Vacation Rentals & Villas in Winter Garden

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2,653 villas

Beautiful one bedroom apartment seconds from Disney

Winter Garden villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$150

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

2br - 2200ft2 - Beautiful one story 2 bed/3bath

Orlando house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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$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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$194

Spacious villa near Disney

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 29 minutes

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$114

2br - 1000ft2 - Winter Park House

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$115

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$287

Weston Magic in Orlando

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$127

One of Disney's premier locations

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$563

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$322

LUXURY Lakes Villa Disney Studio APT

Orlando villa

  • 1 bathroom
  • sleeps 5

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$192

The Haven Emerald Island close to Disney Parks

Emerald Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 13 minutes

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$173

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$431

The Fabulous SKC Villa

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$173

Vista Cay Luxury Condo 3 bed/2 bath (#3030)

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect for large families” I have stayed in Vizta Cay many times before, but through a different leasing agency. I must say, this time I was highly impressed with the unit as well as all the items that were included and made our stay so nice and relaxing will be sure to book with you guys again.

Responds fast! avg. 53 minutes

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$598

Vista Cay Luxury 3 bedroom condo #3066

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Love Vista Cay” I have stayed at a Vusta Cay resort 3 times. I'm never disappointed in how the places are so clean nicely decorated. If available they will always be my 1st choice. The only thing I was disappointed in was the cable. It did not have a variety of channels and the signal did not work for every channel.

Responds fast! avg. 53 minutes

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$665

Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 15

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$207

Luxury 4 bd near Disney - pet friendly - free WIFI

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$246

LUXURY 3BR 3BA WINDSOR HILLS POOL TOWNHOME 2 mi to DISNEY - Sleeps 8

Kissimmee villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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$161

Luxury Villa in Hampton Lakes near Disney

Davenport villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 11

“Peacefull and relaxing” Great family condo, good pool, relaxed neighourhood. Plenty of space, offers privacy and yet a family and home feeling

Responds fast! avg. 3 hours 52 minutes

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$262

Fabulous Orlando/Disney Vacation. At Newly Refubished and Themed Long Leaf Villa

Four Corners villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

“Family vacation 2017” The house was beautiful and spacious. We enjoyed the pool and all of the major attractions were close. The house had all of the necessities we needed. The living room furniture and carpet was worn, but was fine. The owner was very easy to work with and was quick to respond. I would definately recommend this house and owner for your family vacation!

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$155

“Beautiful spacious home in a quiet Gated Community.” We were in Florida for the National Pop Warner Football finals. I was able to rent this home on short notice (one week) and was pleasantly surprised it was beautifully maintained and well stocked. Sri was very accommodating and easy to reach. We had several children with us of various ages and they were all kept occupied in the game room. Pool never really got warm but we did read the literature and wasn't expecting bath water but the pool and spa at the clubhouse was comfortable. Had a great time and would definitely rent again great value for your money. Also is very close to all the attractions just a short drive to any park you plan to visit.

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$431

TripAdvisor Award Winner 2011, 2012 & 2013.

Clermont house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

“Home away from Home” Traveled with my children and grandchildren for a Disney family vacation and this home was very warm and inviting for everyone. The pool was a huge plus for the grandchildren after a long day at the parks. Working with the owners for over a year prior to our arrival was a pleasure. They were so accommodating when an unexpected medical issue forced me to be hospitalized and Mike was able to let my son and grandson get in a day early to get ready for the rest of the family. I highly recommend this beautiful home to anyone who is travelling to the Clermont area.

Responds fast! avg. 2 hours 7 minutes

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$253

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

“Great place, good value!” This was our first time renting a house from an owner. We had a great experience. The owner Mary was very helpful and she even called us right after we checked-in to make sure that everything met our standards and we had what we needed. The unit is very clean, quiet and had everything we needed for our stay. The resort is in a great location and has easy access to expressway I-4 and 417. It takes less than 10 minutes to get to Disney and the Espn World Sport Center. We also enjoyed walking around Old Town in the evenings. We really enjoyed our stay in this unit. Thank you Mary for letting us stay there.

Responds fast! avg. 1 hour 49 minutes

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$109

“Location ideal” After a full day at the Disney Parks it is so enjoyable to walk into a spacious home away from home. Secure in the knowledge that everyone has room to spread out and relax from playing hard all day. A wonderful fully furnished townhouse with all the amenities of home in a gated community located just off of Fl 192 behind Kissemmee Old Town and only 3 miles from Walt Disney World s Animal Kingdom. Beautiful pool and play area are bonus over the top.

Responds fast! avg. 1 hour 49 minutes

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$109

Responds fast! avg. 1 hour 49 minutes

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$109

La Bella Vita Family Villa in Kissimmee by Disney

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

“Perfect” This house was perfect for our florida holiday. We were 2 families each with 2 children and we had all the space you could need to not feel on top of each other, the other double bedroom easily converted to an en suite for the other couple so we each had en suite and the kids had their own bathroom! House really well equipped and lovely decor, lovely and private on the back and on a spacious and quiet development, just a short drive to all the parks, shops, restaurant, excellent location! We were really busy with all the parks so it was so nice to come back to space and the pool and the hot tub were equally an essential and enjoyable part of our holiday along with all the parks! Wouldn't hesitate to recommend/book again.

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$195

“nice place well kept” This condo is in a good location. You can walk to Old Town to the car shows every friday and saturday nights. The wi-fi is excellent. There is plenty of room. We ride our bicycles up and down 192 on the very wide sidewalks. Many good restaurants within walking distance. The owner keeps you informed of the things you need to know in a timely fashion

Responds fast! avg. 1 hour 49 minutes

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$101

Stunning Lake View House 2mls to Disney,games room

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Superb orlando villa - fantastic family home away from home” This was our first ever booking with HomeAway/VRBO and we were immediately drawn by the description, photos and other reviews on the site for Lakeview House. We decided to go for it (a family of 3 adults, 2 children) and the booking process was seamless - Derek, the owner, was in constant touch and with very useful information ahead of arrival. Although our flight from the UK had a bit of a glitch (meaning we arrived in the dead of night) we found the place without issue. There is always a nagging doubt with 'owner direct' type sites that pictures can be taken to flatter, or camera angles used to conceal. However, this is completely without warrant in this case and I can categorically guarantee that what you see in the pictures is absolutely what you get in real life! Think that wonderful vista over the lake behind Mickey and Minnie framing the fountain is an illusion? Absolutely not, it's that fantastic. Think the pictures of the pool and spa look too good to be true? Well believe it, we enjoyed them to the full. Games room really that capable? Oh yes, my son and I enjoyed the pool table and the air hockey immensely. This villa was perfect, and as travellers a long way from home, it was a joy to stay in. Location was excellent - to the west end of the '192' so great for driving to the parks and in a quiet and tidy residential street. As there is no-one immediately to the right of this villa (there's a small 'inlet' from the lake) there is a 'semi-detached' feel to it which adds to the sense of open-ness and space when out the back. Facilities were superb, kitchen well appointed, TVs everywhere. Missing 'ice hockey' pucks were spotted before we arrived and dealt with proactively - this villa is clearly well managed and Derek gave us a ring mid-stay to check everything was ok. Beds were comfy and air con and fans meant the villa was always a welcome and refreshing haven at the end of tough day in the parks. It was an intense two weeks for us as a family, as we were doing the Disney and Universal 'thing' to the max but the villa was everything we hoped for and more. We whole-heartedly recommend this villa either as a base for doing the Orlando 'Madness' or simply as somewhere to stay 24/7 and soak up the sun quietly. We will certainly return, God-willing, and if you're reading this and tempted to book, go ahead and bon vacances! Thanks you Derek and Julie for sharing your home with us. Ali & Helen, South Wales, UK

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$206

Doc's Magical Escape, Sleeps 14, Wireless Internet

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Family Vacation” The house was nice. The grandkids loved the pool. The house was close to all the attractions. We enjoyed our vacation. We will book again

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$201

Lake View Dream Villa

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

“Very family friendly house...” This was a very family-friendly house .We had a great stay and the kids loved the pool. The house was very clean and well managed. If we had any question we were able to get them without the long wait .Would highly recommend this house for any family looking for a wonderful stay minutes for Disney.

Responds fast! avg. 23 minutes

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$146

Venetian Bay Village 3 Bedroom Townhouse

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“MAGICAL EXPERIENCE.” Our stay at the Venetian Bay Townhouse was a wonderful experience everyone should experience. It feels like Home away from home. It was secure the amenities were great. And the check-in process was seamless. Everything from the workout facility to the swimming pool was amazing. This should be apart of everyone's Florida experience.

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$92

Vacation Villa near Disney with Wireless Internet.

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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$115

Sunny Disney Pool Home in Gated Resort, Amenities for All

Orlando villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

“Decent place but lacking in some areas” For one week in July 2014, my family from Alabama to Alaska (with us from Canada) all stayed at 928 Solona Circle. Overall we were happy with the house rental but do not stay here if you need assistance with anything. It took my 4 phone calls over 3 days to just find out what the Wi-Fi password had been changed to (the one that we were emailed was incorrect). It may not be the safest neighbourhood as there were police men in the gated area twice during our stay. And the house was filled with broken outlet covers and had very dirty couches, which needed steam cleaning. It was a spacious home and we loved the walk-in closets as well as the ease in which to find it and the easy drive to Disneyworld. But if you want to stray there, you need to supply everything- even your own toilet paper and Kleenex. The jets ion eth hot tub did not work and the game room had a broken foosball table. Overall we were mainly happy with our stay but were disappointed with a few things.

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$190

The Enchanted Retreat - SPLASH PAD!!!!!

Kissimmee house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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$574

Royal Disney Villa Just 10 minutes from Disney

Davenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great” Comfortable, clean, spacious, very good Thank you

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$137

FLAGSTONE VILLA

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

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$362

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rentals in Winter Garden

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