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Winter Park Vacation Rentals

Find 224 available offers from 8 partners
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1 guest
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Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $56 per night!

House Winter Park
Feb 10 - Feb 17
House ∙ 6 guests ∙ 3 bedrooms

Spacious House with 3 Rooms for 6 Persons

Winter Park, Orange County, Florida, United States
$220
per night
$220
per night
View deal
House Winter Park
Jan 9 - Jan 16
House ∙ 2 guests ∙ 1 bedroom

Vacation Home with Private Pool & Terrace

Winter Park, Orange County, Florida, United States
$133
per night
Outstanding(8 ratings)
$133
per night
View deal
House Winter Park
Jun 7 - Jun 14
House ∙ 3 guests ∙ 1 bedroom

Child-Friendly Nice Vacation Home with Private Pool, Terrace & Yard | Good for Workation | Pets Are Welcome

Winter Park, Orange County, Florida, United States
$105
per night
Outstanding(179 ratings)
$105
per night
View deal
House Winter Park
-42%
Mar 22 - Mar 29
House ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Vacation Home with Private Pool, Patio & Grill | Suitable for Remote Work

Winter Park, Orange County, Florida, United States
$359$215
per night
$359$215
per night
View deal
House Winter Park
Jun 23 - Jun 30
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home with Private Pool, BBQ & Terrace | Suitable for Remote Work

Winter Park, Orange County, Florida, United States
$329
per night
Outstanding(14 ratings)
$329
per night
View deal
House Winter Park
May 8 - May 15
Free cancellation
House ∙ 4 guests ∙ 2 bedrooms

Children-Friendly Pleasant Vacation Home

Winter Park, Orange County, Florida, United States
$267
per night
$267
per night
View deal
House Winter Park
Jan 9 - Jan 16
House ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Nice Vacation Home with Garden, Pool & Terrace

Winter Park, Orange County, Florida, United States
$232
per night
Outstanding(1 rating)
$232
per night
View deal
House Winter Park
Feb 26 - Mar 5
House ∙ 10 guests ∙ 5 bedrooms

Big Vacation Home with 5 Rooms for 10 Persons

Winter Park, Orange County, Florida, United States
$268
per night
Outstanding(10 ratings)
$268
per night
View deal
House Winter Park
Mar 22 - Mar 29
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Barbecue, Patio & Garden | Lake View | Perfect for Remote Work

Winter Park, Orange County, Florida, United States
$262
per night
Outstanding(27 ratings)
$262
per night
View deal
House Winter Park
Mar 22 - Mar 29
House ∙ 2 guests ∙ 1 bedroom

House with Grill, Garden & Private Pool | Suitable for Remote Work

Winter Park, Orange County, Florida, United States
$113
per night
$113
per night
View deal
Condo Winter Park
Mar 26 - Apr 2
Condo ∙ 6 guests ∙ 2 bedrooms

Condo with Pool & Patio

Winter Park, Orange County, Florida, United States
$171
per night
Outstanding(26 ratings)
$171
per night
View deal
Apartment Winter Park
Feb 22 - Mar 1
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment with Terrace | City View

Winter Park, Orange County, Florida, United States
$209
per night
Outstanding(38 ratings)
$209
per night
View deal
Apartment Winter Park
Feb 22 - Mar 1
Apartment ∙ 6 guests ∙ 1 bedroom

Holiday Apartment for 6 Persons

Winter Park, Orange County, Florida, United States
$179
per night
Outstanding
$179
per night
View deal
House Winter Park
Apr 26 - May 3
House ∙ 6 guests ∙ 4 bedrooms

Vacation Home with Yard, Grill & Terrace

Winter Park, Orange County, Florida, United States
$178
per night
Outstanding(159 ratings)
$178
per night
View deal
House Winter Park
Jan 7 - Jan 14
House ∙ 2 guests ∙ 1 bedroom

House with Private Pool | Good for Workation

Winter Park, Orange County, Florida, United States
$56
per night
$56
per night
View deal

Vacation Rentals With Fireplaces

House  Winter Park
Sep 14 - Sep 21
-45%
$796
$241
per night
House ∙ 8 guests ∙ 3 bedrooms

House with BBQ & Private Pool

Winter Park, Orange County, Florida, United States
Free cancellation
Fireplace
View deal
House  Winter Park
Jan 11 - Jan 18
-53%
$394
$148
per night
House ∙ 2 guests ∙ 3 bedrooms

Child-Friendly Spacious House

Winter Park, Orange County, Florida, United States
Free cancellation
Fireplace
View deal
House  Winter Park
Nov 30 - Dec 7
-67%
$399
$164
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-Friendly House with Grill, Garden & Pool

Winter Park, Orange County, Florida, United States
Fireplace
View deal
See all offers

Best Vacation Home Deals in Winter Park

Save up to 64%

House Winter Park
Sep 13 - Sep 20
-64%
$366
$131
per night
House ∙ 8 guests ∙ 4 bedrooms

Family-Friendly House with Grill, Garden & Pool

Winter Park, Orange County, Florida, United States
Free cancellation
View deal
House Winter Park
Jan 10 - Jan 17
-48%
$216
$113
per night
House ∙ 6 guests ∙ 4 bedrooms

House with Terrace & Garden | Nature View

Winter Park, Orange County, Florida, United States
View deal
House Winter Park
Feb 1 - Feb 8
-50%
$231
$116
per night
House ∙ 4 guests ∙ 2 bedrooms

Children-Friendly Nice Vacation Home | Perfect for Remote Work | Dogs Allowed

Winter Park, Orange County, Florida, United States
View deal

Explore the 224 offers listed in Winter Park and find a welcoming spot for a relaxing vacation. By directly analyzing these vacation rentals, HomeToGo highlights the most economical offers and the most popular vacation homes in Winter Park.

Budget-friendly Vacation Rentals in Winter Park

Find Fantastic yet Inexpensive Offers

Condo Winter Park
Feb 26 - Mar 5
$165
per night
Condo ∙ 4 guests ∙ 2 bedrooms

Nice Condo with Pool

Winter Park, Orange County, Florida, United States
View deal
House Winter Park
Jul 26 - Aug 2
$164
per night
House ∙ 7 guests ∙ 4 bedrooms

House with Private Pool, Barbeque & Terrace

4.8
Outstanding(36 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
Mar 22 - Mar 29
$221
per night
House ∙ 12 guests ∙ 3 bedrooms

Child-Friendly House with Private Pool & Terrace

4.4
Very good(36 ratings)
Winter Park, Orange County, Florida, United States
View deal

Top-Rated Rentals and Accommodations in Winter Park

Book Vacation Rental Offers with the Highest User Rating

House Winter Park
Mar 8 - Mar 15
$191
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Charming Vacation Home with Garden, BBQ & Patio | City View | Suitable for Remote Work

4.8
Outstanding(68 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
Jun 14 - Jun 21
$283
per night
House ∙ 12 guests ∙ 4 bedrooms

House with Patio, Private Pool & Barbeque

5.0
Outstanding(26 ratings)
Winter Park, Orange County, Florida, United States
View deal
House Winter Park
Mar 27 - Apr 3
$200
per night
House ∙ 6 guests ∙ 4 bedrooms

Family-Friendly Wonderful Vacation Home | Good for Workation | Pets Are Welcome

5.0
Outstanding(16 ratings)
Winter Park, Orange County, Florida, United States
View deal

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Find your dream stay

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Winter Park

  • Pool (72)
  • Pet-friendly (99)
  • WiFi (216)
  • Air conditioning (211)
  • Kitchen (141)
  • TV (186)
  • Parking (3)
  • Washing machine (82)
  • Microwave (107)
  • Dishwasher (44)
  • Balcony/patio (81)
  • Hot tub (5)

Finding a rental with a pool is easy in Winter Park. One-third of the accommodations offer pools. Also, more House rental have pools than any other type of property. They are a great choice if you go in a group of 9, as that is the number of people they can accommodate on average. Among these vacation rentals, 57 of them are within 2 miles of water.

Rent a condo, or vacation home in Winter Park, on Orlando's doorstep

Winter Park, Florida offers beautiful vacation homes in the greater Orlando area. The most common of these are fully equipped condos with decks, gardens, and all the amenities you could ask for. There are also lavish villas available, near the sea or within the city center. Another option for your upcoming vacation are expansive vacation homes with multiple bedrooms, bathrooms, and backyards.

What are the best activities for families in Winter Park?

Tons of fun for families, too

Kids will love the Saturday Farmer's Market in Winter Park, where you can buy vegetables directly from growers, or eat some freshly-popped popcorn. Right on Orlando's doorstep, Winter Park is also within reach of Orlando's Airheads Trampoline Arena, as well as the world-famous DIsney World. Another popular destination for families is the Petting Farm at Green Meadows Farm.

What are the best places to discover the arts and culture of Winter Park ?

Winter Park: historic and interesting sites

The Charles Hosmer Morse Museum of American Art is full of timely pieces both classic and modern. To encounter art outdoors, check out the Albin Polasek Museum & Sculpture Gardens. Cornell Fine Arts Museum offers more sophisticated art to enjoy. If you want to be immersed in Winter Park's history and culture, stop by the Winter Park Historical Museum, Casa Feliz Historic Home Museum, and the Hannibal Square Heritage Center.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 224 rentals
💳 Possible discounts up to 75%
🌙 Nightly prices starting at $56
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 100 homes
🏊 Vacation rentals with pools 72 homes
26,466 reviews
Winter Park vacation rentals have an average rating of 4.5/5 on 26,466 reviews left by travelers.

Frequently Asked Questions

What is the average nightly price for a vacation rental in Winter Park?

The price of a night's stay in Winter Park starts at $56. $263 is the average nightly price for house rentals in Winter Park. Apartment rentals in Winter Park cost $201 per night on average.

How many vacation rentals are available for booking in Winter Park?

There are currently 224 vacation rentals to choose from for your upcoming trip.

What amenities are most popular for vacation rentals in Winter Park?

If you're looking to book a vacation rental in Winter Park, others search for homes with Pool, Pets allowed and Internet.

How many vacation rentals with pools are there in Winter Park?

Winter Park has 72 Hotel room and Apartment rental options on offer to book.

Are pets allowed in vacation homes in Winter Park?

In case if you are traveling with a pet in Winter Park - 45% of vacation homes are pet-friendly.

When is it better to travel to Winter Park ?

Winter Park has its warmest time of year around July and August, with average nightly prices being around $56.

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