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Holiday Houses in Winter Park

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1,288 Holiday homes

2br - 1000ft2 - Winter Park House

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 5

2

Responds fast! avg. 1 hour 37 minutes

from £93 / night

£645 / week

The Mid-Century Modern Gem

Winter Park townhouse

2 bedrooms / 1 bathroom / sleeps 5

from £148 / night

£1,032 / week

HOME AWAY FROM HOME in beautiful Winter Park

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 7

1

Responds fast! avg. 16 minutes

from £139 / night

£968 / week

Relaxing, lake-view home near Park Avenue

Winter Park house

2 bedrooms / 2 bathrooms / sleeps 6

from £267 / night

£1,864 / week

Great rentals within 20 miles that match your search

Disney location vila with 4 poster bed, pool, wifi

Kissimmee villa

4 bedrooms / 2 bathrooms / sleeps 8

9

from £126 / night

£802 / week

Villa Linton - Beautiful Florida Home with Themed Bedrooms

Kissimmee villa

5 bedrooms / 3 bathrooms / sleeps 10

33

Responds fast! avg. 2 hours 32 minutes

from £115 / night

£802 - £916 / week

LUXURY Lakes Villa Disney Studio APT

Orlando villa

/ 1 bathroom / sleeps 5

from £154 / night

£921 - £1,482 / week

2 Bedroom Deluxe Suite @ Blue Tree Resort

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 6

2

from £145 / night

£1,014 - £1,198 / week

Warm and Inviting. Ideally located, 3BR/2BA Home

Maitland house

3 bedrooms / 2 bathrooms / sleeps 8

from £185 / night

£1,198 / week

Westgate Lakes, Orlando Florida - 4 Bedroom Villa - Huge Resort with everything

Orlando hotel apartment

4 bedrooms / 4 bathrooms / sleeps 16

4

from £329 / night

£2,299 / week

Awesome 4 Bedroom Gated Condo with only minutes to the Disney area

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

16

from £92 / night

£639 / week

Lakefront Townhouse 5 Star LOCATION

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

6

Responds fast! avg. 2 hours 8 minutes

from £97 / night

£645 / week

Villa Bella Vista Cay Penthouse/Lakefront Condo Overlooking the Pool & Lake Cay

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

48

Responds fast! avg. 3 hours 46 minutes

from £193 / night

£1,348 / week

Luxurious

Orlando apartment

3 bedrooms / 4 bathrooms / sleeps 8

58

Responds fast! avg. 3 hours 46 minutes

from £184 / night

£1,284 / week

Elegant Modern Condo/Apt. in Sunny Orlando !

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 6

27

from £70 / night

£488 / week

Beautiful Large Studio Condo on the Lake

Orlando apartment

/ 1 bathroom / sleeps 4

from £184 / night

£1,290 / week

Wonderfull Villa in a luxury Resort

Orlando villa

3 bedrooms / 3 bathrooms / sleeps 12

1

from £277 / night

£1,861 / week

Studio with a kitchen in Enclave Suites Orlando

Orlando hotel apartment

1 bedroom / 1 bathroom / sleeps 2

1

Responds fast! avg. 1 hour 2 minutes

from £73 / night

£544 / week

Orlando / Gated Golf Community / Ventura / 3 Bed/

Orlando townhouse

3 bedrooms / 2 bathrooms / sleeps 6

1

from £83 / night

£581 / week

Beautiful 2 Bedroom Condo on the Lake

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

from £276 / night

£1,926 / week

LUXURY Town Center Villa Disney Studio APT

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

from £160 / night

£921 - £1,295 / week

Disney for the Holidays! 1-Bedroom Villa Orlando

Orlando apartment

1 bedroom / 1 bathroom / sleeps 4

from £157 / night

£1,014 / week

from £270 / night

£1,890 / week

ENHANCED CLEANING HERE! Great AMENITIES and SO MUCH MORE! 2BDRM Condo!!

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 8

11

from £168 / night

£1,174 / week

Luxury Condo at Hotel prices - Isles of Cay Commons

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

13

from £139 / night

£968 / week

Pleasant Point River Retreat

Geneva log cabin

1 bedroom / 2 bathrooms / sleeps 2

8

Responds fast! avg. 2 hours 1 minutes

from £175 / night

£1,013 / week

Nice Furnished Vista Cay 3BD/3.5BA TownHome

Orlando hotel apartment

3 bedrooms / 4 bathrooms / sleeps 8

7

Responds fast! avg. 1 hour 43 minutes

from £203 / night

£1,419 / week

Great Resort Villa next to SeaWorld and near Disney & Universal Studios

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £175 / night

£1,219 / week

Walk to Disney world! Full kitchen sleeps 6!

Orlando villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

from £108 / night

£756 / week

Condo less than a mile from Disney Orlando!!!

Orlando villa

1 bedroom / 1 bathroom / sleeps 4

2

Responds fast! avg. 2 hours 19 minutes

from £106 / night

£736 / week

Disney for the Holidays! 3 Bedroom in Orlando

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

from £254 / night

£1,474 / week

2-Bedroom Villa - Orlando

Orlando apartment

2 bedrooms / 1 bathroom / sleeps 6

from £208 / night

£1,290 / week

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

from £231 / night

£1,474 / week

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 8

from £277 / night

£1,659 / week

Bonnet Creek Resort

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 8

3

Responds fast! avg. 28 minutes

from £359 / night

£2,509 / week

Wyndham Bonnet Creek Next Door to Disney

Orlando tower

2 bedrooms / 2 bathrooms / sleeps 8

from £185 / night

£535 / week

from £239 / night

£1,588 / week

★ Simple and Cozy Town Home - 4 Miles to Walt Disney World & Many Theme Parks ★

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 8

from £75 / night

£523 / week

Holiday Villa Orlando Florida

Orlando villa

4 bedrooms / 3 bathrooms / sleeps 9

34

Responds fast! avg. 1 hour 53 minutes

from £92 / night

£642 / week

1 week Westgate Resort Studio in Orlando_Sleeps 4

Orlando condo

1 bedroom / 1 bathroom / sleeps 4

from £86 / night

£599 - £829 / week

Viewing 40 of 1,288
rentals in Winter Park