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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101-120 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 Hidden Gem Apartment
Map1400 yd from City Centre800 yd from Shops at Wailea
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Kihei Akahi C202 Condo Wailea
Map2.1 mi from City Centre500 yd from
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B-204 Haleakala Shores
Map1.9 mi from City Centre200 yd from
FromUS$ 451 /nightSelect
Beautiful Oceanview, Great Location Across The Beach
Map1.9 mi from City Centre
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Wailea Elua Village On Ulua Beach
Map600 yd from City Centre300 yd from Shops at Wailea
FromUS$ 1 204 /nightSelect
Kihei Surfside, #310 Condo
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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A-303 Haleakala Shores
Map1.9 mi from City Centre
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Kihei Surfside, #512 Condo
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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Kihei Surfside, #304 Condo
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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Kihei Akahi D-105
Map2.1 mi from City Centre
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Kihei Surfside, #213 Condo
Map1.4 mi from City Centre1.0 mi from Shops at Wailea
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Ocean View Penthouse: Steps To Beach, Fast Wi-Fi
Map2.0 mi from City Centre400 yd from
FromUS$ 1 946 /nightSelect
Ground Floor Garden View Unit With Great Amenities
Map2.1 mi from City Centre
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Maui Beachside Retreat
Map2.0 mi from City Centre400 yd from
FromUS$ 356 /nightSelect
Luxury Suite, Pool, Walk To Beach
Map2.0 mi from City Centre400 yd from
FromUS$ 400 /nightSelect
Makena Surf, #C-205 Condo
Map1.9 mi from City Centre500 yd from Makena Landing Beach Park
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Maui Banyan H404
Map2.0 mi from City Centre400 yd from
FromUS$ 331 /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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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