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Vacation Rentals & Villas in Winter Garden

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Price: high to low

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8,431 villas

' Special' 5 Star Vacation Home Near Attractions

Winter Garden house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$224

Only Minutes to Disney World - Fully Furnished

Winter Garden villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

Spacious Winter Garden Home w/ BBQ, Walk to Dwtn!

Winter Garden house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$124

Downtown Winter Garden Cottage w/ Yard!

Winter Garden cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$137

Modern Bungalow w/ Gas BBQ, Short Walk to Downtown

Winter Garden house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$98

Orlando holiday home, 10 minutes from Disney, gated community with pools

Winter Garden house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$96

Beautiful Vacation Home 4 Miles from Disney

Winter Garden house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$144

Great rentals within 20 miles that match your search

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$368

Excellent apartment in Orlando for up to 10 people

Four Corners apartment

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$349

Excellent spacious apartment in wonderful Resort

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$295

Contemporary Villa (Alarmed) with Private Pool

Clermont villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$158

Christmas get away in Orlando, FL

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$323

Premium Kissimmee Timeshare rental

Kissimmee villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$370

2 Bedroom Condo WestGate Palace

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$362

Beautiful 1 Bedroom Condo To Rent

Orlando condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$259

LUXURY Town Center Villa Disney Studio APT

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$224

A week of dream in a resort

Orlando house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$225

Marriott's Grande Vista # 1

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$361

Golf Resort and Magic of world Disney

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$128

Apartment close to Disney parks

Kissimmee apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$206

Wyndham Bonnet Creek 9560 Via Encinas, Lake Buena Vista, Orlando, FL

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$420

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$323

Luxurious 4 bedroom lakeside Villa near Disney

Four Corners villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$162

Beautiful Large Studio Condo on the Lake

Orlando apartment

/ 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 53 minutes

Price per night from

$258

The Ruby Retreat - Themed Lakefront Villa

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$259

1 bedroom, Mystic Dunes Resorts & Golf Club in Nov

Celebration villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$156

Lovely 4BR 3bth Regal Palms Townhouse

Orlando townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 30 minutes

Price per night from

$147

Christmas in Orlando, FL, 2- 8 people, 12/24-12/31

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$274

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

Orlando house

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$407

Vacation rentals

Kissimmee apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$186

Marriott's Cypress Harbor Resort

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$389

Westgate Lakes Resort and SPA

Orlando condo

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$556

Westgate Town Center

Kissimmee hotel apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$227

Spring Break at Silver Lake

Kissimmee condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$230

Orlando Timeshare For Rent

Orlando house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$167

Spend a week in Orlando in a 1 bedroom villa with kitchen at Harbour Lake!

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$518

Viewing 36 of 8,431
rentals in Winter Garden

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Top Destination reviews

Orlando holiday home, 10 minutes from Disney, gated community with pools
Vacation home in Winter Garden, FL

This was our first time booking through flipkey. Our transaction went very smoothly. We were very satisfied with our home and our visit to Florida. Thank you to our home owner for keeping in touch and answering all of our questions. … see more

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