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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 26 - 50 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: 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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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town... Learn More
Rates
$558 - $658 night
$3906 - $4606 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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4 bedroom Vacation Rental Home in Key West
Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: Amazing, sophisticated home in the fabulous Truman Annex enclave. You can't beat an Admiral's Lane address in Key West. So near the Caroline Stre... Learn More
Rates
$5500 - $7500 week


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4 bedroom Vacation Rental Home in Key West
Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacat... Learn More
Rates
$730 - $930 night
$4900 - $6300 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. Enjoy an ocean view as ocean breezes cool you. This spacious 2 bedroom unit features... Learn More
Rates
$270 - $400 night
$1820 - $2730 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 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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3 bedroom Vacation Rental Condo in Key West - Ocean View
Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
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
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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: 30 DAY MINIMUM RENTAL Unique oceanfront living sitting 65 feet from the Atlantic awaits you at the Key West Beach Club. Listen to the water as oce... 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: 30 DAY MINIMUM RENTAL ANGELA COTTAGE This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central lo... 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: 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
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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three... Learn More
Rates
$380 - $540 night
$2450 - $3570 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 is one of the most elegant and col... Learn More
Rates
$270 - $400 night
$1820 - $2730 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Key West
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
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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town... Learn More
Rates
$558 - $658 night
$3906 - $4606 week


High-Speed Internet


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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: In the fabulous Truman Annex enclave and near the Caroline Street walking gate directly to downtown Key West, this nicely decorated home features ... Learn More
Rates
$4500 - $6500 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: Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 40... Learn More
Rates
$250 - $290 night
$1680 - $1960 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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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 4 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Island elegance and a blend of modern sophistication marks this distinctive four level waterfront luxury property. Offering the best of Florida Ke... Learn More
Rates
$458 - $658 night
$3206 - $4606 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: 30 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your ocean view or natural water sanctuary view balcony. This resident... Learn More
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3 bedroom Vacation Rental Condo in Key West
Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
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 that... Learn More
Rates
Contact Owner
Directly For Rates


View Details Send Inquiry



2 bedroom Vacation Rental Condo in Key West
Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Key West, Florida, United States
Description: In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard Condominium is great access ... Learn More
Rates
$1190 - $1820 week


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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
$280 - $330 night
$1820 - $2170 week


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4 bedroom Vacation Rental Home in Key West
Home: 4 Bedroom, 2 Bathroom, Sleeps 8
Location: Key West, Florida, United States
Description: This property has it all! This award winning renovation offers the styling of the original shot gun homes of Key West restored with a beautiful ... Learn More
Rates
$450 - $620 night
$3010 - $4340 week


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3 bedroom Vacation Rental Home in Key West
Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Key West, Florida, United States
Description: Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duv... Learn More
Rates
$470 - $650 night
$3080 - $4340 week


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Listings 26 - 50 of 61
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