Home Vacation Rentals By Owner In Wailea, HI

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$1071.46

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Elegant Wailea Renovated 2BR Condo Panoramic Ocean and Haleakala Views Pool

Wailea, Hawaii, United States

For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly renovated 1536 square foot condo is a spectacular beachfront vacation rental with panoramic ocean views and extensive Haleakala mountain views. You will love the exquisite interior design of this home.brbrNestled inside this stunning newly redesigned condo with its light and airy modern decor you will feel yourself relax immediately. Open the glass doors in the living room to let the tropical breezes in as you unwind or take a drink outside on the multiple balconies to enjoy the spectacular ocean views. brbrYou will be welcomed by high end, hand carved mahogany furnishings throughout. The fully equipped, brand new full renovated kitchen includes all the amenities you will need for dining at home. brbrThis gorgeous condo offers two spacious light and airy bedrooms with large, comfy new California King Beds, ceiling fans and lots of storage space for all your belongings. The two spa style bathrooms will meet all your needs, including the master bathroom offering a double sink vanity. brbrThe new queen size sofa pull out couch completes the accommodations for up to 6 guests. Enjoy your own huge private lanai while drinking your morning coffee, afternoon tea, or evening glass of wine while watching the gorgeous red, orange, pink and blue hues of a breathtaking Hawaiian sunset. You may never want to leave.   brbrThis oceanfront complex offers full gazing out at the azure waters of the Pacific Ocean. Amenities includes two oversize pools with ample lounging to soak up the sun and a full size kitchen and bbq grills to cook a memorable meal just outside the pool! A tennis court, unique fitness center, and beachfront walking path access, so you don't have to miss out on your morning workouts!  brbrSituated right in the heart of Wailea Elua Village, a premium property location right on the beach in Wailea, the hottest town on the island, and offers over 24 acres of exquisite landscaping, luxury experience and million-dollar ocean views. This property is located right in the center of Wailea on South Maui's gorgeous sunny ocean shores. The complex is located on white sandy Ulua Beach, one of Wailea's superior snorkeling and dive beaches and is adjacent to Wailea's award winning Blue Golf Course nearby the Shops at Wailea.brbrROOM AMENITIESbrSmoke Free environment, NEW Central AC, Free WiFi, Fully Equipped Kitchen (Cooking range/oven, Refrigerator, Dishwasher, Microwave, Blender, Coffee maker, Dishes & Silverware) A variety of Cable Channels, Smart TV Apps, Ceiling fans, Private lanais, Iron and ironing board, Additional linens and towels, In Unit Washer/Dryer, Laundry detergent, Bath amenities, Hair dryer, Own private garage, Beach gear (beach chairs, beach towels, a cooler and a beach umbrella) and Laptop Friendly Space.brbr*This property is not handicap accessible and the property is only accessible by staircase, there is no elevatorbrbrHawaii Tax I.D. GE-060-449-0240-01 Tax Map Key 210080700006
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Exceptional(3)

$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(109)

$2130.88

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Stunning Ocean View Wailea Beach Villa- Book & Save

Wailea, Hawaii, United States

Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect . 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spectacular panoramic ocean view. This elegant 4th Floor Villa is nestled between The Grand Wailea & The Shops at Wailea. Almost 3000' with lanai, 9' ceilings, Oversized comfy plush sofas, a gorgeous Baby Grand piano, beautiful art, extensive granite & marble & most comfortable bedding. Enjoy the open space floor plan that stretches from the huge living room, large dining area off the gourmet kitchen. Magnificently furnished to include every detail for the sophisticated traveler. In addition to the Baby Grand Piano in Living Room, enjoy a 75 inch smart TV. The kitchen has a Sub-Zero fridge and Sub-Zero Wine Cooler. Enjoy the Viking Grill for outdoor sunset dinners on your lanai. There are 55-75 smart TVs, Blu-ray Players and iPod Docks in bedrooms, PlayStation 4, washer/dryer, soft linens, toiletries, private underground parking & elevator, lobby check-in, concierge, & housekeeping. Full Fitness Center, 2 pool/spas & billiards. brbrThis luxury villa can accommodate up to 8 adults with space for a toddler or infant in one of the two master bedrooms. An additional guest fee applies for each guest over a party of 8.brbrThis Villa has been rated by guests as Perfect! After a few days in the water and relaxing on the beach, you may be ready for something different. One of the most exceptional collections of shops in all Hawaii is The Shops at Wailea. This world-class shopping mecca provides access to cultural, entertainment, and shopping activities. The venue for an internationally celebrated film festival, it's not unusual to see world famous film stars.brbrThe Shops at Wailea hosts a number of activities appealing to everyone in your family. Shopping nirvana can be reached when you browse through stores like Louis Vuitton, Tiffany & Co., Fendi, Gucci, and Coach, along with many one-of-a-kind island stores offering rare treasures.brbrThis center offers many dining options at excellent restaurants like Tommy Bahama's or Ruth's Chris Steak House. Your family will delight in the hula entertainment on a regular basis at The Shops. The children will enjoy watching artists and Lappert's Ice Cream.brbrThe most beautiful drive you'll see: If ever there was a perfect example of the saying, 'Getting there is half the fun,' it has got to be the adventure to see the secreted-away rain forest village of Hana.brbrYou've undoubtedly heard about this remote town, and its unique isolation far from any other city, town or village on the island of Maui. A visit from oceanfront condos, Wailea Beach, requires at least a three hour drive to get there, but is well worth the journey.brbrWhat makes this drive so unique are the more than sixty bridges you will cross on the sixty mile journey through lush rain forest from your Maui villa. While it is drive-able within three to four hours from southern Maui oceanfront condos, villas and hotels, you'll want to stop along the way and spend time taking in spectacular views from many scenic vantages along the way. To really get the most from this adventure, you may want to consider an overnight stay in the town of Hana itself. Don't miss Haleakala Volcano, Maui's most fascinating site.brbrWhy Wailea Beach, Luxury, Entertainment: As with any real estate selection, the most important aspect of choosing a vacation rental is location, location, location.It's funny to think that on an island as exquisite as this, some Maui oceanfront villas can have location advantages over others. But they do. Wailea Beach itself held the title 'Most Beautiful Beach' in 1999.brbrOne way to feel confident about a particular area's attractiveness as a vacation spot is the existence of luxury hotels and spas. Owners of these properties research areas diligently prior to building, so you can take advantage of their legwork. brbrWailea Beach is a favorite place with tourists, graced with a gorgeous shoreline, this area is home to three top-tier hotel resorts, and boasts spectacular Maui vacation villas and condos and offers the same level of amenities and services as their nearby spa hotel neighbors with a lot more room. brbrThis Maui Condo Penthouse Villa beats the hotel alternatives in terms of luxury, cost, convenience and comfort. Once you stay, you will be a repeat guest for life!
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Exceptional(11)

$2506.95

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UBER LUXE SERENITY HOUSE POOL VILLA D102, LARGE YARD, NEWLY RENOVATED, SLEEPS 8

Wailea, Hawaii, United States

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$889.32

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Wailea Perfection - Professionally Managed

Wailea, Hawaii, United States

Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and convenience for an unforgettable stay in paradise. Upon entering, you'll be welcomed by a spacious, open living area, tastefully furnished for a relaxed ambiance. The living room offers plush seating and a flat-screen TV, perfect for unwinding after a day of island exploration.br br The fully equipped kitchen is a chef's delight, featuring modern appliances, generous counter space, and all the necessary utensils for preparing delicious meals. Enjoy your culinary creations at the elegant dining table, or opt for an al fresco dining experience on the private lanai, where you can relish your meals while taking in stunning views of the lush tropical landscape and ocean.br br The primary bedroom boasts a king-size bed, a private en-suite bathroom, and a smart TV. The second bedroom also features a king-size bed and its own en-suite bathroom with a tub, and both bathrooms are equipped with refreshing rain showerheads.br br Situated in the prestigious Wailea area, this residence is just steps away from world-class beaches, renowned golf courses, and upscale shopping and dining options. Spend your days lounging by the pool, soaking up the sun, or exploring nearby attractions like the scenic Wailea Beach Path or the iconic Molokini Crater.br br Important Things to Note for Wailea Grand Champions Villas 52:br 1,056 Sq. Ft. garden view vacation condo on the second floorbr 2 bedrooms and 2 bathrooms, with bedding arrangements of 2 kings br Full kitchen with stove, oven, microwave, refrigerator and dishwasherbr Coffee maker, blender, rice cooker and toasterbr Kitchen cookware and utensilsbr TVs with standard cablebr Wi-Fi internet, in-unit laundry facilities, and window mounted air conditioningbr br Platinum Rating:br Property is both inviting and stylish, including contemporary design motifs, high quality appointments, and upscale furnishings.br br Nearby Attractions:br Wailea Beach: Drive in 3 minutesbr Wailea Town Center: Walk in 5 minutesbr Wailea Tennis Center: Walk in 5 minutesbr Shops at Wailea Dining & Shopping: Drive in 3 minutesbr 3 Wailea Golf Club Courses: Drive in 5 minutesbr br This residence is professionally managed by CoralTree Residence Collection. Guests staying in this vacation rental can expect the elevated guest services, quality standards and comforts associated with a best-in-class hospitality company that maintains a collection of more than 50 resorts, hotels, and condo communities across the nation. Our dedication to excellence in hospitality can be seen in our:br - Hassle free in-person guest check-in location.br - Professionally trained and managed in-house housekeeping teams that use industry leading techniques, tools, and products.br - On-island guest service teams available via phone or text to immediately respond to any guest needs. br - Our maintenance and engineering team can also be dispatched promptly to repair any malfunctions if they occur in the residence. br - Superior bedding, linens, towels, and bath products you would expect when staying with a luxury property. br - On-island concierge services to assist with guidance and booking of local activities.
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$492.61

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Bright & Colorful Beach Condo at Wailea Ekahi

Wailea, Hawaii, United States

Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the comforts of home paired with the unparalleled amenities and breathtaking natural beauty that define the Wailea experience.br From the moment you step inside, you're enveloped in a sense of tranquility, with the unit's open floor plan, high ceilings, tropical furnishings and large windows allowing natural light to flood the space. The living area is adorned with plush, modern furnishings, perfect for relaxing after a day spent basking on the nearby golden sand beaches or exploring the lush, tropical landscapes. The fully-equipped kitchen is a chef's dream, featuring new appliances, granite countertops, and all the cookware and utensils needed to prepare delectable island-inspired meals. And when it's time to retire for the evening, the spacious bedroom offers a private oasis, with a sumptuous king-sized bed and direct access to a second lanai. br Throughout the property, attention to detail is evident, from the elegant decor to the top-of-the-line linens and amenities. But perhaps the crown jewel of Wailea Ekahi 52 is its prime location, situated just steps from the community's sparkling swimming pools, hot tubs, and pristine tennis courts, while also providing easy access to the world-class Wailea Beach, acclaimed restaurants, and championship golf courses that have made this slice of Maui so renowned. br br Important Things to Note for Wailea Ekahi Village 52D:br 800 Sq. Ft. garden view vacation condo on the second floorbr 1 bedrooms with 1 bathroom, with bedding arrangements of a king bed and a sofa bedbr Full kitchen with stove, oven, microwave, refrigerator and dishwasherbr Coffee maker, blender, rice cooker and toasterbr Kitchen cookware and utensilsbr TVs with standard cablebr Wi-Fi internet, in-unit laundry facilities, and air conditioningbr br Silver Rating:br Comfortable accommodations with a consistent style throughout that may not exhibit elevated finishing touches.br br Nearby Attractions:br Keawakapu Beach: Walk in 3 minutesbr Wailea Beach Path: Drive in 5 minutesbr Uua Beach: Drive in 5 minutesbr Shops at Wailea Dining & Shopping: Drive in 5 minutesbr 3 Wailea Golf Club Courses: Drive in 5 minutesbr br This residence is professionally managed by CoralTree Residence Collection. Guests staying in this vacation rental can expect the elevated guest services, quality standards and comforts associated with a best-in-class hospitality company that maintains a collection of more than 50 resorts, hotels, and condo communities across the nation. Our dedication to excellence in hospitality can be seen in our:br - Hassle free in-person guest check-in location.br - Professionally trained and managed in-house housekeeping teams that use industry leading techniques, tools, and products.br - On-island guest service teams available via phone or text to immediately respond to any guest needs. br - Our maintenance and engineering team can also be dispatched promptly to repair any malfunctions if they occur in the residence. br - Superior bedding, linens, towels, and bath products you would expect when staying with a luxury property. br - On-island concierge services to assist with guidance and booking of local activities.
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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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$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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$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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$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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$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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$2758.28

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

Wailea, Hawaii, United States

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$2773.92

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Top Floor Wrap-Around Ocean Views - PH512

Wailea, Hawaii, United States

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$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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$2885.87

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Recently Renovated & Professionally Managed Ocean View Villa

Wailea, Hawaii, United States

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$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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$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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$3715.03

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

Wailea, Hawaii, United States

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