Lakes Resorts - Vacation Rentals in Wailea

Wailea Ekahi Beach Front Resort Condo 1B/2B From US $313
         

New
Resort
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Ho'olei at Grand Wailea From US $3,013
         

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10.0 (5 Reviews)
Resort
  • Air Conditioner
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  • Pool
Fairmont Kea Lani Maui Villa Experience From US $4,449
         

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9.8 (6 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
         

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10.0 (2 Reviews)
House
  • Parking
  • Pool
  • View
Four Seasons Resort Maui at Wailea From US $1,187
         

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9.6 (1003 Reviews)
Resort
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  • Parking
  • Pool
Fairmont Kea Lani, Maui From US $1,168
         

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9.3 (112 Reviews)
Resort
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  • Pool
Fairmont Kea Lani Maui From US $1,304
         

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9.4 (1000 Reviews)
Resort
  • Air Conditioner
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  • Pool

Luxury Places to Stay in Wailea

Over 1826+ Luxury Places to Stay in or Near Wailea
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New
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Polo Beach Club POL-109 by KBM From US $9,471
         

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8.0 (1 Review)
Condo
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  • Pool
Wailea Elua Village Resort by KBM From US $9,199
         

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New
Condo
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ICONIC OCEANFRONT ESTATE IN WONDERFUL WAILEA, MAUI! From US $5,335
         

10.0 (7 Reviews)
House
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  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Wailea

Over 1620+ Top-Rated Vacation Rentals with a Pool in or Near Wailea
Romantic, Luxury, Sensual Retreat - Couples Only From US $588
         

10.0 (207 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,138
         

10.0 (206 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Very Best Deluxe Ocean View.Panoramic View.First Class! From US $1,262
         

10.0 (158 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Wailea

Over 11+ Pet-Friendly Vacation Rentals in or Near Wailea
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
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  • Parking
  • Pet Friendly
Wailea Ekolu #803 - Beautiful Ocean and Garden Views From US $333
         

10.0 (60 Reviews)
Condo
  • 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 $902
         

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

Large Vacation Homes & Villas in Wailea

Over 182+ Large Vacation Homes & Villas in or Near Wailea
Hoolei 24-4 by Coldwell Banker Island Vacations From US $1,798
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,383
         

10.0 (62 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $480
         

Wheelchair Accessible Vacation Homes in Wailea

Over 144+ Wheelchair Accessible Vacation Homes in or Near Wailea
Wailea Beach Resort - Marriott, Maui From US $738
         

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8.9 (249 Reviews)
Resort
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  • Parking
  • Pool
Grand Champions by KBM From US $4,484
         

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10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
A 5-Star Estate, Large Groups, Luxury Living From US $1,529
         

10.0 (77 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Wailea Vacation Rentals and Airbnb Places to Stay Under $200

Over 3+ Wailea Vacation Rentals and Airbnb Places to Stay Under $200

Instantly Bookable Vacation Homes in Wailea

Over 1245+ Instantly Bookable Vacation Homes in or Near Wailea
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $684
         

Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $545
         

10.0 (137 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachfront Condo B303 June 27-July 3rd still available . From US $1,112
         

10.0 (101 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Maui Family Owned & Managed - Wailea Grand Champions Villa From US $463
         

Wailea Ekahi 51F Oceanview - Walk to Beach From US $444
         

9.8 (109 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About Wailea Vacation Rentals

With more than 41 Wailea vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Lakesresorts 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 Lakesresorts 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 1427.83 ft² on average, with prices averaging US $1,892 a night.

Lakesresorts 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 16
Vacation Homes 3

Use these Quick Filters to Find a Vacation Rental in Wailea

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 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?

There are a lot of options in Wailea. If you plan on staying in the Wailea 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:

How many vacation rentals are available in Wailea?

Currently, the total number of properties listed in 2026 is over 41 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.