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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.

Winter Park things to do


Harry P Leu Gardens

I have visited Leu Gardens many times over the years (including several weddings). This year for the first time we decided to buy the family membership more


Enzian Theater

This is one of Orlando's finest gems. I can't say enough good things about this theater. -Beautiful outdoor patio/bar with a decent beer and more


Fleet Peeples Park

Here is a video I put together highlighting this park: This is hands-down one of the best dog parks I have been to since more


Lake Eola Park

I love Lake Eola Park. I've done a few volunteer activities there as well as visited on my own and I love it every time. The atmosphere is quaint more


Orlando Power Yoga

The only thing positive about this studio is that your body feels detoxed from all the sweat pouring from your body once you leave (this coming from more


Morse Museum Of American Art

I love museums and the Morse doesn't disappoint. On my first visit I took the advice of the ladies working at the desk and watched the short film about more


Full Circle Yoga

Full Circle Yoga is a fantastic yoga studio. The facility itself is top-notch, featuring two beautifully maintained and spacious rooms - one fit more


The Yoga Shala

The Shala located in the middle of Orlando in a Winter Park neighborhood is where Ashtanga yogis and yoginis come to practice Mysore or take led more


Kyle's Bike Shop

This is my go to place! Honest, genuine, and most of all, technically competent. Had a bike built here after I ordered the parts and they got it done in more


Baldwin Park

Baldwin Park is a very nice area. Another one of the cool areas where you can grab a bite to eat, a drink with friends or simply hang out along the more


Amway Center

I went to Amway twice in two days. I had a great time both times. The first day I went, I seen the Orlando Magic play the NY Nets. One of my friends more


Boom-Art by Rogers Studio

I love coming here and wondering around looking at all the unique items. The owner, Glen Rogers and his wife are a former clowns and Glen will tell more


Albin Polasek Museum & Sculpture Gardens

I had to complete an Essay for my humanities class and decided on this museum because it is my professors favorite! Needless to say that I LOVED it! more


Crane's Roost Park

Attended XL 106.7's Red, Hot and Boom on July 3rd. This is annual event and obviously really popular, so the park was very busy! The park is huge more


Lake Lily Park

This is a very nice park. Wide sidewalks and at night it is very well lit. I enjoy taking my dog here and walking around the lake. He enjoys more

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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

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

7 reviews write a review

Lakefront Paradise Guest Apartment Winter Springs Oviedo Short Term Rental
Winter Park Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $179 /nt
    $1,113 /wk
    $3,210 /mth

10 reviews write a review

Luxurious,Lakefront,Pool/Spa,Shopping,Entertainment,Thyme Parks,Disney,Golf
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
    $30,300 /mth

4 reviews write a review

Atlantis Cinnamon Beach, 11 Bedrooms, 14 HDTVs, Pool, Spa, Theater, Elevator
Winter Park House Rental Picture
  • bedrooms 11
  • rental type House
  • sleeps 24
  • baths 11
  • rates (USD) $1,714 - $2,500 /nt
    $9,400 - $9,500 /wk
    $20,757 - $28,000 /mth

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