Large group vacation rentals in Wailea, HI

Explore 963 large group vacation rentals, homes, and villas in Wailea, HI for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes, Homes with Pools and Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $96 per night and homes offering up to 12 bedrooms and 12 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

963 Great for Groups in Wailea

Wailea Beach Villa H202

Wailea, HI, US
2 Bedrooms 6 Guests
Aug 26 - 29
$1,148 night

Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the best on Maui! Stay 5 Nights, Get 1 Free – More Time to Relax Enjoy an extra night on us! Book 5 consecutive nights, and we’ll give you the 6th night free—a perfect way to extend your getaway without extra cost. Limited availability: This offer is not valid during peak travel times. Blackout dates: November 22–30 & December 20–April 20. How to book: Available exclusively for direct bookings through our website or by phone. This property is hotel zoned, and not being affected by the recent proposed legislation. Located in the highly sought after Wailea Beach Villas, this exquisite penthouse unit offers a lush tropical setting with views of the Pacific Ocean from the entire living area as well as your private lanai! This spacious Penthouse features a fully equipped kitchen ready to entertain. Offering two Sub Zero fridges, granite counters and beautiful mahogany cabinetry, it becomes a gathering place with bar stool seating and plenty of counter space. This open floor plan offers a dining area with seating for 6 and an expansive living room off the kitchen so the whole family can be together. Living area features large Smart TV and added pull out sleeper sofa. Bonus den space off of the kitchen and living area could be used as an additional sleeping area thanks to the comfy sleeper sofa and separate space with sliding doors and shutters for privacy. The living area seamlessly flows out to the lanai through the floor-to-ceiling glass sliders where you can utilize your own private gas grill. Enjoy the serene primary bedroom boasting a large en-suite primary bath with double vanity, deep soaking tub, marble shower, private bathroom, and spacious walk-in closet with personal sized safe. The second bedroom features 2 twin beds that can be converted into a comfortable King bed upon request. Large full bath with tub/shower combo and dual sink vanity just off the entry. Amenities include flat screen televisions in the main living room and both bedrooms, concierge services, valet parking, assigned self-parking, washer/dryer in unit, beach wagon, fitness center, two pools with spas, and complimentary beach set-up. Beachfront infinity pool and spa area are reserved for adults only. Family pool and fitness center are conveniently located right outside of the penthouse building. Beachside or in unit massage available by appointment, business center with internet and printer, restaurant delivery service, (additional fees may apply), lounges and conference room for private events, (additional fees apply), free secure Wi-Fi connection! Gated property ensures privacy and security. Wailea Beach Villas is the only resort on Wailea Beach that is directly adjacent to The Shops at Wailea. This exclusive mall features designer shops and fabulous restaurants, coffee shops, ice cream parlor and The Island Gourmet Market and grocery all within a stone’s throw! Please note per Wailea Beach Villa’s policies, guests are limited to parking one vehicle on property and may request a second vehicle permit on an as needed basis. Visitor(s) will be either assigned a second space or be required to park in the surface spaces (32) located at the entrance to the Hotel. Any additional vehicles may be required to park off site or be charged a daily fee of $50 per vehicle (based on availability). While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating and sleeping space will remain the same or may improve. Hawaii State Tax ID#: 099-786-9056-01

WAILEA ELUA, #2501

Kihei, HI, US
2 Bedrooms 6 Guests
Aug 26 - 31
$722 night

Wailea Elua #2501 – Ground Floor Elegance with Ocean Views and a Completely Upgraded Interior Welcome to Wailea Elua #2501, a stunning ground-floor 2-bedroom, 2-bathroom condo featuring a fully upgraded interior, ocean views, and spacious accommodations for up to six guests. Located in the heart of one of Wailea’s most exclusive beachfront communities, this beautifully renovated retreat offers seamless indoor-outdoor living and easy access to Ulua Beach, the coastal walking path, and all the best of Wailea. Key Features: • Ocean view 2-bedroom, 2-bathroom ground-floor layout • Sleeps up to 6 guests • Primary bedroom with king bed and luxury linens • Guest bedroom with two twin beds • Convertible sofa bed in the living room • Central air conditioner • Completely upgraded interior • Complimentary high-speed wireless internet • Free Long Distance US/Canada • Private lanai with ocean views • Washer and dryer in unit • Beach towels and beach chairs provided Interior Amenities: • Stylish, fully remodeled kitchen with modern appliances • Open-concept living and dining area with ocean views • Elegant island-inspired decor and comfortable furnishings • Flexible sleeping options ideal for families or small groups Housekeeping Services: Traditional housekeeping service is provided every 3rd day. This includes refreshing the condo and exchanging bed linens, bath towels, and amenities. Housekeeping services are scheduled between 8:30 a.m. and 4:30 p.m. Wailea Elua Village Amenities: • Gated beachfront community with 24 acres of tropical landscaping • Direct access to Ulua Beach – ideal for snorkeling, swimming, and seasonal whale watching • Two saline swimming pools and Jacuzzi • Beachfront pavilion with BBQs and outdoor dining • Fitness center and pickleball court • Free private on-site parking • Access to Wailea’s coastal walking path Nearby Attractions: • Ulua Beach and the Wailea Beach Path • The Shops at Wailea – fine dining, boutiques, and art galleries • Wailea’s championship golf courses and tennis center • Paddleboarding, snorkeling tours, and whale watching in season Additional Perks: • 24-hour emergency assistance • Complimentary concierge services • Return guest program • Thoroughly cleaned and sanitized—ask about our AlohaSafeStay program • Personalized Aloha Greeting upon arrival Our commitment to providing an elevated guest experience includes: • Arrival with Aloha: Enjoy hassle-free, in-person guest check-in at your condo. • Professional Cleanliness: Our in-house housekeeping teams are VRHP (Vacation Rental Housekeeping Professionals) trained and use industry-leading practices. • Responsive Guest Support: Our on-island guest service team is just a call or text away, ready to respond promptly to any needs. • Reliable Maintenance: Should an issue arise, our dedicated maintenance partners can quickly address the matter. • Luxury Amenities: Experience superior bedding, linens, towels, and bath products that reflect the standards of a luxury property. • Expert Concierge Services: Our on-island concierge team is available to assist with personalized recommendations and bookings for local activities and experiences. Minimum stay requirement of 14 nights may apply for holiday (Christmas/New Years) periods. Book with confidence – This condo is located in a hotel/resort-zoned property and is not affected by Maui County’s Bill 9 vacation rental restrictions. TA-029-020-2624-02 GE-029-020-2624-02 ​​​​​​​​​​​​​​TMK-210080700065

WAILEA ELUA, #1503

Wailea, Maui, HI, US
2 Bedrooms 5 Guests
Aug 30 - Sep 4
$636 night

Wailea Elua #1503 – Panoramic Lanai Views Near Pool & Paddle Court Escape to the beauty of Wailea with a stay at Wailea Elua #1503, a spacious 2-bedroom, 2-bathroom condo offering panoramic views from the private lanai and a serene setting within one of South Maui’s most desirable beachfront communities. With elegant furnishings, modern comforts, and a location just steps from the pool and paddle ball court, this unit is perfect for families or couples looking to relax in style. Condo Features: •2-bedroom, 2-bathroom condo •Sleeps up to 5 guests •Primary Bedroom: King bed with luxury linens •Guest Bedroom: Two twin beds •Central air conditioner •Panoramic lanai views with outdoor seating •Complimentary high-speed wireless internet •Free Long Distance US/Canada •Beach towels and beach chairs provided Interior Amenities: •Fully equipped kitchen with modern appliances •Spacious open-concept living and dining area •Private lanai perfect for enjoying Maui’s sunsets and breezes •Master bathroom includes a bathtub for added comfort •In-unit washer and dryer •Cable television and free local phone service Housekeeping Services: Traditional housekeeping service is provided every 3rd day for qualifying stays. This includes refreshing the condo and exchanging bed linens, bath towels, and amenities. Services are available between 8:30 a.m. and 4:30 p.m. Wailea Elua Village Amenities: •Gated beachfront community spanning 24 acres of tropical gardens •Direct access to Ulua Beach – ideal for snorkeling, swimming, and seasonal whale watching •Two saline swimming pools and Jacuzzi •Beachfront pavilion with barbecue stations •Pickleball court •Free private on-site parking •Convenient access to Wailea’s scenic oceanfront walking path Nearby Attractions: •Ulua Beach and the Wailea Beach Walk •The Shops at Wailea – upscale shopping and dining •Championship Wailea Golf Courses and Tennis Club •Local snorkeling tours, paddleboard rentals, and ocean adventures Additional Perks: •24-hour emergency assistance •Complimentary concierge services •Return guest program •Thoroughly cleaned and sanitized—ask about our AlohaSafeStay program •Personalized Aloha Greeting upon arrival Our commitment to providing an elevated guest experience includes: •Arrival with Aloha: Enjoy hassle-free, in-person guest check-in at your condo. •Professional Cleanliness: Our in-house housekeeping teams are VRHP (Vacation Rental Housekeeping Professionals) trained and use industry-leading practices. •Responsive Guest Support: Our on-island guest service team is just a call or text away, ready to respond promptly to any needs. •Reliable Maintenance: Should an issue arise, our dedicated maintenance partners can quickly address the matter. •Luxury Amenities: Experience superior bedding, linens, towels, and bath products that reflect the standards of a luxury property. •Expert Concierge Services: Our on-island concierge team is available to assist with personalized recommendations and bookings for local activities and experiences. Minimum stay requirement of 14 nights may apply for holiday (Christmas/New Years) periods. Book with confidence – This condo is located in a hotel/resort-zoned property and is not affected by Maui County’s Bill 9 vacation rental restrictions. TA-143-749-7344-02 GE-143-749-7344-02 ​​​​​​​TMK-210080700003

Grand Champions 139

Wailea, HI, US
2 Bedrooms 4 Guests
Aug 31 - Sep 2
$211 night

Incredible Renovation! Kick back and relax on your own private lanai and take in wonderful garden views, with some ocean and mountain views. Feel the wonderful trade winds and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This spacious two-bedroom unit in the Grand Champions Villas comes fully stocked with all the amenities needed to make you feel as if you are in your own home. The Primary bedroom features a king bed and an ensuite with an amazing walk-in shower! The secondary bedroom has two twin beds that can be converted into a king bed upon request and an ensuite bathroom. Ground floor access makes trips to and from the beach, golf course, tennis courts, and pool a breeze! Location! Location! Location! The Grand Champions have lush beautiful landscaping and amenities include two pools, Jacuzzi, BBQ, and Security. This central Wailea location makes it favorable as you can walk to tennis, Shops at Wailea, casual to fine restaurants, world’s top beaches, and five-star hotels. Parking available on property While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve. *Window A/C in Bedrooms Only* Update 5/22: Dryer Vent Cleaning taking place between 8/3-8/13. Hawaii Tax ID #: 056-304-4352-02

Grand Champions Golf Villas 150

Wailea, HI, US
2 Bedrooms 6 Guests
Aug 26 - 31
$378 night

Note: Roof replacement at Grand Champion Golf Villas will be happening over the next year. There will be equipment and contractors working at the property daily. This building’s roof has already been completed. Unit #150 - An impeccable 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that Wailea Grand Champion Golf Villas has to offer in a 2 bdrm + 2 bath category. Upgraded in every way with split A/C systems, a superb kitchen and fantastic sunset views across the Wailea Ol’ Blue Golf Course toward the West Maui mountains. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South Maui, nestled between the championship Ol’ Blue Golf Course and the award winning Wailea Tennis Center. Lush tropical gardens and swaying palm trees surround all 188 units, two swimming pools, two Jacuzzis and four gas BBQ grills to enjoy. Shopping, dining, activities, and amenities are conveniently located within walking distance. Beautiful Wailea beaches are just a short drive away or a 15–20-minute walk from the Villas. Wailea Grand Champions Golf Villas offers great values and views in the heart of the upscale Wailea Resort community. This moderately priced, luxury property is in the center of Wailea’s Ol’ Blue Golf Course, with contemporary villas featuring private lanais for sunset views over the fairways to the West Maui mountains. Wailea area resorts, spa facilities, and award-winning restaurants are within walking distance, and Wailea’s fabulous beaches are a leisurely 15-minute walk or easy 3-minute drive from the Wailea Grand Champions Villas. Wailea Gateway Center, Wailea Town Center, The Shops at Wailea, and the newest shopping/entertainment destination Wailea Village Center are all a few minutes’ walk from your vacation home at Wailea Grand Champions. Beach chairs, beach towels and coolers are provided. Additional beach gear may be rented at one of our local beach shops.

Grand Champions | Ocean View 1 BR Sleeps 4 | 181

Wailea-Makena, HI, US
1 Bedrooms 4 Guests
Aug 26 - 28
$256 night

NEW Renovated 1-bedroom, 2-bath villa at Grand Champions Resort with ocean views, pools, tennis, shopping, and dining. Perfect Maui retreat. ** 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 and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and drop-off is included and you’ll only be responsible for a $15/day airport tax. Upgrades to larger vehicles are available upon request.Please note: Holiday periods may result in limited rental car availability. We recommend booking as early as possible. Welcome to Grand Champion Villa 181, a beautifully renovated one-bedroom, two-bath vacation condo located in the heart of Wailea, Maui’s premier resort destination. This ground-floor villa offers 1,056 square feet of island-inspired comfort and garden views, ideal for a romantic escape or a relaxing retreat for up to four guests. The spacious primary suite features a brand-new Stearns and Foster king bed, a flat-screen TV, ceiling fan, and an en-suite bathroom with a walk-in shower. A second full bathroom adds extra convenience, and the plush sleeper sofa in the living room offers additional sleeping space for kids or friends. Thoughtfully designed with an open floor plan and tropical decor, the living area invites you to unwind in style after a day in the sun. The fully equipped kitchen includes a stove, oven, refrigerator, microwave, and dishwasher, along with must-haves like a coffee maker, blender, rice cooker, and toaster. Whether you’re whipping up a quick breakfast or a full dinner, you’ll have everything you need. Enjoy meals at the indoor dining table or step out to your private lanai for alfresco dining surrounded by lush greenery and fresh Maui air. For comfort and convenience, the condo also includes high-speed Wi-Fi, cable TV, air conditioning, and in-unit laundry. Everything you need for a carefree stay is right here. Located within the Wailea Grand Champions Villas, this property is nestled between the Wailea Blue Golf Course and the Wailea Tennis Club, making it a prime choice for golf and tennis lovers. You’ll be just minutes from world-class beaches, luxury resorts like the Grand Wailea and Four Seasons, award-winning restaurants, boutique shopping, and scenic coastal walks along the Wailea Beach Path. Whether you’re snorkeling at Molokini Crater, catching a sunset at Wailea Beach, or simply lounging poolside with a cocktail, Grand Champion Villa 181 is the perfect home base for your unforgettable Maui vacation. Grand Champions features a convenient location directly across the street from shopping, and it’s close to the beach. It wraps around the popular Wailea Blue course, and is adjacent to the Wailea Tennis Club. Walking distance to several restaurants. For a seamless booking experience, your total reservation price includes a damage waiver, so there’s no need to collect a separate security deposit. Finally, Grand Champions is situated in a hotel-zoned area designated for tourism, ensuring your reservation is secure from any future luxurious getaway rental restrictions enacted in Maui. 24/7 Onsite Support | Need assistance during your stay? KBM Resorts provides local, around-the-clock support with an average onsite response time of 10 minutes or less, stocked with over 750 items to quickly handle any issue. Licence number: TA-172-475-8528-01

WAILEA EKOLU, #914

Wailea, Maui, HI, US
2 Bedrooms 5 Guests
Aug 27 - 29
$838 night

Wailea Ekolu #914 Welcome to Wailea Ekolu #914, a rare and fully upgraded two-story townhouse offering breathtaking 180-degree ocean views in one of the most peaceful and private settings within Wailea Ekolu Village. This spacious two-bedroom, two- bathroom vacation home features over 1,900 square feet of interior space, modern comforts, and direct access to world-class beaches, shops, and restaurants—perfect for a relaxing Maui escape. Key Features: •2-bedroom, 2-bathroom split-level townhouse •Primary bedroom with king bed •Guest bedroom with two queen beds •Split-duct air conditioning throughout •Vaulted ceilings and upgraded interior finishes •Approx. 1,900 square feet of living space •Private lanai with teak dining table and panoramic ocean views •Fully equipped kitchen •Washer & dryer in unit •Cable television, complimentary high-speed Wi-Fi, and internet access •Free local phone service Wailea Ekolu Village Amenities: •Two swimming pools •Outdoor barbecue areas •Free on-site parking •Lush tropical landscaping •Walkable access to Wailea Beach, golf, dining, and shopping Interior Amenities: •Open-concept living and dining area with expansive views •Secluded location near pool •Ideal for families or couples with ample space to relax and gather Housekeeping Services: Available for purchase Wailea Ekolu #914 is a rare gem that combines space, comfort, and privacy with unbeatable access to everything Wailea has to offer. Our commitment to providing an elevated guest experience includes: •Arrival with Aloha: Enjoy hassle-free, in-person guest check-in at your condo. •Professional Cleanliness: Our in-house housekeeping teams are VRHP (Vacation Rental Housekeeping Professionals) trained and use industry-leading practices. •Responsive Guest Support: Our on-island guest service team is just a call or text away, ready to respond promptly to any needs. •Reliable Maintenance: Should an issue arise, our dedicated maintenance partners can quickly address the matter. •Luxury Amenities: Experience superior bedding, linens, towels, and bath products that reflect the standards of a luxury property. •Expert Concierge Services: Our on-island concierge team is available to assist with personalized recommendations and bookings for local activities and experiences. **Minimum stay requirement of 14 nights may apply for holiday (Christmas/New Year) periods.** Book with confidence: All reservations currently being accepted are not to be impacted by Bill 9. TA-079-030-4768-02 GE-079-030-4768-02 ​​​​​​​TMK-210080770085

WAILEA ELUA, #2201*^

Wailea, Maui, HI, US
2 Bedrooms 6 Guests
Aug 26 - 31
$660 night

Wailea Elua #2201 – Spacious Island Comfort with Partial Ocean Views Welcome to Wailea Elua Village #2201, a beautifully upgraded ground-floor condo nestled within one of Wailea’s most exclusive beachfront communities. This spacious two-bedroom, two-bathroom retreat combines island-inspired comfort with modern luxury, making it the perfect home base for your Maui vacation. Located on the garden side of the property, this unit offers a peaceful atmosphere with partial ocean views and convenient access to Ulua Beach and the Wailea Beach Walk. Condo Features: •Convenient Ground Floor Entry •Completely Upgraded Interior •King Bed in Primary Bedroom •Two Twin Beds in Guestroom (can be converted to a king upon request) •Convertible Sofa Bed in Living Room •Central Air Conditioning •Complimentary High-Speed Wireless Internet •Fully Equipped Kitchen with Granite Counters and New Stainless Steel Appliances •In-Unit Washer & Dryer •Cable TV and Free Local Phone Service •Private Lanai with Garden and Partial Ocean Views •Free Long Distance US/Canada •Sleeps up to 6 Guests Wailea Elua Village Amenities: •Two Swimming Pools •Jacuzzi •Beachfront Pavilion with Barbecue Stations •Pickleball Court •Free Private Parking •Easy Access to the Wailea Coastal Walk •Steps from World-Class Shopping, Dining, and Golf Housekeeping Services: Traditional housekeeping is provided every third day. This includes refreshing the condo and exchanging bed linens, bath towels, and amenities. Services are scheduled between 8:00 a.m. and 4:30 p.m. A Note from the Owner: We enjoy spending time out on the lanai, which has a large grassy area behind it that is great for our grandchildren to play ball on. Ulua Beach is just a short walk and it’s great for paddle boarding, boogie boarding, and snorkeling. The Shops at Wailea are also just a short walk from the condo and they have a variety of stores as well as restaurants. The kitchen has granite counters and new stainless steel appliances and is well stocked if you want to cook at home. We have convenient parking directly in front of our unit and only two stairs to get inside. The condo interior is all on one level. Our unit is on one end of the complex, next to a wooded area and is very private. Nearby Attractions: •Ulua Beach •The Shops at Wailea •Wailea Golf Club •Wailea Tennis Club •Mokapu Beach Park •Fine Dining at Nearby Resorts •Seasonal Whale Watching (December–April) Our commitment to providing an elevated guest experience includes: •Arrival with Aloha:Enjoy hassle-free, in-person guest check-in at your condo. •Professional Cleanliness:Our in-house housekeeping teams are VRHP (Vacation Rental Housekeeping Professionals) trained and use industry-leading practices. •Responsive Guest Support:Our on-island guest service team is just a call or text away, ready to respond promptly to any needs. •Reliable Maintenance:Should an issue arise, our dedicated maintenance partners can quickly address the matter. •Luxury Amenities:Experience superior bedding, linens, towels, and bath products that reflect the standards of a luxury property. •Expert Concierge Services:Our on-island concierge team is available to assist with personalized recommendations and bookings for local activities and experiences. Minimum stay requirement of 14 nights may apply for holiday (Christmas/New Years) periods. Book with confidence – This condo is located in a hotel/resort-zoned property and is not affected by Maui County’s Bill 9 vacation rental restrictions. TA-134-609-3056-01 GE-134-609-3056-01 ​​​​​​​​​​​​​​TMK-210080700053

WAILEA GRAND CHAMPION, #142

Wailea-Makena, HI, US
1 Bedrooms 4 Guests
Aug 26 - 28
$438 night

Wailea Grand Champions #142- Garden View Comfort in the Heart of Wailea Welcome to Wailea Grand Champions #142, a beautifully maintained one-bedroom, two-bathroom villa set among lush tropical gardens and offering a peaceful retreat in one of Maui’s most sought-after resort communities. Located between the Wailea Blue Golf Course and Wailea Tennis Club, and just a short stroll from beaches and shopping, this condo combines comfort, privacy, and resort convenience for a truly memorable Maui escape. Key Features: •1-bedroom, 2-bathroom layout •Primary bedroom with king bed, ceiling fan, Smart TV, and en suite bathroom •Queen-size sofa sleeper in the living room •Fully equipped kitchen with modern appliances and ample counter space •Individually controlled air conditioning throughout •Cable television and complimentary high-speed internet •Washer and dryer in unit •Private lanai with tropical garden views •Luxury linens provided Wailea Grand Champions Amenities: •Two pool areas with Jacuzzis •Outdoor barbecue stations •Free on-site parking •Beautifully landscaped tropical grounds •Quiet, low-density community ideal for relaxation Interior Amenities: •Open-concept living and dining area •Tastefully furnished for comfort and functionality •Perfect for couples or small families Housekeeping Services: Available for purchase Nearby Attractions: •Wailea Beach, Ulua Beach, and Mokapu Beach •The Shops at Wailea – boutique shopping, casual and fine dining •Wailea Blue, Gold, and Emerald Golf Courses •Wailea Tennis Club – located next to the property •Wailea Beach Path – ideal for scenic sunrise and sunset walks •Snorkeling, paddleboarding, and seasonal whale watching nearby Additional Perks: •24-hour emergency assistance •Complimentary concierge services •Departure cleaning included •Return guest program •Thoroughly cleaned and sanitized—ask about our AlohaSafeStay program •Personalized Aloha Greeting upon arrival Our commitment to providing an elevated guest experience includes: •Arrival with Aloha: Enjoy hassle-free, in-person guest check-in at your condo. •Professional Cleanliness: Our in-house housekeeping teams are VRHP (Vacation Rental Housekeeping Professionals) trained and use industry-leading practices. •Responsive Guest Support: Our on-island guest service team is just a call or text away, ready to respond promptly to any needs. •Reliable Maintenance: Should an issue arise, our dedicated maintenance partners can quickly address the matter. •Luxury Amenities: Experience superior bedding, linens, towels, and bath products that reflect the standards of a luxury property. •Expert Concierge Services: Our on-island concierge team is available to assist with personalized recommendations and bookings for local activities and experiences. **Minimum stay requirement of 10 nights may apply for holiday (Christmas/New Years) periods.** Book with confidence: All reservations currently being accepted are not to be impacted by Bill 9. TA-149-116-2624-01 GE-149-116-2624-01 TMK-210081040142

Wailea Beach Villa B102

Wailea, HI, US
3 Bedrooms 8 Guests
Aug 26 - 31
$3,506 night

Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the best on Maui! This property is hotel zoned, and not being affected by the recent proposed legislation. Welcome to the prestigious oceanfront Wailea Beach Villa B102. This 3 bedroom/3.5 bath is desirably located just steps from the adult infinity edge pool and stunning Wailea Beach. With breathtaking ocean views and close proximity to the beach, this beautifully designed beachfront villa is exactly what dream vacations are made of! Enticing, spacious ground floor location boasts over 3000 sqft of open living space. As you enter this luxurious villa, note the sizable gourmet kitchen, dining area, contemporary Hawaiian designed living room and grand lanai with gas grill. Many high-end, Smart Home features including a whole-house Lutron lighting system, Universal Remotes for simplified TV control, easy to use AC remotes, high-speed internet with Wifi covering entire interior and lanai, and a whole-house Sonos audio system with speakers and audio control in each room. Connect your cell phone to the password protected WIFI system, open the Sonos App and play your personal music throughout the home or in selected rooms. Smart TVs give you access to Apple TV, Netflix and Amazon Prime. Recently completely repainted, the interior of this Villa is consistently being upgraded and refreshed. Floor to ceiling glass pocket doors seamlessly blend into one magnificent indoor/outdoor living space. Enjoy al fresco dining then take a dip in your private plunge pool, steps from your lanai. You’ll easily spot whales right out front during whale season, and picturesque sunsets each evening. Your private yard offers a personal sanctuary, while being steps to the sand! This exquisite villa offers two primary bedrooms and an additional guest room. The Ocean Primary, just off the kitchen, features sliding lanai doors allowing breathtaking ocean views. Complete with a California King bed, en suite bathroom with separate soaking tub & shower and a large walk-in closet. The Garden primary offers a California King bed, en suite bathroom with separate soaking tub and shower, and large walk in closet. Don’t miss the private outdoor shower with direct access to the adult pool. The third bedroom, off of the main entrance is perfect for guests or children with 2 queen beds, walk in closet and adjacent bathroom. All bathrooms are equipped with Toto Washlet Toilets for added comfort. Enjoy all of what Maui is known for such as must-see views of Kaho’olawe, Lanai, and Molokini Crater. Witness Humpback Whales breaching during the season and some of the best snorkeling in the World all conveniently from this spectacular front row, oceanfront villa! The moment you arrive at the lobby, you are greeted by the experienced and personalized service staff. Amenities include concierge services and assigned self-parking. There is an exclusive adult infinity edge pool and spa situated oceanside with private cabanas and easy access to one of the World’s most sought after beaches. Find a recreation/fitness center conveniently situated near the family pool, just below the lobby. Additional amenities include a business center w/ internet and printer, restaurant delivery service & free secure Wi-Fi connection! Gated property ensures privacy and security. Wailea Beach Villas is the only resort on Wailea Beach that is directly adjacent to The Shops of Wailea. This exclusive mall features designer shops & fabulous restaurants, coffee shops, ice cream parlor & The Island Gourmet Market all within a stone’s throw! We offer a complimentary supply refresh every 3 days for this villa. While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve. Hawaii State Tax ID#: 143-563-8272-02

Grand Champions 164

Wailea, HI, US
2 Bedrooms 6 Guests
Sep 1 - 3
$166 night

We love our Peaceful Maui Condo and want to share it with you! Enjoy views of the mountains, ocean, and golf course from our top-floor, vaulted ceiling condo. Our condo comfortably sleeps six and has all the amenities that you need to enjoy your Hawaiian vacation - just bring your suitcases and stop for groceries on the way in! Fully air-conditioned 2 Bedroom suites with king beds in both bedrooms Queen sofa bed in the living room Tempur-Pedic king-size bed in Primary Primary Bath features double sinks and double shower heads in the oversized shower Combo tub/shower in the second bathroom Walk-In Primary closet Quality linens and towels Flat-screen TVs with cable DVD player Iron and ironing board Private washer and dryer Fully stocked kitchen Shampoo, conditioner, body wash, and lotion provided Free Wi-Fi Beach/sand toys, beach chairs, umbrella, ice chests, beach towels Surfing, snorkeling, fishing, biking, zip-lining, whale watching, hiking, and horseback riding are just a few of the many adventures you will find nearby. Walk to the nearby Shops at Wailea for great shopping (Louis Vuitton, Gucci, Tiffany & Co., Prada, Gap, Billabong, BCBG, Banana Republic, Tori Richard, Tommy Bahama, and more). Enjoy casual and fine dining restaurants close by. Some of our favorites: Spago, Tommy Bahama’s Restaurant and Bar, Ruth’s Chris Steak House, Ko, Matteo’s Osteria, Fabiani’s. Amazing Sunsets included at no extra charge! While we strive to keep all photos up to date, there may be new and updated pieces of furniture or decor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve. Update 5/22: Dryer Vent Cleaning taking place between 8/3-8/13. Hawaii Tax ID #: 088-224-9728-01

Hoolei 24-6

Wailea, HI, US
3 Bedrooms 10 Guests
Aug 26 - 29
$956 night

Ho’olei 24-6 | Luxury Wailea Villa | Hotel-Zoned Vacation Rental | Gated Community Near Beach Welcome to Ho’olei 24-6, a premier hotel-zoned luxury villa in Wailea Maui, located within one of South Maui’s most exclusive gated resort communities. This residence is unaffected by proposed short-term rental legislation, offering peace of mind for your Maui vacation planning and investment in a true legal vacation rental in Wailea. This beautifully appointed 3-bedroom, 3.5-bath garden view villa is designed for effortless indoor-outdoor island living. Expansive corner pocket doors fully retract to reveal a spacious, completely private lanai surrounded by lush tropical landscaping. Enjoy outdoor dining in Wailea with a built-in gas grill, gather around the dining table for six, or relax in the shaded open-air lounge with cooling trade winds and ceiling fans creating a serene Hawaiian retreat. Inside, the villa blends modern luxury with island elegance. The open-concept living space features a large, plush sectional, ideal for unwinding after a day at the beach, along with a formal dining area perfect for entertaining. The gourmet kitchen is fully equipped with premium appliances, a breakfast bar, and everything needed for cooking at home. High-speed WiFi and a flat-screen TV provide all the comforts of a luxury Maui vacation rental. The thoughtfully designed layout offers comfort and privacy for families and groups: The primary suite (main level) features a king bed, private sitting area with sleeper sofa, spa-style ensuite with soaking tub, walk-in shower, and its own secluded lanai. A second guest suite (main level) includes two full-size beds and a private ensuite bathroom. The third guest suite (upper level) offers a king bed, ensuite bath, and elegant French doors opening to a charming balcony with tropical views. Additional features include central air conditioning, full-size washer and dryer, private garage, covered carport, and complimentary beach gear including chairs and towels—perfect for days at nearby Wailea Beach. The Ho’olei at Wailea resort community offers exceptional amenities, including a resort-style pool with waterfall, grotto, sandy-bottom keiki area, two hot tubs, fitness center, and open-air gathering spaces. Optional poolside massage services are available for an elevated wellness experience. With 24-hour gated security, guests enjoy both luxury and privacy. Beach access is conveniently located just across the street, where you can explore world-famous Wailea beaches and enjoy nearby fine dining, spa experiences, and oceanfront restaurants. Please note: access to neighboring resort pools is not included. Whether you’re searching for a Wailea luxury villa rental, Maui family vacation home, or a private resort-style getaway near the beach, Ho’olei 24-6 delivers the perfect balance of comfort, location, and elevated island living. Experience the best of Wailea Maui vacation rentals—Ho’olei 24-6 is ready to welcome you. Hawaii State Tax ID: 188-260-1984-01

Hoolei Residences 93-3

Kihei, HI, US
3 Bedrooms 8 Guests
Aug 26 - 30
$942 night

Ho’olei 93-3 Stunning Wailea Luxury Vacation Rental Residence Perfect for Family and Group Travel Welcome to your Maui Retreat: Ho’olei 93-3 is a lavish 3-bedroom, 3.5-bath villa nestled in the private, gated enclave of Ho’olei, just a short stroll from world-famous Wailea Beach and the iconic Grand Wailea Resort. Spanning 2,700 sq ft of interior living and 700 sq ft of covered lanai space, this two-level retreat—complete with private elevator—pairs grand scale with resort-style perks, making it a perfect base for family get-togethers or couples’ escapes. Complimentary Activities, Every Day of Your Stay Every reservation with Maui Paradise Properties includes one free ticket per activity, each day to some of our favorite Maui experiences—plus unbeatable savings on other local favorites! This exclusive benefit is offered in partnership with Xplorie, giving you an easy way to add adventure, relaxation, and local flavor to your stay. *Limit one free ticket per activity, per day, per reservation. Additional tickets available for purchase. Activities offered may vary by home or condo. Activity offer available for stays up to 35 nights. Condo Highlights 3 Bedrooms, 3.5 Bathrooms, Sleeps 6 Guests Central air conditioning throughout Both upper and lower expansive lanais capture pastel dawns and tangerine sunsets over lush palm trees A private elevator and wide interior staircase ensure seamless connection between floors King bed featured in the primary suite (Ground Level) King bed featured in the secondary suite (Ground Level) 2 Queen beds featured in the third suite (Upper Level) Ceiling fans throughout Smart TVs in living room & bedrooms Gourmet Show Kitchen – Granite counters, gas cooktop, custom cabinetry, luxe appliances and an island breakfast bar Interior dining table seating for 8 Breakfast bar seating for 4 Outdoor dining table seating for 6 on the upper lanai for al-fresco meals Comfortable outdoor sofa on the upper level lanai Plush outdoor bistro sofa and chairs set on the lower level lanai Washer & Dryer in-villa Resort Features Gated luxury residence community in Wailea — seamless blend of villa comfort and resort amenities Elevator access, secure gated entry, covered parking garage (one car + extra stall) Lagoon-style pool with waterfall grotto & sand-entry (child-friendly) Two hot tubs Fitness center & sauna Poolside BBQ pavilions Steps or short stroll to Wailea Beach access and The Shops at Wailea Local Area Close to Wailea’s sandy beaches including Ulua Bay for snorkeling and Polo Beach for calm swimming Near The Shops at Wailea for boutiques, dining, and family-friendly spots like Lappert’s Ice Cream Easy access to Wailea’s Blue, Gold, and Emerald Golf Courses and scenic beach paths The Maui Paradise Properties Difference Locally Owned & Operated: Nearly 500 handpicked vacation homes across Maui, managed by our on-island team. Personalized, 24/7 Guest Support: Real people, real help—before, during, and after your stay. Professionally Managed & Safety-Focused: Licensed, responsive, and committed to guest well-being. Free Daily Island Activities: Enjoy exclusive access to complimentary activities and local experiences during your stay. Maui Compliance Details GE: TA-093-298-8416-01 TA: TA-093-298-8416-01 TMK: 210081190039

Hoolei 17-3

Wailea, HI, US
3 Bedrooms 8 Guests
Aug 26 - 29
$1,032 night

This property is hotel zoned, and not being affected by the recent proposed legislation. This villa features a spacious floor plan with sweeping ocean views. Marvel at the beautiful Maui sunsets from your private lanai! Enjoy indoor/outdoor dining with a modern gourmet kitchen and a Wolf gas grill. Relax in your open and inviting living area. With direct access to a private lower lanai from your primary suite, drift off to sleep with the soothing sound of the Pacific Ocean. The primary bedroom is located on the lower level and features a king bed, a large ensuite bathroom with a soaking tub, a walk-in shower, dual vanity sinks, and a walk-in closet. Enjoy your own private ground floor, ocean view, outdoor lanai with lounge chairs! The second primary bedroom is also located downstairs with a king bed and a full ensuite bathroom. The top floor features a guest bedroom with 2 full beds and a private ensuite bathroom. The main living area also offers a half bathroom for guests to use. This two-story townhome also features central air conditioning throughout, a full-sized washer and dryer, a private garage, and a covered carport across the driveway for a second vehicle. Beach chairs and beach towels are provided for use at the beach or at the property pool! Ho’olei property features a stunning pool with a waterfall, grotto, sandy beach area for children, and two jacuzzis to enjoy. Feel free to take the beach towels provided in your unit down to the pool to use! There is a fitness center to use next to the pool area, and a covered kitchen pavilion. Poolside massages are also available! This is a gated community with 24-hour security available. Beach access is located directly across the street through the adjacent resort. You are able to dine at any of the resort’s restaurants, as well as set up spa appointments, but please note that pool access at the adjacent resort is not included with your reservation at this Ho’olei villa. While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve. Hawaii Tax ID: 196-318-6688-01

Wailea Ekahi 36E

Wailea, HI, US
1 Bedrooms 4 Guests
Sep 1 - 3
$153 night

*Wailea Ekahi 36E | Tropical Retreat Near Keawakapu Beach* Escape to Wailea Ekahi 36E, a beautifully appointed one-bedroom, two-bath condo nestled among lush tropical landscaping in the heart of Wailea. Enjoy peaceful garden surroundings, a spacious private lanai, split AC in the bedroom, a fully equipped kitchen, and access to resort-style amenities including four pools, a beachfront pavilion, fitness center, and direct access to Keawakapu Beach. *Condo Features* * 1 Bedroom | 2 Bathrooms * Spacious second-floor condo * King bed in primary bedroom * Split AC in bedroom * Ceiling fan in primary bedroom * Ensuite bathroom with beautifully tiled shower * Second full bathroom with shower * Open-concept living and dining area * Floor-to-ceiling sliding glass doors * Private lanai surrounded by tropical foliage * Indoor and outdoor living experience * Dining table with seating for four * Fully equipped kitchen with cookware and dining essentials * In-unit washer and dryer * Complimentary WiFi **Resort Amenities** * Four swimming pools * Large beachfront pavilion and pool * Direct access to Keawakapu Beach * Community gas grilling area * Newly added fitness center * Beautiful tropical landscaping throughout the property * Easy access to the Wailea Beach Path *Prime Wailea Location* Located in one of Maui’s most sought-after resort communities, Wailea Ekahi places you steps from Keawakapu Beach and minutes from Wailea’s world-famous beaches, championship golf courses, shopping, dining, snorkeling, and outdoor adventures. Stroll the scenic Wailea Beach Path, spend the day at the beach, or enjoy sunset cocktails at nearby oceanfront restaurants. *Fitness Center* * Open daily from 7:00 AM to 10:00 PM * Located near the Beach Pavilion * Cardio equipment * Dumbbells ranging from 1–50 lbs * Additional fitness accessories for full-body workouts * Guests must be 18 years or older * Signed waiver required * Closed-toe athletic shoes required * Swim attire not permitted *Important Notes* * Wailea Ekahi no longer permits private grills on lanais. * Community gas grilling stations are available for guest use. * The Pavilion Pool is anticipated to undergo resurfacing between August 16 and October 16, 2026. Dates are subject to change. * During the Pavilion Pool project, beach access, the fitness center, Pavilion facilities, and the remaining three pools are expected to remain open. * Nearby Unit 36C is scheduled for a kitchen renovation from approximately July 20 through August 30, 2026. Construction noise may be audible during this period. * While we strive to keep all photos up to date, furnishings and décor may vary from those shown. Functionality, available seating, and sleeping accommodations will remain the same or may improve. Registration number: 210080650005 Hawaii State Tax ID: 188-700-9280-01

Palms at Wailea 203

Kihei, HI, US
2 Bedrooms 8 Guests
Aug 26 - 28
$431 night

Experience elevated island living in this exquisitely remodeled 2-bedroom, 2-bathroom residence at the prestigious Palms at Wailea, where refined design meets effortless Maui luxury. This sophisticated retreat showcases a seamless blend of modern elegance and relaxed island comfort, highlighted by a bright, open-concept living space that extends gracefully onto an expansive double wrap-around lanai, perfect for indoor-outdoor living in paradise. The serene primary suite offers a plush king bed and a spa-inspired en-suite bathroom, creating a private sanctuary for rest and relaxation. The guest suite is equally inviting with a king bed and a beautifully appointed full bathroom just steps away. Designed with both style and flexibility in mind, the home also features a premium sleeper sofa and two cleverly integrated twin beds tucked into the dining nook, ideal for accommodating up to eight guests in comfort and sophistication. Stay cool in every season with efficient split AC systems throughout, while the thoughtfully curated interiors reflect a polished yet welcoming aesthetic. Every detail of this renovation has been carefully considered to deliver a luxurious, high-end experience. Condo Features: Smart TV in the living room for elevated entertainment Split (ductless) AC in the living area and both bedrooms Two king beds, plus a sleeper sofa and twin nook beds for flexible accommodations Two fully remodeled bathrooms with designer walk-in tiled showers Indoor dining for 4, plus an inviting lanai with seating for 6 and a comfortable lounge area Fully equipped gourmet kitchen with full-size appliances (refrigerator with ice maker, stove, oven, microwave, dishwasher) Premium small appliances including coffee maker, grinder, blender, toaster, and rice cooker Complete set of plateware, glassware, cookware, and utensils Added Luxuries: Beach chairs for your seaside excursions In-unit washer and dryer Complimentary WiFi Free assigned parking Resort Features: Expansive oceanview pool Jacuzzi hot tub Over 15 acres of lush, tropical landscaping Low-density, two-story Mediterranean-style architecture (no elevators; stairs required) Nestled in the heart of Wailea! Maui’s most coveted resort enclave known for its ideal climate, this residence places you moments from world-renowned beaches, including Keawakapu, Ulua, and Mokapu. Championship golf at Wailea’s three iconic courses and premier tennis facilities are just minutes away, while upscale shopping, dining, and spa experiences await at The Shops at Wailea and nearby luxury resorts. Please note: While furnishings and décor may be updated from time to time, the level of quality, comfort, and accommodations will always meet or exceed what is shown. Important Notice: The pool area will be closed for scheduled maintenance from September 15–18, 2026, and will reopen on September 19 with regular hours. Hawaii Tax ID: TA-119-191-8592-01

Palms at Wailea 1201

Wailea, HI, US
2 Bedrooms 4 Guests
Aug 26 - 28
$383 night

Experience the ultimate South Maui escape at Palms at Wailea 1201, a beautifully appointed 2-bedroom, 2-bath Wailea vacation rental designed for relaxation and effortless island living. Perched above the soft golden sands of Keawakapu Beach, this spacious condo offers the perfect home base for beach days, sunset strolls, championship golf, and unforgettable Maui adventures. With tropical landscaping, ocean breezes, and a peaceful resort setting, you’ll enjoy the privacy of a condo with the amenities of a luxury retreat. Step inside to an open-concept living space that flows seamlessly onto your oversized private lanai through floor-to-ceiling sliding glass doors. Enjoy morning coffee surrounded by palm trees, afternoon pupus in the shade, or sunset dinners with seating for six. After a day exploring Wailea’s beaches or shopping at Shops at Wailea, unwind in the comfortable living area or cool off with split air conditioning throughout. Why guests love this Wailea vacation rental: Prime location in Wailea, minutes to beaches, golf, dining, and snorkeling Short distance to Keawakapu Beach for swimming, paddleboarding, and sunsets Spacious private lanai with outdoor dining for six Open living area with sofa sleeper for additional guests Fully equipped kitchen for cooking at home during your stay Primary suite with king bed and ensuite bath Guest bedroom with two twin beds, ideal for families or friends In-unit washer and dryer for extended stays Resort-style pool and Jacuzzi surrounded by lush tropical grounds Whether you’re planning a family beach vacation, a couples’ retreat, or a long-awaited Maui getaway with friends, Palms at Wailea 1201 offers comfort, space, and an unbeatable Wailea location — all in one inviting island home. Important Notes: Ground-floor unit; two sets of stairs required for access Private grills are not permitted on property Pool closure: September 15–18, 2026 (reopens September 19) Hawaii State Tax ID#: 107-673-3952-02

Palms at Wailea 304

Wailea, HI, US
2 Bedrooms 6 Guests
Aug 26 - 29
$438 night

If you are looking for a perfect getaway in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi and all the amenities this popular complex affords. This spacious fully air-conditioned two-bedroom two-bath unit is immaculate and beautiful and comes equipped with all the amenities so that you feel as if you are right at home. Enjoy the pleasant ocean views from the large wraparound lanai in a tropical garden setting. This unit has approximately 1200 square feet of living area plus a wraparound lanai. Top floor, tastefully furnished, split air conditioning, plush carpeting, gourmet kitchen, spacious living area, and lots of more. Located above the pristine shores of Keawakapu Beach, this impeccably furnished home will provide comfort, luxury, and plenty of room to spread out while you explore and enjoy all that Maui has to offer. The spacious covered lanai with a dining table allows for relaxing evenings while you kick back and enjoy the views. Relax poolside or take a Jacuzzi after the sun sets and take in the beauty of the brilliant Maui skies. The Wailea Golf Course and Tennis Clubs are just a minute away. Within walking distance are some of the World’s Top Beaches as rated by Conde Nast International. If shopping is your pleasure, the elegant Shops of Wailea are situated a stone’s throw away. For the adventurous type, you will find amazing snorkeling spots within a very short drive. Please note that Palms at Wailea no longer allows private grills. There will not be a grill for you to use on the lanai of this condo. While we strive to keep all photos up to date, there may be new and updated pieces of furniture or decor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve. Notice 2/18/26 - Pool Closure: Tuesday, Sept,. 15th -Friday, Sept,.18th 2026 The Pool Area Will Reopen Saturday September 19th with Regular Hours Hawaii Tax ID #: 152-503-2960-01

Polo Beach Club 309

Wailea, HI, US
2 Bedrooms 4 Guests
Sep 8 - 10
$401 night

First time offered for rent, Polo Beach Club #309 has been a lovingly cared for home up until now. Be the first to stay in this beautifully updated home with ocean views and palms to shade for privacy. #309 is a spacious and bright condo with soft whites and tans throughout giving that ethereal and relaxing vibe. Being a corner unit, this condo has an extra lanai so all rooms have outside access. Central AC throughout but don’t miss the chance to allow the natural Pacific Ocean breezes to cool the room and calm the soul. This island oasis will have you returning year-after-year to relax and reenergize! Condo Features Include: Living Area: -Dining table for up to 4 with bonus bar seating for 3 -Central AC -Large Smart TV -Floor-to-ceiling glass sliders Primary Bedroom: -Luxurious Queen Bed -Central AC -Plush Linens -Ceiling Fan -Smart TV -Lanai Access w/Glass Sliders En Suite Primary Bathroom: -Large tiled walk-in shower w/glass -Bidet on toilet Seat -Spacious vanity for getting beach ready 2nd Bedroom: -2 Twin beds that can be converted into a king upon request -Central AC -Plush linens -Ceiling fan -Room has its own lanai Guest Bathroom: -Large tiled walk-in shower w/glass -Spacious vanity for getting beach ready Kitchen: -Full size appliances: fridge w/ice maker, dishwasher, stove, oven, microwave -Small appliances: coffee maker, coffee grinder, blender, toaster, rice cooker -Plateware, glassware, cooking utensils and pots/pans provided Added Amenities: -Backpack style beach chairs -Beach towels -Washer & Dryer in condo -Free Wifi -Keyless entry lock on front door Property Highlights: -Oceanfront swimming pool -Oceanfront jacuzzi -Gas grill station -Herb garden -Direct Beach Access -12 acres of gorgeous landscaping and water features throughout -Free parking -Elevators (there are 3 stairs to this unit) The Polo Beach Club is situated on popular Polo Beach, famous for snorkeling and gorgeous sunset views. It is also located in the resort community of Wailea, offering world-class dining and shopping options all nearby at the different resorts and at The Shops at Wailea. The property has an ocean front swimming pool and a hot tub, perfect for soaking up the sun or relaxing after a long day at the beach. There are also communal BBQ grills on-site and an herb garden to enjoy. Upon arrival, you’ll find a white and blue parking pass in the unit for your vehicle. If you have a second vehicle, please stop by the AOAO office on-site for further instructions on where to park, as availability may vary depending on occupancy levels. Failure to park in designated areas may result in fines and towing. While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating and sleeping space will remain the same or may improve. Beginning April 15, 2026, a neighboring residence will be undergoing a remodel. In addition, the property will be completing an exterior power washing and painting. Noise levels are difficult to predict, however, there may be intermittent daytime disturbance Hawaii State Tax ID#: 028-810-9056-01

Mana Kai Maui Resort 202C

Kihei, HI, US
2 Bedrooms 6 Guests
Aug 30 - Sep 1
$462 night

Beautifully Renovated Condo Steps from the Ocean – Prime Kihei Location Welcome to your perfect Maui escape! This freshly upgraded and thoughtfully renovated condo offers the ideal blend of modern comfort and island charm. Located on the edge of Keawakapu Beach, you’ll be just moments from the sparkling Pacific Ocean where warm sand, gentle waves, and unforgettable sunsets are part of your daily routine. Inside, you’ll find a bright, refreshed living space featuring brand-new flooring, stylish fixtures, and upgraded appliances designed to make your stay effortless. Whether you’re preparing a quick breakfast before a beach day or unwinding after sunset, this condo delivers both comfort and convenience. ✨ What You’ll Love -Recently renovated interior with modern finishes -Updated kitchen appliances for easy, at-home meals -Open, airy layout with abundant natural light -Private, relaxing space just steps from the beach -Ideal for couples, small families, or a peaceful solo getaway ️ Resort-Style Amenities & Added Comforts Enhance your stay with access to a variety of on-site conveniences and resort-style features designed to make your vacation effortless and enjoyable: -Access to comfortable hotel-style suites with full baths, located just steps from the ocean—perfect for traveling companions or additional flexibility -Two gas grills available for outdoor cooking and casual island dining -On-site laundry facilities for added convenience during longer stays -Beach towels provided in both the condo and suites for use at the pool or beach Enjoy the relaxed atmosphere with amenities including: -A refreshing swimming pool -Open-air dining area with lounge seating -Fitness center and wellness options, including yoga classes with Maui Yoga Path -Activities center to help plan your island adventures -On-site gift shop and general store for essentials and souvenirs -Business center with computers -Conference and meeting facilities, ideal for remote work or group travel Unbeatable Kihei Location This condo places you in the heart of South Kihei, one of Maui’s most sought-after beach communities. For snorkeling and marine life encounters, you’re just a short drive from Molokini Crater, one of Maui’s most iconic underwater destinations. ️ Dining & Local Favorites You’ll be surrounded by some of Kihei’s best dining spots: Oceanfront favorites like Coconuts Fish Cafe for fresh island-style seafood Local-loved Kihei Caffe for hearty breakfasts and brunch Cafe O’Lei Kihei for a relaxed dinner with Hawaiian-inspired flavors ️ Shopping & Island Charm Just minutes away, enjoy convenient shopping and local culture: -Browse boutiques and open-air vendors at Kihei Kalama Village -Pick up essentials, gifts, and island-made goods nearby -Explore parks, coastal paths, and vibrant local events All guests need to stop by the Front Desk to register and receive a parking permit. Please park in the designated parking space for this unit. License number: 390040230002

Maui Hill 99

Kihei, HI, US
2 Bedrooms 6 Guests
Aug 31 - Sep 2
$186 night

Enjoy exclusive offers for all new reservations booked on or after October 13, 2024! Choose from one of the following promotions to enhance your stay: Book 5 nights, get the 6th night FREE! Complimentary late check-out for added relaxation! Stay now and receive a FREE night on your next booking! Book 5 nights or more and receive a $300 gift card to a local restaurant! Please note, only one promotion can be applied per reservation. These offers are valid for new bookings only and exclude reservations staying between December 20, 2024, and January 4, 2025. Take advantage of these limited-time offers and make your next getaway unforgettable! Maui Hill 99 offers the perfect Hawaiian hideaway. Great location with garden views. This comfortable 2bd/2bath condo offers room for the family or a couples retreat. Conveniently just a short drive to the World’s Top Beaches, The Shops at Wailea, casual to fine dining restaurants and more! As you enter this spacious condo you are welcomed by the tasteful décor. The quaint kitchen is fully equipped with plate ware and utensils as well as all of the cooking items any chef would need. Dining area offers seating for six. The expansive lanai right off the living area allows for enjoyment of the lush grounds. Dine al fresco with seating for four. The living area is appointed comfortably with a large sectional that converts to a full sleeper. Snuggle up and relax after a busy day on Maui with your favorite movie, complete with a flat-screen Smart TV, ceiling fan, and window AC. Family friendly with amenities that include child-sized beach chairs, pack and play, table-top strap on high chair, blow-up bed for toddlers, stroller, and beach toys. The charming guest bedroom offers that beach feel with crisp white beautiful linens and a cozy queen bed. Enjoy a quiet Maui morning with your own private lanai off the guest bedroom. There is a flat-screen TV and window AC unit for comfortable sleeping. The guest bath offers a luxury spa feel, with attractive counters and fixtures. There is a shower-tub combo and is conveniently off the guest bedroom. The primary suite offers a luxurious retreat! Drift off to sleep in the king bed with exquisite linens. Lounge on your lanai with access from your primary suite. Complete with flat-screen TV, ceiling fan, window AC, en suite bath with a striking tiled shower. Washer/dryer allow for lighter packing. *The owner of this condo has a minivan on Turo. Please message for details on adding a vehicle to your stay. Discount offered for guests of Maui Hill 130 or 99. Maui Hill Resort is located minutes from the premier resort area of Wailea, Keawakapu, and Kamaole beaches. The resort features a swimming pool, Jacuzzi, barbecue grills, tennis, a putting green, and shuffleboard. While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve. Hawaii State Tax ID#: 092-944-6400-01

Kihei Surfside 506

Kihei, HI, US
1 Bedrooms 4 Guests
Aug 30 - Sep 1
$211 night

Kihei Surfside 506 is a beautiful 1 bedroom home with 180 degree views of the ocean and islands. From your private glass lanai, watch magical sunsets nightly and Humpback Whales cruising by in the Winter months. The pristine grass area is ideal for sunning oceanside with a good book and a refreshing drink in hand. Updated finishes and furnishings along with plush linens and a fully equipped kitchen will make this condo your #1 choice year-over-year. This condo is North facing allowing the famous Maui Tradewinds to help cool the condo year-round. Efficient Ductless Split System AC in the living area and bedroom further assist on those warmer Summer nights. Condo features Include: Living Area: -Lanai Panoramic Ocean View high top seating for 2 -Split AC in Living Area -Plush Sofa -Dining table for 4 with bonus bar seating for 2 -SMART TV -Entire wall of floor-to-ceiling windows and glass sliders Bedroom: -King Bed -Plush Linens -Split AC -SMART TV -Ceiling Fan Bathroom: -Tiled walk-in shower w/glass doors -Spacious vanity for getting beach ready Kitchen: -Full size appliances: fridge w/ice maker, dishwasher, stove, oven, microwave -Small appliances: coffee maker, coffee grinder, blender, toaster, rice cooker -Plateware, glassware, cooking utensils and pots/pans provided Added Amenities: -Backpack-style beach chairs -Beach Towels -Free Wifi -Keyless entry lock on front door -In-Room safe Kihei Surfside is centrally located on the line between Wailea and Kihei and all of the dining, shopping, beaches and activities offered in both towns. The grounds here are spectacular! It is common to find morning yoga classes on the perfect grass area and is customary for guests and residents to meet nightly for sunset sips at the shoreline. Favorite Keawakapu beach stretches South and is perfect for long, sandy strolls as well as paddleboarding, kayaking and snorkeling. The neighboring resort is yards away and offers kayak and SUP board rentals as well as lunch and basic needs at 808 Deli and General Store and a new fine dining option is set to be completed in 2024. Property Highlights: -Heated Oceanfront Pool -Free Parking -Elevator -Gas Grill area -Putting green -Bocce Ball court -On-site coin-op laundry on ground floor While we strive to keep all photos up to date, there may be new and updated pieces of furniture or décor that are different than in the original pictures. The functionality, available seating and sleeping spaces will remain the same or may improve. Update (6/16): Elevator Out of Service 8/24-8/26 from 8am to 5pm each day. Hawaii State Tax ID#: 127-296-9728-02

Mana Kai #307

Kihei, HI, US
2 Bedrooms 6 Guests
Aug 26 - 28
$355 night

Located at the premier oceanfront property of Mana Kai, this upgraded 2 Bed, 2 Bath unit will make you never want to leave! Admire breathless views of the beach, ocean, Molokini Crater, and Kaho’olawe! Enjoy the fresh, modern interior with upgrades throughout! The moment you step through the front door, you are met with spectacular ocean views. Located on the award-winning Keawakapu beach, this unit has it all. The gourmet kitchen is equipped with upgraded appliances and beautiful bamboo cabinets to enjoy while dining in with a fully stocked kitchen and an amazing view! Enjoy sunsets in the evening out on your private lanai overlooking the stretch of beach as the sun goes down, and again in the morning as you sip your cup of coffee. The Ocean Front primary bedroom features a King sized bed and fully remodeled en suite bathroom. Sliding doors separate this bedroom from the living space to create a private space. The second bedroom also offers a king-size bed, stunning ocean views, and its own en suite bathroom for added comfort. Mana Kai 307 offers the perfect Hawaiian retreat! The resort atmosphere includes an oceanfront pool, two propane BBQ’s, onsite laundry facilities on each floor, free parking, fitness center, activities center, general store, and business center. Mana Kai will continue construction and maintenance effective immediately, including essential concrete repairs near the lobby and restrooms, as well as preparations for the new Beach House at Mana Kai restaurant by Handcrafted Restaurants (Peter Merriman, known for Monkeypod Kitchen, Merriman’s, and others). While we do not have a full schedule or end date yet, work will take place on weekdays from 8:00 AM to 4:30 PM, with no activity on weekends or holidays. Guests may experience some noise and temporary restroom closures during this time. We appreciate your understanding and look forward to welcoming you. (Update 11/25/24) Please be aware that all Mana Kai units feature a primary bedroom that is an ’’open concept’’ and is not closed off from the living room area. This particular unit has installed sliding shutter doors for added privacy. While we strive to keep all photos up to date, there may be new and updated pieces of furniture or decor that are different than in the original pictures. The functionality, available seating and sleeping space will remain the same or may improve. *Split AC in Living Room and Bedroom* HAWAII STATE TAX ID#: 054-063-9232-02

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Vacation Rentals Near Wailea

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