Winter Park, FL, USA Vacation Rentals

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United States Florida Orlando vacation rental compare prices direct by owner 29205091

GardenHouse @AudubonPark Sleeps 8

4.9 (179)

3 Bedrooms • 8 Guests

$239 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40213260

CasaDelaney DT Sodo district. Renovated Sleeps 16

4.8 (282)

4 Bedrooms • 16 Guests

$280 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40784226

La Maison de Lorbu - Private apartment/Breakfast

5.0 (89)

1 Bedroom • 2 Guests

$134 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860509

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

4.9 (51)

5 Bedrooms • 16 Guests

Available on

United States Florida Orlando vacation rental compare prices direct by owner 40860477

Foodie Lovers Walkable Mills50 - Sleeps 10

4.9 (166)

2 Bedrooms • 10 Guests

$191 avg/night

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United States Florida Orlando vacation rental compare prices direct by owner 40860499

The Villa Orlando@College Park. Sleeps16.

4.9 (192)

4 Bedrooms • 15 Guests

$396 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40740132

Tiny home near downtown w/ outdoor patio

4.8 (171)

1 Bedroom • 3 Guests

$140 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860484

Funky Remodeled Otown Bungalow Sleeps 8

4.8 (167)

2 Bedrooms • 8 Guests

$188 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860488

Orlando CP Duplex. Pet Friendly. Near DT & WP ‼️

4.8 (78)

2 Bedrooms • 7 Guests

$136 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860492

Cozy home 5min to Park Ave and Downtown Orlando

4.8 (92)

2 Bedrooms • 6 Guests

$176 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860497

Spacious Patio and Modern Amenities - Stylish Orlando Retreat

4.8 (104)

3 Bedrooms • 15 Guests

$145 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860470

Charming home @wp. Patio +Gazebo. close to highwys

4.8 (142)

2 Bedrooms • 7 Guests

$170 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860486

Spacious 1BD-3min to Winter Park 15.min to Springs

5.0 (18)

1 Bedroom • 6 Guests

Available on

United States Florida Winter Park vacation rental compare prices direct by owner 40860507

Private Urban ComplexSleeps27. Close to WP, CP, DT

5.0 (1)

8 Bedrooms • 16 Guests

$1,460 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860473

Comfy Remodeled 2bd near DT.WP & Mills50 District

4.9 (8)

2 Bedrooms • 6 Guests

$252 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860480

Cozy Retreat in the Heart of Orlando near Hwy's

4.8 (12)

4 Bedrooms • 13 Guests

Available on

United States Florida Winter Park vacation rental compare prices direct by owner 40860498

Comfy Tiny Home @WP. Large Private Deck+Queen bed

4.8 (145)

1 Bedroom • 3 Guests

$116 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860481

College Park Bungalow Sleeps 20+ 2 Kitchens-Fenced

4.8 (54)

5 Bedrooms • 19 Guests

$475 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40872253

Orlando Downtown 3Bbd Near Arts Center | Sleeps 13

4.8 (79)

3 Bedrooms • 12 Guests

$264 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860479

Orlando Tiny Home near KIA center w Free Parking

4.8 (207)

1 Bedroom • 2 Guests

$111 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860483

Stylish Duplex walkTO Lake Eola Orlando. Sleeps 8

4.8 (204)

2 Bedrooms • 8 Guests

$222 avg/night

United States Florida Winter Park vacation rental compare prices direct by owner 40860472

Mills House @WP. Sleeps 10 Renovated. Queen beds

4.7 (241)

3 Bedrooms • 11 Guests

$241 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860469

Charming College pk Duplex @Lake Fairview Sleeps 8

4.7 (128)

2 Bedrooms • 8 Guests

$134 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860505

Cozy Pet Friendly home near CP WP and Downtown

4.7 (22)

5 Bedrooms • 15 Guests

$403 avg/night

United States Florida Orlando vacation rental compare prices direct by owner 40860457

Downtown Studio Walk to Lake Eola & KIA center

4.7 (144)

1 Bedroom • 2 Guests

$104 avg/night

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