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Results: 913 Rentals

  • Ekahi 27A: Priceless Ocean View from a Private Lanai
    From $770 per night (USD)

    VRBO

    Ekahi 27A: Priceless Ocean View from a Private Lanai

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Private corner unit, 1 bedroom 1 bathroom with 2 private lanais. Ocean view. Have all your meals in our large private l ...

    From $770 per night (USD)

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    Details
  • #21B Grand Champions Studio -Ulua & Mokapu beaches
    From $209 per night (USD)

    Expedia

    #21B Grand Champions Studio -Ulua & Mokapu beaches

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in the heart of Wailea. Grand Champions is a 4 star-world-class resort that features two pools with whirlpool sp ...

    From $209 per night (USD)

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  • #21A Grand Champions 1 Bed - Ulua & Mokapu beaches
    From $269 per night (USD)

    VRBO

    #21A Grand Champions 1 Bed - Ulua & Mokapu beaches

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Welcome to our spacious ground floor condo with a tropical garden view. Located in the heart of Wailea. Grand Champions ...

    From $269 per night (USD)

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  • Grand Champions #135, Shared Hot Tub, First Floor, Full A/C, Great Rates
    From $291 per night (USD)

    Expedia

    Grand Champions #135, Shared Hot Tub, First Floor, Full A/C, Great Rates

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Grand Champions #135 is a 1 bedroom 2 bath unit in a lovely complex - brand new to the rental market with a fanta ...

    From $291 per night (USD)

    Expedia

    Details
  • Exquisite Oceanfront Wailea Beach Villas B202
    From $3491 per night (USD)

    VRBO

    Exquisite Oceanfront Wailea Beach Villas B202

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This property is hotel zoned, and not being affected by the recent proposed legislation. Be one of the first guests to ...

    From $3491 per night (USD)

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    Details
  • Wailea Ekolu Village | 1203
    From $801 per night (USD)

    Expedia

    Wailea Ekolu Village | 1203

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Wailea Ekolu Village condo #1203 is an exquisite one-bedroom, two-bathroom ocean view retreat designed for discerning tr ...

    From $801 per night (USD)

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    Details
  • Wailea Point | 2301 | 30+ Night Luxury Stays
    From $1065 per night (USD)

    VRBO

    Wailea Point | 2301 | 30+ Night Luxury Stays

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, ...

    From $1065 per night (USD)

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  • Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guests
    From $298 per night (USD)

    Expedia

    Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guests

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    *New Furniture throughout!! This two-bedroom, two-bath garden-view condo has just been remodeled with all new furniture ...

    From $298 per night (USD)

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    Details
  • Wailea Ekahi Village | 52D
    From $899 per night (USD)

    VRBO

    Wailea Ekahi Village | 52D

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on t ...

    From $899 per night (USD)

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    Details
  • Grand Champions #57 Gorgeous High-end Wailea Suite on Ground Floor, Full A/C
    From $458 per night (USD)

    Expedia

    Grand Champions #57 Gorgeous High-end Wailea Suite on Ground Floor, Full A/C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Grand Champions #57 is a spacious, bright and airy 1Bd/2Ba unit on the ground floor. It features window unit air conditi ...

    From $458 per night (USD)

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    Details
  • Exquisite Top-Floor Condo with Ocean Views and a Huge Private Lanai
    From $432 per night (USD)

    VRBO

    Exquisite Top-Floor Condo with Ocean Views and a Huge Private Lanai

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Grand Champions #40 is an exquisite top floor, Oceanview option for your Maui getaway. Huge, private lanai offers dining ...

    From $432 per night (USD)

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    Details
  • Updated Private Home with Serene Fairway Views Modern Comfort in Paradise!
    From $463 per night (USD)

    Expedia

    Updated Private Home with Serene Fairway Views Modern Comfort in Paradise!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Newly updated home with privacy and serenity. Tucked amongst the tropical foliage, in the far corner of the property, ov ...

    From $463 per night (USD)

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    Details
  • Ocean Views | Polo Beach Club Ground Floor Condo | Walk to Beach, Private Patio
    From $1171 per night (USD)

    Expedia

    Ocean Views | Polo Beach Club Ground Floor Condo | Walk to Beach, Private Patio

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Escape to paradise at this ground-floor condo at the exclusive Polo Beach Club. Enjoy stunning ocean views, lus ...

    From $1171 per night (USD)

    Expedia

    Details
  • Outstanding Wailea 3 bed/2 ba Grand Champion #94 - big lanai and ocean views
    From $676 per night (USD)

    Expedia

    Outstanding Wailea 3 bed/2 ba Grand Champion #94 - big lanai and ocean views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Bldg. 10 - Unit #94 - New, New New. New roof, new carpet, new appliances, new bed - renewed throughout, an impeccable 3 ...

    From $676 per night (USD)

    Expedia

    Details
  • Wailea Grand Champion #90 Breathtaking Partial Ocean & Fairway Views
    From $363 per night (USD)

    VRBO

    Wailea Grand Champion #90 Breathtaking Partial Ocean & Fairway Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Wailea Grand Champions #90 – Partial Ocean & Fairway Views in the Heart of Wailea Escape to the peaceful beauty of Wail ...

    From $363 per night (USD)

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  • Wailea Maui Oasis at The Grand Champions
    From $301 per night (USD)

    Expedia

    Wailea Maui Oasis at The Grand Champions

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Forget your worries in the spacious and serene space. This recently refreshed bright, 1 bedroom, 2 bath condo is perfect ...

    From $301 per night (USD)

    Expedia

    Details
  • Wailea Ekolu Village 1406 | Gorgeous Views + Community Pool!
    From $400 per night (USD)

    VRBO

    Wailea Ekolu Village 1406 | Gorgeous Views + Community Pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Wailea Ekolu Village 1406, your serene tropical oasis nestled in the heart of Kihei, Hawaii. This stunning co ...

    From $400 per night (USD)

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    Details
  • PAW 1706 Remodeled Wailea Condo w Pool AC Near Beach
    From $391 per night (USD)

    Expedia

    PAW 1706 Remodeled Wailea Condo w Pool AC Near Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

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

    From $391 per night (USD)

    Expedia

    Details
  • Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split AC
    From $440 per night (USD)

    VRBO

    Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split AC

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Wailea Ekahi 39E, a beautifully appointed one-bedroom, two-bath condo offering breathtaking ocean views and t ...

    From $440 per night (USD)

    VRBO

    Details
  • Oceanfront Paradise Awaits at Wailea Ekahi 37E
    From $450 per night (USD)

    Expedia

    Oceanfront Paradise Awaits at Wailea Ekahi 37E

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    5

    Wailea Ekahi 37E Limited-Time Offer – Direct Bookings Only • Stay 5 Nights, Get the 6th Night Free Book a stay for Aug ...

    From $450 per night (USD)

    Expedia

    Details
  • Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views
    From $656 per night (USD)

    VRBO

    Sandy Beach Front Property - Family Friendly - 4 min stroll to H2O - Ocean Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to paradise to our family friendly beach front property, Wailea Ekahi Villas unit 35B. 35B is a luxurious 2-bed ...

    From $656 per night (USD)

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    Details
  • Grand Champion Villa Getaway - Wailea Beaches
    From $648 per night (USD)

    Expedia

    Grand Champion Villa Getaway - Wailea Beaches

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Pet-Friendly – Bring your furry friend! (make sure you disclose it prior to check-in) This luxurious 300 sq. ft. vacatio ...

    From $648 per night (USD)

    Expedia

    Details
  • Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!
    From $424 per night (USD)

    VRBO

    Receive a $100 Gift Card for Snorkel Gear or Wailea Dining Options!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    For bookings with arrivals on January 5th, 2025- Nov 20th 2025, enjoy an exclusive offer! Book 6 nights or more can choo ...

    From $424 per night (USD)

    VRBO

    Details
  • Wailea Elua Village | 1509
    From $741 per night (USD)

    Expedia

    Wailea Elua Village | 1509

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village offers tropical vacation condos set amid Wailea’s resort hotels, making it a perfect luxury destinat ...

    From $741 per night (USD)

    Expedia

    Details
  • Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout
    From $345 per night (USD)

    VRBO

    Grand Champions #50, Great Location Near Pool and Hot Tub, AC Throughout

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Grand Champions #50 is a 2 bedroom, 2 bath, 2nd floor unit (no elevator) with a garden view at the Grand Champion ...

    From $345 per night (USD)

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    Details
  • Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!
    From $296 per night (USD)

    Expedia

    Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Escape to paradise in this luxurious 1-bedroom, 2-bath condo located in the heart of Wailea, Maui. Enjoy breathtaking oc ...

    From $296 per night (USD)

    Expedia

    Details
  • Wailea Hoolei 93-3 Rarely Priced for Last Minute May Getaway at Luxurious Condo
    From $1322 per night (USD)

    VRBO

    Wailea Hoolei 93-3 Rarely Priced for Last Minute May Getaway at Luxurious Condo

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforge ...

    From $1322 per night (USD)

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  • NEWLY REMODELED-QUIET LOCATION-AC-WELL EQUIPPED-METICULOUS CLEANING
    From $671 per night (USD)

    Expedia

    NEWLY REMODELED-QUIET LOCATION-AC-WELL EQUIPPED-METICULOUS CLEANING

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all ne ...

    From $671 per night (USD)

    Expedia

    Details
  • Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
    From $1227 per night (USD)

    VRBO

    Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Brand New Vacation Rental Managed By Waiola Realty! Welcome to Ho'olei 21-6. Though we don't have any reviews yet, ple ...

    From $1227 per night (USD)

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    Details
  • Top Floor Ocean-View | Walk to Beach | Stylish Wailea Vacation Rental
    From $457 per night (USD)

    Expedia

    Top Floor Ocean-View | Walk to Beach | Stylish Wailea Vacation Rental

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Top Floor Ocean-View | Walk to Beach | Stylish Wailea Vacation Rental Experience the perfect Maui getaway at Palms at W ...

    From $457 per night (USD)

    Expedia

    Details
  • Wailea Elua condo - Ocean Views | Gym | Pickleball
    From $1240 per night (USD)

    VRBO

    Wailea Elua condo - Ocean Views | Gym | Pickleball

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Welcome to your slice of Hawaiian paradise at Wailea Elua! Here, modern luxury meets breathtaking ocean vistas, ...

    From $1240 per night (USD)

    VRBO

    Details
  • Wailea Getaway - 2BD - steps to great pool & beach
    From $719 per night (USD)

    Expedia

    Wailea Getaway - 2BD - steps to great pool & beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa ...

    From $719 per night (USD)

    Expedia

    Details
  • Palms at Wailea Villa 1210 Garden.
    From $452 per night (USD)

    VRBO

    Palms at Wailea Villa 1210 Garden.

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    - Fully renovated 1st floor walk-up unit - Renovated Kitchen includes stovetop, oven, microwave, refrigerator, dishw ...

    From $452 per night (USD)

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    Details
  • Impressive Wailea Point 2 Bedroom+Loft/2 Bath Oceanview Condominium
    Click For Pricing

    Expedia

    Impressive Wailea Point 2 Bedroom+Loft/2 Bath Oceanview Condominium

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Yes, you can rent a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wa ...

    Click For Pricing

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  • Wailea 2BR | Walk to Beach | A/C | Family-Friendly
    From $417 per night (USD)

    VRBO

    Wailea 2BR | Walk to Beach | A/C | Family-Friendly

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Make lasting memories in this peaceful Wailea retreat—perfect for families and island adventurers alike. Start ...

    From $417 per night (USD)

    VRBO

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  • Wailea Beach Villas PH106
    From $1423 per night (USD)

    Expedia

    Wailea Beach Villas PH106

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfr ...

    From $1423 per night (USD)

    Expedia

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  • Gorgeous condo with large private lanai, shared pool, hot tub, BBQ, and tennis
    From $401 per night (USD)

    VRBO

    Gorgeous condo with large private lanai, shared pool, hot tub, BBQ, and tennis

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Grand Champions 7 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...

    From $401 per night (USD)

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  • Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C
    From $386 per night (USD)

    Expedia

    Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Introducing the newest unit in our portfolio! Please visit and be our first review with an introductory Special Rate til ...

    From $386 per night (USD)

    Expedia

    Details
  • Wailea Ekahi Village | 47B
    From $909 per night (USD)

    VRBO

    Wailea Ekahi Village | 47B

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your tropical retreat at Wailea Ekahi Village 47B—an ideal vacation escape for families or a group of friends ...

    From $909 per night (USD)

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    Details
  • Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of Wailea
    From $628 per night (USD)

    Expedia

    Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of Wailea

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Wailea Elua 2007, a stunning 1-bedroom, 2-bath vacation retreat with gorgeous ocean views, a spacious private ...

    From $628 per night (USD)

    Expedia

    Details
  • WE 907 Breathtaking Ocean Views from the Top of Wailea 2BD Amazing Location
    From $471 per night (USD)

    VRBO

    WE 907 Breathtaking Ocean Views from the Top of Wailea 2BD Amazing Location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $471 per night (USD)

    VRBO

    Details
  • Wailea Beach Villas PH107
    From $1331 per night (USD)

    Expedia

    Wailea Beach Villas PH107

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Beach Villas Penthouse 107 is a luxurious haven that embodies the essence of island living, offering breathtaking ...

    From $1331 per night (USD)

    Expedia

    Details
  • Wailea Oceanfront Center Front Row Luxury Retreat
    From $1445 per night (USD)

    VRBO

    Wailea Oceanfront Center Front Row Luxury Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Immerse yourself in the beauty of Maui at this stunning oceanfront property. This 2-bedroom, 2-bathroom condo offers cen ...

    From $1445 per night (USD)

    VRBO

    Details
  • Lovely Palms at Wailea #406, spacious, large lanai, Full A/C, close to beach!
    From $318 per night (USD)

    Expedia

    Lovely Palms at Wailea #406, spacious, large lanai, Full A/C, close to beach!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Located in the highly desirable Palms at Wailea, this delightful condo offers a relaxing retreat for guests. This spacio ...

    From $318 per night (USD)

    Expedia

    Details
  • Condo with soaring ceilings and ocean views
    From $326 per night (USD)

    VRBO

    Condo with soaring ceilings and ocean views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ekolu 404 is a spacious 2-bedroom, 2-bathroom second-floor condo, perfect for up to 6 guests. It features three private ...

    From $326 per night (USD)

    VRBO

    Details
  • Grand Champions #147 Golf Course Views Full Kitchen AC Throughout
    From $330 per night (USD)

    Expedia

    Grand Champions #147 Golf Course Views Full Kitchen AC Throughout

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wailea Grand Champions #147 is a 2 bedroom, 2 bath, ground floor unit with no stairs, it is friendly for seniors or with ...

    From $330 per night (USD)

    Expedia

    Details
  • Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!
    From $1536 per night (USD)

    VRBO

    Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Wailea Elua #1904! This recently renovated luxury beachfront 2 bedroom/2 bath residence is in the heart of Wa ...

    From $1536 per night (USD)

    VRBO

    Details
  • Modern Spacious Beachfront Luxury in Wailea. Family Friendly!
    From $892 per night (USD)

    Expedia

    Modern Spacious Beachfront Luxury in Wailea. Family Friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A modern 2 bedroom, 2 bath condo with extra bunk beds and an amazing ocean view! South Maui is one of the most beautifu ...

    From $892 per night (USD)

    Expedia

    Details
  • Wailea Ekahi 6E-Gorgeous Condo, #1 Location, Serene/Private, steps to Pool/Beach
    Click For Pricing

    VRBO

    Wailea Ekahi 6E-Gorgeous Condo, #1 Location, Serene/Private, steps to Pool/Beach

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    ***Please note: This unit is under NEW ownership. The previous owner had a 10/10 rating with 67 reviews! LOCATION, LO ...

    Click For Pricing

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    Details
  • Ekahi Village-Oceanfront Complex-2 Beds-Balcony-Walk to beach!
    From $439 per night (USD)

    VRBO

    Ekahi Village-Oceanfront Complex-2 Beds-Balcony-Walk to beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    **Limited Summer Special! Relax in our 1BR/1BA condo at Wailea Ekahi Village, perfect for up to 4 guests. This renovated ...

    From $439 per night (USD)

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  • Kihei 3 Bedroom Condo Sleeps 6
    From $1474 per night (USD)

    VRBO

    Kihei 3 Bedroom Condo Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab. Unwind in Kihei at this marvelous co ...

    From $1474 per night (USD)

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    Details
  • Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C
    From $532 per night (USD)

    VRBO

    Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    The Palms at Wailea #2204 has been totally remodeled. This large condo of 1022 sq feet has soaring ceilings and stunning ...

    From $532 per night (USD)

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    Details
  • Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!
    From $1062 per night (USD)

    VRBO

    Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining area ...

    From $1062 per night (USD)

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  • Tropical Wailea Retreat
    From $302 per night (USD)

    VRBO

    Tropical Wailea Retreat

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore ...

    From $302 per night (USD)

    VRBO

    Details
  • Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations
    From $959 per night (USD)

    VRBO

    Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    <p>A short distance from sailing, cycling, and more, this smoke-free condo lets you experience it all. Shops at Wailea i ...

    From $959 per night (USD)

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    Details
  • Wailea Elua Village | 707
    From $929 per night (USD)

    Expedia

    Wailea Elua Village | 707

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ideally situated in a quiet corner along the northern edge of the resort, Wailea Elua Village 707 is just a short stroll ...

    From $929 per night (USD)

    Expedia

    Details
  • Wailea Ekahi Village | 39A
    From $899 per night (USD)

    VRBO

    Wailea Ekahi Village | 39A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush ...

    From $899 per night (USD)

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  • Wailea Elua Village | 2004
    From $681 per night (USD)

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    Wailea Elua Village | 2004

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui's southern coastline. This one-bedroom, ...

    From $681 per night (USD)

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  • Wailea Beach Villas | F202
    From $2416 per night (USD)

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    Wailea Beach Villas | F202

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Wailea Beach Villas F202 is where luxury, style and sophistication blend together in a stunning Maui location just above ...

    From $2416 per night (USD)

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  • Wailea Ekahi Village | 11A
    From $899 per night (USD)

    Expedia

    Wailea Ekahi Village | 11A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 11A offers a truly exceptional and luxurious island getaway on Maui. Situated in the prestigious Wailea res ...

    From $899 per night (USD)

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  • Wailea Ekahi Village | 12A
    From $949 per night (USD)

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    Wailea Ekahi Village | 12A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 12A is an exquisite vacation rental located within the desireable area of Wailea along Maui's southern coas ...

    From $949 per night (USD)

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  • Wailea Ekahi Village | 12C
    From $943 per night (USD)

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    Wailea Ekahi Village | 12C

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village ...

    From $943 per night (USD)

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  • Wailea Ekahi Village | 15A
    From $899 per night (USD)

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    Wailea Ekahi Village | 15A

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Walk to the beach in minutes from this ground floor condo at Wailea Ekahi Village. Slide open the glass lanai doors of ...

    From $899 per night (USD)

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  • Wailea Elua Village | 708
    From $830 per night (USD)

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    Wailea Elua Village | 708

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea commu ...

    From $830 per night (USD)

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    Details
  • Wailea Ekahi Village | 10F
    From $903 per night (USD)

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    Wailea Ekahi Village | 10F

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi Village 10F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathro ...

    From $903 per night (USD)

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  • Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
    From $1547 per night (USD)

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    Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unob ...

    From $1547 per night (USD)

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  • Wailea Ekahi Village | 3A
    From $1053 per night (USD)

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    Wailea Ekahi Village | 3A

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    For a vacation condo that feels like a private home, select this two story residence with a sunken living room and casca ...

    From $1053 per night (USD)

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  • Wailea Elua Village | 1103
    From $842 per night (USD)

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    Wailea Elua Village | 1103

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located within short walking distance to the beach and close to the on-property pickleball court and swimming pool, Wail ...

    From $842 per night (USD)

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  • Wailea Elua Village | 1604
    From $1312 per night (USD)

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    Wailea Elua Village | 1604

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lana ...

    From $1312 per night (USD)

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  • Wailea Ekahi Village | 54B
    From $899 per night (USD)

    Expedia

    Wailea Ekahi Village | 54B

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Ekahi 54B is a luxurious one-bedroom two-bathroom vacation rental offering an exceptional blend of comfort and el ...

    From $899 per night (USD)

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  • Wailea Elua Village | 1303
    From $1353 per night (USD)

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    Wailea Elua Village | 1303

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    When vacationing in Wailea Elua 1303, you’ll feel pampered by the extra touches that await you in this suite featuring m ...

    From $1353 per night (USD)

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  • Wailea Ekolu Village | 1007
    From $890 per night (USD)

    Expedia

    Wailea Ekolu Village | 1007

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for r ...

    From $890 per night (USD)

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  • Wailea Elua Village | 2104
    From $792 per night (USD)

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    Wailea Elua Village | 2104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed ...

    From $792 per night (USD)

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  • Wailea Elua Village | 2006
    From $912 per night (USD)

    Expedia

    Wailea Elua Village | 2006

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifu ...

    From $912 per night (USD)

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    Details
  • Wailea Elua Village | 1502
    From $832 per night (USD)

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    Wailea Elua Village | 1502

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Situated near the center of the resort, Wailea Elua 1502 is siutated near the putting green and central swimming pool. J ...

    From $832 per night (USD)

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  • Wailea Ekahi Village | 38F
    From $680 per night (USD)

    Expedia

    Wailea Ekahi Village | 38F

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui ...

    From $680 per night (USD)

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  • Wailea Elua Village | 1703
    From $1353 per night (USD)

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    Wailea Elua Village | 1703

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach a ...

    From $1353 per night (USD)

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  • Wailea Elua Village | 2012
    From $662 per night (USD)

    Expedia

    Wailea Elua Village | 2012

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, t ...

    From $662 per night (USD)

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  • Wailea Elua Village | 1704
    From $1344 per night (USD)

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    Wailea Elua Village | 1704

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches ...

    From $1344 per night (USD)

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  • Wailea Beach Villas E-302 on Wailea Beach
    From $2915 per night (USD)

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    Wailea Beach Villas E-302 on Wailea Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Modern living, in one of the best locations at Wailea Beach Villas, with outer island and sunset views that are unmatche ...

    From $2915 per night (USD)

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  • Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View
    From $816 per night (USD)

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    Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Polo #406 is a beautiful, comfortable unit overlooking the ocean. It offers breathtaking views of Molokini, West Maui, ...

    From $816 per night (USD)

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  • Wailea Elua Village | 2401
    From $645 per night (USD)

    Expedia

    Wailea Elua Village | 2401

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Completely renovated in 2019, Wailea Elua 2401 is a stunning vacation condo that features a large private wrap-around la ...

    From $645 per night (USD)

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  • Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year
    From $447 per night (USD)

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    Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    2

    Aloha and welcome to our home at The Palms at Wailea. The ocean view will take your breath away the minute you step ins ...

    From $447 per night (USD)

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  • Spring Special! Fantastic Beachfront Wailea Ekahi 2/2
    From $766 per night (USD)

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    Spring Special! Fantastic Beachfront Wailea Ekahi 2/2

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to my sunny Wailea Ekahi Paradise! This unit is a remodeled, expanded and wonderfully furnished 2 bedroom 2 bath ...

    From $766 per night (USD)

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  • Wailea Grand Champions | 84
    From $1027 per night (USD)

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    Wailea Grand Champions | 84

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. Thi ...

    From $1027 per night (USD)

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  • Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!
    From $371 per night (USD)

    Expedia

    Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    E Komo Mai to our luxury 2 bedroom unit on the 2nd floor with a beautiful ocean view and a spacious interior. From our c ...

    From $371 per night (USD)

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  • Grand Champions Condos by KBM
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    Grand Champions Condos by KBM

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    <p>Just a short distance from hiking and biking trails, this smoke-free apartment lets you experience it all. Shops at W ...

    Click For Pricing

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  • Beautifully remodeled ocean view condo in Wailea WE27B
    From $697 per night (USD)

    Expedia

    Beautifully remodeled ocean view condo in Wailea WE27B

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Hawaii Tax ID: TA-072-016-4864-01 TMK: 210080600050 Enjoy this beautifully remodeled luxury unit at Wailea Ekahi! A sh ...

    From $697 per night (USD)

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  • Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!
    From $188 per night (USD)

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    Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Tucked away within the quiet rearward part of this tranquil, low-rise resort and nestled in the Maui tropical greenery t ...

    From $188 per night (USD)

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  • Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full Bath
    From $517 per night (USD)

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    Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full Bath

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Imagine waking to the gentle lull of the trade winds, sunlight streaming through your lanai, and the promise of a perfec ...

    From $517 per night (USD)

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  • Wailea Ekahi 17E | Resort Level Amenities!
    From $344 per night (USD)

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    Wailea Ekahi 17E | Resort Level Amenities!

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    The beauty of sand and sparkling waters and the warm Hawaiian sun is calling your name! Wailea Ekahi 17E is a one bedroo ...

    From $344 per night (USD)

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  • Wailea Beach Villas | B101
    From $3004 per night (USD)

    Expedia

    Wailea Beach Villas | B101

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    You will feel like a rock star in this oceanfront villa with its owner’s gold and platinum records displayed alongside a ...

    From $3004 per night (USD)

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  • Wailea Elua Village | 401
    From $850 per night (USD)

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    Wailea Elua Village | 401

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wailea Elua Village 401 is a stunning vacation rental situated in the luxurious Wailea area of Maui. This ground floor ...

    From $850 per night (USD)

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  • Wailea Ekahi 45B-Summer Special 225/Nt, New Kitch, Lrg Lanai, Pool #3 w/BBQ
    From $409 per night (USD)

    Expedia

    Wailea Ekahi 45B-Summer Special 225/Nt, New Kitch, Lrg Lanai, Pool #3 w/BBQ

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Unit 45B is located in Building 45 on the ground floor. This lovely one bedroom, two bathroom condo has a 400 square fo ...

    From $409 per night (USD)

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  • Prime Beachfront on the Ground Floor, Polo Beach Wailea/Makena #104
    From $882 per night (USD)

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    Prime Beachfront on the Ground Floor, Polo Beach Wailea/Makena #104

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The Polo Beach condos sleep 6 in total. Please call for very latest openings as there may be a new booking in progress. ...

    From $882 per night (USD)

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  • Wailea Elua Village | 904
    From $1392 per night (USD)

    Expedia

    Wailea Elua Village | 904

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Wailea Elua 904 is a stunning vacation rental property that offers a luxurious island getaway. Nestled within the upscal ...

    From $1392 per night (USD)

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  • Beautifully Studio Condo just steps to the Beach.  Stunning Ocean Front Pool.
    From $352 per night (USD)

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    Beautifully Studio Condo just steps to the Beach. Stunning Ocean Front Pool.

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    0

    LOCATION, LOCATION, LOCATION- Our Studio Condo in Building 9 is just steps from the Ocean Front Pool, Pavilion and Oce ...

    From $352 per night (USD)

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  • Treetop Studio 2nd floor, corner unit
    From $188 per night (USD)

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    Treetop Studio 2nd floor, corner unit

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This studio offers private lanai and kitchenette with sink, full size fridge and microwave. King size bed, and remodele ...

    From $188 per night (USD)

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  • Beautiful  Condo  Steps to a Great Beach .  Stunning Pool that is Ocean Front.
    From $515 per night (USD)

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    Beautiful Condo Steps to a Great Beach . Stunning Pool that is Ocean Front.

    Bedrooms:
    0
    Bathrooms:
    1
    Sleeps:
    2

    Enhanced Cleaning recommended by WHO/CDC have been implemented. After thorough cleaning with soap, all surfaces will the ...

    From $515 per night (USD)

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  • Beautiful Ocean View Studio
    From $380 per night (USD)

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    Beautiful Ocean View Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enhanced Cleaning recommended by WHO/CDC have been implemented. After thorough cleaning with soap, all surfaces will t ...

    From $380 per night (USD)

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