Winter Park Villas - Vacation Rentals in Main Square
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Kitchen -
Internet -
Child Friendly -
Laundry
US $77
/Night
7 Nights - $538
House
5.5
(
77 Reviews
)
3 Bedrooms
3 Bathrooms
5 Guests
96.88 ft²
-
Parking -
Balcony/Terrace -
Restaurant -
Bar
US $8
/Night
7 Nights - $55
Cabin
10.0
(
15 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Breakfast -
Parking
-
Balcony/Terrace
-
Internet
US $94
/Night
7 Nights - $657
Apartment
9.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Kitchen
-
Internet
-
Child Friendly
US $47
/Night
7 Nights - $326
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
3 Guests
129.17 ft²
-
Laundry
-
Sports/Activities -
Transportation/Shuttle -
Security/Safety
US $16
/Night
7 Nights - $112
Bed & Breakfast
10.0
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Internet
-
Child Friendly
US $218
/Night
7 Nights - $1,523
Apartment
6.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Pet Friendly
US $59
/Night
7 Nights - $411
House
8.0
(
21 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
-
Parking
-
Pet Friendly
-
Child Friendly
-
Bedding/Linens
US $22
/Night
7 Nights - $154
Ski Chalet
5 Bedrooms
4 Bathrooms
18 Guests
-
Hot Tub -
Air Conditioner -
Internet
-
Child Friendly
US $482
/Night
7 Nights - $3,374
House
7 Bedrooms
2 Bathrooms
10 Guests
1701 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
US $275
/Night
7 Nights - $1,925
Cottage
4 Bedrooms
4 Bathrooms
8 Guests
-
Internet
-
Pet Friendly
-
Bedding/Linens
-
Security/Safety
US $211
/Night
7 Nights - $1,477
House
4 Bedrooms
2 Bathrooms
10 Guests
-
Kitchen
-
Internet
-
Pet Friendly
-
Child Friendly
US $155
/Night
7 Nights - $1,088
Cabin
2 Bedrooms
1 Bathroom
4 Guests
-
Internet
-
Pet Friendly
-
Child Friendly
-
Bedding/Linens
US $137
/Night
7 Nights - $961
New
Apartment
2 Bedrooms
1 Bathroom
8 Guests
-
Child Friendly
-
Laundry
-
Toiletries -
Bedding/Linens
US $120
/Night
7 Nights - $840
Apartment
3 Bedrooms
3 Bathrooms
9 Guests
-
Kitchen
-
Internet
-
Pet Friendly
-
Child Friendly
US $114
/Night
7 Nights - $795
Apartment
3 Bedrooms
2 Bathrooms
8 Guests
-
Internet
-
Pet Friendly
-
Child Friendly
-
Laundry
US $101
/Night
7 Nights - $707
Apartment
3 Bedrooms
1 Bathroom
9 Guests
-
View -
Internet
-
Pet Friendly
-
Child Friendly
US $97
/Night
7 Nights - $682
Ski Chalet
1 Bedroom
2 Bathrooms
4 Guests
-
Internet
-
Bedding/Linens
-
Security/Safety
US $90
/Night
7 Nights - $630
Apartment
2 Bedrooms
1 Bathroom
6 Guests
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Pet Friendly
US $82
/Night
7 Nights - $574
Apartment
1 Bedroom
1 Bathroom
4 Guests
-
Internet
-
Child Friendly
-
Bedding/Linens
-
Wellness Facilities
US $73
/Night
7 Nights - $508
Apartment
2 Bedrooms
2 Bathrooms
5 Guests
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Pet Friendly
US $64
/Night
7 Nights - $449
Apartment
2 Bedrooms
2 Bathrooms
6 Guests
915 ft²
-
Balcony/Terrace
-
Kitchen
-
Internet
-
Pet Friendly
US $59
/Night
7 Nights - $411
New
Apartment
2 Bedrooms
1 Bathroom
7 Guests
-
Kitchen
-
Pet Friendly
-
Child Friendly
-
TV
US $52
/Night
7 Nights - $362
US $71
/Night
7 Nights - $500
★ Pro Tip: Winterparkvillas makes it easy to compare the best listings on Winterparkvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winterparkvillas 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 Main Square.
Weather in Main Square
View the weather forecast for Main Square before booking your Main Square Vacation Rentals to confirm your best time to go.
December - February
High 83°F Low 63°F
March - May
High 83°F Low 63°F
June - August
High 85°F Low 62°F
September - November
High 84°F Low 62°F
Main Square Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Main Square?
There are a lot of options in Main Square. If you plan on staying in the Main Square area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Main Square:
How many vacation rentals are available in Main Square?
Currently, the total number of properties listed in 2026 is over 425 in the Main Square area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Main Square.
