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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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Winter Park things to do


River Ventures

I was visiting family in Tampa and seeing a manatee was on my bucket list for the trip. My aunt found River Ventures and we took the 9:15am tour on a more


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


Fleet Peeples Park

I love this park so much! I live about 25 minutes away and try to take my pup at least once a week to get all his energy drained! Of course he's a hyper more


Enzian Theater

If you're an independent film fan the Enzian is the place for you! With just one single screen room, Enzian is able to provide a movie experience like more


Orlando Power Yoga

After visiting several studios is the area this studio by far has the some of the most passionate instructors, and they make it fun for beginners more


Morse Museum Of American Art

Wow, this was a spectacular visit, much more than I was expecting. There are something like 24 rooms here, and they're not just all about lamps and 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


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


Baldwin Park

Baldwin Park is so beautiful! The park itself is pretty small but is very close to lots of cute shops and good restaurants. I love this area for 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

Kyle and the gang are great! The staff is knowledgeable and friendly. They also have a great Thursday night bike ride! Would definitely recommend them!read 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


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


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

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

Atlantis Cinnamon Beach, 11 Bedrooms, 14 HDTVs, Pool, Spa, Elevator, Theater
Winter Park House Rental Picture
  • bedrooms 11
  • rental type House
  • sleeps 24
  • baths 10
  • rates (USD) $1,500 - $1,583 /nt
    $4,000 - $10,786 /wk
    $21,214 - $47,000 /mth

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) $174 - $249 /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) $1,250 - $1,650 /nt
    $8,350 /wk
    $32,000 /mth

4 reviews write a review

Steps to Park Ave, Shops, Restaurants, 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