Winter Park Villas - Vacation Rentals in The Cherry Bowl
House
10.0
(
60 Reviews
)
5 Bedrooms
4 Bathrooms
20 Guests
-
Private Pool -
Hot Tub -
Parking -
Pool
US $787
/Night
7 Nights - $5,509
Cabin
7.4
(
479 Reviews
)
121 Bedrooms
1 Bathroom
14 Guests
301.39 ft²
-
Parking
-
Balcony/Terrace -
Air Conditioner -
Internet
US $81
/Night
7 Nights - $569
US $94
/Night
7 Nights - $657
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
12 Guests
2290 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $571
/Night
7 Nights - $3,994
New
House
5 Bedrooms
3 Bathrooms
15 Guests
86.11 ft²
-
Internet
-
Security/Safety
US $529
/Night
7 Nights - $3,703
Hotel
9.0
(
1002 Reviews
)
-
Hot Tub
-
Breakfast -
Parking
-
Pool
US $135
/Night
7 Nights - $947
Apartment
10.0
(
1 Review
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Kitchen -
Air Conditioner
-
Internet
US $133
/Night
7 Nights - $929
US $147
/Night
7 Nights - $1,028
House
9.8
(
28 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1888 ft²
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
US $221
/Night
7 Nights - $1,547
Cottage
9.8
(
15 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $238
/Night
7 Nights - $1,669
House
9.8
(
7 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
2694 ft²
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
US $453
/Night
7 Nights - $3,174
House
9.6
(
43 Reviews
)
9 Bedrooms
6 Bathrooms
25 Guests
8962 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $1,048
/Night
7 Nights - $7,337
Cabin
9.6
(
14 Reviews
)
3 Bedrooms
2 Bathrooms
10 Guests
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $573
/Night
7 Nights - $4,010
House
9.4
(
22 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $343
/Night
7 Nights - $2,400
House
9.4
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
11 Guests
2900 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $660
/Night
7 Nights - $4,622
Condo
4.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
2 Guests
850 ft²
-
Air Conditioner
-
Internet
-
Child Friendly -
Laundry
US $111
/Night
7 Nights - $774
New
House
5 Bedrooms
3 Bathrooms
15 Guests
-
Kitchen
-
Air Conditioner
-
Internet
-
Child Friendly
US $382
/Night
7 Nights - $2,675
House
10.0
(
12 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $400
/Night
7 Nights - $2,798
House
10.0
(
8 Reviews
)
3 Bedrooms
1 Bathroom
6 Guests
1100 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $353
/Night
7 Nights - $2,472
Villa
9.8
(
10 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1800 ft²
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
US $242
/Night
7 Nights - $1,695
Apartment
1 Bedroom
1 Bathroom
2 Guests
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $144
/Night
7 Nights - $1,009
Apartment
10.0
(
2 Reviews
)
2 Bedrooms
1 Bathroom
7 Guests
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $240
/Night
7 Nights - $1,679
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $221
/Night
7 Nights - $1,550
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
-
Breakfast
-
Parking
-
Pool
-
Kitchen
US $200
/Night
7 Nights - $1,398
★ 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 The Cherry Bowl.
Weather in The Cherry Bowl
View the weather forecast for The Cherry Bowl before booking your The Cherry Bowl 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
The Cherry Bowl Vacation Rental Frequently Asked Questions
What are the top vacation rentals in The Cherry Bowl?
There are a lot of options in The Cherry Bowl. If you plan on staying in the The Cherry Bowl area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in The Cherry Bowl:
- Entertainment Oasis Indoor Pool Spa Arcade Theatre
- A Mid-Century Modern Lovers Dream. Don't miss out on the Long House!
- Cozy, Welcoming, Tidy 3-bedroom house with pool table and EV charger in Rockford
- Pool, Arcade, Hot Tub and more @16th and Aldeen
- Pool. Free Breakfast. Your Next Vacation!
- Pool. Free Breakfast. Near Midway Village Museum!
- King Studio Suite w/Pool & Free Breakfast
- Vintage and Modern Cherry Valley Retreat
- BoutiqueVictorian*FamilyFriendly*VillageEats&Parks
- Charming 1-bedroom cottage in Cherry Valley - within walking distance to parks.
How many vacation rentals are available in The Cherry Bowl?
Currently, the total number of properties listed in 2026 is over 75 in the The Cherry Bowl area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Cherry Bowl.
