Unplugged Weekend - 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 Beach Villas From US $1,169
         

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9.8 (194 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,590
         

10.0 (62 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Wailea-Makena

Over 1881+ Luxury Places to Stay in or Near Wailea-Makena
Wailea Beach Villas Resort by KBM From US $9,660
         

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New
Apartment
  • Air Conditioner
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  • Pool
ICONIC OCEANFRONT ESTATE IN WONDERFUL WAILEA, MAUI! From US $5,697
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Polo Beach Club POL-109 by KBM From US $5,655
         

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8.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool

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

Over 1672+ Top-Rated Vacation Rentals with a Pool in or Near Wailea-Makena
Romantic, Luxury, Sensual Retreat - Couples Only From US $479
         

10.0 (206 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,012
         

10.0 (205 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Ekahi 34F - Best Panoramic Ocean View! From US $938
         

10.0 (200 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Walk to Beach, Ocean Views, Relax by the Pool From US $1,567
         

10.0 (164 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Wailea-Makena

Over 12+ Pet-Friendly Vacation Rentals in or Near Wailea-Makena
Wailea Point heavenly sunsets in paradise. Minimum 30 days From US $1,450
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Wailea Sunset Condo - Ekolu #607 From US $524
         

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9.2 (7 Reviews)
House
  • 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
Four Seasons Resort Maui at Wailea From US $1,534
         

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9.1 (149 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Ho'omaha Kahakai - Your luxury Beach Vacation A Safe Place to Stay From US $4,500
         

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

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New
Villa
  • Air Conditioner
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  • Pet Friendly

Large Vacation Homes & Villas in Wailea-Makena

Over 190+ Large Vacation Homes & Villas in or Near Wailea-Makena
5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $408
         

Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

A 5-Star Estate, Large Groups, Luxury Living From US $1,798
         

10.0 (77 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Escape to Ho'olei – Ocean Views & Luxe Comfort From US $1,280
         

9.6 (80 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Wailea-Makena

Over 159+ Wheelchair Accessible Vacation Homes in or Near Wailea-Makena
Wailea Grand Champions 87 From US $348
         

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9.6 (30 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • Wheelchair Accessible
Grand Champions by KBM From US $2,359
         

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10.0 (3 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Very Best Deluxe Ocean View.Panoramic View.First Class! From US $1,384
         

10.0 (157 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wailea-Makena Vacation Rentals and Airbnb Places to Stay Under $200

Over 4+ Wailea-Makena Vacation Rentals and Airbnb Places to Stay Under $200
Treetop Studio 2nd floor, corner unit From US $189
         

9.8 (104 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Wailea-Makena

Over 1269+ Instantly Bookable Vacation Homes in or Near Wailea-Makena
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $546
         

Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $526
         

10.0 (135 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais! From US $790
         

9.8 (78 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Maui Family Owned & Managed - Wailea Grand Champions Villa From US $415
         

About Wailea-Makena Vacation Rentals

With more than 149 Wailea-Makena vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Unpluggedweekend 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 Unpluggedweekend 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 1536.3 ft² on average, with prices averaging US $1,344 a night.

Unpluggedweekend 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 67
Villas 23
Resorts 14
Vacation Homes 8
Hotels 1

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

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

Currently, the total number of properties listed in 2026 is over 149 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.