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Over 1,000 places

Home in Key Colony Beach
Splash Into Me - MA1060
4 beds
Oct 1 – 8
$305 per night
Superhost
Apartment in Key West
At Mine | Lovely Suite steps from Duval Street
1 bed
Oct 1 – 6
$112 per night, originally $176
Superhost
Home in Marathon
Beach House, Private Pool & Dock, Gulf Sunset view
2 beds
Oct 7 – 14
$266 per night, originally $495
Superhost
Boat in Key West
Tiki Suites ~ The Grand Tiki
1 bed
Oct 21 – 26
$749 per night
Apartment in Key West
Beautiful King Bedroom + Pools & Free Shuttle
1 king bed
Oct 1 – 6
$129 per night
Superhost
Home in Marathon
Oceanfront w/ Dock, Hot Tub & Secluded
2 beds
Oct 1 – 8
$141 per night
Superhost
Home in Key Largo
The Paradise 2
3 beds
Oct 13 – 18
$275 per night
Superhost
Apartment in Key West
At Mine | Key west
1 bed
Oct 1 – 6
$106 per night
Superhost
Home in Islamorada
Flakey's
3 beds
Oct 7 – 14
$150 per night, originally $228
Home in Marathon
Serenity at Sombrero | Private Pool, Spa & Dock
5 beds
Oct 14 – 21
$199 per night, originally $349
Superhost
Vacation home in Key Largo
Waterfront, GROUND LEVEL, Awesome Sunsets!!!
1 bed
Oct 1 – 6
$133 per night, originally $157
Home in Marathon
Super Snapper lux w/Heated Pool, Tiki, Dock, Lanai
5 beds
Oct 14 – 21
$304 per night
Apartment in Key West
King Bed No Cleaning Fee & Access To 4 Pools
1 king bed
Oct 1 – 6
$129 per night
Superhost
Tiny home in Key Largo
The Oasis in key largo with your own private beach
2 beds
Oct 31 – Nov 5
$198 per night, originally $250
Superhost
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
3 beds
Oct 1 – 6
$318 per night, originally $572
Superhost
Home in Key Colony Beach
Huge Fall savings! Paradise found with pool club
3 beds
Oct 14 – 21
$135 per night, originally $235
Superhost
Home in Marathon
Waterfront Tropical Oasis in the FL Keys
4 beds
Oct 14 – 21
$283 per night, originally $354
Superhost
Guest suite in Key Colony Beach
Turtle-By-The-Sea: the Best Deal in KCB!
1 queen bed
Oct 14 – 21
$125 per night