Luxury Vacation Rentals in Key West

(13 rentals)
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Key West Villa
6 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 6 bedrooms, 7 bathrooms
3 reviews

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1597

avg/night

$1,597
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

Featured review

"Glenn dinner group get away"

We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not ...

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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. ...

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Property Type

Key West House

Featured review

"Highly Recommend!"

My husband and I recently rented this home for a month and we couldn’t have enjoyed it more! Let me start with our favorite space… the backyard. From the heated pool, to the outdoor shower, guest house, ...

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Key West Yacht
5 BR | 5.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5.5 bathrooms
3 reviews

$1091

avg/night

$1,091
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

VACATION RENTALSFlorida offers amazing opportunities on the water aboard private yacht, Lady Grace, which is available for winter vacation rentals in Key West. Lady Grace provides a relaxing retreat and the thrill of living on your own private 92-foot yacht with plenty of space for enjoying time ...

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Property Type

Key West Yacht

Featured review

"Amazing Week Cruising"

“My family and I just spent an amazing week cruising around the Gulf Of Mexico visiting Key West and the Dry Tortugas onboard The Lady Grace. The accommodations were incredible with spacious staterooms ...

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Key West House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

$902

avg/night

$902
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants ...

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Property Type

Key West House

Featured review

"Wonderful property wonderful hosts!"

I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away ...

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Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$1192

avg/night

$1,192
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Suncatcher on the ocean is new to the rental pool at 1800 Atlantic. A fabulous property with many upgrades throughout. Totally renovated from top to bottom with high end finishes and no attention to detail spared. We are excited to offer it for rent for the first time. Tastefully decorated in Island ...

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Property Type

Key West Condo

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Key West House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews

$833

avg/night

$833
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.*Saturday-to-Saturday Rentals OnlyProperty Overview:Prime Location: Casa Rosa is situated in a picturesque neighborhood, just one block away from Key West's renowned Duval Street. Casa Rosa ...

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Property Type

Key West House

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Key West Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$742

avg/night

$742
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

3 Bedroom, 3 Bath Partial Ocean ViewAtlantic Sunrise is the only 3-bedroom, 3-bath unit in the complex, spanning approximately 2,000 square feet and accommodating up to 8 guests. It features two master suites, each with a king bed, while the third bedroom has 2 twin beds. Additionally, there is a ...

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Property Type

Key West Condo

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Key West Condo
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$711

avg/night

$711
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Mar Y Sol is a beautiful oceanfront condominium featuring three bedrooms and two and a half bathrooms, located at 1800 Atlantic. Enjoy the balmy breezes from your 60-foot private wrap-around balcony, which offers a stunning view of the Atlantic Ocean.The condominium includes renovated kitchens and ...

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Property Type

Key West Condo

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Key West House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Distance to beach: 50 yards to One block from fantastic beach

$781

avg/night

$781
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This one of a kind beautiful home was built in 1912 by one of the first cigar makers. It is listed on the National registry of historic homes and has been showcased in the Holiday Parade of Homes. The home was restored and expanded in 2002 Key West contractor Richard Manley with the highest level of ...

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Property Type

Key West House

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Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$714

avg/night

$714
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Tom's Oceanfront Penthouse is a spectacular oceanfront unit features 3 bedrooms and 2 bathrooms in a prime location within the complex. It is conveniently situated near the elevator and offers secure covered parking in the garage for vehicles under 6 feet 4 inches in height.Spanning approximately ...

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Property Type

Key West Condo

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Key West Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

$1043

avg/night

$1,043
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Keys to Paradise: A 5-Star Beachside RetreatThis beautiful 3-bedroom, 2-bath condo is located in a private beachside resort, conveniently close to Old Town Key West and just steps away from the beach. It's also an easy bike ride to all that Key West has to offer.Keys to Paradise is a direct ...

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Property Type

Key West Condo

Featured review

"Absolutely Amazing"

The condo was beautiful, offering stunning views of the harbor and boat races. It was conveniently located near Duval Street but far enough awayeace and quiet. Alice and Charli to enjoy some pe were fantastic ...

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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$1400

avg/night

$1,400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a slighly large balcony. Access the Balcony from both bedrooms and the living room. There is a full size fully equipped eat in Kitchen and a Full size washer dryer. Enjoy all the comforts ...

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Property Type

Key West Condo

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Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$1860

avg/night

$1,860
avg per night
View Details

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West. The property has a queen bed in each bedroom and the master has an en suite bathroom. Totally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach. The living room has a flat screen smart TV ...

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Property Type

Key West Condo

Featured review

"Vacation"

Very thing was good the condo was perfect and the pool was great the parking was close to the elevator

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Key West Vacation Rentals