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Office Location:
Key West, FL, USA

Total Properties: 61

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  1092 reviews

Rent Key West Vacations

Key West and great memories go hand in hand, and Rent Key West Vacations helps you make more great memories than you ever imagined by offering the best vacation rentals in the Florida Keys. After all, the right home, condo or villa goes a long way towards making your experience as enjoyable as possible. Our team of professionals will work their hardest to ensure everything goes as planned with your rental and vacation.

Rent Key West Vacations has the experience and know-how to back up this promise. We're one of the oldest vacation rental companies in Key West. In 1996, Roberta Lowe and Dawn Thornburgh joined forces under the Rent Key West banner. Then, in 2000, Paul Hayes and Dean Carlson purchased the company and grew it to its current size. Both Dean and Paul have an amazing amount of knowledge about vacation rental property management, and in 2005 Paul served as President of the Florida Vacation Rental Managers Association.

The professional staff at Rent Key West Vacations gets to know each guest personally--we work as a family and friends organization. We find out what interest you and what you expect to get out of your vacation, then help you find the right activities, restaurants, shopping, excursions and more.

Key West is one of the most unique, enjoyable and popular vacation destinations in the world. There are land titles dating back to the time of Spanish rule, so the region is steeped in history. You'll also find the John Audubon House and Ernest Hemmingway's home. Many other famous, creative and influential people have called Key West home at one time or another, among them Thomas Edison, Lou Gehrig, Harry Truman and Tennessee Williams. Key West has long been a playground for the rich, famous, artists and writers.

Of course, there's plenty of modern-day action. Enjoy the spontaneous sunset celebrations on Mallory Dock, then revel in delectable sidewalk cafes, fun open-air bars, pubs, delicious restaurants, as well as plays and musicals in Key West's theaters.

Since it's Key West, there's an almost endless amount of other activities--shopping, watersports, golf and more.

When you book a Rent Key West Vacations property, rest assured that you'll have all of our passion, energy and years of experience working for you. Take a look at the properties available on Perfect Places, make your selection, book it, and then relax and get ready to have a truly memorable vacation.
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Listings 1 - 25 of 61
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1 bedroom Vacation Rental Condo in Key West
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
Rates
$190 - $250 night
$1260 - $1680 week


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1 bedroom Vacation Rental Cottage in Key West
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
Rates
$190 - $250 night
$1260 - $1680 week


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1 bedroom Vacation Rental Condo in Key West - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
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
$170 - $240 night
$1120 - $1610 week


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1 bedroom Vacation Rental Home in Key West
Home: 1 Bedroom, 1.5 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL An amazing renovation of mid town historic home with the Washington Street address many desire. This charming one bedroom bun... Learn More
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1 bedroom Vacation Rental Home in Key West - Ocean View
Home: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: A spacious studio apartment and large deck make this the perfect romantic getaway, feast your eyes on the breathtaking views of the Atlantic Ocean.... Learn More
Rates
$160 - $200 night
$1050 - $1330 week


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1 bedroom Vacation Rental Condo in Key West
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL A spacious ground floor one bedroom in a four unit condominium building in the Casa Marina District of Key West. A great apar... Learn More
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1 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: Situated on the Atlantic shore of Key West and offering breathtaking panoramas, this outstanding property was featured in Architectural Digest. Fil... Learn More
Rates
$170 - $220 night
$1120 - $1470 week


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1 bedroom Vacation Rental Condo in Key West
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.... Learn More
Rates
$200 - $260 night
$1330 - $1750 week


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1 bedroom Vacation Rental Home in Key West
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
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1 bedroom Vacation Rental Condo in Key West
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: This charming one bedroom cottage is the perfect hideaway. A homey, inviting compound created so owners could enjoy shared tropical outdoor spaces.... Learn More
Rates
$190 - $250 night
$1260 - $1680 week


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1 bedroom Vacation Rental Condo in Key West
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL A spacious one bedroom in a four condominium building in the Casa Marina District of Key West. The cool, classy decor and whi... Learn More
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: This property has it all! This award winning renovation has been completed recently and offers the styling of the original shot gun homes of Key W... Learn More
Rates
$260 - $330 night
$1680 - $2170 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
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
Rates
$180 - $280 night
$1190 - $1820 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and... Learn More
Rates
$220 - $330 night
$1470 - $2240 week


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: Duval Square - The Retreat. In the heart of Old Town, Duval Square is located at the "artistic" and more quiet end of Duval Street. This recently... Learn More
Rates
$250 - $310 night
$1680 - $2030 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
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 2 bedroom 2 bath unit has a wonderf... Learn More
Rates
$270 - $400 night
$1820 - $2730 week


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2 bedroom Vacation Rental Condo in Key West - Ocean View
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 2 bedroom 2 bath unit features a hu... Learn More
Rates
$270 - $400 night
$1820 - $2730 week


High-Speed Internet


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2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: Let "the breeze" of La Brisa cool you as you relax on your ocean view balcony. This residential condominium complex is situated opposite the larg... Learn More
Rates
$200 - $290 night
$1330 - $1960 week


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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL This amazing restoration of a majestic Key West bungalow is incredible. Modernists will love this property. This two bed... Learn More
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 1 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for... Learn More
Rates
$270 - $350 night
$1820 - $2310 week


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2 bedroom Vacation Rental Home in Key West
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
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2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the l... Learn More
Rates
$320 - $430 night
$2030 - $2800 week


Pet Friendly   High-Speed Internet


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2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes tha... Learn More
Rates
Contact Owner
Directly For Rates


View Details Send Inquiry



2 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: Unique oceanfront living sitting 65 feet from the Atlantic. Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features... Learn More
Rates
$270 - $400 night
$1820 - $2730 week


Non Smoking   High-Speed Internet


View Details Send Inquiry



2 bedroom Vacation Rental Home in Key West
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: 30 DAY MINIMUM RENTAL ALBURY BUNGALOW A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. This one ... Learn More
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