Owner Direct Vacation Rentals in Wailea-Makena

The Best Owner Direct Vacation Rentals in Wailea-Makena. Explore thousands of vacation home rentals, large cabins, and villas near Wailea-Makena

Ho'olei at Grand Wailea From US $2,512
         

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10.0 (4 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Luxurious Wailea Ocean Vistas From US $1,151
         

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10.0 (7 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Wailea Ekahi 21F From US $511
         

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10.0 (4 Reviews)
Apartment
  • Pool
  • Security/Safety
  • Guest Services
Elua 406 From US $803
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Wailea-Makena

Over 1866+ Luxury Places to Stay in or Near Wailea-Makena
Wailea Beach Villas WBV-PH 412 by KBM From US $9,660
         

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New
Apartment
  • Air Conditioner
  • Parking
  • Pool
DISCOUNTED OCTOBER Special - Oceanfront Private Home From US $6,641
         

10.0 (108 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
ICONIC OCEANFRONT ESTATE IN WONDERFUL WAILEA, MAUI! From US $6,633
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

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

Over 1697+ Top-Rated Vacation Rentals with a Pool in or Near Wailea-Makena
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,012
         

10.0 (199 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Romantic, Luxury, Sensual Retreat - Couples Only From US $578
         

10.0 (199 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Ekahi 34F - Best Panoramic Ocean View! From US $986
         

10.0 (189 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Wailea-Makena

Over 12+ Pet-Friendly Vacation Rentals in or Near Wailea-Makena
Wailea Sunset Condo - Ekolu #607 From US $400
         

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9.2 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wailea Point heavenly sunsets in paradise. Minimum 30 days From US $1,450
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Four Seasons Resort Maui at Wailea From US $1,408
         

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9.0 (148 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Wailea Ekolu #803 - Beautiful Ocean and Garden Views From US $333
         

10.0 (60 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Andaz Maui at Wailea Resort - A Concept by Hyatt From US $819
         

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8.3 (62 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Ho'omaha Kahakai - Your luxury Beach Vacation A Safe Place to Stay From US $4,500
         

The Villas at Fairmont Kea Lani From US $3,289
         

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8.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Wailea-Makena

Over 162+ 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
Hula On In to Beach House Chic Style, Click the Video tour below! From US $600
         

Wailea Grand Champions From US $348
         

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9.1 (39 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
PRIME WHALE SEASON DECEMBER 15-21 NOW AVAILABLE! From US $514
         

10.0 (135 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Premier Collection at Grand Champions Wailea - Limited-Time Half Off From US $785
         

Luxe Oceanview Hideaway on Wailea Old Blue Golf Course From US $399
         

10.0 (123 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Palms at Wailea From US $390
         

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8.5 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Wailea-Makena

Over 166+ Wheelchair Accessible Vacation Homes in or Near Wailea-Makena
Fairmont Kea Lani, Maui From US $814
         

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9.1 (147 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Polo Beach Club Vacation Rentals - APlus Resorts From US $1,895
         

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10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Pool
  • TV
Wailea Beach Resort - Marriott, Maui From US $641
         

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8.8 (253 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Ekolu Village From US $303
         

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8.4 (5 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Amazing Wailea Surf Villa: Luxury Condo - Owner Direct! From US $2,154
         

10.0 (85 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Hotel Wailea, Relais & Châteaux - Adults Only From US $858
         

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9.5 (148 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Wailea-Makena Varoom and Airbnb Places to Stay Under $200

Over 3+ Wailea-Makena Varoom and Airbnb Places to Stay Under $200

Instantly Bookable Vacation Homes in Wailea-Makena

Over 1251+ Instantly Bookable Vacation Homes in or Near Wailea-Makena
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais! From US $790
         

About Wailea-Makena Vacation Rentals

With more than 1875 Wailea-Makena vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect 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 Ownerdirect 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 1259.37 ft² on average, with prices averaging $1,047 a night.

Ownerdirect 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
Vacation Homes 254
Holiday Apartments 207
Villas 116
Hotels with Suites 21
Resorts 18
Cottages 6

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

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