Luxury Vacation Rentals in Key West

(19 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

$1752

avg/night

$1,752
avg per night
View Details

Key Amenities

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

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 | On the beach
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 3 Bathrooms
1 review

$967

avg/night

$967
avg per night
View Details

Key Amenities

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

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 House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
5 reviews

$727

avg/night

$727
avg per night
View Details

Key Amenities

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

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, ...

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Property Type

Key West House

Featured review

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used ...

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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

$1286

avg/night

$1,286
avg per night
View Details

Key Amenities

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

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
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 3 Bathrooms
4 reviews

$811

avg/night

$811
avg per night
View Details

Key Amenities

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

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny ...

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Property Type

Key West House

Featured review

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to ...

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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

$1318

avg/night

$1,318
avg per night
View Details

Key Amenities

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

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 | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$809

avg/night

$809
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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 Condo
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms

$1000

avg/night

$1,000
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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 | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$1052

avg/night

$1,052
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the master bedroom, 2 twins in the guest bedroom (which can also be converted to a King bed upon request) and a queen sleeper sofa in the living room.Anchor Drop is beautifully renovated ...

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Property Type

Key West Condo

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Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom
1 review

$1712

avg/night

$1,712
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever ...

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Property Type

Key West Condo

Featured review

"Perfect location! Beautiful property!"

This was an amazing spot for a vacation! The condo was walking distance to everything! Beautiful beaches, amazing parks, Hemingway House, Duval Street, the aquarium. The property within the gated community ...

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$1053

avg/night

$1,053
avg per night
View Details

Key Amenities

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

About this property

This condo has been beautifully renovated. Both bedrooms and the living room open onto a spacious 40 ft private balcony. There is a King Bed in the Master bedroom and 2 twin beds in the guest bedroom.1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City ...

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Property Type

Key West Condo

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
1 review

$878

avg/night

$878
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms ...

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Property Type

Key West Condo

Featured review

"SIMPLY DIVINE"

BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO ...

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Beautifully renovated, this 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. The fabulous kitchen features stainless steel appliances and granite countertops. Enjoy breathtaking sunrises from the balcony, where you can awaken to morning reflections.The recently ...

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Property Type

Key West Condo

Featured review

"beautiful ocean view condo"

condo was very clean and on the top floor with vault ceilings. Check in process was seamless as well as checkout.

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Key West Condo | On the beach
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$1409

avg/night

$1,409
avg per night
View Details

Key Amenities

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

About this property

This is a spectacular 3 bedroom 2 bath ocean front unit in a premier location in the complex. Conveniently located close to the elevator with covered secure parking in the garage for a vehicle under 6ft 4 inches. Around 2000 sq feet, each bedroom and living room have sliding glass doors that open onto ...

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Property Type

Key West Condo

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$989

avg/night

$989
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer. Both bedrooms and the living room have impact doors open to your private balcony. There is a King bed in the master bedroom and a queen ...

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Property Type

Key West Condo

Featured review

"New Year’s vacation"

Wanted to go to the Florida Keys, but this place popped up several times during my search. I’m so glad I chose this place. Breathe taking is the best word to use. Beautiful beach (7miles of it), nice ...

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Key West House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Kid friendly
  • Kitchen
  • Pool

About this property

3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a nice ...

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Property Type

Key West House

Featured review

"Southern Charm with a boat slip!"

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This ...

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$1633

avg/night

$1,633
avg per night
View Details

Key Amenities

  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

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

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

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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$791

avg/night

$791
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Blue Haven: An Exquisite Oceanfront Penthouse – Complete Remodel with Direct Ocean Views and Massage Chair – Premier Unit on Property Blue Haven is the premiere property in this complex. This luxury penthouse condominium is unbelievable. You will not want to leave. Nestled on the shore of ...

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Property Type

Key West Condo

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Key West Vacation Rentals