 bedrooms, 9 beds
13–18 Sept
4.99 out of 5 average rating, 158 reviews
Top guest favourite
Townhouse in Islamorada
Closest Oceanfront Home - 3 Stories and Boat Dock
3 bedrooms, 7 beds
4–11 Sept
5.0 out of 5 average rating, 23 reviews
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds
4–11 Sept
New place to stay
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
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds
23–28 Nov
4.96 out of 5 average rating, 151 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
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