Vacation Rentals & Villas in Winter Park

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655 villas

Stylish Boutique Guest House

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

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

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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

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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Price per night from

$114

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

LUXURY Lakes Villa Disney Studio APT

Orlando villa

  • 1 bathroom
  • sleeps 5

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Price per night from

$192

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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$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

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

LUXURY Town Center Villa Disney Studio APT

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$199

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Price per night from

$337

Luxury Condo at Hotel prices - Isles of Cay Commons

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Lots of space, great amenities” We loved the location, ease of access and close to Publix which is part of the resort design. The only food at the resort mall we would recommend is Publix and Subway - Beth's burgers is overpriced, low quality. We did not love the neighbors up stairs who never seemed to stop dragging chairs across the floors or slamming their doors nor the neighbor downstairs who sported a smokers cough on the balcony every day nearly all day with his constant smoking from 7am until well after midnight. We were forced to spray the unit each time we returned due to the smell of cigarette smoke that seemed to find its way into the condo each day. The downstairs neighbors dog barked one day nearly all day - we love dogs but do not believe they should be left on the balcony for the entire day alone. The condo is very spacious, beds are comfortable, kitchen is well appointed with full size appliances and a full size washer and dryer which is always appreciated on vacations. The 2 BR are very large - 1 with a large shower stall and the other a tub unit. Each bedroom had a TV, large closet and night stand however there is no dresser/chest of drawers for clothing storage so we suggest taking extra hangers as we did. There is a laundry basket, iron, pool towels, 2 lounge chairs, etc. for use in the unit. The refrigerator has an ice maker in the door with water. The kitchen is spacious with all necessary amenities as well as ample dishes, cookware, etc. Plenty of parking, elevators and steps straight to the condo. This particular unit was in a separate area from the main resort which allowed us to have a nice quiet pool experience while we enjoyed the hot tub frequently alone. There was rarely more than 10 people at the pool at any one time. This is a big bonus for us, we never enjoy huge crowds. This condo overlooks the lake south of the Orange County Convention Center and across from Sea World - you can see the roller coasters run. Unfortunately they seem to be building a road across the lake just next to the resort which I am sure will increase the road noise; not a welcome addition in my perspective. We chose this location for the decreased noise and excellent location near Universal and John Young Parkway. We would recommend Azteca restaurant about 5 miles east for dinner off the tourist area. The only drawback for this condo is the neighbors - IF you are fortunate enough to get considerate neighbors then the experience should be great. Sadly many people tend to forget to show consideration for those around them - spitting from the 4th floor, continuous cig smoke, throwing cig. butts off the balcony's and partying way into the night are not enjoyable experiences for us.

Responds fast! avg. 17 minutes

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Price per night from

$213

Bargain Vacation Home near Disney

Kissimmee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$121

Great Resort Villa next to SeaWorld and near Disney & Universal Studios

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$217

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$287

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Price per night from

$257

*CLEAN - Afforable Townhome - 5 Miles from Disney*

Kissimmee townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Exceptional” This place was beautiful... I’ve always booked hotel rooms when I go on vacations but never again will I book a hotel... this place had everything I could ask for and more my family and I were very pleased and satisfied.

Responds fast! avg. 39 minutes

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Price per night from

$115

1 week Westgate Resort Studio in Orlando_Sleeps 4

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$107

Apartment in Lake buena vista resort village & spa

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$194

WESTGATE LAKES RESORT & SPA-Orlando Florida

Orlando villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 55 minutes

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Price per night from

$217

Studio with an amazing terrace

International Drive hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 8 minutes

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Price per night from

$109

House at disney Kissimmee

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$150

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Price per night from

$165

Marriott's Royal Palms Resort Orlando Near Disney

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$171

Cypress Pointe Resort Near Downtown Disney

Orlando apartment

  • 1 bedroom
  • 3 bathrooms
  • sleeps 8

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Price per night from

$214

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$295

Luxurious Penthouse

Vista Cay condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$431

WESTGATE LAKES RESORT & SPA-Orlando Studio

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 55 minutes

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Price per night from

$129

Gator Nest - Three-Bedroom Two Bath Lake View House

Oviedo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$236

Sleeps 8-12 HOUSE PRIVATE YARD/ POOL/SPA

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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Price per night from

$204

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