Vacation Rentals & Villas in Winter Park

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1,393 villas

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 33 minutes

Price per night from

$115

The Mid-Century Modern Gem

Winter Park townhouse

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$184

HOME AWAY FROM HOME in beautiful Winter Park

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 15 minutes

Price per night from

$172

Stylish Boutique Guest House

Winter Park house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$229

Relaxing, lake-view home near Park Avenue

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$331

Great rentals within 20 miles that match your search

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. 2 hours 35 minutes

Price per night from

$139

Bargain Vacation Home near Disney

Kissimmee house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

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

Price per night from

$217

Disney for the Holidays! 3 Bedroom in Orlando

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$315

2-Bedroom Villa - Orlando

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$258

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$344

Wyndham Bonnet Creek Next Door to Disney

Orlando tower

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$229

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.

Price per night from

$408

DISNEY ORLANDO LAKE 4 BED LUXURY POOL VILLA

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

“Absolutely Super Home” What a wonderful surprise to find this home is so spacious, well kept, large and so accommodating. We needed nothing. Everything was included as far as amenities and appliances. This home is so comfortable and so well kept by a property company. They took care of the pool, yards and if we had any questions, they were more than happy to help. And that screened-in pool - WOW! Thank you so much to Brian and Irina. We never had to request for anything and they are so pleasant to deal with. We would recommend you stay there as you will definitely be pleased.

Price per night from

$161

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

Price per night from

$87

From $110/nt,4BR 1900sqft townhome,lake view,Near Disney,Seaworld,Convention Ctr

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 31 minutes

Price per night from

$126

Beautiful Large Studio Condo on the Lake

Orlando apartment

/ 1 bathroom / sleeps 4

Price per night from

$228

Wonderfull Villa in a luxury Resort

Orlando villa

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$344

Studio with a kitchen in Enclave Suites Orlando

Orlando hotel apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 10 minutes

Price per night from

$91

Orlando / Gated Golf Community / Ventura / 3 Bed/

Orlando townhouse

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$103

Beautiful 2 Bedroom Condo on the Lake

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$342

LUXURY Town Center Villa Disney Studio APT

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$198

Disney for the Holidays! 1-Bedroom Villa Orlando

Orlando apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$195

Price per night from

$336

ENHANCED CLEANING HERE! Great AMENITIES and SO MUCH MORE! 2BDRM Condo!!

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 8

“Another too short getaway at the awesome Reunion Resort!” Fantastic condo, spectacular resort, acceptable service, excellent on-site water park/lazy river. Through FlipKey the price was manageable. We had some problems confirming the reservation for a few weeks which was concerning and frustrating, but in the end everything worked out.

Responds fast! avg. 3 hours 23 minutes

Price per night from

$218

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. 3 hours 50 minutes

Price per night from

$212

Nice Furnished Vista Cay 3BD/3.5BA TownHome

Orlando hotel apartment

3 bedrooms / 4 bathrooms / sleeps 8

“Great Location, Clean and Spacious House” Very good location for SeaWorld and aquatica. New, clean, with plenty of space. Safe, gated community.

Responds fast! avg. 1 hour 33 minutes

Price per night from

$252

Blue Tree Resort

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$164

Luxury 3 Bedroom Lock-Off Condo in Orlando

Orlando private room

1 bedroom / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 40 minutes

Price per night from

$213

The Fountains Resort

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$887

Vacation in Orlando, Florida

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$294

Marriott's Cypress Harbor Resort

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$344

Fireworks on the 4th if July at Disney. Mickey is waiting for you.

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$352

Blue Tree Resort at Lake Buena Vista: 2-Bedrooms

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$212

Deluxe Studio at Disney's Saratoga at half price

Orlando apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$332

The Fountains (Bluegreen)

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 3 minutes

Price per night from

$229

Holiday Villa Orlando Florida

Orlando villa

4 bedrooms / 3 bathrooms / sleeps 9

“Great house” We had a wonderful time at the Orlando Villa! The house is lovely and very spacious. The pool is amazing and the neighborhood was quiet. It was just like staying at a friend's house. Raphael stopped by and was very sweet. We did not have any problems or complaints. Close to the parks and lots of stores nearby.

Responds fast! avg. 2 hours 42 minutes

Price per night from

$149

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