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Vacation Rentals & Villas in Winter Park

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1,340 villas

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 37 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. 16 minutes

Price per night from

$172

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 32 minutes

Price per night from

$145

LUXURY Lakes Villa Disney Studio APT

Orlando villa

/ 1 bathroom / sleeps 5

Price per night from

$192

2 Bedroom Deluxe Suite @ Blue Tree Resort

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$180

Warm and Inviting. Ideally located, 3BR/2BA Home

Maitland house

3 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

Awesome 4 Bedroom Gated Condo with only minutes to the Disney area

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

“Excellent stay” Great location, Close to outlet stores and wall mart. Lots of things to do around there, Will stay there again, with owners permission. THANK YOU Esmeralda Vicent.

Price per night from

$114

Luxurious

Orlando apartment

3 bedrooms / 4 bathrooms / sleeps 8

“Absolutly Wonderful!” Best value, best decor, most room for the $ Would have had to pay 3x more for a resort suite of the same size!

Responds fast! avg. 3 hours 46 minutes

Price per night from

$228

Villa Bella Vista Cay Penthouse/Lakefront Condo Overlooking the Pool & Lake Cay

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Villa Bella at Vista Cay is the Best! Enjoy your stay!” Just returned from a wonderful week long stay at this unit at the Vista Cay Resort! The condo is spacious, luxurious, and very comfortable. The pictures do not do this lovely space justice. Everything is better than expected. And clean as can be! From beginning to end, the owner, Bill, made this vacation a great experience. Bill's quick response to my initial inquiry, his professional manner during booking, and his call during our stay, asking if all was well, were much appreciated. From the time you step foot on the resort property, you will experience what a vacation should be like; restful, relaxing, and happy. Check-in was a breeze at the wonderful clubhouse, where the game room, theatre, exercise room, sundry/gift shop, and business office suite is located. All the staff were pleasant and very accommodating. We did have two small problems, a broken coffee maker and a front door that wouldn't lock. One call to the front desk and the coffee maker was replaced with a brand new one in less than a half hour. The lock turned out to be a slipped battery that the repairman fixed with equal quickness. Fast response is due to the fact that the owner uses the on-site management company. The unit is equipped with everything you might need to make your stay a pleasant one. Everything is there. A special treat was the nicely appointed veranda overlooking both the heated pool and scenic Lake Cay. Some of my family's favorite times were enjoyed on the veranda. At the end of our stay all my family regretted that we were leaving a place that was such a perfect fit for us. When you think of the cost for three bedrooms at Disney or any of the other hotels in the area, you should be able to see how value packed this rental can be for your family! By the way, Vista Cay is close to everything, and has a nice Publix grocery store, a Walgreens, and plenty of restaurants that deliver to the unit's door. Make your reservation, today. You won't be disappointed!

Responds fast! avg. 3 hours 46 minutes

Price per night from

$240

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. 2 hours 24 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

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

$343

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.

Price per night from

$209

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.

Price per night from

$172

Pleasant Point River Retreat

Geneva log cabin

1 bedroom / 2 bathrooms / sleeps 2

Responds fast! avg. 2 hours 1 minutes

Price per night from

$217

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 43 minutes

Price per night from

$252

Lovely 4BR 3bth Regal Palms Townhouse

Orlando townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 19 minutes

Price per night from

$141

Bargain Vacation Home near Disney

Kissimmee house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 58 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

Walk to Disney world! Full kitchen sleeps 6!

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$134

Condo less than a mile from Disney Orlando!!!

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 19 minutes

Price per night from

$131

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

$287

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$344

Bonnet Creek Resort

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 8

“A Piece of Paridise!” Owners were a pleasure to work with. Property was beautifully kept with lots of fun things to keep the kids busy. Great food & comfortable inviting atmosphere. Kids loved the gas fire pit near the pool and BBQ's by the pond. Condo was clean and well equipped. We definitely will be back!

Responds fast! avg. 28 minutes

Price per night from

$446

Wyndham Bonnet Creek Next Door to Disney

Orlando tower

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$229

Price per night from

$297

Viewing 38 of 1,340
rentals in Winter Park

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