Winter Park, FL Vacation Rentals

Top vacation rentals in Winter Park

10.0 / 10.0

Outstanding(101 Ratings)

Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts

House

in Winter Park

10 guests · 4 bedrooms · 2 baths

Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winter Park, at $251 per night for your next great vacation.

$$$$

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7.7 / 10.0

Very good(428 Ratings)

Comfort Suites Downtown

Hotel

in Orlando

3star

1 sofa bed, 2 full beds

Pool · Kitchen or Kitchenette · Air conditioner

Most favorited

Looking for the perfect place to call home during your trip to Winter Park? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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7.9 / 10.0

Very good(355 Ratings)

Park Plaza Hotel Orlando - Winter Park

Hotel

in Orlando

3star

1 queen bed

Garden · Pets allowed · Air conditioner

The best choice in Winter Park for Hotel, for $94 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$

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9.2 / 10.0

Outstanding(3 Ratings)

Winter Park charm

Bed and Breakfast

in Orlando

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Looking for a Bed and Breakfast in Winter Park, this Bed and Breakfast for $94 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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Campground/ RV Resort

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Explore vacation rentals with the most popular amenities in Winter Park

Vacation rentals with air conditioning in Winter Park

9.8 / 10.0

Outstanding(98 Ratings)

Casa Winter Park

House

in Winter Park

8 guests · 4 bedrooms · 4 baths

Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Winter Park, at $395 per night for your next great vacation.

$$$$

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WFH Friendly College Park Cottage in Orlando!

House

in Orlando

Pets allowed · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at WFH Friendly College Park Cottage in Orlando!, our elegant House in Winter Park. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

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8.8 / 10.0

Excellent(163 Ratings)

SpringHill Suites by Marriott Winter Park

Hotel

in Orlando

3star

1 futon, 2 queen beds

Garden · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Winter Park at SpringHill Suites by Marriott Winter Park for $94 for your next trip.

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9.9 / 10.0

Outstanding(71 Ratings)

Stylish Boutique Guest house in Historic Winter Park.

Apartment

in Winter Park

4 guests · 3 bedrooms · 1 bath

Garden · Pool · Kitchen or Kitchenette

Nestled in Winter Park, this Apartment is perfect for your next vacation. Enjoy Stylish Boutique Guest house in Historic Winter Park. 's top-rated amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$

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Winter Park

Winter Park travel guide

Let us help you plan your perfect Winter Park vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Winter Park, and more.