Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!From $264/night · Sleeps 2
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
Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!From $264/night · Sleeps 2
Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full BathFrom $692/night · Sleeps 4
Stunning One Bedroom in the Heart of Wailea Ekahi Village Unit 28BFrom $383/night · Sleeps 4
Spacious Wailea Townhouse + Ocean Views! Ekahi 48AFrom $649/night · Sleeps 6
Maui Designer Beach Villa, Wailea, Ho'olei 39-2From $1,599/night · Sleeps 10
Panoramic Ocean View Wailea Ekahi 34D Summer Special 325/nightFrom $383/night · Sleeps 2
Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-FiFrom $1,009/night · Sleeps 4
Ocean Views & Modern Aloha Luxury in Heart of WaileaFrom $564/night · Sleeps 4
New Listing, Wailea Ekahi Village 5F, Close to Oceanfront Pool Pavilion on Keawakapu BeachFrom $566/night · Sleeps 6
Wailea Elua 805 - 3-Bedroom Ocean View Luxury Condo in the Heart of Wailea, MauiFrom $663/night · Sleeps 6
Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,From $399/night · Sleeps 6
Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-FiFrom $1,085/night · Sleeps 6
Wailea Ekahi Gem! Updated Large 1BR+sleeper, Close to Beach & Pools, XL LanaiFrom $391/night · Sleeps 4
Summer Deal Beachfront Wailea Villa with Pool Hot Tub and Ocean ViewsFrom $1,112/night · Sleeps 6
Spectacular Ocean View & All-Season Sunsets from Private Lanai Wailea Ekolu 1704From $272/night · Sleeps 2
Captivating Ocean View Retreat: Spacious Beauty at Wailea Elua #902From $999/night · Sleeps 5
Luxurious & Spacious Ground Floor Gem with Panoramic Oceanview - Wailea Elua 305From $1,133/night · Sleeps 4
Wailea Elua 2003 - Ground Level Gem -Oceanfront Property W/ Tropical GroundsFrom $826/night · Sleeps 4
Beautiful Condo, Private Lanai, Near Wailea BeachesFrom $199/night · Sleeps 6
Luxurious 1 BR, 2 BA Wailea- Remodeled Bathrooms.From $392/night · Sleeps 4
Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf ViewsFrom $420/night · Sleeps 4
Wailea Ekolu 510 - Ocean Views, Private Lanais, Renovated 2-Story with Split AC!From $720/night · Sleeps 6
Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectacular ViewFrom $585/night · Sleeps 4
Wailea Grand Champions 168 - Amazing Golf Course & Ocean ViewsFrom $352/night · Sleeps 4
Wailea, Sleeps 6, A/C, Priv. Tennis/Pickleball Court, Steps from Keawakapu BeachFrom $700/night · Sleeps 6
Relaxing Wailea Condo with Lanai, Pool & Island CharmFrom $186/night · Sleeps 6
Wailea Ekahi 33A 1bd/2bth, luxury, remodel, 3 min walk to beach, many amenitiesFrom $460/night · Sleeps 4
Wailea Elua 1401 - Beautiful Ground Floor 1BR Oceanfront Unit on Ulua BeachFrom $725/night · Sleeps 2
Comfortable Personalized Unit in Beautiful Wailea Ekahi!From $375/night · Sleeps 4
Wailea Beach Condo W/ Ocean Views!! NEW RatesFrom $704/night · Sleeps 8
Wailea Ekahi Village 27C - Poolside, Steps to the Beach, Sweeping Ocean Views!From $365/night · Sleeps 4
Summer Deal Wailea Ocean View 2BR Condo with Golf Course AccessFrom $321/night · Sleeps 5
Palms at Wailea 703 - Modern Renovation, Prime Location, Full AC, Close to Pool!From $430/night · Sleeps 6
From $264/night
Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!
Kihei, Hawaii
★★★★★ 9.8/10 · 44 reviews
* * * * The Wailea Ekahi main pool area will be closed for renovations from August 10, 2026 to October 15, 2026. The 3 other pools on property will...
From $692/night
Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full Bath
Kihei, Hawaii
★★★★★ 9.8/10 · 40 reviews
Welcome to Unit 42A at Wailea Ekahi Villas right in the heart of the Wailea Resort District and next door to the famous ocean front Andaz Hotel. This...
From $383/night
Stunning One Bedroom in the Heart of Wailea Ekahi Village Unit 28B
Kihei, Hawaii
★★★★★ 9.8/10 · 36 reviews
Listen to the waves calmly lap against the shore as you drink your coffee on your own private lanai. Enjoy cooking your favorite meal in a newly...
From $649/night
Spacious Wailea Townhouse + Ocean Views! Ekahi 48A
Kihei, Hawaii
★★★★★ 9.8/10 · 35 reviews
Welcome to Wailea Ekahi 48A, offering the largest floor plan with gorgeous ocean view! This beautiful 2 bedroom/2.5 bath is the perfect retreat for...
From $1,599/night
Maui Designer Beach Villa, Wailea, Ho'olei 39-2
Kihei, Hawaii
★★★★★ 9.8/10 · 35 reviews
Welcome to Your Pristine OasisIndulge in the lap of luxury at this exquisite 3,464-square-foot vacation rental villa (Ho'olei, Maile floor plan)....
From $383/night
Panoramic Ocean View Wailea Ekahi 34D Summer Special 325/night
Kihei, Hawaii
★★★★★ 9.8/10 · 34 reviews
Wailea Ekahi 34D is located in the lower village, on the greenbelt, with direct views of the ocean, Molokini and Kaho'olawa. This condo has been...
From $1,009/night
Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-Fi
Kihei, Hawaii
★★★★★ 9.8/10 · 33 reviews
Wailea Elua 1201 is perfectly positioned in the coveted interior courtyard, 39 steps to famous Ulua Beach, perennially named as one of the world's...
From $564/night
Ocean Views & Modern Aloha Luxury in Heart of Wailea
Kihei, Hawaii
★★★★★ 9.8/10 · 30 reviews
Welcome to our Ohana. The Hawaiian word "Ohana" means family and embodies the spiritual quality of kindness and love for all of the human family. Our...
From $566/night
New Listing, Wailea Ekahi Village 5F, Close to Oceanfront Pool Pavilion on Keawakapu Beach
Kihei, Hawaii
★★★★★ 9.8/10 · 29 reviews
Summary:Ocean Breezes & Maui Magic: Wailea Ekahi Village Unit 5FThe Space:Maintenance Notice: Our beach front pool will be closed from Monday, August...
From $663/night
Wailea Elua 805 - 3-Bedroom Ocean View Luxury Condo in the Heart of Wailea, Maui
Kihei, Hawaii
★★★★★ 9.8/10 · 27 reviews
Welcome to Wailea Elua 805, a beautifully remodeled 3-bedroom, 2-bathroom vacation rental located in the exclusive, gated beachfront community of...
From $399/night
Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,
Kihei, Hawaii
★★★★★ 9.8/10 · 26 reviews
The fabulous Keawakapu Beach is just a short 10 min stroll. The Palms at Wailea is a gorgeous property with a large pool and hot tub. A magnificent...
From $1,085/night
Wailea Elua 702 - Beautifully Renovated, Stunning Ocean Views, Central AC, Wi-Fi
Kihei, Hawaii
★★★★★ 9.8/10 · 26 reviews
Welcome to Wailea Elua Village 702, a beautifully remodeled two-bedroom, two-bath ocean-view vacation rental in the heart of Wailea, Maui. Spacious,...
From $391/night
Wailea Ekahi Gem! Updated Large 1BR+sleeper, Close to Beach & Pools, XL Lanai
Kihei, Hawaii
★★★★★ 9.8/10 · 25 reviews
Experience Maui paradise at Wailea Ekahi 21B, an updated ground-floor one-bedroom/two-bath vacation condo nestled within the prestigious Wailea...
From $1,112/night
Summer Deal Beachfront Wailea Villa with Pool Hot Tub and Ocean Views
Kihei, Hawaii
★★★★★ 9.8/10 · 23 reviews
This property is hotel zoned, and not being affected by the recent proposed legislation.The Best Villa Experience at Ho'olei in Maui awaits you at...
From $272/night
Spectacular Ocean View & All-Season Sunsets from Private Lanai Wailea Ekolu 1704
Kihei, Hawaii
★★★★★ 9.8/10 · 22 reviews
Aloha,Welcome to our family gem, location Wailea Ekolu Unit 1704. Our 1070 square foot spacious condo with private lanais, has been a family treasure...
From $999/night
Captivating Ocean View Retreat: Spacious Beauty at Wailea Elua #902
Wailea, Maui, Hawaii
★★★★★ 9.8/10 · 16 reviews
Wailea Elua #902 – Newly Remodeled Ocean View Escape with Upscale Island StyleWelcome to Wailea Elua #902, a beautifully updated second-floor,...
From $1,133/night
Luxurious & Spacious Ground Floor Gem with Panoramic Oceanview - Wailea Elua 305
Wailea, Maui, Hawaii
★★★★★ 9.8/10 · 13 reviews
Wailea Elua #305 – Stunning Ocean View Retreat with Luxury Comforts and Designer FinishesExperience the elegance and serenity of Wailea Elua #305, a...
From $826/night
Wailea Elua 2003 - Ground Level Gem -Oceanfront Property W/ Tropical Grounds
Wailea, Maui, Hawaii
★★★★★ 9.8/10 · 8 reviews
Wailea Elua #2003 – Elegant Ocean View Living with Ground Floor ConvenienceDiscover serene oceanview living at Wailea Elua #2003, a beautifully...
From $199/night
Beautiful Condo, Private Lanai, Near Wailea Beaches
Kihei, Hawaii
★★★★★ 9.6/10 · 175 reviews
Address for this Condo: Grand Champions, 155 Wailea Ike Pl #5, Kihei HI 96753***Professionally Cleaned Condo, No-contact Check-In/Check Out***...
From $392/night
Luxurious 1 BR, 2 BA Wailea- Remodeled Bathrooms.
Kihei, Hawaii
★★★★★ 9.6/10 · 143 reviews
Our villa is a one bedroom, 2 bathroom on the ground floor with a very large lanai, which features sliding doors that expand the living room into the...
From $420/night
Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf Views
Kihei, Hawaii
★★★★★ 9.6/10 · 101 reviews
Hawaii Tax ID: TA-144-497-4592-01 FRONT-ROW UNIT - STUNNING OCEAN & GOLF COURSE VIEWSWailea Ekolu #304 is a luxurious condominium situated at the...
From $720/night
Wailea Ekolu 510 - Ocean Views, Private Lanais, Renovated 2-Story with Split AC!
Kihei, Hawaii
★★★★★ 9.6/10 · 97 reviews
This extra-spacious two-story town-home-styled condo has no common walls and no one above, with a premiere location at Wailea Ekolu unit 510. Enjoy...
From $585/night
Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectacular View
Wailea-Makena, Hawaii
★★★★★ 9.6/10 · 95 reviews
Polo Beach Club #406 is a beautiful, comfortable oceanfront condo with breathtaking views of Molokini, West Maui, Kahoolawe, and Lanai. The...
From $352/night
Wailea Grand Champions 168 - Amazing Golf Course & Ocean Views
Kihei, Hawaii
★★★★★ 9.6/10 · 90 reviews
Hawaii Tax ID: TA-144-497-4592-01AMAZING GOLF COURSE & OCEAN VIEWSGrand Champions #168 is a one-bedroom two-bath luxury villa with amazing golf...
From $700/night
Wailea, Sleeps 6, A/C, Priv. Tennis/Pickleball Court, Steps from Keawakapu Beach
Kihei, Hawaii
★★★★★ 9.6/10 · 82 reviews
Pardon our absence but we are remodeling the house. We should be done by November 2026. Steps from Keawakapu Beach, a 3 bedroom, 2 bath, spacious and...
From $186/night
Relaxing Wailea Condo with Lanai, Pool & Island Charm
Kihei, Hawaii
★★★★★ 9.6/10 · 79 reviews
You're sure to have a fabulous stay! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this...
From $460/night
Wailea Ekahi 33A 1bd/2bth, luxury, remodel, 3 min walk to beach, many amenities
Wailea, Maui, Hawaii
★★★★★ 9.6/10 · 78 reviews
Wailea Ekahi 33A is a beautiful, romantic, family friendly, 1,100 square-foot 1 bedroom, 2 bath condo in a magnificent, lush tropical paradise resort...
From $725/night
Wailea Elua 1401 - Beautiful Ground Floor 1BR Oceanfront Unit on Ulua Beach
Kihei, Hawaii
★★★★★ 9.6/10 · 66 reviews
Welcome to Wailea Elua Village, a premier gated community nestled in the heart of Wailea. Our ground-floor beachfront condominium (#1401) offers the...
From $375/night
Comfortable Personalized Unit in Beautiful Wailea Ekahi!
Wailea-Makena, Hawaii
★★★★★ 9.6/10 · 64 reviews
Welcome to Paradise - This is a beautifully appointed ground floor, one bedroom, two bathroom vacation condominium, located in gorgeous Wailea Ekahi....
From $704/night
Wailea Beach Condo W/ Ocean Views!! NEW Rates
Kihei, Hawaii
★★★★★ 9.6/10 · 62 reviews
NEWLY REMODELED BEACH CHIC CONDO with ocean views, in the heart of Wailea. Our Wailea condo offers 2 bedrooms, and 2½ bathrooms, with over 1500...
From $365/night
Wailea Ekahi Village 27C - Poolside, Steps to the Beach, Sweeping Ocean Views!
Kihei, Hawaii
★★★★★ 9.6/10 · 55 reviews
*****UPDATE: New, mini-split air conditioning system installed in August, 2025*****Ekahi Village 27C is a beautifully-decorated, updated and...
From $321/night
Summer Deal Wailea Ocean View 2BR Condo with Golf Course Access
Kihei, Hawaii
★★★★★ 9.6/10 · 54 reviews
Marvel at the picturesque views from this premier Hawaiian retreat of Grand Champions 35. Located in the heart of Wailea with a country club feel and...
From $430/night
Palms at Wailea 703 - Modern Renovation, Prime Location, Full AC, Close to Pool!
Kihei, Hawaii
★★★★★ 9.6/10 · 53 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...