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Florida Keys Sailing Vacation Rentals


Cities in Florida Keys:   Anglers Park | Big Pine Key | Cudjoe Key | Duck Key | Grassy Key | Islamorada | Key Colony Beach | Key Largo | Key West | Little Torch Key | Long Key | Lower Sugarloaf Key | Marathon | Plantation Key | Ramrod Key | Sugarloaf Key | Summerland Key | Tavernier

Marina View Key Largo Vacation Rental Property 92844
  • Key Largo
  • Townhouse
  • 3 bedrooms
  • Sleeps 8
  • 3 bathrooms
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Key Largo Family Vacation Rental - Affordable Property 92843
  • Key Largo
  • Condo
  • 2 bedrooms
  • Sleeps 6
  • 2 bathrooms
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Beautiful Bayfront Home Property 88546
  • Islamorada
  • House
  • 3 bedrooms
  • Sleeps 8
  • 3 bathrooms
Rates Show More Rates
  • Summer Months (May-Aug)
    $6500 per month

  • Value Season (Sept-Nov)
    $5500 per month


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Phenomenal Open Water Views Property 88544
  • Tavernier
  • House
  • 4 bedrooms
  • Sleeps 10-12
  • 3 bathrooms
Rates Show More Rates
  • Summer Season (May-Aug)
    $7250

  • Value Season (Sep-Nov)
    $6000


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Ocean front condo Property 88543
  • Islamorada
  • Condo
  • 2 bedrooms
  • Sleeps 5
  • 2 bathrooms
Rates Show More Rates
  • Value Season (Sept-Nov)
    $2200 per month

  • Summer Months (May-Aug)
    $2800 per month


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A piece of paradise! Property 88542
  • Islamorada
  • House
  • 1 bedrooms
  • Sleeps 2
  • 1.5 bathrooms
Rates Show More Rates
  • All Other Seasons
    $3650 per month, $1125 per week


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2 bedroom condo in beautiful oceanfront complex Property 88541
  • Islamorada
  • Condo
  • 2 bedrooms
  • Sleeps 4
  • 2 bathrooms
Rates Show More Rates
  • All Other Months
    $4000 per month


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Exceptional 3 story townhouse Property 88539
  • Key Largo
  • Townhouse
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • All Other Months
    $3200 per month


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Lovely 3 bedroom, 2 bath condo Property 88537
  • Tavernier
  • Condo
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
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Elegantly Furnished Canal Home Property 88535
  • Tavernier
  • House
  • 3 bedrooms
  • Sleeps 8
  • 2 bathrooms
Rates Show More Rates
  • Value Season (Sep-Nov)
    $3800/month

  • Summer Season (May-Aug)
    $4200/month


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Luxurious Mariners Club 3 Bedroom Condo Property 88227
  • Key Largo
  • Condo
  • 3 bedrooms
  • Sleeps 6
  • 2.5 bathrooms
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TRUMAN ANNEX 2 BEDROOM VACATION RENTAL - KEY WEST Property 88225
  • Key West
  • Townhouse
  • 2 bedrooms
  • Sleeps 6
  • 3 bathrooms
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KEY WEST VACATION HOME - 1 BLOCK TO DUVALL STREET Property 88224
  • Key West
  • House
  • 2 bedrooms
  • Sleeps 6
  • 2.5 bathrooms
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Sit back and relax in this delightful home, situated on the open water. Property 87710
  • Ramrod Key
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • May thru November
    5000


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This ocean front masterpiece was created for those who only want the very best. Property 87709
  • Summerland Key
  • House
  • 4 bedrooms
  • Sleeps 8
  • 3 bathrooms
Rates Show More Rates
  • May - November
    6,900


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The Coral House is a prime destination spot for a great Florida Keys vacation! Property 87708
  • Ramrod Key
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • May thru November
    3000


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This Summerland Key vacation home is situated on a private, fully fenced lot Property 87707
  • Summerland Key
  • House
  • 2 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • May thru November
    2800


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Whatever your pleasure, the protective 75' seawall and clear, clean deepwater boating canal offers excellent choices! Property 87706
  • Big Pine Key
  • House
  • 2 bedrooms
  • Sleeps 4
  • 2 bathrooms
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Sit back and relax in this clean, airy, and spacious vacation home. Property 87705
  • Summerland Key
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates


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Come and enjoy the easy life when you select this wonderful vacation home Property 87704
  • Big Pine Key
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • December thru April
    3900


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Simple and sweet with no muss, no fuss. Property 87703
  • Big Pine Key
  • House
  • 2 bedrooms
  • Sleeps 4
  • 2 bathrooms
Rates Show More Rates
  • December thru April
    2300


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A tranquil oasis is your destination at Ocean Magic! Property 87702
  • Summerland Key
  • House
  • 5 bedrooms
  • Sleeps 10
  • 5 bathrooms
Rates Show More Rates
  • May thru November
    13,500 monthly


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This great Vacation Home is conveniently located on Cudjoe Key Property 87701
  • Cudjoe Key
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • December thru April
    2,900 monthly


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Kick back and relax in this Island vacation home Property 87700
  • Cudjoe Key
  • House
  • 2 bedrooms
  • Sleeps 4
  • 1 bathrooms
Rates Show More Rates
  • December thru April
    2200


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Snug Harbor is located on Summerland Key at mile marker 25 Property 87699
  • Summerland Key
  • House
  • 2 bedrooms
  • Sleeps 6
  • 2 bathrooms
Rates Show More Rates
  • May thru November
    2950


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