Key West Vacation Rentals

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Available Thanksgiving - Key West Ocean Side Luxury w/ High Speed Internet

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 174861
Key West condo rental - Overhead view of 1800 Atlantic pool & beach
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$1,050/week
 
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Luxurious 2 bedroom/2.5 bath home located in Old Town Truman Annex

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 220663
Key West townhome rental - Spacious Kitchen and Dining area
2 Bedrooms, Sleeps 4
  • Townhome
  • 2 Bathrooms, 1 Half Bath
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$1,600 - $2,500/week
$4,500 - $7,000/month
 
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Villa Soleil, Elegant Truman Annex condo in Old Town Key West

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 188516
Key West condo rental - Villa Soleil
2 Bedrooms, Sleeps 4
  • Condo
  • 1 Bathroom
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$1,200 - $2,000/week
 
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Villa Fleur, Elegant Truman Annex condo in the heart of Old Town

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 207098
Key West condo rental - Living Room
2 Bedrooms, Sleeps 4
  • Condo
  • 1 Bathroom
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$1,200 - $1,800/week
 
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A Touch of Bermuda at Truman Annex

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 102572
Key West cottage rental - Welcome to our front door
2 Bedrooms, Sleeps 6
  • Cottage
  • 2 Bathrooms
  • near the ocean, town
  • accept credit card
Rates per property (USD)
$2,000 - $2,100/week
 
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Luxury Condo-Walk to Beach/Duval St. Reduced Till Dec 14

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 203228
Key West condo rental - Living Room open to the Dining area and Kitchen.
2 Bedrooms, Sleeps 5
  • Condo
  • 1 Bathroom
  • beach, downtown
  • swimming pool
Rates per property (USD)
$1,100 - $1,600/week
 
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Key West's Sunset Marina Ocean Front Condo

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 204628
Key West condo rental - Sunset picture taken from balcony of Condo
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • waterfront
  • swimming pool
 
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Key West - Poolside Conch Paradise at Key West Golf Club

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 164920
Key West townhome rental - Front view from the street
2 Bedrooms, Sleeps 4
  • Townhome
  • 1 Bathroom, 1 Half Bath
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$1,250 - $2,450/week
$2,450 - $4,000/month
 
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Ocean Front Condo at 1800 Atlantic - Next to Smathers Beach

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 174733
Key West condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per person (USD)
$1,750 - $2,750/week
$2,950 - $5,950/month
 
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Truman Annex Shipyard Condo, Old Town Key West

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 172414
Key West condo rental - Living Area
2 Bedrooms, Sleeps 4
  • Condo
  • 2 Bathrooms
  • downtown, near the ocean
  • swimming pool
Rates per property (USD)
$2,000/week
 
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Campbell Courtyard Townhouse 'In the Sky'

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 167721
Key West townhome rental - Large, Heated Pool in Lush Tropical Setting
2 Bedrooms, Sleeps 6
  • Townhome
  • 2 Bathrooms, 1 Half Bath
  • downtown
  • accept credit card
Rates per property (USD)
$3,500 - $5,500/month
 
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Hurricane's Rebellion - a Key West Vacation Condo

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 185408
Key West condo rental - Exterior View
2 Bedrooms, Sleeps 6
  • Condo
  • 1 Bathroom
  • near the ocean
  • accept credit card
Rates per property (USD)
$1,200 - $1,800/week
 
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Henry's Penthouse on the Ocean in Key West (weekly / nightly rentals)

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 112032
Key West condo rental - Ahhh - the pool (heated) with ocean in background
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, waterfront
  • accept credit card
 
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Fully Equipped Condo in the Heart of Beautiful Key West

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 162533
Key West condo rental - Front porch
2 Bedrooms, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach
  • swimming pool
 
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Villa Soleil-Enjoy America's Caribbean with Style and Comfort

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 141421
Key West townhome rental - Truman Annex Gated Community
2 Bedrooms, Sleeps 6
  • Townhome
  • 2 Bathrooms, 1 Half Bath
  • near the ocean, town
  • accept credit card
 
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Truman Annex - Foundry Townhouse - One of a Kind!

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 200634
Key West townhome rental - Townhouse Exterior and Garden
2 Bedrooms, Sleeps 4
  • Townhome
  • 2 Bathrooms, 1 Half Bath
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$1,800 - $2,250/week
 
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Live Like a 'Resident Conch' at the Key West Golf Club

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 314751
Key West townhome rental
2 Bedrooms, Sleeps 6
  • Townhome
  • 2 Bathrooms, 1 Half Bath
  • near the ocean
  • swimming pool
 
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Modern Oceanside Living

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 204379
Key West condo rental - The beach leading to the pool and courtyard
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • town, waterfront
  • swimming pool
Rates per property (USD)
$2,100 - $3,000/week
 
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SPECIAL OFFER! December Rate Specials (December 20 - December 29)

Villa Nomade, Elegant Truman Annex condo in the heart of Old Town

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 158403
Key West condo rental - Garden
2 Bedrooms, Sleeps 4
  • Condo
  • 1 Bathroom
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$1,200 - $2,000/week
 
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Special Offer

Key West Truman Annex

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 212518
Key West townhome rental - Key West
2 Bedrooms, Sleeps 6
  • Townhome
  • 1 Bathroom, 1 Half Bath
  • downtown, near the ocean
  • swimming pool
 
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Truman Annex - Two-Story Shipyard Cottage

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 212151
Key West condo rental - Street View
2 Bedrooms, Sleeps 5
  • Condo
  • 2 Bathrooms
  • beach, downtown
  • swimming pool
Rates per property (USD)
$1,300 - $1,900/week
$3,500 - $6,000/month
 
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Beautiful Duval St. Condo, Location, Location!!!!

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 156723
Key West condo rental - Living room
2 Bedrooms, Sleeps 4
  • Condo
  • 1 Bathroom
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$200 - $275/night
$1,000 - $1,500/week
$4,000 - $5,000/month
 
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'Old Town Oasis' @ Truman Annex: Spacious 2 BR Oceanfront Condo

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 181289
Key West condo rental - Your own personal poolside sunset, no crowding.
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • downtown, waterfront
  • accept credit card
Rates per property (USD)
$3,300 - $5,000/week
$8,800 - $12,000/month
 
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Henry's Piece Of Paradise On The Ocean In Key West (nightly / weekly)

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 103905
Key West condo rental - Ahhh - The pool (heated) with ocean in background
2 Bedrooms, Sleeps 5
  • Condo
  • 2 Bathrooms
  • beach, waterfront
  • accept credit card
 
Contact the Owner
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Key West Luxury - Tropical Home

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 181296
Key West house rental - Welcome to your tropical paradise!
2 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms
  • downtown, near the ocean
  • accept credit card
 
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Secret Garden in Key West

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 168086
Key West condo rental
2 Bedrooms, Sleeps 4
  • Condo
  • 1 Bathroom
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$1,100 - $2,100/week
 
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Fantasy Fest discount** Supermodel Vacation Rental

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 210467
Key West townhome rental - Front Entry
2 Bedrooms, Sleeps 5
  • Townhome
  • 2 Bathrooms
  • swimming pool
  • air-conditioning
Rates per property (USD)
$2,600 - $3,200/week
$4,800 - $6,200/month
 
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Key West Paradise On The Ocean

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 210496
Key West condo rental - Beautiful Heated Pool With Ocean in Background
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, waterfront
  • accept credit card
Rates per property (USD)
$3,500 - $6,000/month
 
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Truman Annex, Old Town, Key West, Private Setting with Luxury Features

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 123714
Key West house rental - Front Entrance
2 Bedrooms, Sleeps 6
  • House
  • 2 Bathrooms, 1 Half Bath
  • downtown, resort
  • swimming pool
 
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Key West Luxury 2 Bedroom Condo in The Shipyard of Truman Annex in Old Town

  1. Florida Keys,
  2. Lower Florida Keys,
  3. Key West Vacation Rentals
— Property 208697
Key West condo rental - Outside View 1
2 Bedrooms, Sleeps 6
  • Condo
  • 1 Bathroom
  • downtown, near the ocean
  • accept credit card
Rates per property (USD)
$1,200 - $1,800/week
 
Contact the Owner
View Property Details
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