Vacation Rentals & Villas in Winter Garden

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82 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!

Match: Shared outdoor pool (heated)

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Price per night from

$125

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

Match: Shared outdoor pool (heated)

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Price per night from

$114

Caitlins Disney Condo - Spacious and convenient

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Clean, quiet, comfortable, and roomy!” We have a large family, with 5 kids. We brought my mother with us on vacation, giving us a whopping 8 people to accommodate, for a week and this condo gave us plenty of space and beds for everyone to sleep comfortably! The gated community is great! Clean and quiet with plenty of parking.

Responds fast! avg. 3 hours 4 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$137

❤️ 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!!

Match: Shared outdoor pool (heated)

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Price per night from

$252

Deluxe Townhome, plus pool area TV!

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Deluxe townhouse” Had a great time, The condo was very nice pleasant surroundings, would book there again. Close to many restaurants, and places to visit. Main thing it was close to Disney.

Responds fast! avg. 1 hour 34 minutes

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Price per night from

$138

Legacy Dunes Condo, Kissimmee, Orlando

Kissimmee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$102

5 Miles from Disney, Amazing Rental Home in Kissimmee

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Disney vacation” The condo was great. Close to almost everything. Clean, fully stocked, Joanne was awesome.we can't wait to come back again next year.

Responds fast! avg. 2 hours 49 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$98

You Gotta See This

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$114

Stunning Condo Near All The Attractions In A Gated Community.

Kissimmee condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$103

Orange Lake Resort Kissimee FL

Kissimmee townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$377

Dream Vacation Home, Only 5 Miles from Disney & Close To Orlando Attractions!

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$205

Entire New Home! Gorgeous Decor, , Sleeps 10,TWO King Bedroom Suites, Pool!

Kissimmee condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 24 minutes

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Price per night from

$200

Like Staying In A Castle! Incredible Home, Sleeps 8, Pool, Nesr Dis

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Beautiful” Booked this place for Xmas!! Everything was perfect.. clean & spacious.. felt like home.. wld mos def book again..

Responds fast! avg. 1 hour 24 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$178

ENTIRE, NEW Home! Sleeps 6, Near Disney. Heated Pool & Spa - SPECTACULAR!

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 24 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$194

Great Getaway Home 5 Miles From Disney Main Gate

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated)

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Price per night from

$171

⭐ 6 Bedrooms 5 Bathrooms Villa - Great Deal! - Near Disney World ⭐

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Shared outdoor pool (heated)

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Price per night from

$265

Cozy 4 bedroom townhouse in a gated community 10 min from Disney

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Shared outdoor pool (heated)

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Price per night from

$160

NEW Home! Heated Pool At Your Staircase! Star Wars BR For The Kids!

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$178

Holiday Inn Club Vacations At Orange Lake Resort

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$214

Orlando condo at Legacy Dunes - resort amenities

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$108

Magic on Magnolia 4BR/3BA Villa /Gated Comm / Pool & S

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$194

Disney Vacation Condo - stay 6 days get 7th FREE

Four Corners condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Owner is awesome. Goes beyond to satisfy guest” This is a 3 bedroom 2 bath unit. Unit has everything you need. It was clean except for the carpets. I called the owner and she asked what did she need to do to make this better. I said clean carpets. She sent Stanley Steamer out to clean them! That was awesome! Loved that we had washer and dryer in the unit. The unit does need some TLC. Deck attached to the master is in need of repair and the bathroom could use and update for sure. We enjoyed our stay and it was very comfortable! Owner is fabulous to work with...best ever!

Match: Shared outdoor pool (heated)

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Price per night from

$100

Newly remodeled Condo at Legacy Dunes with easy access - resort amenities

Kissimmee condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$129

2-306 Legacy Dunes Resort in Kissimmee Florida

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$114

2-205 Legacy Dunes Resort in Kissimmee Florida

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$114

2-104 Legacy Dunes Resort in Kissimmee Florida

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$114

Villas at Summer Bay Resort 2br suite, Sunday check-in

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$91

Christmas Week Condo/ Next to Disney/ Dates Flexible/ River Island location

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$196

Lovely townhome near Disney Parks

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$166

Orlando vacation rental just minutes outside Unversal studios, Sea World, Disney

Celebration apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$136

West Village Condo, Family-Friendly Orange Lake Resort!

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$221

West Village Condo, Family-Friendly Orange Lake Resort!

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Shared outdoor pool (heated)

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Price per night from

$327

4-101 Legacy Dunes Resort in Kissimmee Florida

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$114

6-303 Legacy Dunes Resort in Kissimmee Florida

Kissimmee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$125

Liki Tiki Village 1br suite, Sunday check-in

Four Corners condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$75

1-101 Legacy Dunes Resort in Kissimmee Florida

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$102

Liki Tiki Village 1br suite, Saturday check-in

Four Corners condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$75

The Grove Resort Orlando

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$410

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rentals in Winter Garden

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