Home Vacation Rentals By Owner In Wailea, HI

Showing 60 Of 450 Vacation Rentals
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Exceptional(76)

$990.32

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Oceanfront Wailea condo w/ pool, lanai and snorkeling

Wailea, Hawaii, United States

Experience true paradise and stunning ocean views from the lanai as you sip on your morning coffee! Stroll along the world famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach or unwind and sunbathe at the ocean front pool and jacuzzi.brbrThis immaculate 2 Bedroom, 2 Bathroom accommodation is a slice of heaven. This unit features beautiful and tasteful furnishings, a fully equipped gourmet kitchen with an open floor plan, stainless steel appliances, tile floors throughout, and a fabulous lanai to watch the sunset and take in the beauty of Maui.brbrThis unit accommodates up to six guests and features a king-sized bed in the Primary Bedroom, two twin beds in the Guest Bedroom which can also be made into a King, and a very comfortable sleeper sofa bed in the living area. The Primary Bedroom features an ensuite bathroom, and there is also a second full guest bathroom. There is central air conditioning and wireless internet access throughout.brbrThe Polo Beach Club is situated in the resort community of Wailea, offering world-class dining and shopping options all nearby at the different resorts and The Shops at Wailea. The Polo Beach property features a pool and jacuzzi tub for guest use. There are also communal BBQ grills on-site and an herb garden to enjoy.brbrUpon 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.brbrWhile 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.brbrBeginning 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 disturbancebrHawaii State Tax ID#: 145-738-1376-01
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Exceptional(88)

$1356.63

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Private Vacation Home

Summer Deal Wailea Villa with Private Elevator and Beach Access

Wailea, Hawaii, United States

This property is hotel zoned, and not being affected by the recent proposed legislation.brbrRelax and enjoy your Maui vacation in this spacious and gorgeous villa located at Ho'olei. The top floor includes a beautifully designed living room, featuring a 70 HD TV with surround sound, premium channels to enjoy, and complimentary wifi throughout the unit. The open floor plan flows into the gourmet kitchen, featuring a gas stove top of the line appliances, a large refrigerator with multiple freezer drawers, and is fully stocked with cookware, plateware and glassware. Easily transport your groceries and luggage upstairs with your own personal elevator located in your unit!brbrThe living room seamlessly flows outdoors onto the spacious covered lanai through stackable sliding glass doors. Enjoy outdoor seating, a large outdoor gas grill, and mini fridge.brbrThe primary Bedroom is located on the lower level and features a King Bed, large ensuite bathroom with soaking tub, walk in shower, dual vanity sinks and a walk in closet! Enjoy your own private ground floor 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 private ensuite bathroom. The main living area also has a half bath to use as well.brbrAdditional amenities in the unit include full central AC, a private elevator within the villa, a full sized washer and dryer, private garage, covered carport across the driveway for a second vehicle, beach chairs and beach towels to use at the beach or at the property pool!brbrHo'olei property features a stunning pool with a waterfall, sandy beach area for children, and 2 jacuzzis to enjoy. Feel free to take the beach towels provided in your unit down to the pool to use! There is a also a fitness center to use next to the pool area, and a covered kitchen pavilion. Poolside massages also available! This is a gated community with 24 hour security available.brbrBeach 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 at nearby properties, but please note that pool access at the adjacent resorts is not included with your reservation at this Ho'olei villa.brbrWhile 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.Other things to notePlease note: Upon confirming your reservation, we will request your personal email address. A company specific rental agreement will be emailed to the provided address. Once we have received your completed rental agreement, detailed arrival instructions will be emailed to you one week prior to your stay.Registration number210081190104, TA-130-596-9664-01
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Exceptional(55)

$282.15

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Summer Deal Wailea Condo with Ocean Golf Views Pool and Hot Tub

Wailea, Hawaii, United States

Views! Views! Views! Experience breathtaking ocean and fairway vistas from this top-floor unit. This spacious condo features a generously sized living room, a cozy primary bedroom, and two full baths. Whether you're marveling at sunsets over the expansive 2nd fairway or catching a glimpse of a passing deer on the lawn during the early morning hours, you're in for a treat.brbrThis unit offers a high level of comfort. Unwind on your private lanai, where you can enjoy the refreshing trade winds sweeping across the greens and savor the delightful aroma of the beautiful Plumeria trees and Hawaiian foliage. This exceptionally roomy one-bedroom unit in the Grand Champions Villas is fully equipped with all the amenities to make you feel right at home. Fresh paint and new carpet were added in 2022 to enhance your stay.brbrPrime Location! The Grand Champions showcases lush, captivating landscaping and offers various amenities, including two pools, a Jacuzzi, BBQ facilities, and security. Its central Wailea location is a major plus, enabling you to walk to tennis courts, the Shops at Wailea, a variety of casual to fine dining restaurants, the world's top beaches, and five-star hotels.brbrNo matter what your vacation aspirations may be, this condo promises that you'll have an amazing time with your expectations met and memories created to last a lifetime.brbrWhile we do our best to ensure all photos are kept up to date, you may come across new and updated pieces of furniture or decor that differ from the original pictures. However, the functionality, available seating, and sleeping arrangements will remain the same or may have even improved.brUpdate 5/22: Dryer Vent Cleaning taking place between 8/3-8/13. br*Window A/C in every room*brHawaii Tax ID #: 037-546-8032-01
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Sleep 4

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Exceptional(62)

$422.37

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Stunning Ocean Views! Renovated Wailea Ekolu 502

Wailea, Hawaii, United States

Enjoy the fully remodeled kitchen, vaulted ceilings throughout, open floor plan, and STUNNING ocean views! All windows have been replaced, along with all furniture in living room and both bedrooms! This accommodation is a premier unit at The Wailea Ekolu property!brbrThe Primary Bedroom features a King bed and a private ocean view patio to enjoy! The bathroom has been remodeled, and features a full-size washer/dryer to use during your stay. The Guest Bedroom features two twin beds with another private lanai off the bedroom in a garden setting. The guest bathroom has also been remodeled!brbrWhen you think of Hawaii you imagine awe-inspiring views, amazing sunsets, and the natural beauty of the wild Blue Pacific. These sights are a daily pleasure from the comfort of your own private lanai and living area! Enjoy the un-obstructive Ocean Views, Kahoolawe, Molokini and West Maui Mountains! You may also see Whales during the winter season too!brbrGreat location and convenience!! This beautiful appointed home is situated on the Fairway of Wailea's elite Blue Golf Course. Walk along the Ekolu walkway pass to the World's Top Beaches, The Shops at Wailea, Five Star Hotels, casual to fine dining restaurants and more.brbrWhile 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.br*Window A/C in Living Room and Primary Bedroom Only*brbrWailea Ekolu Construction NoticebrPlease be aware that the Association has advised they do not proactively inform owners or property managers about ongoing construction. Work may take place intermittently at any time between May 1st and October 31st.brHawaii Tax ID #: 027-842-8160-01
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$559.86

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Palms at Wailea Garden Deluxe Villas 2 BD 2 BA

Wailea, Hawaii, United States

Deluxe garden-view villas offer a tranquil retreat surrounded by lush tropical landscaping in Wailea’s resort community. With a full kitchen, inviting living space, and private patio, it’s an ideal home base just minutes from beaches and golf courses. brbrGarden Villa Deluxe 2 Bedroom 2 Bathbrbr• Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, cookware, and tableware brbr• Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent brbr• Master bedroom has 1 king bed or 1 queen bed brbr• Second bedroom has 1 queen bed or 2 twin beds brbr• Master bathroom with free-standing shower or shower/tub combination brbr• Second bathroom with free-standing shower or shower/tub combination brbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryer brbr• Dining area brbr• Living area with sofa bed brbr• Ceiling fan in living room brbr• Air conditioning in master bedroom only; some units have AC in entire unit & is available on request at $20 per night brbr• Shutters brbr• Washer/dryer in unit brbr• Balcony or patio with furniture brbr• TV with standard cable brbr• Wi-Fi brbr• In-room safe brbr• Iron and board brbr• Smoke detectors brbr• Children 17 years and under are free when sharing room with parent(s) utilizing existing beds brbrThis listing features a wonderful collection of condos that we manage in this category. The Photos you see capture the unique character of these properties, giving you a taste of what each has to offer. We can't wait for you to find your perfect getaway!
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Exceptional(30)

$684.51

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Grand Champions 87 ocean-view condo with pool, hot tub & washer/dryer

Wailea, Hawaii, United States

Wailea Grand Champions 87brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNewly and beautifully remodeled from top to bottom, this golf-course-front condo in the heart of Wailea will treat you to sunset views over the ocean and an overwhelming feeling of aloha. Enjoy thoughtful additions, including three split Mitsubishi air-conditioning units, new furnishings and mattresses, new tile work in the showers, and new floors, cabinets, and granite countertops. Whip up favorite beach snacks and homecooked meals in the well-equipped kitchen - the fridge includes an ice maker for crisp beverages. Sip your coffee on the lanai as passing golfers putt for par, or sunbathe by the shared swimming pool and hot tub as the plumeria scents waft by. You'll always come home to high-speed WiFi, three flatscreen TVs, and majestic sunsets to view from the lanai.brbrThis condo sits less than a mile from Wailea Beach, which is known as one of Maui's premier beaches and a fantastic snorkeling and SUP spot. Many national high-end shops, local retailers, and Maui musicians are featured in The Shops at Wailea half a mile down the hill. Near there, you'll find great views and food at Manoli's Pizza Company, an ideal spot to end your day after playing 18 at the Wailea Blue Course (known locally as 'Old Blue'). For a romantic night, head to the nearby Four Seasons and take in the sunset at the beachside Ferraro's Bar e Ristorante.brbrRESORT AMENITIESbrPoolbrHot tubbrGas grillbrbrTHINGS TO KNOWbrWailea Grand Champions is a non-smoking property. Smoking is not permitted anywhere on the property or in lanais.brOne reserved parking spot (and ample visitor parking) are available for guest use.brThis property is managed by Vacasa Vacation Rentals of Hawaii LLC.brbrParking notes: There is free parking available for 1 vehicle.brThis rental is located on floor 1.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Sleep 4

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Exceptional(49)

$302.68

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Condo

Wailea Ekahi #45-E Ocean View Beachfront Resort Great Rates, Pool, Near Beach

Wailea, Hawaii, United States

Wailea Ekahi #45-E is a 1 bedroom, 2 bath unit on the second floor and has an ocean view, fully-equipped kitchen, washer and dryer, 2 flat-screen TVs, DVD, and free Wifi. The bedroom features a king bed with pillow top mattress pad, ceiling fan, flat-screen TV, and full bathroom. There is a sofa bed in the living room. For outdoor activities, Wailea Ekahi #45-E is supplied with beach chairs and beach towels. BBQ grills are not allowed on individual unit lanais in compliance with fire code restrictions. Wailea Ekahi features six community grilling stations around the property available to guests. This unit has no AC. Sleeps 4. Please note: This unit is on the second floor with no elevator available. brSame day bookings and those arriving within 24 hours of making the reservation requires a phone call to Rentals Maui for confirmation. brBookings made within 7 days of arrival will require an ID check and screening prior to confirmation.brLonger stays require additional terms and conditions. Please contact Rentals Maui for inquiries longer than 60 nights. brWe work to maintain a very accurate website. At times furniture, decor or flooring may be upgraded and pictures are not updated yet. This would not change the seating, sleeping, function or views of the condo. Amenities are accurately and clearly listed for your convenience.brWailea Ekahi Village is a 34-acre beachfront complex. The beautifully manicured grounds offer enchanted walking paths to the beach. Hang out at Keawakapu Beach in front of the village, play paddle tennis or shuffleboard, or swim in one of our four swimming pools--one of which is an oceanfront pool with a pavillion and BBQ grills. The pavilion is a gorgeous space to gather with friends or just hang out. Features include a modern open kitchen, BBQ grills, fitness center, table seating both shaded and sunny, a book lending library, and showers with changing room for pool users. The famous Wailea Beach Walk passes directly in front of Wailea Ekahi Village and leads to more beaches, shops, and restaurants. Wailea Resort offers golf courses and tennis.br** Important Notices: (1) The main pavilion pool will be closed for resurfacing August 10-2026 until October 15, 2026. The three other pools, fitness room, grills, and kitchen will remain open. (2) A property-wide exterior painting project is scheduled for August 2025 - September 2027. Extension ladders, scaffolding, and pressure washers will be visible around certain locations of the property during this time. This building will be affected August 11-24, 2026. Call our office for additional information. **
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Sleep 4

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Exceptional(11)

$968.45

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Maui Resort Rentals: Wailea Elua 2204 − Luxuriously Remodeled 2BR w/ Stunning Ocean Views, New Listing!

Wailea, Hawaii, United States

Boasting stunning panoramic views of the Pacific Ocean that extend deep into the home's living, kitchen, and dining areas, Wailea Elua 2204 is a luxuriously renovated second-floor villa featuring some of the most spectacular vistas South Maui has to offer. Watch breaching whales splash just off the coast in the winter months and take in incredible sunsets from the comfort of your living room. brbrFold away the fully stacking sliding doors in the living area and lose yourself in the warm sea breeze and the gentle sound of waves hitting the shore from your expansive private lanai, recently upgraded with glass paneling to fully optimize visibility.brbrBeyond its dreamy coastal setting, the residence has been completely remodeled to include upgraded finishes like travertine flooring, custom European sycamore cabinetry, and granite counters, accented by gorgeous contemporary island decor. The gourmet kitchen has been outfitted with top-of-the-line Bosch and Thermador appliances and stocked with all the utensils you will need to prepare delicious meals and refreshments during your stay. brbrThe villa's 1300+ sq ft interior can comfortably accommodate up to six guests, with a sumptuous king-size bed in the primary bedroom and a spacious queen-size bed in the guest bedroom. Both bedrooms and the living space feature a flat-panel TV for your viewing enjoyment. For additional sleeping capacity, we are happy to provide two complimentary memory foam floor mattresses upon advance request.brbrIf you wish to avoid excessive baggage fees from the airlines, consider packing lighter and utilizing the high-efficiency washer and dryer in the residence.brbrTucked along the stunning shore of Ulua Beach in the heart of South Maui, Wailea Elua invites its visitors to step away from the hurried pace of daily life and ease into the soothing tempo of island living. Flanked on both sides by world-class resorts, this quiet 24-acre gated community flaunts breathtaking views, unparalleled relaxation, and world-class dining and shopping just steps from your door.brbrBreak a sweat at the beachfront fitness room featuring state-of-the-art cardio and weight machines before cooling off in the lavish beachside pool overlooking the ocean. The poolside kitchen and numerous dining tables make preparing quick meals and drinks easy on long days spent by the pool. brbrA second, more centrally located pool surrounded by lush tropical foliage offers an inviting hot tub and secluded space for soaking up the sun. If you prefer to lounge oceanside, find one of the private cabanas at the grassy point above Ulua Beach. From pickleball matches with friends to meals cooked at the community outdoor grill and eaten under the beachfront pavilion, the property offers something to be enjoyed by every traveler.brbrWhen it's time to hit the beach, take advantage of the convenient “Ohana Play Package,” including Tommy Bahama beach chairs, BBQ equipment, and a portable cooler located in your residence. Spend your days exploring one of the four pristine, palm-shaded beaches that line the miles of Wailea Beach Path that starts at the front of the property. The gorgeous path conveniently connects each resort to the next, making it easy to access all the fine dining, high-end spas, luaus, and nightlife that Wailea has to offer.brbrGolfers will enjoy stunning panoramic mountain and ocean views from Wailea's three challenging hillside courses, including the Blue Course, situated right across the street, the Emerald Course, and the Gold Course, as well as a nearby seaside course, located to the south in Makena.brbrIf during your stay you require assistance or advice about the surrounding area or the suite, rest assured that you’ll be swiftly taken care of with aloha by one of our friendly & knowledgeable liaisons, handpicked from Maui’s leading luxury hotels.
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Exceptional(66)

$1105.3

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Stunningly Renovated! Ocean View! Elua 2305

Wailea, Hawaii, United States

This property is hotel zoned, and not being affected by the recent proposed legislation.brbrWelcome to Elua 2305. Your ultimate Maui vacation awaits at this fabulous listing! Don’t miss this incredible opportunity to enjoy the very best that Maui has to offer.brbrSay Aloha to Elua Village, a private, beachfront resort that spans 24 acres of meticulously manicured lawns and gardens. Located in the heart of Wailea on the famous Ulua Beach, this resort style complex has everything you need right at your fingertips. Whether you seek the peace and serenity that Maui offers or adventure, this resort has it all!brbrStart your day meandering the world famous Wailea Beach Walk that takes you from Ulua Beach to all of the resorts, spas, restaurants and more stunning beaches located nearby. There is no need to walk far as Elua Village boasts two swimming pools and Jacuzzis, including one that is located beachfront with a beautiful pavilion and fitness center. The beach pavilion offers a lounge area, TVs, BBQ grills and workout equipment. It is the perfect setting to soak up the sun or indulge in pupus (appetizers) and your favorite beverage! Feel like you have the whole beach to yourself with a gated point access lounge area. Enjoy outdoor fitness at the tennis and pickle ball courts located a short walk from your condo. Wailea Elua now also offers a pickle-ball court!brbrAfter a long day of enjoying the very best that Maui has to offer, come home to a fully renovated two bedroom / two bathroom condo. This stunning ground floor residence was remodeled in Fall of 2018 and boasts one of the largest lanais in all of Elua Village. If you truly want to experience the Maui lifestyle this home is perfect for you! The large sliders in the living room open to the lanai to enjoy the cooling trade winds and indoor/outdoor living. Incredible sunsets await you every evening on the lanai. In the winter months make sure to keep your eyes peeled for the magical humpback whales that migrate to Maui. Located just off the lanai is an expansive green belt that adds to the peaceful and serene setting.brbrFeel at home in the gorgeous gourmet kitchen that is fully equipped for the Chef of the family! This open and bright floor-plan opens up to the living room and dining area, making it perfect for entertaining your family and friends. Located down the hall you will find two bedrooms and bathrooms. The guest bedroom features two twin size beds that can be converted to a king upon request and private access to the lanai. The guest bathroom is located across the hall for easy access with double sinks and a stunning walk in shower. The primary bedroom is your private retreat with a king size bed and en suite bathroom that has an oversized luxury walk-in shower and double sinks. This residence is perfect for couples and small families!brbrYour dream Maui vacation awaits!brbrWhile 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.Other things to notePlease note: Upon confirming your reservation, we will request your personal email address. A company specific rental agreement will be emailed to the provided address. Once we have received your completed rental agreement, detailed arrival instructions will be emailed to you one week prior to your stay.br*Central A/C*brbrbrRegistration number210080700061, TA-072-622-4896-02
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Exceptional(34)

$528.72

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Condo

BEAUTIFUL BRAND NEW REMODEL-OCEAN VIEWS-SLEEPS 8-AC-WELL EQUIPPED

Wailea, Hawaii, United States

Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been newly remodeled. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7 to our guests. This condo offers an exceptional vacation experience and is fully equipped with everything that you need to have a great vacation. We are committed to provide our guests a clean and sanitized unit, by following enhanced cleaning protocols developed by experts in the health and hospitality industry. Some of the features of the condo include:brbr-The Grand Champions Villas, Unit #174br-Ocean And Garden Viewsbr-Quiet Location Backing Onto Golf Coursebr-Cabinetry With Granite Countersbr-Luxury King Bed In Master Bedroombr-2 Queen Beds In The Second Bedroombr-Pullout Queen Sleeper Sofabr-Free WIFI Internetbr-Free Parkingbr-Full Sized Washer / Dryerbr-Large Walk-In Shower In The Master Bathroombr-Fully Equipped Kitchen With BBQ Platters And Utensilsbr-Stainless Steel Appliancesbr-3 Large Flat Screen, Smart TV'sbr-Bluetooth Speakerbr-Tommy Bahama Beach Chairsbr-Boogie Boardsbr-Beach Umbrellabr-Beach Coolerbr-2 Pool Area's At The Resortbr-Manicured Tropical Landscaping Throughout The ResortbrbrThe Grand Champion Villa's are known for its great location within Wailea. Within a short distance are world class restaurants, shopping, and golf courses. Phenomenal accommodation at a reasonable price. The condo is located on the second / top floor of the building and there is a set of stairs to climb to access the front door.brbrCancellation Policy: If you cancel prior to the balance being due (30 days prior to arrival), nothing further for the reservation would be processed and you would only forfeit the deposit. If you cancel after paying in full, we will refund you for any nights that we are able to rebook, minus the $400.00 deposit. If we were to close to tourism, you would be fully credited the amount that you have paid towards a future booking and the balance would not be processed. Travel Insurance is available and strongly encouraged.brbrHI Tax ID#: TA-205-640-6528-01brbrWe Accept Visa And MasterCard
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Exceptional(45)

$1191.86

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Villa

Summer Deal Wailea Townhome with Private Lanai Pool and Beach Access

Wailea, Hawaii, United States

This property is hotel zoned, and not being affected by the recent proposed legislation.brbrThis lovely villa is designed for indoor-outdoor living featuring sliding pocket doors that lead outside to the spacious private lanai. Take advantage of alfresco dining, cool tropical breezes, garden views, and a large outdoor gas grill.brbrLounge on the lanai and sip on a tropical beverage while taking in the beauty of Maui. This accommodation includes a beautifully designed living area, modern furnishings, a fully equipped gourmet kitchen with a breakfast bar and top-of-the-line appliances, a flat-screen television, and WiFi throughout. Easily transport your groceries and luggage upstairs with your own personal elevator located in your unit.brbrThe Primary Bedroom is incredibly spacious and features a California King Bed, a large ensuite bathroom with a soaking tub, walk-in shower, and a private lanai! The second Guest Bedroom is located downstairs with a king bed and a full ensuite bathroom. The top floor features a third guest bedroom with two queen beds, a private bathroom, and French doors leading out to a French balcony. The main living area also offers a half bathroom for guests to use.brbrThis two-story townhome also features central air conditioning throughout, a full-sized washer and dryer, a private garage, covered carport across the driveway for a second vehicle, beach chairs, and beach towels to use at the beach or at the property pool!brbrHo'olei property features a stunning pool with a waterfall, a sandy beach area for children, and 2 jacuzzis to enjoy. Feel free to take the beach towels provided in your unit down to the pool to use! There is also 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.brbrBeach 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 at nearby properties, but please note that pool access at the adjacent resorts is not included with your reservation at this Ho'olei villa.brbrWhile 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.brbrHawaii Tax ID 009-754-4704-01
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$1821.8

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Grand Champions | 2 Free Rental Cars | KBM Resorts | Extra Large Corner Suite | 2 Units, 5 Bedrooms | ML-1149

Wailea, Hawaii, United States

brbr** 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.brbrWelcome to your spacious Maui retreat at Grand Champions Resort. This composite listing combines two comfortable villas, GCH-120 and GCH-134, creating an expanded layout ideal for families, couples traveling together, or groups seeking both connection and personal space. With generous square footage, thoughtful amenities, and resort-style surroundings, this paired-villa arrangement offers an easy and enjoyable Maui stay. brbrGCH-120Guests appreciate the warm, inviting bedrooms that offer comfort and privacy for quiet mornings or peaceful evenings.brbrGCH-134Additional bedrooms provide the same relaxing ambiance, complete with soft tones and natural light that help guests settle into island life.brbrTogether, the combined villas accommodate up to 12 guests, with flexible sleeping arrangements suited for both families and groups. These two villas are separate, but only a short one-minute walk from one to the other.brbrBEDROOMSThis composite includes a total of five bedrooms arranged across the two villas, giving every guest a relaxing place to unwind. Each bedroom features comfortable bedding, soothing decor, and a restful setting after days spent exploring the island.brbrBATHROOMSAcross the two villas, guests have access to four well-appointed bathrooms, making it easy for everyone to get ready for beach days, dinners, or excursions. Clean finishes and practical layouts ensure comfort for the entire group.brbrKITCHENSEach villa includes its own fully equipped kitchen with full-size appliances, ample counter space, and all essentials for preparing meals at home. Having two kitchens offers added convenience-especially for larger groups-whether cooking breakfast, packing picnic lunches, or enjoying relaxed evenings together.brbrLIVING AREASCombined, the villas offer over 2,600 square feet of interior living space with comfortable seating, natural light, and welcoming areas for gathering. Both living rooms provide space to lounge, watch movies, or share time together after a day on the beach.brbrOUTDOOR SPACEGuests have access to private lanais totaling over 450 square feet between the two units. These outdoor spaces are perfect for morning coffee, afternoon relaxation, or enjoying the warm Maui air any time of day.brbrWHAT GUESTS ARE SAYINGTravelers love the flexibility and comfort this composite provides. The dual-villa setup offers room to spread out while still making it easy to gather for meals, games, or conversation. Guests also enjoy the convenience of multiple kitchens, generous bedroom layouts, and access to all the resort amenities.brbrYour stay includes attentive local support, responsive communication, and professional on-island management to ensure a smooth and enjoyable experience.brbrWhen you're ready to enjoy the beauty, warmth, and laid-back rhythm of Maui, this welcoming composite retreat at Grand Champions Resort is ready to host your unforgettable island getaway.brbr #TA-008-966-2976-01 #TA-109-775-9232-01 brbrThis property is professionally managed by KBM Resorts, your premier source for luxury vacations. The calendar and rates below are always accurate - last update was today at 4:22 PM. brbr
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$2028.34

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Wailea Elua Village | 2 Free Rental Cars | KBM Resorts | Panoramic Ocean Views Wailea Elua Village 2-bedroom Villa | 2 Units, 4 Bedrooms | ML-1137

Wailea, Hawaii, United States

brbr** 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.brbrWelcome to your relaxing island escape at Wailea Elua Village. This composite brings together two villas close by, WEV 2009 and WEV 2103, offering a combined 2918 square feet of interior living space and 772 square feet of outdoor lanais. With generous layouts, peaceful surroundings, and ocean views, this paired villa setup is ideal for families, couples, or friends who want to stay close while still enjoying personal space. Soft breezes and the calm beauty of Wailea create the perfect setting for a memorable Maui stay.brbrBEDROOMSThis composite includes four total bedrooms arranged between both villas, giving each guest a quiet and comfortable space to unwind after days spent exploring the island.brbrWEV 2009This welcoming villa provides bright and calming bedrooms with soothing decor and cozy bedding. Guests appreciate the restful atmosphere and the peaceful privacy of this unit.brbrWEV 2103Located just steps away, WEV 2103 offers additional well appointed bedrooms with natural light and gentle island colors. Perfect for families and couples alike, each room offers a relaxing retreat throughout your stay.brbrTogether, both villas sleep up to 12 guests comfortably.brbrBATHROOMSWith four total bathrooms, mornings and evenings flow smoothly for groups of all sizes. Clean finishes, spacious showers, and well designed layouts ensure everyday convenience.brbrKITCHENSEach villa features a fully equipped kitchen with full size appliances, generous counter space, and everything needed for meals at home. Preparing breakfast, beach snacks, or a shared dinner is easy and enjoyable with two complete kitchen spaces.brbrLIVING AREAWith nearly 3000 square feet of interior living space between both units, your group has plenty of room to gather, relax, and enjoy time together. Both villas include welcoming living rooms with soft seating and natural light, creating a comfortable setting for conversations, games, or quiet evenings.brbrOUTDOOR SPACEThe composite includes 772 square feet of total lanai space, perfect for morning coffee, evening sunsets, or simply enjoying the warm Maui air. These outdoor areas extend your living space and offer peaceful views of the surrounding resort grounds.brbrWHAT GUESTS ARE SAYINGGuests love the flexibility and comfort this composite provides. The two villas offer privacy when desired while keeping everyone close for shared meals, gatherings, and quiet evenings on the lanai. Families especially appreciate the multiple kitchens, spacious layouts, and the relaxing atmosphere of Wailea Elua Village. As guests of this resort community, you are moments away from beautiful beaches, scenic pathways, oceanfront pools, and the charm of Wailea.brbrWith attentive local support, responsive communication, and professional onsite management, your stay is designed to be smooth and stress free. Offering space, comfort, and convenience, this composite is an ideal choice for groups seeking an unforgettable Maui experience.brbrWhen you are ready to enjoy the sun, tranquility, and natural beauty of Wailea, this inviting Maui retreat is ready to welcome you. Reserve your stay today and begin your unforgettable island escape.brbr #TA-039-466-1888-01 #TA-000-002-8672-01 brbrThis property is professionally managed by KBM Resorts, your premier source for luxury vacations. The calendar and rates below are always accurate - last update was today at 5:02 PM. brbr
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$329.57

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Condo

Wailea Ekolu #906 Great Location, Panoramic Ocean View, Private, Full A/C

Wailea, Hawaii, United States

Wailea Ekolu #906 is a 2 bedroom, 2 bath unit on the 2nd floor with panoramic ocean views, air conditioning, and complimentary wifi. Both bedrooms are equipped with air conditioning and ceiling fans. The open kitchen is fully stocked with everything you need! The master bedroom has a California king bed and the en suite bathroom features a tub/shower combo. The second bedroom has two twin beds and the second bathroom has a walk-in shower. The living room also provides air conditioning and is equipped with a large flat-screen television. For outdoor activities, Wailea Ekolu #906 is equipped with beach chairs and beach towels. BBQ grills are not allowed on individual unit lanais in compliance with fire code restrictions. Community grilling stations are available. Sleeps 4. brPlease note: This unit is on the second floor with no elevator available. brSame day bookings and those arriving within 24 hours of making the reservation require a phone call to Rentals Maui for confirmation.brBookings made within 7 days of arrival will require an ID check and screening prior to confirmation.brLonger stays require additional terms and conditions. Please contact Rentals Maui for inquiries longer than 60 nights. brWe work to maintain a very accurate website. At times furniture, decor or flooring may be upgraded and pictures are not updated yet. This would not change the seating, sleeping, function or views of the condo. Amenities are accurately and clearly listed for your convenience.brWailea Ekolu is one of most sought after properties in Wailea as it is nestled on the Wailea Golf Course. The property has a quiet and private atmosphere as the buildings are spread out across the lush tropical foliage. Wailea Ekolu has two lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. brThe beautiful Mokapu and Ulua Beaches are just a 10 minute stroll down the hill from Wailea Ekolu. Wailea Ekolu is located on the Wailea Golf Course and is across the street from the Wailea Tennis Club making it the perfect destination for golfers and tennis enthusiasts. It is also near The Shops at Wailea. Fronting the beach is the Wailea Promenade where you can walk along the beach for miles. Whale watch, paddle board, body surf and watch the most amazing sunsets imaginable. Wailea Ekolu is a property where the guests return year after year for a restful and tranquil Hawaiian vacation.
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$1208.48

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Villa

Summer Deal Luxury Wailea Villa with Pool Spa and Beach Access

Wailea, Hawaii, United States

Special Luxury Promotion brBook 7 Nights and Enjoy the 8th Night FreebrbrIndulge in the ultimate getaway at our luxury residence and extend your stay on us. Reserve seven consecutive nights and receive the eighth night completely free, the perfect way to elevate your vacation experience.brbrBlackout Dates: December 20 – January 4brNote: Discounts cannot be combined with any other offers.brbrTreat yourself to more time in paradise. Let us know when you’d like to book!brbrThis hotel-zoned villa sits within a prestigious, gated community not impacted by recent proposed legislation, offering travelers confidence and flexibility when planning their future maui escapes.brbrYour private retreat is a spacious, two-story luxury villa designed for comfort, style, and effortless island living. Thoughtfully placed on the property for enhanced privacy, the expansive upper-level living space opens fully to a covered lanai through oversized stackable glass doors, creating a seamless indoor-outdoor flow. Gather around the dining table for six, fire up the outdoor gas grill, and turn meals into lasting vacation memories surrounded by lush tropical beauty and island breezes.brbrInside, the open-concept top floor feels bright, airy, and refined, featuring a beautifully designed living room that connects effortlessly to the gourmet chef’s kitchen. Outfitted with a gas cooktop and premium appliances—including a large refrigerator and multiple freezer drawers—the kitchen comes fully stocked with cookware, dishware, and glassware, making it ideal for everything from morning pancakes to sunset dinners.brbrDownstairs, the carefully designed layout gives every guest their own space to recharge. The primary suite offers a king bed, walk-in closet, dual vanity, walk-in shower, and a deep soaking tub—your personal spa sanctuary. Step outside to your exclusive ground-floor lanai with lounge chairs, a peaceful oasis surrounded by tropical foliage. The second downstairs suite features a king bed and a full ensuite bathroom for added comfort and convenience. Completing the villa, the upper-level guest bedroom includes two full-size beds and its own private ensuite.brbrAdded conveniences elevate every stay—enjoy full central ac in every room, a private garage and covered carport, a full-size washer and dryer, plus complimentary beach chairs and plush towels for pool days and beach adventures alike.brbrWithin the community, resort-style amenities set the scene for relaxation and family fun: a striking waterfall pool, a shaded grotto, a sandy keiki play area for younger guests, and two inviting jacuzzis to unwind in at the end of each day. A nearby fitness center and covered kitchen pavilion offer even more spaces to enjoy, and on-site poolside massage services are available for guests wanting the ultimate indulgence. Around-the-clock gated security adds comfort and peace of mind throughout your stay.brbrFor effortless beach days, access is located directly across the street via the neighboring resort pathways. Guests may also take advantage of the resort’s highly rated restaurants and spa services during their stay. Please note: the neighboring resort pool is not included with your villa reservation.brbrFurnishings and decor may occasionally vary from current photos due to upgrades, however seating, comfort, and sleeping capacity will remain the same or may be enhanced.brbrThis villa is the perfect blend of luxury, privacy, convenience, and island lifestyle—an inviting retreat for families, long-stay travelers, and guests seeking an elevated maui experience.brbrRegistration number 210081190105brHawaii State Tax ID: 188-260-1984-01
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$667.19

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Condo

Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions

Wailea, Hawaii, United States

Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is a prime example of what Wailea Grand Champion Golf Villas has to offer in a 3 bdrm + 2 bath category. Upgraded throughout with split A/C systems, a superb kitchen and fantastic sunset views across the Wailea Ol' Blue Golf Course and the West Maui mountains.brWailea 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. Note: No assigned parking space. Guests to park in any available GUEST parking space.brbrBeach chairs, beach towels and coolers are provided. Additional beach gear may be rented at one of our local beach shops.brbr**Please note**brAll Holiday reservations are due, paid-in-full on October 1st. Holiday season is 12/15 to 1/10brNo refunds on Holiday cancellations after October 1st.brbrDiscounts for 14-day and 30-day stays are already included in total price shown.
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