Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
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 retreat, 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
- Ho'olei 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 perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
LUXURY OCEANFRONT MAKENA SURF - 3 BR/3 BA - CONTACT OWNER FOR SPECIAL RATE
Welcome to the newly renovated, top floor ''Turquoise Cove'' Villa - Makena Surf F301. This amazing property has unsurpassed ocean views, with a unique, double wrap-around lanai, perfect for enjoying tropical sunsets or catching the occasional glimpse of a whale in...
Palms at Wailea 1203, offers the perfect location in Wailea!
Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush landscaping makes this a great Hawaiian retreat!Ideally situated just uphill from gorgeous Keawekapu Beach, The Palms at Wailea is an...
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier
This villa at Ho'olei was renovated in 2024. The renovations are extensive. New extra large kitchen island with ocean view seating: all new appliances in the kitchen: new stone counter tops throughout the home: new cabinets throughout the home: new tile in all the...
Wailea Ekahi Village | 3C
Wailea Ekahi 3C is a captivating vacation rental that offers a truly idyllic island getaway in the heart of Maui's picturesque Wailea resort area. Nestled within the lush, meticulously-maintained 34 acre Ekahi Village complex, this spacious one-bedroom, one-bathroom...
Modern and Luxurious Beachfront Property at Polo Beach
Maui beachfront elegance Polo Beach Club is conveniently situated at the beginning of Makena and the Wailea oceanfront pathway that connects the luxurious Makena and Wailea Resorts. The interior is open, light and bright, fully furnished with creative flair and luxury....
Wailea Ekahi Village | 3E
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo offers elevated views over the tropical grounds lush with colorful island landscaping.The vaulted ceilings and oversized...
Wailea Ekahi Village | 35D
Make your Maui dreams come true at Wailea Ekahi 35D! This vacation rental is perched on the top floor with a private entrance surrounded by manicured grass lawns, colorful bougainvillea, and fragrant plumeria trees.This modern remodeled one-bedroom one-bathroom condo...
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
Wailea Ekahi #14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home! You will feel like you are on top of the world as you look out from the second floor onto the Greenbelt and over...
Wailea Beach Villas | PH210
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
Wailea Ekahi Village | 4D
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit offers an elevated retreat with a bird's eye view of the surrounding tropical landscaping and peek-a-boo ocean views.The 600-square-foot condo is more...
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with...
Wailea Ekahi Village | 7B
Wailea Ekahi 7B is a beautifully appointed vacation rental located within the serene Wailea Ekahi Village. This spacious one-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury.The interior of Wailea Ekahi 7B features a contemporary design with...
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with the best of everything Maui has to offer: spectacular views, privacy and a short stroll to the beach and main pool.With...
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
Beachfront Wailea: Ocean Panoramic & Outer Island Views, Penthouse K-208, 4 Full Bedrooms & 3 Full Baths; Total 3892 S.F. READ ALL OUR REVIEWS for YOUR BEST INSIGHTS, PLEASE.The Wailea Beach Villas Finest Upgrades. Complete Renovation. Contemporary Sleeps Comfortably up...
Wailea Ekahi Village | 11C
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a private lanai and en suite bathroom. Many guests return to this condo year after year for its close proximity to the pool...
Palms at Wailea Villa 806 Ocean View 2BD 2BA
- 2nd floor, walk-up unit- Renovated Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- Guest bedroom with 1 queen bed- Queen sofa bed...
Captivating Ocean Views from Polo Beach Club 805! Direct beach access.
Captivating Ocean Views from Polo Beach Club 805! Direct ocean front location with beach access.You will marvel at the exquisite furnishings and decor at Polo Beach Club 805.As you enter, you are greeted by the sophisticated style of this beautiful ocean front condo.The...
Wailea Beach Villas | PH306
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean Views
This property is hotel zoned, and not being affected by the recent proposed legislation.Luxury at its finest! Ho'olei Villa 17-1! Mesmerizing ocean views and bright open floor plan welcome you. Enjoy the beautiful Maui sunsets on your expansive private lanai.One of the...
Wailea Ekahi Village | 38B
Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start your morning on the lanai with a freshly brewed cup of coffee and walk out on the sprawling grass lawn to feel the soft grass beneath your toes. Take in...
Wailea Ekahi Village | 19B
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired décor, creating a cozy and inviting atmosphere perfect for families or...
Spectacular Views and Prime Location! Oceanfront at Great Rates! Polo Beach 502
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, uncrowded beach right out front, or sit poolside at the newly remodeled pool and jacuzzi! After soaking up the sun all day, plan...
Incredibly Large Polynesian Style Villa in Wailea
Spend your vacation in this villa like Polynesian style vacation rental located at the beautiful Palms at Wailea Resort on the Maui's prestigious southern coast. The central air conditioned 1,515 Sq Ft spacious two bedroom, two and a half bath unit is the dream Hawaii...
WAILEA 10% disc 7+nts thru Summer Full AC Lg Lanai Salt H2O Pool & Walk to Beach
SUMMER is here...make your plans now.NOTE: September 16-19th POOL CLOSED for annual maintenance and repairs. Discounted rates for those dates.Great value for The Palms at Wailea #207 Resort located in Wailea, Maui, HI.Couples escape, Honeymooners, Seniors, Work-cation,...
Palms At Wailea 2002- RARE FIND - Multi Level townhouse in Wailea!
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 view lanai. The spacious living area can easily accommodate a family get together with the entertainment area and...
Wailea Elua Top Floor 2 Bdrm/2 Bath Oceanview Unit - 1 min walk to Ulua Beach
Roomy and relaxing top floor 2 bedroom + 2 full bathroom vacation condominium steps to the beach and pools with convenient parking. Recent upgrades make this a welcome vacation-home where, island time passes slowly, and you can enjoy time on the spacious lanai or take a...
Wailea Ekolu Oceanview 2B/2B ocean view, ground floor unit, corner unit
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 on the ground floor, it is surrounded by grass and lush island foliage. The condo accommodates four people comfortably....
Wailea Hoolei 93-3 Rarely Priced for Last Minute May Getaway at Luxurious Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Ho‘olei 93-3, a lavish 3-bedroom, 3.5-bath villa nestled in the private, gated enclave of Ho‘olei, just a short stroll...
Ocean View Townhouse, Two Story, Central Air, Free Internet, & Washer & Dryer
Wailea Ekolu Village 410Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this light and airy end-unit two-story townhouse situated right next to the Wailea Blue (Ol'...
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private Lanai
Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your visit. Two master suites with king-size beds plus one queen-size sleeper sofa, air conditioning throughout, tastefully...
1A Newly renovated w/porcelain tile floors, custom cabinets, granite countertops
Unit 1A is located on beautiful Keawakapu Beach in gorgeous Wailea. This recently major renovated lower village, ground floor unit has two lanais; one off of the living room with a partial ocean view and one off the bedroom that is tropically landscaped. It is located...
Wailea Hoolei 23-3 Your Perfect Relaxing Getaway at the Ultimate Luxury 3Bedroom
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Ho‘olei Residence 23-3 (L3), a show-stopping 3-bedroom, 3.5-bath villa set within Wailea’s coveted, gated Ho‘olei...
Makena Surf | F112 | Beachfront Resort
Makena Surf F112 is a stunning oceanfront vacation home that offers unparalleled views of the sea from both the spacious living area and the expansive wrap-around lanai that allows for Hawaiian style indoor - outdoor living. By opening the sliding doors, guests can...
1 BR Treetop Wailea , 2nd floor vaulted ceilings
The Tree Top One Bedroom, is an elegant, bright 2nd floor unit with tropical modern king bedroom, teak and rattan furnishings, spacious bath with separate shower and tub, spacious living/dining area and well stocked kitchen and offers privacy amid tree top blooms and...
Fresh and New Luxury Elua Village 2 Bdrm+2 Bath Paradise Condominium #907
**Note to valued guests: Unfortunately, Unit 906 at Elua Village is being remodeled over the summer and fall of 2025. 906 is across the walkway and upstairs from unit 907. There will be construction noise during the day on weekdays. No work will be performed on weekends...
COMPLETELY REMODELED-AC THROUGHOUT-GROUND FLOOR-METICULOUS CLEANING
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, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and...
Wailea Ekolu Village | 910
Discover the perfect Hawaiian retreat at Wailea Ekolu Village with this stunning two-bedroom, two-bathroom ocean view rental. This premium condo offers breathtaking views of the Pacific Ocean, Kaho'olawe, and Molokini from its private lanai. Ideal for families or small...
REMODELED-LARGE LANAI-RESORT LIVING-AC-OCEAN VIEWS-METICULOUS CLEANING
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 specializes in vacation rentals. We are located within a mile of the resort and available 24/7. We are committed to provide our...
Wailea Beach Villas | PH302
Wailea Beach Villas Penthouse #302, with breathtaking views of the pristine Pacific Ocean, awaits. Take joy in the comfort of luxury and tranquility as it seamlessly infuses with lush tropical surroundings creating long lasting memories. Impeccable contemporary finishes...
Luxe Wailea Condo w/ King Suite & Limited Offer: Book 28+ Days for 15% Off + CF
Special Promotions – Limited Time OffersStay Longer and Save MoreBook a stay of 28 nights or more and receive a 15% discount plus waived cleaning fees.Valid for stays between January 4 – December 15.Please mention this offer when booking your long-term stay.Stay 5...
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Enjoy the exclusive Wailea lifestyle in this fashionably decorated, high-end suite with incredible ocean views!!!---This gorgeous, bright and spacious 1-bedroom, 2-bathroom top floor unit offers unmatched views of the ocean and the scenic Wailea greenbelt area. This...
Luxurious villa with high-end finishes, AC, and a large private lanai.
Some of the features include: Travertine Tile, Granite, Marble, Top of the line Stainless Steel Appliances, Mahogany Cabinets, Luxury, Quality Furniture, Plush Carpeting, Air Conditioners in all rooms, and Mirrors throughout. This is truly a perfect getaway!This...
Wailea Beach Villas | PH301
Wailea Beach Villas Penthouse 301 offers an unparalleled vacation experience with its luxurious 2,500 square foot ocean view suite. Situated on the third floor and accessible via a private elevator, this penthouse ensures privacy and tranquility. The suite features...
TOP FLOOR CORNER PRIVATE STUDIO, AFFORDABLE WAILEA, WALK TO BEACH
Last minute DISCOUNTED RATES We appreciate your support as a small, self managed Maui family owned rental instead of renting from a large mainland management company. Enjoy sunny South Maui in our lovely studio top floor condo at the award-winning Grand Champions...
Spacious Wailea Townhouse + Ocean Views! Ekahi 48A
Welcome to Wailea Ekahi 48A, offering the largest floor plan with gorgeous ocean view! This beautiful 2 bedroom/2.5 bath is the perfect retreat for couples or families. The first level of this spacious condo features a sunken living room complete with convertible queen...
Wailea Ekahi 31B, 1 BR/2BA, Lower Greenbelt, Ocean View
Please read under Rules & policies-Rental Agreement the new COVID-19 Rules & Guidelines- and the Waiver of Liability Agreement that must be signed upon arrival.Welcome to our remodeled and reconfigured ground level 1 bedroom, 2 full bathrooms luxury condominium...
Ultimate Luxury: Chef's Kitchen, Soaking Tub, & Private Lanai in Stunning Villa!
Stay longer, enjoy more! Book 10+ nights and receive a free mid-stay clean. Book 14+ nights and get one night free!This property is hotel zoned, and not being affected by the recent proposed legislation.Enjoy your perfect Maui getaway in this spacious and gorgeous...
HO'OLEI #93-2-BEAUTIFULLY APPOINTED VILLA-SLEEPS 8-METICULOUS CLEANING
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 House Offers Tremendous Vacation Experience With It's Amenities, Location, And Level Of Finishes. It Is Managed By PMI...
Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa
Bldg. - 6 - Unit#54 - New Furniture! New personal amenities! new soft goods! An impeccable 1 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South...
Treetop Studio 2nd floor, corner unit
This studio offers private lanai and kitchenette with sink, full size fridge and microwave. King size bed, and remodeled bathroom with walk-in shower. This is a corner unit and is quiet with no roads nearby. * Ideal for those who want to have breakfast and/or lunch at...