Wailea Vacation Rentals

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

Browse Wailea Vacation Rentals by condo/hotel name:

Ekahi Village
Elua Village
Wailea Grand Champions
Hoolei
Mana Kai
Polo Beach Club
Wailea Ekolu
The Palms at Wailea
Wailea Ekahi
Wailea Beach Villas
Wailea Point

You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.

ALOHA!

Welcome to Our Maui Condo where Hoʻokipa means "hospitality"! You're sure to enjoy our Wailea Ekolu home and the Maui sunsets with SPECTACULAR OCEAN VIEWS of Molokini and the neighboring island of Kahoolawe.

Our condo is ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $544 
View Property  

nNEW KITCHEN REMODEL! Amazing View!

Condo, 1 bedroom + other (See Description) 2 baths (Sleeps 4)

Peace of mind is important for where you are staying. Our cleaning care professionals have been trained to properly follow all CDC, VRHP (Vacation Rental Housekeeping ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $587 
View Property  

Top Floor! 2 bedroom w/ Ocean Views! GC138

Location! Location! Location! Who needs a car?!? This central Wailea location makes it favorable as you can find tennis, golf, retailers at the Shops at Wailea, casual to fine dining restaurants, world's top beaches, and five-star hotels just ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $590 
View Property  

Beautiful Listing! Fully Renovated! STUNNING VIEWS!! Elua 2305

This property is hotel zoned, and not being affected by the recent proposed legislation.

Welcome to Elua 2305. Your ultimate Maui vacation awaits at this fabulous listing! Don’t miss this incredible opportunity to enjoy the very best ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $1,056 
View Property  

Check out the Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village

Aloha!

Welcome to our Our Maui Condo! ʻIKE KAI means "OCEAN VIEWS". This wonderful one bedroom, two bath, ground floor condo with BEAUTIFUL OCEAN VIEWS will satisfy even the most discriminating visitor.

Our condo is located on ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $505 
View Property  

Wailea Ekahi Village | 38F

Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $749 
View Property  

Makena Surf | B106 | Beachfront Resort

Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean's edge. This beautifully appointed residence combines luxury and comfort, featuring elegant tray ceilings, exquisite wood ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $866 
View Property  

Wailea Beach Villas | PH406

Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,945 
View Property  

Wailea Elua Village | 1102

This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to the white-sand Ulua Beach that fronts this property. Be one of the first in the ocean in the ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $799 
View Property  

Wailea Elua Village | 1703

Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,316 
View Property  

Wailea Beach Villas | PH309

Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is ...

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $2,788 
View Property  

Enjoy Beautiful Sunsets with this Ocean View!!

NOTICE: OUR COMPLEX WILL BEGIN ROOF REPLACEMENT ON ALL BUILDINGS BEGINNING MAY 1, 2023. (Our building is scheduled Oct. 27 - Nov. 13). There could be outside construction noise throughout the complex during this time.

This beautiful ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $358 
View Property  

FULL OCEAN VIEW WAILEA

Full renovation of this condo was completed December 2020. Both bathrooms, master bedroom, as well as entire condo painted and replacement of baseboards and door trims throughout.

Bright airy updated large 1 bedroom 2 bath top floor in ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 3
Hawaii> Wailea
from $757 
View Property  

Ocean View, Close to Beach&Pool Sleeps 10

Experience the luxury of a resort community while staying in a home larger than four hotel rooms!! Beach and Snow Rentals offers this spacious 3 bedroom, 3.5 bath two story townhome featuring a private elevator, finely appointed interior, and ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 10
Hawaii> Wailea
from $1,563 
View Property  

Modern Spacious Beachfront Luxury in Wailea. Family Friendly!

A modern 2 bedroom, 2 bath condo w. extra bunk beds and an amazing ocean view!

South Maui is one of the most beautiful destinations in all of Maui and Wailea Ekahi Village is the perfectly-situated, beachside resort we call home . Guests...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,021 
View Property  

Luxurious 2.5 Bedroom Paradise - Wailea Beach Villa

Our home is a spacious 1980 square foot, 2 bedroom/2 bath Wailea Beach Villa with a den that functions as a third bedroom. Located directly above the upper pool with a spectacular garden and pool view, this spectacular unit offers a generous ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,295 
View Property  

Wailea, Oceanfront, Polo Beach Club Condo #403

Location, location, location…. Polo Beach is the premiere condominium that sits at the south end of the Wailea Beach walk, next to the Fairmont Kei Lani resort. Our unit is on the sunny south side of the building, overlooking the pool area and...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Wailea
from $1,357 
View Property  

Stunning Ocean View Wailea Beach Villa- Book & Save

Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect . 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spectacular panoramic ocean view. This elegant 4th Floor Villa is nestled between The Grand Wailea & The Shops at ...

  • 4 bedroom
  • 3 bathroom
  • Sleeps 9
Hawaii> Wailea
from $2,176 
View Property  

Panoramic Ocean View In The Heart Of Wailea On Golf Course

Enjoy spectacular panoramic ocean views from this beautiful condo in a truly private setting! This is one of the best located units in the complex providing unobstructed ocean views from the living area, dining area, kitchen, master bedroom and...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 5
Hawaii> Wailea
from $626 
View Property  

Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier

This villa at Ho'olei was renovated in 2024. The renovations are extensive. New extra large kitchen island with ocean view seating: all new appliances in the kitchen: new stone counter tops throughout the home: new cabinets throughout the home: ...

  • 3 bedroom
  • 4 bathroom
  • Sleeps 7
Hawaii> Wailea
from $1,567 
View Property  

Amazing location! Hear the waves from the quiet and private lanai! 19C

This one bedroom (Unit 19C), smoke-free condo , is located in Ekahi Village, and is a short (less than 4 minutes) relatively flat walk to the beautiful Keawakapu Beach. You can stay on the beach for the day or enjoy the amazing new waterfront ...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> wailea
from $449 
View Property  

DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.

Beachfront Wailea: Ocean Panoramic & Outer Island Views, Penthouse K-208, 4 Full Bedrooms & 3 Full Baths; Total 3892 S.F.
READ ALL OUR REVIEWS for YOUR BEST INSIGHTS, PLEASE.
The Wailea Beach Villas Finest Upgrades. Complete Renovation. ...

  • 4 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $2,449 
View Property  

Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern

Experience the beauty of Wailea from the moment you arrive in your spacious and stylish villa. Situated in a secluded position of the Grand Champions resort property you can relax on the lanai and take in the views, get to that book you’ve ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $583 
View Property  

Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center

Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in beautiful Wailea on the sunny, southwestern shore of Maui. Ho’olei is the ultimate dream home in paradise!

This recently renovated ...

  • 4 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,524 
View Property  

Luxury at its Best with Big Ocean Views!!

Aloha & welcome to the Wailea Diamond Suite at Ekolu Village #305!

The moment you step through the door you’ll know you’ve come home to luxury in this elegant 2 bedroom, 2 bath condo. Each bedroom features its own unique bath, private...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $596 
View Property  

MODERN MAUI I404! - MODERN LUXURY AND PANORAMIC OCEAN VIEWS

Private Paradise Villas personally manages an array of exceptional villas within this award-winning location, offering a curated and exclusive collection of 2.5 to 4 bedroom villas, most with panoramic ocean views. Private Paradise Villas is in ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $2,085 
View Property  

No stairs inside or out! Beautifully remodeled Palms at Wailea 503

We completed our kitchen remodel in December 2023! Check out the photos!

Welcome to Palms at Wailea 503, your beautifully remodeled sanctuary in paradise! This is a two-bedroom two-bathroom condo in the prestigious Wailea Resort area. One...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $564 
View Property  

Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area

Maui is open! Only the Lahaina town area is closed from the August 2023 fire but lots to do and see and enjoy elsewhere. Your vacation will be unaffected other than walking thru old Lahaina town for an afternoon, which is a 50 minute drive ...

  • 4 bedroom
  • 5 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,632 
View Property  

14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!

Wailea Ekahi #14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home! You will feel like you are on top of the world as you look out from the second floor ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $675 
View Property  

'Best Vacation Ever' Say Our Guests! Special May Rates

You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit was completely remodeled in 2020. It is immaculate, impeccably maintained and ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $442 
View Property  

Gorgeous Elua 2 Bdrm+2 Bath 1st Floor, Ocean View Paradise Condominium #2301

New living room furniture and lanai furniture - Absolutely Lovley!

Wailea Elua Village #2301 is a premier vacation condominium located in Elua Village which is directly on the sugar sand of Ulua beach in Wailea. This impressive ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,211 
View Property  

Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion Villas

Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer in a 2 bedroom + 2 bath category. Upgraded in ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $708 
View Property  

Fresh and New Luxury Elua Village 2 Bdrm+2 Bath Paradise Condominium #907

New, New, New! New furniture, new electronics, new beds, mattresses and linens, paint and artwork. Sooooo close to the beach! Treat yourself to the best that Elua Village has to offer. You and your guests will enjoy the short walk to the beach...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,314 
View Property  

Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai

This is the one! A real Maui home-away-from-home. Plus, 5th night free for the duration of your visit through October 31, 2024! If you are looking for an impressive vacation home with new Ohia wood cabinets, cupboards, and accents in the ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,713 
View Property  

Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D

Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!

Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with the best of everything Maui has to offer: spectacular views, privacy and a short stroll ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 2
Hawaii> Wailea
from $541 
View Property  

Wailea Ekahi Village | 39A

If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush row of towering tropical plants. This hidden gem provides a tranquil oasis perfect for unwinding after a full day exploring...

  • 2 bedroom
  • 1 bathroom
  • Sleeps 4
Hawaii> Wailea
from $435 
View Property  

OCEANVIEWS, FRESH UPGRADES AT THE LUXURIOUS GRAND SEASCAPE K407!!

Situated in the centrally located "Penthouse" building on the 4th floor in a west-facing ocean view corner location with breathtakingly beautiful panoramic ocean and sunset views, this 2.5 bedroom (king bed in each bedroom plus 2 twin beds the ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $2,158 
View Property  

Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba

Wailea Rentals presents: Wailea Ekahi Village 8E - Ekahi means #1 in Hawaiian and that is exactly what Ekahi Village is - 1 of Wailea's top luxury beachfront condominium resorts. Located directly on Keawakapu Beach at the north end of Wailea on ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $840 
View Property  

LUXURY OCEANFRONT MAKENA SURF - 3 BR/3 BA - CONTACT OWNER FOR SPECIAL RATE

Welcome to the newly renovated, top floor ''Turquoise Cove'' Villa - Makena Surf F301. This amazing property has unsurpassed ocean views, with a unique, double wrap-around lanai, perfect for enjoying tropical sunsets or catching the occasional ...

  • 3 bedroom
  • 3 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,750 
View Property  

Luxurious Ocean View Villa at Ho'olei! Experience Hoolei 17-3

This property is hotel zoned, and not being affected by the recent proposed legislation.

Located in highly desirable secluded area of neighborhood your villa welcomes you with spacious floor plan and sweeping ocean views. Marvel at the ...

  • 3 bedroom
  • 4 bathroom
  • Sleeps 8
Hawaii> Wailea
from $1,569 
View Property  

Ocean View, Steps away from the pool

"COVID-19: Dear travelers. Even though we have always maintained an exceptionally clean property, you can rest assured that we are following the guidelines of the CDC and Expedia/VRBO for enhanced cleaning and disinfecting of short term ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $677 
View Property  

Luxurious, 2 bedroom / 2 bath, FULL Ocean View Wailea Condo

Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and desirable complex that is exceptionally quiet and free of any traffic noise. This property is ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $504 
View Property  

🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈

Wailea Grand Champions Villas -- Condo #188

Aloha!

You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of High-end amenities while enjoying the island? We welcome you to share our ...

  • 1 bedroom
  • 2 bathroom
  • Sleeps 4
Hawaii> Wailea
from $460 
View Property  

Makena Surf | C105 | Beachfront Resort

Enter the cool marbled foyer of Makena Surf C105, a luxurious 1,600 sq. ft. ocean view vacation rental on the first floor of the prestigious Makena Surf resort. As you make your way to the elegant living area, you'll be greeted by sliding doors ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,431 
View Property  

Polo Beach Club | 409

Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $890 
View Property  

Wailea Beach Villas | PH111

Curated with our guests in mind, Wailea Beach Villas PH111's outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine ...

  • 4 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,354 
View Property  

Wailea Beach Villas | PH210

Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious ...

  • 3 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,652 
View Property  

Wailea Beach Villas | PH306

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

  • 4 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $2,033 
View Property  

COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!

**FAMILY FRIENDLY**

If you are looking for a modern, luxurious retreat in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely gutted to the studs and every item was purchased brand new. Guests can ...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $641 
View Property  

Direct Ocean Front Polo Beach 805!

Captivating Ocean Views from Polo Beach Club 805! Direct ocean front location with beach access.

You will marvel at the exquisite furnishings and decor at Polo Beach Club 805.
As you enter, you are greeted by the sophisticated style of...

  • 2 bedroom
  • 2 bathroom
  • Sleeps 6
Hawaii> Wailea
from $1,370 
View Property  

Showing 1 of 7 pages.

Home
Vacation Rentals
Activities
About
Privacy Policy
Terms
Disclaimer
Sitemap
To-Hawaii.com © 2006-2025
back-top