Polo Beach 106! Steps from the Beach! Amazing Views! Favorite Location!From $964/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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Wailea Vacation Rentals Map
Polo Beach 106! Steps from the Beach! Amazing Views! Favorite Location!From $964/night · Sleeps 6
Whale Watch From Your Lanai - Makena Surf E302From $1,468/night · Sleeps 4
Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!From $1,150/night · Sleeps 6
3BD Oceanfront - Great for Families | Makena Surf F112From $1,348/night · Sleeps 7
Wrap-Around Ocean Views | Wailea Beach Villas PH301From $2,793/night · Sleeps 8
Beachfront Condo – Location, Location, LocationFrom $1,058/night · Sleeps 6
Cool Wailea Villa with Arcade MachineFrom $2,001/night · Sleeps 6
Fairway + Pacific Ocean Views | Wailea Ekolu 910From $245/night · Sleeps 6
Recently Renovated - Walk to the BeachFrom $1,235/night · Sleeps 4
Beachfront Condo - Steps from Wailea Beach PathFrom $1,394/night · Sleeps 6
Makena Surf E103 | Ground-Floor Oceanfront Front-Row with Direct Beach AccessFrom $1,620/night · Sleeps 5
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large LanaiFrom $650/night · Sleeps 4
Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&PoolFrom $300/night · Sleeps 4
Wailea Luxury on a Budget at Grand Champion Villas - 2 Bd+2 BathFrom $355/night · Sleeps 6
360 Ocean Views + Full Remodel! Top Floor # 904!From $461/night · Sleeps 2
Palms At Wailea 2002- RARE FIND - Multi Level townhouse in Wailea!From $575/night · Sleeps 8
1A Newly renovated w/porcelain tile floors, custom cabinets, granite countertopsFrom $466/night · Sleeps 4
Oceanfront Maui condo w/ lanai and island viewsFrom $1,309/night · Sleeps 6
Ocean and fairway views in this spacious, top-floor, 3-BR Grand Champion Villa!From $245/night · Sleeps 6
Wailea Ekahi 31B, 1 BR/2BA, Lower Greenbelt, Ocean ViewFrom $370/night · Sleeps 4
Ho'olei Two-Story Townhome with Gourmet Kitchen and Resort AmenitiesFrom $1,404/night · Sleeps 8
Fantastic Wailea Ekahi Beachfront Condo 45FFrom $311/night · Sleeps 5
Beautiful Wailea Retreat with Pool, Lanai & Beach AccessFrom $368/night · Sleeps 6
*Stroll To The Beach Til Toes In The Sand!*Beautiful Views*Ground Floor*4 Pools*From $705/night · Sleeps 6
Beachfront Wailea condo w/ ocean views and lanaiFrom $1,369/night · Sleeps 6
Steps to Ulua Beach-Wailea Elua 3-Bdr/3-Bath Beachfront Townhouse #1004From $1,980/night · Sleeps 6
Heart of Wailea, Remodeled Kitchen + AC! Ekahi 45AFrom $395/night · Sleeps 4
Elua Village Contemporary 2bd+2ba OceanviewFrom $753/night · Sleeps 6
Wailea Condo Near Keawakapu Beach with Pool & Tropical SettingFrom $566/night · Sleeps 6
Peaceful Wailea Condo Near Keawakapu Beach & Resort PoolFrom $146/night · Sleeps 4
Wailea Elua Village Fresh and Contemporary 2Bdr+2 Bath Oceanview CondominiumFrom $791/night · Sleeps 6
Spacious Wailea Maui Condo with Pool & Tropical Garden SettingFrom $254/night · Sleeps 4
5th Floor Elevated Ocean Views | Polo Beach Club 508From $1,144/night · Sleeps 6
From $964/night
Polo Beach 106! Steps from the Beach! Amazing Views! Favorite Location!
Wailea, Hawaii
★★★★★ 9.8/10 · 17 reviews
Experience true beachfront living at Polo Beach Club 106, a rare ground-floor oceanfront condo in Wailea with direct beach access and panoramic...
From $1,468/night
Whale Watch From Your Lanai - Makena Surf E302
Wailea, Hawaii
★★★★★ 9.8/10 · 17 reviews
Welcome to Makena Surf E302, an exquisite ocean view vacation condo that perfectly blends antique charm with modern luxury. Spanning 1,038 sq. ft.,...
From $1,150/night
Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!
Wailea, Hawaii
★★★★★ 9.8/10 · 12 reviews
Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining areas, Wailea Elua 2204 is a...
From $1,348/night
3BD Oceanfront - Great for Families | Makena Surf F112
Wailea, Hawaii
★★★★★ 9.8/10 · 11 reviews
Makena Surf F112 is a stunning oceanfront vacation home that offers unparalleled views of the sea from both the spacious living area and the...
From $2,793/night
Wrap-Around Ocean Views | Wailea Beach Villas PH301
Wailea, Hawaii
★★★★★ 9.8/10 · 11 reviews
Wailea Beach Villas Penthouse 301 offers an unparalleled vacation experience with its luxurious 2,500 square foot ocean view suite. Situated on the...
From $1,058/night
Beachfront Condo – Location, Location, Location
Wailea, Hawaii
★★★★★ 9.8/10 · 9 reviews
Welcome to Makena Surf F305, your ideal vacation rental for a dream-filled island getaway! This stunning oceanfront residence, located on the third...
From $2,001/night
Cool Wailea Villa with Arcade Machine
Wailea, Hawaii
★★★★★ 9.8/10 · 9 reviews
Indulge in entertainment abound when vacationing in Wailea Beach Villas Penthouse 211. After you've spent an action-packed day at the beach or hiking...
From $245/night
Fairway + Pacific Ocean Views | Wailea Ekolu 910
Wailea, Hawaii
★★★★★ 9.8/10 · 7 reviews
Discover the perfect Hawaiian retreat at Wailea Ekolu Village with this stunning two-bedroom, two-bathroom ocean view rental. This premium condo...
From $1,235/night
Recently Renovated - Walk to the Beach
Wailea, Hawaii
★★★★★ 9.8/10 · 7 reviews
Wailea Elua 2502 is a beautifully renovated vacation rental located in the prestigious Wailea region of Maui. This spacious two-bedroom, two-bathroom...
From $1,394/night
Beachfront Condo - Steps from Wailea Beach Path
Wailea, Hawaii
★★★★★ 9.8/10 · 7 reviews
Polo Beach Club 206 is a second-floor vacation rental located in the renowned Wailea area of Maui. This condo offers a prime beachfront experience...
From $1,620/night
Makena Surf E103 | Ground-Floor Oceanfront Front-Row with Direct Beach Access
Wailea, Hawaii
★★★★★ 9.8/10 · 7 reviews
CORALTREE RESIDENCE COLLECTION presents... Makena Surf E103 A premier 1,510 sq.ft. 2-bedroom oceanfront condo on the ground floor, offering step-free...
From $650/night
Wailea Ekahi 51E, Amazing Ocean Views, Walk to Beach, Sunset View, Large Lanai
Wailea, Hawaii
★★★★★ 9.6/10 · 138 reviews
View! View! View! Imagine sipping gourmet coffee while enjoying the stunning ocean views and listening to the birds chirping! Imagine waking up to...
From $300/night
Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&Pool
Wailea, Hawaii
★★★★★ 9.6/10 · 98 reviews
Hale Wailea 6D – Wailea Ekahi Village[TA-164-628-0704-01]Welcome to Hale Wailea 6D, an elegantly updated, spacious second-floor condo nestled within...
From $355/night
Wailea Luxury on a Budget at Grand Champion Villas - 2 Bd+2 Bath
Wailea, Hawaii
★★★★★ 9.6/10 · 93 reviews
***4th night free offers good through October 2026 - discount added when reservation is madeBldg. 13 - Unit #118 - wonderful upgrades in a...
From $461/night
360 Ocean Views + Full Remodel! Top Floor # 904!
Wailea, Hawaii
★★★★★ 9.6/10 · 93 reviews
When you think of Hawaii you imagine awe-inspiring views, amazing sunsets and the natural beauty of the wild blue Pacific. These sights are a daily...
From $575/night
Palms At Wailea 2002- RARE FIND - Multi Level townhouse in Wailea!
Wailea, Hawaii
★★★★★ 9.6/10 · 91 reviews
This 3 bedroom 3 bath multi level condominium apartment is like a private home! From the entry you can step up to the open living area with a ocean...
From $466/night
1A Newly renovated w/porcelain tile floors, custom cabinets, granite countertops
Wailea, Hawaii
★★★★★ 9.6/10 · 90 reviews
Unit 1A is located on beautiful Keawakapu Beach in gorgeous Wailea. This recently major renovated lower village, ground floor unit has two lanais;...
From $1,309/night
Oceanfront Maui condo w/ lanai and island views
Wailea, Hawaii
★★★★★ 9.6/10 · 72 reviews
Relax on the lanai and enjoy sweeping views of Molokini and Kahoolawe Island at sunrise or sunset. Stroll along the world famous Wailea Beach Path,...
From $245/night
Ocean and fairway views in this spacious, top-floor, 3-BR Grand Champion Villa!
Wailea, Hawaii
★★★★★ 9.6/10 · 70 reviews
Experience gorgeous ocean and fairway views from this spacious top floor, tastefully decorated, family-friendly, three-bedroom unit. This beautiful...
From $370/night
Wailea Ekahi 31B, 1 BR/2BA, Lower Greenbelt, Ocean View
Wailea, Hawaii
★★★★★ 9.6/10 · 51 reviews
Please read under Rules & policies-Rental Agreement the new COVID-19 Rules & Guidelines- and the Waiver of Liability Agreement that must be signed...
From $1,404/night
Ho'olei Two-Story Townhome with Gourmet Kitchen and Resort Amenities
Wailea, Hawaii
★★★★★ 9.6/10 · 47 reviews
This Ho'olei two-story townhome offers elegant indoor-outdoor living on Maui with sliding pocket doors opening to a spacious private lanai for...
From $311/night
Fantastic Wailea Ekahi Beachfront Condo 45F
Wailea, Hawaii
★★★★★ 9.6/10 · 46 reviews
Welcome to my sunny Wailea Paradise! This refreshed and tastefully decorated second-floor condo (Unit 45F) has fantastic ocean and garden views and...
From $368/night
Beautiful Wailea Retreat with Pool, Lanai & Beach Access
Wailea, Hawaii
★★★★★ 9.6/10 · 43 reviews
Fabulous condo! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this popular complex...
From $705/night
*Stroll To The Beach Til Toes In The Sand!*Beautiful Views*Ground Floor*4 Pools*
Wailea, Hawaii
★★★★★ 9.6/10 · 42 reviews
Wailea Ekahi Village Two bedroom, two-bath, 1505 sq ft. completely remodeled and upgraded, ground floor condo, sleeps six is situated in a low-rise...
From $1,369/night
Beachfront Wailea condo w/ ocean views and lanai
Wailea, Hawaii
★★★★★ 9.6/10 · 39 reviews
Magnificent ocean views from Polo Beach Club 705, with direct beach access! Enjoy the serenity and privacy of one of the best locations in Wailea.As...
From $1,980/night
Steps to Ulua Beach-Wailea Elua 3-Bdr/3-Bath Beachfront Townhouse #1004
Wailea, Hawaii
★★★★★ 9.6/10 · 39 reviews
This is the one, the best location at Elua. Recently upgraded, Beachfront 3 BD+3 BA private townhouse with a courtyard and a private beach lanai. New...
From $395/night
Heart of Wailea, Remodeled Kitchen + AC! Ekahi 45A
Wailea, Hawaii
★★★★★ 9.6/10 · 38 reviews
Full remodel! New AC, appliances and furnishings! Wailea Ekahi 45A is a 1 bed, 2 bath condo conveniently located on the ground floor. It has...
From $753/night
Elua Village Contemporary 2bd+2ba Oceanview
Wailea, Hawaii
★★★★★ 9.6/10 · 38 reviews
New and Fresh! Lots of new features in Wailea Elua Village 2001. We have been busy with major upgrades! New carpet and paint, new beds, new sliding...
From $566/night
Wailea Condo Near Keawakapu Beach with Pool & Tropical Setting
Wailea, Hawaii
★★★★★ 9.6/10 · 37 reviews
If you are looking for a perfect getaway in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi...
From $146/night
Peaceful Wailea Condo Near Keawakapu Beach & Resort Pool
Wailea, Hawaii
★★★★★ 9.6/10 · 30 reviews
Palms at Wailea Luxury Condo | Spacious Ground-Floor RetreatExperience the best of Wailea at this beautifully decorated ground-floor condo at The...
From $791/night
Wailea Elua Village Fresh and Contemporary 2Bdr+2 Bath Oceanview Condominium
Wailea, Hawaii
★★★★★ 9.6/10 · 29 reviews
*** Please note there is construction work to the right of the property by the Andaz from August 18th to 25th that will be pretty noisy**Top Floor...
From $254/night
Spacious Wailea Maui Condo with Pool & Tropical Garden Setting
Wailea, Hawaii
★★★★★ 9.6/10 · 21 reviews
Experience the ultimate South Maui escape at Palms at Wailea 1201, a beautifully appointed 2-bedroom, 2-bath Wailea vacation rental designed for...
From $1,144/night
5th Floor Elevated Ocean Views | Polo Beach Club 508
Wailea, Hawaii
★★★★★ 9.6/10 · 15 reviews
Polo Beach Club 508 is a stunning oceanfront vacation rental located in the heart of the luxurious Wailea area of Maui. This two-bedroom,...