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Top 30 Best Wailea vacation rentals with pool in Hawaii

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  • 1
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  • 4.9 223
    #1

    Ho‘olei Villas at Grand Wailea

    ● Open
    146 Hoolei Cir, Wailea, HI 96753, United States
    (808) 856-2000
    grandwailea.com

    Ho‘olei Villas at Grand Wailea is a luxurious lodging institution located at 146 Hoolei Circle in Wailea-Makena, Hawaii, United States. This upscale villa offers spacious and beautifully appointed accommodations with stunning views of the surrounding area.

    Photo of Ho‘olei Villas at Grand Wailea - 146 Hoolei Circle, Wailea-Makena, HI 96753, USA Photo of Ho‘olei Villas at Grand Wailea - 146 Hoolei Circle, Wailea-Makena, HI 96753, USA Photo of Ho‘olei Villas at Grand Wailea - 146 Hoolei Circle, Wailea-Makena, HI 96753, USA
    Lodging Business
    Details
  • 4.9 165
    #2

    Wailea Ekahi Village Pauli Family Rentals

    ● Closed
    3300 Wailea Alanui Dr APT 11E, Wailea, HI 96753, United States
    (808) 868-4050
    waileaekahivillage.com

    Wailea Ekahi Village Pauli Family Rentals is a reputable real estate agency located at 3300 Wailea Alanui Drive in the beautiful Wailea-Makena area of Hawaii, United States.

    Photo of Wailea Ekahi Village Pauli Family Rentals - 3300 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Ekahi Village Pauli Family Rentals - 3300 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Ekahi Village Pauli Family Rentals - 3300 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Real Estate Agent
    Details
  • 4.9 54
    #3

    Ekahi Vacation Condos

    ● Closed
    3300 Wailea Alanui Dr, Kihei, HI 96753, United States
    (403) 608-2034
    ekahivacationcondos.com

    Ekahi Vacation Condos is a real estate and travel agency located at 3300 Wailea Alanui Drive in Kihei, Hawaii. Our modern and spacious beachfront vacation rental condos in Wailea Ekahi Village on Maui offer all the comforts of home.

    Photo of Ekahi Vacation Condos - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Ekahi Vacation Condos - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Ekahi Vacation Condos - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 4.7 221
    #4

    Wailea Elua Village, CoralTree Residence Collection

    ● Open
    3600 Wailea Alanui Dr, Wailea, HI 96753, United States
    (833) 969-1254
    coraltreeresidencecollection.com

    Located at 3600 Wailea Alanui Drive in Wailea-Makena, Hawaii, the Wailea Elua Village, CoralTree Residence Collection offers a luxurious lodging experience like no other.

    Photo of Wailea Elua Village, CoralTree Residence Collection - 3600 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Elua Village, CoralTree Residence Collection - 3600 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Elua Village, CoralTree Residence Collection - 3600 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Lodging Business
    Details
  • 4.7 35
    #5

    Wailea Point Village

    ● Closed
    4000 Wailea Alanui Dr APT 100, Wailea, HI 96753, United States
    (808) 879-6106
    waileapoint.org

    Wailea Point Village is a luxurious oceanfront condominium complex located at 4000 Wailea Alanui Drive in Wailea-Makena, Hawaii, United States. This exclusive community offers stunning views of the Pacific Ocean and access to pristine beaches.

    Photo of Wailea Point Village - 4000 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Point Village - 4000 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Point Village - 4000 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Details
  • 4.6 2,051
    #6

    Andaz Maui At Wailea Resort - a Concept by Hyatt

    ● Open
    3550 Wailea Alanui Dr, Wailea, HI 96753, United States
    (808) 573-1234
    hyatt.com

    Andaz Maui At Wailea Resort - a Concept by Hyatt is a luxurious lodging destination located at 3550 Wailea Alanui Drive in the beautiful town of Wailea-Makena, Hawaii, United States.

    Photo of Andaz Maui At Wailea Resort - a Concept by Hyatt - 3550 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Andaz Maui At Wailea Resort - a Concept by Hyatt - 3550 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Andaz Maui At Wailea Resort - a Concept by Hyatt - 3550 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Lodging Business
    Details
  • 4.6 4,689
    #7

    Grand Wailea, A Waldorf Astoria Resort

    ● Open
    3850 Wailea Alanui Dr, Wailea, HI 96753, United States
    (808) 875-1234
    grandwailea.com

    Grand Wailea, A Waldorf Astoria Resort is a luxurious lodging institution located at 3850 Wailea Alanui Drive in Wailea-Makena, Hawaii, United States. This stunning resort offers world-class amenities and services in a breathtaking tropical setting.

    Photo of Grand Wailea, A Waldorf Astoria Resort - 3850 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Grand Wailea, A Waldorf Astoria Resort - 3850 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Grand Wailea, A Waldorf Astoria Resort - 3850 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Lodging Business
    Details
  • 4.6 3,709
    #8

    Wailea Beach Resort - Marriott, Maui

    ● Open
    3700 Wailea Alanui Dr, Wailea, HI 96753, United States
    (808) 879-1922
    marriott.com

    Wailea Beach Resort - Marriott, Maui is a luxurious lodging institution situated at 3700 Wailea Alanui Drive in Wailea-Makena, Hawaii, United States.

    Photo of Wailea Beach Resort - Marriott, Maui - 3700 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Beach Resort - Marriott, Maui - 3700 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Beach Resort - Marriott, Maui - 3700 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Lodging Business
    Details
  • 4.6 980
    #9

    Residence Inn by Marriott Maui Wailea

    ● Open
    75 Wailea Ike Dr, Wailea, HI 96753, United States
    (808) 891-7460
    marriott.com

    The Residence Inn by Marriott Maui Wailea is a luxurious lodging option located at 75 Wailea Ike Drive in the beautiful Wailea-Makena region of Hawaii.

    Lodging Business
    Details
  • 4.6 409
    #10

    Wailea Ekahi Village - A CoralTree Residence Collection

    ● Closed
    3300 Wailea Alanui Dr, Kihei, HI 96753, United States
    (844) 524-6123
    coraltreeresidencecollection.com

    Wailea Ekahi Village - A CoralTree Residence Collection is a stunning lodging option located at 3300 Wailea Alanui Drive in Kihei, Hawaii.

    Photo of Wailea Ekahi Village - A CoralTree Residence Collection - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Wailea Ekahi Village - A CoralTree Residence Collection - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Wailea Ekahi Village - A CoralTree Residence Collection - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA
    Lodging Business Real Estate Agent Travel Agency
    Details
  • 4.6 244
    #11

    Wailea Ekolu Village - A CoralTree Residence Collection

    ● Closed
    10 Wailea Ekolu Pl, Kihei, HI 96753, United States
    (844) 528-8545
    coraltreeresidencecollection.com

    Wailea Ekolu Village - A CoralTree Residence Collection is a luxurious lodging option located at 10 Wailea Ekolu Place in Kihei, Hawaii.

    Photo of Wailea Ekolu Village - A CoralTree Residence Collection - 10 Wailea Ekolu Place, Kihei, HI 96753, USA Photo of Wailea Ekolu Village - A CoralTree Residence Collection - 10 Wailea Ekolu Place, Kihei, HI 96753, USA Photo of Wailea Ekolu Village - A CoralTree Residence Collection - 10 Wailea Ekolu Place, Kihei, HI 96753, USA
    Lodging Business Real Estate Agent Travel Agency
    Details
  • 4.6 357
    #12

    Wailea Grand Champions - CoralTree Residence Collection

    ● Closed
    155 Wailea Ike Pl, Wailea, HI 96753, United States
    (844) 535-4128
    coraltreeresidencecollection.com

    Wailea Grand Champions - CoralTree Residence Collection is a luxurious lodging destination located at 155 Wailea Ike Place in the beautiful Wailea-Makena area of Hawaii, United States.

    Photo of Wailea Grand Champions - CoralTree Residence Collection - 155 Wailea Ike Place, Wailea-Makena, HI 96753, USA Photo of Wailea Grand Champions - CoralTree Residence Collection - 155 Wailea Ike Place, Wailea-Makena, HI 96753, USA Photo of Wailea Grand Champions - CoralTree Residence Collection - 155 Wailea Ike Place, Wailea-Makena, HI 96753, USA
    Lodging Business Real Estate Agent Travel Agency
    Details
  • 4.1 46
    #13

    Maui Rental Group

    ● Closed
    161 Wailea Ike Pl B107, Kihei, HI 96753, United States
    (808) 379-3208
    mauirental.com

    Maui Rental Group is a premier real estate and travel agency located at 161 Wailea Ike Place in Kihei, Hawaii.

    Photo of Maui Rental Group - 161 Wailea Ike Place, Kihei, HI 96753, USA Photo of Maui Rental Group - 161 Wailea Ike Place, Kihei, HI 96753, USA Photo of Maui Rental Group - 161 Wailea Ike Place, Kihei, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 5 2
    #14

    Wailea Ekolu Village Buildings 10-12

    ● Open
    Unnamed Road, 10 Wailea Ekolu Pl, Kihei, HI 96753, United States
    (808) 879-2222
    waileaekoluaoao.com

    Wailea Ekolu Village Buildings 10-12 is a charming residential complex located at 10 Wailea Ekolu Place in Kihei, Hawaii. The buildings are surrounded by lush tropical landscaping and offer stunning views of the ocean and nearby golf courses.

    Photo of Wailea Ekolu Village Buildings 10-12 - 10 Wailea Ekolu Place, Kihei, HI 96753, USA Photo of Wailea Ekolu Village Buildings 10-12 - 10 Wailea Ekolu Place, Kihei, HI 96753, USA Photo of Wailea Ekolu Village Buildings 10-12 - 10 Wailea Ekolu Place, Kihei, HI 96753, USA
    Details
  • 5 14
    #15

    Our Maui Condos | Wailea and Kihei Vacation Rentals

    ● Closed
    10 Wailea Ekolu Pl, Wailea, HI 96753, United States
    (970) 948-1701
    ourmauicondos.com

    Our Maui Condos offers beautiful vacation rentals in Kihei and Wailea, with stunning ocean views and all the comforts of home.

    Photo of Our Maui Condos | Wailea and Kihei Vacation Rentals - 10 Wailea Ekolu Place, Wailea-Makena, HI 96753, USA Photo of Our Maui Condos | Wailea and Kihei Vacation Rentals - 10 Wailea Ekolu Place, Wailea-Makena, HI 96753, USA Photo of Our Maui Condos | Wailea and Kihei Vacation Rentals - 10 Wailea Ekolu Place, Wailea-Makena, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 5 1
    #16

    The Palms at Wailea 1304

    ● Open
    3200 Wailea Alanui Dr Unit 1304, Wailea, HI 96753, United States
    (808) 938-0141
    airbnb.com

    The Palms at Wailea 1304 is a luxurious vacation rental property located at 3200 Wailea Alanui Drive in the beautiful Wailea-Makena region of Hawaii, United States.

    Photo of The Palms at Wailea 1304 - 3200 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of The Palms at Wailea 1304 - 3200 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of The Palms at Wailea 1304 - 3200 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 5 2
    #17

    Maui Resort Rentals – Wailea Village

    ● Closed
    100 Wailea Ike Dr #6, Kihei, HI 96753, United States
    (808) 909-3930
    mauiresortrentals.com

    Maui Resort Rentals - Wailea Village is a premier real estate and travel agency located at 100 Wailea Ike Drive in Kihei, Hawaii. Offering luxurious vacation rentals in the beautiful Wailea Village, guests can experience the ultimate Hawaiian getaway.

    Photo of Maui Resort Rentals – Wailea Village - 100 Wailea Ike Drive, Kihei, HI 96753, USA Photo of Maui Resort Rentals – Wailea Village - 100 Wailea Ike Drive, Kihei, HI 96753, USA Photo of Maui Resort Rentals – Wailea Village - 100 Wailea Ike Drive, Kihei, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 4.7 10
    #18

    The Palms at Wailea 2204

    ● Open
    3200 Wailea Alanui Dr #2204, Wailea, HI 96753, United States
    (650) 799-1389
    homeyhawaii.com

    The Palms at Wailea 2204 is a luxurious lodging located at 3200 Wailea Alanui Drive in the beautiful town of Wailea-Makena, Hawaii. This institution offers stunning accommodations with breathtaking ocean views, spacious rooms, and top-notch amenities.

    Photo of The Palms at Wailea 2204 - 3200 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of The Palms at Wailea 2204 - 3200 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of The Palms at Wailea 2204 - 3200 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Lodging Business
    Details
  • 4.6 8
    #19

    Wailea Resort Association

    ● Closed
    555 Kaukahi St, Wailea, HI 96753, United States
    (808) 874-6866
    wailearesortassociation.com

    The Wailea Resort Association is a premier lodging and travel agency located at 555 Kaukahi Street in Wailea-Makena, Hawaii.

    Photo of Wailea Resort Association - 555 Kaukahi Street, Wailea-Makena, HI 96753, USA Photo of Wailea Resort Association - 555 Kaukahi Street, Wailea-Makena, HI 96753, USA Photo of Wailea Resort Association - 555 Kaukahi Street, Wailea-Makena, HI 96753, USA
    Lodging Business Travel Agency
    Details
  • 4.8 113
    #20

    Wailea Beach Park

    ● Closed
    Kihei, HI 96753, United States
    (808) 879-4364
    mauicounty.gov

    Wailea Beach Park is a beautiful seaside park located in Kihei, Hawaii, United States. This popular tourist attraction offers stunning views of the Pacific Ocean and is a perfect spot for sunbathing, swimming, and picnicking.

    Photo of Wailea Beach Park - Kihei, HI 96753, USA Photo of Wailea Beach Park - Kihei, HI 96753, USA Photo of Wailea Beach Park - Kihei, HI 96753, USA
    Park Tourist Attraction
    Details
  • #21

    Wailea Ekahi Resort Rentals LLC

    ● Open
    3300 Wailea Alanui Dr #40C, Kihei, HI 96753, United States
    (805) 490-7520
    vrbo.com

    Wailea Ekahi Resort Rentals LLC is a premier lodging institution located at 3300 Wailea Alanui Drive in Kihei, Hawaii, United States.

    Photo of Wailea Ekahi Resort Rentals LLC - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Wailea Ekahi Resort Rentals LLC - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Wailea Ekahi Resort Rentals LLC - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA
    Lodging Business
    Details
  • #22

    Wailea Ekolu 1510 - Two Bedroom Townhouse

    ● Open
    10 Wailea Ekolu Pl APT 1510, Kihei, HI 96753, United States
    (636) 736-4460

    Wailea Ekolu 1510 is a charming two-bedroom townhouse located at 10 Wailea Ekolu Place in Kihei, Hawaii. This cozy lodging option offers a comfortable and spacious setting for guests to relax and unwind during their stay on the beautiful island of Maui.

    Lodging Business
    Details
  • #23

    Wailea Ekolu #102

    ● Open
    10 Wailea Ekolu Pl #102, Kihei, HI 96753, United States
    vacation-maui.net

    Wailea Ekolu #102 is a luxurious lodging option located at 10 Wailea Ekolu Place in Kihei, Hawaii, United States. This bright and airy corner unit offers stunning, unobstructed ocean views of Molokini and Kahoolawe.

    Photo of Wailea Ekolu #102 - 10 Wailea Ekolu Place, Kihei, HI 96753, USA Photo of Wailea Ekolu #102 - 10 Wailea Ekolu Place, Kihei, HI 96753, USA Photo of Wailea Ekolu #102 - 10 Wailea Ekolu Place, Kihei, HI 96753, USA
    Lodging Business
    Details
  • #24

    Views In Wailea

    ● Open
    3300 Wailea Alanui Dr #27d, Kihei, HI 96753, United States
    (808) 276-8315
    viewsinwailea.com

    Views In Wailea is a premier real estate and travel agency located in the beautiful city of Kihei, Hawaii. Situated at 3300 Wailea Alanui Drive, our agency specializes in offering stunning properties with breathtaking views in the Wailea area.

    Photo of Views In Wailea - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Views In Wailea - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA Photo of Views In Wailea - 3300 Wailea Alanui Drive, Kihei, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • #25

    Wailea Vacation Condos

    ● Closed
    3300 Wailea Alanui Dr #28A, Wailea, HI 96753, United States
    (403) 608-2034
    waileavacationcondos.com

    Wailea Vacation Condos is a real estate and travel agency located at 3300 Wailea Alanui Drive in Wailea-Makena, Hawaii, United States.

    Photo of Wailea Vacation Condos - 3300 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Vacation Condos - 3300 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA Photo of Wailea Vacation Condos - 3300 Wailea Alanui Drive, Wailea-Makena, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 5 7
    #26

    Wailea Ekahi 39F

    ● Open
    42 Okolani Dr, Kihei, HI 96753, United States
    (403) 629-6865
    pieceofparadisemaui.com

    Wailea Ekahi 39F is a luxurious vacation rental located at 42 Okolani Drive in Kihei, Hawaii. This stunning property offers breathtaking ocean views and is just steps away from the pristine white sands of Wailea Beach.

    Photo of Wailea Ekahi 39F - 42 Okolani Drive, Kihei, HI 96753, USA Photo of Wailea Ekahi 39F - 42 Okolani Drive, Kihei, HI 96753, USA
    Details
  • 5 1
    #27

    Wailea Vacation Rentals

    ● Closed
    1993 S Kihei Rd STE 208, Kihei, HI 96753, United States
    (808) 879-0038
    wailearentals.com

    Wailea Vacation Rentals is a premier real estate and travel agency located at 1993 South Kihei Road in Kihei, Hawaii.

    Photo of Wailea Vacation Rentals - 1993 South Kihei Road, Kihei, HI 96753, USA Photo of Wailea Vacation Rentals - 1993 South Kihei Road, Kihei, HI 96753, USA Photo of Wailea Vacation Rentals - 1993 South Kihei Road, Kihei, HI 96753, USA
    Real Estate Agent Travel Agency
    Details
  • 5 4
    #28

    Kai Malu at Wailea

    ● Closed
    160 Kai Malu Dr, Kihei, HI 96753, United States
    (808) 875-7783
    kaimaluaoao.com

    Kai Malu at Wailea is a luxurious residential community located at 160 Kai Malu Drive in Kihei, Hawaii. This exclusive institution offers stunning views of the Pacific Ocean and is surrounded by beautiful landscaped gardens.

    Photo of Kai Malu at Wailea - 160 Kai Malu Drive, Kihei, HI 96753, USA Photo of Kai Malu at Wailea - 160 Kai Malu Drive, Kihei, HI 96753, USA Photo of Kai Malu at Wailea - 160 Kai Malu Drive, Kihei, HI 96753, USA
    Details
  • 5 1
    #29

    Wailea Premier Vacation Home Maui

    ● Open
    442 Kupulau Dr, Kihei, HI 96753, United States
    (808) 870-4533

    Wailea Premier Vacation Home Maui is a top-rated real estate and travel agency located at 442 Kupulau Drive in Kihei, Hawaii.

    Photo of Wailea Premier Vacation Home Maui - 442 Kupulau Drive, Kihei, HI 96753, USA Photo of Wailea Premier Vacation Home Maui - 442 Kupulau Drive, Kihei, HI 96753, USA Photo of Wailea Premier Vacation Home Maui - 442 Kupulau Drive, Kihei, HI 96753, USA
    Real Estate Agent Travel Agency
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  • 5 5
    #30

    Aqualani at Grand Wailea

    ● Closed
    Kihei, HI 96753, United States
    (808) 283-0384
    aqualanibeach.com

    Aqualani at Grand Wailea is a premier water sports institution located in Kihei, Hawaii, United States. Offering kayak, stand-up paddle board, and Aqua Glider lessons and rentals, Aqualani is the perfect place to experience the beauty of the ocean.

    Photo of Aqualani at Grand Wailea - Kihei, HI 96753, USA
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  • 1
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