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Search results; Over 1,000 places in Islamorada

Guest favorite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
2 beds
May 16 – 21
4.94 out of 5 average rating, 16 reviews
Guest favorite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
Apr 29 – May 4
4.95 out of 5 average rating, 40 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
Superhost
Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
On Sea Oats Beach
Jul 7 – 12
4.85 out of 5 average rating, 124 reviews
Guest favorite
Houseboat in Islamorada
Getaway to Blackbeard's Hideout
3 beds
May 14 – 19
4.93 out of 5 average rating, 15 reviews
Guest favorite
Boat in Islamorada
HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD
3 beds
May 5 – 10
4.9 out of 5 average rating, 167 reviews
Guest favorite
Cottage in Islamorada
FLOATING WATERFRONT 2 BD, 1 BATH COTTAGE MANATEE
3 beds
May 5 – 10
4.85 out of 5 average rating, 126 reviews
Guest favorite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
2 king beds
May 4 – 11
4.97 out of 5 average rating, 36 reviews
Superhost
Home in Islamorada
Tranquility Cove
3 beds
Jun 22 – 27
4.68 out of 5 average rating, 190 reviews
Home in Islamorada
Bayfront Home w/ Beach and Dock
4 beds
Apr 29 – May 5
New place to stay
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
Home in Islamorada
Angler's Reef Gem in Islamorada!
On a private beachKayak,
Jun 8 – 15
5.0 out of 5 average rating, 12 reviews
Superhost
Home in Islamorada
Turtles Nest Islamorada Getaway 28 day rental
On Sea Oats BeachKayak,
Jul 14 – 20
Superhost
Home in Islamorada
Anglers Reef Home with Peek-a-Boo Ocean Views
2 beds
Apr 27 – May 4
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Islamorada
3 Lux Ensuites Walk/Boat Island!
3 beds
May 4 – 11
4.94 out of 5 average rating, 16 reviews
Guest favorite
Home in Islamorada
Heart of Islamorada ~ Private Boat Slip
6 beds
Apr 28 – May 4
5.0 out of 5 average rating, 9 reviews
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
Home in Islamorada
Flakey's
3 beds
Aug 10 – 17
4.97 out of 5 average rating, 164 reviews