Vacation Rentals in Key West

Windsor Townhome #2

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…

• from
• $458
  nightly
• 
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Tortuga Hammock

• 2 Bedrooms, 3 Bathrooms, Sleeps 4
• Tortuga Hammock – Stock Island Not even 1 mile from Key West proper, this gem is hidden right off of…

• from
• $258
  nightly
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La Casa Cubana

• 1 Bedroom, 1.5 Bathrooms, Sleeps 6
• La Casa Cubana – Old Town Sitting just steps around the corner from the infamous Duval Street, this spacious 1…

• from
• $188
  nightly
• 
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Orchid Suite

• 1 Bedroom, 1 Bathroom, Sleeps 6
• The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with…

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• $178
  nightly
• 
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Colors on White

• 5 Bedrooms, 5 Bathrooms, Sleeps 17
• Colors on White– Old Town Colors on White is located in the heart of the White Street art district, just…

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• $515
  nightly
• 
  Compare

Casa Loca

• 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
• Casa Loca – Old Town is perfect for the discriminating guest who wants to enjoy the finest Key West has…

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• $458
  nightly
• 
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Hidden Treasure

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Hidden Treasure – Old Town Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping,…

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• $258
  nightly
• 
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Island style

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Island Style– Old Town Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages,…

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• $188
  nightly
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Cuban Paradise

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Cuban Paradise – Old Town Escape the stress and cares of your daily life Built in 1917 as a “club”…

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• $228
  nightly
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Heather’s Villa

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Heather’s Villa – Old Town Upon entering, the living room features a super comfy queen sleeper sofa if you choose…

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• $188
  nightly
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Belle Fleur

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Belle Fleur – Old Town Amenities: Parking: One off-street spot reserved, on-street parking also available. Sleeping Arrangements: Restrictions: Smoking only…

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• $5500
  monthly
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La Bonne Vie

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• La Bonne Vie – Old Town Located only five blocks from infamous Duval St, this beautiful three story town home…

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• $5500
  monthly
• 
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Sunset Marina Paradise

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• Sunset Marina Paradise – Stock Island is just that – a sunset paradise! Each night tells a different story. Located…

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• $4500
  monthly
• 
  Compare

Key West Conch

• 3 Bedrooms, 1.5 Bathrooms, Sleeps 6
• Key West Conch – Old Town This grandiose historic home was built in the 1890′s and has been host to…

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• $3500
  monthly
• 
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Artists Retreat

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• Artists Retreat – Old Town This spacious and fully equipped unit is great for a vacationing family or small group…

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• $6500
  monthly
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Casa Familia

• 3 Bedrooms, 2 Bathrooms, Sleeps 4
• Casa Familia – Old Town Enjoy this wonderful historic home with recent renovations, perfectly placed pool, separate master suite and…

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• $5000
  monthly
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Casa Cayo Hueso

• 3 Bedrooms, 2 Bathrooms, Sleeps 8
• Casa Cayo Hueso – Old Town, which means “Key West House”, is a perfect example of shotgun architecture with a…

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• $3500
  monthly
• 
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Casa Dulce

• 3 Bedrooms, 2 Bathrooms, Sleeps 6
• Casa Dulce – Old Town This historic Conch House has been completely redesigned and custom crafted by 2 architects as…

• from
• $4000
  monthly
• 
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Maison du Soleil

• 2 Bedrooms, 2 Bathrooms, Sleeps 4
• Maison du Soliel – Old Town means House of Sun. Recently renovated this contemporary condo with sixteen windows is not…

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• $3200
  monthly
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Carey’s Cottage

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Carey’s Cottage – Old Town Located right next door to the Five Brothers Grocery (the best con leche and Cuban…

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• $4000
  monthly
• 
  Compare

Tropical Retreat

• 4 Bedrooms, 3 Bathrooms, Sleeps 8
• Tropical Retreat – Old Town Enjoy this wonderful historic home with recent renovations, perfectly placed pool, separate Pool House and…

• from
• $5000
  monthly
• 
  Compare

Olé Olivia!

• 4 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Olé Olivia! – Old Town You will be delighted with this wonderful home with recent renovations, perfectly placed pool, and…

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• $5500
  monthly
• 
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Simonton Court Historic Inn & Cottages

• 0 Bedroom, 0 Bathroom, Sleeps 0
• Located in 2 acres of lush tropical gardens, this elegant collection of cottages, manor house and town house is positively…

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• $145
  nightly
• 
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Bay Pointe in Key West Florida

• 3 Bedrooms, 3 Bathrooms, Sleeps 8
• Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of…

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• $3800
  monthly
• 
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Maison du Calais

• 3 Bedrooms, 2.5 Bathrooms, Sleeps 6
• Maison du Calais – Old Town Amenities: Heated Pool, Deck, Jacuzzi, Washer/Dryer, Dishwasher, DVD Player, High Speed Internet, Separate cottage…

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• $5000
  monthly
• 
  Compare

Lost Weekend

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Lost Weekend – Old Town is perfectly situated for the discriminating guest who wants to enjoy Key West at its…

• from
• $4500
  monthly
• 
  Compare

Elgin Hideaway

• 2 Bedrooms, 2 Bathrooms, Sleeps 4
• Elgin Hideaway – Old Town Enjoy this beautiful 2 story historic home, sunny pool, large open floor plan for entertaining…

• from
• $4000
  monthly
• 
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Yellow on White

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Yellow on White – Old Town Yellow on White is conveniently located next to a full spa to relax your…

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• Contact Owner
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• 0 Bedroom, 0 Bathroom, Sleeps 0

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Windsor Townhome #1

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Windsor Townhomes – Old Town Elegance and modern sophistication are apparent as you enter any one of these six newly…

• from
• $458
  nightly
• 
  Compare

Secret Courtyard Cottage

• 2 Bedrooms, 1 Bathroom, Sleeps 5
• Secret Courtyard Cottage -Old Town Welcome to a little piece of hidden paradise you never knew existed. Once you’re nestled…

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• $275
  nightly
• 
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Bella Vita

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Bella Vita – Old Town Located half a block from infamous Duval St, this beautiful 1 bedroom, one bathroom property…

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• $188
  nightly
• 
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Paradise Harbor Retreat

• 3 Bedrooms, 3 Bathrooms, Sleeps 6
• Paradise Harbor Retreat – Old Town This gorgeous four level home is a luxurious waterfront property. It is a spacious…

• from
• $550
  nightly
• 
  Compare

Red on White

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Red on White – Old Town Located in the heart of the White Street art district, just six blocks from…

• from
• $128
  nightly
• 
  Compare

Green on White

• 1 Bedroom, 1 Bathroom, Sleeps 3
• Green on White– Old Town Green on White is located just six short blocks from both Duval street and the…

• from
• $128
  nightly
• 
  Compare

Blue on White

• 1 Bedroom, 1 Bathroom, Sleeps 4
• Blue on White– Old Town Blue on White is located in the heart of the White Street art district, just…

• from
• $128
  nightly
• 
  Compare

Windsor Townhome #5

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…

• from
• $458
  nightly
• 
  Compare

Buena Vista

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Buena Vista – Old Town This wonderfully indulgent one bedroom cottage is on Center Street, just one-half block from Duval…

• from
• $178
  nightly
• 
  Compare

Windsor Townhome #3

• 3 Bedrooms, 3.5 Bathrooms, Sleeps 6
• Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in…

• from
• $458
  nightly
• 
  Compare

La Casa De Luces

• 1 Bedroom, 1 Bathroom, Sleeps 4
• La Casa De Luces – Old Town Come to relax or to play while enjoying the spectacular sunsets and the…

• from
• $168
  nightly
• 
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Heron Suite

• 1 Bedroom, 1 Bathroom, Sleeps 2
• Heron Suite– Old Town Tucked among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Heron Suite.…

• from
• $188
  nightly
• 
  Compare

Royal Escape

• 3 Bedrooms, 3 Bathrooms, Sleeps 10
• Royal Escape – Old Town If Cleopatra and Anthony had dreamed of a Key West hideaway this spacious three bedroom,…

• from
• $458
  nightly
• 
  Compare

Cuban Club Suite

• 2 Bedrooms, 2 Bathrooms, Sleeps 6
• Cuban Club Suite – Old Town Built in 1917 as a “club” for Cuban cigar makers and their families as…

• from
• $228
  nightly
• 
  Compare