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Search results; Over 1,000 homes in Islamorada

Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
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4.78 out of 5 average rating, 172 reviews
Home in Islamorada
Gated Home Dock, Heated Pool & 2 Pools | Pet-OK
3 bedrooms, 2 king beds
1–8 Aug
New place to stay
Superhost
Villa in Islamorada
Private Beach & Dock / Heated Pool / Dolphin Key
4 bedrooms, 4 king beds
3–9 Aug
New place to stay
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
Guest favourite
Home in Key Largo
Lakefront pool house, jacuzzi Beachfront
3 bedrooms, 6 beds
7–12 May
4.96 out of 5 average rating, 69 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
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
7 bedrooms, 7 king beds
17–22 Aug
New place to stay
Top guest favourite
Home in Islamorada
Flakey's
2 bedrooms, 3 beds
8–15 Aug
4.97 out of 5 average rating, 216 reviews
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
Townhouse in Islamorada
Fishing Getaway | Dock, Pool & Sunrise
3 bedrooms, 3 beds
7–14 Aug
5.0 out of 5 average rating, 9 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
Top guest favourite
Home in Islamorada
Seaside Sanctuary in Islamorada
4 bedrooms, 5 beds
7–14 Aug
4.96 out of 5 average rating, 27 reviews
Guest favourite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
2 bedrooms, 3 beds
20–25 Aug
4.96 out of 5 average rating, 75 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
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
Luxe
Home in Islamorada
Private Beach / Pickleball Court and Tiki Bar
6 bedrooms, 8 king beds
16–23 Aug
Featured hotel
Room in Key Largo
Cottage 6
2 queen beds
11–16 Aug
Superhost
Home in Islamorada
Mirage | Resort Amenities, 3BR, Near Sandbar, Pool
3 bedrooms, 4 beds
8–15 Aug
Houseboat in Buttonwood Sound
Premium Floating Bungalow by Stay Ombi
1 bedroom, 1 king bed
2–7 Aug
4.91 out of 5 average rating, 34 reviews