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Search results; Over 1,000 homes

Guest favourite
Houseboat in Islamorada Tavernier
Baycation Houseboat | Florida Keys Waterfront Stay
1 bedroom, 2 beds, 1 private bathroom
15–20 Jul
,
4.9 out of 5 average rating, 272 reviews
Serviced apartment in Islamorada
Islamorada Stay! Free Breakfast | Pool & Parking!
1-min walk
1–6 Aug
New place to stay
Hotel room in Islamorada
2 Ocean View Units | Islamorada | Free Breakfast
1-min walk
18–23 Jul
New place to stay
Luxe
Villa in Islamorada
4 Bedroom Oceanfront Accessible Villa – Capacity 8
10-min drive
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Hotel in Islamorada
Tropical Getaway | Free Breakfast & Parking | Pool
1-min walk
30 Jul – 4 Aug
New place to stay
Top guest favourite
Flat in Islamorada
Sunset Access + Boat Basin | Walkable Islamorada
10-min drive
24–29 Aug
4.97 out of 5 average rating, 95 reviews
Guest favourite
Home in Islamorada
Sleeps 8 | Sunset + Boat Basin | Islamorada
10-min drive
24–29 Aug
4.87 out of 5 average rating, 46 reviews
Guest favourite
Villa in Islamorada
Isla Honeydew-3 EnSuite Bedrooms,Pool, Dock
10-min drive
23–30 Aug
4.94 out of 5 average rating, 18 reviews
Guest favourite
Villa in Islamorada
Isla Kiwi: FREE Boat Dockage Sep-Oct Only!
10-min drive
4–11 Aug
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
10-min drive
15–22 Sept
5.0 out of 5 average rating, 52 reviews
Superhost
Home in Islamorada
Beachfront Estate - Two Villas / Heated Pools
20-min drive
25–30 Jul
New place to stay
Superhost
Home in Islamorada
Private beach / Heated Pool / volleyball / Orchid
10-min drive
15–20 Jul
New place to stay
Top guest favourite
Home in Key Largo
The charm
30-min drive
19–24 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Villa in Islamorada
The Nest Villa & Marina in the heart of Islamorada
10-min drive
19–24 Jul
4.88 out of 5 average rating, 17 reviews
Guest favourite
Home in Islamorada
The Villa by the Bay Pool/Boat Dock, Islamorada Fl
10-min drive
2–9 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Key Largo
Oceanside Retreat: 3BR, Pool & Kayaks
30-min drive
1–6 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Cottage in Islamorada
Charming 2BR cottage in prime keys location w/pool
10-min drive
22–27 Aug
4.96 out of 5 average rating, 147 reviews
Home in Key Largo
Villa Mangrove - Key Largo Waterfront Property
50-min drive
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Islamorada
Flakey's
10-min drive
8–15 Aug
4.97 out of 5 average rating, 215 reviews