Maui Resort Rentals: Polo Beach Club 608 – Luxurious 6th-Floor Oceanfront 2BR w/ Stunning Ocean Views!From $1,006/night · Sleeps 6
South Maui Luxury Villas and Condos
Wailea Vacation Rentals
Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden stay, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Hoolei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities right for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-quiet surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic stay or a long-term tropical escape, Wailea vacation rentals provide the right home base for a luxurious island experience.
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Wailea Vacation Rentals Listings
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Wailea Vacation Rentals Map
Maui Resort Rentals: Polo Beach Club 608 – Luxurious 6th-Floor Oceanfront 2BR w/ Stunning Ocean Views!From $1,006/night · Sleeps 6
Maui Kamaole I217 2brm/2bath Executive Vacation HomeFrom $407/night · Sleeps 6
Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbqFrom $536/night · Sleeps 4
NEWLY REMODELED! Partial Ocean View condo along the golf courseFrom $540/night · Sleeps 6
New Listing! Ekahi 26B-Spacious & Family Friendly | Ground-Floor Garden OasisFrom $396/night · Sleeps 4
I.P.M Presents: Villa C302 - Spectacular NEW Remodel + Great Ocean View!From $1,595/night · Sleeps 8
Fully Remodeled Modern Island Style!From $219/night · Sleeps 6
Your OWN Luxury Private Resort Within a Resort at Seaglass 810 at Andaz MauiFrom $2,950/night · Sleeps 8
New Listing:Tall ceilings, ocean views, and more!From $395/night · Sleeps 6
Elua Resort 1904: Front of the Front Row...Perfect Sunsets & Privacy!From $1,495/night · Sleeps 6
Luxurious & Spacious Ocean VistasFrom $1,278/night · Sleeps 6
5-4 thru 5-14 249USD Gorgeous Remodel, Oct 2024 BOSE SOUND STEPS TO POOL &BEACHFrom $235/night · Sleeps 4
Breath taking ocean and volcano views! Pool,Close to beaches and everything elseFrom $1,193/night · Sleeps 6
Sale!! The Perfect Hawaii Location for a Relaxing Getaway now on Sale!!From $219/night · Sleeps 4
Just another day in Paradise!From $428/night · Sleeps 6
2BR, 2 BA Ocean View, Reduced Rates for 2026From $325/night · Sleeps 6
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, LegalFrom $593/night · Sleeps 7
Aloha Maui! We are OPEN and LOVE visitors. Best Views at the Palms!!From $501/night · Sleeps 4
Beautifully Updated 3 Bedroom Villa on Fairway with Ocean ViewFrom $524/night · Sleeps 8
Top-floor Maui condo with mountain, ocean, and golf course views. Sleeps six!From $130/night · Sleeps 4
Sweeping Ocean Views, High-end, Private, Prime Location, Deal!From $199/night · Sleeps 2
Spring/Summer Fill in Special 249/nt Updated Designer Condo w/ Ocean ViewsFrom $306/night · Sleeps 4
Tropical Paradise in Luxurious 1br, 2ba Ground Floor Unit, Garden View, Palms 801From $273/night · Sleeps 3
SPECTACULAR VIEW LE PENTHOUSE 513B Luxury KING Bed OCEAN FRONT UPSCALE REMODELFrom $189/night · Sleeps 4
Upscale and Elegant VistasFrom $546/night · Sleeps 4
Ocean Views, AC in every room, remodeled,From $332/night · Sleeps 6
Palms 306 Ocean Views, 5 Star Reviews: RemodeledFrom $318/night · Sleeps 6
Remodeled-Large Lanai-Ground Floor-Ac-Ocean Views-Meticulous CleaningFrom $389/night · Sleeps 6
STUNNING OCEAN VIEW CONDO! Fully Remodeled! Ground!Private!Bunks!Large Lanai!From $395/night · Sleeps 4
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!From $1,286/night · Sleeps 10
Paradise is Here! Big Ocean Views in newly remodeled luxury condoFrom $420/night · Sleeps 4
Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!From $512/night · Sleeps 4
Ocean Views 2BR, Ground Floor & A/C! Ekolu 1405!From $231/night · Sleeps 4
From $1,006/night
Maui Resort Rentals: Polo Beach Club 608 – Luxurious 6th-Floor Oceanfront 2BR w/ Stunning Ocean Views!
Kihei, Hawaii
★★★★★ 10.0/10 · 22 reviews
Boasting a stunning Wailea oceanfront location and a lavish interior, this 2BR/2BA residence delivers stunning Pacific Ocean views from nearly every...
From $407/night
Maui Kamaole I217 2brm/2bath Executive Vacation Home
Kihei, Hawaii
★★★★★ 10.0/10 · 20 reviews
Treat yourself to luxury on a Budget in a custom furnished Wailea-quality executive vacation home in a quiet complex across the street from Kamaole...
From $536/night
Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 16 reviews
Wailea Grand Champions Villas are the perfect place for vacation. Set amid Wailea’s Blue Golf Course and adjoining Wailea Tennis Club, this property...
From $540/night
NEWLY REMODELED! Partial Ocean View condo along the golf course
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 14 reviews
This newly remodeled 3 bedroom 2 bath condo located in the heart of Wailea is the perfect vacation oasis for your island getaway. This condo...
From $396/night
New Listing! Ekahi 26B-Spacious & Family Friendly | Ground-Floor Garden Oasis
Kihei, Hawaii
★★★★★ 10.0/10 · 13 reviews
Your Maui vacation should be exciting and stress-free from the moment you book. We Make Booking Easy!>Flexibility: Plans change, life takes turns....
From $1,595/night
I.P.M Presents: Villa C302 - Spectacular NEW Remodel + Great Ocean View!
Kihei, Hawaii
★★★★★ 10.0/10 · 12 reviews
SECURE YOUR RESERVATION WITHIN MINUTESSAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES WAILEA...
From $219/night
Fully Remodeled Modern Island Style!
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 10 reviews
Aloha and welcome to our condo, the Palms at Wailea 606. We’re looking forward to hosting you and making your vacation fun and enjoyable.The Palms at...
From $2,950/night
Your OWN Luxury Private Resort Within a Resort at Seaglass 810 at Andaz Maui
Kihei, Hawaii
★★★★★ 10.0/10 · 8 reviews
Tucked within one of Wailea's most exclusive beachfront communities, SeaGlass Villa 810 at Andaz Maui Wailea Resort is a privately-owned and...
From $395/night
New Listing:Tall ceilings, ocean views, and more!
Kihei, Hawaii
★★★★★ 10.0/10 · 3 reviews
Ekolu 404 is a spacious 2-bedroom, 2-bathroom second-floor condo, perfect for up to 6 guests. It features three private lanais, air-conditioning, and...
From $1,495/night
Elua Resort 1904: Front of the Front Row...Perfect Sunsets & Privacy!
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 3 reviews
Welcome to Wailea Elua #1904! This recently renovated luxury beachfront 2 bedroom/2 bath residence is in the heart of Wailea on Maui’s Sunny South...
From $1,278/night
Luxurious & Spacious Ocean Vistas
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 2 reviews
Summary:Beautifully remodeled and outfitted! This elegant 2-bedroom, 2-bath condo features upscale touches with magnificent ocean views. Located...
From $235/night
5-4 thru 5-14 249USD Gorgeous Remodel, Oct 2024 BOSE SOUND STEPS TO POOL &BEACH
Kihei, Hawaii
★★★★★ 9.8/10 · 186 reviews
Luxury Wailea Retreat at The Palms – Sunrise over Haleakalā and Sunset ViewsWelcome to my beautifully remodeled home at The Palms at Wailea, one of...
From $1,193/night
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Kihei, Hawaii
★★★★★ 9.8/10 · 179 reviews
PERMIT NUMBER: BBKM 2014/0001 TAX ID NUMBER TA-030-667-5712-01 About the propertyWe Highly recommend Travel insuranceCheck out our website at...
From $219/night
Sale!! The Perfect Hawaii Location for a Relaxing Getaway now on Sale!!
Wailea-Makena, Hawaii
★★★★★ 9.8/10 · 122 reviews
Aloha, E Komo MaiSpecial DISCOUNTED Rates for Summer 2026! Book quickly before they are gone.Welcome to Hale Makamae-Maui, a luxury first floor condo...
From $428/night
Just another day in Paradise!
Wailea-Makena, Hawaii
★★★★★ 9.8/10 · 121 reviews
The Palms at Wailea #1305 is a beautiful 2 bedroom 2 bath air conditioned condo located on Maui's sunny, southwest shore. From the lanai, you have a...
From $325/night
2BR, 2 BA Ocean View, Reduced Rates for 2026
kihei, Hawaii
★★★★★ 9.8/10 · 103 reviews
This is our 2nd Floor, Ocean view condo. There is a condo above this unit. You have a designated parking spot directly in front of the condo. Please...
From $593/night
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
Kihei, Hawaii
★★★★★ 9.8/10 · 92 reviews
Welcome to the Cloud 9 Beach Home.Your support is appreciated as a small private family owner who lives on Maui instead of renting from a large...
From $501/night
Aloha Maui! We are OPEN and LOVE visitors. Best Views at the Palms!!
Kihei, Hawaii
★★★★★ 9.8/10 · 86 reviews
Condo 1506. This 2 bedroom 2 bath is perfect for your stay on Maui. Enjoy the sweeping ocean views from the lanai with some of the worlds best...
From $524/night
Beautifully Updated 3 Bedroom Villa on Fairway with Ocean View
KIHEI, Hawaii
★★★★★ 9.8/10 · 78 reviews
MAUI IS OPEN AND WELCOMING — Despite rumors, short-term rentals are still legal-the island and people needs your help to rebuild after the horrific...
From $130/night
Top-floor Maui condo with mountain, ocean, and golf course views. Sleeps six!
Kihei, Hawaii
★★★★★ 9.8/10 · 69 reviews
Relax in paradise at this beautifully appointed golf-front Wailea condo overlooking the first fairway of the Wailea Blue Golf Course. Enjoy sunset...
From $199/night
Sweeping Ocean Views, High-end, Private, Prime Location, Deal!
Kihei, Hawaii
★★★★★ 9.8/10 · 60 reviews
Unit: Wailea Ekolu 507 | Maui GuidebookCommitted To Clean We’re committed to enhanced cleaning protocols developed in partnership with experts in...
From $306/night
Spring/Summer Fill in Special 249/nt Updated Designer Condo w/ Ocean Views
Wailea-Makena, Hawaii
★★★★★ 9.8/10 · 57 reviews
Welcome to Grand Champions 79! Located in the lush Wailea resort area, this 1 bedroom/two bath villa has been completely updated with new...
From $273/night
Tropical Paradise in Luxurious 1br, 2ba Ground Floor Unit, Garden View, Palms 801
Kihei, Hawaii
★★★★★ 9.8/10 · 38 reviews
* * * * The Palms at Wailea Pool Area will be Closed for Annual Maintenance Tuesday, Sept,. 15th through Friday, Sept,.18th 2026. The Pool Area Will...
From $189/night
SPECTACULAR VIEW LE PENTHOUSE 513B Luxury KING Bed OCEAN FRONT UPSCALE REMODEL
Kihei, Hawaii
★★★★★ 9.8/10 · 12 reviews
'LE PENTHOUSE' - BREATHTAKING VIEW- WHY STAY IN A CONDO...WHEN YOU CAN STAY IN LE PENTHOUSE! READ OUR REVIEWS, STAY IN UPSCALE WAILEA STYLE...
From $546/night
Upscale and Elegant Vistas
Kihei, Hawaii
★★★★★ 9.8/10 · 7 reviews
Summary:Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled and...
From $332/night
Ocean Views, AC in every room, remodeled,
Wailea, Maui, Hawaii
★★★★★ 9.6/10 · 106 reviews
The Palms at Wailea 504 the most sought after complex in Wailea. Newly Remodeled, New AC in every room, Walk to Beach, AmazingOcean Views5 Star...
From $318/night
Palms 306 Ocean Views, 5 Star Reviews: Remodeled
Maui, Hawaii
★★★★★ 9.6/10 · 91 reviews
AMAZING 2 BEDROOM 2 BATH CONDO IN POPULAR PALMS AT WAILEA. SLEEPS UP TO 6 PERSONS. Largest 2 bedrooms in area.This two-bedroom villa boasts stunning...
From $389/night
Remodeled-Large Lanai-Ground Floor-Ac-Ocean Views-Meticulous Cleaning
Kihei, Hawaii
★★★★★ 9.6/10 · 88 reviews
Book with confidence. Wailea Ekahi 46 B is a luxurious 1100 sq. ft. condo. This condo is managed by PMI Maui, a local Real Estate Brokerage that...
From $395/night
STUNNING OCEAN VIEW CONDO! Fully Remodeled! Ground!Private!Bunks!Large Lanai!
Kihei, Hawaii
★★★★★ 9.6/10 · 78 reviews
EKAHI 51B Wailea Ekahi 51B is a luxury high end condo in the highly sought after ocean front complex Wailea Ekahi Village. We purchased this condo...
From $1,286/night
Luxurious Ho'olei 12-2, Lush View, Close to Pool, Sleeps 8 in beds, Central AC!
Kihei, Hawaii
★★★★★ 9.6/10 · 77 reviews
Indulge in a tropical retreat at Ho'olei 12-2 in Wailea, Maui! This opulent 3-bedroom, 3.5-bathroom vacation rental, showcasing the Maile floor plan...
From $420/night
Paradise is Here! Big Ocean Views in newly remodeled luxury condo
Kihei, Hawaii
★★★★★ 9.6/10 · 61 reviews
Condo 1504. This 2 bedroom 2 bath is perfect for your stay on Maui. Enjoy the sweeping ocean views from the lanai with some of the worlds best...
From $512/night
Extraordinary Molokini Views, Spectacular Renovation, New Split AC, Ocean Views!
Kihei, Hawaii
★★★★★ 9.6/10 · 55 reviews
Wailea Ekolu 102 is a bright and airy corner unit showcases spectacular, unobstructed forever ocean views that take in the sunken volcanic crescent...
From $231/night
Ocean Views 2BR, Ground Floor & A/C! Ekolu 1405!
Kihei, Hawaii
★★★★★ 9.6/10 · 48 reviews
Conveniently located on the ground floor, you can soak in the ocean view while relaxing on a chaise lounge chair on the lanai while watching the...