Winter Park Villas - Vacation Rentals in Maalaea Beach
Condo
10.0
(
224 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
702 ft²
-
Oceanfront -
Hot Tub -
Parking -
Pool
US $644
/Night
7 Nights - $4,509
Apartment
7.7
(
28 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
441.32 ft²
-
Parking
-
Pool
-
Internet -
Child Friendly
US $162
/Night
7 Nights - $1,134
Condo
9.8
(
6 Reviews
)
1 Bedroom
2 Bathrooms
3 Guests
813 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $680
/Night
7 Nights - $4,758
Condo
10.0
(
206 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
642 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $430
/Night
7 Nights - $3,012
Apartment
10.0
(
24 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
979.52 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $817
/Night
7 Nights - $5,716
Condo
9.8
(
30 Reviews
)
1 Bedroom
1 Bathroom
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $498
/Night
7 Nights - $3,486
Condo
10.0
(
203 Reviews
)
1 Bedroom
1 Bathroom
3 Guests
560 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $367
/Night
7 Nights - $2,570
Apartment
10.0
(
3 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
882.64 ft²
-
Private Beach -
Oceanfront
-
Breakfast -
Parking
US $414
/Night
7 Nights - $2,899
House
10.0
(
156 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
2000 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
US $855
/Night
7 Nights - $5,985
Condo
10.0
(
146 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
936 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $555
/Night
7 Nights - $3,888
Condo
10.0
(
143 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
700 ft²
-
Private Pool -
Hot Tub
-
Breakfast
-
Parking
US $615
/Night
7 Nights - $4,303
Condo
10.0
(
115 Reviews
)
2 Bedrooms
1 Bathroom
3 Guests
600 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $286
/Night
7 Nights - $2,001
Condo
9.8
(
269 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
600 ft²
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $292
/Night
7 Nights - $2,045
Condo
9.8
(
166 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
980 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $407
/Night
7 Nights - $2,852
US $701
/Night
7 Nights - $4,908
Condo
10.0
(
80 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
900 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $634
/Night
7 Nights - $4,440
New
Condo
9.8
(
137 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
650 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $250
/Night
7 Nights - $1,751
Condo
9.6
(
101 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
688 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $625
/Night
7 Nights - $4,378
Condo
10.0
(
124 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
885 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $568
/Night
7 Nights - $3,978
New
Condo
10.0
(
40 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
700 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $651
/Night
7 Nights - $4,558
Condo
9.8
(
226 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
885 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $459
/Night
7 Nights - $3,215
Condo
9.6
(
136 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
709 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $266
/Night
7 Nights - $1,860
Condo
9.6
(
84 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
900 ft²
-
Pool
-
Ocean View
-
Balcony/Terrace
-
View
US $774
/Night
7 Nights - $5,417
New
Condo
9.6
(
79 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
786 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $570
/Night
7 Nights - $3,993
★ 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 Maalaea Beach.
Weather in Maalaea Beach
View the weather forecast for Maalaea Beach before booking your Maalaea Beach 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
Maalaea Beach Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Maalaea Beach?
There are a lot of options in Maalaea Beach. If you plan on staying in the Maalaea Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Maalaea Beach:
- FALL IN LOVE WITH MAUI - OCEANFRONT FALL SPECIAL!
- Ocean Front Penthouse Best View Most Amenities Fully Stocked Feels like home
- On the Beach! Popular Unit A6, Gorgeous Remodel. An Ideal Location.
- Corner Unit With Views From Every Window-Awesome Reviews
- Amazing Oceanfront Condo, Tropical Luxury, Great Value, 2 BR, 2 Bath
- FALL SPECIAL-OCEANFRONT & HOTEL-ZONED
- Welcome to Azure Bay, luxury oceanfront condo
- Sugar Beach Maui! Direct Ocean Front! Best View! Best Value!
- Oceanfront Condo at Sugar Beach Resort- Stunning Sunsets and Beach Front
- The Maui Moon Oceanfront Condo- Perfect for couples!
How many vacation rentals are available in Maalaea Beach?
Currently, the total number of properties listed in 2026 is over 1510 in the Maalaea Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Maalaea Beach.
