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Sailing Vacation Rentals Home Page | Vacation Rentals Home Page | Last updated: Wednesday, April 23, 2014
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Florida Keys Sailing Vacation Rentals


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

Cottages with FREE 22' sailboats, kayak adventures, canoes, snorkel gear, fishing gear, bicycles, and sunset cruises. Property 100701
  • Key Largo
  • Cottage
  • Varies bedrooms
  • Sleeps 40+
  • Varies bathrooms
Remodeled Ocean View Condo Property 99374
  • Islamorada
  • Condo
  • 2 bedrooms
  • Sleeps 6
  • 2 bathrooms
Ocean front condo with panoramic views Property 99373
  • Islamorada
  • Condo
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
LittleTorch Key 3 Bedroom House Property 98675
  • Little Torch Key
  • Villa
  • 3 bedrooms
  • Sleeps 6
  • 2.5 bathrooms
Margarita Villa 2 Bedroom Villa - Dock Your Boat - Waterfront Florida Keys Home Property 98674
  • Summerland Key
  • Villa
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
BIG PINE KEY VACATION HOME WITH BOAT LAUNCH AREA Property 98673
  • Big Pine Key
  • House
  • 5 bedrooms
  • Sleeps 10
  • 2 bathrooms
Big Pine Key 3 Bedroom Vacation Rental Property 98672
  • Big Pine Key
  • Townhouse
  • 3 bedrooms
  • Sleeps 6
  • 1 bathrooms
BIG PINE KEY VACATION RENTALS Property 98671
  • Big Pine Key
  • Duplex
  • 2 bedrooms
  • Sleeps 4
  • 1.5 bathrooms
Sugarloaf Key 5 Bedroom Home Property 98670
  • Sugarloaf Key
  • House
  • 5 bedrooms
  • Sleeps 10
  • 5 bathrooms
Marina View Key Largo Vacation Rental Property 92844
  • Key Largo
  • Townhouse
  • 3 bedrooms
  • Sleeps 8
  • 3 bathrooms
Key Largo Family Vacation Rental - Affordable Property 92843
  • Key Largo
  • Condo
  • 2 bedrooms
  • Sleeps 6
  • 2 bathrooms
Romantic Private Tropical Island Home with boat included Property 92220
  • Marathon
  • House
  • 2 bedrooms
  • Sleeps 4
  • 2 bathrooms
  • September - December Non-Holiday
    3795

  • Holidays Call for Rates
    4995



Beautiful Bayfront Home Property 88546
  • Islamorada
  • House
  • 3 bedrooms
  • Sleeps 8
  • 3 bathrooms
  • Summer Months (May-Aug)
    $6500 per month

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



All You Need in this Newly Built Canal Front Vacation Home! Property 88545
  • TAVERNIER
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
  • High Season (Dec-April)
    $4950/month

  • Summer Season (May-Aug)
    $4950/month



Phenomenal Open Water Views Property 88544
  • Tavernier
  • House
  • 4 bedrooms
  • Sleeps 10-12
  • 3 bathrooms
  • Value Season (Sep-Nov)
    $6,500

  • High Season 2014 (Dec-April)
    $8,250



Ocean Front Complex Property 88543
  • Islamorada
  • Condo
  • 2 bedrooms
  • Sleeps 4
  • 2 bathrooms
  • Value Season (Sept-Nov)
    $2200 per month

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



A piece of paradise! Property 88542
  • Islamorada
  • House
  • 1 bedrooms
  • Sleeps 2
  • 1.5 bathrooms
  • High Season (Dec-April)
    $3850 per month, $1235 per week



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



Spacious Ocean Front Home with Expansive Views Property 88540
  • Key Largo
  • House
  • 5 bedrooms
  • Sleeps 10-12
  • 5 bathrooms
  • Summer Season (May-Aug)
    $18,000/month

  • Value Season (Sep-Nov)
    $16,5000



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



Ocean Front Condo Complex - Great Ocean Views from Balcony Property 88538
  • Islamorada
  • Condo
  • 2 bedrooms
  • Sleeps 6
  • 2 bathrooms
BEAUTIFUL CANAL FRONT STILT HOME WITH HEATED POOL Property 88535
  • Tavernier
  • House
  • 3 bedrooms
  • Sleeps 6
  • 2 bathrooms
  • Summer Season (May-Aug)
    $4400/month

  • Value Season (Sep-Nov)
    $4000/month



Luxurious Mariners Club 3 Bedroom Condo Property 88227
  • Key Largo
  • Condo
  • 3 bedrooms
  • Sleeps 6
  • 2.5 bathrooms
TRUMAN ANNEX 2 BEDROOM VACATION RENTAL - KEY WEST Property 88225
  • Key West
  • Townhouse
  • 2 bedrooms
  • Sleeps 6
  • 3 bathrooms
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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