Wailea Vacation Rentals

Wailea is a luxurious resort community located in the base of Mt. Haleakala on the south shore of the island. Here you will find several great white-sand beaches, including Wailea Beach, which was named "America's Best Beach" by Dr. Beach in 1999. Wailea is also one of the world's best golf destinations featuring three championship golf courses with breathtaking ocean views from every hole. So if you like to play golf, you will find Wailea a true paradise. There is a large selection of vacation rentals in Wailea, everything from condos to upscale villas. So start planning your Maui vacation today and find your perfect Wailea vacation rental below.

Browse Wailea Vacation Rentals by condo/hotel name:

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  • GORGEOUS OCEAN VIEW CASTAWAY COVE C201!

    State of Hawaii Transient Accommodations Tax License #TA-071-739-0848-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910071 Castaway Cove C201 is located on Maui island, ranked #1 Best Luxury Destination in...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay7  reviews
    from $2,295 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES!! OCEAN FRONT ROYAL ILIMA A201 AT WAILEA BEACH VILLAS!

    State of Hawaii Transient Accommodations Tax License #TA-094-662-2464-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910063 Royal Ilima A201 is located on Maui island, ranked #1 Best Luxury Destination in ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay6  reviews
    from $4,450 per night
      Book Now
  • OCEAN VIEWS! SANDCASTLES SUITE L509

    State of Hawaii Transient Accommodations Tax License #TA-094-662-2464-03. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910057 Sandcastles Suite L509 is located on Maui island, ranked #1 Best Luxury ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Wailea
    5 night min stay6  reviews
    from $3,150 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES!! OCEAN VIEWS! SANDY SURF K508!

    State of Hawaii Transient Accommodations Tax License #TA-120-405-4016-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910056 Sandy Surf K508 is located on Maui island, ranked #1 Best Luxury Destination in ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Wailea
    5 night min stay6  reviews
    from $2,450 per night
      Book Now
  • GROUND FLOOR GOLDEN MANDARIN POOL VILLA D102!

    State of Hawaii Transient Accommodations Tax License #TA-116-313-0880-02. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910076 Golden Mandarin Pool Villa D102 is located on Maui island, ranked #1 Best Luxury ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay8  reviews
    from $2,795 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES! OCEAN VIEWS! AQUA LANI J305!

    State of Hawaii Transient Accommodations Tax License #TA-122-323-9680-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910029 Aqua Lani J305 is located on Maui island, ranked #1 Best Luxury Destination in the...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay9  reviews
    from $2,195 per night
      Book Now
  • SEASPIRIT 811, ANDAZ WAILEA RESORT!

    State of Hawaii Transient Accommodations Tax License #TA-102-149-9392-01. County of Maui Short-Term Rental License #Hotel-Zoned Resort. Tax Map Key #210080670011 SeaSpirit Villa 811 is located on Maui island, ranked #1 Best Luxury Destination ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Wailea
    4 night min stay1  reviews
    from $2,650 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES! LUXURIOUS, RE-DECORATED COCO PALMS POOL VILLA D101!

    State of Hawaii Transient Accommodations Tax License #TA-140-050-6368-02. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910075 Coco Palms Pool Villa D101 is located on Maui island, ranked #1 Best Luxury ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay8  reviews
    from $3,383 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES! OCEAN VIEWS! BEAUTIFUL MODERN MAUI I404!

    State of Hawaii Transient Accommodations Tax License #TA-131-414-5280-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910040 Modern Maui I404 is located on Maui island, ranked #1 Best Luxury Destination in ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay4  reviews
    from $2,395 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES! BEAUTIFUL OCEAN VIEWS! BELLA LUNA D302!!

    State of Hawaii Transient Accommodations Tax License #TA-039-013-0176-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910080 Bella Luna D302 is located on Maui island, ranked #1 Best Luxury Destination in ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay4  reviews
    from $3,450 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES! GROUND FLOOR FLORAL GARDENS POOL VILLA G102!

    State of Hawaii Transient Accommodations Tax License #TA-126-119-1168-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910094 Floral Gardens Pool Villa G102 is located on Maui island, ranked #1 Best Luxury ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    HI> Wailea
    5 night min stay6  reviews
    from $2,395 per night
      Book Now
  • SPRING BREAK SPECIAL, SELECT DATES! OCEAN VIEWS AT MER ET SOLEIL K408 AT WAILEA BEACH VILLAS!!

    State of Hawaii Transient Accommodations Tax License #TA-182-491-7504-01. County of Maui Short-Term Rental License #Hotel Zoned Resort. Tax Map Key #210080910044 Mer Et Soleil K408 is located on Maui island, ranked #1 Best Luxury Destination in...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Wailea
    5 night min stay3  reviews
    from $3,195 per night
      Book Now
  • Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier

    Located on the third tier on the south side of the Ho’olei Resort on Maui, our two-level villa has jaw-dropping Pacific Ocean views and is perfectly perched to capture the crystal blue sky during the day and breathtaking sunsets in the ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    HI> Wailea
    3 night min stay36  reviews
    from $1,758 per night
      Book Now
  • Luxury Ocean View Penthouse surrounded by tropical oasis

    Wailea Beach Villas F202 is where luxury, style and sophistication blend together in a stunning Maui location just above Wailea Beach. This immaculate villa showcasing gorgeous blue ocean views while encompassed by lush tropical trees is sure to...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Wailea
    3 night min stay3  reviews
    from $2,044 per night
      Book Now
  • Luxury Penthouse minutes from Wailea Beach with panoramic ocean and island views

    Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bath penthouse villa with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Wailea
    3 night min stay3  reviews
    from $2,435 per night
      Book Now