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Price: high to low
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264 Houses
Price per night from
$72

((Fantastic value for last minute discounts for gaps ))
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$516
* Best of the Annex Waterfront with Fantastic Weekly Rates *
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$589
* New Ownership, New Look, Ocean Hideaway Winter Savings Book now *
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$390
*Spring Discounts Stay on the Ocean Last minute Specials Book & Save *
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$413
* Last minute Specials Caribbean Conch Key West Condo Save *
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$395
“Coral Villa” This rental was perfect for my family. It was about 10-15 minutes from Duvall Street and Old Town Key West. The pool was a great place to relax. The only downside was the noise from the road right behind our rental, after the first night though we did not notice the noise anymore.
Price per night from
$106
Salt Ponds Sanctuary - Lovely Condo w/ Private Balcony, Shared Pool/Hot Tub, Nea
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$115
New Listing!!! Cocktails & Dreams - Updated Condo, Walk To Duval St, Waterpark,
Stock Island condo
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$174
Ocean Breeze - Fantastic Smathers Beach Views, Top Floor Condo With Private Balc
Stock Island condo
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$237
Price per night from
$72
Ella Varela - Beautiful Dog Friendly Conch Cottage Conveniently Located in the H
Stock Island house
2 bedrooms / 1 bathroom / sleeps 4
Price per night from
$174
Coconut Mallory #411, Key West Convenience + Resort Amenities, Pools, Hot Tub, D
Stock Island condo
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$174
Coconut Mallory #412, Resort Amenities, Pools, Hot Tub, Dockage, Pub and Key Wes
Stock Island condo
1 bedroom / 1 bathroom / sleeps 4
Price per night from
$174
Lotus Blossom - Updated 3 BR Home With Tropical Courtyard & Hot Tub, Convenient
Stock Island house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$93
Margaretaville - Live Like A Key West Local, Dog Friendly Old Town Home With Pri
Stock Island house
2 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$243
Great rentals within 20 miles that match your search
Price per night from
$555
Price per night from
$343
Welcome Aboard! Relax, unwind, enjoy the water! in key west
Key West yacht
4 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$322
Price per night from
$383
Old Town Treasure, Historic Seaport, Conch House 3 Bedrooms 3.5 Baths, Pool
Key West house
3 bedrooms / 4 bathrooms / sleeps 6
Price per night from
$466
Price per night from
$387
Price per night from
$582
Price per night from
$542
Old Town, 5 Bdrm Home with Private Pool in Gated Backyard
Key West house
5 bedrooms / 4 bathrooms / sleeps 10
Responds fast! avg. 1 hour 18 minutes
Price per night from
$359
“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.
Price per night from
$298