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Search results; Over 1,000 places

Superhost
Home in Islamorada
Oceanfront, Private Beach, Pool, Dock
2 min walk
May 25 – Jun 1
Guest favorite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
2 min drive
May 31 – Jun 5
4.92 out of 5 average rating, 325 reviews
Guest favorite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
14 min walk
Jun 26 – Jul 1
4.94 out of 5 average rating, 16 reviews
Guest favorite
Apartment in Islamorada
Hidden Gem Islamorada | 2nd Floor
9 min walk
May 19 – 24
5.0 out of 5 average rating, 23 reviews
Guest favorite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
8 min drive
May 16 – 21
4.94 out of 5 average rating, 16 reviews
Superhost
Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
8 min drive
Jul 7 – 12
4.85 out of 5 average rating, 124 reviews
Guest favorite
Apartment in Islamorada
Hidden Gem Islamorada | 1st Floor
9 min walk
Aug 10 – 15
4.98 out of 5 average rating, 47 reviews
Guest favorite
Home in Islamorada
Flakey's
3 min drive
Aug 10 – 17
4.97 out of 5 average rating, 164 reviews
Home in Islamorada
Private Beach,Estate pool,kayaks,bikes~EV charger
4 min walk
Apr 20 – 27
5.0 out of 5 average rating, 3 reviews
Guest favorite
Boat in Islamorada
HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD
8 min drive
May 5 – 10
4.9 out of 5 average rating, 167 reviews
Apartment in Islamorada
Convenient Location! Free Parking, Onsite Pool
3 min walk
Apr 21 – 26
Guest favorite
Home in Islamorada
Waterfront Home w/private dock & Sunset views
2 min drive
May 3 – 9
5.0 out of 5 average rating, 21 reviews
Guest favorite
Home in Islamorada
3 Lux Ensuites Walk/Boat Island!
3 min drive
May 4 – 11
4.94 out of 5 average rating, 16 reviews
Guest favorite
Home in Islamorada
Heart of Islamorada ~ Private Boat Slip
2 min drive
Apr 28 – May 4
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Islamorada
Anglers Reef Home with Peek-a-Boo Ocean Views
5 min drive
Apr 27 – May 4
5.0 out of 5 average rating, 5 reviews
Guest favorite
Cottage in Islamorada
Key Lime Cottage 2br 1ba w/pool
10 min drive
May 11 – 16
4.97 out of 5 average rating, 65 reviews
Guest favorite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
10 min drive
Apr 29 – May 4
4.95 out of 5 average rating, 40 reviews
Guest favorite
Bungalow in Islamorada
Dream in Paradise! King Master, Queen Guest, Pool
10 min drive
Jun 15 – 20
4.97 out of 5 average rating, 29 reviews