Key West Vacation Rentals
212 Key West Vacation Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Key West, Florida Keys, Florida, United States.
Condo:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony with... Learn More
Location: Key West, Florida, United States
Description: Located in a very quiet corner of Truman Annex, this condo is a perfect getaway. This one bedroom and one bathroom unit has a spacious balcony with... Learn More
Rates
$1200 - $1750 week
$1200 - $1750 week
Featured
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our ... Learn More
Location: Key West, Florida, United States
Description: Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our ... Learn More
Rates
$225 - $299 night
$1575 - $2093 week
$225 - $299 night
$1575 - $2093 week
Featured
Home:
5 Bedroom, 4 Bathroom, Sleeps 10
Location: Key West, Florida, United States
Description: There's a new place on Duval Street in historic Key West and it is unique! Dreaming On Duval premieres in early 2010 as the most luxurious single ... Learn More
Location: Key West, Florida, United States
Description: There's a new place on Duval Street in historic Key West and it is unique! Dreaming On Duval premieres in early 2010 as the most luxurious single ... Learn More
Rates
$870 - $2000 night
$5950 - $14000 week
$870 - $2000 night
$5950 - $14000 week
Featured
Condo:
2 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below ... Learn More
Location: Key West, Florida, United States
Description: Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below ... Learn More
Rates
$225 - $275 night
$1575 - $1925 week
$225 - $275 night
$1575 - $1925 week
Featured
Cottage:
1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound just one half block off Duva... Learn More
Location: Key West, Florida, United States
Description: Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound just one half block off Duva... Learn More
Rates
$190 - $250 night
$1260 - $1680 week
$190 - $250 night
$1260 - $1680 week
Featured
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our ... Learn More
Location: Key West, Florida, United States
Description: Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our ... Learn More
Rates
$225 - $299 night
$1575 - $2093 week
$225 - $299 night
$1575 - $2093 week
Featured
Home:
5 Bedroom, 6 Bathroom, Sleeps 12
Location: Key West, Florida, United States
Description: THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis... Learn More
Location: Key West, Florida, United States
Description: THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis... Learn More
Rates
$865 - $1776 night
$5800 - $12035 week
$865 - $1776 night
$5800 - $12035 week
Featured
Home:
2 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: TROPICAL DREAMING -- This tropical 2-bedroom home has been professionally decorated and furnished. There are classic art features, hardwood floors... Learn More
Location: Key West, Florida, United States
Description: TROPICAL DREAMING -- This tropical 2-bedroom home has been professionally decorated and furnished. There are classic art features, hardwood floors... Learn More
Rates
$340 - $682 night
$2100 - $4350 week
$340 - $682 night
$2100 - $4350 week
Featured
Condo:
1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true is... Learn More
Location: Key West, Florida, United States
Description: Located just a step away from Old Town area surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true is... Learn More
Rates
$190 - $250 night
$1260 - $1680 week
$190 - $250 night
$1260 - $1680 week
Featured
Home:
3 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL From the owners of South of Frances here is another beautiful restoration of a Key West historic property. This lovingly res... Learn More
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL From the owners of South of Frances here is another beautiful restoration of a Key West historic property. This lovingly res... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Home:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most photographed "Prohi... Learn More
Location: Key West, Florida, United States
Description: Unique two story, three bedroom, two bathroom home nested beside the Audubon House in Old Town Key West. Hidden behind the most photographed "Prohi... Learn More
Rates
$370 - $500 night
$2380 - $3290 week
$370 - $500 night
$2380 - $3290 week
Home:
1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's... Learn More
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL The meadows of Key West is a lovely, quiet and historic neighborhood located just behind Old Town Key West and known for it's... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This is one of the most elegant and col... Learn More
Location: Key West, Florida, United States
Description: Unique oceanfront living sitting 65 feet from the Atlantic. Listen to the water as ocean breezes cool you. This is one of the most elegant and col... Learn More
Rates
$270 - $400 night
$1820 - $2730 week
$270 - $400 night
$1820 - $2730 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks fro... Learn More
Location: Key West, Florida, United States
Description: THE HEMINGWAY -- A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks fro... Learn More
Rates
$1300 - $2864 week
$1300 - $2864 week
Condo:
2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: FINN KEY: A beautiful 2 bedroom 1 bath downstairs condominium located in the Shipyard section of Truman Annex, a gated residential community i... Learn More
Location: Key West, Florida, United States
Description: FINN KEY: A beautiful 2 bedroom 1 bath downstairs condominium located in the Shipyard section of Truman Annex, a gated residential community i... Learn More
Rates
$1100 - $2538 week
$1100 - $2538 week
Home:
3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. ... Learn More
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL Packer Retreat is a beautifully renovated "Conch" house with many architectural touches in the charming historic district. ... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Condo:
2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States
Description: LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk of Truman An... Learn More
Location: Key West, Florida, United States
Description: LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath townhome located in the President's Walk of Truman An... Learn More
Rates
$1300 - $2864 week
$1300 - $2864 week
Home:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: SOUTHERN WIND -- A renovated two bedroom two bath two story home located in the Windward Park compound in the heart of Old Town and walking distanc... Learn More
Location: Key West, Florida, United States
Description: SOUTHERN WIND -- A renovated two bedroom two bath two story home located in the Windward Park compound in the heart of Old Town and walking distanc... Learn More
Rates
$265 - $471 night
$1575 - $2900 week
$265 - $471 night
$1575 - $2900 week
Home:
2 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of the Truman Annex. Thi... Learn More
Location: Key West, Florida, United States
Description: ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private home located in the prestigious Admirals Lane neighborhood of the Truman Annex. Thi... Learn More
Rates
$1700 - $3425 week
$1700 - $3425 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty b... Learn More
Location: Key West, Florida, United States
Description: La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty b... Learn More
Rates
$180 - $280 night
$1190 - $1820 week
$180 - $280 night
$1190 - $1820 week
Home:
2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been co... Learn More
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's "Guestbook" column, this charming Old Town house has recently been co... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Home:
2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White... Learn More
Location: Key West, Florida, United States
Description: A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. Guests can walk to the nearby beaches, artsy White... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Home:
1 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: ATLANTIC BLUES - Is a stylish example of a Conch cottage, totally renovated with gorgeous hardwood floors, beautiful glass tiles, shining granite ... Learn More
Location: Key West, Florida, United States
Description: ATLANTIC BLUES - Is a stylish example of a Conch cottage, totally renovated with gorgeous hardwood floors, beautiful glass tiles, shining granite ... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Condo:
4 Bedroom, 5 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the ... Learn More
Location: Key West, Florida, United States
Description: Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4.5 bath condo is in the heart of the ... Learn More
Rates
$410 - $590 night
$2730 - $3990 week
$410 - $590 night
$2730 - $3990 week
Condo:
2 Bedroom, 2 Bathroom, Sleeps 5
Location: Key West, Florida, United States
Description: PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this home is in a great location and a great value for a great... Learn More
Location: Key West, Florida, United States
Description: PARROT PERCH -- Located in the gated Shipyard Community in prestigious Truman Annex, this home is in a great location and a great value for a great... Learn More
Rates
$1100 - $2538 week
$1100 - $2538 week
This map is intended to be used as a reference only.
Please confirm the exact location with the property owner or manager.
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