Vacation Rentals By Owner In Wailea, HI

$554.76

Palms at Wailea Villa 805 Garden View 2 BD 2 BA

Wailea, Hawaii, United States

Enjoy a peaceful stay in this two-bedroom garden-view villa nestled within the Wailea resort community’s lush surroundings. With a full kitchen, roomy living area, and private patio, it offers a perfect blend of comfort and natural beauty. brbrVilla 805 Garden 2 Bedroom 2 Bathbrbr• Located in building 8 on the ground level with a reserved parking stall in front brbr• Kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, dishwasher, cookware and tableware brbr• Welcome essentials kit includes coffee, sugar, creamer, dish soap, sponge, paper towels, laundry detergent & dishwasher detergent brbr• Master bedroom has 1 king bed brbr• Second bedroom has 1 queen bed brbr• Master bathroom with free-standing shower brbr• Second bathroom with shower/tub combination brbr• Bath amenities include shampoo/conditioner, soap, lotion, tissues & hair dryer brbr• Dining area brbr• Living area with sofa bed brbr• Air conditioning in entire unit brbr• Ceiling fan in living room and bedroom brbr• Shutters brbr• Washer/dryer in unit brbr• Patio with furniture brbr• TV with standard cable brbr• Wi-Fi brbr• In-room safe brbr• Iron and board brbr• Smoke detectors brbr• Children 17 years and under are free when sharing room with parent(s) utilizing existing beds

Bed

Bath

Sleeps

$642.25

/ Nightly

Condo

Grand Champions 144 | Tropical Golf Resort w/ Pool

Wailea, Hawaii, United States

Welcome to Grand Champions 144, a spacious three-bedroom, two-bathroom condo that sleeps six guests in beautiful Wailea, Hawaii. This stunning vacation rental condo in Wailea, Hawaii, is nestled within a premier resort community!brbrStep onto the large private balcony of Grand Champions 144 to take in breathtaking, peaceful views of the emerald fairways. This expansive outdoor space is the perfect spot to enjoy your morning coffee or a cool evening beverage while listening to the sounds of nature. The primary suite offers the unique luxury of a private lanai, allowing you to wake up and immediately breathe in the warm Maui air. Within the complex, you can enjoy elevated amenities including two sparkling community pools, jacuzzi spas, and poolside barbeque grills for a sunset cookout.brbrInside, Grand Champions 144 features an open-concept layout highlighted by windows that flood the main living space with sunshine. The high-end kitchen is equipped with stainless steel appliances and ample counter space, making it easy to prepare island-inspired meals. The primary bedroom serves as a personal retreat with a king-size bed and a spa-like en suite bathroom featuring a walk-in shower and dual vanities. With two twin beds in the second room and a queen in the third, there is plenty of space for the whole family to relax in coastal style.brbrAdventure awaits just outside your door, as Grand Champions 144 is within walking distance of sandy beaches and the upscale Shops at Wailea. Spend your days playing a round at the Old Blue Golf Course, practicing your serve on the tennis courts, or snorkeling among vibrant sea life.brbrBook your stay at Grand Champions 144 today.

Bed

Bath

Sleeps

$377.47

/ Nightly

Condo

Luxury on a Budget Wailea Ekolu 1403 -1 Bed/2 Bath Vacation Condo

Wailea, Hawaii, United States

Fresh new upgrades - new king bed, new wood flooring, new TVs, kitchen appliances, window blinds, lighting, and two comfortable lanais with an outdoor lawn area. New refrigerator, stove, dining room table, barstools, window shades, new linens and towels. We also have new housekeepers, and the unit is sparkling with all the upgrades! This roomy and comfortable condominium home in the resort destination of Wailea Ekolu Village is fully stocked and upgraded to be a special vacation home for couples and small families to enjoy all that South Maui has to offer. brbrWailea Ekolu Village features premier one- and two-bedroom ocean view and garden view condos. The resort sits on 18 acres of tropical landscaping and is located adjacent to the Wailea Ol' Blue' Golf Course. Each vacation condominium has a fully equipped kitchen with washer/dryer. The property features two swimming pools, barbecues and a reading/gathering pavilion. Mokapu Beach, Ulua Beach and Keawakapu Beach, three of Maui's favorites, are nearby.brbrBeach chairs, umbrella, beach towels and coolers are provided. Additional beach gear may be rented at one of our local beach shops.brbrWailea Ekolu Village is just mauka (uphill) from the Shops at Wailea and the Wailea Village Center shopping and entertainment centers. Special rates are available at Wailea's golf and tennis facilities for Ekolu guests. Wailea Gateway Shops, Wailea Town Center, The Shops at Wailea, and all of Wailea's famous hotels, spa facilities and award-winning restaurants are within walking distance. Wailea Ekolu Village is a premier vacation location. brbr** Please note **brAll Holiday Season reservations are due, paid-in-full on October 1st. Holiday season is 12/15 to 1/10brNo refunds on Holiday Season cancellations after October 1st.

Bed

Bath

Sleeps

$428.21

/ Nightly

Condo

Wailea Ekahi 40A - 5-Star South Maui Oasis

Wailea, Hawaii, United States

*Please note-The main pool will be closed for refurbishment from August 10, 2026-October 15, 2026. Three other smaller pools will be available for use, but the main pool will be closed during this time*brbrWelcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even sidewalk!brbrOur private corner unit is in immaculate condition, tastefully appointed, and looks out upon a lush, well-maintained rolling green lawn. It is surrounded by fragrant plantings and hedges which add to our unit's privacy. 40A is removed from the street, looks out onto an open space, and is undoubtedly one of the most quiet units in Ekahi. brbrIsland-style comfort awaits inside with cooling fans in every room, tasteful decorations, a king bed in the master, sheltered back lanai for relaxing, and a beautiful, spacious kitchen. We have installed brand-new appliances and high-end fixtures throughout.brbrTo smooth check-in and ensure you relax after a long flight, we have keyless access to both front and back doors and ensure the unit is squeaky clean before your arrival. brbrShould you desire to leave 40A, stroll around the corner and down the Ekahi greenbelt. Walking past beautiful plantings and fruit trees, in five minutes you will come to the oceanfront family pool. Walk through the pool and out the private exit to Keawakapu Beach (one of the best on Maui) without crossing any roads. The sheltered water is perfect for littles but also provides great boogie and body surfing when the breeze comes up in the afternoon. Build sand castles, run/walk the mile of beach, or snorkel around the lava outcroppings.brbrIf you ever get enough beach and sunshine, retire to the pool and brand-new shaded pavilion, featuring a full kitchen and BBQ area in addition to restrooms and showers. The pavilion also provides an amazing perch over Keawakapu beach to watch the sunset and whales frolicking offshore between November and March.brbrEnd your day with a walk back up the greenspace to your unit, which we keep scrupulously cleaned and maintained. We spend a few weeks a year here and stay on top of all maintenance items; if something breaks or goes missing between visits, we will schedule it to be fixed as soon as you notify us.brbr40A is stocked with everything you need for a comfy stay including boogie boards, beach towels and chairs, linens, utensils and cooking equipment, TVs, and WiFi. 40A accommodates up to 4 guests with a queen sleeper sofa and twin Murphy bed in the living room.brbrTo our great sadness (Chad is an addicted griller), Ekahi now complies with Maui fire codes and all personal BBQs have been removed. Luckily, the closest group BBQs are a one minute jaunt off the back lanai (to the right). There are also a few other group gas BBQ areas throughout the property.brbrShould your interests fall elsewhere, Ekahi also offers Pickle Ball, shuffleboard, paddle tennis, a family pool, and three quiet lounging pools (one just steps away). The high-end shops, hotels, and restaurants of Wailea are within walking distance along the beach or main road, and the funky shops, eateries, and grocery stores of Kihei are less than a 10 minute drive away.

Bed

Bath

Sleeps

$543.65

/ Nightly

Condo

Beachfront Wailea condo w/ ocean views and hot tub

Wailea, Hawaii, United States

If you are looking for a perfect getaway in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi and all the amenities this popular complex affords.brbrThis spacious fully air-conditioned two-bedroom two-bath unit is immaculate and beautiful and comes equipped with all the amenities so that you feel as if you are right at home. Enjoy the pleasant ocean views from the large wraparound lanai in a tropical garden setting. This unit has approximately 1200 square feet of living area plus a wraparound lanai. Top floor, tastefully furnished, split air conditioning, plush carpeting, gourmet kitchen, spacious living area, and lots of more.brbrLocated above the pristine shores of Keawakapu Beach, this impeccably furnished home will provide comfort, luxury, and plenty of room to spread out while you explore and enjoy all that Maui has to offer. The spacious covered lanai with a dining table allows for relaxing evenings while you kick back and enjoy the views. Relax poolside or take a Jacuzzi after the sun sets and take in the beauty of the brilliant Maui skies.brbrThe Wailea Golf Course and Tennis Clubs are just a minute away. Within walking distance are some of the World's Top Beaches as rated by Conde Nast International. If shopping is your pleasure, the elegant Shops of Wailea are situated a stone's throw away. For the adventurous type, you will find amazing snorkeling spots within a very short drive.brbrPlease note that Palms at Wailea no longer allows private grills. There will not be a grill for you to use on the lanai of this condo.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.brbrWe would like to inform you that the pool at the Palms of Wailea will be temporarily closed from September 16th to 19th for cleaning and resealing of the pool surface to ensure a safe environment for everyone. To further prevent future closures, we have also scheduled a drainage of the pool during this time to repair pool equipmentbrNotice 2/18/26 - Pool Closure: Tuesday, Sept,. 15th -Friday, Sept,.18th 2026brThe Pool Area Will Reopen Saturday September 19th with Regular HoursbrHawaii Tax ID #: 152-503-2960-01

Bed

Bath

Sleeps

$547.5

/ Nightly

Condo

Keawakapu Beach condo w/ hot tub and lanai

Wailea, Hawaii, United States

The name PALMS AT WAILEA aptly describes the feel of this beautiful complex. Located above the pristine shores of Keawakapu Beach, this impeccably furnished home will provide comfort, luxury, and plenty of room to spread out while you explore and enjoy all that Maui has to offer.brbrThe spacious covered lanai with a dining table allows for relaxing evenings while you kick back and enjoy the views. Relax poolside or take a Jacuzzi after the sun sets and take in the beauty of the brilliant Maui skies.brbrThis fully air-conditioned deluxe unit (approx 1200 square feet) is immaculate and beautiful and comes fully equipped with all the amenities so that you feel as if you are right at home. The kitchen is perfectly appointed with newer appliances and all cooking and serving items you will need to whip up meals at home.brbrThe primary bedroom features a king-sized bed and has its own AC and TV and also access to the lanai. The en suite bathroom has a tub-shower combo and a huge vanity that makes getting beach ready a snap.brbrThe guest room has 2 twin beds that can be pushed together upon request using a conversion kit to make a comfortable king bed. The second full bathroom is just off the guest bedroom and located conveniently for all to use. This one has a tiled walk-in shower.brbrWithin walking distance are some of the World's Top Beaches as rated by Conde Nast International. If shopping is your pleasure, the elegant Shops of Wailea are situated a stone's throw away. For the adventurous type, you will find amazing snorkeling spots within a very short drive.brbrPlease note that Palms at Wailea no longer allows private grills. There will not be a grill for you to use on the lanai of this condo.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.brbrWe would like to inform you that the pool at the Palms of Wailea will be temporarily closed from September 16th to 19th for cleaning and resealing of the pool surface to ensure a safe environment for everyone. To further prevent future closures, we have also scheduled a drainage of the pool during this time to repair pool equipmentbrNotice 2/18/26 - Pool Closure: Tuesday, Sept,. 15th -Friday, Sept,.18th 2026brThe Pool Area Will Reopen Saturday September 19th with Regular HoursbrHawaii Tax ID #: 152-503-2960-01

Bed

Bath

Sleeps

$543.65

/ Nightly

Condo

Beachfront Wailea condo w/ pool and hot tub access

Wailea, Hawaii, United States

Fabulous condo! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this popular complex affords.brbrThis central air-conditioned 2-bedroom, 2-bath unit is immaculate and beautiful and comes equipped with all the amenities so that you feel as if you are right at home. Enjoy the pleasant views from the large wraparound lanai in a tropical garden setting.brbrThis unit has approximately 1200 square feet of living area plus a lanai! Fully air-conditioned. This is the largest 2-bedroom unit in the complex! The primary bedroom features a King-sized bed and the guest room has 2 twin beds that can be converted to a King upon request. Top floor, tastefully furnished, plush carpeting, gourmet kitchen, spacious living area, and lots more.brbrLocated above the pristine shores of Keawakapu Beach, this impeccably furnished home will provide comfort, luxury, and plenty of room to spread out while you explore and enjoy all that Maui has to offer. The spacious covered lanai with a dining table allows for relaxing evenings while you kick back and enjoy the views. Relax poolside or take a Jacuzzi after the sun sets and take in the beauty of the brilliant Maui skies.brbrThe Wailea Golf Course and Tennis Clubs are just minutes away. Within walking distance are some of the World's Top Beaches as rated by Conde Nast International. If shopping is your pleasure, the elegant Shops of Wailea are situated a stone's throw away. For the adventurous type, you will find amazing snorkeling spots within a very short drive.brbrPlease note that Palms at Wailea no longer allows private grills. There will not be a grill for you to use on the lanai of this condo.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.brbrbrNotice 2/18/26 - Pool Closure: Tuesday, Sept,. 15th -Friday, Sept,.18th 2026brThe Pool Area Will Reopen Saturday September 19th with Regular HoursbrHawaii Tax ID #: 152-503-2960-01

Bed

Bath

Sleeps

$565.93

/ Nightly

Condo

Summer Deal Wailea 3BR Condo with Ocean and Golf Course Views

Wailea, Hawaii, United States

Experience gorgeous ocean and fairway views from this spacious top floor, tastefully decorated, family-friendly, three-bedroom unit. This beautiful condo boasts the largest floor plan available at Grand Champion Villas. Enjoy the views of the islands of Lanai and West Maui from the huge wrap-around lanai, which provides extra room for relaxing and taking in the splendor of the sun setting over the Pacific.brbrThis unit has a spacious, newly remodeled kitchen graced with stainless steel appliances, beautiful countertops, contemporary cabinets, and fully appointed to comfortably meet all your dining desires! The living/dining area features vaulted ceilings, is bright and airy, and easily accommodates eight people. Enjoy amenities such as AC, TV with video and DVD player, and a CD player. The huge Primary bedroom has a private lanai with a beautiful view of Haleakala and features a king pillow-top bed, flat-screen TV/DVD player, CD player, AC, walk-in closet, and a large private his/her bathroom. The second bedroom has cozy pillow-top twin beds with pleasant mountain breezes and a view of Haleakala. The third bedroom has a queen pillow-top bed, TV/video player, AC, and a view featuring lush foliage, sunsets, and a glimpse of the Pacific.brbrThere is plenty of room for everyone in this great vacation condo! Guests love this unit because of all the amenities and extras, from fun games to books, music, movies, and beach towels - all to make you feel as if you are in your own home.brbrThe Grand Champions Villas features lush tropical landscapes with two pools, Jacuzzis, and BBQ facilities. This wonderfully appointed villa is situated on the 7th Fairway of Wailea's elite Blue Golf Course, allowing you to take advantage of special golf and tennis rates offered to Wailea guests. The location is fantastic! Within walking distance are The Shops at Wailea, fabulous restaurants (casual to fine dining), Five Star Hotels, and Top Rated World-Class Beaches.brbrGaze at sunsets across the expanse of the 7th fairway and see an occasional deer scampering across the lawn in the early hours of the morning. Relax on your own private lanai and feel the wonderful trade winds sweep across the greens and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. If you are looking for a perfect getaway in paradise, this is it!brbrbrbrWhile 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.br*Window A/C in Living Room and Primary Bedroom Only*brUpdate 5/22: Dryer Vent Cleaning taking place between 8/3-8/13. brHawaii Tax ID #: 101-170-7904-01

Bed

Bath

Sleeps

$354.44

/ Nightly

Condo

Summer Deal Wailea Villa with Golf Course Views and Resort Pools

Wailea, Hawaii, United States

Some of the features include: Travertine Tile, Granite, Marble, Top of the line Stainless Steel Appliances, Mahogany Cabinets, Luxury, Quality Furniture, Plush Carpeting, Air Conditioners in all rooms, and Mirrors throughout. This is truly a perfect getaway!brbrThis extraordinary villa boasts a large Primary Bedroom and Bath with a total of 1182 square feet of living and lanai area! The main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the shores of Maui. Inside, the primary and guest bathrooms, a large shower, double sink, and ample closets bring unexpected convenience and versatility to this villa.brbrGrand Champions is located in the wonderful settings of the Wailea Blue Course, surrounded by tropical landscaping, two pools, a Jacuzzi, and BBQ areas.brbrWithin walking distance to the famed Wailea Tennis Club, Shops at Wailea, Wailea Town Center, Restaurants, and Numerous Top Rated World Class Beaches.brbrIf you are looking for a perfect getaway in paradise, this is it!brbrPlease note, only one vehicle is allowed for this unitbrbrWhile 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.brUpdate 5/22: Dryer Vent Cleaning taking place between 8/3-8/13. brHawaii Tax ID #: 127-100-9280-01

Bed

Bath

Sleeps

$513.5

/ Nightly

Condo

360 Premier Ocean View! Remodeled Ekolu # 1510!

Wailea, Hawaii, United States

This is a premier unit with panoramic ocean views located just minutes to all Wailea Beaches, The Shops at Wailea and Luxury Hotels! This beautiful condo is fully remodeled with tasteful furnishings, top of the line appliances, exquisite cabinetry, upgraded bathrooms and granite countertops. Relax and unwind in this beautiful unit that is perfect for couples or a family.brbrThe main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the Shores of Maui. Very bright and spacious to take advantage of indoor, living. This top floor fully air-conditioned 2 bedroom unit is situated in the premier front row of a highly sought after complex in the prestigious Wailea Ekolu Village. The Hawaiiana furnishings add a comforting atmosphere for a relaxing stay. Picture a wonderful afternoon while sipping away at a tropical beverage while you take in the sun at the Fairway pool.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, Kahoolawe, Molokini and West Maui Views! You may also see whales during the winter season. This beautiful villa is one of a kind!brbrWhatever your vacation desires, this condo will be everything you can imagine and more to create memories for a lifetime!brbrPropane grills are no longer allowed at Wailea Ekolu but the property has charcoal grills located throughout for your use.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 accessUnit 1510 is just steps away from the pool and just minutes to the Wailea Beaches, Shops at Wailea and luxury hotels! This unit is very private and peaceful and so serene! Perfect for couples or family.Other things to notePlease note: Upon confirming your reservation, we will request your personal email address. A company specific rental agreement will be emailed to the provided address. Once we have received your completed rental agreement, detailed arrival instructions will be emailed to you one week prior to your stay.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.brbrRegistration number210080770129, TA-183-962-9824-01

Bed

Bath

Sleeps

$435.26

/ Nightly

Condo

360 Ocean Views + Full Remodel! Top Floor # 904!

Wailea, Hawaii, United States

When 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. This beautiful ocean view home is one of a kind!!brbrWatch the sunset from every room!! This top floor unit is situated in the premier front row of this highly sought after complex. The main living area boasts expansive high beam ceilings that add to the wonderful flow of air blowing in off the shores of Maui. The Hawaiiana furnishings add a comforting atmosphere for a relaxing stay. Picture a wonderful afternoon while sipping away at a tropical beverage while you take in the sun at the Fairway pool.brbrGreat location and convenience!! Walk along the Ekolu walkway pass to the World's Top Beaches, Shops at Wailea, Five Star Hotels, casual to fine dining restaurants and more. Please note this unit can accommodate 1-2 adults only.brbrRAVE REVIEWS!brGorgeous view and unit! Perfect couple's getaway! Rated 5 of 5brMy husband and I stayed here for a week to celebrate our 25th wedding anniversary. As soon as we stepped into the unit, we felt instantly welcomed by an unexpected gift basket containing Maui snacks from the owners. The furnishings were impeccably clean and well-kept, and the wood ceiling and floors made the place feel homey and inviting. The kitchen appliances were new and all in working order. Similarly, the pots/pans, cooking utensils, and dinnerware were all in good shape which is not always the case in rentals. This made it very pleasant to cook meals when we decided to eat in. The view from the lanai is incredible and it is so pleasant to sit outside with the breeze and enjoy the sunset with a drink in hand. We were incredibly impressed by the unit and would definitely stay here again.brStayed: Jul 2017brbrIncredible 24 day stay! Rated 5 of 5.brWe have just finished a 24 day stay and it was fantastic. We enjoyed this condo so much. Sitting on the lanai in the mornings and watching the sunsets in the evenings will be especially memorable. The attention to detail was superb. It was absolutely spotless which meant a lot to us.brStayed: Aug 2016brbrWow! Rated 5 of 5.brWe arrived Saturday Oct 10, 2015 and by the 12th reserved another 9 days in Dec 2016. It's hard to imagine paying more to stay at the Grand Wailea Hotel when I am looking right over it from unit 904 at Ekolu Village. Privacy, upgraded... 904 doesn't disappoint....brStayed: Oct 2015brbrAwesome ! Rated 5 of 5.brWe were pleasantly surprised about the whole package! Very clean, well appointed, most comfy king bed, amazing views, quiet, awesome stargazing at night, completely private! We've stayed in hotels typically, but with this home, you receive the benefits of quietude, no hotel business, cook or not at your leisure and short distance to many wonderful beaches!brStayed: Sep 2014brbrWhile 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 accessGreat location and convenience!! This beautifully appointed home situated on the Fairway of Wailea's elite Blue Golf Course allows you to take advantage of special golf and tennis rates offered to guests. Walk along the Ekolu walkway pass to the World's Top Beaches, Shops at Wailea, Five Star Hotels, casual to fine dining restaurants and more...Other things to notePlease note: Upon confirming your reservation, we will request your personal email address. A company specific rental agreement will be emailed to the provided address. Once we have received your completed rental agreement, detailed arrival instructions will be emailed to you one week prior to your stay.br*Split A/C in Living Room and Primary Bedroom*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.brRegistration number210080770076, TA-134-586-7776-01

Bed

Bath

Sleeps

$556.61

/ Nightly

Condo

Wailea condo w/ pool, spa and ocean views near beach

Wailea, Hawaii, United States

This cool, ground floor condominium is the most spacious 1200 sq ft two-bedroom 'C' plan, with sunken living room, brand new designer furniture, and extensive travertine and granite surfaces. Oceanic Time Warner cable, internet, phone, and Wi-Fi.brbrBoth kitchen and living room are completely remodeled! The primary bedroom has a king-size bed and free-standing travertine bath, with a separate shower room. The second bedroom has 2 twin beds and a full separate bathroom. Washer/dryer in unit. There is a large garden Lanai for outdoor dining and entertaining.brbrSpacious luxury suite! Close proximity to the Clubhouse pool and spa! This spacious covered lanai with a dining table and private BBQ allow for relaxing evenings while you kick back and enjoy the views. Relax poolside or take a Jacuzzi after the sun sets and take in the beauty of the brilliant Maui skies. Seconds to Wi-Fi-equipped lounge, beautiful pool, and spa. Jewel-like Ocean views from the clubhouse which is just a step away.brbrMaui's most exclusive location with the best weather is the award-winning Wailea Resort. Ideally situated just uphill from gorgeous Keawekapu Beach, The Palms at Wailea is an architect-designed two-story-only complex with charming Mediterranean accents, and beautifully-manicured grounds, including two lily ponds joined by a charming stream. It's an easy walk to the luxury 'Shops at Wailea and many fine restaurants. Five world-class golf courses and tennis club nearby.brbrPlease note that Palms at Wailea no longer allows private grills. There will not be a grill for you to use on the lanai of this condo.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.brbrWe would like to inform you that the pool at the Palms of Wailea will be temporarily closed from September 16th to 19th for cleaning and resealing of the pool surface to ensure a safe environment for everyone. To further prevent future closures, we have also scheduled a drainage of the pool during this time to repair pool equipmentbr5/12/25 Update: Pool Closure NoticebrNotice 2/18/26 - Pool Closure: Tuesday, Sept,. 15th -Friday, Sept,.18th 2026brThe Pool Area Will Reopen Saturday September 19th with Regular HoursbrHawaii Tax ID #: 152-503-2960-01

Bed

Bath

Sleeps

$325.2

/ Nightly

Condo

Experience the ultimate tropical getaway at Grand Champions 067, a stunning one-

Wailea, Hawaii, United States

Welcome to the serene and luxurious Grand Champions 067, your ideal retreat in Wailea. This beautifully designed one-bedroom, one-bathroom condo offers a perfect blend of comfort and elegance, ideal for a family getaway. The spacious living room features a queen sofa sleeper, providing a cozy space for relaxation or additional guests. The master bedroom is equipped with a plush king bed and a private en-suite bathroom, ensuring a restful night's sleep.brbrStep outside onto the private balcony and enjoy the partial ocean views while you sip your morning coffee, prepared with the convenience of a coffee maker. The fully equipped kitchen includes modern appliances such as a refrigerator, microwave, stove, and dishwasher, making it easy to prepare meals during your stay. brbrGrand Champions 067 offers premium amenities including a communal pool, BBQ area, and free on-site parking. Enjoy the convenience of Wi-Fi, cable TV, and a DVD player for your entertainment needs. Linens, towels, and essential toiletries are provided, ensuring a hassle-free stay.brbrLocated in Wailea Grand Champions, this condo is just a short distance from some of Maui's most popular attractions. Explore the stunning Wailea Beach, indulge in world-class shopping at Wailea Beach Shops, or embark on a whale-watching adventure during the winter months. The nearby Wailea Tennis Club and Wailea Golf Course offer recreational activities for all ages.brbrExperience the perfect blend of luxury, comfort, and convenience at Grand Champions 067. Book your stay today and create unforgettable memories in this beautiful paradise.brbrResort 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 brPi'ilani Shopping center (10min): br• Safeway grocery store br• Food Court (Subway, Coldstone Creamery, etc.) br• Ross Dress For Lessbr brBeaches: br• Ulua Beach (5 min drive) br• Makena Beach (15 min drive) br• Polo Beach (5 min 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 Plantationbrbrbr30+ min drive upcountry br• Kula Ali'i Lavender Farm br• Ocean Vodka Organic Farm and Distillerybr• MauiWine Winery br• Surfing Goat Dairy br• Piiholo Ranch Ziplinebr brDistance to Airport: 16 miles, approximately 26 minutes brbr**Not ADA accessible

Bed

Bath

Sleeps

$987.96

/ Nightly

Condo

Beachfront Wailea condo w/ ocean views and lanai

Wailea, Hawaii, United States

Magnificent ocean views from Polo Beach Club 705, with direct beach access! Enjoy the serenity and privacy of one of the best locations in Wailea.brbrAs you enter Polo Beach Club 705 you are greeted by the lovely furnishings and decor. You will be drawn to the breathtaking views from this expansive private lanai. Spend your days gazing off at the beautiful blue waters, Molokini and the West Maui Mountains. Dine alfresco or lounge with your favorite book. The floor to ceiling sliding glass doors offer seamless indoor/outdoor living.brbrThe living area is open and welcoming. A great place to gather and listen to the serene sound of the ocean or enjoy a movie. Complete with sectional, large flat screen TV, and ceiling fan.brbrThere is a dining area with seating for six. The eat up bar allows for additional seating.brbrThe Kitchen is fully equipped with stainless steel appliances, beautiful white counters, plate ware and utensils as well as all of the cooking items any chef would need.brbrYour primary bedroom offers gorgeous ocean views and access to the private lanai. There is a king bed with luxurious linens, flat screen TV, and ensuite bath. The primary bath offers a nice vanity area, walk-in tiled shower, and plenty of closet space.brbrYour guest bedroom is beautifully decorated with two queen beds, flat screen TV, and ceiling fan. The guest bath is located conveniently just off the guest bedroom.brbrFull-size washer and dryer allow for lighter packing.brbrCentral AC throughout makes this condo comfortable all year round.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.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#: 065-197-0560-02

Bed

Bath

Sleeps

$360.16

/ Nightly

Condo

Luxury on a Budget at Grand Champion Villas #118 - 2 Bd+2 Bath-

Wailea, Hawaii, United States

Bldg. 13 - Unit #118 - wonderful upgrades in a comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South Maui, nestled between the championship Ol’ Blue Golf Course and the award winning Wailea Tennis Center. Lush tropical gardens and swaying palm trees surround all 188 units, two swimming pools, two Jacuzzis and four gas BBQ grills to enjoy. Shopping, dining, activities, and amenities are conveniently located within walking distance. Beautiful Wailea beaches are just a short drive away or a 15–20-minute walk from the Villas. Wailea Grand Champions Golf Villas offers great values and views in the heart of the upscale Wailea Resort community. This moderately priced, luxury property is in the center of Wailea’s Ol’ Blue Golf Course, with contemporary villas featuring private lanais for sunset views over the fairways to the West Maui mountains. Wailea area resorts, spa facilities, and award-winning restaurants are within walking distance, and Wailea’s fabulous beaches are a leisurely 15-minute walk or easy 3-minute drive from the Wailea Grand Champions Villas. Wailea Gateway Center, Wailea Town Center, The Shops at Wailea, and the newest shopping/entertainment destination Wailea Village Center are all a few minutes’ walk from your vacation home at Wailea Grand Champions.brbrBeach chairs, beach towels, beach umbrella, and coolers are provided. Additional beach gear may be rented at one of our local beach shops.brbr** Please note **brAll Holiday Season reservations are due, paid-in-full on October 1st. Holiday season is 12/15 to 1/10brNo refunds on Holiday Season cancellations after October 1st.brFurnishings, fixtures, and equipment are subject to change as necessary or preferred by client and may not be exactly as pictured.

Bed

Bath

Sleeps

$342.17

/ Nightly

Condo

Private and Sweet Wailea 1 BD+2 BA Grand Champions Villa

Wailea, Hawaii, United States

New Furniture! New personal amenities! new soft goods! Unit #54, building 6. An impeccable 1 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. Wailea Grand Champions Golf Villas is in the heart of the Wailea Resort Community in sunny South Maui, nestled between the championship Ol’ Blue Golf Course and the award winning Wailea Tennis Center. Lush tropical gardens and swaying palm trees surround all 188 units, two swimming pools, two Jacuzzis and four gas BBQ grills to enjoy. Shopping, dining, activities, and amenities are conveniently located within walking distance. Beautiful Wailea beaches are just a short drive away or a 15–20-minute walk from the Villas. Wailea Grand Champions Golf Villas offers great values and views in the heart of the upscale Wailea Resort community. This moderately priced, luxury property is in the center of Wailea’s Ol’ Blue Golf Course, with contemporary villas featuring private lanais for sunset views over the fairways to the West Maui mountains. Wailea area resorts, spa facilities, and award-winning restaurants are within walking distance, and Wailea’s fabulous beaches are a leisurely 15-minute walk or easy 3-minute drive from the Wailea Grand Champions Villas. Wailea Gateway Center, Wailea Town Center, The Shops at Wailea, and the newest shopping/entertainment destination Wailea Village Center are all a few minutes’ walk from your vacation home at Wailea Grand Champions.brbrBeach chairs, beach towels, beach umbrella, and coolers are provided. Additional beach gear may be rented at one of our local beach shops.brbr**Please note**brAll Holiday reservations are due, paid-in-full on October 1st. Holiday season is 12/15 to 1/10brNo refunds on Holiday cancellations after October 1st.brbrDiscounts for 14-day and 30-day stays are already included in total price shown.

Bed

Bath

Sleeps

$1263.61

/ Nightly

Condo

Makena Surf F207 Beachfront Resort

Wailea, Hawaii, United States

Welcome to the Makena Surf F207, where luxury meets the ocean's edge. This beautifully renovated 2-bedroom, 2-bathroom oceanfront condo is perfect for your dream Maui getaway. The spacious 1,313 square foot open features floor-to-ceiling windows that bring the ocean views and natural lighting into the living room, kitchen, and dining area.brbrSpend gentle mornings on your lanai sipping coffee and gazing out at the ocean reefs that front the condo. Search for turtles patrolling the reefs, dolphins playing offshore, or even humpback whales breaching during the winter months. Take in the panoramic and unobstructed ocean views that include the nearby islands of Molokini and Lana’i as well as the dramatic West Maui Mountains. Sunsets are equally memorable! Take advantage of the BBQ on the lanai to grill up fresh caught local fish as you enjoy the sunset from the comfort of your oceanfront vacation rental.brbrModern furnishings, island-inspired décor (including a wall-mounted surfboard) and well-thought-through amenities combine to enhance your comfort. The gourmet kitchen featuring granite countertops and stainless steel appliances is equipped with all the cooking gadgets your are accustomed to back home. Whip up macadamia nut pancakes and take them to the formal dining table or dine al fresco on the lanai.brbrThe primary bedroom is equipped with a king bed and a fully remodeled en suite bathroom featuring his and her sinks and an oversized walk-in rain shower. The second bedroom has two double beds. Both bedrooms have additional flat screen TVs for viewing your favorite programming before falling to sleep. A remodeled full bathroom down the hall is easily accessible by the guest bedroom.brbrThe Makena Surf Resort offers a range of premium amenities, including access to two pools, hot tubs, tennis courts, and BBQ areas featuring fresh herb gardens. Walk out to the beach that fronts this cluster of Makena Surf condos for some of the best snorkeling on the island! It is not uncommon for snorkeling boats to stop out front. For those that enjoy catching waves, it is also one of the safest beaches for boogie boarding. brbrLocated in Makena, you'll be just a short distance from the resort town of Wailea. Top restaurants, spas, golf courses, shopping, and beaches are a short 10-minute drive away!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:brbr - 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.

Bed

Bath

Sleeps

$351.96

/ Nightly

Condo

Summer Deal Wailea 2BR Condo with Lanai Pools and Beach Access

Wailea, Hawaii, United States

Incredible Renovation! Kick back and relax on your own private lanai and take in wonderful garden views, with some ocean and mountain views. Feel the wonderful trade winds and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This spacious two-bedroom unit in the Grand Champions Villas comes fully stocked with all the amenities needed to make you feel as if you are in your own home.brbrThe Primary bedroom features a king bed and an ensuite with an amazing walk-in shower! The secondary bedroom has two twin beds that can be converted into a king bed upon request and an ensuite bathroom. Ground floor access makes trips to and from the beach, golf course, tennis courts, and pool a breeze!brbrLocation! Location! Location! The Grand Champions have lush beautiful landscaping and amenities include two pools, Jacuzzi, BBQ, and Security. This central Wailea location makes it favorable as you can walk to tennis, Shops at Wailea, casual to fine restaurants, world's top beaches, and five-star hotels.brbrParking available on propertybrbrWhile 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 Bedrooms Only*brHawaii Tax ID #: 056-304-4352-02brbrUpdate 5/22: Dryer Vent Cleaning taking place between 8/3-8/13.

Bed

Bath

Sleeps

$1245.48

/ Nightly

Condo

Oceanfront Maui condo w/ pool, hot tub and lanai views

Wailea, Hawaii, United States

Book Your Stay and Get a $300 Gift Card!brbrPlanning a getaway Book a stay of 5+ nights between September 24th and November 9th, and you'll receive a $300 gift card to enjoy at some of the best spots around! Choose from Cafe O Lei, Kohola Brewery, or Cool Cats to indulge in amazing food, craft brews, or the best burgers in town.brbrDon't miss out – book your stay now and treat yourself to an unforgettable experience!brbrCaptivating Ocean Views from Polo Beach Club 805! Direct ocean front location with beach access.brbrYou will marvel at the exquisite furnishings and decor at Polo Beach Club 805.brAs you enter, you are greeted by the sophisticated style of this beautiful ocean front condo.brbrThe Kitchen is fully equipped with stainless steel appliances, beautiful white counters, plate ware and utensils as well as all of the cooking items any chef would need.brbrAs you settle into the living area, you can relax to the soothing sound of the ocean. There is a large sectional with plenty of seating for the whole family. Enjoy your favorite movie on the flat screen TV.brbrThere is a dining area with seating for four and an eat-up bar for additional seating.brbrThe floor-to-ceiling sliding glass doors allow for seamless indoor/outdoor enjoyment. The private grand lanai offers plenty of space to enjoy your favorite beverage and lounge. Gaze off at the mesmerizing views of Molokini, Kaho'olawe, and the West Maui mountains.brbrYour primary bedroom offers gorgeous ocean views and access to the private lanai. There is a king bed with luxurious linens, flat screen TV, and ensuite bath.brbrThe primary bath offers a nice vanity area, walk-in tiled shower, and plenty of closet space.brbrYour guest bedroom is beautifully decorated, with two queen beds, flat screen TV, and ceiling fan. The guest bath is located conveniently just off the guest bedroom.brbrFull-size washer and dryer allow for lighter packing.brbrCentral AC throughout makes this condo comfortable all year round.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.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 TAX ID: 061-702-3488-03

Bed

Bath

Sleeps

$531.09

/ Nightly

Condo

Communal Pool, Balcony w/ View & Walk to Beach | Wailea Ike by AvantStay

Wailea, Hawaii, United States

Pack your swimwear and prepare for an unforgettable getaway at this newly renovated condo, where every morning greets you with stunning balcony views of lush landscapes rolling down to the ocean. This condo is within walking distance of the beach, the Wailea shops, top-tier restaurants, the Wailea Tennis Club, and multiple golf courses.brbrPerfectly positioned near several pristine beaches, this condo offers easy access to sun-soaked sands and crystal-clear waters. Enjoy the outdoors with a leisurely stroll through nearby parks or a round of golf on a nearby course, with the ocean breeze keeping you company. Head north for a snorkeling adventure or marvel at marine life at the local aquarium. When hunger strikes, savor delicious meals at waterfront restaurants where the cuisine is as spectacular as the views. brbrYour Hawaiian holiday offers more than just beach days. Take a dip in the community pool, relax in the hot tub, or rally for a game of tennis on the courts.brbrAfter a day of island adventures, retreat to your freshly remodeled living space, meticulously updated from top to bottom and boasting a queen-size pullout sleep sofa. The gourmet kitchen is a baker's dream, equipped with high-end stainless steel appliances, stunning stone countertops, and a vibrant tile backsplash. Create culinary delights, then gather at the dining table or enjoy a meal alfresco on the balcony with ocean views.brbrThe renovations extend to both bathrooms, featuring waterfall showers and a luxurious soaking tub in the primary bath. Wind down your evening by watching your favorite shows on the flat-screen TV and then drift into a restful sleep.brbrExperience the ultimate Hawaiian escape at this beautifully renovated condo, where comfort and luxury meet paradise.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrMaui, known as the Valley Isle, is an idyllic vacation destination that captivates with its breathtaking landscapes and vibrant culture. Whether you're drawn to the sun-drenched beaches, the lush rainforests, or the stunning Haleakalā National Park, Maui offers an unparalleled blend of natural beauty and adventure. Imagine exploring the famous Road to Hana, snorkeling in the crystal-clear waters of Molokini Crater, or enjoying a traditional Hawaiian luau under a canopy of stars. With its warm aloha spirit, world-class resorts, and diverse activities, Maui promises a magical experience catering to relaxation and excitement. Perfect for families, couples, and solo travelers alike, Maui's charm lies in its ability to provide unforgettable moments and lifelong memories.brbrHome Truths:br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval, there is a fine of $500 per pet.br- There is no heating at this home.brbrParking Details:br- Parking is available for 1 vehicle.brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 28 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

2

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Wailea, HI

$554.76

$642.25

$377.47

$428.21

$543.65

$547.5

$543.65

$565.93

$354.44

$513.5

$435.26

$556.61

$325.2

$987.96

$360.16

$342.17

$1263.61

$351.96

$1245.48

$531.09

Rent a place that suits your needs

Most popular vacation rentals in Wailea

$3135.26

$2565.93

$2710.81

$2758.28

$2773.92

$2792.72

$2885.87

$4122.13

$3843.19

$3715.03

Most Popular Cities in Hawaii