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Search results; Over 1,000 places

Home in Islamorada
Bayfront Home w/ Beach and Dock
On Sea Oats Beach
Aug 13 – 19
New place to stay
Superhost
Villa in Islamorada
Beachfront Villa |Kayak|Cinema|Fire Pit|Pool
9 beds
May 20 – 25
4.84 out of 5 average rating, 44 reviews
Guest favorite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
Apr 29 – May 4
4.95 out of 5 average rating, 40 reviews
Home in Islamorada
Masterpiece home-Fisherman's paradise dock beach
7 beds
Mar 1 – 6
5.0 out of 5 average rating, 3 reviews
Guest favorite
Cottage in Islamorada
Key Lime Cottage 2br 1ba w/pool
3 beds
May 11 – 16
4.97 out of 5 average rating, 65 reviews
Guest favorite
Bungalow in Islamorada
Dream in Paradise! King Master, Queen Guest, Pool
Kayak
Jun 15 – 20
4.97 out of 5 average rating, 29 reviews
Guest favorite
Condo in Islamorada
Luxury condo with boat slip overlooking the bay
3 beds
May 11 – 18
5.0 out of 5 average rating, 18 reviews
Superhost
Condo in Islamorada
Resort with Private Beach & Gorgeous Sunsets!
4 beds
Sep 21 – 26
4.71 out of 5 average rating, 93 reviews
Apartment in Islamorada
Endless Bay Views, Sues Promise Islamorada FL
1 queen bed
May 15 – 22
4.86 out of 5 average rating, 43 reviews
Home in Islamorada
Islamorada Beach Home directly ON the beach
5 beds
Apr 22 – 29
Guest favorite
Home in Islamorada
Tropical Getaway 3/3 with 100’ boat dock and pool
5 beds
Apr 19 – 26
4.96 out of 5 average rating, 55 reviews
Guest favorite
Condo in Islamorada
Just a Few Friends - Ocean View and Bring your Boa
2 beds
Apr 22 – 29
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Islamorada
Porter’s Corner
4 beds
May 15 – 20
4.98 out of 5 average rating, 140 reviews
Guest favorite
Home in Islamorada
Islamorada Waterfront Escape
5 beds
May 11 – 18
5.0 out of 5 average rating, 13 reviews
Superhost
Home in Islamorada
Peninsula Villa | Heated Pool | Sunset Point
7 beds
Apr 19 – 26
New place to stay
Home in Islamorada
2/1 house on canal .
4 beds
Apr 19 – 26
Home in Islamorada
75731 Overseas Highway License#: 24-0390
6 beds
Apr 19 – 26
4.75 out of 5 average rating, 12 reviews
Condo in Islamorada
180 Degrees of Ocean Views, Lagoon and Florida Bay
4 beds
May 11 – 18