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The Islands of Islamorada
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Search results; Over 1,000 places
Over 1,000 places
Superhost
Superhost
Home in Islamorada
Oceanfront, Private Beach, Pool, Dock
2 min walk
2 min walk
May 25 – Jun 1
May 25 – Jun 1
$1,079
night
$1,079 per night
Guest favorite
Guest favorite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
2 min drive
2 min drive
May 6 – 11
May 6 – 11
$200
$180
night
$180 per night, originally $200
4.92 out of 5 average rating, 325 reviews
4.92 (325)
Guest favorite
Guest favorite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
14 min walk
14 min walk
Jun 26 – Jul 1
Jun 26 – Jul 1
$200
night
$200 per night
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Guest favorite
Guest favorite
Apartment in Islamorada
Hidden Gem Islamorada | 2nd Floor
9 min walk
9 min walk
May 19 – 24
May 19 – 24
$308
night
$308 per night
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Guest favorite
Guest favorite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
8 min drive
8 min drive
Jun 2 – 7
Jun 2 – 7
$299
$189
night
$189 per night, originally $299
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Guest favorite
Guest favorite
Apartment in Islamorada
Hidden Gem Islamorada | 1st Floor
9 min walk
9 min walk
Aug 10 – 15
Aug 10 – 15
$308
night
$308 per night
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Guest favorite
Guest favorite
Home in Islamorada
Flakey's
3 min drive
3 min drive
Aug 10 – 17
Aug 10 – 17
$228
night
$228 per night
4.97 out of 5 average rating, 164 reviews
4.97 (164)
Home in Islamorada
The Russell Estate, 2 Acrs on OCEAN, tropical 3/2
11 min walk
11 min walk
Apr 20 – 27
Apr 20 – 27
$745
night
$745 per night
4.97 out of 5 average rating, 29 reviews
4.97 (29)
Guest favorite
Guest favorite
Home in Islamorada
3 Lux Ensuites Walk/Boat Island!
3 min drive
3 min drive
May 4 – 11
May 4 – 11
$500
$450
night
$450 per night, originally $500
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Guest favorite
Guest favorite
Cottage in Islamorada
Key Lime Cottage 2br 1ba w/pool
10 min drive
10 min drive
May 11 – 16
May 11 – 16
$264
night
$264 per night
4.97 out of 5 average rating, 65 reviews
4.97 (65)
Home in Islamorada
Private Beach,Estate pool,kayaks,bikes~EV charger
4 min walk
4 min walk
Apr 20 – 27
Apr 20 – 27
$1,369
night
$1,369 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Islamorada
Waterfront Home w/private dock & Sunset views
2 min drive
2 min drive
May 3 – 9
May 3 – 9
$1,092
night
$1,092 per night
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Superhost
Superhost
Home in Islamorada
Anglers Reef Home with Peek-a-Boo Ocean Views
5 min drive
5 min drive
Apr 27 – May 4
Apr 27 – May 4
$379
night
$379 per night
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favorite
Guest favorite
Home in Islamorada
Angler's Reef Gem in Islamorada!
5 min drive
5 min drive
Jun 8 – 15
Jun 8 – 15
$375
night
$375 per night
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Guest favorite
Guest favorite
Home in Islamorada
Heart of Islamorada ~ Private Boat Slip
2 min drive
2 min drive
Apr 28 – May 4
Apr 28 – May 4
$840
$543
night
$543 per night, originally $840
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favorite
Guest favorite
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
10 min drive
10 min drive
Apr 29 – May 4
Apr 29 – May 4
$395
$325
night
$325 per night, originally $395
4.95 out of 5 average rating, 40 reviews
4.95 (40)
Guest favorite
Guest favorite
Home in Islamorada
Anglers Reef Islamorada Oceanside 2/2.5+Pool+Beach
5 min drive
5 min drive
Apr 20 – 27
Apr 20 – 27
$300
night
$300 per night
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favorite
Guest favorite
Home in Islamorada
Hidden Gem Duplex in Heart of Islamorada! Sleeps 8
9 min walk
9 min walk
Aug 10 – 15
Aug 10 – 15
$708
night
$708 per night
4.94 out of 5 average rating, 17 reviews
4.94 (17)
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