Bespokeusatravel - Vacation Rentals in Winter Park

Property Image From $243
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Property Image From $481
         

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10.0 (122 Reviews)
House
  • 2497 ft² House
  • Parking
  • TV
  • Security/Safety
Property Image From $148
         

Property Image From $227
         

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8.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Pool
Property Image From $342
         

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9.0 (1 Review)
House
  • Parking
  • Breakfast
  • Child Friendly

Luxury Places to Stay in Winter Park

Over 2800+ Luxury Places to Stay in or Near Winter Park
Property Image From $4,105
         

New
House
  • Parking
  • TV
  • Bedding/Linens
Property Image From $3,854
         

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New
House
  • Security/Safety
  • Sports/Activities
  • Skiing

Top-Rated Vacation Rentals with a Pool in Winter Park

Over 1075+ Top-Rated Vacation Rentals with a Pool in or Near Winter Park

Pet-Friendly Vacation Rentals in Winter Park

Over 298+ Pet-Friendly Vacation Rentals in or Near Winter Park
Property Image From $1,008
         

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10.0 (2 Reviews)
House
  • Pet Friendly
  • Pool
  • Security/Safety
Property Image From $214
         

10.0 (35 Reviews)
Apartment
  • 1280 ft² Apartment
  • Parking
  • Pet Friendly
  • TV
Property Image From $337
         

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9.0 (101 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $339
         

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10.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility
Property Image From $320
         

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9.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Property Image From $944
         

Large Vacation Homes & Villas in Winter Park

Over 548+ Large Vacation Homes & Villas in or Near Winter Park
Property Image From $517
         

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New
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Property Image From $474
         

10.0 (31 Reviews)
House
  • 2799 ft² House
  • Parking
  • Pool
  • TV
Property Image From $540
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Pool
  • Balcony/Terrace
Property Image From $1,330
         

10.0 (1 Review)
House
  • Pool
  • Security/Safety
  • Sports/Activities

Wheelchair Accessible Vacation Homes in Winter Park

Over 492+ Wheelchair Accessible Vacation Homes in or Near Winter Park
Property Image From $1,429
         

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7.0 (1 Review)
Apartment
  • Parking
  • Pool
  • Wheelchair Accessible
Property Image From $351
         

10.0 (112 Reviews)
Condo
  • Parking
  • TV
  • Wheelchair Accessible
Property Image From $483
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Pool
  • Wheelchair Accessible
Property Image From $398
         

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New
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly
Property Image From $146
         

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New
House
  • Parking
  • Wheelchair Accessible
  • Child Friendly

Winter Park Varoom and Airbnb Places to Stay Under $200

Over 493+ Winter Park Varoom and Airbnb Places to Stay Under $200
Property Image From $181
         

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10.0 (3 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Property Image From $195
         

10.0 (95 Reviews)
Apartment
  • 1194 ft² Apartment
  • Parking
  • Pool
  • TV
Property Image From $139
         

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9.8 (97 Reviews)
Hotel
  • Parking
  • TV
  • Balcony/Terrace
Property Image From $178
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Accessibility
  • Transportation/Shuttle
Property Image From $195
         

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10.0 (1 Review)
House
  • Parking
  • Security/Safety
  • Sports/Activities
Property Image From $132
         

9.8 (108 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Winter Park

Over 1467+ Instantly Bookable Vacation Homes in or Near Winter Park
Property Image From $302
         

10.0 (27 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Property Image From $356
         

About Winter Park Vacation Rentals

With more than 2809 Winter Park vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Winter Park.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bespokeusatravel Winter Park, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Winter Park. Places to stay near Winter Park are 1093 ft² on average, with prices averaging $428 a night.

Bespokeusatravel makes it easy and safe to find and compare vacation rentals in Winter Park with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Winter Park

Type Count
Vacation Homes 1009
Holiday Apartments 469
Hotels with Suites 48
Ski Chalet Rentals 26
Cabin Rentals 12
Villas 3
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Winter Park

Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel 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.

Weather in Winter Park

View the weather forecast for Winter Park before booking your Winter Park Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F