Luxury Vacation Rentals in Key West

(67 rentals)
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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning is $120 * This is not a hotel; it is a privately owned condo facing the ...

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Property Type

Key West Condo

"The perfect location that has everything..."

Just finished a 2 week stay and I have been renting from Pam for over a decade and she continues to make a great condo even better with her constant upgrades to the unit and she is a wonderful host. The ...

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4 BR | 2.5 BA | Sleeps 8 | Quick View

2
owner special
Owner special: Half price! May 2024

Distance to beach: 600 yards to Simonton Street Beach

$300

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen ...

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Property Type

Key West House

"Tropical Paradise"

This property was absolutely amazing! Being in Old Town and just steps away from Caroline St and a few blocks from Duval was so convenient. We were traveling with our adult children and everyone could come ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap around porch, a pool deck and a heated dipping pool/large ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

"Great location!"

We loved this house at the end of a quiet lane. Huge pool! The location was perfect, walking was easy to so many places. Fully fenced and a small backyard made it perfect for our dog. And the shower ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beautifully decorated with amazing outside space to enjoy our island breezes and cool off in our pool. This beautiful property has been well maintained with a newly renovated Kitchen. Queen ...

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Property Type

Key West Cottage

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1 BR | 2 BA | Sleeps 2 | Quick View

1

$275

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history that befits its esteemed place along one of the most elegant streets in Key West. Unit # 6 is a second floor, 1BR/2BA unit that is entered on the left side of the building. The condo ...

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Property Type

Key West Condo

"Perfect place for a warm-weather couple!"

The location is perfect! Close to Duval Street, Mallory Square and many fabulous shops. We rode our bikes every morning to Higgs Beach to play tennis then enjoyed the white sand and cool morning breeze ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the ...

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Property Type

Key West House

"Key West paradise"

Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the ...

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1 BR | 1 BA | Sleeps 2 | Quick View

2

$257

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

We specialize in amazing vacations and honeymoon and extended stays for two guests, aboard a yacht that stays dockside without the chance of seasickness allowing you to come and go according to your own schedule. Our pedigree Hatteras, a custom 60' motor yacht, a timeless classic designed for elegant ...

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Property Type

Key West Yacht

"Great experience!"

The Paradise is a grogerous yacht. The woodworking is amazingly beautiful. The bed is very comfortable. We really enjoyed our stay and was very pleased. Captain Berry & Tamara were very tentative and superior ...

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Studio | 1 BA | Sleeps 2 | Quick View

5

Distance to beach: 0.5 miles to South Beach

$244

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 *Cleaning fee of $70 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress ...

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Property Type

Key West Condo

"Fantasic studio unit and a great location."

Very clean and well-equipped unit. It comes with cable tv and great internet. It is a great location, one block from Duval st.

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2 BR | 2 BA | Sleeps 6 | Quick View

$242

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv in ...

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Property Type

Key West House

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Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$241

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill ...

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Property Type

Key West Condo

"Perfect Place to Stay"

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

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2 BR | 2 BA | Sleeps 4 | Quick View

3

$229

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Welcome to Key West Getaway in Old Town!This three-story townhome offers a great layout to enjoy your monthly stay. Enter the ground level just steps away from your dedicated parking spot to a den with a convenient workstation and television. The couch in the den pulls out to a queen sleeper. Level ...

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Property Type

Key West Townhome

"Fantastic location and unit!"

We stayed at Holly's Key West Getaway from October 2022 through May 2023, and it was absolutely fantastic. The unit is in a complex perfectly located in Key West, within blocks of great restaurants, attractions, ...

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2 BR | 2 BA | Sleeps 4 | Quick View

6

Distance to beach: 1 miles to Fort Zachery Taylor State Park

$229

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy ...

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Property Type

Key West House

"Just Perfect"

Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A gorgeous 3 bedroom / 2 bathroom vacation rental home with high vaulted ceilings and french doors that bring the outside in. The backyard features a large covered patio and an in-ground heated swimming pool, perfect for relaxing anytime of the year. New outside table with seating and gas bbq grill ...

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Property Type

Key West House

"Wonderful Retreat"

This house was truly a private haven. It was so quiet and peaceful but yet so centrally located in the island. Quick golf cart rides to Duval and local shops plus near beaches. The house was very neat and ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$203

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

About this space Built in 2022, this vibrant, 1400 sq ft stilted home brims with personalized art and touches inspired by The Keys history, landscapes and local artisans. From this luxurious retreat you will enjoy a crystal-clear canal access, a private dock, a tropical micro pool, a stocked chef's ...

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Property Type

Key West House

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3 BR | 2 BA | Sleeps 6 | Quick View

$200

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms. ...

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Property Type

Key West House

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Key West Vacation Rentals