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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61-80 out of 222
Sort by: high popularity
  • Price: low to high
  • Price: high to low
  • Guest rating: high to low
  • Popularity: high to low
Wailea Luxury Residence Hoolei 23-3
Map800 yd from City Centre900 yd from Wailea Gold Course
FromUS$ 1 228 /nightSelect
Wailea Ekolu 1106 Apartment
Map600 yd from City Centre600 yd from Wailea Tennis Club
FromUS$ 1 088 /nightSelect
Wailea Ekolu 1605
Map800 yd from City Centre800 yd from Wailea Tennis Club
FromUS$ 858 /nightSelect
Kihei Beach Retreat With Pool Access, Walk To Shore!
Map2.0 mi from City Centre400 yd from
FromUS$ 242 /nightSelect
Honu Sunset Steps To The Beach
Map1.5 mi from City Centre1.2 mi from Shops at Wailea
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Steps To Shore Kihei Beachgoers Condo With Pool!
Map2.0 mi from City Centre400 yd from
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Wailea Ekahi, #19A Condo
Map1200 yd from City Centre600 yd from Shops at Wailea
FromUS$ 1 258 /nightSelect
Mana Kai Maui Resort, #405C Condo
Map1.3 mi from City Centre1800 yd from Shops at Wailea
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Maui Kamaole, #I215 Condo
Map1.5 mi from City Centre1.2 mi from Shops at Wailea
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Hale Kamaole, #215 Condo
Map1.7 mi from City Centre300 yd from
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Kamaole Sands 8-204- Kihei Resort Condo, Ac, Across Street From Beach
Map1.8 mi from City Centre
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Maui Kamaole, #C-203 Condo
Map1.5 mi from City Centre1.2 mi from Shops at Wailea
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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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Kamaole Sands In Kihei, 1Br 2Ba, Near Beach, King Bed, Parking
Map1.8 mi from City Centre
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Polo Beach Club 205 By Coldwell Banker Island Vacations
Map1600 yd from City Centre1100 yd from Wailea Gold Course
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Mana Kai #412 By Coldwell Banker Island Vacations
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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Wailea Hidden Gem
Map1400 yd from City Centre800 yd from Shops at Wailea
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Beautiful Oceanview, Great Location Across The Beach
Map1.9 mi from City Centre
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A-303 Haleakala Shores
Map1.9 mi from City Centre
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Kihei Akahi D-105
Map2.1 mi from City Centre
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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