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Search results; Over 1,000 places

Guest favorite
Condo in Key West
*Come to my Deck for a time you won't Forget!
18 min drive
Apr 27 – May 3
4.99 out of 5 average rating, 78 reviews
Boat in Marathon
Paradise awaits on this cozy houseboat!
1 king bed
May 8 – 13
4.77 out of 5 average rating, 162 reviews
Guest favorite
Condo in Key West
Walk to beach, Duval, Mallory Sq
17 min drive
Jul 27 – Aug 3
5.0 out of 5 average rating, 8 reviews
Apartment in Key West
Great Location: Two Queen Beds
7 min drive
Apr 22 – 27
4.28 out of 5 average rating, 18 reviews
Home in Key West
Waterfront house-15 minutes from Key West-Private
15 min drive
Aug 18 – 25
4.75 out of 5 average rating, 8 reviews
Condo in Key West
Coconut Mallory 2 BD Condo-224
8 min drive
May 13 – 18
New place to stay
Guest favorite
Room in Key West
Nuns Room, A single travelers delight!
16 min drive
Jun 10 – 15
4.96 out of 5 average rating, 131 reviews
Hotel in Stock Island
Time to relax Bathtub & jets perfect place 2 sleep
7 min drive
May 4 – 9
4.59 out of 5 average rating, 17 reviews
Superhost
Boutique hotel in Key West
Mallory House Room #3
16 min drive
Jun 29 – Jul 4
4.9 out of 5 average rating, 353 reviews
Superhost
Townhouse in Key West
Poolside Cottage #412
8 min drive
Aug 5 – 10
4.86 out of 5 average rating, 127 reviews
Guest favorite
Home in Ramrod Key
Canalfront 3BD/2BA|FLKeys|POOL|DOCK
41 min drive
Mar 6 – 11
5.0 out of 5 average rating, 6 reviews
Superhost
Houseboat in Marathon
Houseboat Getaway In Marathon
4 beds
Apr 26 – May 1
4.84 out of 5 average rating, 61 reviews
Guest favorite
Room in Marathon
Stay with CharlesHosting for 7 years,
Island Yacht Adventures
May 19 – 24
4.99 out of 5 average rating, 397 reviews
Guest favorite
Home in Cudjoe Key
May Extravaganza - Relax in Paradise!
31 min drive
Oct 1 – 8
4.94 out of 5 average rating, 17 reviews
Guest favorite
Condo in Key West
Hidden Beach Duplex, Best Place in Key West
16 min drive
May 26 – 31
4.99 out of 5 average rating, 83 reviews
Guest favorite
Guest suite in Big Pine Key
Old Island Life
46 min drive
Apr 27 – May 2
4.87 out of 5 average rating, 471 reviews
Guest favorite
Apartment in Key West
Poolside Truman Annex 2 Bed | Conch Life Condo
18 min drive
Jun 14 – 19
4.97 out of 5 average rating, 236 reviews
Apartment in Big Pine Key
New Deluxe Duplex Unit 1 Queen Bed, Full Kitchen
50 min drive
Apr 21 – 26
4.86 out of 5 average rating, 42 reviews