Lakes Resorts - Vacation Rentals in Maui's Winery

Ho'olei at Grand Wailea From US $3,013
         

|
10.0 (5 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Fairmont Kea Lani Maui Villa Experience From US $4,105
         

|
9.8 (6 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Maui Resort Kihei 2 Bedroom Condo From US $1,386
         

New
Resort
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Upscale & Luxurious Oceanview Resort Vistas From US $689
         

|
10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Four Seasons Resort Maui at Wailea From US $908
         

|
9.6 (1002 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Ocean View Penthouse: Steps to Beach, Fast Wi-Fi From US $304
         

3.0 (2 Reviews)
Resort
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Ho‘olei Villas at Grand Wailea From US $2,497
         

|
9.6 (45 Reviews)
Resort
  • Air Conditioner
  • Pool
  • Designated Smoking Area
Wailea Ekahi Beach Front Resort Condo 1B/2B From US $313
         

New
Resort
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Fairmont Kea Lani Maui From US $1,229
         

|
9.4 (1011 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Grand Champion Villa Getaway - Wailea Beaches From US $275
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Koa Resort 4I From US $617
         

|
9.7 (3 Reviews)
House
  • Parking
  • Pool
  • View
Hotel Wailea, Relais & Chateaux - Adults Only From US $1,075
         

|
9.4 (1001 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Resort - Marriott, Maui From US $641
         

|
9.1 (253 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Resort - Marriott, Maui From US $1,083
         

|
9.2 (1012 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Four Seasons Resort Maui at Wailea From US $1,408
         

|
9.1 (149 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Andaz Maui at Wailea Resort - a concept by Hyatt From US $1,126
         

|
9.2 (1000 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Fairmont Kea Lani, Maui From US $1,168
         

|
9.1 (124 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Grand Champions From US $761
         

9.0 (4 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
2 2 Luxurious Wailea Oceanview Resort Vistas From US $1,882
         

|
9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Grand Wailea Maui, A Waldorf Astoria Resort From US $849
         

|
8.8 (1002 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Andaz Maui at Wailea Resort - A Concept by Hyatt From US $819
         

|
8.4 (59 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts 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 Maui's Winery.

Weather in Maui's Winery

View the weather forecast for Maui's Winery before booking your Maui's Winery 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

Maui's Winery Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Maui's Winery?
How many vacation rentals are available in Maui's Winery?

Currently, the total number of properties listed in 2026 is over 52 in the Maui's Winery area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Maui's Winery.