Stay If You Dare - Vacation Rentals in Winter Park Village

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From US $360

         

9.8 (160 Reviews)

House

Casa Bella

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Maitland

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From US $201

         

|

10.0 (2 Reviews)

House

Modern DT Home-King size Bed-Patios-Long Stays-WiFi

• Air Conditioner
• Parking
• View

• Orlando
• College Park

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From US $160

         

|

9.4 (331 Reviews)

Cottage

Orlando Lakefront Tiny House Community

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Northwest Orlando

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From US $147

         

8.0 (2 Reviews)

House

Private Poolside Guest House In Winter Park/Orlando

• Air Conditioner
• Parking
• Pool

• Orlando
• Fairview Shores

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From US $117

         

|

9.9 (83 Reviews)

House

Roy's guest house

• Air Conditioner
• Parking
• View

• Orlando
• Orwin Manor

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From US $353

         

|

9.6 (1017 Reviews)

Hotel

The Alfond Inn

• Air Conditioner
• Parking
• Pool

• Orlando
• Winter Park

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From US $190

         

New

Apartment

Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Winter Park

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From US $93

         

|

9.9 (40 Reviews)

House

College Park-Orlando 5Star Villa Oasis - Home Away From Home - QUIET Neighborhood-PRIVATE Botanical Courtyard - mins from EOLA,DT, Winter Park - Free Parking & EV Plug In

• Air Conditioner
• Parking
• View

• Orlando
• College Park

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From US $237

         

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9.2 (625 Reviews)

Hotel

Hilton Garden Inn Winter Park

• Air Conditioner
• Parking
• TV

• Orlando
• Winter Park

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From US $244

         

9.6 (10 Reviews)

House

Cute bungalow minutes walk from Park Avenue.

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Winter Park

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From US $221

         

10.0 (148 Reviews)

House

Temporary living that feels like home where you can relax and be yourself.

• Air Conditioner
• Parking
• TV

• Orlando
• Maitland

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From US $197

         

10.0 (95 Reviews)

Apartment

Stylish Boutique Guest house in Winter Park

• Air Conditioner
• Parking
• TV

• Florida
• Fairvilla

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From US $146

         

10.0 (37 Reviews)

Cottage

A curated stay in the Historic College Quarter

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Winter Park

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From US $191

         

10.0 (33 Reviews)

House

Charming Clean Home near East End Market Large fenced yard

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Audubon Park

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From US $513

         

10.0 (16 Reviews)

House

King bd/Charming 2 story cottage w/Private Yard

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Colonialtown North

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From US $742

         

10.0 (11 Reviews)

House

Luxury Ranch 2 Master Kg Bed w/heated Salted Pool

• Parking
• Pet Friendly
• Pool

• Orlando
• College Park

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From US $1,011

         

10.0 (6 Reviews)

Villa

Stunning Luxury Home in Artsy Winter Park featuring Nintendo-Themed Game Room!

• Air Conditioner
• Parking
• Pool

• Orlando
• Baldwin Park

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From US $536

         

10.0 (6 Reviews)

House

Lakefront Paradise Near Attractions

• Air Conditioner
• Parking
• TV

• Orlando
• Fairview Shores

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From US $267

         

10.0 (4 Reviews)

Apartment

Just 3 Blocks to Park Ave Shops/Restaurants, 2 From The Winter Park Village!

• Air Conditioner
• Parking
• Pool

• Orlando
• Winter Park

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From US $197

         

10.0 (4 Reviews)

House

Charming bungalow with plunge pool located steps away from trendy Mills 50 area.

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Colonialtown North

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From US $162

         

10.0 (4 Reviews)

House

Home away from home in the heart of charming Winter Park!

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Winter Park

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From US $145

         

10.0 (4 Reviews)

House

Cozy Comfort Just 2 Blocks From Park Ave!

• Pet Friendly
• Pool
• TV

• Orlando
• Winter Park

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From US $427

         

10.0 (3 Reviews)

House

URBAN OASIS: Dog Friendly - Bungalow Retreat - Downtown Orlando

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• College Park

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From US $284

         

10.0 (3 Reviews)

House

3Bdrm Home Near Downtown Orlando and Winter park

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Eatonville

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