Vacation rentals in Wailea (Maui), United States

Carefully selected & verified rentals in Wailea (Maui), United States
Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room
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181-200 out of 222
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Kamaole Sands 8-204- Kihei Resort Condo, Ac, Across Street From Beach Wailea
Map1.8 mi from City Centre
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Wailea Elua, #2501 Condo
Map600 yd from City Centre300 yd from Shops at Wailea
FromUS$ 1 141 /nightSelect
Maui Banyan Q408A & Q408
Map2.0 mi from City Centre400 yd from
FromUS$ 431 /nightSelect
Wailea Elua Resort 1904
Map500 yd from City Centre400 yd from Shops at Wailea
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Maui Banyan B204
Map2.0 mi from City Centre400 yd from
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Maui Banyan H311 1Bd 2Ba 3 Min Walk To The Beach In The Heart Of South Kihei!
Map2.0 mi from City Centre400 yd from
FromUS$ 351 /nightSelect
Makena Surf, #G-103 Condo
Map1.9 mi from City Centre500 yd from Makena Landing Beach Park
FromUS$ 1 409 /nightSelect
Luxury Oceanfront Mana Kai Resort Condo
Map1.3 mi from City Centre1800 yd from Shops at Wailea
FromUS$ 1 338 /nightSelect
Kbm Resorts - 2 Free Cars - Grand Champions - Remodeled 5-Bedroom Multi-Unit Listing In The Heart Of Wailea Gch-120 Gch-134
Map700 yd from City Centre300 yd from Wailea Tennis Club
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Kbm Resorts Free Car Wailea Elua Village Wev-2103 Spacious With Ocean Views
Map600 yd from City Centre200 yd from Shops at Wailea
FromUS$ 845 /nightSelect
Perfect Getaway 2Bd Condo, Steps To Beach & Shops
Map1.7 mi from City Centre300 yd from
FromUS$ 662 /nightSelect
Mana Kai Resort, Luxury 2Bd/2Bath Beachfront # 511
Map1.3 mi from City Centre1800 yd from Shops at Wailea
FromUS$ 1 335 /nightSelect
Beachside Retreat With High-Speed Wi-Fi And Pool
Map2.0 mi from City Centre400 yd from
FromUS$ 466 /nightSelect
Wailea Elua, #2107 Condo
Map600 yd from City Centre300 yd from Shops at Wailea
Select
Grand Champion Villa Getaway - Wailea Beaches
Map600 yd from City Centre300 yd from Wailea Tennis Club
FromUS$ 385 /nightSelect
Ola Mahalo
Map1.5 mi from City Centre1.2 mi from Shops at Wailea
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Luxurious Wailea Ocean Vistas
Map400 yd from City Centre400 yd from Wailea Tennis Club
FromUS$ 530 /nightSelect
Wailea Oceanfront Rental
Map1200 yd from City Centre600 yd from Shops at Wailea
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A-312 Haleakala Shores
Map1.9 mi from City Centre200 yd from
FromUS$ 561 /nightSelect
Coneniently Located Two Bedroom Two Bath Hk319
Map1.7 mi from City Centre300 yd from
FromUS$ 793 /nightSelect

Flexible Price Range for Vacation Homes in Wailea (Maui)

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 6 716
⬇️ The lowest price
US$ 140
đź’¸ Average price for
5-star hotels
US$ 904
4-star hotels
US$ 748
3-star hotels
US$ 597
Apartments
US$ 755

Top vacation homes in Wailea (Maui)

Based on guest reviews from the past 12 months

Oceanview Escapes:
Beautiful 2 Bedroom Oceanview Condo At Maui Kamaole Located At South End Of Kihei Adjacent To Wailea Traditional Hawaiian Style
Chic Modern Retreats:
Aloha Moon - A Chic And Dreamy Modern Tropical Hideaway!
Tropical Family Getaways:
Wailea Elua Village - Coraltree Residence Collection
Beachfront Bliss:
Wailea Beach Villas
Garden View Serenity:
Kihei Akahi Garden View Studio
Luxury Oceanfront Offers:
Wailea Oceanfront Rental
Unique Bohemian Hideaways:
Tiki Tiki - Gorgeous Boho Beach Hideaway!
Cultural Charm and Convenience:
Kihei Akahi C320- Kihei Studio, Walk To Shops, Dining, & The Beach
Cozy Waterfront Retreats:
Maui Banyan T-305

Vacation Rentals in Wailea (Maui) Overview

This guide provides essential details about vacation rentals in Wailea (Maui), evaluating 50 properties to assist travelers in making informed accommodation choices.

Typical nightly rates range from $200 to $800.

Over 50 vacation rentals are available in Wailea.

Peak seasons include December to April.

Expect local taxes/fees around 14% on rentals.

Properties are within 1-2 miles of Wailea Beach and shops.

Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room