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Upscale Wailea Coast
Stay in Wailea for upscale South Maui rentals near beaches, golf, dining, snorkeling, spas, and island activities.
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Browse related Wailea vacation rental pages, resort pages and nearby places to stay.
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Walk to Beach, Ocean Views, Relax by the PoolFrom $881/night · Sleeps 10
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈From $229/night · Sleeps 4
NEW KITCHEN REMODEL! Amazing View!From $360/night · Sleeps 4
The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner...From $1,080/night · Sleeps 6
125+ 5star REVIEWS SAYS IT ALL! Golf & Ocean! LAST...From $224/night · Sleeps 2
Wailea Ekahi 40A - 5-Star South Maui OasisFrom $350/night · Sleeps 4
Amazing view, Close to the beach, Wailea Ekahi Unit 20iFrom $359/night · Sleeps 4
Wailea Beach Villas Penthouse K107 – Maui Luxury with Island...From $859/night · Sleeps 6
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 DFrom $375/night · Sleeps 2
14D Panoramic ocean view, beautiful sunset every night. Best in...From $635/night · Sleeps 2
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd...From $1,970/night · Sleeps 8
Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea...From $353/night · Sleeps 4
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!From $320/night · Sleeps 6
No stairs inside or out! Beautifully remodeled Palms at Wailea...From $358/night · Sleeps 4
Stunning Ocean View Wailea Beach Villa- Book & SaveFrom $1,911/night · Sleeps 9
'Best Vacation Ever' Say Our Guests! Special May RatesFrom $325/night · Sleeps 6
Amazing House with Pool, Spa, Cabana & More Kihei Wailea...From $1,168/night · Sleeps 10
Luxury Wailea Family Condo. Complete Remodel! AC and Pool.From $382/night · Sleeps 6
Wailea, Oceanfront, Polo Beach Club Condo #403From $980/night · Sleeps 5
Ocean View, Steps away from the poolFrom $535/night · Sleeps 4
Summer Deal Wailea Villa with Ocean Views and Private LanaisFrom $964/night · Sleeps 8
Modern and Luxurious Beachfront Property at Polo BeachFrom $915/night · Sleeps 4
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!From $233/night · Sleeps 4
Fantastic unit! 10/10! Hear the waves from the lanai! 1...From $250/night · Sleeps 4
Only Steps to Ulua Beach and the main Wailea Ekahi...From $311/night · Sleeps 4
Stunningly Renovated! Ocean View! Elua 2305From $983/night · Sleeps 4
Beautiful Sunsets with this Ocean View Condo! Mar 23 -...From $275/night · Sleeps 4
Luxury at its Best with Big Ocean Views!!From $475/night · Sleeps 4
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third...From $999/night · Sleeps 8
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC,...From $897/night · Sleeps 6
Full Ocean View WaileaFrom $405/night · Sleeps 3
Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century ModernFrom $455/night · Sleeps 2
Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium...From $601/night · Sleeps 6
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion...From $315/night · Sleeps 6
Nicely Updated-Sleeps 8-WELL Equipped-Ac-Meticulous CleaningFrom $552/night · Sleeps 8
Oceanfront Maui condo w/ pool, hot tub and lanai viewsFrom $1,399/night · Sleeps 6
Wailea Elua 3 Bedroom+2 Bath Spacious Beach Home with Oceanview...From $806/night · Sleeps 6
Summer Deal Ocean View Wailea Villa with Pool and Resort...From $1,010/night · Sleeps 8
Summer Deal Wailea Condo with Lanai Pool and Golf Course...From $372/night · Sleeps 6
100KContemporaryHawaiian Reno in Wailea-Beach/GolfFrom $341/night · Sleeps 6
Stunning NEW Remodel-Sunsets-Luxury-Quiet Location-Ac-Large LanaiFrom $300/night · Sleeps 4
Luxurious Ho'olei Villa with Ocean Views, Two Story Townhouse!From $1,548/night · Sleeps 6
Oceanfront Maui condo w/ sunset lanai and pool accessFrom $455/night · Sleeps 2
Elegant Wailea Renovated 2BR Condo Panoramic Ocean and Haleakala Views...From $782/night · Sleeps 6
Panoramic Views - Fourth Row Ho'olei - One of a...From $1,099/night · Sleeps 8
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical...From $331/night · Sleeps 6
Wailea condo w/ lanai, pool and Keawakapu Beach accessFrom $347/night · Sleeps 6
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu BeachFrom $411/night · Sleeps 4
Wailea Elua 1101 - Beachfront Section - Ocean View -1...From $847/night · Sleeps 4
Luxurious Wailea 2BR Condo Full Ocean and Fairway Views Two...From $373/night · Sleeps 4
2nd Floor Ocean Views | Epic Sunsets | Makena Surf...From $830/night · Sleeps 6
Walk to Beach in Seconds - Makena Surf B106From $1,236/night · Sleeps 6
Sunset & Ocean Views | Platinum RatedFrom $409/night · Sleeps 4
Modern Renovation with Ocean Views | Wailea Elua 905From $1,351/night · Sleeps 8
Wailea oceanfront condo w/ Keawakapu Beach accessFrom $437/night · Sleeps 4
Wailea Villa Overlooking Lagoon PoolFrom $1,437/night · Sleeps 8
Spacious Ocean View Condo - Perfect For FamiliesFrom $360/night · Sleeps 6
3BD Golf Haven - Great for FamiliesFrom $369/night · Sleeps 7
Top Floor Wrap-Around Ocean Views - PH512From $1,575/night · Sleeps 6
Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous KiheiFrom $336/night · Sleeps 6
Large Floorplan - Great for Families | Grand Champions 159From $330/night · Sleeps 8
Wailea Elua: Huge Ocean Views, Pool, AC & Hot TubFrom $690/night · Sleeps 6
Oceanviews, Fresh Upgrades at the Luxurious Grand Seascape K407!!From $1,566/night · Sleeps 6
Voted Top 10 Resort in Hawaii - Wailea Beach Villas...From $1,764/night · Sleeps 8
Elevated 8th Floor Ocean Views | Polo Beach 801From $632/night · Sleeps 4
Beachfront condo Wailea w/ pool and hot tub accessFrom $468/night · Sleeps 6
Wrap-Around Beach & Ocean Views | Polo Beach 301From $823/night · Sleeps 6
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea...From $449/night · Sleeps 6
Oceanfront Polo Beach 407 - Professionally ManagedFrom $608/night · Sleeps 6
Floor to Ceiling Ocean Views - Wailea Elua 2006From $789/night · Sleeps 6
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025From $999/night · Sleeps 8
Recently Renovated - Walk to the BeachFrom $424/night · Sleeps 4
Beachfront Condo with Postcard ViewsFrom $779/night · Sleeps 4
Elevated Beachfront Views - Wailea Elua 1704From $1,051/night · Sleeps 6
Watch the Golfers Play ThroughFrom $273/night · Sleeps 4
Elegant Wailea Remodeled 2BR Condo Saltwater Pool Steps to Keawakapu...From $508/night · Sleeps 6
Walk to Waves, Snorkeling, Dining | Polo Beach 409From $580/night · Sleeps 6
Beachfront Condo with Postcard Views - Makena Surf F306From $892/night · Sleeps 6
3BD Wailea Villa - Great for Families | Wailea Beach...From $1,219/night · Sleeps 8
Penthouse Retreat Walk to Wailea BeachFrom $1,352/night · Sleeps 6
Hear the Waves Crash - OceanfrontFrom $1,795/night · Sleeps 6
Recent Renovation - Close to Golf & DiningFrom $283/night · Sleeps 6
Stunning ocean view! 2/2 in the heart of WaileaFrom $335/night · Sleeps 5
Wailea Ekahi Village 12C - 1 Bedroom Ocea View CondoFrom $387/night · Sleeps 4
Walk to Waves, Snorkeling, Pool - Wailea Elua 910From $533/night · Sleeps 4
Recently Renovated - Steps from SnorkelingFrom $619/night · Sleeps 6
Sunset Views | Whale Watching | Resort Amenities - Wailea...From $724/night · Sleeps 4
Beachfront Condo – Hear the Waves Crash | Makena Surf...From $824/night · Sleeps 6
Wailea Elua 1603: Premier Views, Exquisite Updates!From $1,276/night · Sleeps 4
Conde Nast Award Winning Property - Wailea Beach Villas E202From $1,667/night · Sleeps 8
Ocean Views | Tropical Decor | Professionally ManagedFrom $342/night · Sleeps 6
Prime Location | Snorkeling | Wailea Beach PathFrom $613/night · Sleeps 2
Bright & Colorful Ocean View Villa | Wailea Beach Villas...From $1,036/night · Sleeps 4
Recently Renovated & Professionally Managed Ocean View VillaFrom $1,770/night · Sleeps 8
Golf + Partial Ocean Views - Grand Champions 71From $238/night · Sleeps 4
Ocean Views | Close to Wailea Golf & BeachesFrom $272/night · Sleeps 4
Wailea Ekahi 11C | Snorkeling & Waves Out FrontFrom $328/night · Sleeps 6
Golfer's Dream | Condo on Wailea CourseFrom $338/night · Sleeps 6
Sunset Ocean Views | Whale Watching | Wailea Ekahi 38BFrom $356/night · Sleeps 4
Meticulously Designed | Platinum Rated | Ocean ViewFrom $369/night · Sleeps 4
Wailea Ocean Views | Great for FamiliesFrom $371/night · Sleeps 6
Modern Renovation with Ocean ViewsFrom $478/night · Sleeps 6
Tiki Tiki - A Gorgeous Boho Beach Hideaway!From $520/night · Sleeps 2
Newly Remodeled-Quiet Location-Ac-Well Equipped-Meticulous CleaningFrom $568/night · Sleeps 8
Exceptional Design & Ocean ViewsFrom $905/night · Sleeps 6
Spacious Condo in Heart of WaileaFrom $237/night · Sleeps 6
Golfer's Dream | Condo on Wailea CourseFrom $258/night · Sleeps 4
Recently Renovated & Professionally ManagedFrom $283/night · Sleeps 4
Spacious Condo on Favorite Local BeachFrom $318/night · Sleeps 4
Stylish Beach Studio - Professional ManagedFrom $328/night · Sleeps 2
Enhanced Design & Comfort - Ekahi 42CFrom $352/night · Sleeps 4
Recently Renovated Ocean View - Platinum RatedFrom $392/night · Sleeps 4
Recently Renovated - Walk to the Beach - Elua 1102From $683/night · Sleeps 4
Wailea Elua 2004 | Hot tub | Pool | Sunset...From $740/night · Sleeps 4
Spacious Condo on Top Snorkeling BeachFrom $779/night · Sleeps 6
Wailea Villa in Top-Rated Hawaii ResortFrom $815/night · Sleeps 6
Walk to Waves, Snorkeling, & RestaurantsFrom $854/night · Sleeps 4
Tropical Ocean & Pool ViewsFrom $855/night · Sleeps 6
Spacious Condo - Great for FamiliesFrom $881/night · Sleeps 8
Recently Renovated - Oceanfront in WaileaFrom $1,064/night · Sleeps 4
From $881/night
- Luxurious two-story townhome with a private elevator and sleeps 10 comfortably- One of the few villas offering both pool and ocean views- Prime...
From $229/night
Wailea Grand Champions Villas -- Condo #188Aloha!You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of...
From $360/night
Condo, 1 bedroom + other (See Description) 2 baths (Sleeps 4)Peace of mind is important for where you are staying. Our cleaning care professionals...
From $1,080/night
The Maui Escape is located with views of the upper pool and the spectacular surroundings. The villa's location is the perfect combination of being...
From $224/night
Location: Grand Champions, Wailea, South Maui, Maui, Hawaii, USA (2 miles Kihei, 13 miles airport, 1/2 mile beach.) Accommodations: Condominium, 1...
From $350/night
*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...
From $359/night
Condo 1 bedroom, 2 bath (sleeps 4)PRIME location on the front row in lower Wailea Ekahi, Wailea. Listen to the sound of the waves and enjoy the ocean...
From $859/night
Welcome to Wailea Beach Villas Penthouse K107 - A luxurious and spacious 2-bedroom, 2-bath with a den that functions as a workspace or third bedroom...
From $375/night
Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with...
From $635/night
Wailea Ekahi #14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this...
From $1,970/night
4 Full Bedrooms & 3 Full Baths; Total 3892 S.F Beachfront Wailea: Ocean Panoramic & Outer Island Views, Penthouse K-208IMPORTANT: Maximum 8 Adult...
From $353/night
Aloha!Start your day with coffee and beautiful ocean views from the lanai, and finish the day watching amazing sunsets!Welcome to our Our Maui Condo!...
From $320/night
If you’re looking for a modern, quiet, luxurious Wailea retreat, this is it! Unit #1204 was completely gutted to the studs and rebuilt with comfort,...
From $358/night
NO STAIRS INSIDE OR OUT!Welcome to Palms at Wailea 503, your beautifully remodeled sanctuary in paradise! This is a two-bedroom two-bathroom condo in...
From $1,911/night
Most popular Maui Condo Wailea Beach Villa L409 Rated Perfect . 4BR (3 Kings/1 Queen, or 2 Kings/ 2 Twins/1 Queen) 3 BA villa . Spectacular panoramic...
From $325/night
You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining...
From $1,168/night
The Maui Meadows Guesthouse Property is 3/4 mile from (8) premier beaches and features: (4) Bedroom, (5) Bath one story 2700 sq ft house, Proximity...
From $382/night
Your Perfect Maui Family Retreat AwaitsExperience the ultimate in modern luxury at this completely renovated condo in Wailea. Just a 10-minute stroll...
From $980/night
Location, location, location…. Polo Beach is the premiere condominium that sits at the south end of the Wailea Beach walk, next to the Fairmont Kei...
From $535/night
IMPORTANT NOTICE: Pavilion Pool Deck resurfacing Project - August 10 to October 16, 2026.The pavilion facilities WILL be available, including...
From $964/night
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood...
From $915/night
Maui beachfront elegance Polo Beach Club is conveniently situated at the beginning of Makena and the Wailea oceanfront pathway that connects the...
From $233/night
Enjoy the exclusive Wailea lifestyle in this fashionably decorated, high-end suite with incredible ocean views!!!---This gorgeous, bright and...
From $250/night
This one bedroom/ one bathroom, smoke-free condo, is located in building 19 at Ekahi Village, and is a short (less than 4 minutes) relatively flat...
From $311/night
***PLEASE NOTE AUG 11 TO OCOTBER 15 THE MAIN POOL PAVILLION DECK IS BEING RESURFACED. If this vacation home is available, you'll want to reserve it....
From $983/night
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to Elua 2305. Your ultimate Maui vacation awaits at...
From $275/night
This beautiful top floor, Grand Champs condo has one of the best ocean views in the complex. This fully updated 2 bedroom, 2 full bath condo has...
From $475/night
Aloha & welcome to the Wailea Diamond Suite at Ekolu Village #305!The moment you step through the door you’ll know you’ve come home to luxury in this...
From $999/night
This villa at Ho'olei was renovated in 2024. The renovations are extensive. New extra large kitchen island with ocean view seating: all new...
From $897/night
Every detail was addressed in the complete and total renovation of this single-level luxury condo at Wailea Elua Village. Upon entering Wailea Elua...
From $405/night
Bright airy updated large 1 bedroom 2 bath top floor in sought- after Wailea Ekahi Village. 27D is a top corner unit known for our panoramic ocean...
From $455/night
Experience the beauty of Wailea from the moment you arrive in your spacious and stylish villa. Situated in a secluded position of the Grand Champions...
From $601/night
Wailea Elua Village #2301 is a premier vacation condominium located in Elua Village which is directly on the sugar sand of Ulua beach in Wailea. This...
From $315/night
Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that...
From $552/night
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that has been nicely updated. This condo is managed by PMI Maui, a local...
From $1,399/night
Book Your Stay and Get a $300 Gift Card!Planning a getaway? Book a stay of 5+ nights between September 24th and November 9th, and you'll receive a...
From $806/night
This is the one! If it's available, you'll want to reserve it. A real Maui home-away-from-home. New carpet in bedrooms, new bedroom furniture, lots...
From $1,010/night
Ho'olei Villa 17-1 is a beautifully remodeled 3-bedroom, 3.5-bath townhome offering stunning ocean views and breathtaking sunsets. Located in...
From $372/night
Location! Location! Location! Who needs a car?!? This central Wailea location makes it favorable as you can find tennis, golf, retailers at the Shops...
From $341/night
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in...
From $300/night
Book with confidence, this stunning, 1 bedroom, 2 bathroom (1022 sq. ft) condo that has been completely remodeled from top to bottom with modern...
From $1,548/night
This Ho'olei ocean view villa is a luxurious two-story townhouse in Wailea, offering sweeping ocean views and elegant island living. This spacious...
From $455/night
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...
From $782/night
For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly...
From $1,099/night
Newly Remodeled in 2023! Come relax and enjoy the spectacular ocean and island views in this rare three bedroom condo perched on the very top row...
From $331/night
Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your...
From $347/night
Welcome to Palms at Wailea 1904, a beautifully updated 2-bedroom, 2-bath vacation rental in the heart of Wailea. Perfect for families or couples...
From $411/night
Don't miss the best that Wailea Ekahi has to offer, 20G! Full kitchen and bathroom remodel, with all new appliances, Gorgeous! Stay with Wailea...
From $847/night
We are a 1 minute walk from the amazing Ulua Beach. You can see and hear the ocean from our condo. Relax viewing the ocean on a private, quiet lanai...
From $373/night
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and...
From $830/night
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor,...
From $1,236/night
Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean\'s edge. This beautifully...
From $409/night
Nestled in the prestigious Wailea Ekahi Village, condo 30D is an exquisitely decorated island-inspired vacation rental that offers a perfect blend of...
From $1,351/night
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a...
From $437/night
Located just moments away from the pristine beaches, this elegant condo offers the perfect balance of tranquility and convenience. Explore the nearby...
From $1,437/night
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the...
From $360/night
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning...
From $369/night
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. This spacious three-bedroom,...
From $1,575/night
Penthouse 512 at Wailea Beach Villas offers an unparalleled top-floor experience with expansive ocean and island views, ideal for a Hawaiian dream...
From $336/night
Located in the heart of Kihei, this condo is a dream. With 2 bedrooms featuring two king beds with ceiling fans, Queen size sleeper sofa in Living...
From $330/night
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This...
From $690/night
Summary:Nestled in the scenic beauty of Wailea, this inviting condo promises a delightful escape with everything you need for a memorable stay....
From $1,566/night
Situated in the centrally located "Penthouse" building on the 4th floor in a west-facing ocean view corner location with breathtakingly beautiful...
From $1,764/night
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious...
From $632/night
Perched on the top floor, this vacation home offers breathtaking views and a touch of sophistication. The spacious kitchen, featuring a central...
From $468/night
Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush landscaping makes this a...
From $823/night
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies...
From $449/night
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is...
From $608/night
Polo Beach Club 407 is a premier oceanfront vacation rental located in the upscale resort area of Wailea. This two-bedroom, two-bathroom condo offers...
From $789/night
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom,...
From $999/night
Remodel completed June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new...
From $424/night
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you...
From $779/night
Experience the ultimate Hawaiian getaway when vacationing at Wailea Elua 1301. This beautifully designed vacation rental featuring an open floor plan...
From $1,051/night
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious...
From $273/night
Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite property combines elegant...
From $508/night
** PLEASE NOTE: The Pool will be closed from September 15th - September 18th, 2026, for yearly maintenance. Welcome to The Palms at Wailea, where we...
From $580/night
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom,...
From $892/night
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the...
From $1,219/night
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or...
From $1,352/night
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy...
From $1,795/night
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront...
From $283/night
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant...
From $335/night
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and...
From $387/night
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers...
From $533/night
Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea community on Maui. This beautifully...
From $619/night
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired...
From $724/night
Wailea Point #3203 offers a luxurious and serene retreat with stunning ocean views, located in the exclusive gated community of Wailea Point. This...
From $824/night
Welcome to Makena Surf C207, a vacation rental nestled in paradise. This spacious suite offers a serene escape, featuring two large lanais surrounded...
From $1,276/night
Wailea Elua Village #1603 is an elegant ocean-view retreat offering one of the most private and scenic locations in Wailea. Thoughtfully updated with...
From $1,667/night
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly...
From $342/night
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains,...
From $613/night
Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the prestigious Wailea Elua...
From $1,036/night
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale...
From $1,770/night
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of...
From $238/night
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and...
From $272/night
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort....
From $328/night
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a...
From $338/night
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and convenience in the heart of...
From $356/night
Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start your morning on the lanai with...
From $369/night
This Wailea Ekahi Village residence completed a beautiful renovation in 2022. From colorful artwork to comfortable and sleek furnishings, you will...
From $371/night
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully...
From $478/night
Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This newly renovated, two-bedroom, two-bathroom beach house...
From $520/night
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise!A magical retreat that will have you feeling zen & refreshed. Tiki...
From $568/night
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all new furnishings. This condo is...
From $905/night
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with...
From $237/night
Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal...
From $258/night
Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style, comfort, and convenience....
From $283/night
Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairways, putting greens, and tee...
From $318/night
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo...
From $328/night
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit offers an elevated retreat with...
From $352/night
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to...
From $392/night
Make your Maui dreams come true at Wailea Ekahi 35D! This vacation rental is perched on the top floor with a private entrance surrounded by manicured...
From $683/night
This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to...
From $740/night
Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui\'s southern coastline. This one-bedroom, one-bathroom condominium...
From $779/night
Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea community on Maui\'s southern...
From $815/night
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms...
From $854/night
Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, two-bathroom condo offers an...
From $855/night
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view...
From $881/night
The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island of Maui. From the moment you...
From $1,064/night
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty...