Ocean View Wailea 2bd I Wailea Ekolu 702From $534/night · Sleeps 7
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
Ocean View Wailea 2bd I Wailea Ekolu 702From $534/night · Sleeps 7
Remodeled Wailea 2BR/2BA | Haleakala & Golf Views | 2 Pools, Hot Tubs, AC | Walk to ShopsFrom $567/night · Sleeps 7
Incredibly roomy, adjacent to the best beaches/WaileaFrom $570/night · Sleeps 3
Ocean View w/AC - Wailea Elua 306From $632/night · Sleeps 4
The Grand Lanai Maui-60 foot Lanai directly on the Keawakapu beach Wailea/KiheiFrom $680/night · Sleeps 6
Refined Resort Wailea Oceanview VistasFrom $683/night · Sleeps 6
Wailea Ekolu 608 | Beautiful Wailea Condo with Ocean Views and Resort AmenitiesFrom $688/night · Sleeps 2
Wailea Ekolu 2 units- AC and Pool. Close to Sandy Beaches, Shopping, and DiningFrom $1,193/night · Sleeps 12
Wailea Ekolu | 4BR | Sleeps 12From $1,688/night · Sleeps 12
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802From $1,998/night · Sleeps 4
Castaway Cove Villa - Steps to Wailea Beach & PoolFrom $3,515/night · Sleeps 6
Romantic, Luxury, Sensual Retreat - Couples OnlyFrom $425/night · Sleeps 2
Ekahi 34F - Best Panoramic Ocean View!!From $600/night · Sleeps 6
Featured on A&E - Fully Renovated - A/C & Pool - Family FriendlyFrom $293/night · Sleeps 6
Owner Direct - 35% off in Oct & Nov!! - Elua Village 701, Luxury 2BR, Ocean ViewFrom $620/night · Sleeps 4
May Cancellation Discounts available. Island Retreat Spacious 3B 3B home.From $1,372/night · Sleeps 6
BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!From $383/night · Sleeps 2
Ocean View, Double Lanai and a Quick Walk to the BeachFrom $439/night · Sleeps 4
Wow!! What a Great View!!--GREAT REVIEWS!From $428/night · Sleeps 6
Designer - Best View!Ground Flr 2 Bdm/2Bth 39c! Remaining Spring Summer$400From $910/night · Sleeps 7
Best Location @ Ekahi... year round sunsets from lanai, stroll to the BeachFrom $678/night · Sleeps 6
Location Location! Ekahi 32C! Designer Remodel 2bdrm $400 Remaining SpringSummerFrom $400/night · Sleeps 6
Stunning Sea to Summit View - Spectacular Remodel Just CompletedFrom $781/night · Sleeps 4
Ekahi 8F, Oceanview Studio, extremely close to Beach and Main Pool! 2nd FloorFrom $475/night · Sleeps 2
Where Happiness Lives!From $539/night · Sleeps 6
Beautifully Studio Condo just steps to the Beach. Stunning Ocean Front Pool.From $295/night · Sleeps 2
Maui Retreat Ekahi 50F, All YOU Need! 5% off for stays over a week!From $370/night · Sleeps 4
Newly Renovation, All New: Beds, Furniture, Floors, Kitchen Counters and IslandFrom $1,199/night · Sleeps 10
Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront/Walk!From $1,039/night · Sleeps 4
Romantic, Luxury Condo with Spectacular Ocean ViewsFrom $415/night · Sleeps 2
Ekahi 4C - Quiet Garden View Close to Beach - 20% off Summer pricingFrom $490/night · Sleeps 4
Panoramic Ocean View Condo on Golf Course close to BeachesFrom $342/night · Sleeps 8
Romantic, Luxury Maui Getaway with Ocean View - Couples OnlyFrom $355/night · Sleeps 2
From $534/night
Ocean View Wailea 2bd I Wailea Ekolu 702
Kihei, Hawaii
Located in the heart of Wailea on the Wailea Blue Golf Course, this inviting upstairs ocean-view condo offers the perfect combination of island...
From $567/night
Remodeled Wailea 2BR/2BA | Haleakala & Golf Views | 2 Pools, Hot Tubs, AC | Walk to Shops
Kihei, Hawaii
Remodeled and Beautifully Updated Mountain View 2 Bedroom 2 Bathroom Condo at Grand Champions Wailea on the Golf Course - Grand Champions 30 Welcome...
From $570/night
Incredibly roomy, adjacent to the best beaches/Wailea
Kihei, Hawaii
Extremely roomy, high-end 1-bedroom 2-bathroom, deluxe 1039 square feet condo at the gateway to Wailea. Remodled and features a king bed, high-end...
From $632/night
Ocean View w/AC - Wailea Elua 306
Kihei, Hawaii
Book with us and come to Maui to explore everything we have to offer!Wailea Elua is a premier resort located on Ulua Beach in the heart of Wailea....
From $680/night
The Grand Lanai Maui-60 foot Lanai directly on the Keawakapu beach Wailea/Kihei
Kihei, Hawaii
Set within one of Maui's most coveted oceanfront properties, this exceptional two-bedroom, two-bathroom condo has been thoughtfully reimagined with...
From $683/night
Refined Resort Wailea Oceanview Vistas
Kihei, Hawaii
Summary:Perched overlooking Wailea on southern Maui, this wonderful two-bedroom condo is a dreamy escape into open airy luxury. With incredible ocean...
From $688/night
Wailea Ekolu 608 | Beautiful Wailea Condo with Ocean Views and Resort Amenities
Kihei, Hawaii
Experience the best of Wailea from this beautiful Wailea Ekolu property with panoramic Pacific Ocean views. Enjoy spectacular sunsets, seasonal...
From $1,193/night
Wailea Ekolu 2 units- AC and Pool. Close to Sandy Beaches, Shopping, and Dining
Kihei, Hawaii
Wailea Ekolu is a beautiful 148-unit condominium development nestled in the heart of Wailea on the Wailea Blue Golf Course and across the street from...
From $1,688/night
Wailea Ekolu | 4BR | Sleeps 12
Kihei, Hawaii
Summary:This reservation includes two separate condos in the same community.The condos have separate entrances; adjoining units are not...
From $1,998/night
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802
Wailea, Maui, Hawaii
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated...
From $3,515/night
Castaway Cove Villa - Steps to Wailea Beach & Pool
Kihei, Hawaii
Welcome to C201 Castaway Cove, a recently redecorated second-floor corner villa just steps from Wailea Beach. This elegant retreat showcases a fresh,...
From $425/night
Romantic, Luxury, Sensual Retreat - Couples Only
Kihei, Hawaii
★★★★★ 10.0/10 · 209 reviews
Welcome to The Palms at Wailea – Your Luxury Island Paradise Awaits! Experience Maui from our beautifully remodeled condo, Unit #1603, located in the...
From $600/night
Ekahi 34F - Best Panoramic Ocean View!!
Kihei, Hawaii
★★★★★ 10.0/10 · 204 reviews
Wailea Ekahi 34F in Ekahi Village - A modern vacation escape.Our fully renovated condo with spectacular views has everything you need for your...
From $293/night
Featured on A&E - Fully Renovated - A/C & Pool - Family Friendly
Kihei, Hawaii
★★★★★ 10.0/10 · 173 reviews
Modern Wailea Retreat | Family Friendly | Fully Renovated | Full A/C l PoolFeatured on A&E's Vacation Rental PotentialWelcome to Palms at Wailea...
From $620/night
Owner Direct - 35% off in Oct & Nov!! - Elua Village 701, Luxury 2BR, Ocean View
Kihei, Hawaii
★★★★★ 10.0/10 · 164 reviews
Aloha! We are Julie and Randy and welcome to our home! We want you to enjoy the fantastic ocean views and luxury of our 2-bedroom, 2-bathroom condo...
From $1,372/night
May Cancellation Discounts available. Island Retreat Spacious 3B 3B home.
Kihei, Hawaii
★★★★★ 10.0/10 · 149 reviews
Aloha and e komo mai (welcome) to Hale Alana, your oasis in Wailea, Maui. Please contact us for seasonal discounts and special rates!Step into Hale...
From $383/night
BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!
Kihei, Hawaii
★★★★★ 10.0/10 · 144 reviews
If you are looking for luxurious, yet affordable, accommodations in a premier location, you have found it. The Grand Champions Villas are located in...
From $439/night
Ocean View, Double Lanai and a Quick Walk to the Beach
Kihei, Hawaii
★★★★★ 10.0/10 · 134 reviews
Condo Details: **This is a NON-Smoking Unit AND a non-smoking property. All forms of smoking or vaping is prohibited in the units, lanais as well as...
From $428/night
Wow!! What a Great View!!--GREAT REVIEWS!
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 120 reviews
WOW !! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui condo.Sweeping ocean views...
From $910/night
Designer - Best View!Ground Flr 2 Bdm/2Bth 39c! Remaining Spring Summer$400
Kihei, Hawaii
★★★★★ 10.0/10 · 110 reviews
Note that the main pool will be closed August 10-October 15, 2026. The other three pools, beach pavilion kitchen, fitness centre, beach bathrooms,...
From $678/night
Best Location @ Ekahi... year round sunsets from lanai, stroll to the Beach
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 108 reviews
What you will love about 14C: * CDC cleaning guidelines implemented * laundry done off site in professional grade CDC protocol machines* “Touchless”...
From $400/night
Location Location! Ekahi 32C! Designer Remodel 2bdrm $400 Remaining SpringSummer
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 96 reviews
Note that the main pool will be closed August 10-October 15, 2026. The other three pools, beach pavilion kitchen, fitness centre, beach bathrooms,...
From $781/night
Stunning Sea to Summit View - Spectacular Remodel Just Completed
Kihei, Hawaii
★★★★★ 10.0/10 · 85 reviews
Wailea Ekahi Unit 41C is a beautiful vacation condominium in the prestigious area of Wailea, known as the ''sunny side'' of Maui.Full renovation...
From $475/night
Ekahi 8F, Oceanview Studio, extremely close to Beach and Main Pool! 2nd Floor
Kihei, Hawaii
★★★★★ 10.0/10 · 67 reviews
Escape to paradise with stunning ocean and green belt views from the lanai of this 2nd floor studio. 8F is a fully-furnished studio featuring...
From $539/night
Where Happiness Lives!
Kihei, Hawaii
★★★★★ 10.0/10 · 62 reviews
The Grand Champions Villas are nestled in a premier location of Wailea, Maui and provide the experience you would expect from a world-class resort....
From $295/night
Beautifully Studio Condo just steps to the Beach. Stunning Ocean Front Pool.
Kihei, Hawaii
★★★★★ 10.0/10 · 60 reviews
LOCATION, LOCATION, LOCATION- Our Studio Condo in Building 9 is just steps from the Ocean Front Pool, Pavilion and Ocean. With Sweeping Views of the...
From $370/night
Maui Retreat Ekahi 50F, All YOU Need! 5% off for stays over a week!
Wailea,Kihei, Hawaii
★★★★★ 10.0/10 · 43 reviews
Waiting for you to come and unwind. Just bring yourself, everything else is HERE! Towels, beach chairs, umbrella, boogie board, whatever you...
From $1,199/night
Newly Renovation, All New: Beds, Furniture, Floors, Kitchen Counters and Island
Kihei, Hawaii
★★★★★ 10.0/10 · 39 reviews
This elegantly remodeled and redecorated, modern vacation home resulted from the collaboration of sophisticated and tasteful owners, and a...
From $1,039/night
Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront/Walk!
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 34 reviews
(9/17/25) We just wrapped a full condo remodel of our oceanfront home and am bringing the unit back online!Elua 1310 is in the closest building to...
From $415/night
Romantic, Luxury Condo with Spectacular Ocean Views
Kihei, Hawaii
★★★★★ 10.0/10 · 27 reviews
1 BR, 2 BA condo. Close to beach, golf, tennis, restaurants, and shopping.Aloha. We are excited to be the owners of this very special condo. We have...
From $490/night
Ekahi 4C - Quiet Garden View Close to Beach - 20% off Summer pricing
Kihei, Hawaii
★★★★★ 10.0/10 · 26 reviews
1 Bedroom, 1 Bathroom, Sleeps 2-4Located in the lower village, unit 4C is a ground floor unit is backing on to a quiet ravine and surrounded by a...
From $342/night
Panoramic Ocean View Condo on Golf Course close to Beaches
Kihei, Hawaii
★★★★★ 10.0/10 · 23 reviews
Our townhouse in the Wailea Ekolu Place located on the Wailea Blue Golf Course. It has a spectacular view and large lanais to enjoy a panoramic views...
From $355/night
Romantic, Luxury Maui Getaway with Ocean View - Couples Only
Kihei, Hawaii
★★★★★ 10.0/10 · 22 reviews
Welcome to The Palms at Wailea – Your Island Paradise Awaits!Nestled in the prestigious Wailea resort community, The Palms at Wailea condo complex is...