Naramata Wineries - Vacation Rentals in Wailea-Makena

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

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10.0 (5 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Ekahi 21F From US $571
         

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10.0 (3 Reviews)
Apartment
  • Pool
  • Security/Safety
  • Guest Services
Wailea Elua Village 803, Ocean Views, Modern Reno From US $1,499
         

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10.0 (2 Reviews)
House
  • Parking
  • View
  • Ocean View
Elua 406 From US $803
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
WAILEA EKOLU, #914 From US $618
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Ekolu 911 From US $504
         

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10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

Polo Beach Club 604 by Coldwell Banker Island Vacations From US $1,336
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Wailea-Makena

Over 317+ Luxury Places to Stay in or Near Wailea-Makena
The Villas at Fairmont Kea Lani From US $3,289
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Wailea-Makena

Over 259+ Top-Rated Vacation Rentals with a Pool in or Near Wailea-Makena
9B EKAHI VILLAGE-STUDIO BATH, GARDEN VIEW - 1 MINUTE STROLL to BEACH! From US $263
         

WAILEA ELUA, #2501 From US $1,019
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Luxurious Wailea Ocean Vistas From US $804
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Beautifully remodeled ocean view condo in Wailea WE27B From US $748
         

Grand Champions Golf Villas 94 From US $744
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • View
Palms at Wailea 2104 by Coldwell Banker Island Vacations From US $504
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Wailea-Makena

Over 6+ Pet-Friendly Vacation Rentals in or Near Wailea-Makena
Wailea Sunset Condo - Ekolu #607 From US $524
         

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9.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Four Seasons Resort Maui at Wailea From US $1,534
         

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9.0 (145 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Andaz Maui at Wailea Resort - A Concept by Hyatt From US $819
         

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8.4 (59 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
AC Hotel by Marriott Maui Wailea From US $475
         

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8.3 (133 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Residence Inn by Marriott Maui Wailea From US $494
         

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8.1 (40 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Wailea-Makena

Over 37+ Large Vacation Homes & Villas in or Near Wailea-Makena
Ho'olei Unit 12-2, Close to Pool, Walk to Beach From US $995
         

10.0 (1 Review)
Villa
  • Parking
  • Security/Safety
  • Wellness Facilities
Premier Collection at Grand Champions Wailea - Limited-Time Half Off From US $785
         

Palms at Wailea Maui - Select Your Unit From US $580
         

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8.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Palms at Wailea From US $401
         

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7.9 (22 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Wailea Grand Champions - CoralTree Residence Collection From US $385
         

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7.0 (1 Review)
House
  • Parking
  • Pool
  • Security/Safety

Wheelchair Accessible Vacation Homes in Wailea-Makena

Over 9+ Wheelchair Accessible Vacation Homes in or Near Wailea-Makena
Wailea Grand Champions 87 From US $348
         

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9.6 (29 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Fairmont Kea Lani, Maui From US $1,168
         

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9.3 (114 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Resort - Marriott, Maui From US $653
         

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9.1 (253 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Ekolu Village 203 From US $438
         

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8.6 (5 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Wailea Grand Champions 149 From US $438
         

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New
Apartment
  • Pool
  • View
  • Wheelchair Accessible
Hotel Wailea, Relais & Châteaux - Adults Only From US $988
         

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9.3 (145 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

About Wailea-Makena Vacation Rentals

With more than 326 Wailea-Makena vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Naramatawineries and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Wailea-Makena.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Naramatawineries Wailea-Makena, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Wailea-Makena. Places to stay near Wailea-Makena are 1249.49 ft² on average, with prices averaging US $936 a night.

Naramatawineries makes it easy and safe to find and compare vacation rentals in Wailea-Makena with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Wailea-Makena

Type Count
Holiday Apartments 206
Vacation Homes 96
Villas 15
Resorts 6
Hotels 3

Use these Quick Filters to Find a Vacation Rental in Wailea-Makena

Pro Tip: Naramatawineries makes it easy to compare the best listings on Naramatawineries homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Naramatawineries 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 Wailea-Makena.

Weather in Wailea-Makena

View the weather forecast for Wailea-Makena before booking your Wailea-Makena 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

Wailea-Makena Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Wailea-Makena?

There are a lot of options in Wailea-Makena. If you plan on staying in the Wailea-Makena area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wailea-Makena:

How many vacation rentals are available in Wailea-Makena?

Currently, the total number of properties listed in 2026 is over 326 in the Wailea-Makena area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wailea-Makena.