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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

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

ALOHA!

Immerse yourself in the warmth of Aloha at Our Maui Condos - Ho'okipa at Wailea Ekolu Village. Discover the true meaning of Hoʻokipa through our exceptional Wailea Ekolu home. Enjoy breathtaking Maui sunsets with panoramic views ...

2 bedroom
2 bathroom
Sleeps 4

from $431

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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

from $453

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Enjoy garden views and ocean glimpses from your private lanai at #138

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 ...

3 bedroom
2 bathroom
Sleeps 6

from $458

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Stunningly Renovated! Ocean View! 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

from $1,199

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Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village

Aloha!

Welcome to our Our Maui Condo! ʻIKE KAI, which means "OCEAN VIEWS," offers a one-bedroom, two-bath, ground floor retreat that will delight even the most discerning traveler.

Nestled in the desirable lower section of the ...

2 bedroom
2 bathroom
Sleeps 4

from $426

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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

from $711

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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

from $1,123

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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

from $1,941

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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

from $1,185

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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

from $2,045

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Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!

This beautiful top floor, Grand Champs condo has one of the best ocean views in the complex. This fully updated 2 bedroom, 2 full bath condo has wonderful panoramic ocean views perfect for sunsets and whale watching. From the extra large, ...

2 bedroom
2 bathroom
Sleeps 4

from $358

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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

from $568

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Luxe Townhome, Ocean Views, Relax by the Pool

- Luxurious two-story townhome with a private elevator and sleeps 10 comfortably
- One of the few villas offering both pool and ocean views
- Prime location near the pool and just minutes from the beach
- Hotel-quality beds with luxury ...

4 bedroom
4 bathroom
Sleeps 10

from $1,444

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Amazing view, Close to the beach, Wailea Ekahi Unit 20i

Condo 1 bedroom, 2 bath (sleeps 4)
PRIME location on the front row in lower Wailea Ekahi, Wailea. Listen to the sound of the waves and enjoy the ocean views. Famous Keawakapu Beach is just steps away! Beautiful ocean views from every room. ...

1 bedroom
2 bathroom
Sleeps 4

from $508

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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

from $885

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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

from $525

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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

from $1,669

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Fantastic unit! 10/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4

This one bedroom, smoke-free condo, is located in Ekahi Village, and is a short (less than 4 minutes) relatively flat walk to the beautiful Keawakapu Beach. The unit is located in the lower village. You can stay on the beach for the day or ...

2 bedroom
1 bathroom
Sleeps 4

from $409

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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

from $2,055

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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

from $555

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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

from $596

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The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!

The Maui Escape is located with views of the upper pool and the spectacular surroundings. The villa's location is the perfect combination of being close enough to view the pool but far enough for privacy. At night the ambiance from the lanai ...

3 bedroom
2 bathroom
Sleeps 6

from $1,651

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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

from $1,748

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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

from $498

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

The Maui Meadows Guesthouse Property is 3/4 mile from (8) premier beaches and features: (4) Bedroom, (5) Bath one story 2700 sq ft house, Proximity to beaches, activities, golf, ...

4 bedroom
5 bathroom
Sleeps 10

from $1,580

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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

from $675

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'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

from $413

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Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium #2301

New living room furniture and lanai furniture - Absolutely Lovely!

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

from $1,082

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PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA

For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly renovated 1536 square foot condo is a spectacular beachfront vacation rental with panoramic ocean...

2 bedroom
2 bathroom
Sleeps 6

from $1,007

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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

from $532

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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

from $1,080

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

This is the one! A real Maui home-away-from-home. If you are looking for an impressive vacation home with new Ohia wood cabinets, cupboards, and accents in the kitchen, new sandstone tile flooring, super quiet new Fleetwood glass doors, new ...

3 bedroom
2 bathroom
Sleeps 6

from $1,487

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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

from $516

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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

from $500

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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

from $1,648

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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

from $555

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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

from $1,769

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Exquisite Oceanview Villa with Resort Amenities in Gated Community

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

from $1,731

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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

from $519

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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

from $503

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🐬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

from $386

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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

from $952

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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

from $903

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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 ...

3 bedroom
2 bathroom
Sleeps 6

from $1,542

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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

from $1,537

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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

from $1,908

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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

from $596

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Captivating Ocean Views from Polo Beach Club 805! Direct beach access.

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

from $1,333

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Wailea Ekahi 40A - 5-Star South Maui Oasis

Welcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even ...

1 bedroom
2 bathroom
Sleeps 4

from $429

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100KContemporaryHawaiian Reno in Wailea-Beach/Golf

Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. ...

2 bedroom
2 bathroom
Sleeps 6

from $433

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