Vacation Rentals & Villas in Winter Park

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1,280 villas

2br - 1000ft2 - Winter Park House

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$115

The Mid-Century Modern Gem

Winter Park townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$184

Stylish Boutique Guest House

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Relaxing, lake-view home near Park Avenue

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$331

Great rentals within 20 miles that match your search

Bonnet Creek Resort ツ 1BR SLEEPS 4 Wyndham Orlando Condo Rental!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$91

Disney's Saratoga Springs Resort and Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$574

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Price per night from

$171

Wyndham Bonnet Creek Resort

Orlando hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 53 minutes

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Price per night from

$339

Ocean Front Boardwalk Property

Wildwood studio

  • Studio
  • 2 bathrooms
  • sleeps 8

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Price per night from

$459

beautiful 3 bedroom has room for all

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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Price per night from

$311

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$631

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$345

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$152

1 Week Rental in Orlando, FL 2 Bdm Deluxe Villa Close to Theme Parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$197

Wyndham Bonnet Creek Florida at Disney

Buena Ventura Lakes condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$101

Responds fast! avg. 30 minutes

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$114

1-bedroom / 1-bath Sleeps 4 in Orlando - 1 week

Williamsburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$99

Marriott's Sabal Palms

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$459

2br - 2200ft2 - Beautiful one story 2 bed/3bath

Orlando house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$361

$1250+fees sleep 6, available Dec 24-Dec 31, 2022 Resort Fantasy World II

Kissimmee villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$194

Vistana Rental Lake Buena Vista FL

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$295

The Vue at Downtown Orlando

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$138

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$322

Runaway Beach Club Resort 2 Bedroom Vacation Condo (RW3101)

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$207

Runaway Beach Club Resort 2 Bedroom Vacation Condo (RW8103)

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 59 minutes

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Price per night from

$207

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

LUXURY Lakes Villa Disney Studio APT

Orlando villa

  • 1 bathroom
  • sleeps 5

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Price per night from

$192

Vista Cay Luxury Condo 3 bed/2 bath (#3030)

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect for large families” I have stayed in Vizta Cay many times before, but through a different leasing agency. I must say, this time I was highly impressed with the unit as well as all the items that were included and made our stay so nice and relaxing will be sure to book with you guys again.

Responds fast! avg. 53 minutes

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Price per night from

$598

Vista Cay Luxury 3 bedroom condo #3066

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Love Vista Cay” I have stayed at a Vusta Cay resort 3 times. I'm never disappointed in how the places are so clean nicely decorated. If available they will always be my 1st choice. The only thing I was disappointed in was the cable. It did not have a variety of channels and the signal did not work for every channel.

Responds fast! avg. 53 minutes

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Price per night from

$665

Westgate Lakes, Orlando Florida - 4 Bedroom Villa - Huge Resort with everything

Orlando hotel apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

“Worth It!!!” Our family stayed at Westgate Lakes for one week during Spring Break. We had a four bedroom condo and the space was fabulous!!! We were more than impressed with the resort staff and all the ammenities. The location was also very excellent and so easy to find and so close to the attractions we wanted to visited. The resort was very clean in all areas and very safe and secure for our family.

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Price per night from

$409

Lakefront Townhouse 5 Star LOCATION

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Lakefront Townhouse Review” Centrally located to everything. Place very clean and well kept.Enjoyed our stay there and would recommend the place to anyone. The agent was very helpful and polite. We are going back in 2011.

Responds fast! avg. 36 minutes

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Price per night from

$109

Elegant Modern Condo/Apt. in Sunny Orlando !

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic Vacation in Orlando” Thanks to Jan we probably had the best vacation in years. The condo is very well situated. It’s only a five minute drive from restaurants and supermarkets, such as Aldi and WalMart. For us it was very important since we have two kids and love to taste local food and cook in. The kitchen is equipped with high class appliances and well stocked with everything you need for cooking. Needless to say, the condo is kept impeccably clean and spotless. We were also impressed by the overall design of the condo and the furniture. Having two bathrooms was an additional plus. The master bathroom with its expensive marble counter top and tiled with natural stone, seemed to have come out from an upscale designer office. The pool located only a few steps away from our porch was a little jewel. It was never crowded and on most times we had it only to ourselves. The gated community is located in a well-kept prestigious area and its admin personnel helped us a lot in planning our visits to the amusement park, printing tickets, etc. Jan is a very friendly person, going out of his way to make our stay at the condo enjoyable. His professionalism in running the condo and his attention to detail is fantastic. The condo definitely exceeded all my expectations. We’d love to return to Jan’s place once again and probably enjoy a longer stay there. Alexander & Natalya D., Yekaterinburg, Russia

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Price per night from

$88

Beautiful Large Studio Condo on the Lake

Orlando apartment

  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Studio with a kitchen in Enclave Suites Orlando

Orlando hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 8 minutes

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Price per night from

$91

Orlando / Gated Golf Community / Ventura / 3 Bed/

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$96

Orlando / Gated Golf Community / Ventura / 3 Bed/

Orlando townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$135

Beautiful 2 Bedroom Condo on the Lake

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$343

Viewing 38 of 1,280
rentals in Winter Park

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