Recently Renovated - Iconic Ocean Views | Polo Beach 609From $1,296/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
Recently Renovated - Iconic Ocean Views | Polo Beach 609From $1,296/night · Sleeps 6
Panoramic Ocean Views - Makena Surf A203From $1,723/night · Sleeps 6
Fabulous Ulua Beach & Lush Grounds Await: Wailea Elua 807, Ground floor Gem!From $839/night · Sleeps 2
Wailea Ekahi 17B | Spacious Lanai with Ocean Views, Beach Wagon & ChairsFrom $364/night · Sleeps 4
Prime Wailea Location! Wailea Ekahi 37EFrom $559/night · Sleeps 5
Wailea Elua Village 2401 | Wrap-Around Lanai, Ocean View & Ulua BeachFrom $1,260/night · Sleeps 4
Sunset Views | Snorkeling | Resort Amenities - Makena Surf B205From $770/night · Sleeps 4
Sunset Views | Whale Watching | Resort AmenitiesFrom $1,169/night · Sleeps 6
Fine Art + Ocean Views | Professionally ManagedFrom $3,934/night · Sleeps 8
Beachfront & Modern | Makena Surf A102From $1,119/night · Sleeps 6
Front Yard is the Beach - Elua 1607From $2,432/night · Sleeps 6
Wailea Elua Village 208 | Ocean View, 2 Full Baths, 2 Min to Ulua BeachFrom $834/night · Sleeps 4
Beachfront Condo – Location, Location, LocationFrom $2,735/night · Sleeps 4
360 Premier Ocean View! Remodeled Ekolu # 1510!From $326/night · Sleeps 6
Beachfront condo Wailea w/ lanai and pool accessFrom $1,371/night · Sleeps 6
Wailea Ekahi #8-B Partial Ocean View, Steps to Beach, Easy access to PoolFrom $675/night · Sleeps 4
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!From $289/night · Sleeps 4
Stunning Views, Walk to Beach! Spacious Ekahi 49FFrom $336/night · Sleeps 2
Stunning Remodeled Unit with Ocean Views! Ekahi 5EFrom $583/night · Sleeps 3
Oceanfront Wailea condo w/ pool, hot tub and beach accessFrom $579/night · Sleeps 6
Ocean & Garden Views Await at Wailea Ekahi 34B: Spacious 1BR/2BA Ground FloorFrom $468/night · Sleeps 4
Grand Champions 108 | Sunset Views + AmenitiesFrom $304/night · Sleeps 2
Ocean Views + Exquisite getaway Wailea Ekahi 53D!From $305/night · Sleeps 2
Beautiful Wailea Retreat with Garden Views & Resort PoolFrom $614/night · Sleeps 6
Oceanfront Wailea condo w/ Molokini views and pool accessFrom $1,410/night · Sleeps 4
Spacious Ground Floor Revitalized Oasis- Discover Wailea Ekahi #22BFrom $320/night · Sleeps 4
KBM Resorts | FREE CAR | Wailea Elua Village | Ocean view | Spacious 2-Bedroom Condo! WEV-2103From $1,154/night · Sleeps 6
FALL SPECIAL! Enjoy Maui for Less. Short walk to Wailea Beach!!From $199/night · Sleeps 4
Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous InteriorFrom $669/night · Sleeps 4
Ground Floor Bliss By The BeachFrom $307/night · Sleeps 4
Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guestsFrom $388/night · Sleeps 6
Golf + Ocean Views | Wailea Ekolu 1205From $245/night · Sleeps 4
Golf Retreat Great for FamiliesFrom $503/night · Sleeps 4
From $1,296/night
Recently Renovated - Iconic Ocean Views | Polo Beach 609
Wailea, Hawaii
★★★★★ 9.6/10 · 14 reviews
Polo Beach Club 609 is a newly remodeled and well-appointed retreat, perfect for small families and groups seeking comfort and relaxation. The...
From $1,723/night
Panoramic Ocean Views - Makena Surf A203
Wailea, Hawaii
★★★★★ 9.6/10 · 13 reviews
Indulge in luxury at this stunning two-story townhouse, featuring a primary retreat on the second floor complete with a lavish bath and a private...
From $839/night
Fabulous Ulua Beach & Lush Grounds Await: Wailea Elua 807, Ground floor Gem!
Wailea, Hawaii
★★★★★ 9.6/10 · 12 reviews
Wailea Elua #807 – Ground-Floor Serenity with Ocean Breezes and Refined ComfortWelcome to Wailea Elua #807, a beautifully appointed ground-floor,...
From $364/night
Wailea Ekahi 17B | Spacious Lanai with Ocean Views, Beach Wagon & Chairs
Wailea, Hawaii
★★★★★ 9.6/10 · 11 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 17BA spacious 1,000-sq.ft. 1-bedroom condo with 2 full bathrooms, offering step-free...
From $559/night
Prime Wailea Location! Wailea Ekahi 37E
Wailea, Hawaii
★★★★★ 9.6/10 · 9 reviews
• Stay 5 Nights, Get the 6th FreeBook a stay for September 27th - October 31st, and enjoy the 6th night free! Perfect for extending your getaway at...
From $1,260/night
Wailea Elua Village 2401 | Wrap-Around Lanai, Ocean View & Ulua Beach
Wailea, Hawaii
★★★★★ 9.6/10 · 9 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 2401Elua Village sits adjacent to Ulua Beach and connects directly to the 3.2-mile...
From $770/night
Sunset Views | Snorkeling | Resort Amenities - Makena Surf B205
Wailea, Hawaii
★★★★★ 9.6/10 · 8 reviews
Makena Surf B205 is an exquisite oceanfront vacation rental located within the luxurious Makena Surf resort, nestled on the stunning Po\'olenalena...
From $1,169/night
Sunset Views | Whale Watching | Resort Amenities
Wailea, Hawaii
★★★★★ 9.6/10 · 8 reviews
Wailea Beach Villas Penthouse 302 is a luxurious ocean-view retreat blending modern design with Maui's natural beauty. This 1,900 sq. ft. penthouse...
From $3,934/night
Fine Art + Ocean Views | Professionally Managed
Wailea, Hawaii
★★★★★ 9.6/10 · 7 reviews
Discover for yourself why D301 is one of the most requested Villas in our vacation rental collection. Impressive artwork by internationally known...
From $1,119/night
Beachfront & Modern | Makena Surf A102
Wailea, Hawaii
★★★★★ 9.6/10 · 5 reviews
The recently renovated Makena Surf A102 is a prime oceanfront vacation home spanning 1,510 square feet. This ground-floor unit boasts direct beach...
From $2,432/night
Front Yard is the Beach - Elua 1607
Wailea, Hawaii
★★★★★ 9.6/10 · 5 reviews
Wailea Elua 1607 is a luxurious ground floor oceanfront vacation rental located in the exclusive Wailea Elua Village. This spacious 1,701 square foot...
From $834/night
Wailea Elua Village 208 | Ocean View, 2 Full Baths, 2 Min to Ulua Beach
Wailea, Hawaii
★★★★★ 9.6/10 · 4 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 208Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $2,735/night
Beachfront Condo – Location, Location, Location
Wailea, Hawaii
★★★★★ 9.6/10 · 4 reviews
Wailea Elua Village #1001 is a luxurious oceanfront haven in the heart of Wailea, offering panoramic views and contemporary island elegance just...
From $326/night
360 Premier Ocean View! Remodeled Ekolu # 1510!
Wailea, Hawaii
★★★★★ 9.4/10 · 87 reviews
This is a premier unit with panoramic ocean views located just minutes to all Wailea Beaches, The Shops at Wailea and Luxury Hotels! This beautiful...
From $1,371/night
Beachfront condo Wailea w/ lanai and pool access
Wailea, Hawaii
★★★★★ 9.4/10 · 87 reviews
The location cannot be beat! There is no other accommodation closer to the beach in Wailea! Start your day walking the famed Wailea Beach Path, which...
From $675/night
Wailea Ekahi #8-B Partial Ocean View, Steps to Beach, Easy access to Pool
Wailea, Hawaii
★★★★★ 9.4/10 · 73 reviews
1 Bedroom Condo, Steps to Keawakapu Beach, 60 steps to Oceanfront Pool.This ground floor one bedroom two bath has a/c throughout. It boasts a large...
From $289/night
CLEAN, GREAT LOCATION, PRIVATE, Vaulted Ceilings, Lots of amenities, Oceanview!
Wailea, Hawaii
★★★★★ 9.4/10 · 67 reviews
DISCOUNTED RATES FOR LAST MINUTE OPENINGSWe appreciate your support as a small, self managed Maui family owned rental instead of renting from a large...
From $336/night
Stunning Views, Walk to Beach! Spacious Ekahi 49F
Wailea, Hawaii
★★★★★ 9.4/10 · 64 reviews
This listing has views from your lanai will have you coming back year after year--and the beach is a short stroll across the condo property! A cozy...
From $583/night
Stunning Remodeled Unit with Ocean Views! Ekahi 5E
Wailea, Hawaii
★★★★★ 9.4/10 · 63 reviews
Welcome to Ekahi 5E! This top floor unit boasts incredible ocean and garden views! It is nestled along a beautiful hillside that embraces the...
From $579/night
Oceanfront Wailea condo w/ pool, hot tub and beach access
Wailea, Hawaii
★★★★★ 9.4/10 · 58 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 $468/night
Ocean & Garden Views Await at Wailea Ekahi 34B: Spacious 1BR/2BA Ground Floor
Wailea, Hawaii
★★★★★ 9.4/10 · 42 reviews
Welcome to Wailea Ekahi 34B where lush tropical foliage surrounds you and views of the majestic Pacific await! This updated 1 bedroom / 2 bathroom...
From $304/night
Grand Champions 108 | Sunset Views + Amenities
Wailea, Hawaii
★★★★★ 9.4/10 · 41 reviews
Welcome to Grand Champions 108, a beacon of refined luxury in the heart of Wailea, Maui. This beautifully remodeled one-bedroom, two-bath villa...
From $305/night
Ocean Views + Exquisite getaway Wailea Ekahi 53D!
Wailea, Hawaii
★★★★★ 9.4/10 · 41 reviews
Special Offer: Book 8 or more nights, get 1 night free or Book 12 or more nights, get 2 nights free. Valid on all new reservations booked on or after...
From $614/night
Beautiful Wailea Retreat with Garden Views & Resort Pool
Wailea, Hawaii
★★★★★ 9.4/10 · 38 reviews
The name PALMS AT WAILEA aptly describes the feel of this beautiful complex. Located above the pristine shores of Keawakapu Beach, this impeccably...
From $1,410/night
Oceanfront Wailea condo w/ Molokini views and pool access
Wailea, Hawaii
★★★★★ 9.4/10 · 35 reviews
Polo Beach Club 205! Direct ocean front views! Located in the highly sought-after beachfront stack. Enjoy incredible views of Polo Beach, Molokini...
From $320/night
Spacious Ground Floor Revitalized Oasis- Discover Wailea Ekahi #22B
Wailea, Hawaii
★★★★★ 9.4/10 · 29 reviews
Wailea Ekahi #22B – Ground-Floor Elegance with Ocean Breezes and Garden ViewsStep into comfort, space, and tranquility at Wailea Ekahi #22B, a large...
From $1,154/night
KBM Resorts | FREE CAR | Wailea Elua Village | Ocean view | Spacious 2-Bedroom Condo! WEV-2103
Wailea, Hawaii
★★★★★ 9.4/10 · 27 reviews
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $199/night
FALL SPECIAL! Enjoy Maui for Less. Short walk to Wailea Beach!!
Wailea, Hawaii
★★★★★ 9.4/10 · 22 reviews
This beautiful, tropical two-bedroom/two-bath condo is just a short 5-minute walk from the world-famous Keawakapu Beach!! Enjoy dreamy sunset strolls...
From $669/night
Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior
Wailea, Hawaii
★★★★★ 9.4/10 · 15 reviews
Wailea Elua #302 – Top-Floor Ocean View Elegance with Artistic Hawaiian TouchesWelcome to Wailea Elua #302, a stunning 1-bedroom, 2-bathroom...
From $307/night
Ground Floor Bliss By The Beach
Wailea, Hawaii
★★★★★ 9.4/10 · 14 reviews
Walk to the beach in minutes from this ground floor condo at Wailea Ekahi Village. Slide open the glass lanai doors of Wailea Ekahi 15A and you will...
From $388/night
Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guests
Wailea, Hawaii
★★★★★ 9.4/10 · 10 reviews
*New Furniture throughout!! This two-bedroom, two-bath garden-view condo has just been remodeled with all new furniture throughout each room in the...
From $245/night
Golf + Ocean Views | Wailea Ekolu 1205
Wailea, Hawaii
★★★★★ 9.4/10 · 8 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1205 Perched above Wailea, 1205 is situated in the most walkable complex in our Maui...
From $503/night
Golf Retreat Great for Families
Wailea, Hawaii
★★★★★ 9.4/10 · 3 reviews
Wailea Grand Champions 75 is an exceptional vacation rental situated in the picturesque Wailea region of Maui. This luxurious property promises an...