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739 places

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Includes all fees, before taxes
Cottage in Islamorada
Charming 2BR cottage w/ pool & great location!
2 min drive
Jun 19 – 24
$247 per night
Superhost
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
2 min drive
Jul 14 – 19
$300 per night
Superhost
Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
14 min drive
Aug 6 – 13
$169 per night, originally $199
Superhost
Cottage in Islamorada
Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 3
2 min drive
Jun 11 – 16
$375 per night
Superhost
Condo in Islamorada
Resort with Private Beach & Gorgeous Sunsets!
5 min drive
Jul 1 – 8
$424 per night
Superhost
Home in Islamorada
Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 5
2 min drive
Jun 13 – 19
$375 per night
Superhost
Bungalow in Islamorada
Dream in Paradise! King Master, Queen Guest, Pool
2 min drive
Aug 28 – Sep 3
$475 per night
Home in Islamorada
Waterfront, Location, Private, Dock, Pool, Charm.
6 min drive
Jul 31 – Aug 6
$730 per night
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
6 min drive
Jul 5 – 10
$200 per night
Superhost
Home in Islamorada
Islamorada Waterfront Escape
3 min drive
Jul 8 – 15
$344 per night
Home in Islamorada
Flakey's
5 min drive
Aug 12 – 19
$228 per night
Superhost
Villa in Islamorada
Turtle Nest Estate
4 min drive
Jul 14 – 21
$1,500 per night
Home in Islamorada
Paradise in Islamorada
6 min drive
Jun 18 – 23
$369 per night
Townhouse in Islamorada
"Relax and Unwind"
15 min drive
Jun 10 – 15
$299 per night
Apartment in Islamorada
Islamorada Bungalows Suite 1 Bottom Floor
3 min drive
Jun 11 – 18
$273 per night
Superhost
Apartment in Islamorada
Endless Bay Views, Sues Promise Islamorada FL
5 min drive
Aug 17 – 24
$229 per night
Home in Islamorada
Porter’s Corner
6 min drive
Jul 16 – 21
$355 per night
Superhost
Boat in Islamorada
HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD
14 min drive
Aug 7 – 12
$299 per night
Superhost