Fantastic ALL NEWLY DECORATED Wailea condoFrom $357/night · Sleeps 3
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
Fantastic ALL NEWLY DECORATED Wailea condoFrom $357/night · Sleeps 3
Spectacular Oceanfront Views with Split AC -WaileaFrom $340/night · Sleeps 4
Palms at Wailea 705 - Luxury Renovation, Prime Location, Close to Shops, Full ACFrom $476/night · Sleeps 6
Summer Deal Wailea 2BR Condo with Lanai Pool and Jacuzzi AccessFrom $539/night · Sleeps 6
Gorgeous Remodel! Two King Suites & Huge Ocean Views! Close To Wailea BeachesFrom $289/night · Sleeps 6
GC 163 Spacious Wailea 2BD w AC Pool Close to BeachFrom $231/night · Sleeps 7
Tropical garden view Wailea condoFrom $153/night · Sleeps 6
Beautiful - Palms at Wailea 1802From $347/night · Sleeps 6
Unbeatable Ocean Vistas at Polo Beach Club #606 – Beachfront Living in WaileaFrom $1,274/night · Sleeps 6
NEW - Wailea Getaway - steps to great pool & beachFrom $828/night · Sleeps 6
Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142From $189/night · Sleeps 4
Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!From $439/night · Sleeps 6
Spacious Condo Near Kihei and Wailea Beaches - Kam III and Keawakapu Beach.From $298/night · Sleeps 6
Stylish Wailea Condo Near Beach, Dining & Resort PoolFrom $303/night · Sleeps 6
Wailea Ekolu 403, Prime Location, Stunning Ocean Views, Spacious Lanai, Split ACFrom $479/night · Sleeps 6
Garden View Wailea Condo Near Keawakapu Beach & DiningFrom $331/night · Sleeps 8
Great Wailea studio CondoFrom $167/night · Sleeps 4
Ocean View, Air Conditioned, 2 level Wailea TownhouseFrom $360/night · Sleeps 8
Steps to Keawakapu Beach - 4 Pools - Private Lanai - Wailea Ekahi 44AFrom $283/night · Sleeps 4
Palms at Wailea - Fully Air ConditionedFrom $312/night · Sleeps 5
Sunny Top Floor Condo, 10 minute walk from Wailea beachesFrom $145/night · Sleeps 4
Palms at Wailea 901 - Luxuriously Decorated Spacious Unit w/ Large Private LanaiFrom $400/night · Sleeps 4
Wailea Jewel; near Beaches; SHOPS/5 Star Hotels; Convenient!From $315/night · Sleeps 5
Oceanfront Wailea condo with hot tubs, resort pools summer dealsFrom $1,000/night · Sleeps 6
Wailea Serenity | 2 Bed, 2 BathFrom $471/night · Sleeps 6
Gorgeous Expansive Condo in Wailea with HUGE Lanai & Ocean ViewsFrom $350/night · Sleeps 6
Spacious Wailea Condo with Resort Pool & Private LanaiFrom $458/night · Sleeps 4
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview CondoFrom $1,418/night · Sleeps 6
Beachfront, Ocean View, Polo Beach Wailea/Makena #306From $1,511/night · Sleeps 6
Beautifully remodeled ocean view condo in Wailea WE27BFrom $640/night · Sleeps 6
Gorgeous Updated Wailea Condo Walking Distance to Beaches & Near Golf CoursesFrom $423/night · Sleeps 6
New Listing! Palms at Wailea 1501! Ground floor with Ocean views!From $447/night · Sleeps 4
Where Kihei Meets Wailea Remodeled Condo Panoramic Ocean Views Pool BeachFrom $762/night · Sleeps 6
From $357/night
Fantastic ALL NEWLY DECORATED Wailea condo
Kihei, Hawaii
★★★★★ 9.6/10 · 41 reviews
WELCOME to The Palms at Wailea, Unit 202 - your home away from home! This unit has been completely refurbished and newly decorated. The 2nd floor...
From $340/night
Spectacular Oceanfront Views with Split AC -Wailea
Kihei, Hawaii
★★★★★ 9.6/10 · 40 reviews
Kihei Surfside #507 features Incredible views from the lanai, kitchen, dining, and living areas. Completely renovated featuring porcelain tile...
From $476/night
Palms at Wailea 705 - Luxury Renovation, Prime Location, Close to Shops, Full AC
Kihei, Hawaii
★★★★★ 9.6/10 · 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 $539/night
Summer Deal Wailea 2BR Condo with Lanai Pool and Jacuzzi Access
Wailea-Makena, Hawaii
★★★★★ 9.6/10 · 38 reviews
Fabulous value in Wailea Resort! If you want the perfect and spacious 2-bed/2-bath condo that is tastefully decorated, offers complete privacy and...
From $289/night
Gorgeous Remodel! Two King Suites & Huge Ocean Views! Close To Wailea Beaches
Kihei, Hawaii
★★★★★ 9.6/10 · 37 reviews
Come experience the panoramic ocean views from the lanai of this tastefully remodeled gem located in highly desirable Wailea Ekolu. Natural lighting,...
From $231/night
GC 163 Spacious Wailea 2BD w AC Pool Close to Beach
Kihei, Hawaii
★★★★★ 9.6/10 · 27 reviews
Spacious 2Bedroom, 2Bathroom Luxurious Wailea Condo. Ideal Location to Walk to Beach, Tennis, Golf, Fine Dining, Luxury Shopping, and so much more. -...
From $153/night
Tropical garden view Wailea condo
Kihei, Hawaii
★★★★★ 9.6/10 · 24 reviews
Grand Champions 8 is a 2 bedroom, 2 bathroom condo featuring amenities such as a private lanai, air-conditioning and a washer/dryer. Located on the...
From $347/night
Beautiful - Palms at Wailea 1802
Kihei, Hawaii
★★★★★ 9.6/10 · 19 reviews
Located in the Kihei/Wailea area, in the world-famous Wailea Resort community, The Palms at Wailea complex boasts a beautiful pool, hot tub and is...
From $1,274/night
Unbeatable Ocean Vistas at Polo Beach Club #606 – Beachfront Living in Wailea
Makena, Maui, Hawaii
★★★★★ 9.6/10 · 17 reviews
Polo Beach #606Welcome to Polo Beach #606, an elegant top-floor oceanfront condo at the sought-after Polo Beach Club in Wailea. With breathtaking...
From $828/night
NEW - Wailea Getaway - steps to great pool & beach
Kihei, Hawaii
★★★★★ 9.6/10 · 14 reviews
Summary:Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private...
From $189/night
Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142
Wailea, Maui, Hawaii
★★★★★ 9.6/10 · 12 reviews
Wailea Grand Champions #142- Garden View Comfort in the Heart of WaileaWelcome to Wailea Grand Champions #142, a beautifully maintained one-bedroom,...
From $439/night
Wailea Ekolu 206 -Gorgeous Ocean View - AC - Close to Wailea Beach!
Kihei, Hawaii
★★★★★ 9.6/10 · 10 reviews
E Komo Mai to our luxury 2 bedroom unit on the 2nd floor with a beautiful ocean view and a spacious interior. From our comfortable lanai seating you...
From $298/night
Spacious Condo Near Kihei and Wailea Beaches - Kam III and Keawakapu Beach.
Kihei, Hawaii
★★★★★ 9.6/10 · 9 reviews
Come enjoy this tranquil unit with modern updated furnishings and two great lanais. Unit 59 has 2 bedrooms and 2 bathrooms with plenty of room inside...
From $303/night
Stylish Wailea Condo Near Beach, Dining & Resort Pool
Kihei, Hawaii
★★★★★ 9.6/10 · 9 reviews
Experience paradise in this newly remodeled 2-bedroom, 2-bathroom condo at Palms at Wailea, 2303. Nestled in a private corner of the property, this...
From $479/night
Wailea Ekolu 403, Prime Location, Stunning Ocean Views, Spacious Lanai, Split AC
Kihei, Hawaii
★★★★★ 9.6/10 · 8 reviews
Welcome to Wailea Ekolu 403, a stunning Maui vacation rental offering breathtaking ocean views, luxurious comfort, and a prime location in the heart...
From $331/night
Garden View Wailea Condo Near Keawakapu Beach & Dining
Kihei, Hawaii
★★★★★ 9.6/10 · 6 reviews
Experience elevated island living in this exquisitely remodeled 2-bedroom, 2-bathroom residence at the prestigious Palms at Wailea, where refined...
From $167/night
Great Wailea studio Condo
Kihei, Hawaii
★★★★★ 9.4/10 · 159 reviews
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully...
From $360/night
Ocean View, Air Conditioned, 2 level Wailea Townhouse
Kihei, Hawaii
★★★★★ 9.4/10 · 137 reviews
Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi Internet connection. Three flat...
From $283/night
Steps to Keawakapu Beach - 4 Pools - Private Lanai - Wailea Ekahi 44A
Kihei, Hawaii
★★★★★ 9.4/10 · 116 reviews
Wailea Ekahi 44A | Keawakapu Beach • Private Lanai • Wailea CondoWailea Ekahi • Keawakapu Beach • Ocean View Condo • Walk to Beach • Free Parking •...
From $312/night
Palms at Wailea - Fully Air Conditioned
Kihei, Hawaii
★★★★★ 9.4/10 · 95 reviews
Welcome to our Wailea Condo at the Palms of Wailea. Our condo is a large 1200 square foot newly renovated two bedroom, two bathroom condo that is...
From $145/night
Sunny Top Floor Condo, 10 minute walk from Wailea beaches
Wailea-Makena, Hawaii
★★★★★ 9.4/10 · 93 reviews
This spacious, quiet, bright second floor condo has high vaulted ceilings and a large living/dining area that creates a large, bright, and airy feel....
From $400/night
Palms at Wailea 901 - Luxuriously Decorated Spacious Unit w/ Large Private Lanai
Kihei, Hawaii
★★★★★ 9.4/10 · 66 reviews
Hawaii Tax ID: TA-144-497-4592-01 QUIET PRIVACY IN PARADISE The Palms #901 is a luxurious one-bedroom two-bath ground floor villa tucked away in a...
From $315/night
Wailea Jewel; near Beaches; SHOPS/5 Star Hotels; Convenient!
Kihei, Hawaii
★★★★★ 9.4/10 · 51 reviews
ALOHA and welcome to our unit in Wailea Ekolu, A two bedroom, two bath condominium on the ground floor. Our condo is located in the beautiful, lush,...
From $1,000/night
Oceanfront Wailea condo with hot tubs, resort pools summer deals
Kihei, Hawaii
★★★★★ 9.4/10 · 51 reviews
Makena Surf is an exclusive oceanfront property in World Famous Wailea-Makena! One of the best-kept secrets on South Maui, from its stunning beauty...
From $471/night
Wailea Serenity | 2 Bed, 2 Bath
Kihei, Hawaii
★★★★★ 9.4/10 · 49 reviews
Summary:Wailea Serenity - 2BD - Private, Quiet; the tropical paradise you dreamed about!The Space:This Grand Champions condo (#15 in building #2) is...
From $350/night
Gorgeous Expansive Condo in Wailea with HUGE Lanai & Ocean Views
Kihei, Hawaii
★★★★★ 9.4/10 · 47 reviews
Address for this Condo: Wailea Ekahi, 3300 Wailea Alanui Dr. (Unit 51A), Kihei HI 96753***Professionally Cleaned Condo, No-Contact Check-In/Check...
From $458/night
Spacious Wailea Condo with Resort Pool & Private Lanai
Kihei, Hawaii
★★★★★ 9.4/10 · 43 reviews
#2104 is a spacious and recently refreshed 2-bedroom, 2-bathroom condo in Maui with fun tropical accents and cozy comfort. It offers approximately...
From $1,418/night
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Wailea-Makena, Hawaii
★★★★★ 9.4/10 · 29 reviews
Features of our 2300 sq oceanview condo include: Two full master suites Second bedroom can have two twins or king sized bedA den that closes off...
From $1,511/night
Beachfront, Ocean View, Polo Beach Wailea/Makena #306
Kihei, Hawaii
★★★★★ 9.4/10 · 29 reviews
Unit 306 is a 2 bedroom and 2 bath condo located on the third floor at the Polo Beach Club. The Polo Beach condo's sleep 6. Please call for very...
From $640/night
Beautifully remodeled ocean view condo in Wailea WE27B
Kihei, Hawaii
★★★★★ 9.4/10 · 23 reviews
Hawaii Tax ID: TA-072-016-4864-01TMK: 210080600050Discover your tropical oasis at Wailea Ekahi 27B, situated in the prestigious Wailea area of Maui....
From $423/night
Gorgeous Updated Wailea Condo Walking Distance to Beaches & Near Golf Courses
Kihei, Hawaii
★★★★★ 9.4/10 · 14 reviews
Address for this Condo: Palms at Wailea 3200 Wailea Alanui Dr. (Unit 2105)Wailea, HI 96753*** Professionally Cleaned Condo, No Contact Check-In/Check...
From $447/night
New Listing! Palms at Wailea 1501! Ground floor with Ocean views!
Kihei, Hawaii
★★★★★ 9.4/10 · 11 reviews
Welcome to our magnificent Oceanview retreat, nestled within the highly coveted Palms at Wailea. This nicely updated ground floor 1-bedroom, 2-bath...
From $762/night
Where Kihei Meets Wailea Remodeled Condo Panoramic Ocean Views Pool Beach
Kihei, Hawaii
★★★★★ 9.4/10 · 10 reviews
Step inside this newly remodeled tropical oasis, where panoramic ocean views greet you from the open concept living room, primary bedroom, lanai, and...