Home Vacation Condo Rentals By Owner In Wailea, HI

Showing 40 Of 404 Vacation Rentals
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Exceptional(29)

$352.64

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Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private Lanai

Wailea, Hawaii, United States

Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your visit. Two master suites with king-size beds plus one queen-size sleeper sofa, air conditioning throughout, tastefully renovated bathrooms, and higher-end beach essentials provide every comfort. Prep gourmet meals in the fully stocked kitchen and relax with family and friends in the large living room. Sip coffee and enjoy your meals amidst the tropical flowers on the private lanai that runs the width of the entire unit. brbrOur condo is located in a quiet and private spot directly across the parking lot from one of Grand Champions' two luxurious swimming pools. Favorite restaurants, shops, and beaches are at your doorstep and the condo has everything you need for a relaxing tropical getaway. brbrHere's a taste of what past guests have loved about the updated condo and ideal location:brbr• Quiet location separated from all the activity at the pools and golf coursebr• Short drive (or healthy walk) to some of the best beaches on the planet: Wailea, Maluaka, Keawakapu, Ulua, Big Beach, etc.br• Large private lanai with two sitting areas and tropical jungle viewsbr• Two master suites, each with luxury king beds (+ one queen sleeper sofa) and private en-suite bathsbr• Gourmet kitchen, fully stocked with dishwasher, spices, and other essentialsbr• Air conditioning throughout the condobr• Spacious desk in master bedroom #1 for novel writing, Zooming, or even doodlingbr• High speed wifi, cable TV, and Rokubr• Two nicely landscaped pool and jacuzzi areas in the complexbr• In-unit washer and dryer for your exclusive usebr• Boogie boards, Tommy Bahama chairs, umbrellas, coolers, and plenty of beach towels for use during your staybr• 10-minute walk to The Shops at Waileabr• Master bedroom #2 can be set up with two twin beds (instead of one king) upon request + queen sleeper sofabrbrWe love spending time in this special part of Maui and know you will too! brbr*** brSpecial Note for 2026: Maui Welcomes You with AlohabrbrWailea and the rest of South Maui remain open, thriving, and deeply appreciative of visitors. This area is over 25 miles from Lahaina and was completely unaffected by the August 2024 fires. Local beaches, restaurants, shops, and parks are as beautiful and welcoming as ever.brbrWailea was thoughtfully developed as a master-planned resort community, with many residential properties—including ours—designed specifically to host vacation guests. Visitors have long been an integral part of the area’s identity and economy.brbrTourism is a vital part of life on Maui—it supports local families, small businesses, and the broader recovery effort. The aloha spirit is alive and well, and your visit helps keep it strong. Mahalo for considering a stay in Wailea. We look forward to sharing this special place with you.brbr***brYou'll most likely want a car to explore Wailea and other choice locations on Maui. While you can walk to a number of beaches from the condo, it's uphill coming back and you're in the tropics so heat can be a factor. You'll have one dedicated parking spot directly across from the unit. An additional car can be parked in any available Guest spot. Parking passes can be found on the entry table inside the unit upon arrival. The top half of the parking pass should live on your dashboard throughout your stay. brbrEntry instructions are provided via email a few days before your scheduled arrival on Maui, but we are of course always available to answer any questions in the meantime. We love sharing what we know about Maui with new visitors!
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Bath 2

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Sleep 6

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Exceptional(56)

$1188.28

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HO'OLEI #24-3-BEAUTIFULLY APPOINTED VILLA-SLEEPS 10-METICULOUS CLEANING

Wailea, Hawaii, United States

Book With Confidence This Luxurious 3 Bedroom, 3.5 Bathroom (2619 sq. ft) Villa That Provides Everything That You Need To Have A Great Vacation. The House Offers Tremendous Vacation Experience With It's Amenities, Location, And Level Of Finishes. It Is Managed By PMI Maui, A Local Real Estate Brokerage That Specializes In Vacation Rentals In South Maui. PMI Maui Is Located Within A Few Miles Of The Resort And Available 24/7. 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 House's Features:brbr-Ho'olei Unit #24-3br-Two Story Luxury Townhousebr-3 Bedroom Sleeps 10br-3.5 Bathroomsbr-Luxury King Bed In The Master Bedroom With Bar Fridgebr-Luxury King Bed In The 2nd Bedroombr-2 Full Size Beds In The 3rd Bedroombr-Pullout Sleeper Sofabr-Flat Screen TV In Every Bedroom And Living Roombr-Gaming Systems (Xbox One and Playstation 4) With Large TVbr-Free Highspeed WIFI Internetbr-Brand New Full Sized Washer / Dryerbr-AC Throughoutbr-Fully Equipped Kitchen With Custom Cabinetry And Granite Countersbr-Subzero Fridge And Wolf Gas Cook Top In The Kitchenbr-Large Shaded Lanai With Wolf Gas BBQ Grill And Bar Fridgebr-2nd Lanai On Ground Floor Accessible From The Master Bedroom And 2nd Bedroombr-Gorgeous Resort Oasis Pool Areabr-Great Location Being Right Across The Street From The Grand Waileabr-Pool With Waterfall br-Sand Bottom Kids Wading Poolbr-Covered Poolside Pavilionbr-Hot Tubbr-Fitness Areabr-Free Parking Included For 2 Vehiclesbr-Numerous Beaches In Close Proximitybr-Equipped With Beach Gear Including:br-Tommy Bahama Beach Chairsbr-Beach Umbrella'sbr-Beach Coolersbr-Boogie Boardsbr-Beach ToysbrbrLocated In A Great Area Within Wailea, This House Is Within Walking Distance To World Class Restaurants, Beaches, Shopping, And Golf Courses. Phenomenal Accommodation At A Reasonable Price.brbrHI Tax ID#: TA-210-575-4624-01brbrWe Accept Visa And MasterCardbrbrTo Reserve The House, 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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Sleep 10

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Exceptional(29)

$429.92

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Ocean view-close to beach!Remodeled!Sleeps 5!Bldg 30 Remaining Spring/Summer$250

Wailea, Hawaii, United States

This is a beautiful vacation condominium in the prestigious Wailea resort area regarded as the 'sunny side' of Maui! brbrThe Ekahi complex has just completed the construction of our brand new Pavilion at the beach and it is fabulous!! brbrIt has a lovely ocean view and an beautiful and private lanai to view it from. The condo is bright, airy and well appointed. We also own unit #32C in the building next door! brbrThe entire condo has been recently renovated with all the latest materials and finishings. It features a state-of-the-art split ductless air conditioning system (for those uniquely tropical evenings). The living room features new ceramic tile, a new pullout sectional sofa, end table and a flat panel smart TV with Apple TV and a Sonos playbar for music. The kitchen was completely renovated. The size and usability was enhanced through the creation of an island to replace the previous bar. Granite countertops, cherry wood cabinets and stainless steel appliances create the look of elegance with a tropical flavor. brbrThe bathroom is also completely redone featuring the same materials as used in the living room and kitchen with some accent tiling added. brbrWe are perfectly set up for kids with beach toys, beach chairs, a crib, a highchair and games so you can leave all that at home! brbrWe have an excellent entertainment system for your beach 'downtime' including two flat screen TVs, a Sonos playbar, wireless internet and a telephone with free local and long distance calling to the USA and Canada (you can leave your cell phones along with the outrageous roaming charges at home!). brbrWe know that cleanliness is of upmost concern to you and as such we engage a professional cleaning company on Maui to ensure that the condo is clean and ready for your stay! All of their employees have been trained in how to properly follow all guidelines as provided by the CDC and VRHP (Vacation Rental Housekeeping Professionals). Your booking agreement will detail their specific protocols to give you peace of mind that you are being taken care of. brbrEkahi Village is located on 38 acres of lush surroundings and includes four swimming pools, a beachfront pavilion, paddle courts, shuffleboard and direct access to Keawakapu beach where people of all ages swim, boogie board, snorkel or simply enjoy the magnificent views. Ekahi Village is a short walk from the 'Shops of Wailea', an upscale shopping and dining area and minutes from championship golf, tennis and world famous beaches. brbrPlease consider travel insurance before booking. brNOTE THAT AS OF SEPTEMBER 24, 2021 THE EKAHI COMPLEX NO LONGER PERMITS THE USE OF BBQS AT THE EKAHI CONDOS HOWEVER THERE ARE BBQS AVAILABLE FOR YOUR USE AT THE BEACH PAVILION AND IN A SEPARATE STATION NEAR BUILDING 47. brbrALSO HAVE A LOOK AT OUR OTHER LISTINGS AT EKAHI VILLAGE -Ekahi 39c (two bedroom), Ekahi 22E (one bedroom, two bath), Ekahi 17F (one bedroom, one bath), Ekahi 30c (one bedroom, one bath). brbrOur tax ID # is TA-045-642-7520-01 (TA) and GE-045-642-7520-01 (GE)
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Sleep 5

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Exceptional(32)

$943.48

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Oceanfront Maui condo w/ sunset lanai and pool access

Wailea, Hawaii, United States

Unique opportunity to stay in a one-bedroom, top floor home at one of the most desired properties on Maui. Polo Beach #808 will be your favorite place to stay when visiting the island. Top floor, corner unit with EXQUISITE VIEWS of the Pacific Ocean, Molokini, Kaho'olawe, and looking back at South Maui. Try to find a better spot to enjoy sunset than your own private, West-facing lanai.brbrThis home has been impeccably updated with many modern features, including pull-out shelves and flip-down concealing cabinetry in the kitchen as well as warm mood lighting throughout the condo. The kitchen is fully equipped for those looking to whip up meals at home. Food just tastes better al fresco with ocean views! Plenty of comfortable seating possibilities offered in the living space along with a large wall-mounted Smart TV. Throw on some scenic Hawaii and mute and just listen to the waves of the Pacific Ocean lapping at the shore.brKeep an eye out for Humpback Whales during Winter months as they often breach and play right out front of Polo Beach Club.brbrThe bedroom offers a comfy king bed, ceiling fan, and its own access to the private lanai. Separate Smart TV so you can cozy up in bed and catch up on your fave shows before drifting off to sleep. Grand en suite bathroom has so much space. Huge vanity area with extra spaces for primping and getting ready for the beach or dinner out at one of the nearby fine dining restaurants.brbrAdditional bonus features include central air conditioning throughout the condo, full-size washer and dryer in the unit, and a second full bathroom. Parking and Wifi are complimentary. Beach towels and beach chairs are standard in each home.brbrThe Polo Beach Club is situated in the famous resort community of Wailea, offering world-class dining and shopping options all nearby at the different resorts and The Shops at Wailea. A few favorites include Nick's Fish Market, Ko Restaurant, Spago, Lineage, and Ferraro's. The Polo Beach property features a pool and jacuzzi tub for guest use as well as direct access to Polo Beach. There are also communal BBQ grills on-site and an herb garden to enjoy.brbrStarting December 1st, when you arrive on property, you will be issued a blue parking tag for your unit's 1st vehicle. If you have a second vehicle, it will be given a red parking pass. The RED parking pass does not guarantee your second vehicle a parking spot throughout your stay. If the property has high occupancy numbers during your stay, you will be alerted and will have until 5 pm that day to remove the second car from Polo Beach property and off-site. If the second vehicle is not moved by 5 pm that day, you will be issued a $200.00 fine. If the second vehicle is not removed by 11:59 pm of the same day, there will be an additional $50 per hour fine for every hour the vehicle remains on property after 11:59 pm.brbrWhile we strive to keep all photos up to date, there may be new and updated pieces of furniture or decor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve.brbrPlease note as of April 15, 2026: There is intermittent construction work taking place in a nearby unit. While we do not expect this to impact your entire stay, there may be occasional daytime noise.brHawaii State Tax ID#: 061-828-4544-01
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Sleep 2

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Exceptional(37)

$363.99

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Wailea Ekolu #308 Beautiful Ocean View, Near Golf Course and Beaches, A/C

Wailea, Hawaii, United States

Enjoy spectacular panoramic ocean views from this 2 bedroom condo in a truly private setting! Location is everything and this unit features lovely ocean views from the living area, dining area, kitchen, master bedroom and three lanais and is situated away from all roads and the associated road noise. This two bedroom, two bath Wailea Ekolu condo overlooks the the famous Wailea Old Blue Course. It provides a fully-equipped kitchen s and washer and dryer in the unit. The unit is fully air-conditioned with wall units to keep you cool in bed or as you relax in the living room. If you prefer the outdoors, step right out onto your lanai where you can enjoy an outstanding ocean view. Enjoy sunset cooking with the fully equipped kitchen, stocked with everything you need. For your convenience there is a washer and dryer. There is cable TV in each room, along with complimentary high-speed Wi-Fi. The master bedroom features ocean views, a private lanai, and a brand new king size bed. The guest bedroom has two twin beds that can be converted to a King prior to your arrival upon request. The unit is equipped with to full bathrooms, both with walk-in showers, the master bathroom is en-suite. Enjoy your time at the beach without planning; beach chairs, beach towels, and a beach cooler are all provided for your fun-filled days at the ocean. BBQ grills are not allowed on individual unit lanais in compliance with fire code restrictions. Community grilling stations are available. Whether you are craving the time at the world-class beaches, premier shopping, or taking a few strokes off your golf-game, unit 308 at the Wailea Ekolu will more than satisfy your needs! The unit sleeps 4.brPlease note: This unit is on the second floor with no elevator available. brSame day bookings and those arriving within 24 hours of making the reservation require a phone call to Rentals Maui for confirmation.brBookings made within 7 days of arrival will require an ID check and screening prior to confirmation.brLonger stays require additional terms and conditions. Please contact Rentals Maui for inquiries longer than 60 nights.brWe work to maintain a very accurate website. At times furniture, decor or flooring may be upgraded and pictures are not updated yet. This would not change the seating, sleeping, function or views of the condo. Amenities are accurately and clearly listed for your convenience.
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$496.22

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Wailea Ekolu #1508 Best Location, Panoramic Ocean View, Renovated, Full A/C

Wailea, Hawaii, United States

Experience the comforts of home in a newly renovated, spacious, ocean-view condo. Greet each day from your relaxing private lanai, where each morning’s view and sunset are more stunning than the last.brEnjoy the best panoramic ocean views in Wailea Ekolu – a private and serene luxury resort complex in Wailea. Pictures don’t do it justice! This exceptional property has a timeless and stylish design, quality, and refinement at every corner. Prominently positioned above the renowned Wailea Blue Golf Course, this top level 2 bed, 2 bath unit boasts an almost 180-degree panoramic ocean + golf course views, captivating high-vaulted ceilings, and sophisticated interiors. Abundant natural light pours in through floor-to-ceiling windows, accentuating an open concept living room, upgraded full kitchen, and beautiful hardwood floors.brThe main living area flows seamlessly onto the oversized lanai where you’ll find the perfect view to enjoy a morning cup of coffee. Wine and dine while watching picturesque ocean sunsets amidst the island breeze.brThe master bedroom features its own private ocean-view lanai, Cal King bed, large closet with storage space, brand new ceiling fan and large Smart TV, and an upgraded en-suite master bathroom with walk-in shower. The spacious en-suite second bedroom has a murphy queen bed and doubles as a functional office space (equipped with two built-in workstations). Work remotely in paradise!brLocated in the heart of Wailea, this unit is a 10-minute walk to the beach and world-class resorts. You can take a short stroll to Akamai Coffee Co. or Monkeypod Kitchen for brunch, shop at fine stores at Shops At Wailea, take in the beauty of the Pacific, or take a plunge in one of two property pools. A collection of books, games and beach amenities are also available for your enjoyment. The possibilities are endless! With an unrivaled location, exceptional ocean views and beautiful updated interiors, this ultimate paradise vacation rental has it all. Indulge yourself in the best location in Wailea Ekolu village.brNOTE:br• While BBQ grills are not allowed on individual unit lanais in compliance with fire code restrictions, community grilling stations are available nearby.br• This unit is on the second floor with no elevator available.br• This complex is pet-free.brSame day bookings and those arriving within 24 hours of making the reservation require a phone call to Rentals Maui for confirmation. Bookings 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.
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Exceptional(43)

$413.62

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Budget Luxury, Grand Champion Golf Villa #129 - 2 Bd/2 Bath-NEW upgrades!

Wailea, Hawaii, United States

New, new, new. Upgrades galore. Fresh paint, new tile, new furniture, flooring, electronics, beds, and more!brProfessional photos pending! Comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. A fully stocked kitchen for home-cooked meals and a private lanai for outdoor dining welcome you to one of Wailea's favorite properties. Easy access on the first floor and convenient guest parking near the front of the condominium make this a property you will enjoy as your home-away-from-home. brWailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South Maui, nestled between the championship Ol’ Blue Golf Course and the award winning Wailea Tennis Center. Lush tropical gardens and swaying palm trees surround all 188 units, two swimming pools, two Jacuzzis and four gas BBQ grills to enjoy. Shopping, dining, activities, and amenities are conveniently located within walking distance. Beautiful Wailea beaches are just a short drive away or a 15–20-minute walk from the Villas. Wailea Grand Champions Golf Villas offers great values and views in the heart of the upscale Wailea Resort community. brbrThis luxury-on-a-budget property is in the center of Wailea’s Ol’ Blue Golf Course, with contemporary villas featuring private lanais for sunset views over the fairways to the West Maui mountains. Wailea area resorts, spa facilities, and award-winning restaurants are within walking distance, and Wailea’s fabulous beaches are a leisurely 15-minute walk or easy 3-minute drive from the Wailea Grand Champions Villas. Wailea Gateway Center, Wailea Town Center, The Shops at Wailea, and the newest shopping/entertainment destination Wailea Village Center are all a few minutes’ walk from your vacation home at Wailea Grand Champions.brbrBeach chairs, beach towels, beach umbrella, and a cooler are provided. Additional beach gear may be rented at one of our local beach shops.brbr**Please note**brAll Holiday reservations are due, paid-in-full on October 1st. Holiday season is 12/15 to 1/10brNo refunds on Holiday cancellations after October 1st.br*Note: No assigned parking stall for this condominium. Guests must park cars in GUEST parking stalls only. There are a lot of guest parking spaces. brbrDiscounts for 14-day and 30-day stays are already included in total price shown.
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Exceptional(8)

$305.15

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Lush Wailea Ground Floor Condo Tropical Oasis Four Pools Keawakapu Beach

Wailea, Hawaii, United States

Enjoy your open and airy living area with breathtaking views of the picturesque foliage through your lanai door in unit 52A! Ample seating available as the dining table for four and two seats at the bar area provide comfort and relaxation as you entertain family and friends. Imagine preparing your favorite dishes in this spacious and fully equipped kitchen with upgraded stainless steel appliances and marble counter tops. brbrYou can absolutely look forward to air conditioning and TVs in both living room and bedroom so you may catch up on your favorite shows while cooling off from an exciting day on island! Snuggle down in your king bed for an amazing night’s rest and wake to the cheerful sounds of our native Hawaiian birds singing to you from your own private bedroom lanai. Soak in luxury in your en-suite jacuzzi bathtub before or after a wonderful day in perfect paradise! brbrThe sofa sleeper in the living room includes a new memory foam mattress for your guest’s ultimate comfort and joy. brbrROOM AMENITIES: Smoke Free environment, Air conditioning throughout the property, Free WiFi, Fully Equipped Kitchen (Cooking range/oven, Refrigerator, Dishwasher, Microwave, Blender, Coffee maker, Dishes & silverware) Cable television in living room + bedroom, Ceiling fan, Private lanai, Iron and ironing board, Additional linens and towels, Complimentary starter kit of laundry detergent, shampoo, soap etc. Hair dryer, Beach gear (beach chairs, beach towels, a cooler and a beach umbrella), Free parking.brbr*This property is not handicap accessiblebrbr*Please keep in mind that from time to time you may hear some car noise from the street behind the unit. However if you are enjoying the oceanfront pools or if you are at the beach throughout the day this may not be any concern for you*brbrTax Map Key 210080650091 TA: 140-569-1904-01
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Sleep 4

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Exceptional(18)

$402.39

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Steps to Wailea Beach, A/C, Groundfloor

Wailea, Hawaii, United States

NOTICE: POOL CLOSURES September 15-18, 2026.brbrThis beautiful, tropical two-bedroom/two-bath condo is just a short 5-minute walk from the world-famous Keawakapu Beach!! Enjoy dreamy sunset strolls along the golden sands or start your day with a peaceful jog through paths lined with lush tropical flowers. Dive into the crystal-clear waters for snorkeling, kayaking, or whale watching—it’s all just moments from your door! Nestled in the serene and exclusive Palms at Wailea, this hidden gem is close to Wailea’s top dining, shopping, and three championship golf courses!brbrEnjoy the relaxed Maui lifestyle in comfort and style! The garden-level lanai offers comfortable seating and is surrounded by a lush lawn and fragrant tropical scenery—perfect for evening dinners or morning coffee. The fully furnished kitchen includes everything you need to cook delicious meals at home, featuring modern appliances and all the amenities you need for a carefree stay.brbrThe spacious living room offers a comfortable sofa and flat screen smart TV—perfect for movie nights after a long day of island adventures. The 3-zone split air conditioning system ensures cool comfort in the living room and both bedrooms.brbrThe master suite features a luxurious king bed with hotel-quality bedding and its own private AC unit and smart TV. The second bedroom includes two twin beds, offering privacy and flexibility for your group. Two full bathrooms make it easy for everyone to get ready in comfort.brbrThe condo is equipped with beach towels, chairs, and coolers for your beach or day trips. There’s also in-suite laundry and plenty of bath towels to keep things easy and relaxed—just the way a Maui vacation should be!brbrIndoor Featuresbr2 Bedrooms - King Bed + Two twin beds brSplit Air Conditioning (living room + both bedrooms)brFlat screen Smart TVsbrFully stocked kitchenbrWasher + DryerbrbrOutdoor FeaturesbrGarden-level lanai brPoolbrHot TubbrBarbecue Grills brLush tropical landscapingbrbrHawaii Life Rentals is a locally owned, licensed real estate company with rentals on Kauai, Maui, Oahu, and Hawaii. We offer on-island personal assistance and Concierge services.brbrRates do not include taxes, cleaning and applicable fees.brbrHawaii Life/VRBO bookings: Guests must sign a rental contract within 48 hours of booking to confirm the reservation.brbrTA-085-604-9152-01
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Exceptional(15)

$301.4

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Wailea Ekahi 52B | Resort Level Amenities!

Wailea, Hawaii, United States

With 34 acres of landscaped resort bordering one of Hawaii’s best beaches, Wailea Ekahi 52B is the ideal place to experience the very best of Hawaii. It’s affordable luxury that’s perfect for two couples wanting to share an island getaway. There’s a minimum stay requirement of five nights, but with all there is to see and do in Maui, Hawaii, you’ll need every bit of that time to explore.brbrThe studio apartment is garden level with a private covered lanai surrounded by lush vegetation. There you’ll find your dining table and a gas grill in case you want to grill some Mahi Mahi, burgers, or kebobs.brbrThe light, bright studio itself breaks all the stereotypes of studio living. You have a large couch that pulls out into a queen-size sofa sleeper for your guests and at the other end of the spacious room there’s a plush queen-sized bed. There’s plenty of room to move around and enjoy the apartment.brbrWailea Ekahi 52B has a large TV with cable and both a DVD player and VCR. However, it’s hard to imagine you’ll be watching much TV with all there is to do and see on Maui. The studio also has free Wi-Fi, which is a great way to check out restaurant menus and websites for area attractions. Of course, you’ll want to send photos of yourself playing in the surf home to friends.brbrThe owners of Wailea Ekahi 52B provide beach towels, beach chairs, and a beach umbrella to use during your stay. Take your gear and head down to the soothing waters of the Pacific Ocean as only Hawaii delivers them.brbrOf course, you could dine out every night while you’re staying at Wailea Ekahi 52B. There are that many dining options including many within the Shops of Wailea that is only a short drive away. If you’d rather cook something at the studio, that’s definitely possible. Wailea Ekahi 52B has a fully equipped galley-style kitchen with everything you need to prepare food for you and your guests. Just stop by the local grocery store and you’ll soon be whipping up delicious meals. There’s even a breakfast bar where you can enjoy your morning coffee.brbrThe Wailea Ekahi 52B bathroom includes a shower/tub combination and there’s even a stacked washer and dryer tucked away within the condo so you can pack light and still have plenty of clean clothes each day.brbrThere are four beautiful swimming pools to enjoy within the Wailea Ekahi complex. There’s also shuffleboard and tennis within the resort, and beautiful golf courses just a short drive from the condo.brbrYou’ll have a five-star vacation in one of the world’s most beautiful locations when you book your stay at Wailea Ekahi 52B. Get away from the ordinary and enjoy the silky sands of Keawakapu Beach. There’s a beach chair waiting for you! Book your stay today!brbrPlease Note: Exterior painting will be taking place in this building during November 9, 2026- November 23, 2026.
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Sleep 4

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$496.09

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Palms at Wailea Ocean View Villas 1 Bedroom 2 Bath

Wailea, Hawaii, United States

Enjoy stunning ocean views from villas featuring a full kitchen, spacious living area, and a private patio; it’s the perfect spot to relax while soaking in Maui’s breathtaking coastal beauty. brbrOcean View Villa 1 Bedroom 2 Bathbrbr• Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, cookware and tableware brbr• Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent brbr• Bedroom has 1 king bed or 1 queen bed brbr• Master bathroom with free-standing shower or shower/tub combination brbr• Second bathroom with free-standing shower or shower/tub combination brbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryer brbr• Dining room table with seating for 4 brbr• Living area with sofa bed brbr• Ceiling fan in living room brbr• Air conditioning in master bedroom only; some units have AC in entire unit & is available on request at $15 per night brbr• Shutters brbr• Washer/dryer in unit brbr• Balcony or patio with furniture brbr• TV with standard cable brbr• Wi-Fi brbr• In-room safe brbr• Iron and board brbr• Smoke detectors brbr• Children 17 years and under are free when sharing room with parent(s) utilizing existing beds brbrThis listing features a wonderful collection of condos that we manage in this category. The Photos you see capture the unique character of these properties, giving you a taste of what each has to offer. We can't wait for you to find your perfect getaway!
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Sleep 4

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$593.12

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Palms at Wailea Ocean View Villas 2 Bedroom 2 Bath

Wailea, Hawaii, United States

Take in breathtaking ocean views from a spacious two-bedroom villa in Wailea’s resort community. Featuring a full kitchen, open living area, and private patio, it’s the perfect retreat for families or friends seeking a relaxing Maui escape. brbrOcean View Villa 2 Bedroom 2 Bathbrbr• Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, cookware and tableware brbr• Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent brbr• Master bedroom has 1 king bed or 1 queen bed brbr• Second bedroom has 1 queen bed or 2 twin beds brbr• Master bathroom with free-standing shower or shower/tub combination brbr• Second bathroom with free-standing shower or shower/tub combination brbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryer brbr• Dining area brbr• Living area with sofa bed brbr• Ceiling fan in living room brbr• Air conditioning in master bedroom only; some units have AC in entire unit & is available on request at $20 per night brbr• Shutters brbr• Washer/dryer in unit brbr• Balcony or patio with furniture brbr• TV with standard cable brbr• Wi-Fi brbr• In-room safe brbr• Iron and board brbr• Smoke detectors brbr• Children 17 years and under are free when sharing room with parent(s) utilizing existing beds brbrThis listing features a wonderful collection of condos that we manage in this category. The Photos you see capture the unique character of these properties, giving you a taste of what each has to offer. We can't wait for you to find your perfect getaway!
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Exceptional(63)

$343.66

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Stunning Views, Walk to Beach! Spacious Ekahi 49F

Wailea, Hawaii, United States

This listing has views from your lanai will have you coming back year after year--and the beach is a short stroll across the condo property! A cozy one bedroom and one bath second floor, this unit supplies you with everything you need for a memorable vacation. Choose from indoor or outdoor dining with the convenience of cooking your own meals. Wailea Ekahi no longer allows private grills but they offer a beautiful gas grilling area at the community Pavilion. The kitchen has the appliances and utensils you need to create great dishes. The comfortable living room allows you to relax in style. If catching up on sleep is a priority, the king bed will offer you that opportunity! Within the Ekahi complex, you will find 4 pools, paddle tennis and shuffleboard for your enjoyment. Come enjoy a relaxing stay in 49F!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.Guest accessWithin the Ekahi complex, you will find 4 pools, paddle tennis and shuffleboard for your enjoyment. Come enjoy a relaxing stay in 49F!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.brbrOther things to notePlease note: Upon confirming your reservation, we will request your personal email address. A company specific rental agreement will be emailed to the provided address. Once we have received your completed rental agreement, detailed arrival instructions will be emailed to you one week prior to your stay.br*Window A/C in Bedroom Only*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.brRegistration number 210080650078, TA-213-968-7936-01
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$948.6

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Sunset Views | Whale Watching | Resort Amenities

Wailea, Hawaii, United States

Welcome to your serene paradise at Wailea Elua Village 307, a stunning 2-bedroom, 2-bathroom ocean view condo nestled in the heart of Wailea. This thoughtfully designed retreat offers a perfect blend of comfort and luxury, ideal for your next Hawaiian getaway.brbrThe open floor plan is designed to promote socializing and engagement as guests transition between cooking, dining, and relaxing. A large sectional sofa is flanked by two armchairs and abundant natural light through the floor-to-ceiling glass doors that span a majority of the nearest wall. Open the sliding doors out to your ocean view wrap-around lanai to create the tropical indoor/outdoor lifestyle you are looking for. Take tropical drinks made at your wet bar out for sunset views. brbrAn enclosed office off the living room, complete with full desk, creates the perfect private nook to take a virtual call or work remotely if needed. Complete office tasks while the rest of your travel party unwinds in the spacious 1,336 square foot floorplan. brbrThe fully equipped kitchen features stainless steel appliances and includes all your favorite cooking gadgets. Prepare banana macadamia nut cookies for breakfast one morning or prepare fruit smoothies from your findings at the local farmer’s markets. brbrThe primary bedroom has a king bed, while the second bedroom has two twin beds. Both bedrooms have televisions for private viewing before nodding off each night. Take advantage of the stacked washer/dryer, allowing you to potentially have more room in your suitcase for souvenirs and gifts to take back home!brbrThis 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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$482.94

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Palms at Wailea Garden Villas 1 Bedroom 2 Bath

Wailea, Hawaii, United States

A peaceful one-bedroom villa with lush garden views, located in Maui’s renowned Wailea Resort community. Perfect for a relaxing getaway, it features a full kitchen, open living space, and private lanai – just minutes from pristine beaches and championship golf.brbrGarden Villa 1 Bedroom 2 Bathbrbr• Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, cookware, and tablewarebrbr• Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergentbrbr• Bedroom has 1 king bed or 1 queen bedbrbr• Master bathroom with free-standing shower or shower/tub combinationbrbr• Second bathroom with free-standing shower or shower/tub combinationbrbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryerbrbr• Dining room table with seating for 4brbr• Living area with sofa bedbrbr• Ceiling fan in living roombrbr • Air conditioning in master bedroom only; some units have AC in entire unit & is available on request at $15 per night brbr• Shuttersbrbr• Washer/dryer in unitbrbr• Balcony or patio with furniturebrbr• TV with standard cablebrbr• Wi-Fibrbr• In-room safebrbr• Iron and boardbrbr• Smoke detectorsbrbr• Children 17 years and under are free when sharing room with parent(s) utilizing existing bedsbrbrThis listing features a wonderful collection of condos that we manage in this category. The Photos you see capture the unique character of these properties, giving you a taste of what each has to offer. We can't wait for you to find your perfect getaway!
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$534.56

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Palms at Wailea Garden Villas 2 Bedroom 2 Bath

Wailea, Hawaii, United States

Relax in a spacious two-bedroom villa with peaceful garden views, located in the prestigious Wailea resort community. Featuring a full kitchen, open living area, and private patio, it’s perfect for families or small groups seeking a serene Maui getaway. brbrGarden View 2 Bedroom 2 Bath Villabrbr• Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, cookware and tableware brbr• Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent brbr• Master bedroom has 1 king bed or 1 queen bed brbr• Second bedroom has 1 queen bed or 2 twin beds brbr• Master bathroom with free-standing shower or shower/tub combination brbr• Second bathroom with free-standing shower or shower/tub combination brbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryer brbr• Dining area brbr• Living area with sofa bed brbr• Ceiling fan in living room brbr• Air conditioning in master bedroom only; some units have AC in entire unit & is available on request at $20 per night brbr• Shutters brbr• Washer/dryer in unit brbr• Balcony or patio with furniture brbr• TV with standard cable brbr• Wi-Fi brbr• In-room safe brbr• Iron and board brbr• Smoke detectors brbr• Children 17 years and under are free when sharing room with parent(s) utilizing existing beds brbrThis listing features a wonderful collection of condos that we manage in this category. The Photos you see capture the unique character of these properties, giving you a taste of what each has to offer. We can't wait for you to find your perfect getaway!
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Exceptional(76)

$990.32

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Oceanfront Wailea condo w/ pool, lanai and snorkeling

Wailea, Hawaii, United States

Experience true paradise and stunning ocean views from the lanai as you sip on your morning coffee! Stroll along the world famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach or unwind and sunbathe at the ocean front pool and jacuzzi.brbrThis immaculate 2 Bedroom, 2 Bathroom accommodation is a slice of heaven. This unit features beautiful and tasteful furnishings, a fully equipped gourmet kitchen with an open floor plan, stainless steel appliances, tile floors throughout, and a fabulous lanai to watch the sunset and take in the beauty of Maui.brbrThis unit accommodates up to six guests and features a king-sized bed in the Primary Bedroom, two twin beds in the Guest Bedroom which can also be made into a King, and a very comfortable sleeper sofa bed in the living area. The Primary Bedroom features an ensuite bathroom, and there is also a second full guest bathroom. There is central air conditioning and wireless internet access throughout.brbrThe Polo Beach Club is situated in the resort community of Wailea, offering world-class dining and shopping options all nearby at the different resorts and The Shops at Wailea. The Polo Beach property features a pool and jacuzzi tub for guest use. There are also communal BBQ grills on-site and an herb garden to enjoy.brbrUpon arrival, you’ll find a white and blue parking pass in the unit for your vehicle. If you have a second vehicle, please stop by the AOAO office on-site for further instructions on where to park, as availability may vary depending on occupancy levels. Failure to park in designated areas may result in fines and towing.brbrWhile we strive to keep all photos up to date, there may be new and updated pieces of furniture or decor that are different than in the original pictures. The functionality, available seating, and sleeping space will remain the same or may improve.brbrBeginning April 15, 2026, a neighboring residence will be undergoing a remodel. In addition, the property will be completing an exterior power washing and painting. Noise levels are difficult to predict, however, there may be intermittent daytime disturbancebrHawaii State Tax ID#: 145-738-1376-01
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$282.15

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

Wailea, Hawaii, United States

Views! Views! Views! Experience breathtaking ocean and fairway vistas from this top-floor unit. This spacious condo features a generously sized living room, a cozy primary bedroom, and two full baths. Whether you're marveling at sunsets over the expansive 2nd fairway or catching a glimpse of a passing deer on the lawn during the early morning hours, you're in for a treat.brbrThis unit offers a high level of comfort. Unwind on your private lanai, where you can enjoy the refreshing trade winds sweeping across the greens and savor the delightful aroma of the beautiful Plumeria trees and Hawaiian foliage. This exceptionally roomy one-bedroom unit in the Grand Champions Villas is fully equipped with all the amenities to make you feel right at home. Fresh paint and new carpet were added in 2022 to enhance your stay.brbrPrime Location! The Grand Champions showcases lush, captivating landscaping and offers various amenities, including two pools, a Jacuzzi, BBQ facilities, and security. Its central Wailea location is a major plus, enabling you to walk to tennis courts, the Shops at Wailea, a variety of casual to fine dining restaurants, the world's top beaches, and five-star hotels.brbrNo matter what your vacation aspirations may be, this condo promises that you'll have an amazing time with your expectations met and memories created to last a lifetime.brbrWhile we do our best to ensure all photos are kept up to date, you may come across new and updated pieces of furniture or decor that differ from the original pictures. However, the functionality, available seating, and sleeping arrangements will remain the same or may have even improved.brUpdate 5/22: Dryer Vent Cleaning taking place between 8/3-8/13. br*Window A/C in every room*brHawaii Tax ID #: 037-546-8032-01
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Exceptional(62)

$422.37

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Stunning Ocean Views! Renovated Wailea Ekolu 502

Wailea, Hawaii, United States

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

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Palms at Wailea Garden Deluxe Villas 2 BD 2 BA

Wailea, Hawaii, United States

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

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Bath 2

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Sleep 6

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