Nicely Updated-Sleeps 8-WELL Equipped-Ac-Meticulous CleaningFrom $706/night · Sleeps 8
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
Nicely Updated-Sleeps 8-WELL Equipped-Ac-Meticulous CleaningFrom $706/night · Sleeps 8
Oceanfront Maui condo w/ pool, hot tub and lanai viewsFrom $1,051/night · Sleeps 6
Rare Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview LanaiFrom $1,328/night · Sleeps 6
Summer Deal Ocean View Wailea Villa with Pool and Resort Hot TubsFrom $997/night · Sleeps 8
Stunning NEW Remodel-Sunsets-Luxury-Quiet Location-Ac-Large LanaiFrom $300/night · Sleeps 4
ContemporaryHawaiianReno in Wailea*Pool*Beach*GolfFrom $335/night · Sleeps 6
Summer Deal Wailea Condo with Lanai Pool and Golf Course ViewsFrom $396/night · Sleeps 6
Oceanfront Maui condo w/ sunset lanai and pool accessFrom $421/night · Sleeps 2
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4From $1,499/night · Sleeps 8
Elegant Wailea Renovated 2BR Condo Panoramic Ocean and Haleakala Views PoolFrom $1,617/night · Sleeps 6
Luxurious Ho'olei Villa with Ocean Views, Two Story Townhouse!From $1,892/night · Sleeps 6
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private LanaiFrom $423/night · Sleeps 6
Peaceful Wailea Retreat Near Keawakapu Beach & Resort PoolFrom $222/night · Sleeps 6
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu BeachFrom $463/night · Sleeps 4
Luxurious Wailea 2BR Condo Full Ocean and Fairway Views Two Pools Near BeachFrom $305/night · Sleeps 4
2nd Floor Ocean Views | Epic Sunsets | Makena Surf F208From $792/night · Sleeps 6
Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous KiheiFrom $312/night · Sleeps 6
Makena Surf B106 | Ground Floor Beach Access, Turtle Reef & High-End KitchenFrom $1,177/night · Sleeps 6
Sunset & Ocean Views | Platinum RatedFrom $642/night · Sleeps 4
Modern Renovation with Ocean Views | Wailea Elua 905From $1,326/night · Sleeps 8
Wailea Villa Overlooking Lagoon PoolFrom $2,537/night · Sleeps 8
3BD Golf Haven - Great for FamiliesFrom $297/night · Sleeps 7
Wailea oceanfront condo w/ Keawakapu Beach accessFrom $548/night · Sleeps 4
Spacious Ocean View Condo - Perfect For FamiliesFrom $573/night · Sleeps 6
Large Floorplan - Great for Families | Grand Champions 159From $458/night · Sleeps 8
Top Floor Wrap-Around Ocean Views - PH512From $2,818/night · Sleeps 6
Wailea Elua: Huge Ocean Views, Pool, AC & Hot TubFrom $1,225/night · Sleeps 6
Oceanviews, Fresh Upgrades at the Luxurious Grand Seascape K407!!From $2,195/night · Sleeps 6
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025From $1,599/night · Sleeps 8
Elegant Wailea Remodeled 2BR Condo Saltwater Pool Steps to Keawakapu BeachFrom $492/night · Sleeps 6
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand ChampionsFrom $533/night · Sleeps 6
Voted Top 10 Resort in Hawaii - Wailea Beach Villas F201From $3,655/night · Sleeps 8
Polo Beach Club 801 | 8th Floor Ocean Views, Beachfront Pool & Beach AccessFrom $669/night · Sleeps 4
From $706/night
Nicely Updated-Sleeps 8-WELL Equipped-Ac-Meticulous Cleaning
Wailea, Hawaii
★★★★★ 10.0/10 · 52 reviews
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that has been nicely updated. This condo is managed by PMI Maui, a local...
From $1,051/night
Oceanfront Maui condo w/ pool, hot tub and lanai views
Wailea, Hawaii
★★★★★ 10.0/10 · 51 reviews
Book Your Stay and Get a $300 Gift Card!Planning a getaway? Book a stay of 5+ nights between September 24th and November 9th, and you'll receive a...
From $1,328/night
Rare Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview Lanai
Wailea, Hawaii
★★★★★ 10.0/10 · 49 reviews
This is the one! If it's available, you'll want to reserve it. A real Maui home-away-from-home. New carpet in bedrooms, new bedroom furniture, lots...
From $997/night
Summer Deal Ocean View Wailea Villa with Pool and Resort Hot Tubs
Wailea, Hawaii
★★★★★ 10.0/10 · 46 reviews
Ho'olei Villa 17-1 is a beautifully remodeled 3-bedroom, 3.5-bath townhome offering stunning ocean views and breathtaking sunsets. Located in...
From $300/night
Stunning NEW Remodel-Sunsets-Luxury-Quiet Location-Ac-Large Lanai
Wailea, Hawaii
★★★★★ 10.0/10 · 45 reviews
Book with confidence, this stunning, 1 bedroom, 2 bathroom (1022 sq. ft) condo that has been completely remodeled from top to bottom with modern...
From $335/night
ContemporaryHawaiianReno in Wailea*Pool*Beach*Golf
Wailea, Hawaii
★★★★★ 10.0/10 · 44 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 $396/night
Summer Deal Wailea Condo with Lanai Pool and Golf Course Views
Wailea, Hawaii
★★★★★ 10.0/10 · 44 reviews
Location! Location! Location! Who needs a car?!? This central Wailea location makes it favorable as you can find tennis, golf, retailers at the Shops...
From $421/night
Oceanfront Maui condo w/ sunset lanai and pool access
Wailea, Hawaii
★★★★★ 10.0/10 · 34 reviews
Unique opportunity to stay in a one-bedroom, top floor home at one of the most desired properties on Maui. Polo Beach #808 will be your favorite...
From $1,499/night
Panoramic Views - Fourth Row Ho'olei - One of a Kind 112-4
Wailea, Hawaii
★★★★★ 10.0/10 · 34 reviews
Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo perched on the very top row...
From $1,617/night
Elegant Wailea Renovated 2BR Condo Panoramic Ocean and Haleakala Views Pool
Wailea, Hawaii
★★★★★ 10.0/10 · 34 reviews
For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly...
From $1,892/night
Luxurious Ho'olei Villa with Ocean Views, Two Story Townhouse!
Wailea, Hawaii
★★★★★ 10.0/10 · 34 reviews
This Ho'olei ocean view villa is a luxurious two-story townhouse in Wailea, offering sweeping ocean views and elegant island living. This spacious...
From $423/night
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private Lanai
Wailea, Hawaii
★★★★★ 10.0/10 · 30 reviews
Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your...
From $222/night
Peaceful Wailea Retreat Near Keawakapu Beach & Resort Pool
Wailea, Hawaii
★★★★★ 10.0/10 · 27 reviews
Welcome to Palms at Wailea 1904, a beautifully updated 2-bedroom, 2-bath vacation rental in the heart of Wailea. Perfect for families or couples...
From $463/night
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 26 reviews
Don't miss the best that Wailea Ekahi has to offer, 20G! Full kitchen and bathroom remodel with all new appliances and refreshed air conditioning,...
From $305/night
Luxurious Wailea 2BR Condo Full Ocean and Fairway Views Two Pools Near Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 25 reviews
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and...
From $792/night
2nd Floor Ocean Views | Epic Sunsets | Makena Surf F208
Wailea, Hawaii
★★★★★ 10.0/10 · 21 reviews
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor,...
From $312/night
Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous Kihei
Wailea, Hawaii
★★★★★ 10.0/10 · 20 reviews
Located in the heart of Kihei, this condo is a dream. With 2 bedrooms featuring two king beds with ceiling fans, Queen size sleeper sofa in Living...
From $1,177/night
Makena Surf B106 | Ground Floor Beach Access, Turtle Reef & High-End Kitchen
Wailea, Hawaii
★★★★★ 10.0/10 · 19 reviews
CORALTREE RESIDENCE COLLECTION presents... Makena Surf B106!Experience an intimate Hawaiian retreat at this 2-bedroom ground-floor condo on...
From $642/night
Sunset & Ocean Views | Platinum Rated
Wailea, Hawaii
★★★★★ 10.0/10 · 18 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 30DThis spacious 945 sq.ft. 1-bedroom condo with 2 full bathrooms offers elevated...
From $1,326/night
Modern Renovation with Ocean Views | Wailea Elua 905
Wailea, Hawaii
★★★★★ 10.0/10 · 18 reviews
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a...
From $2,537/night
Wailea Villa Overlooking Lagoon Pool
Wailea, Hawaii
★★★★★ 10.0/10 · 18 reviews
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the...
From $297/night
3BD Golf Haven - Great for Families
Wailea, Hawaii
★★★★★ 10.0/10 · 17 reviews
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. This spacious three-bedroom,...
From $548/night
Wailea oceanfront condo w/ Keawakapu Beach access
Wailea, Hawaii
★★★★★ 10.0/10 · 17 reviews
Located just moments away from the pristine beaches, this elegant condo offers the perfect balance of tranquility and convenience. Explore the nearby...
From $573/night
Spacious Ocean View Condo - Perfect For Families
Wailea, Hawaii
★★★★★ 10.0/10 · 16 reviews
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning...
From $458/night
Large Floorplan - Great for Families | Grand Champions 159
Wailea, Hawaii
★★★★★ 10.0/10 · 15 reviews
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This...
From $2,818/night
Top Floor Wrap-Around Ocean Views - PH512
Wailea, Hawaii
★★★★★ 10.0/10 · 15 reviews
Penthouse 512 at Wailea Beach Villas offers an unparalleled top-floor experience with expansive ocean and island views, ideal for a Hawaiian dream...
From $1,225/night
Wailea Elua: Huge Ocean Views, Pool, AC & Hot Tub
Wailea, Hawaii
★★★★★ 10.0/10 · 14 reviews
Summary:Nestled in the scenic beauty of Wailea, this inviting condo promises a delightful escape with everything you need for a memorable stay....
From $2,195/night
Oceanviews, Fresh Upgrades at the Luxurious Grand Seascape K407!!
Wailea, Hawaii
★★★★★ 10.0/10 · 14 reviews
Situated in the centrally located "Penthouse" building on the 4th floor in a west-facing ocean view corner location with breathtakingly beautiful...
From $1,599/night
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
Wailea, Hawaii
★★★★★ 10.0/10 · 13 reviews
Remodel completed in 2025!Thoughtfully redesigned by the owners in collaboration with an internationally acclaimed interior designer, this...
From $492/night
Elegant Wailea Remodeled 2BR Condo Saltwater Pool Steps to Keawakapu Beach
Wailea, Hawaii
★★★★★ 10.0/10 · 12 reviews
** PLEASE NOTE: The Pool will be closed from September 15th - September 18th, 2026, for yearly maintenance. Welcome to The Palms at Wailea, where we...
From $533/night
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions
Wailea, Hawaii
★★★★★ 10.0/10 · 12 reviews
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is...
From $3,655/night
Voted Top 10 Resort in Hawaii - Wailea Beach Villas F201
Wailea, Hawaii
★★★★★ 10.0/10 · 12 reviews
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious...
From $669/night
Polo Beach Club 801 | 8th Floor Ocean Views, Beachfront Pool & Beach Access
Wailea, Hawaii
★★★★★ 10.0/10 · 11 reviews
CORAL TREE RESIDENCE MAUI COLLECTION presents... Polo Beach Club 801 Experience an elevated Hawaiian getaway at this top-floor 2-bedroom oceanfront...