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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
10–15 Aug
,
4.93 out of 5 average rating, 387 reviews
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
17–22 Aug
New place to stay
Superhost
Home in Islamorada
Waterfront Condo | Heart of Islamorada | Boat Slip
3 bedrooms, 4 beds
13–20 Aug
New place to stay
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 bedrooms, 4 beds
15–22 Sept
5.0 out of 5 average rating, 54 reviews
Houseboat in Islamorada
“The Salty Suite” Islamorada House Boat
2 beds
24–29 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Townhouse in Islamorada
Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio
3 bedrooms, 4 beds
9–15 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 217 reviews
Home in Islamorada
Heart of Morada - Dock & Pool
3 bedrooms, 3 king beds
5–12 Aug
New place to stay
Featured hotel
Room in Key Largo
Waterfront suite 9
16–21 Aug
Superhost
Home in Marathon
Keys Marathon Oceanfront, 4BR, 3.5 Bath Pool Home.
4 bedrooms, 4 beds
29 Aug – 5 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Townhouse in Islamorada
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
3 bedrooms
9–15 Aug
4.97 out of 5 average rating, 34 reviews
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds
8–15 Aug
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
3 bedrooms, 3 beds
23–30 Aug
4.95 out of 5 average rating, 21 reviews
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 bedrooms, 2 beds
22–27 Aug
4.83 out of 5 average rating, 117 reviews
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
4 bedrooms, 4 king beds
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Home in Marathon
4BR Gulffront Dog Friendly | Pool | Dock | Deck
4 bedrooms, 4 beds
16–23 Aug
4.71 out of 5 average rating, 7 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
2 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 149 reviews
Guest favourite
Villa in Islamorada
Bayberry Key: FREE Boat Dockage Sep-Oct Only!
3 bedrooms, 3 beds
26 Sept – 3 Oct
5.0 out of 5 average rating, 7 reviews