Home Vacation Condo Rentals By Owner In Wailea, HI

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Exceptional(3)

$2095.78

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Immaculate Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium

Wailea, Hawaii, United States

Please call or email us about the dates for your visit. You are welcome to island-hop or come and go as you please during your reservation. brbrThis is The Pinnacle at Wailea Point. Brand new as of June 2023, third bedroom and fourth bathroom private loft added. Treat yourself because it doesn't get any better than this - luxurious 3 Bedroom / 3+ bath residence with captivating ocean and neighbor island views that will impress every guest. Exquisite luxury finishes and furnishings adorn this premier accommodation at one of Wailea's most exclusive destinations. A gourmet kitchen with dining table seating for 10, 3 separate and private bedrooms each with ensuite bathrooms. Impeccable wood floors, superior appliances, and top-tier entertainment electronics throughout the home make it a magical place to spend a Maui Holiday. Want to bring more of the family Fortunately, the adjacent condominium downstairs is also available to rent if you would like to bring additional friends and family! brbrWailea Point is a short walk to the sugar sand beaches immediately adjacent to the north in front of the Four Seasons Hotel and to the south in front of the Fairmont Kealani Hotel. Walk to lunch or dinner at the Wailea Four Season Hotel or the Fairmont Kealani Wailea. This premier vacation-home is set in a quiet location among beautiful, lush grounds with swimming pools, pickleball courts, a gym, and a friendly welcoming staff. You can whale-watch from your kitchen, living room and dining room!brbrWailea Point Village is a premier vacation property featuring 130 condominium homes in lush, tropical surroundings with 4 swimming pools and breath-taking ocean views, all in a low-rise village atmosphere. Located in the heart of Wailea on Maui's sunny south shore, Wailea Point sits between two popular Wailea beaches, close to premier snorkeling and dive spots and is adjacent to Wailea's award winning Blue Golf Course, just across the street from the Wailea Point resort and the nearby Shops at Wailea. Special rates are available for Wailea Point Village Guests at Wailea's golf and tennis facilities. Hotels, spa facilities and award-winning restaurants are within walking distance.brbrWailea Point Village features four large swimming pools, near the beach with facilities for entertaining, and a whirlpool spa. Picturesque beaches are just steps away; ideal for family fun, snorkeling, swimming, sailing, windsurfing or just relaxing. Located on the mile-and-a-half beach walk which gently meanders along the Wailea Resort beach and oceanfront, Wailea Point Village offers the security of 24-hr gated access and the convenience of Wailea's many shopping, dining and entertainment choices. brbr **Please note**brAll Holiday reservations are due, paid-in-full on October 1st. Holiday season includes dates within 12/15 to 1/10brNo refunds on Holiday cancellations after October 1st.brFurnishings, fixtures, and equipment are subject to change as necessary or preferred by client and may not be exactly as pictured. Photos are of the exact condominium that you will be renting. Property amenities are subject to availability and access per the Owners' Association. All reservations are for a minimum of 30-days as required by the Owner Association.
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$467.33

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Palms at Wailea Villa 301 Garden Deluxe 1 BD 2 BA

Wailea, Hawaii, United States

Relax in this one-bedroom villa with tranquil garden views in the heart of Wailea’s resort community. Designed for comfort and convenience, it features a full kitchen, airy living space, and easy access to beaches, golf courses, and walking paths. brbrVilla 301 Garden 1 Bedroom 2 Bathbrbr• Located in building 3 on ground floor with a reserved parking stall in front brbr• 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• Bedroom has 1 king bed brbr• Master bathroom with shower/tub combination brbr• Second bathroom with free-standing shower brbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryer brbr• Dining room table with seating for 4 brbr• Living area with sofa bed brbr• Air conditioning in entire unit brbr• Ceiling fan in living room brbr• Shutters brbr• Washer/dryer in unit brbr• 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
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Exceptional(9)

$561.86

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Spring Special – Your Oceanfront Paradise Awaits

Wailea, Hawaii, United States

Spring Special – Direct Bookings OnlybrbrStay 5 Nights, Get the 6th FreebrBook a stay for April 2026, and enjoy the 6th night free - perfect for extending your getaway at no extra cost!brbrDiscover Hawaiian paradise at this beautifully decorated 1 bedroom, 2 bath premium condo in the oceanfront Ekahi Village resort. Highlights include:br • Spacious primary suite with king bedbr • Living area with sleeper sofabr • Split ACbr • Fully-equipped kitchenbr • Dining area with seating for 4br • Private lanai with lush garden viewsbr • Brand new large smart TVbrbrThis upgraded unit is located within the renowned Ekahi Village offering:br • 4 swimming pools surrounded by tropical landscapingbr • Large heated beachfront pool with sunset pavilionbr • Pavilion with grills and direct beach access (no roads)br • Pickleball courtbrbrStep right onto Keawakapu Beach from the resort grounds! This sandy beach connects to several other celebrated Wailea beaches. Follow the beachfront path to Wailea Shops, Tennis Club, and five ultra-luxury resort hotels.brEnjoy stunning sunsets, whale watching (seasonal), snorkeling, paddleboarding, oceanfront dining, and easy walking access to Wailea's upscale restaurants and shopping - all mere steps away!brbrWorld-famous golf courses and amenities are also just minutes from this prime Wailea location. Ekahi Village offers the quintessential Hawaiian vacation experience! Book now for an unforgettable Maui getaway.brbrNew Fitness Center. The facility is available from 7:00 AM to 10:00 PM daily. Located just inside the Beach Pavilion, there are 3 pieces of cardio equipment, dumbbells ranging from 1-50 lbs, and a few other accessories that provide a full body workout. You must be 18 or over, sign a waiver of release, and no swim attire is permitted. Close-toed athletic shoes are required and ask that users dress appropriately.brbrImportant notice 1/5/26: The Pavilion Pool at Ekahi is anticipated to undergo resurfacing sometime between August 16 and October 16, 2026. While a formal schedule has not yet been confirmed by the Board, this timeframe is based on current projections and is subject to change.brbrAll other Ekahi amenities, including beach access, fitness room, Pavilion facilities, and the three remaining pools, are expected to remain open.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.brHawaii State Tax ID# 150-582-6304-01
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Exceptional(94)

$446.51

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Gorgeous condo with large private lanai, shared pool, hot tub, BBQ, and tennis

Wailea, Hawaii, United States

Wailea Grand Champions 7brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your ideal Maui retreat! Nestled in a serene setting, this spacious 2-bedroom, 2-bathroom condo is perfectly situated just a short walk from the vibrant attractions of Wailea and Kihei. With easy access to the Shops at Wailea, Gateway Center, and an array of delightful restaurants, you'll find everything you need for an unforgettable vacation right at your fingertips. Plus, the renowned Ulua Beach, known for its exceptional snorkeling, is just minutes away!brbrStep inside to discover a beautifully designed interior that caters to your every need. The two primary suites boast a luxurious king-size bed, ensuite bath, and large flat screen smart TV, making it perfect for couples or families traveling together. For additional guests, the living room offers a queen-sized pullout sofa sleeper, providing ample space for everyone.brbrThe well-equipped kitchen is a culinary haven, complete with quartz countertops and all the essentials, including a blender, rice cooker and slow cooker. Enjoy your meals indoors or take them outside to the expansive lanai, where you can soak in stunning views of the lush and surrounding landscape —ideal for sipping morning coffee or unwinding with evening drinks. brbrFor beach enthusiasts, this condo is a dream come true! It comes stocked with beach chairs, an umbrella, and boogie boards. After a day of sun and surf, relax in one of the two pools or hot tubs, or take a leisurely stroll along the scenic golf course walking path. With so much to offer, this Wailea condo is the perfect base for your Maui adventure!brbrTHINGS TO KNOWbrbrEach room has a ceiling fan and air condition unit.brThis condo is located on the 2nd floor, there are 8 steps to walk up.brThis property is managed by Vacasa Vacation Rentals of Hawaii LLC.brbrParking notes: There is free parking available for 2 vehicles.brThis rental is located on floor 2.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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Home Most popular vacation rentals in Wailea

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Exceptional(94)

$3135.26

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ULTRA LUXURY SOLARA LUXE POOL VILLA D101, NEWLY RENOVATED, SLEEPS 8!

Wailea, Hawaii, United States

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Exceptional(94)

$2565.93

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FABULOUS FLORAL GARDENS POOL VILLA G102! PRIVATE PLUNGE POOL, LARGE YARD, SLEEPS 8!

Wailea, Hawaii, United States

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Exceptional(94)

$2710.81

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Luxury 3 Bedroom Penthouse with Panoramic Ocean Views at Wailea Beach Villas + Complimentary Rental Car! | WBV-PH505 by KBM Resorts

Wailea, Hawaii, United States

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Exceptional(94)

$2758.28

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OCEAN VIEW LUXURY, CASTAWAY COVE C201, WAILEA BEACH VILLAS!

Wailea, Hawaii, United States

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Exceptional(94)

$2773.92

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Top Floor Wrap-Around Ocean Views - PH512

Wailea, Hawaii, United States

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Exceptional(94)

$2792.72

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NEW! Luxury 3 Bedroom Penthouse with Panoramic Ocean Views at Wailea Beach Villas + Complimentary Rental Car! | WBV-PH412 by KBM Resorts

Wailea, Hawaii, United States

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Exceptional(94)

$2885.87

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Recently Renovated & Professionally Managed Ocean View Villa

Wailea, Hawaii, United States

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Exceptional(94)

$4122.13

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FAMILY FUN & LUXURY ANDAZ PENTHOUSE OCEAN & SUNSET VIEWS FROM LANAI HOT TUB 3 Br/4 Ba for 8

Wailea, Hawaii, United States

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Exceptional(94)

$3843.19

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LUXURY OCEAN & RESORT VIEWS ANDAZ w/ LANAI JACUZZI Sea Spirit 811 3Br/4Ba for 8

Wailea, Hawaii, United States

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Exceptional(94)

$3715.03

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Recently Renovated | Wrap-Around Ocean Views | Wailea Beach Villas D302

Wailea, Hawaii, United States

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