Vacation Rentals & Villas in Winter Garden

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105 villas

Fantasy Pool Home

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 2 minutes

Match: Private pool

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Price per night from

$144

Modern 8 Guest End Town Home | Pool & Balcony 1507

Clermont house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Beautiful and Comfortable Vacation Home” We loved every minute of our stay at this house. It was very clean and comfortable with up to date, modern amenities, furniture and fixtures. It was perfect for our 10 day vacation to Disney and Universal and so much better than staying at a hotel as we were able to buy and cook our own food, swim in the private pool, and enjoy separate bedrooms and bathrooms for everyone in our party (4 people). It was heavenly to come home to this house after a long, hot, exhausting day at the parks. There are plenty stores and restaurants within 2 miles of the neighborhood. A word of caution: this house is actually in Clermont and it was a bit further from Orlando, and the Disney and Universal resorts than we thought (about 50 min. from the airport, 40 from Universal, 30 from Disney - mostly due to traffic and construction, actual mileage is not far) but still not a bad drive. Overall, we were very pleased with our choice. It was a great value and well worth every penny!

Match: Private pool

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Price per night from

$97

Rainbows End 3 bed & Bath - Florida Villa - Private Pool & Spa

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Better than a hotel” The villa is located in a nice,quite environment but close enough to Disney and to shopping opportunities. It is fully equipped with everything you would need, a lot of entertainment facilities are available. Too bad that the little children costumes in the closet wouldn't fit any of us. We very much enjoyed the calm environment after a long day spent in Disney World. Thanks for the pleasant experience hope we can return some times!

Responds fast! avg. 1 hour 1 minutes

Match: Private pool

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Price per night from

$161

3 Bed Home | Disney Area | Resort Facilities 17443

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Clean new home” This being my first time staying outside Disney I was nervous about renting a home. But this home was 5 stars in all aspects . The home is very well furnished and was clean . It was spacious for the whole family and travelling with young children cleanliness is most importnat for me. This home was spic and span including the kitchen ware . I would recommend this to any one . You just need a renatl car to get around

Match: Private pool

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Price per night from

$97

3 Bed Townhome | Disney Area | Pool & Balcony1507s

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$97

Modern 6 Guest End Townhome | Pool & Balcony 17401

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Relaxing and peacefull” Hi.. For sure recomended. Its cosy and relaxing and a neat neighboorhood. I had a few concerns but as soon as i reported anything, the attendance was fast. This made my stay feel safe. Wallmart , target and some restaurants were close by. For sure will visit it again. Thank you for everything !

Match: Private pool

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Price per night from

$97

Luxury villa next to Disney World

Clermont villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“A very different experience.” This was the first time that I ever rented a house versus a hotel and I would highly recommend renting a house. We were very pleased with the house, but extremely upset with the home owners that lived in the community. When inquiring about renting the home I asked if there was a place to park a motorcycle trailer and I was told I could park it at the club house. After arriving there I was told I couldn't park it there. They were very rude and uncooperative, and forceful about me moving the trailer.I also had a handicap lift on the back of my truck that was to long for the driveway. Another home owner complained and cussed me out because I was blocking the sidewalk. The driveway was very short with no room. The house was very clean and everything was as advertised. Very, very pleased with the house. Everything went very smoothly with payment & reservation. The home owner responded to e-mails very quickly until I tried to get him to reimburse me the $70.00 for having to store the trailer somewhere else.

Match: Private pool

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Price per night from

$185

3 bed villa private pool and spa close to Disney

Clermont villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Really clean and confortable house, with everything I need.” The house was really clean, it smell clean, and that is the most important thing to us. We found everything we need, enough towels for everyone. We enjoy the pool with my kids, during day and night. It is close to restaurants, markets, parks, etc.

Responds fast! avg. 1 hour 41 minutes

Match: Private pool

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Price per night from

$138

1523 Cozy & Astonishing w/Private Pool

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$114

3 Bed Townhome| Pool & Balcony| Disney Area 17313

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$97

Cozy/Family friendly 5BR/4B home with private pool, K&K Villa

Clermont villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

“What a great family vacation!” The house is everything we see in pictures and more! So cozy and spacious. It has everything you need. Its close to Disney parks and you need a car to get to most places, but that it`s not a problema in Orlando. There are restaurants and walmart and other stores nearby. It was definitely a good choice staying at the villa since we were a group of 14 with kids. It was nice to get home and make a meal and chill after a busy day hoping from park to park.

Match: Private pool

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Price per night from

$184

The Harmoni in Serenity - Orlando

Clermont house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$126

17419 Awesome & Modern w/ Private Pool

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$114

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

Match: Private pool

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Price per night from

$138

Luxury 3 beds/2 baths villa (sleeps 6)

Clermont villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$121

Welcome to Your Home From Home Villa 381

Four Corners house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$229

Stunning 4Br Villa, South Facing Pool, Lake View

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$178

1613 Cozy & Gorgeous w/ Private Pool

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$114

Pleasant house villa with private pool near Disney

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

Disney Sunshine Retreat

Kissimmee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Holiday Disney retreat” Perfect oasis. Clean, quiet and close to the parks. Perfect place to recharge and relax after long park days. Will definitely book again for park visits. Only suggestion is fix or replace couch in living room. It’s leather is peeling. But it’s very comfortable.

Responds fast! avg. 1 hour 38 minutes

Match: Private pool

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Price per night from

$148

Military owned and operated Free Heated pool and spa 8 miles to Disney

Clermont house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great House for the price.” This is a bargain house. Everything you need is already here. From strollers and bikes to all the pool toys. People have contributed along the way too which is nice to be able to leave things behind knowing they will be used. My only complaint would be that it takes about 30 minutes to get to the parks unless you know the alternative routes. Most people don't. Otherwise this place is fantastic.

Match: Private pool

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Price per night from

$166

Match: Private pool

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Price per night from

$155

New modern villa near Disney

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

1538TA

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$119

3 Bed 3 Bath Orlando Townhome with Splash Pool | Sleeps 9!

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 3 minutes

Match: Private pool

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Price per night from

$103

Luxury Villa with Private Pool 8 miles from Disney near Universal and golf

Clermont villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$171

Charming townhouse at Serenity Resort near Disney

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

Contact Free Check In, Relax by your Private Pool, Come Stay With Us!

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Responds fast! avg. 3 minutes

Match: Private pool

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Price per night from

$103

2BR/2BA DEAL 7mi to Disney-Legacy Dunes Resort (8923CL)

Four Corners condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Private pool

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Price per night from

$84

52 Large 5 bed villa with private pool overlooking water and conservation views

Four Corners house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$247

Sweet home with a nice private pool near Disney

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

17413SB - Serenity Resort

Four Corners house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$119

Modern house with private pool

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

Great Getaway Home 5 Miles From Disney Main Gate

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$171

Pleasant villa with private pool near Disney

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

Charming townhome with private pool near Disney

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$124

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

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$265

Sweet and pleasant villa with private pool

Four Corners townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 29 minutes

Match: Private pool

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Price per night from

$114

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rentals in Winter Garden

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