Park City Resort Rentals - Vacation Rentals in Wailea

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

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10.0 (5 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Fairmont Kea Lani Maui Villa Experience From US $5,399
         

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9.8 (6 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Ekahi Beach Front Resort Condo 1B/2B From US $313
         

New
Resort
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Koa Resort 4I From US $617
         

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9.7 (3 Reviews)
House
  • Parking
  • Pool
  • View
Fairmont Kea Lani Maui From US $1,672
         

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9.4 (1001 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Grand Champion Villa Getaway - Wailea Beaches From US $275
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Fairmont Kea Lani, Maui From US $1,168
         

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9.3 (113 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Wailea

Over 1868+ Luxury Places to Stay in or Near Wailea

Top-Rated Vacation Rentals with a Pool in Wailea

Over 1665+ Top-Rated Vacation Rentals with a Pool in or Near Wailea
Romantic, Luxury, Sensual Retreat - Couples Only From US $499
         

10.0 (207 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Walk to Beach, Ocean Views, Relax by the Pool From US $1,389
         

10.0 (167 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $695
         

Pet-Friendly Vacation Rentals in Wailea

Over 12+ Pet-Friendly Vacation Rentals in or Near Wailea
Wailea Sunset Condo - Ekolu #607 From US $524
         

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9.2 (7 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 $1,534
         

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9.0 (141 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 $902
         

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7.5 (58 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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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Wailea on PetFriendly.io

Large Vacation Homes & Villas in Wailea

Over 183+ Large Vacation Homes & Villas in or Near Wailea
Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,465
         

10.0 (62 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $382
         

Wheelchair Accessible Vacation Homes in Wailea

Over 149+ Wheelchair Accessible Vacation Homes in or Near Wailea
Grand Wailea Maui, A Waldorf Astoria Resort From US $998
         

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8.8 (1006 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Wailea Beach Resort - Marriott, Maui From US $738
         

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9.0 (252 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Amazing Wailea Surf Villa: Luxury Condo - Owner Direct! From US $2,569
         

10.0 (85 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachfront penthouse w/direct beach access and pool From US $1,258
         

10.0 (66 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wailea Vacation Rentals and Airbnb Places to Stay Under $200

Over 4+ Wailea Vacation Rentals and Airbnb Places to Stay Under $200
Treetop Studio 2nd floor, corner unit From US $188
         

9.8 (105 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Wailea

Over 1262+ Instantly Bookable Vacation Homes in or Near Wailea
Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $575
         

10.0 (136 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachfront Condo B303 From US $1,088
         

10.0 (99 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About Wailea Vacation Rentals

With more than 42 Wailea vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Parkcityresortrentals 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.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Parkcityresortrentals Wailea, 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. Places to stay near Wailea are 1429.55 ft² on average, with prices averaging US $1,888 a night.

Parkcityresortrentals makes it easy and safe to find and compare vacation rentals in Wailea 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

Type Count
Holiday Apartments 22
Resorts 17
Vacation Homes 3

Use these Quick Filters to Find a Vacation Rental in Wailea

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

Weather in Wailea

View the weather forecast for Wailea before booking your Wailea 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 Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Wailea?
How many vacation rentals are available in Wailea?

Currently, the total number of properties listed in 2026 is over 42 in the Wailea area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wailea.