Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-FiFrom $1,133/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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Map View · Page 14
Wailea Vacation Rentals Map
Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-FiFrom $1,133/night · Sleeps 6
Luxury Oceanview Wailea Retreat with Sunset ViewsFrom $598/night · Sleeps 10
Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical GroundsFrom $929/night · Sleeps 6
Wailea Oceanfront Center Front Row Luxury RetreatFrom $1,400/night · Sleeps 5
Lavish Premier Beachfront Townhouse W/ Unrivaled Views Wailea Elua 1305From $3,265/night · Sleeps 8
Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C - Palms at WaileaFrom $409/night · Sleeps 4
Wailea Ekolu 505 ~ Big Ocean Views ~ New FurnishingsFrom $430/night · Sleeps 6
Oceanview Serenity Meets Modern Comfort: Discover Wailea Ekolu #402From $486/night · Sleeps 4
Wailea Elua #2107 - Spacious, Stylish & Just Moments from Wailea BeachFrom $519/night · Sleeps 6
Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508From $1,256/night · Sleeps 6
Wailea Elua 1304 - Spectacular Oceanfront Condo with Panoramic ViewsFrom $1,729/night · Sleeps 4
Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of WaileaFrom $772/night · Sleeps 2
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, WifiFrom $426/night · Sleeps 8
Wailea Ekolu #708From $234/night · Sleeps 4
Wailea Ekolu Oceanview 2B/2B ocean view, ground floor unit, corner unitFrom $340/night · Sleeps 4
Wailea 1 BR Condo, close to everything, good pricingFrom $231/night · Sleeps 4
Beautiful 1 bedroom condo. Private ocean-view lanai overlooking fairway!From $179/night · Sleeps 4
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness CenterFrom $1,699/night · Sleeps 8
Escape to Paradise – Your Dream Wailea Getaway Awaits!From $239/night · Sleeps 6
Wailea Ekahi 51F Oceanview - Walk to BeachFrom $347/night · Sleeps 4
Family-friendly condo near Kihei and WaileaFrom $151/night · Sleeps 7
Poolside Wailea Condo, Walk to Keawakapu Beach, 4 Resort PoolsFrom $283/night · Sleeps 4
Wailea Ekahi 28C 2 Lanai's Ground Level, Ocean ViewFrom $440/night · Sleeps 4
Wailea Grand Champions #157 Great views, Free high speed Internet & Free parkingFrom $299/night · Sleeps 4
Outstanding Location in Maui South Kihei & WaileaFrom $295/night · Sleeps 4
Wailea Ekahi 45B-Great Rates,Lovely New Kitchen, Large Lanai, Pool #3 w/BBQFrom $435/night · Sleeps 4
Palms at Wailea 902 - Luxuriously Decorated, Spacious, and Very Private & QuietFrom $409/night · Sleeps 4
MauiJOY Villa ~ Expansive oceanview Retreat Above Wailea Pool Private locationFrom $825/night · Sleeps 6
Wailea Ekahi 1C - Wonderful 1bd/1ba / Close to the Beach / Sleeps 5From $305/night · Sleeps 5
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset ViewsFrom $395/night · Sleeps 6
Relaxing Wailea Ekahi Garden Hideaway.From $395/night · Sleeps 2
StunningReno*Palms in Wailea Condo-Beach*Golf*PoolFrom $292/night · Sleeps 6
Stunning Luxury Remodel I Wailea Beach Villas J206From $1,605/night · Sleeps 6
From $1,133/night
Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-Fi
Kihei, Hawaii
★★★★★ 10.0/10 · 6 reviews
Welcome to Wailea Elua 808, your ideal Maui retreat. This spacious 2-bedroom, 2-bath condo offers the perfect setting for a relaxing getaway or a...
From $598/night
Luxury Oceanview Wailea Retreat with Sunset Views
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 5 reviews
Escape to Hōkū Hale, a serene oceanview retreat in the heart of Wailea. This designer oasis offers modern comforts, a private lanai with stunning...
From $929/night
Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds
Wailea, Maui, Hawaii
★★★★★ 10.0/10 · 5 reviews
Wailea Elua #802 – Panoramic Oceanfront Luxury, Fully Remodeled in November 2024Welcome to Wailea Elua #802, a stunning second-floor oceanfront condo...
From $1,400/night
Wailea Oceanfront Center Front Row Luxury Retreat
Kihei, Hawaii
★★★★★ 10.0/10 · 5 reviews
Immerse yourself in the beauty of Maui at this stunning oceanfront property. This 2-bedroom, 2-bathroom condo offers center unit front row access of...
From $3,265/night
Lavish Premier Beachfront Townhouse W/ Unrivaled Views Wailea Elua 1305
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 5 reviews
Wailea Elua #1305 – Premier Oceanfront Townhouse for Elevated Maui LivingWelcome to Wailea Elua #1305, a luxury 3-bedroom, 3-bathroom oceanfront...
From $409/night
Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C - Palms at Wailea
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 3 reviews
The Palms at Wailea #2204 has been totally remodeled. This large condo of 1022 sq feet has soaring ceilings and stunning garden and ocean views from...
From $430/night
Wailea Ekolu 505 ~ Big Ocean Views ~ New Furnishings
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 3 reviews
Spectacular Ocean and Sunset Views!!A short walk or drive to Wailea’s best beaches.Newly furnished and well appointed home will provide an...
From $486/night
Oceanview Serenity Meets Modern Comfort: Discover Wailea Ekolu #402
Wailea, Maui, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Ekolu #402 – Your Serene Wailea EscapeEscape to paradise at Wailea Ekolu #402, where stunning ocean views, serene surroundings, and the spirit...
From $519/night
Wailea Elua #2107 - Spacious, Stylish & Just Moments from Wailea Beach
Wailea, Maui, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Elua #2107 – Your Serene Wailea EscapeWelcome to Wailea Elua Village, a peaceful, terraced beachfront property located in the heart of the...
From $1,256/night
Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508
Wailea, Maui, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Elua #1508 – Partial Ocean Views & Comfort Near PoolSet within the prestigious Wailea Elua Village, Wailea Elua #1508 offers an ideal balance...
From $1,729/night
Wailea Elua 1304 - Spectacular Oceanfront Condo with Panoramic Views
Wailea, Maui, Hawaii
★★★★★ 10.0/10 · 3 reviews
Wailea Elua #1304 – Oceanfront Comfort in the Heart of Wailea's Resort CommunityWelcome to Wailea Elua #1304, a beautifully appointed 2-bedroom,...
From $772/night
Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of Wailea
Kihei, Hawaii
★★★★★ 10.0/10 · 1 reviews
Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of WaileaWelcome to Wailea Elua 2007, a stunning 1-bedroom, 2-bath vacation retreat with...
From $426/night
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi
Kihei, Hawaii
★★★★★ 9.8/10 · 201 reviews
The Address to Wailea Ekolu #314: 10 Wailea Ekolu Pl. #314 Kihei HI 96753*Professionally Cleaned Condo, No-Contact Check-In/Check Out*Location &...
From $234/night
Wailea Ekolu #708
Wailea-Makena, Hawaii
★★★★★ 9.8/10 · 193 reviews
This Wailea Ekolu retreat goes hand in hand with your Maui experience. Here you will find a clean, open, beautiful condominium, with an amazing ocean...
From $340/night
Wailea Ekolu Oceanview 2B/2B ocean view, ground floor unit, corner unit
Kihei, Hawaii
★★★★★ 9.8/10 · 179 reviews
ENJOY THE BEAUTIFUL MAUI SUNSET! Sharon's spacious, 1,400 square foot Wailea Ekolu condominium is a two bedroom, two bath, ocean view unit. Located...
From $231/night
Wailea 1 BR Condo, close to everything, good pricing
Kihei, Hawaii
★★★★★ 9.8/10 · 170 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 $179/night
Beautiful 1 bedroom condo. Private ocean-view lanai overlooking fairway!
Wailea-Makena, Hawaii
★★★★★ 9.8/10 · 129 reviews
MAUI IS OPEN AND WELCOMING — Our legal short-term is calling - the island and people need your respectful tourism.After 25 years of visiting, we...
From $1,699/night
Newly Renovated Closest to Ho'olei Pool, Wailea Beach, the Grand, Fitness Center
Kihei, Hawaii
★★★★★ 9.8/10 · 114 reviews
One of a kind four bedroom Ho'olei home in Wailea!Breathtaking is the best word to describe this luxury townhouse-style villa at Ho’olei, situated in...
From $239/night
Escape to Paradise – Your Dream Wailea Getaway Awaits!
Kihei, Hawaii
★★★★★ 9.8/10 · 110 reviews
Welcome to your tropical retreat at Grand Champions Villas in Wailea, where luxury meets tranquility. Imagine unwinding in the hot tub while watching...
From $347/night
Wailea Ekahi 51F Oceanview - Walk to Beach
Kihei, Hawaii
★★★★★ 9.8/10 · 110 reviews
Our spacious Wailea Ekahi 1 bedroom, 2 bath condominium is fully appointed and includes phone, radio, high speed wi-fi internet connection, color TVs...
From $151/night
Family-friendly condo near Kihei and Wailea
Kihei, Hawaii
★★★★★ 9.8/10 · 107 reviews
Maui Vista 2413 is a spacious two-story, 2-bedroom, 2-bathroom condo offering comfortable amenities like air conditioning, a washer/dryer, and a...
From $283/night
Poolside Wailea Condo, Walk to Keawakapu Beach, 4 Resort Pools
Kihei, Hawaii
★★★★★ 9.8/10 · 107 reviews
Wailea Ekahi 42B | Poolside Paradise Steps from Keawakapu BeachWelcome to Wailea Ekahi 42B, your private tropical retreat in one of Maui's most...
From $440/night
Wailea Ekahi 28C 2 Lanai's Ground Level, Ocean View
Kihei, Hawaii
★★★★★ 9.8/10 · 107 reviews
GREAT LOCATION . WONDERFUL MORNING AND EVENING OCEAN VIEWS. LOCATED NEXT TO ONE OF THE 'QUIET' POOLS FOR AFTERNOON COOLING OFF. PLEASE NOTE :The...
From $299/night
Wailea Grand Champions #157 Great views, Free high speed Internet & Free parking
Kihei, Hawaii
★★★★★ 9.8/10 · 95 reviews
Why stay in Lahaina or Kihei when you can Vacation in a fabulous condominium on the sunny south coast of Maui. Located in the lush Wailea resort...
From $295/night
Outstanding Location in Maui South Kihei & Wailea
Kihei, Hawaii
★★★★★ 9.8/10 · 93 reviews
Aloha! Your dream vacation starts with our beautiful new condo, located in Southwest Maui, in the town of Kihei. The Maui Kamaole complex borders on...
From $435/night
Wailea Ekahi 45B-Great Rates,Lovely New Kitchen, Large Lanai, Pool #3 w/BBQ
Kihei, Hawaii
★★★★★ 9.8/10 · 91 reviews
Unit 45B is located in Building 45 on the ground floor. This lovely one bedroom, two bathroom condo has a 400 square foot lanai with picturesque...
From $409/night
Palms at Wailea 902 - Luxuriously Decorated, Spacious, and Very Private & Quiet
Kihei, Hawaii
★★★★★ 9.8/10 · 76 reviews
Hawaii Tax ID: TA-144-497-4592-01 QUIET PRIVACY IN PARADISE - BEAUTIFUL GARDEN/OCEAN VIEWSThe Palms #902 is a luxurious one-bedroom two-bath upstairs...
From $825/night
MauiJOY Villa ~ Expansive oceanview Retreat Above Wailea Pool Private location
Kihei, Hawaii
★★★★★ 9.8/10 · 76 reviews
The MauiJOY Villa – Private Oceanview Sanctuary in Maui MeadowsPerched above Wailea on a private half-acre in Maui Meadows, The MauiJOY Villa offers...
From $305/night
Wailea Ekahi 1C - Wonderful 1bd/1ba / Close to the Beach / Sleeps 5
Kihei, Hawaii
★★★★★ 9.8/10 · 75 reviews
Oceanfront complex, one-bedroom, one-bath, single-level, ground-floor corner unit.Quiet location. No traffic noise (you are in paradise, there should...
From $395/night
Sale!! Gorgeous 3BR 2BA Villa in Wailea, With Ocean and Sunset Views
Kihei, Hawaii
★★★★★ 9.8/10 · 63 reviews
Location, space, and unforgettable views define this rare three-bedroom Wailea villa.Nestled in the heart of one of Maui’s most prestigious resort...
From $395/night
Relaxing Wailea Ekahi Garden Hideaway.
Kihei, Hawaii
★★★★★ 9.8/10 · 61 reviews
Wailea Ekahi 47F is surrounded by lush gardens, offering guests a private hideaway to relax while being serenaded by birds. Our unit is a five minute...
From $292/night
StunningReno*Palms in Wailea Condo-Beach*Golf*Pool
Wailea-Makena, Hawaii
★★★★★ 9.8/10 · 52 reviews
CHECK ALL OF OUR MAUI PROPERTIES+THEIR CALENDARS -Scroll to the bottom “Meet your Host” then click on about Mandy and then scroll down to “all of...
From $1,605/night
Stunning Luxury Remodel I Wailea Beach Villas J206
Kihei, Hawaii
★★★★★ 9.8/10 · 46 reviews
Wailea Beach Villas is simply the best of the best! Enter the community through the 24hr private guarded gate & drive down to the complimentary self...