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.

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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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 7
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

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....

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 2
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 0 Bathrooms
👤 Sleeps 5
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, 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,...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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....

🛏 2 Bedrooms
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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'...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Wailea, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 10
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

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