Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
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 retreat, 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
- Ho'olei 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 perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Ocean Views at Wailea Elua 2109 Serene and Desirable!
This property is hotel zoned, and not being affected by the recent proposed legislation.Enjoy Dazzling Ocean and Sunset Views from Highly Desirable Wailea Elua 2109!! Perfectly located atop one of the most incredible snorkeling beaches in South Maui, this 2 bed/2 bath...
Wailea Ekahi Village 50E - Relaxing Ocean and Mountain Views
Welcome to Wailea Ekahi 50E, our deluxe condo for two. We are on the 2nd (top) floor with beautiful ocean and garden views and wonderful tropical breezes. In addition, there are ceiling fans throughout the unit.The large living room-dining room is beautifully furnished...
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms
Features of our 3300 sq condo include: Two full master suites Second and Third bedroom can have two twins or king sized bedFourth Bedroom is queen sized bedWaterworks Bathrooms with large soaking tubStudio Becker Kitchen with 2 subzero refrigerators, Gaggenau Electric...
April Special: Beautiful, Palms At Wailea Condo #608- 2BR/2BA,Great Location!
The Aloha Spirit is Alive and Well in Maui! It's absolutely beautiful. The best beaches , clean air, amazing sunsets, rainbows, humpback whales and wonderful hiking, along with the best restaurants. The people are the best! Lahaina is gone but memories will always be...
Tranquil Groundfloor Retreat - Wailea Ekolu Village 401 - Close to Pool & BBQ!
Wailea Ekolu #401 – Your Ocean View Wailea RetreatSurround yourself with sunshine, palm trees, and endless ocean views at Wailea Ekolu #401. This spacious two-bedroom, two-bathroom ground-level condo offers a serene island escape in one of Maui’s most desirable resort...
Walk to the Beach, Shops, Pool | Wailea Elua 2008
Wailea Elua Village 2008 is a luxurious vacation rental situated along the southern coastline of Maui in the desirable Wailea region. This elegant condo offers a serene retreat for travelers seeking a blend of comfort and natural beauty. The interior of this one-bedroom...
Wailea Elua Village 1303 - 2 Bedroom Oceanfront Condo
When vacationing in Wailea Elua 1303, youâll feel pampered by the extra touches that await you in this suite featuring modern comforts throughout. For example, readers will enjoy the ownerâs book selection and the individual, overhead reading lights in the master...
Sunset Ocean Views | Whale Watching | Wailea Ekahi 12A
Wailea Ekahi 12A is an exquisite vacation rental located within the desireable area of Wailea along Maui\'s southern coastline. This upgraded, split-level one-bedroom vacation rental offers a perfect blend of luxury and comfort, making it an ideal retreat for travelers...
Wailea Ekahi 11A | Four Pools | Resort Amenities
Wailea Ekahi 11A offers a truly exceptional and luxurious island getaway on Maui. Situated in the prestigious Wailea resort community, this spacious and elegantly-appointed condo provides the perfect balance of upscale amenities and serene tropical ambiance. As you step...
Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-Story in Beautiful Wailea
Welcome to Wailea Ekolu 1514 - a spacious, two-story luxury condo designed for travelers seeking comfort, privacy, and jaw-dropping ocean views. This townhome-style villa boasts one of the most private floor plans in the community, with no shared walls and no unit...
Escape to Serenity – Oceanview 1 Bedroom 2 Bath at Wailea Ekahi 48-E, Sleeps 4
Unwind in this gorgeous second-floor, 1-bedroom, 2-bathroom corner unit with breathtaking ocean views and lush tropical gardens right from your private lanai. "Serenity" offers the perfect blend of comfort and elegance, with bright natural light, vaulted ceilings, and...
Wailea Ike by AvantStay | Walk to the Beach | Balcony w/ Views
Pack your swimwear and prepare for an unforgettable getaway at this newly renovated condo, where every morning greets you with stunning balcony views of lush landscapes rolling down to the ocean. This condo is within walking distance of the beach, the Wailea shops,...
KBM Resorts | FREE CAR | Wailea Elua | 2-Bedroom Condo Condo with Luxury Amenities! WEV-2009
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Unique Private Ocean View House With Pool - Walking Distance To Wailea Resorts
Wailea Freedom House is pure and simple elegance in an unmatched location backing onto the Wailea Blue Golf Course. This home has a large heated swimming pool with beautiful ocean views from the spacious pool deck area and upstairs lanai. The unique architecture boasts...
Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
The tropical splendor surrounding Grand Champion Villas is a paradise. Wailea, near Kihei is where you can play 54 holes of championship golf and sink a birdie while enjoying spectacular ocean views. Service at the famed Wailea's Tennis Club, eleven courts are lit for...
Redesigned 1BD/2BA condo with Haleakala views, near Wailea's beaches + dining
Grand Champions 136 is situated in a lush tropical setting. This 1 bedroom / 2 bathroom is located on the top floor with wonderful views of Haleakala. This condo is newly redesigned and furnished. It is the perfect setting for couples and small families. Its convenient...
Hidden Gem! Beautifully upgraded, Top floor! Palms at Wailea 2106
Fabulous condo! This luxury, private unit is located on the top floor and has all the amenities this popular complex affords.This spacious 2 bedroom 2 bath unit has approximately 1475 sq. ft. of lanai and living area! The spacious primary suite features a king bed and...
Tranquil Ground-Floor Retreat: Wailea Elua 105, Set in an Enchanting Property
Wailea Elua #105 – Ocean View Luxury and Secluded Serenity in the Heart of WaileaWelcome to Wailea Elua #105, a beautifully remodeled 2-bedroom, 2-bathroom ground-floor ocean view condo perfectly positioned at the peaceful southeast corner of Wailea Elua Village. This...
Stunning Ground-Level Oasis W/ Breathtaking Oceanfront Views - Wailea Elua 1403
Wailea Elua #1403 – Ocean View Elegance Just Steps from the BeachDiscover beachfront luxury and refined style at Wailea Elua #1403, a completely rebuilt ground-floor condo offering unobstructed ocean views and a front-row seat to the best of Wailea. Thoughtfully...
Wailea Ekahi 9A | Hot tub | Pool | Sunset Views
Welcome to Wailea Ekahi 9A, a charming vacation rental nestled in the heart of Wailea. This meticulously maintained one-bedroom, one-bathroom condo offers a perfect blend of comfort, style, and convenience, making it an ideal retreat for couples or small families...
Garden Studio Steps From The Beach - Wailea Ekahi 4B
Wailea Ekahi 4B is a charming ground-floor vacation studio nestled on a gentle slope in the picturesque Wailea Ekahi Village. This island hideaway offers a unique blend of accessibility and privacy, featuring a secluded back lanai enveloped by lush treetops, creating an...
Stay Longer, Save More at Palms at Wailea 1405
Escape to paradise in our luxurious ocean-view condo at the Palms at Wailea. Enjoy stunning sunsets, resort amenities, and the perfect Maui getaway with our special offer. Make lasting memories with an extended stay - book five nights and receive your sixth night...
Updated Wailea Condo in Oceanfront Complex!
Enjoy your open and airy living area with breathtaking views of the picturesque foliage through your lanai door in unit 52A! Ample seating available as the dining table for four and two seats at the bar area provide comfort and relaxation as you entertain family and...
Unforgettable Maui Escape: Experience Wailea Elua 1402, Your Oceanfront Haven!
Wailea Elua #1402 – Oceanfront Luxury with Spectacular ViewsIf you're searching for an exceptional oceanfront condo on Maui, look no further than Wailea Elua #1402. Nestled within the highly coveted Wailea Elua Village, this second-floor, 1-bedroom, 1-bathroom unit...
Your Island Sanctuary: Spacious Ground-Floor Condo at Wailea Elua #2201
Wailea Elua #2201 – Spacious Island Comfort with Partial Ocean ViewsWelcome to Wailea Elua Village #2201, a beautifully upgraded ground-floor condo nestled within one of Wailea’s most exclusive beachfront communities. This spacious two-bedroom, two-bathroom retreat...
Wailea Condo Great for Families
Discover the perfect blend of elegance and comfort at Wailea Ekahi 20H, a beautifully decorated two-bedroom, two-bathroom vacation rental in the prestigious Wailea community. This charming second floor condo with vaulted ceilings offers a tranquil escape with all the...
Palms at Wailea 601, Perfect Location in Wailea! Ground Floor 2 Bedroom!
Palms at Wailea 601 offers the perfect location in Wailea. This 2-bedroom/2-bath ground level unit surrounded by the lush landscaping makes this a great Hawaiian getaway!Maui's most exclusive location with the best weather is the award-winning Wailea Resort. Ideally...
Spacious 2 bedroom 2 bath Palms at Wailea 1703
Book with us and come to Maui to explore everything we have to offer!Enjoy the beautiful lanai and grounds of the Palms at Wailea with this elegant vaulted ceiling two bedroom two bath condominium in north Wailea. The gardens are spectacular and include a beautiful pool...
GC 179 Relaxing 3Bedroom Wailea Condo w AC Pools Hot Tub
Grand Champions 179 3Bedroom, 2Bathroom, Corner Unit Set Amidst the 18-Hole Wailea Blue Golf Course. Walk to 5-Star Resorts, Restaurants, and Luxury Shopping at the Shops at Wailea Professionally managed by Maui Paradise Properties. Grand Champions 179 is the perfect...
Beautifully Remodeled Wailea Condo Perfect for your Family Vacation
Hawaii Tax ID: TA-043-585-3312-01TMK: 210080770146Beautifully remodeled second floor unit is perfect for your family vacation. Nice and quiet unit with amazing hillside partial ocean views. This unit will surely make your vacation memorable. Great location for...
Amazing! Beautifully Remodeled and Upgraded! Palms at Wailea 403
This cool, ground floor condominium is the most spacious 1200 sq ft two-bedroom 'C' plan, with sunken living room, brand new designer furniture, and extensive travertine and granite surfaces. Oceanic Time Warner cable, internet, phone, and Wi-Fi.Both kitchen and living...
Beautifully Decorated! Very private! Partial Ocean View! Palms at Wailea 2202
The main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the Shores of Maui. Very spacious and open, bringing the outdoors into your living room and kitchen! This unit is situated in the highly sought-after complex....
Wailea Ekahi 46F Spacious 2 bedroom 2 Bath Condo in Wailea
Wailea Ekahi - Beautiful Garden and Ocean Views from this comforting unit! Nice 2 bedroom, 2 bath condo over looking the top pool area. Take pathways through the open garden that leads to the oceanfront pavilion and long pleasurable strolls on the beach of Keawakapu....
Wailea Ekahi 48C ~ 1 Bedroom 2 Bath Wailea Condo!
Wailea Ekahi Village - Spacious one bedroom, two bath condo with a enchanting garden view located in the Upper Village. New carpet throughout the unit. Master bedroom boast a King size bed. Plus there is a bonus sofa sleeper in living room. Full size washer/dryer, air...
NEW!! Wailea Ekolu Ocean Suite 207 with AC and Ocean Views
PRICE REDUCED!!! Wailea Ekolu #207 is a luxurious accommodation located in the heart of Wailea, offering breathtaking views of the Pacific Ocean. The name “Ekolu” holds significance as it means “three” in Hawaiian, representing the fact that it was the third complex...
WE 1509 Beautifully Remodeled Wailea 2BD w Ocean Views AC Pools Golf Course
Wailea Ekolu 1509 Luxurious 2Bedroom Wailea Villa on The Wailea Blue Golf Course with Expansive Occean Views, AC and Pools. Close to Beaches, Shops, Restaurants, Tennis Are you planning your next Maui vacation and have your sights set on the Wailea area? Do you like...
Palms at Wailea 1302! Top Floor Condo with Amazing Garden and Ocean Views!
Top floor condo, #1302 overlooks the lush, landscaped grounds of Palms at Wailea out to a beautiful view of the Pacific Ocean. Watch whales breaching in Winter months and enjoy glorious sunsets year-round.Plenty of windows and glass doors throughout make this home a...
Prime Wailea Location! Split AC! Wailea Ekahi 36E
Wailea Ekahi 36B is a great ground floor location with lush garden views. This 1bedroom/2 bath condo offers the perfect Hawaiian retreat!Welcome to Ekahi 36B! This lovely condo offers everything you need for your Hawaiian Holiday! You will fall in love with this garden...
Wailea Grand Champions 116 - Professional Managed
Wailea Grand Champions 116 is a luxurious vacation rental located along the southern coast of Maui in the desirable tourist area of Wailea. This beautifully appointed one-bedroom, two-bathroom condo accommodates up to four guests, making it ideal for families or groups...
Wailea Elua 401 | Ocean Views | Pool | Hot Tub
Wailea Elua Village 401 is a stunning vacation rental situated in the luxurious Wailea area of Maui. This ground floor two-bedroom, two-bathroom condo is surrounded by tropical views of beautifully mainucred grounds and the South Maui coastline. The condo features an...
Ocean Views in the Heart of Wailea | Elua Village 2005
Wailea Elua Village 2005 is a stunning two-bedroom, two-bathroom vacation rental located in the desirable Wailea region of Maui. This beautifully appointed condo offers a perfect blend of luxury and comfort. The spacious interior features an open-concept design that...
3BD Wailea Villa - Great for Families
Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant ocean view penthouse spans 2,500 square feet and features a spacious floor plan that flows seamlessly onto a generous lanai, providing the perfect...
Wailea Ekahi Village 8D - 1 Bedroom Garden View Condo
Wailea Ekahi 8D is an exquisite vacation rental located in the serene Wailea Ekahi Village. This spacious one-bedroom, two-bathroom condo is located on the second floor with vaulted ceilings and elevated views over the landscaped grounds below. Enjoy the large and open...
Walk to Waves, Pool, & Snorkeling - Wailea Ekahi 44B
For travelers seeking a budget-friendly option in the prestigious Wailea area without sacrificing comfort or location, Wailea Ekahi 44B presents an attractive choice. It is a charming studio provides a traveling couple or solo traveler everything they could need and...
Walk to Locals Favorite Beach - Wailea Ekahi 40F
Discover the charm of Maui from the comfort of Wailea Ekahi 40F, a beautifully appointed one-bedroom, one-bathroom condo located in the desirable Wailea community. This inviting vacation rental combines modern amenities with a touch of tropical elegance, offering a...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Grand Champion Villa Getaway - Wailea Beaches
Summary:🌴 Prime Location – Walk to beach, dining & shops🌅 Tranquil Balcony – Enjoy morning coffee w/ lush views 💤 Luxury Beds & Linens – Ultimate comfort for deep rest 🏊 Resort-Style Amenities – Pool, hot tub & tennis courts 🚗 Free Parking (1 spot) – Secure &...
Exquisite Prime Beachfront Haven, Indulge in Tropical Luxury -Wailea Elua 1302
Wailea Elua #1302 – Premier Beachfront One-Bedroom Escape in the Heart of WaileaWelcome to Wailea Elua #1302, a luxurious 1-bedroom, 1-bathroom beachfront condo offering comfort, serenity, and elevated island living just steps from Ulua Beach. Located within the...
Townhouse Retreat with Ocean Views From Upper & Lower Lanai - Wailea Ekahi #30B
Wailea Ekahi Village #30B Discover the perfect blend of luxury, comfort, and location at Wailea Ekahi Village #30B. This spacious two-story townhouse offers stunning ocean views from both floors, a fully remodeled kitchen and bathrooms (March 2025), and unbeatable...
Wailea Ekahi 52B | Resort Level Amenities!
With 34 acres of landscaped resort bordering one of Hawaii’s best beaches, Wailea Ekahi 52B is the ideal place to experience the very best of Hawaii. It’s affordable luxury that’s perfect for two couples wanting to share an island getaway. There’s a minimum stay...