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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221-222 out of 222
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Kihei Surfside, #512 Condo Wailea
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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Kihei Surfside, #304 Condo Wailea
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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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