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Vacation Rentals in Windley Key, Florida

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about Windley Key

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Windley Key, Florida vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Windley Key are added and updated every week!

Compared to hotels, Windley Key vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Windley Key, Florida Vacation Rentals and Tourism

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Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Oceanfront at Anglers Reef, Steps From Pool and Ocean, Ocean View From All Sides
Windley Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 6
  • baths
  • rates (USD) $2,700 /wk
    $7,500 /mth
 
 
 
 
 

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Anglers Reef Resort Paradise in the Fl.Keys
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,575 - $2,100 /wk
 
 
 
 
 

12 reviews write a review

Luxury Waterfront Tropical Sunset Paradise
Windley Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 10
  • baths 5
  • rates (USD) $990 - $1,000 /nt
    $28,000 /mth
 
 
 
 
 

3 reviews write a review

Anglers Reef, Boat Slips, Heated Pool, Oceanfront, Tommy Bahama Furniture
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $1,995 /wk
    $5,995 /mth
 
 
 
 
 

4 reviews write a review

Islamorada – Simply Beautiful w/ Free Wifi, Hi-Def TV, & Many Extras; Top Rated
Windley Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $200 - $225 /nt
    $1,400 /wk
    $4,200 /mth
 
 
 
 
 

12 reviews write a review

Super Penthouse - Futura Yahct Club #603
Windley Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $995 - $1,395 /wk
 
 
 
 
 

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Upscale Family Friendly Gated Community - Oceanside Paradise
Windley Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $1,995 /wk
    $6,000 /mth
 
 
 
 
 

10 reviews write a review

Enjoy Sunrise By The Seashore! Luxuriously Appointed Sanctuary In Angler's Reef
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 5
  • baths
  • rates (USD) $1,800 - $2,100 /wk
 
 
 
 
 

10 reviews write a review

Venetian Waterfront Retreat Guaranteed Best Deal
Windley Key House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $6,500 /mth
 
 
 
 
 

2 reviews write a review

Spacious Islamorada Condo/town Home
Windley Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,250 - $3,750 /mth
 
 
 
 
 

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Boat, Fish, Swim from Your Own Dock! Vr-003
Windley Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

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Luxurious Home at Anglers Reef Oceanfront Resort with own Boat Slip
Windley Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $1,800 - $1,950 /wk
    $4,000 - $5,000 /mth
 
 
 
 
 

26 reviews write a review

Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS
Windley Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD)
 
 
 
 
 

24 reviews write a review

Your Florida Keys Getaway.....
Windley Key Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 8
  • baths 4
  • rates (USD)
 
 
 
 
 

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip
Windley Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $2,450 /wk
    $7,000 /mth
 
 
 
 
 

2 reviews write a review