Vacation Rentals & Villas in Winter Park

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217 villas

Gorgeous apartment just minutes to Disney parks, Orlando Florida.

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful Place to stay” I stayed at the Island Club for a period of 3 months and was very happy with my stay. It was quiet, and comfortable. I liked the layout of my condo which was on one floor. My family of 5 had plenty of room to enjoy. I also liked how there was a patio in back. It made it feel more like a home. We stayed on the top floor where there was vaulted ceilings and lots of windows in the front room. This made it feel more spacious and rich. The amenities were additionally nice as well. There were 2 different pools and jacuzzis, tennis court, clubhouse and work out room to enjoy. I also liked how you could park right up against your condo building. The location was very convieinent as well. It is close to all major attractions. 15 minutes from Disney - 25 from Universal and close to shopping, and restaurants. I would stay here again in a heart beat!

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$125

Luxurious 3 Bedroom Townhome-1.5 miles from Disney

Kissimmee villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Great Experience” The villa did not disappoint and was a great place for my family and I to stay during our world wind visit to Disney. I would recommend this place to anyone who is going to Orlando with a large group :-)

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$121

Marriott's Royal Palms Resort Orlando Near Disney

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$171

The Ultimate Florida Vacation

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” Very cozy, out in suburbs. Neighborhood clean and friendly. Pools and outdoor basketball courts and activities for the kids.

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$110

Your home for Disney/Universal/Golfing:) with pool, spa Sleeps 8+

Clermont villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 8 minutes

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$126

⭐Comfy Villa w/ Golf Clubhouse - Adventure & Thrills For Everyone⭐

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

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$336

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$171

Disney themed villa/private pool/tub.

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

“Amazing vacation” The house was perfect. Everything was great. House looks just like the pictures. George was a great host. Very nice and made it feel like a second home. Cant wait to go back.

Responds fast! avg. 3 hours 15 minutes

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$193

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$228

Disney Vacation Rental, Private Townhouse in gated community

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$163

Disney-Dream-Come-True-Villa

Davenport house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 14

“Great place to make memories!” Loved having the children and grandchildren all together for a school vacation. We were so close to many venues and didn't need anything but the pool to entertain us once we returned home every day! Spacious house, that was well stocked with linens and cookware. Nice neighborhood. We would come back again. :)

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$172

“Paradise” My husband and I plus 3 children recently returned from our first trip to Orlando, Florida. We stayed in the Villa Esquire. I can't say enough good things about this place! The neighbourhood is beautiful. I spent many hours walking the streets with my 3 children and always felt completely safe. David and Nikki did everything within their power to make our stay comfortable and fun! They called several times just to see if there was anything that they could assist us with. They keep this home in immaculate shape. Everything from the paint to the appliances, bedding, dishes, and electronics are brand new. This home is also spotless and tastefully decorated with tons of personal touches to make you feel right at home. It had everything I could possibly need for my infant including; a brand new stroller, a play pen and high chair to even baby spoons and baby linens. The kitchen is fully equipped to help with all of your cooking needs big or small. I even found a sewing kit when I ripped the hem on my dress! The layout of this home is perfect for several families. There is two master suites; one upstairs and one down. So even though we had 3 different groups in the home their was still tons of privacy. The game room was awesome! My kids and husband spent many evenings enjoying the x box, pool table etc. We also spent hours on end enjoying the heated pool! The kids loved it so much we had a hard time convincing them to leave the house to hit the parks! Disney is a close 15 minutes, Sea World 25, Busch Gardens 1 hour, and Cape Canaveral Beach a hair over an hour. There are also loads of restaurants nearby such as Olive Garden, Long Horn, Chilies, and applebee's. Plus a choice choice of shopping centres and outlets. the grocery, post office and Walmart were literally a five minute drive down the street. We absolutely loved Florida and this beautiful home and hope to return soon. Thank you David and Nikki for making our stay perfect and our trip one we will never forget!

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$342

⭐Great Value Villa w/ Private Pool - Nearby Disney Resort⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

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$265

Upscale 2BR Condo at Terrace Ridge near Disney FL

Davenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Very Nice Location, Property, and Experience” The booking process was very easy and straightforward. It was much easier than bookings I have done on other sites. I felt my payment and information was secure. The process of checking in and getting access to the condo was very efficient as well. There was a minor hiccup with the entry code, but the customer service line was able to correct it right away. The house was nice and spacious. It had everything we needed to ensure we had a proper vacation. While there were some initial headaches, the owner and customer support line were always there to ensure we were satisfied. The location was great. it seems that there is a lot of development going on in this location. There were multiple places to eat, and shop. It was not far from all of the main attractions. Because of its proximity to I-4, there was minimal traffic. The pool and facilities were clean and comfortable. I met a lot of nice people there. I would recommend this condo to anyone looking for a peaceful vacation that is close to all the great things in Orlando.

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$109

Tupelo Magic - Disney Orlando

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Awesome Home” This home was beautiful! It was all the was described and more! My family and I had an amazing time! Our only regret was that we were so busy and did not get much time at the home relaxing.

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$189

Grand Palms Resort - Vacation Rental - 3BR, 2BA

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great place” Have a great experience there. Very clean very well furnished.quiet place. Have a great time there,s a great pool . thanks

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$114

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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$87

“Beautiful home!” Beautiful home, spacious. There were a few small hiccups, but the homeowner was so attentative! She quickly resolved any issues. The home is close to the parks, not too much time in the car, that was nice. Overall, my family truly enjoyed the stay and we would definitely rent this home again!

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$218

Sleeps 8-12 HOUSE PRIVATE YARD/ POOL/SPA

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

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$203

Beautiful and Spacious Orlando Pool Home

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

“Awesome Place to Stay!” Stayed there for a week and had an absolute ball. Villa is extremely clean and exactly as pictured on the website. We had so much fun in the pool we forgot the Villa had a pool table! Definitely booking this one again next vacation!

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$138

5* Windsor Palms, Conservation View, South Facing!

Orlando house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$212

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$336

Executive 7BR/4.5Bath home near DisneyWorld with Pool/SPA/Game Room

Davenport house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

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$315

Westside | South Facing Pool | Disney Area | 9110

Kissimmee villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“Disneyland Holiday” The villa was lovely and clean. It had everything that we needed and was a pleasure to stay there. Thank you for letting us share your lovely home

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$114

Camper Standing 30 Ft Travel Trailer

Clermont caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$81

LUXURY Town Center Villa Disney Studio APT

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$198

The Harmoni in Serenity - Orlando

Clermont house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$126

Upgraded 5-star Penthouse, Bahama Bay near Disney

Davenport apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Very comfortable stay - enjoyed every moment of it!” Very spacious accommodations. We stayed 2 families with little girls who were very anxious to see Disney World parks. The condo was perfect for our stay, we were just about 20 minutes from Magic Kingdom so we were there in a snap. The resort is beautiful and we can't wait to come back again. There are multiple swimming pools, one close to condo's building, another one - bigger and open until 10 pm - near the club house / reception. Another similar size pool at the restaurant area with little white sand beach, volleyball net and table tennis. Also we enjoyed playing tennis on the real hard court surface near reception, very good quality and with lighting. When you need a day off from visiting parks and all these crowds staying on the resort is the great option. Shopping is very close to the resort - 7 minutes drive to Walmart, so you could get anything you need, open 24 hours. We also recommend buying tickets to all attractions at the Walmart since there is a small discount vs buying at the gates. Overall - great experience, highly recommend to anyone. Will definitely come back again!

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$227

Luxurious 3 Bedroom with Pool and Jacuzzi, near Disney

Kissimmee hotel apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Clean and secure.” Close to everything that we had planned. Loved the security. Nice pool and grounds. Quiet area ,well maintained.

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$98

“Excellent accommodations.” Excellent accommodations and location. House was very clean and pool was perfect facing the south sun.

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$401

Wyndham's Bonnet Creek 2 BD/2BA Deluxe Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Bonnet Creek is our favorite resort in the entire area” Awesome stay as usual! The little extras are above and beyond any other place in the area. The live music, fun bartenders, games for the kids and outstanding accommodations, along with several pools, game rooms, grills etc. You couldn't ask for more in a resort

Responds fast! avg. 1 hour 31 minutes

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$163

❤️ Super Cozy Home Minutes to Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Birthday Trip!” I do believe this might have been the funnest trip I've ever taken in my life. Having every single thing just minutes away from you was such a delight and such a pleasure to not have to drive around constantly in the car. This community is gated and seems like a really fun place to actually buy a vacation home. Actually, while we were there we looked into it and might be doing the same thing that this particular person is offering on TripAdvisor as well! First of all, the house was just absolutely amazing... Bigger than my own home even. It was just me, my son and my husband and our house was absolutely humongous. We actually had thought we would have another family with us but it fell through. Everything was clean and perfect. There were many things like dishwasher, laptop, printer, hair dryer, straightener, toiletries, food! When we arrived, we already had some basic needs that were furnished To Us by the owners. It was such a treat to see that they really cared about us to furnish those things! There was a perfect screened in porch out the back over looking a little bit of a water marsh where we got to watch the birds everyday. The wildlife in our particular yard was extremely delightful. From frogs to lizards two birds two cranes we had an amazing time when we were relaxing at home. To my delight, there were also three swimming pools in the complex. One of the pools were in the middle of the community which was right down the street from our home, then there were two others inside the clubhouse which were also fantastic. We really enjoyed the hot tub and sitting underneath the shelter when it started to rain. Since I knew it would be very hot and we would be extremely exhausted, I asked for a maid service halfway through our vacation and I'm so happy I did. It was nice to come home after dinner to a 100% clean house with clean towels and everything perfect. I recommend that you get the service as the cleaning lady does an excellent job! The next time we booked our Walt Disney World vacation I will be using this home again without a doubt. Even though we stayed 7 days, we still did not get to see everything that we wanted to. Next time we come down we are doing 10 to 12 days for sure and cannot wait to come back to Vista Del Lago. I was really surprised on how many friends we made while we were there!! If you are looking for a family home that could easily sleep 7 people, please do yourself a favor and book this, you will be so glad that you did!!

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$252

4BR/3BA 1650 sqft Condo from $100/nt, 2 Miles to Disney

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent Location” THis place was great for our family we stayed for 12 days and have no complaints. We will try to stay next year as well. Thank you

Responds fast! avg. 1 hour 27 minutes

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$115

FloridaNearDisney from $89 per night

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Florida Vacation” Absolutely loved the villa and location. Villa was very nice and located perfectly in a gated community that had an awesome pool with tiki bar, splash pad for kids, playground for kids and all the other normal amenities. Would recommend to anyone looking for a Florida or theme park vacation. Only 5 min from Disney and 15 from Universal with several restaurants and shopping rite within a mile. Highly recommend. Thanks to the owners for making everything so easy, checking in and fast responses.

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$137

2 miles to Disney,1650 sqft 4BR/3BA big Condo from $80/nt

Kissimmee apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent location and all the comforts of home.” Condo was within walking distance of a Winn Dixie grocery store, Fridays, Cracker Barrel, and Outback. The community pool and hot tub were excellent. The condo was equipped with everything we needed. The only negatives were the fact that we were a little disappointed that the ice maker didn't work and definitely dismayed by the fact that the smoke alarms were disconnected. We also had some periodic problems with the cable TV and wi-fi. Those are the things that caused a very good rating instead of an excellent rating. But other than those we would highly recommend the place and definitely stay again, especially if the smoke alarms are fixed.

Responds fast! avg. 1 hour 27 minutes

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$126

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$117

Unique 5 Star Home - Private Pool, Free SOLAR Pool heat, WIFI, BBQ, Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Violet lane” Home was clean and charming.We enjoyed the pool and privacy greatly. Owner thought of most anything we may need, except one; toilet paper. This was our first time staying in a private home rather than a hotel so perhaps it isn’t a given but if we had known, it would have saved us an immediate trip to store. I cannot speak for other guests but felt that not starting laundry, despite stating was not mandatory, not doing so may affect my deposit. A few other minor issues: missing ping pong table, “key?” to working slot machines, how, or if, the ice maker worked and where the garage door opener was located(we did find on the furnace in the garage the day before we left), and whether the swinging chair was safe to use, despite the crack, may have been problems easily remedied with a phone call but ultimately not important enough to bother owner and take time away from us. Not meant to be a negative review, it is not. Overall, we had a lovely time and would stay again. However, it seemed important to be honest in regard to our experience.

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$149

Florida Jewels

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$185

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