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Vacation Rentals in Winter Park, Florida

about Winter Park

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Winter Park, 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 Winter Park are added and updated every week!

Compared to hotels, Winter Park 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.

Winter Park, Florida Vacation Rentals and Tourism

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

rental results

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Weekly rate:

Min $0, Max $4000

$0
$2,000
$4,000+

Bedrooms: Min 0, Max 5

0
5+







Property Type:


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

Villa Paradise - Luxurious,Lakefront,Pool/Spa,Shopping,Entertainment
Winter Park Villa Rental Picture
  • bedrooms 5
  • rental type Villa
  • owner badgeowner badge
  • sleeps 11
  • baths
  • rates (USD) $1,050 - $1,650 /nt
    $7,950 /wk
    $28,600 /mth
 
 
 
 
 

4 reviews write a review

Beautiful home in Winter Park, Steps from Park Ave., Shops Restaurants
Winter Park House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $395 /nt
    $2,000 /wk
    $5,000 /mth
 
 
 
 
 

5 reviews write a review

A Rare Jewel in the Heart of Winter Park, Steps to Park Ave or Rollins College
Winter Park House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $295 /nt
    $1,500 /wk
    $3,950 /mth
 
 
 
 
 

7 reviews write a review