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Holiday Houses in Winter Park

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2,723 Holiday homes

Winter Park-College Park-Orlando-1

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

2

Responds fast! avg. 2 hours 58 minutes

from £73 / night

£464 / week

The Cottage on Lake Fairview, Orlando.

Winter Park house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 minutes

from £424 / night

£2,306 / week

Mid-Century Modern Gem

Winter Park townhouse

2 bedrooms / 1 bathroom / sleeps 6

from £132 / night

£923 / week

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

2

from £123 / night

£857 / week

Winter Park-College Park-Orlando -2

Winter Park house

1 bedroom / 1 bathroom / sleeps 2

2

Responds fast! avg. 2 hours 58 minutes

from £73 / night

£464 / week

$ Picasso Villa $ Ultra Luxurious Abstract Villa

Winter Park villa

4 bedrooms / 3 bathrooms / sleeps 10

from £518 / night

£3,624 / week

"Lakeside" in old Winter Park (exclusive 32789zip)

Winter Park villa

4 bedrooms / 4 bathrooms / sleeps 8

from £559 / night

£3,754 / week

Championsgate 58 - villa with pool, game room and theater room near Disney

Winter Park house

8 bedrooms / 5 bathrooms / sleeps 20

from £212 / night

£1,480 / week

Great rentals within 20 miles that match your search

VISTA CAY. New!POOLSIDE ESCAPE NEAR ALL PARKS, ATTRACTIONS & INTERNATIONAL DRIVE

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 31 minutes

from £231 / night

£1,614 / week

Luxurious

Orlando apartment

3 bedrooms / 4 bathrooms / sleeps 8

58

from £130 / night

£889 / week

Brand New 5BD/4BA & private pool home next to Disney & Universal

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 41 minutes

from £149 / night

£1,053 / week

The WHITE HOUSE 25 min from Disney

Zellwood house

3 bedrooms / 3 bathrooms / sleeps 6

from £183 / night

£1,278 / week

139 - Luxury 2 Masterbed/bath Unit with Garden View - International Drive

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 43 minutes

from £177 / night

£1,238 / week

Sheraton Vistana Fountains II - Timeshare

Kissimmee hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

1

from £127 / night

£885 / week

Marriott Cypress Harbor 2 bedroom sleeps 6

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

from £267 / night

£1,870 / week

Pat and Ron's Holiday Home, Relaxing Retreat

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

40

from £92 / night

£642 / week

Luxury 3 Bedroom in Orlando

Orlando townhouse

3 bedrooms / 4 bathrooms / sleeps 8

from £127 / night

£884 / week

Vista Cay Standard 2 bedroom condo (#3102)

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 50 minutes

from £87 / night

£609 / week

Your Beautiful 5 Star Villa Minutes from Disney on the Prestigious Sonoma

Kissimmee villa

15 bedrooms / 13 bathrooms / sleeps 30

from £604 / night

£4,225 / week

Wyndham Bonnet Creek Resort

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 8

3

Responds fast! avg. 2 hours 58 minutes

from £201 / night

£1,406 / week

VACATION RIGHT OUTSIDE OF DISNEY

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

2

from £188 / night

£1,312 / week

VISTA CAY ORLANDO LUXURY TOWNHOME NEAR UNIVERSAL, DISNEY, CONVENTION CENTER

Orlando apartment

3 bedrooms / 4 bathrooms / sleeps 8

5

from £206 / night

£1,311 / week

The Coastal Cottage

Sanford apartment

2 bedrooms / 1 bathroom / sleeps 4

1

from £94 / night

£656 / week

Westgate Lakes Resort & Spa Near Universal Studios Area

Orlando studio

Studio / 1 bathroom / sleeps 4

from £140 / night

£978 / week

Peaceful Cozy East Orlando Home (Bedroom 1)

Orlando guest house

1 bedroom / 1 bathroom / sleeps 2

from £43 / night

£296 / week

Perfect Home Away-Orlando King size Bed

Orlando house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 53 minutes

from £169 / night

£553 - £816 / week

Enjoy July Fourth Week in the heart of Disney Country

Orlando villa

3 bedrooms / 2 bathrooms / sleeps 8

from £258 / night

£1,804 / week

Great Home 12min from Disney w/POOL

Orlando house

3 bedrooms / 3 bathrooms / sleeps 8

1

from £141 / night

£836 / week

Spacious home with pool, near Disney, Lake, Malls

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

from £169 / night

£984 / week

Casita del Sol - 2 bedroom - KING in Master Suite PRIVATE Apt. in Home

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 4

4

from £84 / night

£584 / week

A spacious 3 Bedroom gated resort Close to Disney

Kissimmee apartment

3 bedrooms / 2 bathrooms / sleeps 8

2

from £87 / night

£605 / week

BEAUTIFUL 2BR/2BA CONDO AT VISTA CAY RESORT

Orlando house

2 bedrooms / 2 bathrooms / sleeps 6

from £122 / night

£797 / week

Laguna Reef

Celebration house

8 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 36 minutes

from £104 / night

£724 / week

Christmas get away in Orlando, FL

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

from £235 / night

£1,645 / week

2 Bedroom Condo WestGate Palace

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

from £263 / night

£1,842 / week

NEW HOME ORLANDO - Disney STOREY LAKE

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 12

from £159 / night

£1,112 / week

Large Room Central to Everything in Orlando

Orlando private room

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 21 minutes

from £38 / night

£216 / week

Beautiful 1 Bedroom Condo To Rent

Orlando condo

1 bedroom / 1 bathroom / sleeps 4

from £188 / night

£1,316 / week

Westgate Blue Tree: 2-BR, Sleeps 6, Full Kitchen

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 33 minutes

from £104 / night

£729 - £1,480 / week

NEW HOME ORLANDO

Kissimmee villa

5 bedrooms / 4 bathrooms / sleeps 12

from £206 / night

£1,441 / week

Viewing 40 of 2,723
rentals in Winter Park