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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
9–14 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
3–9 Aug
New place to stay
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
3 bedrooms, 6 beds
10–15 Aug
4.96 out of 5 average rating, 69 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, 15 reviews
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
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 216 reviews
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds
8–15 Aug
Guest favourite
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
7–14 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
7 bedrooms, 7 king beds
17–22 Aug
New place to stay
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
4 bedrooms, 5 beds
2–9 Aug
5.0 out of 5 average rating, 11 reviews
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
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
Guest favourite
Home in Tavernier
Luxury 3/2 Mini-golf, Hot Tub, Kayaks & Pedal boat
3 bedrooms, 5 beds
6–11 Aug
4.96 out of 5 average rating, 46 reviews
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
3 bedrooms, 1 sofa bed
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Townhouse in Key Largo
Sunrise Escape - Ocean Front Villa - Sleeps 10
3 bedrooms, 10 beds
11–16 Sept
4.87 out of 5 average rating, 178 reviews
Guest favourite
Villa in Islamorada
Isla Kiwi: FREE Boat Dockage Sep-Oct Only!
3 bedrooms, 3 beds
14–21 Aug
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
4 bedrooms, 5 beds
23–30 Aug
5.0 out of 5 average rating, 12 reviews
Home in Islamorada
Charming Beach House directly ON the beach
4 bedrooms, 6 beds
17–24 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Key Colony Beach
4/2.5 Waterfront home on Key Colony, Pool, Dockage
3 bedrooms, 4 beds
14–21 Aug
4.85 out of 5 average rating, 39 reviews