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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
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
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
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
2 min drive
2 min drive
May 31 – Jun 5
May 31 – Jun 5
$200
$180
night
$180 per night, originally $200
4.92 out of 5 average rating, 325 reviews
4.92 (325)
Guest favorite
Guest favorite
Houseboat in Islamorada
Aqua Lodge Houseboat 2bd/1Bth!
8 min drive
8 min drive
May 16 – 21
May 16 – 21
$299
$205
night
$205 per night, originally $299
4.94 out of 5 average rating, 16 reviews
4.94 (16)
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
Home in Islamorada
Waterfront Home w/private dock & Sunset views
2 min drive
2 min drive
May 3 – 9
May 3 – 9
$1,111
night
$1,111 per night
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Guest favorite
Guest favorite
Apartment in Islamorada
Hidden Gem Islamorada | 1st Floor
9 min walk
9 min walk
Aug 10 – 15
Aug 10 – 15
$309
night
$309 per night
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Apartment in Islamorada
Convenient Location! Free Parking, Onsite Pool
3 min walk
3 min walk
Apr 21 – 26
Apr 21 – 26
$614
night
$614 per night
Superhost
Superhost
Cottage in Islamorada
1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON
8 min drive
8 min drive
Jul 7 – 12
Jul 7 – 12
$199
night
$199 per night
4.85 out of 5 average rating, 124 reviews
4.85 (124)
Guest favorite
Guest favorite
Boat in Islamorada
HOUSEBOAT 2BD, PRIVATE KEYS COTTAGE LOGGERHEAD
8 min drive
8 min drive
May 5 – 10
May 5 – 10
$299
$189
night
$189 per night, originally $299
4.9 out of 5 average rating, 167 reviews
4.9 (167)
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)
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
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, 9 reviews
5.0 (9)
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
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)
Guest favorite
Guest favorite
Bungalow in Islamorada
Dream in Paradise! King Master, Queen Guest, Pool
10 min drive
10 min drive
Jun 15 – 20
Jun 15 – 20
$619
night
$619 per night
4.97 out of 5 average rating, 29 reviews
4.97 (29)
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)
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