Vacation Rentals & Villas in Winter Park

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297 villas

2br - 1000ft2 - Winter Park House

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$115

Stylish Boutique Guest House

Winter Park house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$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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$91

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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$196

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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$101

*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. 43 minutes

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$115

Apartment in Lake buena vista resort village & spa

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$194

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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$109

House at disney Kissimmee

Kissimmee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$149

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$164

Marriott's Royal Palms Resort Orlando Near Disney

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$171

Cypress Pointe Resort Near Downtown Disney

Orlando apartment

  • 1 bedroom
  • 3 bathrooms
  • sleeps 8

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$214

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$295

Luxurious Penthouse

Vista Cay condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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$430

Between Disney and Seaworld 2 Bedroom Sleeps 8

International Drive condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$114

Ninovan on the Shore, A river retreat with history

Sanford house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

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$379

Gator Nest - Three-Bedroom Two Bath Lake View House

Oviedo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 11 minutes

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$235

Sleeps 8-12 HOUSE PRIVATE YARD/ POOL/SPA

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$203

Disney location vila with 4 poster bed, pool, wifi

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$158

Villa Linton - Beautiful Florida Home with Themed Bedrooms

Kissimmee villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Large home with easy access to Disney” This home was large enough for our whole family (7 adults) to sleep comfortably and it was so easy to get to the parks quickly before the crowds! Our adult children felt like kids again in the Scooby Doo room. The kitchen was large enough to cook family meals, and grocery stores are very nearby. Our only "wishes" while we were there were to have an outdoor grill and to have a TV in the family room large/loud enough for all of us to hear (the room was comfortable, though). We liked the gated community, but the streets are very narrow and with lots of parked cars, if you're driving a large vehicle you have to be very careful. The owner was superbly kind and quick with communicating. We'd definitely stay here again.

Responds fast! avg. 1 hour 34 minutes

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$164

LUXURY Lakes Villa Disney Studio APT

Orlando villa

  • 1 bathroom
  • sleeps 5

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$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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$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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$88

LUXURY Town Center Villa Disney Studio APT

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$199

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$336

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. 2 hours 12 minutes

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$213

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

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$217

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$287

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$344

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$229

4/3 Private Lakefront Town Home at Storey Lake Resort-Near Disney Theme Parks

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$206

Top Deluxe Apartment at Storey Lake (264415)

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$1,235

Dream Townhome with private pool close to disney SL4806

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

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$270

Beautiful Vacation Apartment (266641)

Pine Castle condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$135

Lovely Mickey Vacation Apartment (266626)

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$170

BEAUTIFUL VISTA CAY RESORT CONDO 2BD/2BA NEAR UNIVERSAL

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$161

Doorstep of Disney! 2-Bedroom Condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$276

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