Stunning Ocean Views - Professionally Managed - Elua 107From $853/night · Sleeps 4
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
Stunning Ocean Views - Professionally Managed - Elua 107From $853/night · Sleeps 4
Walk to Wailea Beach & Shops at WaileaFrom $1,227/night · Sleeps 6
Recently Renovated at Wailea Beach VillasFrom $1,228/night · Sleeps 6
Comfortable Design with Ocean ViewsFrom $2,329/night · Sleeps 8
Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the BeachFrom $536/night · Sleeps 8
Incredibly Large Polynesian Style Villa in WaileaFrom $389/night · Sleeps 6
1 BR Treetop Wailea, 2nd floor vaulted ceilingsFrom $232/night · Sleeps 2
This is a Gem! Wailea 1 BD+2 BA Grand Champions VillaFrom $257/night · Sleeps 4
Treetop Studio 2nd floor, corner unitFrom $185/night · Sleeps 2
TOP Floor Corner Private Studio, Affordable Wailea, Walk to BeachFrom $249/night · Sleeps 2
Wailea Sunset Condo -Wailea Ekolu Village #607- Spring & Summer Get Away SpecialFrom $246/night · Sleeps 4
Completely Remodeled-Ac Throughout-Ground Floor-Meticulous CleaningFrom $299/night · Sleeps 6
You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.From $375/night · Sleeps 4
Ho'olei #93-2-BEAUTIFULLY Appointed Villa-Sleeps 8-METICULOUS CleaningFrom $1,407/night · Sleeps 10
Tranquil Oceanfront Escape! Central AC! Polo 402!From $573/night · Sleeps 5
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split ACFrom $601/night · Sleeps 6
1BR, 2BA! Enjoy fairway, & partial ocean views from your private lanai!From $277/night · Sleeps 4
Beachfront Wailea condo w/ pool, hot tub and sunset lanaiFrom $1,208/night · Sleeps 6
Beachfront condo steps from Keawakapu Beach w/ ocean viewsFrom $378/night · Sleeps 4
Ho'olei #24-3-BEAUTIFULLY Appointed Villa-Sleeps 10-METICULOUS CleaningFrom $1,272/night · Sleeps 10
Ultimate Luxury: Chef's Kitchen, Soaking Tub, & Private Lanai in Stunning Villa!From $1,282/night · Sleeps 8
Fresh and New Luxury Elua Village 2 Bdrm+2 Bath Paradise Condominium #907From $698/night · Sleeps 6
Summer Deal Wailea Villa with Golf Course Views and Resort PoolsFrom $227/night · Sleeps 6
Exquisite Remodel-Sleeps 8-WELL Equipped-Ac-Meticulous CleaningFrom $260/night · Sleeps 8
Enjoy comfort in Wailea, a spacious 2BD/2BA condo with garden viewsFrom $173/night · Sleeps 6
Remodeled-Large Lanai-Resort Living-Ac-Ocean Views-Meticulous CleaningFrom $345/night · Sleeps 4
Wailea Elua Top Floor 2 Bdrm/2 Bath Oceanview Unit - 1 min walk to Ulua BeachFrom $627/night · Sleeps 6
Beautiful Brand NEW Remodel-Ocean Views-Sleeps 8-AC-WELL EquippedFrom $315/night · Sleeps 8
Unbeatable Ocean-View Condo in Palms at WaileaFrom $328/night · Sleeps 4
Ocean view-close to beach!Remodeled!Sleeps 5!Bldg 30 Remaining Fall $199/nt!From $199/night · Sleeps 5
Paradise in Wailea-3 bed/2 bath Grand Champion 94 - big lanai and ocean viewsFrom $572/night · Sleeps 8
Wailea Beach Villas PH112 - Professional ManagedFrom $1,276/night · Sleeps 6
Sublime Ocean Views - Polo Beach 408From $1,779/night · Sleeps 4
From $853/night
Stunning Ocean Views - Professionally Managed - Elua 107
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor...
From $1,227/night
Walk to Wailea Beach & Shops at Wailea
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and...
From $1,228/night
Recently Renovated at Wailea Beach Villas
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean...
From $2,329/night
Comfortable Design with Ocean Views
Wailea, Hawaii
★★★★★ 10.0/10 · 1 reviews
Wailea Elua 904 is a stunning vacation rental property that offers a luxurious island getaway. Nestled within the upscale Wailea resort community,...
From $536/night
Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the Beach
Wailea, Hawaii
★★★★★ 9.8/10 · 202 reviews
Located in the lower village, ground floor unit #20C has two lanais and a patio. The condo is surrounded by a private, tropical lawn area where...
From $389/night
Incredibly Large Polynesian Style Villa in Wailea
Wailea, Hawaii
★★★★★ 9.8/10 · 153 reviews
Spend your vacation in this villa like Polynesian style vacation rental located at the beautiful Palms at Wailea Resort on the Maui's prestigious...
From $232/night
1 BR Treetop Wailea, 2nd floor vaulted ceilings
Wailea, Hawaii
★★★★★ 9.8/10 · 130 reviews
The Tree Top One Bedroom, is an elegant, bright 2nd floor unit with tropical modern king bedroom, teak and rattan furnishings, spacious bath with...
From $257/night
This is a Gem! Wailea 1 BD+2 BA Grand Champions Villa
Wailea, Hawaii
★★★★★ 9.8/10 · 112 reviews
New Furniture! New personal amenities! new soft goods! Unit #54, building 6. An impeccable 1 Bedroom + 2 Bathroom paradise condominium at the Wailea...
From $185/night
Treetop Studio 2nd floor, corner unit
Wailea, Hawaii
★★★★★ 9.8/10 · 108 reviews
This studio offers private lanai and kitchenette with sink, full size fridge and microwave. King size bed, and remodeled bathroom with walk-in...
From $249/night
TOP Floor Corner Private Studio, Affordable Wailea, Walk to Beach
Wailea, Hawaii
★★★★★ 9.8/10 · 100 reviews
Last minute DISCOUNTED RATES We appreciate your support as a small, self managed Maui family owned rental instead of renting from a large mainland...
From $246/night
Wailea Sunset Condo -Wailea Ekolu Village #607- Spring & Summer Get Away Special
Wailea, Hawaii
★★★★★ 9.8/10 · 94 reviews
Escape to our bright, ground-floor Wailea condo with panoramic ocean views from every room! This remodeled 1-bed, 2-bath paradise comfortably sleeps...
From $299/night
Completely Remodeled-Ac Throughout-Ground Floor-Meticulous Cleaning
Wailea, Hawaii
★★★★★ 9.8/10 · 94 reviews
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1200 sq. ft) condo that has been completely remodeled. This condo is managed by PMI Maui,...
From $375/night
You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.
Wailea, Hawaii
★★★★★ 9.8/10 · 88 reviews
ALOHA!Start your day with coffee and beautiful ocean views from the lanai, and finish the day watching amazing sunsets!Immerse yourself in the warmth...
From $1,407/night
Ho'olei #93-2-BEAUTIFULLY Appointed Villa-Sleeps 8-METICULOUS Cleaning
Wailea, Hawaii
★★★★★ 9.8/10 · 80 reviews
Book With Confidence This Luxurious 3 Bedroom, 3.5 Bathroom (2426 sq. ft) Villa That Provides Everything That You Need To Have A Great Vacation. The...
From $573/night
Tranquil Oceanfront Escape! Central AC! Polo 402!
Wailea, Hawaii
★★★★★ 9.8/10 · 76 reviews
Book 5 nights and enjoy the 6th night free! Valid for all new reservations arriving after 1/15/2025.This updated condo in a gorgeous oceanfront...
From $601/night
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Wailea, Hawaii
★★★★★ 9.8/10 · 74 reviews
Welcome to Wailea Ekolu 310, experience breathtaking, panoramic ocean views from main living area and over-sized lanai of this spacious single level...
From $277/night
1BR, 2BA! Enjoy fairway, & partial ocean views from your private lanai!
Wailea, Hawaii
★★★★★ 9.8/10 · 67 reviews
Renovated 1 Bedroom 2 Bathroom! Kick back and relax on your own private lanai and take in wonderful garden, fairway, and partial ocean views. Feel...
From $1,208/night
Beachfront Wailea condo w/ pool, hot tub and sunset lanai
Wailea, Hawaii
★★★★★ 9.8/10 · 67 reviews
Start your day with a stroll along the world-famous beachfront path, which ends right in front of this property. You can enjoy the peaceful,...
From $378/night
Beachfront condo steps from Keawakapu Beach w/ ocean views
Wailea, Hawaii
★★★★★ 9.8/10 · 64 reviews
Welcome to Wailea Ekahi Village 26A, two bedroom/two bathroom ground-floor condominium unit that has been completely renovated and offers a clean,...
From $1,272/night
Ho'olei #24-3-BEAUTIFULLY Appointed Villa-Sleeps 10-METICULOUS Cleaning
Wailea, Hawaii
★★★★★ 9.8/10 · 60 reviews
Book With Confidence This Luxurious 3 Bedroom, 3.5 Bathroom (2619 sq. ft) Villa That Provides Everything That You Need To Have A Great Vacation. The...
From $1,282/night
Ultimate Luxury: Chef's Kitchen, Soaking Tub, & Private Lanai in Stunning Villa!
Wailea, Hawaii
★★★★★ 9.8/10 · 57 reviews
Special Luxury Promotion Book 7 Nights and Enjoy the 8th Night FreeIndulge in the ultimate getaway at our luxury residence and extend your stay on...
From $698/night
Fresh and New Luxury Elua Village 2 Bdrm+2 Bath Paradise Condominium #907
Wailea, Hawaii
★★★★★ 9.8/10 · 54 reviews
New, New, New! New furniture, new electronics, new beds, mattresses and linens, paint and artwork. Sooooo close to the beach! Treat yourself to the...
From $227/night
Summer Deal Wailea Villa with Golf Course Views and Resort Pools
Wailea, Hawaii
★★★★★ 9.8/10 · 53 reviews
Some of the features include: Travertine Tile, Granite, Marble, Top of the line Stainless Steel Appliances, Mahogany Cabinets, Luxury, Quality...
From $260/night
Exquisite Remodel-Sleeps 8-WELL Equipped-Ac-Meticulous Cleaning
Wailea, Hawaii
★★★★★ 9.8/10 · 53 reviews
Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been completely remodeled from top to bottom. This condo is...
From $173/night
Enjoy comfort in Wailea, a spacious 2BD/2BA condo with garden views
Wailea, Hawaii
★★★★★ 9.8/10 · 50 reviews
Experience the best of Wailea at Grand Champions 130, a spacious top-floor two-bedroom condo surrounded by lush tropical landscaping. Featuring two...
From $345/night
Remodeled-Large Lanai-Resort Living-Ac-Ocean Views-Meticulous Cleaning
Wailea, Hawaii
★★★★★ 9.8/10 · 48 reviews
Book with confidence, Wailea Ekahi 18F is a brand new luxurious condo. This condo is managed by PMI Maui, a local Real Estate Brokerage that...
From $627/night
Wailea Elua Top Floor 2 Bdrm/2 Bath Oceanview Unit - 1 min walk to Ulua Beach
Wailea, Hawaii
★★★★★ 9.8/10 · 43 reviews
Treat yourself to this roomy and relaxing top 2 bedroom + 2 full bathroom vacation condominium steps to the beach and pools with convenient parking....
From $315/night
Beautiful Brand NEW Remodel-Ocean Views-Sleeps 8-AC-WELL Equipped
Wailea, Hawaii
★★★★★ 9.8/10 · 37 reviews
Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been newly remodeled. This condo is managed by PMI Maui, a local...
From $328/night
Unbeatable Ocean-View Condo in Palms at Wailea
Wailea, Hawaii
★★★★★ 9.8/10 · 33 reviews
Discover the pinnacle of luxury island living in Wailea Maui, where this newly remodeled 2-bedroom, 2-bathroom condo in the prestigious Palms of...
From $199/night
Ocean view-close to beach!Remodeled!Sleeps 5!Bldg 30 Remaining Fall $199/nt!
Wailea, Hawaii
★★★★★ 9.8/10 · 31 reviews
Note that the main pool will be closed August 10-October 15, 2026. The other three pools, beach pavilion kitchen, fitness centre, beach bathrooms,...
From $572/night
Paradise in Wailea-3 bed/2 bath Grand Champion 94 - big lanai and ocean views
Wailea, Hawaii
★★★★★ 9.8/10 · 24 reviews
Bldg. 10 - Unit #94 - New, New New. New roof, new carpet, new appliances, new bed - renewed throughout, an impeccable 3 Bedroom + 2 Bathroom paradise...
From $1,276/night
Wailea Beach Villas PH112 - Professional Managed
Wailea, Hawaii
★★★★★ 9.8/10 · 18 reviews
Awaken to the sweet sounds of palm trees swaying in the tropical breeze from Wailea Beach Villas PH112. Spanning 2,500 square feet, this main level,...
From $1,779/night
Sublime Ocean Views - Polo Beach 408
Wailea, Hawaii
★★★★★ 9.8/10 · 18 reviews
Polo Beach Club 408 is a stunningly renovated vacation rental that offers breathtaking ocean views, making it an ideal getaway. Guests can relax on...