Floridarentalvacations - Vacation Rentals in Winter Park Village

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From $161

         

10.0 (22 Reviews)

Apartment

Mid Century Luxury, 1 block from Park Ave (#2)

• Air Conditioner
• Parking
• TV

• Orlando
• Winter Park

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From $117

         

|

9.9 (83 Reviews)

House

Roy's guest house

• Air Conditioner
• Parking
• View

• Orlando
• Orwin Manor

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From $96

         

10.0 (13 Reviews)

Cottage

77 m² Cabin ∙ 2 bedrooms ∙ 4 guests

• 828 ft² Cottage
• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• College Park

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From $92

         

New

Cottage

Cozy Cottage in Orlando's Garden District

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Florida
• Orlando

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From $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 $93

         

|

9.9 (33 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 $97

         

10.0 (2 Reviews)

House

82 m² House ∙ 2 bedrooms ∙ 4 guests

• 882 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Winter Park

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From $331

         

|

9.4 (1007 Reviews)

Hotel

The Alfond Inn

• Air Conditioner
• Parking
• Pool

• Orlando
• Winter Park

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From $181

         

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 $167

         

|

9.8 (10 Reviews)

House

Beautiful Bungalow

• Air Conditioner
• Parking
• Balcony/Terrace

• Orlando
• College Park

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From $137

         

|

9.0 (9 Reviews)

House

House ∙ 1 bedroom ∙ 3 guests

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Northwest Orlando

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From $183

         

|

9.2 (551 Reviews)

Hotel

Hilton Garden Inn Winter Park

• Air Conditioner
• Parking
• TV

• Orlando
• Winter Park

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From $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 $244

         

|

9.8 (5 Reviews)

House

The Winter Park Experience

• Air Conditioner
• Parking
• View

• Orlando
• Winter Park

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From $198

         

10.0 (146 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 $68

         

|

9.7 (3 Reviews)

House

Lovely Spacious Guesthouse in Mills 50 District

• Air Conditioner
• Balcony/Terrace
• Security/Safety

• Orlando
• Colonialtown North

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From $326

         

10.0 (90 Reviews)

Apartment

Stylish Boutique Guest house in Winter Park

• Air Conditioner
• Parking
• TV

• Florida
• Fairvilla

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From $227

         

|

9.0 (4 Reviews)

House

2 MI to DT Orlando & Winter Park

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• College Park

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From $235

         

10.0 (32 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 $128

         

|

9.0 (3 Reviews)

Apartment

Affordable, convenient pet-friendly family space

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Maitland

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From $161

         

10.0 (27 Reviews)

Apartment

Mid Century Luxury, 1 block from Park Ave (#3)

• Air Conditioner
• Parking
• TV

• Orlando
• Winter Park

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From $293

         

|

9.0 (1 Review)

House

Spacious Modern Japandi Retreat - Winter Park

• Air Conditioner
• Parking
• Pet Friendly

• Orlando
• Winter Park

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From $167

         

10.0 (26 Reviews)

Villa

Top 1% College Park GuestHouse Villa/Oasis - Mins to DT ORL/Winter Park & Eola

• Air Conditioner
• Parking
• TV

• Orlando
• College Park

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From $450

         

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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★ Pro Tip: Floridarentalvacations makes it easy to compare the best listings on Floridarentalvacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Floridarentalvacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Winter Park Village.