Home Vacation Rentals By Owner In Wailea, HI

Showing 360 Of 450 Vacation Rentals
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$538.06

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Luxury Wailea Family Condo. Complete Remodel! AC and Pool.

Wailea, Hawaii, United States

Your Perfect Maui Family Retreat AwaitsbrbrExperience the ultimate in modern luxury at this completely renovated condo in Wailea. Just a 10-minute stroll to the pristine shores of Keawakapu Beach and moments from the elegant Shops at Wailea, this impeccably appointed condo offers everything your family needs for an unforgettable Maui vacation.brbrWhy Guests Love This PropertybrbrBRAND NEW EVERYTHING - This isn't just updated; it's completely transformed with renovations throughout. From the flooring to the furnishings, every detail has been thoughtfully designed for your comfort and convenience.brbrTRULY FAMILY-FRIENDLY - As parents of two children, we designed this space with families in mind. We want to help make your vacation as stress-free and enjoyable as possible. brbrPEACEFUL & PRIVATE - Unlike many units at The Palms, this quiet retreat doesn't back up to the main road. Enjoy serene views of lush tropical landscaping from your spacious 475 sq ft lanai.brbrFULL AIR CONDITIONING - Stay cool throughout your entire stay! While some Palms units only have AC in the master bedroom, we've installed deluxe AC units in the living room, master bedroom, AND second bedroom.brbrThe SpacebrMaster Bedroom Suitebrbr-King bed with premium mattress and luxurious linensbr-Fully remodeled en-suite bathroom with low-profile tub (perfect for bathing kids)br-Cable & Smart TVbr-Blackout curtains for restful sleep and jet lag recoverybr-AC unit + ceiling fanbr-Spacious closet and 6-drawer dresserbr-Peaceful tropical greenery viewsbrbrSecond Bedroom (Fully Private!)brbr-Two twin XL beds that can be converted to a king bedbr-Completely walled-in with door (not sliding doors like many Palms units)br-Adjacent full 2nd bathroom with showerbr-Smart TV with streaming capabilitybr-AC unit + ceiling fanbr-Blackout curtainsbr- ClosetbrbrLiving Areabrbr-Queen memory foam sleeper sofa (5-inch mattress for actual comfort!)br-Cable & Smart TV - access your Netflix, Amazon Prime, or Hulu accountsbr-Blackout curtains for privacy when couch is in usebr-AC unit + ceiling fanbr-Opens to spectacular 475 sq ft lanaibrbrGourmet Kitchenbrbr-Completely new modern appliancesbr-Fully stocked with cookware, dishes, and utensilsbr-Kitchen window opens to lanai with bar seating - no one gets stuck inside while cooking!br-Kid-friendly dishes, cups, and cutlerybrbrExpansive Lanai (475 sq ft)brbr-2 lounge chairs for ultimate relaxationbr-Outdoor dining table for sixbr-2 bar stools at kitchen pass-through windowbr- Lush, tropical viewsbrbrbrEverything You Need for Beach DaysbrbrWe've got you covered with a complete collection of beach gear:brbr-Beach chairs & umbrellabr-Cooler & beach bagbr-Snorkel sets & boogie boardsbr-Sand toys & life jacketsbr-Beach towelsbrbrbrFamily-Friendly Amenitiesbrbr-Pack-n-play with REAL mattress and bedding (happy baby = happy vacation!)br-Kids' dishes, cups, and cutlerybr-Sand toys and life jacketsbr-Low bathtub in master bathbr-Short walk to resort poolbr-Convenient parking directly in front of unitbr-In-unit washer & dryer with complimentary supplies (no quarters needed!)brbrResort Amenitiesbrbr-Stunning oceanview resort-style pool and hot tubbr-Immaculate grounds with tropical landscapingbr-Perfect sunset viewing areabr-10-minute walk to famous Keawakapu Beach (incredible snorkeling!)br-Short drive to world-class golf coursesbr-Less than a mile to The Shops at Wailea and Island Gourmet MarketbrbrbrModern Conveniencesbrbr-High-speed WiFi (5G & 2G networks available)br-Smart TVs in all rooms - log into your streaming accountsbr-Cable TV in living room and master bedroombr-Complimentary long-distance calling (US & Canada)brbrbrPrime Location Benefitsbr✓ Quiet unit - does NOT back up to main streetbr✓ 2nd floor location with tropical greenery viewsbr✓ Steps from parkingbr✓ Short stroll to pool and hot tubbr✓ 10-minute walk to Keawakapu Beachbr✓ Minutes to Shops at WaileabrbrSleep Accommodationsbrbr-Sleeps up to 6 guests comfortablybr-Master: King bed (premium mattress)br-Second bedroom: 2 twin XL beds OR convert to kingbr-Living room: Queen sleeper sofa (5 memory foam)br-All rooms have blackout curtains for quality restbrbrbrGood to Knowbrbr-Second floor unit (not handicapped accessible)br-Unit #704 - I own two other nearby units if you're traveling with a larger groupbr-All-new high-quality linens and towelsbr-Fresh decor and art throughoutbrbrbrThe Palms at Wailea ExperiencebrbrThe Palms at Wailea is renowned for its impeccable grounds, serene atmosphere, and prime Wailea location. Perched above the pristine shores of Keawakapu Beach, this boutique complex offers the perfect blend of luxury, tranquility, and convenience. Whether you're snorkeling at the beach, shopping at Wailea's elegant boutiques, or simply relaxing on your private lanai, this is the Maui vacation you've been dreaming of.brbrBook with confidence knowing every detail has been thoughtfully designed for your family's comfort and enjoyment!brbrDiscounts possible for stays over 30 days.brbr*Please note after May 3rd, 2024 the County Of Maui no longer allows grills in the lanai. There are central grilling stations throughout The Palms of Wailea complex for guests to use. brbr**All people without regard to race, religion, culture, ethnicity, gender, gender identity, or sexual orientation are welcome in our home.**brbrTransient Accommodations Tax Certificate of Registration for Hawaii Tax ID Number: TA-210-485-3504-01brbrHawaii General Excise Number: GE-210-485-3504-01
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Exceptional(41)

$484.48

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Beachfront condo w/ ocean views and private lanai

Wailea, Hawaii, United States

Welcome to Wailea Ekahi 34B where lush tropical foliage surrounds you and views of the majestic Pacific await! This updated 1 bedroom / 2 bathroom unit is the perfect setting for your Maui vacation. This ground floor unit boasts incredible ocean and garden views! Enjoy the sunset views and feel the breeze from the oversized private lanai! Your private lanai stretches across the living room to the primary bedroom where your private oasis awaits. The outdoor dining furniture and lounge chairs make the perfect setting for pupus (appetizers) and your favorite beverages while enjoying the ocean view.brbrThe living room is spacious with tile floors and flows out to the lanai to enjoy the indoor/outdoor living area where you can grill on the lanai with the stunning ocean views! The outdoor dining table with seating for up to four people is ready for al fresco dining. The dining room inside has seating for four people with an updated kitchen ready for your family chef! The living room is complete with a queen-size sofa sleeper and has a guest ensuite bathroom as well. The primary bedroom is your own private oasis with a king-size bed, beautifully renovated ensuite bathroom, and direct access to the lanai. It is the perfect way to start and end your day with the gorgeous ocean view!brbrWailea Ekahi Village Located in the heart of Wailea, Ekahi offers 4 swimming pools set in beautiful gardens, including a large beachfront pool and pavilion for sunsets and beachfront dining. Wailea Ekahi no longer allows private grills but they offer a beautiful gas grilling area at the community Pavilion. The pavilion provides direct access onto Keawakapu Beach, Ulua, and the world-famous Wailea beaches are a short walk along the beach path. These three beautiful white sand beaches are perfect for beach walks and family beach days.brbrWalk along the beach path to the Wailea Shops and Tennis Club and five of the most prestigious hotels of Wailea. The Fairmont, Four Seasons, Grand Wailea, Wailea Marriott Resort and Spa, and The New Andaz Hotel are a few minutes walk along the promenade. You can enjoy the sunset, see whales in season, access beach activities like paddle boarding, and stroll to dinner and back along the lighted promenade.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.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.brbr*Split A/C in Living Room and Primary Bedroom*brNotice as of 8/5/2025: Please note that due to long-term parking limitations near buildings 34 and 35, only one parking stall is allotted for Unit 34B. This will be in effect for approximately two years.brbrAlternate parking is available near Buildings 37 and 38 for any additional vehicles.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.brbrHawaii State Tax ID#: 074-566-8608-02
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Exceptional(9)

$336.03

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Wailea Garden-View Condo – Lanai, A/C, New Furnishings & Near Golf

Wailea, Hawaii, United States

*New Furniture throughout!! This two-bedroom, two-bath garden-view condo has just been remodeled with all new furniture throughout each room in the condo. The primary bedroom and the guest bedroom both have Cal-King beds plus the living includes a queen sofa sleeper allowing this unit to sleep up to six guests. This ground-floor unit is tiled in all of the common areas and carpeted in the bedrooms. The living area is a great place to entertain and hang out with friends and family. This unit has wireless internet. Enjoy close proximity to all Wailea has to offer including Golf, Shopping, and Dining. brbrBrand new high-end furniture package throughout the entire condo as of Jan 2023 which included Jefferson Plush Cal-King mattresses.brbrThe primary bedroom features a microwave and a new mini-fridgebrbrNew table and four new chairs to the lanai which allows for outdoor seating for 7brbrCooling features: (1) Window AC unit in each bedroom + ceiling fansbrbr**Please note there are 8 steps down to the entrance of this condobrbrResort Amenities: brPool: 2 brHot tub: 2 brBBQ Area: 2 brLaundry: In unit brElevator: NONE brGolf and Tennis privileges ($$) brbrTransit: Renting a car is recommended. Alternate transport includes Private airport shuttles ($$), Lyft, Uber, Public Bus.br brRestaurants Nearby:  br• Matteo’s Osteria: Italian br• Lineage, by Chef Sheldon: Gourmet island favorites br• Cheeseburger in Paradise br• Tommy Bahamas br brShopping:  brShops at Wailea (2min): br• Island Gourmet: deli, grocery and souvenir br• Local and designer retail options br• SOHA island living – Home furnishings br brPiilani Shopping center (10min): br• Safeway grocery store br• Outback Steakhouse br• Food Court (Subway, Coldstone creamery, etc.) br brBeaches:  br• Ulua Beach (5min drive) br• Makena Beach (15min drive) br• Polo Beach (5min drive) br  brLocal Activities: Snorkeling, surfing, whale watching (In Season), skating rink at Kalama Park.  brbrGolf: Maui Nui Golf Course, Wailea Golf Club (3 courses) brbrActivities concierge service provided. br• Maui Ocean Center distance br• Maui Tropical Plantationbr• brbr30+ min drive upcountry br• Kula Ali'i Lavender Farm br• Ocean Vodka Organic Farm & Distillerybr• MauiWine Winery br• Surfing Goat Dairy br• Piiholo Ranch Ziplinebr brDistance to Airport: 16 miles, approximately 26 minutes brbr**Not ADA accessiblebrbrTAT# 135-407-6160-01brTMK: 210081040033
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Exceptional(30)

$548.12

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Private Vacation Home

The Palms 1202 Huge Ocean Views

Wailea, Hawaii, United States

Wailea (Maui) Luxury Vacation Rental -brbrOur favorite unit.brbrbrbrWelcome to the highest sales price unit at The Palms at Wailea. The Palms 1202. The reason is simple. It has the best and widest ocean and garden views in the complex. This spacious top floor unit features an expansive living room with 18 foot vaulted ceilings filled with light and endless vistas. Step inside and enjoy the sweeping ocean view from Lanai to Molokai from the comfort of the master bedroom, living room, lanai, and kitchen. A new A/C system was installed, new $70,000 bathrooms in 2024 to ensure you a comfortable stay. The second bedroom features a new king bed set. Just steps away from the wonderful snorkeling beaches of Wailea at Keawakapu Beach. On premise ocean view infinity pool and jacuzzi. Enjoy the sunset from your lanai or living room 365 days a year. Accommodates 4 guests very comfortably. Special discounts for extended stays - contact us to learn more. 2024 BBQ NOTE: Recent fire regulations have required removal of the individual BBQ's on the lanais. There are now community BBQ's instead.brbrPLEASE NOTE DUE TO CURRENT FUEL COSTS HAWAII ELECTRIC costs have gone up 40% in the past 2 months. Because of this there will be a daily surcharge  of $9.50/day to cover this amount. brbrbrbrBookings over 1 year away please confirm rates.brbrMahalo from Palms of Wailea!brbrbrbrPlease note that if a credit card is used for payment - processing fees are paid by the guest. We offer alternative options for payment to avoid this 3% charge. Non USA credit cards are 3.5%. (We get charged 4.5%).brbrContact info :(blocked)
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Exceptional(16)

$490.34

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Golf course-front condo with outdoor pool, hot tub, central AC, & free WiFi

Wailea, Hawaii, United States

Wailea Grand Champions 149brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEnjoy your very own paradise on earth at this family-friendly, golf course-front condo! It's perfect for a family escapade or a beach retreat with your friends. Inside, this condo comes equipped with a fully-equipped kitchen boasting all the appliances and cooking essentials to prepare the most delicious meals or even try that recipe you like the most, a dining table to seat everyone, an inviting living space with comfortable sofas and a large TV, and a private balcony with an outdoor dining area overlooking the nearby golf course. Start your day with tropical juice and fruit on the balcony and get ready to experience the getaway of a lifetime. By booking this retreat, you and your friends will be granted access to shared gas grills, an outdoor swimming pool, and even a hot tub.brbrSitting only one mile from Wailea Beach, known as one of Maui's premier beaches and a fantastic snorkeling and SUP spot, beachgoers and water sport enthusiasts will have a great time here! The Shops at Wailea features national high-end shops, local retailers, and Maui musicians, and you can find it half a mile from your condo. brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brBeach towels are provided.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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Exceptional(52)

$429.74

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Wailea Ekahi #16-C Ground Floor Unit Near Keawakapu Beach, Wifi, Full A/C

Wailea, Hawaii, United States

Wailea Ekahi #16-C is a 1 bedroom, 2 bath oceanfront ground floor unit. It has a huge ocean view, split system A/C throughout, a fully-equipped kitchen, and washer and dryer. There are 2 flat-screen TVs and free Wifi. There is a king bed in the bedroom and a twin murphy bed in the living room. Both the master bath and guest bath feature walk-in showers (no tubs). For outdoor activities, Wailea Ekahi #16-C 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. Sleeps up to 3.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 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 pavilion 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 Notice: 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. **
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Exceptional(45)

$349.05

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Palms at Wailea #307 Beautifully Remodeled, Ground Floor Unit, Ocean View

Wailea, Hawaii, United States

Palms at Wailea #307 is a beautifully spacious 1Bd/2Ba unit with all the comforts of home! It is conveniently located on the ground floor and it is a close walk to the picturesque resort pool. The unit has split system A/C in the bedroom. The beautiful kitchen is equipped with top of the line appliances and granite countertops, and is supplied with all your vacation needs in mind. The bedroom has a king bed and the en suite bathroom is remodeled with a luxurious whirlpool bath. The convenient second bathroom boasts a beautiful travertine walk-in shower. The living room includes a queen sleeper sofa and a large-screen television. You can access the spacious, well-appointed lanai through either the slider in the living room or the one off the bedroom. You can see the ocean as you relax on the lanai. For your outdoor enjoyment, this Palms at Wailea #307 is supplied with beach chairs and beach towels. A telephone is supplied in the unit with free calling to the continental U.S. and to Canada. There is also a washer and dryer in the unit. Sleeps 4.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.brThe fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is a large pool and hot tub that is perfect for sunbathing and has a magnificent view of the ocean from the pool area. We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book Maui Revealed and their website. These properties were chosen because of their superior quality and great rates!br** Important Notice: The pool area will be closed Sept. 15-18, 2026, for annual maintenance. The nearest white sandy beach is a short 2-minute drive or 10-minute walk from the Palms at Wailea entrance. **
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Exceptional(51)

$701.99

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NEWLY UPDATED-SLEEPS 8-WELL EQUIPPED-AC-METICULOUS CLEANING

Wailea, Hawaii, United States

Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that has been nicely updated. 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 #160br-Ocean And Garden Viewsbr-Quiet Location Backing Onto Golf Coursebr-Cabinetry With Granite Countersbr-Luxury King Bed In Master Bedroombr-Queen Bed In The Second Bedroombr-Queen Bed In The Third Bedroombr-Pullout Queen Sectional 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-4 Large Flat Screen, Smart TV'sbr-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.brbrHI Tax ID#: TA-210-575-4624-01brbrWe Accept Visa And MasterCardbrbrTo Reserve The Condo, We Take A $400.00 Deposit And The Balance Is Due 30 Days Prior To Your Arrival.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.
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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

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.brbrWailea Beach Villas 412 represents the epitome of luxury and Hawaiian charm. This penthouse unit is a stunning example of modern aesthetics fused with traditional Hawaiian style. The kitchen features custom monkeypod cabinets and elegant countertops, creating a striking culinary space. With three spacious bedrooms and three bathrooms, the penthouse villa offers ample space for families or groups, providing the perfect combination of comfort and style.brbrThe unit boasts unbeatable panoramic views of Wailea beach, with sweeping vistas of the beach and the surrounding area. The master bedroom features a king-size bed, while the other two bedrooms each have a queen-size bed, providing comfortable accommodations for everyone. Whether relaxing in the living area or enjoying the view from your private lanai, you'll find the villa's layout ideal for both relaxation and entertainment.brbrLocated just moments from The Shops at Wailea, the villa offers easy access to a variety of shopping and dining options. Wailea Beach Villas 412 is a true masterpiece of modern Hawaiian living, combining luxury and convenience in an ideal location. This penthouse unit provides the best of both worlds - a peaceful retreat and a vibrant area full of activities and amenities at your fingertips.brbrWhether you're looking for relaxation or adventure, Wailea Beach Villas 412 is the perfect place to experience the beauty of Maui. With breathtaking views, world-class amenities, and a prime location, this villa is the ultimate Hawaiian getaway for anyone seeking luxury and style. 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 5:30 PM. brbr
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$252.55

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1 BR Treetop Wailea , 2nd floor vaulted ceilings

Wailea, Hawaii, United States

The Tree Top One Bedroom, is an elegant, bright 2nd floor unit with tropical modern king bedroom, teak and rattan furnishings, spacious bath with separate shower and tub, spacious living/dining area and well stocked kitchen and offers privacy amid tree top blooms and tropical birdsong. The sunny, lanai offers washer/dryer in the 'laundry closet' and an umbrella table for warm evening dining under the stars or breakfast coffee with the birds. brbrA/C and ceiling fans in both the living area and bedroom.brbrbrWalking Distance to Wailea Marriott, Grand Wailea, Shops of Wailea and everything along the Wailea Oceanfront Trail.brbr brMorning calm invites you to snorkel amidst the colorful coral at the edge of Ulua beach, stroll or jog along the paved shoreline path or just plant yourself in whichever of Wailea's five beaches that suits your fancy. Don't forget to keep your eyes open. During the winter season this is one of Hawaii's best walks for observing humpback whales. In the evening, sundown again draws you here for a romantic stroll, or perhaps a beachside cocktail.brbrJust a short distance from the beaches, hidden in a tropical oasis, are the Grand Champion Villas, a quiet community of well appointed apartments offering spacious, appealing accommodations. Our affordable 'Tree Top' offers a light-filled, sizeable,(approx. 790 sq ft.) one bedroom, one bath apartment with fully equipped kitchen, living/dining room and large Garden View lanai. Nearby are two pools secreted amidst Grand Champions' verdant foliage, where gas BBQ's and umbrella topped tables are available.brbrIf all of this is not enough, Wailea offers spectacular, award winning golf courses, a superb tennis facility and a multitude of fine dining options. The Shops of Wailea, offering international shops and local retailers is practically at your doorstep.brbrIn the adjacent town of Kihei, you will find everything you need; grocery stores, Hawaiian market places, and restaurants for all tastes and budgets.brbrThe Piilani Highway will easily lead you from Wailea to all of Maui's spectacular attractions. Or, you can follow the Wailea Alanui road just a few miles east, where it narrows and offers access to a variety of beaches backed only by shady Kiawe trees, a 2000 acre natural preserve of beautiful bays and Maui's most recent lava flow.brbrCome experience Wailea and Maui at our affordable ' Tree Top' one bedroom. brbrNOW WITH HIGH SPEED WIRELESS.brbrTHIS ONE BEDROOM UNIT IS APPROPRIATE FOR 2 ADULTS ONLY. ARRIVING WITH MORE THAN THE AGREED UPON NUMBER OF GUESTS FORFEITS THE RESERVATION! IT IS STRICTLY A NON SMOKING UNITbrbr+ 25% Deposit Due at Time of Reservingbr+ Full Payment Due 45 Days Prior to Arrival in Low Seasonbr+ Full Payment Due 60 Days Prior to Arrival in High Seasonbr+ Refunded within 7 days of check outbr+ Add $145 (1 bdrm) cleaning fee to ALL bookingsbr+ Check-In: 4:00 p.m. Check-Out: 11:00 a.m. NO EXCEPTIONSbr *We may be able to adjust times if there is not another guestbr arriving/departing same day...and if cleaning schedule allows.br+ Early Check-In or Late Check-Out Requires Additional Day to GUARANTEEbr+ No Discounts During Holiday PeriodsbrbrKeywords: Condominiumbr
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Exceptional(8)

$1295.82

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Private Vacation Home

New Listing Jan, Ho'olei Ocean View Villa 21-6 Remodeled Spring 2025

Wailea, Hawaii, United States

Remodel completed June 2025! See the new photos just posted!brbrThe entire home has been repainted, almost all the furniture was replaced, a lot of new beautiful art was added, and all new hardwood French oak floors were installed in the bedrooms.. We also remodeled the kids bathroom and the powder room, added new mirrors, wall coverings and televisions.brbrWe only have a few reviews so far, so please see our other Waiola Realty Ho'olei home listings for hundreds of 5-star reviews from our guests.brbrAlso, book now and get a free early check-in or late check-out if available!brbrExperience luxury and tranquility in this spacious Hibiscus floor plan, the largest at Ho'olei. Ideally situated, this villa offers stunning ocean views, unobstructed by rooftops, and unparalleled privacy with one of the most secluded yards in the community.brbrKey Features This Ho'olei home has spacious living spaces including:brbrMaster BedroombrThe Master Suite offers a luxurious retreat with a king-size bed, a cozy seating area, and a dedicated workspace. The en suite bathroom features a soaking tub, a barrier-free shower, dual vanities, and direct access to the lanai with stunning ocean views.brbrGuest Bedroom Ensuite (2) This inviting bedroom includes two queen-size beds, a private bathroom, and an HDTV, providing a relaxing and comfortable space for guests.brbrGuest Bedroom Ensuite (3) A serene escape with a king-size bed, an HDTV, and a modern en suite bathroom featuring a barrier-free shower.brbrGreat Room & Dining Area The spacious great room is designed for comfort and style, with custom furnishings, an HDTV, and seamless indoor-outdoor living through floor-to-ceiling lanai doors. The dining area comfortably seats six, perfect for shared meals and gatherings.brbrGourmet Kitchen & Outdoor Dining The chef-style kitchen is equipped with, two Sub-Zero refrigerators and freezer drawers a wolf range and oven, a Bosch dishwasher, bar seating for 5 and premium appliances for your culinary needsbrbrOutdoor Lanai The upper-level lanai has dining seating for six, lounge seating, a Wolf BBQ, and Sub-Zero mini-refrigerator.brbrIncluded Amenities This home includes fine imported designer furnishings, high-end linens, and beach essentials such as eight beach chairs, four umbrellas, a rolling cooler, a beach wagon, eight beach towels, and six gym towels to enhance your Fun in the Sun.brbrPerfect Location in Wailea!brbrCentrally located in Wailea on Maui’s sunny, leeward southwest side, Ho’olei 21-6 boasts one of the island’s most beautiful and sought-after settings. This area is the driest on Maui, with just 20 inches of rainfall annually, offering sunny days and tropical breezes year-round—even in winter.brbrThe home is conveniently situated across the street from world-class resorts like the Grand Wailea, the Fairmont, and the Four Seasons. Within walking distance, you’ll find The Shops at Wailea, the newly built Wailea Village Center, and the Wailea Gateway Center, all offering diverse dining options, gourmet markets, trendy boutiques, and local shops.brbrWailea Beach, consistently ranked among the world’s most stunning beaches, is just across the street. The much-loved Wailea beach path is perfect for an early morning walk with coffee, jog, bike or an evening stroll..brbrWhile many destinations are within walking distance, renting a car is highly recommended to fully explore Maui’s remarkable attractions.brbrResort Amenities The five-star Ho'olei Resort offers a luxurious pool surrounded by tropical landscaping with a sand beach for children. Enjoy swimming through the 19-foot waterfall, swim-in grotto, and two whirlpools hot tubs. Men’s and women’s saunas and state-of-the-art locker rooms with showers are available during your stay as well.brbrRenovation Schedule This home will undergo renovations between February and May 2025, scheduled around guest reservations. Updates will include new flooring in bedrooms, remodeled bathrooms with upgraded features, designer touches such as wall coverings, fresh paint, light fixtures, mirrors, and artwork. The renovation will also feature brand-new, extra-large ceiling fans and updated furniture.brbrOhana Services We take pride in offering you and your family (your Ohana) a unique, memorable experience. From the moment you book your stay, our team is dedicated to personalizing your time on Maui and ensuring every detail is taken care of.brbrUpon your arrival, you'll be greeted by our Concierge Eric and his warm smile, he will lead you on a tour of the resort and its beautiful amenities, including the pool, waterfalls, Jacuzzi, sandy beach area, and exercise room. He will then escort you to the villa and show you how everything works, answering any questions you may have about the home and your island experience. You will be welcomed with local snacks, desserts, coffee and seasonal fruit, as well as beauty products exclusively from L'Occitane. We supply all the linens, towels and sundries you will need in the home.brbrWe also offer the best eco-friendly cleaning services with Lolita and her team, who boast the highest standard on Maui, ensuring your home to be exceptionally clean and well stocked.brbrThroughout your stay, our team is available to help personalize your experience, whether it's booking activities, making recommendations, or accommodating any special requests you may have. From grocery shopping and delivery (upon request), to coordinating local activities, we’re here to make sure your vacation exceeds expectations. Eric, our concierge, is always available to assist you with anything you need, whether it’s about the villa or Maui itself.brbrPlease let us know what you are looking for on your Maui vacation, and we will be happy to help you make your trip to Maui more than you had expected. We hope you enjoy your stay so much that you will return and stay with us again!brbrWe have partnered with Xplorie. When you book with us you will receive promotional marketing material from Xplorie, which gives you discounts on activities on Maui up to 20% off.brbrDetails:brbrHo'olei 21-6 | Villa 3 BD/3.5 BTH (Sleeps 8)brLocation: Ho’olei, Wailea, South Maui, Maui, Hawaii, USAbrbrAccommodations:brVilla | 3 Bedrooms, 3.5 Baths (Sleeps 8)brFloor Plan: Hibiscus (largest in the Ho'olei Neighborhood)brbrTotal square footage:brbrInterior - 3,301 sq. ft.brbrLanai - 686 sq. ft.brbrGarage - 318 sq. ft.brbrTotal Area - 4,305 sq. ft.brbrNo Additional Resort FeesbrHawaii Broker’s License: RB-21415brbrGE-159-013-7344-01, TA-159-013-7344-01
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Exceptional(82)

$344.26

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Charming Wailea Ekahi Condominium

Wailea, Hawaii, United States

Our Maui vacation rental is a light and airy one-bedroom, two-bath condominium on the second floor of Ekahi's Upper Village. It comfortably sleeps four guests, with a lovely tropical garden view overlooking a quiet and peaceful swimming pool (Pool #3). You also enjoy a gorgeous partial ocean view from the pretty lanai and our well-stocked kitchen. Vaulted 15+ foot ceilings in the great room of our Maui rental create a feeling of spaciousness that belies its size. We have a hammock chair on the front lanai!brbrAlthough the interior space and lanai are only 1090 square feet, the condominium is laid out in such a way as to more than accommodate four people. You will also find it equipped with beach chairs, towels, umbrella, boogie board, many DVD's, CDs, books, WiFi, and everything else necessary for a delightful sojourn in Maui. brbrIt is a five minute walk down a greenbelt to Keawakapu Beach and the ocean -- no roads to cross! You can snorkel or jump waves to your heart's content; it is a sandy white beach about a mile long. Next to the Beach is the Ekahi Pavilion and main pool, with several gas grills, a shower and bathroom, and shuffleboard.brbrOur unit is quiet, not on the street, and you will hear the birdsongs as you enjoy all the bouganvillea, palm trees, bamboo and flowers that are within reach from our lanai. The snorkeling is fantastic right in front of Ekahi.brbrWe are being very flexible if you need to cancel or move dates during this pandemic period. Just contact me. brbrOur rates at this time are $280/night for low season (April 16-December 14) and $320/night for high season (December 15 to April 15), plus taxes. There is a new Maui County tax of 3% on transient accommodations that began on November 1, 2021. That will be added to new bookings after this date. The State of Hawaii taxes also continue to be added to your booking.brbrIf you stay less than one week, there is a small cleaning fee ($115 for you) to help us cover the departure cleaning (which for me is double that). There is a king bed in the master bedroom, and a comfortable queen Murphy bed in the great room. brbrKeywords: Condominium
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$549.71

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No Stairs, Oceanview, Fully Remodeled with Dream Kitchen Palms at Wailea 503

Wailea, Hawaii, United States

NO STAIRS INSIDE OR OUT!brbrWelcome to Palms at Wailea 503, your beautifully remodeled sanctuary in paradise! This is a two-bedroom two-bathroom condo in the prestigious Wailea Resort area. One of only three condos at the Palms at Wailea complex with NO STAIRS inside or out, this condo overlooks an immense lawn sloping towards the west, with an ocean view beyond.brbrAs local owners we inspect and take care of any cleaning and maintenance between each stay to ensure your comfort.brbrPalms at Wailea 503 comfortably accommodates up to four guests. Rest easy in the king-size bed of the master suite or opt for the twin-XL beds in the guest bedroom (convertible to a king). brbrFully Equipped Modern Kitchen: Prepare delicious meals with ease in our newly remodeled, well-appointed kitchen, featuring modern Bosch appliances, granite countertops, and ample cookware and utensils.brbrPrivate Lanai: Relax and unwind on your private 400 sq ft lanai, the perfect setting for morning coffee or sunset cocktails.brbrResort Amenities: Enjoy the Palms at Wailea's sparkling swimming pool and hot tub, surrounded by landscaped gardens and swaying palm trees.brbrEntertainment: Stay connected with complimentary high-speed Wi-Fi and enjoy your favorite shows and movies on the 65-inch internet-enabled TV.brbrBeach Gear: Take advantage of our provided beach chairs, boogie boards, cooler and beach towels for a day of seaside fun and relaxation.brbrLocal Attractions:brbrWailea Beaches: Spend your days lounging at Keawakapu, Mokapu, Ulua, Wailea or Polo beaches, where gentle waves and azure waters beckon you to swim, snorkel, or simply soak up the sun.brbrWailea Golf Courses: Tee off at one of the nearby championship golf courses, including the Wailea Blue, Wailea Gold, and Wailea Emerald courses, renowned for their stunning scenery and challenging play.brbrWailea Tennis: Get your game on at Wailea’s Tennis Club.brbrWailea Village and Shops at Wailea: Explore the upscale boutiques, galleries, and restaurants at the nearby high-end shops, where you can indulge in a day of retail therapy and gourmet dining.brbrBOOK YOUR STAY TODAYbrbrEscape to paradise at Palms at Wailea 503, where locally owned hospitality and meticulous cleanliness ensure a memorable Maui retreat. Contact us today to secure your dates and embark on a journey of relaxation and rejuvenation in Wailea!brbrPlease note that rates and availability are subject to change. Contact us for the most up-to-date information.
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Exceptional(94)

$402.78

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'Best Vacation Ever' Say Our Guests! Special May Rates

Wailea, Hawaii, United States

You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit was completely remodeled in 2020. It is immaculate, impeccably maintained and cleaned to the highest standards. This unit offers wide open living space to accommodate up to six, yet intimately relaxing for two. brbrThe large air conditioned Master Bedroom features a king-size bed and a comfortable sitting area within the Master Bedroom for reading or relaxing plus a large flat screen HDTV television. The large Master Bath features a double vanity, walk in shower and separate spa bathtub. The Second Bedroom features two twin-size beds (which can be converted to a king configuration), separate entry, air-conditioning, love seat sofa (which will fold out to a full size bed, to accommodate larger guests with larger families) large flat screen HDTV television, dresser drawers and closet. The Living Room is luxuriously furnished and spacious, fully air conditioned, with views overlooking the tropical flora and the first of two swimming pools/spas at the Grand Champions Resort. Also included is a large flat screen HDTV television. The Dining Area is spacious and features table and seating to accomodate up to six people. brbrThe Kitchen features all brand new stainless steel appliances (fully remodeled in 2020) including dishwasher, drop in range, microwave and side by side refrigerator with filtered water and ice in the door, and a brand new granite counter top which wraps around the kitchen area, leaving ample kitchen working space. Brand new wood cherry cabinets are filled with everything to make your stay complete, from bone china dishes, glassware, everyday dishes for simple living (all dishwasher safe), all utensils and cookware to make your stay comfortable. You will find everything you could ever want in this villa, with all the amenities of your own home. Literally, all you need is your roll on suit case.brbrOn the Lanai, there is a full size high efficiency washer and dryer. Of the latest design, it will sense the size of your load and can even accommodate up to 20 towels. Washing your laundry is so simple (with all laundry soap provided), I literally go with a roll on, and leave myself room to come back with gifts and souvenirs from my trip to the beautiful island of Maui.brbrIn 2020, a Mitsubishi Split Air Conditioner was also added for your comfort and convenience. No more noisy air conditioners to wake you in the middle of the night. This Split Air System is the top of the line, quiet and designed to operate at your perfect, preferred temperature.brbrThe Master Bath features a brand new walk in glassed shower with two shower heads, with a relaxing, full size jetted spa for private relaxation. The Master Bath also features brand new fixtures, and new granite counter tops, and two sinks for easy access for couples. Complemented by brand new wood cherry cabinets, sinks and stainless steel fixtures, it is luxury at its finest.brbrbrLocated in the prestigious area of Wailea, the Villas are within walking distance to some of the most pristine beaches of Maui, five star dining restaurants, and delightful shopping. This complex is Grand Champion Golf and Tennis Villas, because it is surrounded by the Wailea Blue Course (one of three luxurious resort golf courses), and the Wailea Tennis Center which features about 12 private tennis course (The golf courses and tennis court which can be booked by Grand Champion Golf and Tennis Villa guests at a discounted price). Luxurious, relaxing, a peaceful getaway, together with delightful comfort will be yours in this lovely vacation villa!brbr(There is a 2 week minimum for the holiday period)brbrKeywords: Condominium
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Exceptional(130)

$753.82

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14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!

Wailea, Hawaii, United States

Wailea Ekahi #14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this condominium home! You will feel like you are on top of the world as you look out from the second floor onto the Greenbelt and over the blue Pacific Ocean. Enjoy a spectacular sunset every night.brbrThe master bedroom suite has a secluded lanai surrounded by trees and views of the Haleakala mountainside. The bedroom is furnished with a King size bed, flat-screen TV and is air-conditioned.brbrThe living area includes plantation style shutters, flat-screen TV, free wireless internet and quiet air conditioners that are easily controlled by the touch of a button to keep you comfortable all year round.brbrThe recent remodeled kitchen has beautiful granite counters, stunning cabinets with quiet touch close, and new appliances. There is a gas barbecue grill on the lanai, and beautifully tiled showers in both bathrooms.brbrWailea Ekahi Village boasts 34 tropical landscaped acres bordering one of Maui's best soft sandy beaches - Keawakapu Beach. A short 2 minute walk to Wailea Ekahi's large main pool, pavilion and beach or take a dip in the adjacent quiet pool! There are a total of 4 pools on property! Whale watching can be enjoyed right from the condo December to April each year.brbrFor more information, check out our website: https://www.mauisunsetescapes.com/brbrPrivate damage insurance required; $10.000 minimum limit.
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$461.49

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You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.

Wailea, Hawaii, United States

ALOHA!brbrStart your day with coffee and beautiful ocean views from the lanai, and finish the day watching amazing sunsets!brbrImmerse yourself in the warmth of Aloha at Our Maui Condos - Ho'okipa at Wailea Ekolu Village. Discover the true meaning of Hoʻokipa, which means hospitality, at our exceptional Wailea Ekolu home. Enjoy breathtaking Maui sunsets with panoramic views of Molokini and Kahoolawe.brbrOur condo is located on the ground floor of the HIGHLY DESIRED building #3 of Ekolu Village and includes the following:brbr• FREE local and long distance calls to the US mainland Canada & Mexico. br• FREE and secure highspeed internet br• SMART TV including streaming apps NETFLIX, HULU, AMAZON and more! br (Must have your own account for each company to login).br• Bedding & Bathroom supplies: linens, beach towels, bath towels br• Kitchen supplies: paper towels, dish soap/sponge, trash bags,br• Washer/dryer, laundry detergent, tissues, iron/boardbr• A/C in living room and bedroombr• In-room safebrbrCheck-in is 3:00pm. Check-out is 11:00am. Late check-out is available for ½ the nightly rate +tax up to 7:00pm (available from May-October only so please plan accordingly).brbrExperience the perfect getaway at our comfortable 1 bedroom, 2 bathroom condominium, located right on the 10th hole of the championship Wailea Blue Golf Course. Enjoy the comfort of stylish furnishings and modern amenities, including a remodeled kitchen and bathrooms equipped with new appliances and elegant granite. brbrUnwind on the spacious lanai, ideal for morning breakfasts, afternoon cocktails, or evening dinners with breathtaking ocean views and stunning sunsets. Plus, this unit features one of the few lanais that leads out to a large, open grassy area—perfect for relaxation and outdoor fun.brbrFully stocked kitchen with all of the amenities of home include:br• Refrigerator with water dispenser and ice maker. br• Oven/stovebr• Dish washer/soapbr• Hot water dispenser br• Rice cooker, blender, toaster/toaster oven coffee maker, coffee grinder and more!brbrYou'll enjoy indoor or outdoor dining all day long under the COVERED LANAI. brbrThe living room includes the following amenities:br• Queen size sleeper sofabr• Living room TV with DVRbr• CD player with collection of discsbr• Bluetooth speakerbr• Reading library for your enjoymentbrbrEn-suite bedroom/bathroom includes: br• Cal King-bedbr• Flat screen TVbr• Charging station for your electronicsbr• Bathroom with shower and tubbr• Starter toiletries with shampoo, lotion, cotton swabs and morebrbrEssentials for this fabulous vacation… we’ve got it all for you! For the beach: br• Beach towelsbr• Beach chairsbr• Umbrella br• CoolerbrbrEkolu Village boasts 18 acres of tropical landscaping and breathtaking ocean views. There are two pools on-site for your enjoyment. Charcoal barbecues and picnic area are just a short walk from the condo affording more spectacular ocean views while you dine.brbrCharcoal BBQ picnic areas are scattered throughout the complex to take advantage of the spectacular ocean views that Wailea Ekolu Village affords.brbrIf you're traveling with infants or small children, no need to bring all of your supplies. We work with a great company that will deliver cribs, seats, toys, accessories to our home prior to your arrival and pick them up after you leave (you pay rental company directly).brbrThree fantastic shopping centers, including The Shops at Wailea, with world class dining and shopping are just a short stroll from our condo. The Wailea Beach Walk promenade and its spectacular ocean views is the perfect place for an early morning stroll or to catch a Maui sunset. Just a two minute drive and you can chose from Wailea Beach’s five pristine beaches from Polo Beach to Keawakapu.brbrIf it's golf or tennis that interests you, the Wailea Golf Club is among the world’s greatest golf destinations with its championship Gold, Emerald and Blue courses. Enjoy a discounted rate for Wailea guests. Tennis and pickleball courts at the Wailea Tennis Club are just across the road as well.brbrI KNOW THAT YOU'LL ENJOY OUR HOME AS YOUR HOME-AWAY-FROM-HOME.brOur Maui CondosbrbrPLEASE NOTE THIS IS A NON-SMOKING UNIT.brNO PETS PLEASE.br** We STRONGLY ENCOURAGE all guests to purchase trip insurance for their stay.brbr* Upon Booking confirmation, Host will email Guest an additional copy of our Rental Agreement. Guests will be required to review and sign our Rental Agreement and provide a copy of a government issued ID with address, WITHIN 48 HOURS OF A CONFIRMED RESERVATION. br* Guests will be required to supply the name of all adult guests and ages of any children.br* Maximum number of guests is 4br* Guests with a Vrbo rating, must have a minimum rating of 4 stars to reserve our property.brbr* Please be aware, there is one camera on the outside of the lanai directed toward the ocean view. It does not record.brbrbrKeywords: Condominium, ground floor, ocean view, new king bed, upgrades throughout, perfect locationbrbrHawaii Tax ID# 031-947-7760-01brHawaii State and Maui County taxes are subject to change at any time. If the State or County raises taxes after a reservation has been confirmed, an additional payment request will be submitted for charges relating to the new tax rate.brbr* Rates may vary for occupancy of more then 2 adults
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