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Results: 897 Rentals

  • Explore Maui! Outdoor Pool, Near Wailea Beach Path, Molokini Crater
    From $545 per night (USD)

    VRBO

    Explore Maui! Outdoor Pool, Near Wailea Beach Path, Molokini Crater

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $545 per night (USD)

    VRBO

    Details
  • 2 x Garden View 2 BR 2 Bath Villa at Palms at Wailea Maui by Outrigger
    From $1212 per night (USD)

    VRBO

    2 x Garden View 2 BR 2 Bath Villa at Palms at Wailea Maui by Outrigger

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $1212 per night (USD)

    VRBO

    Details
  • Great for Groups! 2 Spacious Units, Lanai, Outdoor Pool, Walk to the Beach
    From $1229 per night (USD)

    VRBO

    Great for Groups! 2 Spacious Units, Lanai, Outdoor Pool, Walk to the Beach

    Bedrooms:
    4
    Bathrooms:
    2
    Sleeps:
    8

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $1229 per night (USD)

    VRBO

    Details
  • Garden View 2 Bedroom 2 Bath Villa at Palms at Wailea Maui by Outrigger
    From $593 per night (USD)

    VRBO

    Garden View 2 Bedroom 2 Bath Villa at Palms at Wailea Maui by Outrigger

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $593 per night (USD)

    VRBO

    Details
  • Maui Dream! Full Kitchen,  Pool, Minutes to Keawakapu Beach
    From $485 per night (USD)

    VRBO

    Maui Dream! Full Kitchen, Pool, Minutes to Keawakapu Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $485 per night (USD)

    VRBO

    Details
  • Family Getaway! Pool, Great  Accommodations, Private Lanai
    From $622 per night (USD)

    VRBO

    Family Getaway! Pool, Great Accommodations, Private Lanai

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $622 per night (USD)

    VRBO

    Details
  • Explore Maui! 4 Modern Units, Near Wailea Beach Path, Molokini Crater
    From $2452 per night (USD)

    VRBO

    Explore Maui! 4 Modern Units, Near Wailea Beach Path, Molokini Crater

    Bedrooms:
    8
    Bathrooms:
    4
    Sleeps:
    16

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $2452 per night (USD)

    VRBO

    Details
  • Your Maui Adventure Starts Here! 3 Relaxing Units, Near Grand Wailea Luau
    From $2308 per night (USD)

    VRBO

    Your Maui Adventure Starts Here! 3 Relaxing Units, Near Grand Wailea Luau

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    18

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $2308 per night (USD)

    VRBO

    Details
  • 3 x Ocean View 2BR 2 Bath Villa at Palms at Wailea Maui by Outrigger
    From $1918 per night (USD)

    VRBO

    3 x Ocean View 2BR 2 Bath Villa at Palms at Wailea Maui by Outrigger

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    18

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $1918 per night (USD)

    VRBO

    Details
  • 4 x Garden View Deluxe 1BR 2 Bath Villa at Palms at Wailea Maui by Outrigger
    From $2350 per night (USD)

    VRBO

    4 x Garden View Deluxe 1BR 2 Bath Villa at Palms at Wailea Maui by Outrigger

    Bedrooms:
    8
    Bathrooms:
    4
    Sleeps:
    16

    Perfect for family vacations or couples’ escapes, this condo-style property in Wailea features spacious accommodations w ...

    From $2350 per night (USD)

    VRBO

    Details
  • Maui Designer Beach Villa, Wailea, Ho'olei 39-2
    From $1877 per night (USD)

    VRBO

    Maui Designer Beach Villa, Wailea, Ho'olei 39-2

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Your Pristine Oasis Indulge in the lap of luxury at this exquisite 3,400-square-foot vacation rental villa ( ...

    From $1877 per night (USD)

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    Details
  • Luxury Condo in Wailea with sweeping views
    From $613 per night (USD)

    Expedia

    Luxury Condo in Wailea with sweeping views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    2 large master ensuite bedrooms with Cal King beds. Sweeping views of Kaho'olawe, Molokini, and Lanai islands and spec ...

    From $613 per night (USD)

    Expedia

    Details
  • Palms at Wailea 1405! Great location with ocean views!
    From $647 per night (USD)

    VRBO

    Palms at Wailea 1405! Great location with ocean views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Palms at Wailea 1405 offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush l ...

    From $647 per night (USD)

    VRBO

    Details
  • Polo Beach House - Beachfront Private Estate -  4 bedroom 3 Bath
    From $4830 per night (USD)

    VRBO

    Polo Beach House - Beachfront Private Estate - 4 bedroom 3 Bath

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    This is unique property has singular direct beach access to Polo Beach. Walk out of your oceanfront yard over a short ...

    From $4830 per night (USD)

    VRBO

    Details
  • Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B\n
    From $983 per night (USD)

    VRBO

    Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B\n

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    7

    Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program. Wailea Ekahi Village #30B, is a ...

    From $983 per night (USD)

    VRBO

    Details
  • Palms at Wailea 2206, offers the perfect location in Wailea!
    From $705 per night (USD)

    Expedia

    Palms at Wailea 2206, offers the perfect location in Wailea!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Palms at Wailea 2206, offers the perfect location in Wailea. This 2-bedroom/2-bath unit surrounded by the lush landscapi ...

    From $705 per night (USD)

    Expedia

    Details
  • WE 504 Remodeled 2BD Wailea Condo w AC Pool Panoramic Ocean Views Near Beach
    From $807 per night (USD)

    VRBO

    WE 504 Remodeled 2BD Wailea Condo w AC Pool Panoramic Ocean Views Near Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, ...

    From $807 per night (USD)

    VRBO

    Details
  • Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!
    From $721 per night (USD)

    Expedia

    Ground-Floor Retreat Wailea Ekahi Condo #33B: Updated & Perfect for Your Escape!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program. If you have a stay that qualifie ...

    From $721 per night (USD)

    Expedia

    Details
  • PICTURESQUE OCEAN VIEW CONDO - LAST MINUTE DEAL!CHRISTMAS AVAILABLE AT ELUA 2002
    From $1271 per night (USD)

    VRBO

    PICTURESQUE OCEAN VIEW CONDO - LAST MINUTE DEAL!CHRISTMAS AVAILABLE AT ELUA 2002

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Elua #2002 Ocean View Condo This newly remodeled in 2021 second floor 2 bedroom and 2 bathroom condo has an open ...

    From $1271 per night (USD)

    VRBO

    Details
  • I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY
    From $2035 per night (USD)

    Expedia

    I.P.M PRESENTS: VILLA E301 - STUNNING NEW REMODEL + FLEXIBLE CANCELATION POLICY

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    SECURE YOUR RESERVATION WITHIN MINUTES! SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS! 24 HOUR PROFESSIONAL PROPER ...

    From $2035 per night (USD)

    Expedia

    Details
  • I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!
    From $2227 per night (USD)

    VRBO

    I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    SECURE YOUR RESERVATION WITHIN MINUTES SAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS 24 HOUR PROFESSIONAL PROPERTY ...

    From $2227 per night (USD)

    VRBO

    Details
  • Palms at Wailea 601, perfect location in Wailea!
    From $638 per night (USD)

    Expedia

    Palms at Wailea 601, perfect location in Wailea!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Palms at Wailea 601 offers the perfect location in Wailea. This 2-bedroom/2-bath ground level unit surrounded by the lus ...

    From $638 per night (USD)

    Expedia

    Details
  • Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!
    From $584 per night (USD)

    VRBO

    Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekolu 102 is a bright and airy corner unit showcases spectacular, unobstructed forever ocean views that take in t ...

    From $584 per night (USD)

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    Details
  • Spectacular Ocean Views! Luxury abounds at Ho'olei Villas! 17-1
    From $2515 per night (USD)

    Expedia

    Spectacular Ocean Views! Luxury abounds at Ho'olei Villas! 17-1

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    This property is hotel zoned, and not being affected by the recent proposed legislation. Luxury at its finest! Ho'olei ...

    From $2515 per night (USD)

    Expedia

    Details
  • Wailea Ekolu #604 Ocean View! Walking Distance to Ulua Beach, Wifi, Full A\/C
    From $648 per night (USD)

    VRBO

    Wailea Ekolu #604 Ocean View! Walking Distance to Ulua Beach, Wifi, Full A\/C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Aloha! Wailea Ekolu #604, a 2-bedroom, 2-bathroom, second floor unit which features a fully equipped kitchen, high-speed ...

    From $648 per night (USD)

    VRBO

    Details
  • Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel!  AC and Pool.
    From $635 per night (USD)

    Expedia

    Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    If you are looking for a modern, luxurious retreat for families in Wailea with BRAND NEW EVERYTHING, look no further! ...

    From $635 per night (USD)

    Expedia

    Details
  • Remaining 2024 $350\/nt Fabulous Condo with Amazing Ocean Views - Building 22!
    From $1115 per night (USD)

    VRBO

    Remaining 2024 $350\/nt Fabulous Condo with Amazing Ocean Views - Building 22!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny side' of Maui! T ...

    From $1115 per night (USD)

    VRBO

    Details
  • Maui Ohana partial ocean view with epic sunset views from lanai - close to beach
    From $532 per night (USD)

    Expedia

    Maui Ohana partial ocean view with epic sunset views from lanai - close to beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Grand Champions 58 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...

    From $532 per night (USD)

    Expedia

    Details
  • Wailea Point heavenly sunsets in paradise. Minimum 30 days
    From $1205 per night (USD)

    VRBO

    Wailea Point heavenly sunsets in paradise. Minimum 30 days

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2 bedrooms, 2 full bathrooms recently renovated property with breathtaking ocean views. Sit and sip on the lanai or on t ...

    From $1205 per night (USD)

    VRBO

    Details
  • Wailea Ekolu #1508 Best Location, Panoramic Ocean View, Renovated, Full A\/C
    From $842 per night (USD)

    Expedia

    Wailea Ekolu #1508 Best Location, Panoramic Ocean View, Renovated, Full A\/C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Experience the comforts of home in a newly renovated, spacious, ocean-view condo. Greet each day from your relaxing priv ...

    From $842 per night (USD)

    Expedia

    Details
  • Mesmerizing Vistas - Oceanfront Treasure: Wailea Elua 1404  - Lush Surroundings
    From $1408 per night (USD)

    VRBO

    Mesmerizing Vistas - Oceanfront Treasure: Wailea Elua 1404 - Lush Surroundings

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Highly cleaned and sanitized for your vacation. Ask about our AlohaSafeStay program. If you have a stay that qualifie ...

    From $1408 per night (USD)

    VRBO

    Details
  • Grand Champions Villas 61  Beautiful Remodel in Wailea
    From $530 per night (USD)

    Expedia

    Grand Champions Villas 61 Beautiful Remodel in Wailea

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Nestled in the prestigious Wailea Resort community, Grand Champions Villas 61 offers a prime retreat with breathtaking v ...

    From $530 per night (USD)

    Expedia

    Details
  • Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A\/C
    From $646 per night (USD)

    VRBO

    Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A\/C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy spectacular panoramic ocean views from this 2 bedroom condo in a truly private setting! Location is everything and ...

    From $646 per night (USD)

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    Details
  • Polo Beach 808! Gorgeous View 1 bedroom!
    From $1153 per night (USD)

    Expedia

    Polo Beach 808! Gorgeous View 1 bedroom!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    This is an amazing condo with beautiful views. Everything was pictured, so well stocked and extremely clean. We loved ev ...

    From $1153 per night (USD)

    Expedia

    Details
  • Newly Renovated High-end 1 bedroom, 2 bathroom Wailea Condo close to beach
    From $658 per night (USD)

    VRBO

    Newly Renovated High-end 1 bedroom, 2 bathroom Wailea Condo close to beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    The Palms at Wailea #1804 has been completely renovated, be among the first to enjoy this brand-new high-end renovation ...

    From $658 per night (USD)

    VRBO

    Details
  • Palms at Wailea 705 - Beautifully renovated ground floor unit in premium location, Split AC
    From $533 per night (USD)

    Expedia

    Palms at Wailea 705 - Beautifully renovated ground floor unit in premium location, Split AC

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Palms at Wailea 705, a 2 bedroom, 2 bath ground level unit, is your perfect Wailea location. Featuring Mediterranean ...

    From $533 per night (USD)

    Expedia

    Details
  • 1BEDROOM\/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned
    From $501 per night (USD)

    VRBO

    1BEDROOM\/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Retreat and relax in this comfortable, serene, light and airy, completely remodeled unit. This ground floor unit in t ...

    From $501 per night (USD)

    VRBO

    Details
  • Palms at Wailea 1201! Perfect location in Wailea!
    From $660 per night (USD)

    Expedia

    Palms at Wailea 1201! Perfect location in Wailea!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Palms at Wailea 1201! Perfect location in Wailea! This 2-bed/2-bath condo offers the perfect getaway for families or cou ...

    From $660 per night (USD)

    Expedia

    Details
  • Palms at Wailea 1203, offers the perfect location in Wailea!
    From $655 per night (USD)

    VRBO

    Palms at Wailea 1203, offers the perfect location in Wailea!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush ...

    From $655 per night (USD)

    VRBO

    Details
  • Ho'olei Villas | Wailea Kapili
    From $2169 per night (USD)

    Expedia

    Ho'olei Villas | Wailea Kapili

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    This residence has been given the Hawaiian name "Wailea Kapili", which translates to "a Wailea Gathering." It is the per ...

    From $2169 per night (USD)

    Expedia

    Details
  • Fully Remodeled Modern Island Style!
    From $695 per night (USD)

    VRBO

    Fully Remodeled Modern Island Style!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Aloha and welcome to our condo, the Palms at Wailea 606. We’re looking forward to hosting you and making your vacation ...

    From $695 per night (USD)

    VRBO

    Details
  • Palms at Wailea #1207 Ground Floor Unit, Near Complex Pool and Shared Hot Tub
    From $549 per night (USD)

    Expedia

    Palms at Wailea #1207 Ground Floor Unit, Near Complex Pool and Shared Hot Tub

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Palms at Wailea #1207 is a lovely ground-floor unit at a much sought-after complex. It is a spacious 2 bedroom, 2 bath u ...

    From $549 per night (USD)

    Expedia

    Details
  • NEWLY REMODELED! Partial Ocean View condo along the golf course
    From $695 per night (USD)

    VRBO

    NEWLY REMODELED! Partial Ocean View condo along the golf course

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This newly remodeled 3 bedroom 2 bath condo located in the heart of Wailea is the perfect vacation oasis for your island ...

    From $695 per night (USD)

    VRBO

    Details
  • Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC
    From $467 per night (USD)

    Expedia

    Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Wailea Ekolu 407, experience breathtaking, panoramic ocean views from main living area and over-sized lanai o ...

    From $467 per night (USD)

    Expedia

    Details
  • Oceanview condo with private lanai, pool, tennis court & shared washer\/dryer
    From $721 per night (USD)

    VRBO

    Oceanview condo with private lanai, pool, tennis court & shared washer\/dryer

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi Villages Unit 44D Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...

    From $721 per night (USD)

    VRBO

    Details
  • BEAUTIFULLY UPGRADED! OCEAN and FAIRWAY VIEWS! GC 166!
    From $677 per night (USD)

    Expedia

    BEAUTIFULLY UPGRADED! OCEAN and FAIRWAY VIEWS! GC 166!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Luxury awaits you in this beautifully upgraded 2-bedroom condo. Magnificent ocean and fairway views from this beachy uni ...

    From $677 per night (USD)

    Expedia

    Details
  • KBM Resorts: Grand Champions GCH-120, Remodeled Bdm Villa in Heart of Wailea, Includes Rental Car!
    From $1968 per night (USD)

    VRBO

    KBM Resorts: Grand Champions GCH-120, Remodeled Bdm Villa in Heart of Wailea, Includes Rental Car!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Step into this 2 Bedroom, 2 Bathroom villa and immediately fall in love with the renovated space and captivating ocean a ...

    From $1968 per night (USD)

    VRBO

    Details
  • Panoramic Ocean View Condo on Golf Course close to Beaches
    From $761 per night (USD)

    Expedia

    Panoramic Ocean View Condo on Golf Course close to Beaches

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Our townhouse in the Wailea Ekolu Place located on the Wailea Blue Golf Course. It has a spectacular view and large lana ...

    From $761 per night (USD)

    Expedia

    Details
  • WEK 37C Winter Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
    From $462 per night (USD)

    VRBO

    WEK 37C Winter Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, ...

    From $462 per night (USD)

    VRBO

    Details
  • NEW!! Wailea Ekolu Ocean Suite 207 with AC and Ocean Views
    From $701 per night (USD)

    Expedia

    NEW!! Wailea Ekolu Ocean Suite 207 with AC and Ocean Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    NEW LISTING!!! PRICE REDUCED!!! Wailea Ekolu #207 is a luxurious accommodation located in the heart of Wailea, offering ...

    From $701 per night (USD)

    Expedia

    Details
  • Enchanting Modern Wailea Vistas
    From $956 per night (USD)

    VRBO

    Enchanting Modern Wailea Vistas

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Summary: Perched overlooking Wailea on southern Maui, this immaculate one-bedroom condo is a dreamy escape into open air ...

    From $956 per night (USD)

    VRBO

    Details
  • Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-Fi
    From $1139 per night (USD)

    Expedia

    Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua 1201 is perfectly positioned in the coveted interior courtyard, 39 steps to famous Ulua Beach, perennially n ...

    From $1139 per night (USD)

    Expedia

    Details
  • Top Floor, Favorite Location, Ocean Views! Palms at Wailea 2104
    From $516 per night (USD)

    VRBO

    Top Floor, Favorite Location, Ocean Views! Palms at Wailea 2104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    #2104 is a spacious and recently refreshed 2-bedroom, 2-bathroom condo in Maui with fun tropical accents and cozy comfor ...

    From $516 per night (USD)

    VRBO

    Details
  • New Listing! 40D- Gorgeous and Bright Remodel! Tranquil Tropical Views!
    From $736 per night (USD)

    Expedia

    New Listing! 40D- Gorgeous and Bright Remodel! Tranquil Tropical Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located just moments away from the pristine beaches, this elegant condo offers the perfect balance of tranquility and co ...

    From $736 per night (USD)

    Expedia

    Details
  • Wailea Surf Shack: Golf, shopping & beaches!
    From $608 per night (USD)

    VRBO

    Wailea Surf Shack: Golf, shopping & beaches!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Surf Shack! New renovation in April 2023. Feel secure booking with us as we truly treat our guests lik ...

    From $608 per night (USD)

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  • Grand Island Paradise on Golf Course w\/Ocean Views
    From $1148 per night (USD)

    Expedia

    Grand Island Paradise on Golf Course w\/Ocean Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    🌅 Relax and enjoy sunset ocean views every night! 🏖️We are <1 mile from Wailea Beach! Our home is spacious, in a perf ...

    From $1148 per night (USD)

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    Details
  • Gorgeous REMODEL! Two King Suites & Huge Ocean Views! Close To Wailea Beaches
    From $1019 per night (USD)

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    Gorgeous REMODEL! Two King Suites & Huge Ocean Views! Close To Wailea Beaches

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come experience this recently renovated gem located in the highly desired Wailea Ekolu. Expansive panoramic ocean views, ...

    From $1019 per night (USD)

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  • New! Luxurious 3bd Villa at Wailea Beach Villas unit E201
    From $2156 per night (USD)

    Expedia

    New! Luxurious 3bd Villa at Wailea Beach Villas unit E201

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Wailea Beach Villas is simply the best of the best! Voted #3 Resort in Hawaii by Conde Nast Reader’s Choice Awards 2019. ...

    From $2156 per night (USD)

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  • Palms at Wailea #1005 Panoramic Ocean Views, Ground Floor, Wifi, Near Beaches
    From $531 per night (USD)

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    Palms at Wailea #1005 Panoramic Ocean Views, Ground Floor, Wifi, Near Beaches

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Palms at Wailea #1005 is a ground floor ocean view 1 bedroom 2 bath unit with a full kitchen, washer and dryer, room AC ...

    From $531 per night (USD)

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  • Wailea Ekolu #306 Panoramic Ocean Views on Wailea Golf Course, Wifi, A\/C
    From $607 per night (USD)

    Expedia

    Wailea Ekolu #306 Panoramic Ocean Views on Wailea Golf Course, Wifi, A\/C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy spectacular panoramic ocean views from this beautiful condo in a truly private setting! This is one of the best lo ...

    From $607 per night (USD)

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  • Wailea Elua 2110 Panoramic Ocean View, Second Floor, Central Air Throughout
    From $894 per night (USD)

    VRBO

    Wailea Elua 2110 Panoramic Ocean View, Second Floor, Central Air Throughout

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    If you are looking for a luxury ocean front property in Wailea, look no further! Wailea Elua #2110 is a beautifully remo ...

    From $894 per night (USD)

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  • Beachfront Village in Wailea, easy walk, or drive, to shops and dining
    From $756 per night (USD)

    Expedia

    Beachfront Village in Wailea, easy walk, or drive, to shops and dining

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Escape to a haven where the sun caresses the horizon, where the breeze whispers through the palms, and where every momen ...

    From $756 per night (USD)

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  • KBM Resorts: Grand Champions GCH-42, Remodeled 2 Bd Villa in Heart of Wailea, Includes Rental Car!
    From $1379 per night (USD)

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    KBM Resorts: Grand Champions GCH-42, Remodeled 2 Bd Villa in Heart of Wailea, Includes Rental Car!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Step into this 2 Bedroom, 2 Bathroom villa and immediately fall in love with the renovated space and captivating ocean a ...

    From $1379 per night (USD)

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  • New Listing! Polo 106-Closest to Beach! Amazing Views! Favorite Location!
    From $1362 per night (USD)

    Expedia

    New Listing! Polo 106-Closest to Beach! Amazing Views! Favorite Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your own private oasis! This stunning oceanfront condo is just steps away from the beach, offering breathtaki ...

    From $1362 per night (USD)

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  • Ekahi 49E Sweeping Ocean Views
    From $773 per night (USD)

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    Ekahi 49E Sweeping Ocean Views

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    WAILEA EKAHI 49E – OCEAN & HALEAKALA VIEWS Best views at Ekahi Village! Watch the sunrise over Haleakala from the kitch ...

    From $773 per night (USD)

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  • Ekahi 48B Garden View Studio
    From $358 per night (USD)

    Expedia

    Ekahi 48B Garden View Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Our beautifully remodeled ground floor Ekahi studio condo provides a relaxing and peaceful setting with beautiful garden ...

    From $358 per night (USD)

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    Details
  • Ekahi 49D, Big Ocean Views, 2nd floor
    From $722 per night (USD)

    VRBO

    Ekahi 49D, Big Ocean Views, 2nd floor

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Our beautifully maintained, uniquely remodeled 1 bedroom, 1.5 bath Ekahi Condo offers sweeping ocean views across the gr ...

    From $722 per night (USD)

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  • Wailea Grand Champions | 88
    From $520 per night (USD)

    Expedia

    Wailea Grand Champions | 88

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Wailea Grand Champions 88 offers breathtaking views that will never cease to amaze. Enjoy your morning coffee on the lan ...

    From $520 per night (USD)

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    Details
  • Wailea Ekolu Village | 1107
    From $432 per night (USD)

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    Wailea Ekolu Village | 1107

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning v ...

    From $432 per night (USD)

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  • Wailea Ekahi Village | 54D
    From $534 per night (USD)

    Expedia

    Wailea Ekahi Village | 54D

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 54D is a stunning second-floor vacation rental offering breathtaking views of the ocean and West Maui mount ...

    From $534 per night (USD)

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    Details
  • Wailea Ekahi Village | 50C
    From $456 per night (USD)

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    Wailea Ekahi Village | 50C

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Experience the ultimate in island luxury with a stay at Wailea Ekahi 50C, a beautiful one-bedroom, one-bathroom vacation ...

    From $456 per night (USD)

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  • Wailea Ekahi Village | 49C
    From $524 per night (USD)

    Expedia

    Wailea Ekahi Village | 49C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi Village 49C is a charming vacation rental located in one of the most popular Wailea vacation rental communi ...

    From $524 per night (USD)

    Expedia

    Details
  • Wailea Ekolu Village | 403
    From $377 per night (USD)

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    Wailea Ekolu Village | 403

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Ekolu Village 403 is a charming two-bedroom, two-bathroom vacation rental that offers breathtaking ocean views. T ...

    From $377 per night (USD)

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  • Wailea Ekolu Village | 1205
    From $515 per night (USD)

    Expedia

    Wailea Ekolu Village | 1205

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekolu 1205 is a two-bedroom, two-bathroom ocean view vacation residence that comfortably accommodates four people ...

    From $515 per night (USD)

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    Details
  • Wailea Grand Champions | 43
    From $516 per night (USD)

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    Wailea Grand Champions | 43

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with ...

    From $516 per night (USD)

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  • Wailea Ekahi Village | 49B
    From $513 per night (USD)

    Expedia

    Wailea Ekahi Village | 49B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 49B is a stunning ocean view condominium located in the heart of the renowned Wailea resort area. Nestled a ...

    From $513 per night (USD)

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    Details
  • Wailea Ekolu Village | 706
    From $432 per night (USD)

    VRBO

    Wailea Ekolu Village | 706

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Towering oleander and bougainvillea grace the front entry of Wailea Ekolu 706. Enjoy views out over the tropical ground ...

    From $432 per night (USD)

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  • Wailea Ekolu Village | 1607
    From $342 per night (USD)

    Expedia

    Wailea Ekolu Village | 1607

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful ...

    From $342 per night (USD)

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    Details
  • Wailea Ekolu Village | 1703
    From $332 per night (USD)

    VRBO

    Wailea Ekolu Village | 1703

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekolu 1703 is a stunning one-bedroom, two-bath ocean view vacation rental on the beautiful island of Maui that co ...

    From $332 per night (USD)

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  • Wailea Ekahi Village | 7B
    From $465 per night (USD)

    Expedia

    Wailea Ekahi Village | 7B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Ekahi 7B is a beautifully appointed vacation rental located within the serene Wailea Ekahi Village. This spacious ...

    From $465 per night (USD)

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    Details
  • Wailea Elua Village | 706
    From $1275 per night (USD)

    VRBO

    Wailea Elua Village | 706

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to your dream vacation retreat in Wailea! As you step inside Wailea Elua 706, you'll immediately be captivated b ...

    From $1275 per night (USD)

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  • Wailea Elua Village | 910
    From $704 per night (USD)

    Expedia

    Wailea Elua Village | 910

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea communit ...

    From $704 per night (USD)

    Expedia

    Details
  • Wailea Ekahi Village | 9A
    From $446 per night (USD)

    VRBO

    Wailea Ekahi Village | 9A

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Wailea Ekahi 9A, a charming vacation rental nestled in the heart of Wailea. This meticulously maintained one- ...

    From $446 per night (USD)

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  • Wailea Elua Village | 1001
    From $2036 per night (USD)

    Expedia

    Wailea Elua Village | 1001

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. F ...

    From $2036 per night (USD)

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    Details
  • Wailea Ekahi Village | 15E
    From $417 per night (USD)

    VRBO

    Wailea Ekahi Village | 15E

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Escape to Wailea Ekahi 15E, a comfortable 600 square foot vacation rental in the luxurious Wailea community. This vacati ...

    From $417 per night (USD)

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  • Wailea Ekahi Village | 4D
    From $388 per night (USD)

    Expedia

    Wailea Ekahi Village | 4D

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit off ...

    From $388 per night (USD)

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    Details
  • Wailea Elua Village | 1511
    From $716 per night (USD)

    VRBO

    Wailea Elua Village | 1511

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 1511 is a premier vacation rental nestled in the heart of Wailea, offering a perfect blend of luxury ...

    From $716 per night (USD)

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  • Wailea Elua Village | 804
    From $1409 per night (USD)

    Expedia

    Wailea Elua Village | 804

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island o ...

    From $1409 per night (USD)

    Expedia

    Details
  • Wailea Elua Village | 1203
    From $878 per night (USD)

    VRBO

    Wailea Elua Village | 1203

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the p ...

    From $878 per night (USD)

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  • Wailea Ekahi Village | 12B
    From $414 per night (USD)

    Expedia

    Wailea Ekahi Village | 12B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designe ...

    From $414 per night (USD)

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    Details
  • Wailea Ekahi Village | 11C
    From $560 per night (USD)

    VRBO

    Wailea Ekahi Village | 11C

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in t ...

    From $560 per night (USD)

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    Details
  • Wailea Elua Village | 2402
    From $691 per night (USD)

    Expedia

    Wailea Elua Village | 2402

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 2402 is an exquisite ocean-view second-floor condo located in the prestigious Wailea area of Maui. T ...

    From $691 per night (USD)

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    Details
  • Wailea Elua Village | 705
    From $1015 per night (USD)

    VRBO

    Wailea Elua Village | 705

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This two-bedroom, two-bathroom c ...

    From $1015 per night (USD)

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    Details
  • Wailea Ekahi Village | 15D
    From $456 per night (USD)

    Expedia

    Wailea Ekahi Village | 15D

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Wailea Ekahi 15D, a stunning one-bedroom, one-bathroom vacation rental nestled in the heart of Wailea. This s ...

    From $456 per night (USD)

    Expedia

    Details
  • Wailea Elua Village | 1802
    From $583 per night (USD)

    VRBO

    Wailea Elua Village | 1802

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua Village 1802 is situated along the southern-most border of the resort, offering more privacy, as well as uni ...

    From $583 per night (USD)

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    Details
  • Wailea Elua Village | 1202
    From $808 per night (USD)

    Expedia

    Wailea Elua Village | 1202

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua 1202 is a stunning vacation rental property that offers visitors a truly luxurious and unforgettable experie ...

    From $808 per night (USD)

    Expedia

    Details
  • Wailea Elua Village | 2005
    From $1044 per night (USD)

    VRBO

    Wailea Elua Village | 2005

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Elua Village 2005 is a stunning two-bedroom, two-bathroom vacation rental located in the desirable Wailea region ...

    From $1044 per night (USD)

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  • Wailea Elua Village | 1510
    From $1151 per night (USD)

    Expedia

    Wailea Elua Village | 1510

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Elua 1510 is a charming two-bedroom, two-bathroom vacation rental located in the premier Maui vacation destinatio ...

    From $1151 per night (USD)

    Expedia

    Details
  • Wailea Ekahi Village | 3B
    From $417 per night (USD)

    VRBO

    Wailea Ekahi Village | 3B

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Nestled among the lush, tropical landscape, this studio is a perfect place to escape the hustle and bustle. Bring along ...

    From $417 per night (USD)

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    Details
  • Wailea Elua Village | 208
    From $945 per night (USD)

    Expedia

    Wailea Elua Village | 208

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Wailea Elua 208, where paradise meets luxury! This stunning one-bedroom ocean view vacation rental is the per ...

    From $945 per night (USD)

    Expedia

    Details