filters

Search results; Over 1,000 homes in Islamorada

Photo 1 of 26
Top guest favourite
Apartment in Islamorada
Luxury condo with boat slip overlooking the bay
3 bedrooms, 3 beds, 2.5 private bathrooms
3–10 Oct
,
5.0 out of 5 average rating, 36 reviews
Photo 1 of 29
Top guest favourite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 394 reviews
Photo 1 of 19
Guest favourite
Home in Islamorada
Life On A Rock Luxury Home in Downtown Islamorada
2 bedrooms, 2 beds, 2 bathrooms
12–17 Oct
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 79 reviews
Photo 1 of 29
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds, 3 bathrooms
11–18 Dec
5.0 out of 5 average rating, 56 reviews
Photo 1 of 29
Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
2 bedrooms, 2 beds, 2 bathrooms
22–27 Oct
4.9 out of 5 average rating, 20 reviews
Photo 1 of 29
Superhost
Villa in Islamorada
The Lighthouse | Ocean + Pool Views, Gameroom
3 bedrooms, 5 beds, 4 bathrooms
1–8 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 21
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds, 1 bathroom
3–10 Oct
4.97 out of 5 average rating, 220 reviews
Photo 1 of 25
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
Photo 1 of 12
Guest favourite
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds, 1 bathroom
18–23 Oct
4.88 out of 5 average rating, 8 reviews
Photo 1 of 29
Guest favourite
Boat in Islamorada
HOUSEBOAT 2BD, 1 BATH PRIVATE KEYS COTTAGE MULLET
2 bedrooms, 3 beds, 1 bathroom
13–18 Oct
4.83 out of 5 average rating, 221 reviews
Photo 1 of 29
Luxe
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds, 4 bathrooms
6–11 Oct
Photo 1 of 29
Guest favourite
Home in Islamorada
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
2 bedrooms, 3 beds, 2.5 bathrooms
1–8 Oct
5.0 out of 5 average rating, 17 reviews
Photo 1 of 29
Top guest favourite
Home in Key Largo
El Encanto | Private pool & tropical tiki bar
3 bedrooms, 4 beds, 2 bathrooms
18–23 Oct
4.96 out of 5 average rating, 24 reviews
Photo 1 of 29
Top guest favourite
Home in Islamorada
Off The Charts-Waterfront Tiki Bar & Private Dock
3 bedrooms, 3 beds, 2 bathrooms
10–17 Oct
5.0 out of 5 average rating, 15 reviews
Photo 1 of 29
Superhost
Home in Islamorada
Private Beach | Heated Pool | Mahi Key
3 bedrooms, 3 king beds, 3 bathrooms
30 Oct – 6 Nov
4.92 out of 5 average rating, 12 reviews
Photo 1 of 29
Top guest favourite
Flat in Tavernier
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
2 bedrooms, 3 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 103 reviews
Photo 1 of 29
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms, 3 bathrooms
2–7 Oct
4.97 out of 5 average rating, 35 reviews
Photo 1 of 29
Superhost
Home in Marathon
NEW! Reel Escape - 4br/No Stairs/Dock/Kayaks/Bikes
4 bedrooms, 7 beds, 3 bathrooms
10–17 Oct
New place to stay