Winter Park Villas - Vacation Rentals in Waialee Gulch
Condo
9.8
(
200 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1600 ft²
-
Oceanfront -
Hot Tub -
Parking -
Pool
US $1,285
/Night
7 Nights - $8,992
Apartment
9.0
(
9 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
548.96 ft²
-
Breakfast -
Parking
-
Pool
-
Kitchen
US $147
/Night
7 Nights - $1,029
Villa
9.4
(
118 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
-
Oceanfront
-
Parking
-
Pool
-
Spa
US $1,119
/Night
7 Nights - $7,835
House
9.8
(
140 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
2200 ft²
-
Parking
-
Ocean View -
Balcony/Terrace -
View
US $1,932
/Night
7 Nights - $13,526
Apartment
6.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $541
/Night
7 Nights - $3,790
House
9.8
(
114 Reviews
)
2 Bedrooms
3 Bathrooms
6 Guests
2500 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,665
/Night
7 Nights - $11,653
Condo
9.8
(
201 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1100 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $558
/Night
7 Nights - $3,909
Villa
10.0
(
130 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
5000 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $1,259
/Night
7 Nights - $8,813
Villa
10.0
(
268 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
810 ft²
-
Private Pool -
Oceanfront
-
Hot Tub
-
Parking
US $1,062
/Night
7 Nights - $7,435
Villa
9.8
(
224 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1546 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Breakfast
US $1,397
/Night
7 Nights - $9,776
House
9.4
(
226 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1500 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,083
/Night
7 Nights - $7,580
Condo
9.6
(
305 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1500 ft²
-
Breakfast
-
Parking
-
Pool
-
Spa
US $1,097
/Night
7 Nights - $7,679
Villa
9.8
(
142 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1546 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Breakfast
US $1,384
/Night
7 Nights - $9,687
Apartment
9.8
(
133 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
807 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Breakfast
US $884
/Night
7 Nights - $6,190
Condo
9.8
(
123 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1650 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $1,606
/Night
7 Nights - $11,242
Villa
9.8
(
118 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1698 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Breakfast
US $1,404
/Night
7 Nights - $9,831
Villa
9.8
(
107 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1698 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Breakfast
US $1,536
/Night
7 Nights - $10,750
House
9.4
(
157 Reviews
)
2 Bedrooms
4 Bathrooms
6 Guests
1055 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $731
/Night
7 Nights - $5,116
Condo
9.2
(
160 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
925 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $415
/Night
7 Nights - $2,908
House
10.0
(
25 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1100 ft²
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
US $777
/Night
7 Nights - $5,438
House
9.6
(
30 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
725 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $776
/Night
7 Nights - $5,433
Villa
9.2
(
9 Reviews
)
4 Bedrooms
3 Bathrooms
12 Guests
2505 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Breakfast
US $2,378
/Night
7 Nights - $16,649
★ 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 Waialee Gulch.
Weather in Waialee Gulch
View the weather forecast for Waialee Gulch before booking your Waialee Gulch Vacation Rentals to confirm your best time to go.
December - February
High 79°F Low 64°F
March - May
High 83°F Low 66°F
June - August
High 84°F Low 69°F
September - November
High 84°F Low 66°F
Waialee Gulch Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Waialee Gulch?
There are a lot of options in Waialee Gulch. If you plan on staying in the Waialee Gulch area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Waialee Gulch:
- Luxury Ocean Villa 217 at Turtle Bay! Ocean Front!
- Stunning Corner Villa, Ocean Views From Every Bed
- Immaculate Maintained TBay Condo
- Ocean Front Luxurious Villa
- 1 bedroom, walk to beach and resort, the perfect place to enjoy the North Shore
- In-Demand Ground Flr Largest 3BR Villa Steps to Beach + Pool + Jacuzzi
- Kawela Kai on the Beach
- Hale Pono- Oceanfront, private, gated, great views, AC, large property
- Rarely Available! Romantic Honeymoon Villa 120
- SUMMER REDUCED! Villa 302, King bed, Penthouse Lvl Ocean View Turtle Bay
How many vacation rentals are available in Waialee Gulch?
Currently, the total number of properties listed in 2026 is over 650 in the Waialee Gulch area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Waialee Gulch.
