Walk to Beach, Ocean Views, Relax by the PoolFrom $738/night · Sleeps 10
South Maui Luxury Villas and Condos
Wailea Vacation Rentals
Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden stay, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Hoolei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities right for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-quiet surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic stay or a long-term tropical escape, Wailea vacation rentals provide the right home base for a luxurious island experience.
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Wailea Vacation Rentals Listings
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Wailea Vacation Rentals Map
Walk to Beach, Ocean Views, Relax by the PoolFrom $738/night · Sleeps 10
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝From $235/night · Sleeps 4
The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!From $1,620/night · Sleeps 6
NEW KITCHEN REMODEL! Amazing View!From $470/night · Sleeps 4
125+ 5star REVIEWS SAYS IT ALL! Golf & Ocean! LAST MIN CANCL APRIL! 169 +tx rateFrom $332/night · Sleeps 2
Wailea Ekahi 40A - Your South Maui OasisFrom $369/night · Sleeps 4
Amazing view, Close to the beach, Wailea Ekahi Unit 20iFrom $359/night · Sleeps 4
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.From $1,436/night · Sleeps 8
Wailea Beach Villas Penthouse K107 – Maui Luxury with Island SerenityFrom $1,757/night · Sleeps 6
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!From $635/night · Sleeps 2
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!From $336/night · Sleeps 6
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 DFrom $375/night · Sleeps 2
Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu VillageFrom $425/night · Sleeps 4
Stunning Ocean View Wailea Beach Villa- Book & SaveFrom $2,095/night · Sleeps 9
No stairs inside or out! Beautifully remodeled Palms at Wailea 503From $689/night · Sleeps 4
Luxury Wailea Family Condo. Complete Remodel! AC and Pool.From $594/night · Sleeps 6
Amazing House with Pool, Spa, Cabana & More Kihei Wailea AreaFrom $1,336/night · Sleeps 10
Wailea 2BR Villa Near Beach, Shops & GolfFrom $325/night · Sleeps 6
Wailea, Oceanfront, Polo Beach Club Condo #403From $830/night · Sleeps 5
Ocean View, Steps away from the poolFrom $491/night · Sleeps 4
Summer Deal Wailea Villa with Ocean Views and Private LanaisFrom $1,638/night · Sleeps 8
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!From $216/night · Sleeps 4
Fantastic unit! 10/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4From $479/night · Sleeps 4
Stunningly Renovated! Ocean View! Elua 2305From $810/night · Sleeps 4
Luxury at its Best with Big Ocean Views!!From $450/night · Sleeps 4
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2BaFrom $508/night · Sleeps 4
Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!From $275/night · Sleeps 4
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ GrillFrom $858/night · Sleeps 6
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third TierFrom $1,049/night · Sleeps 8
Full Ocean View WaileaFrom $604/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 #2301From $806/night · Sleeps 6
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion VillasFrom $519/night · Sleeps 6
From $738/night
Walk to Beach, Ocean Views, Relax by the Pool
Wailea, Hawaii
★★★★★ 10.0/10 · 173 reviews
- 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 $235/night
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
Wailea, Hawaii
★★★★★ 10.0/10 · 164 reviews
Believe the 150+ 5-star Reviews! Amazing Bargain right now due to lower Maui travel this season. Fewer island visitors this year means our nightly...
From $1,620/night
The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
Wailea, Hawaii
★★★★★ 10.0/10 · 162 reviews
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 $470/night
NEW KITCHEN REMODEL! Amazing View!
Wailea, Hawaii
★★★★★ 10.0/10 · 161 reviews
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 $332/night
125+ 5star REVIEWS SAYS IT ALL! Golf & Ocean! LAST MIN CANCL APRIL! 169 +tx rate
Wailea, Hawaii
★★★★★ 10.0/10 · 155 reviews
Location: Grand Champions, Wailea, South Maui, Maui, Hawaii, USA (2 miles Kihei, 13 miles airport, 1/2 mile beach.) Accommodations: Condominium, 1...
From $369/night
Wailea Ekahi 40A - Your South Maui Oasis
Wailea, Hawaii
★★★★★ 10.0/10 · 149 reviews
*Please note-The main pool remodel will be complete on October 15. While the main pool is closed, three other pools will be available-please ask...
From $359/night
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
Wailea, Hawaii
★★★★★ 10.0/10 · 140 reviews
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 $1,436/night
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
Wailea, Hawaii
★★★★★ 10.0/10 · 140 reviews
4 Full Bedrooms & 3 Full Baths; Total 3892 S.F Beachfront Wailea: Ocean Panoramic & Outer Island Views, Penthouse K-208IMPORTANT: Maximum 8 Adult...
From $1,757/night
Wailea Beach Villas Penthouse K107 – Maui Luxury with Island Serenity
Wailea, Hawaii
★★★★★ 10.0/10 · 140 reviews
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 $635/night
14D Panoramic ocean view, beautiful sunset every night. Best in Ekahi!
Wailea, Hawaii
★★★★★ 10.0/10 · 131 reviews
Wailea Ekahi #14D is an Ocean View condominium in Wailea Ekahi's acclaimed Lower Village. There are amazing panoramic ocean views from this...
From $336/night
COMPLETE REMODEL! BRAND NEW EVERYTHING!!! AC and POOL!
Wailea, Hawaii
★★★★★ 10.0/10 · 130 reviews
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 $375/night
Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
Wailea, Hawaii
★★★★★ 10.0/10 · 130 reviews
Luxurious Tropical Retreat - Unit 31D is truly "one-of-kind"!Ideally located overlooking the lower Ekahi Village, Unit 31D provides our guests with...
From $425/night
Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village
Wailea, Hawaii
★★★★★ 10.0/10 · 124 reviews
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 $2,095/night
Stunning Ocean View Wailea Beach Villa- Book & Save
Wailea, Hawaii
★★★★★ 10.0/10 · 115 reviews
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 $689/night
No stairs inside or out! Beautifully remodeled Palms at Wailea 503
Wailea, Hawaii
★★★★★ 10.0/10 · 113 reviews
A rare Palms at Wailea find: a beautifully remodeled ground-floor ocean-view condo with no stairs inside or out and one of the largest private lanais...
From $594/night
Luxury Wailea Family Condo. Complete Remodel! AC and Pool.
Wailea, Hawaii
★★★★★ 10.0/10 · 111 reviews
Your Perfect Maui Family Retreat AwaitsExperience the ultimate in modern luxury at this completely renovated condo in Wailea. Just a 10-minute stroll...
From $1,336/night
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
Wailea, Hawaii
★★★★★ 10.0/10 · 97 reviews
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 $325/night
Wailea 2BR Villa Near Beach, Shops & Golf
Wailea, Hawaii
★★★★★ 10.0/10 · 95 reviews
Welcome to our spacious, beautifully remodeled Wailea villa. This immaculate two-bedroom, two-bath retreat offers quiet split-system air conditioning...
From $830/night
Wailea, Oceanfront, Polo Beach Club Condo #403
Wailea, Hawaii
★★★★★ 10.0/10 · 94 reviews
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 $491/night
Ocean View, Steps away from the pool
Wailea, Hawaii
★★★★★ 10.0/10 · 88 reviews
IMPORTANT NOTICE: Pavilion Pool Deck resurfacing Project - August 10 to October 16, 2026.The pavilion facilities WILL be available, including...
From $1,638/night
Summer Deal Wailea Villa with Ocean Views and Private Lanais
Wailea, Hawaii
★★★★★ 10.0/10 · 78 reviews
This property is hotel zoned, and not being affected by the recent proposed legislation.Located in highly desirable secluded area of neighborhood...
From $216/night
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Wailea, Hawaii
★★★★★ 10.0/10 · 73 reviews
Enjoy the exclusive Wailea lifestyle in this fashionably decorated, high-end suite with incredible ocean views!!!---This gorgeous, bright and...
From $479/night
Fantastic unit! 10/10! Hear the waves from the lanai! 1 bedroom unit. Sleeps 4
wailea, Hawaii
★★★★★ 10.0/10 · 73 reviews
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 $810/night
Stunningly Renovated! Ocean View! Elua 2305
Wailea, Hawaii
★★★★★ 10.0/10 · 69 reviews
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 $450/night
Luxury at its Best with Big Ocean Views!!
Wailea, Hawaii
★★★★★ 10.0/10 · 67 reviews
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 $508/night
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
Wailea, Hawaii
★★★★★ 10.0/10 · 66 reviews
5th night free! Each 5th night free! Promotion while the main pavilion is being resurfaced (October 15th). If this vacation home is available, you'll...
From $275/night
Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!
Wailea, Hawaii
★★★★★ 10.0/10 · 65 reviews
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 $858/night
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
Wailea, Hawaii
★★★★★ 10.0/10 · 64 reviews
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 $1,049/night
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier
Wailea, Hawaii
★★★★★ 10.0/10 · 63 reviews
Located on the third tier on the south side of the Ho’olei Resort on Maui, our two-level villa has jaw-dropping Pacific Ocean views and is perfectly...
From $604/night
Full Ocean View Wailea
Wailea, Hawaii
★★★★★ 10.0/10 · 60 reviews
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
Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern
Wailea, Hawaii
★★★★★ 10.0/10 · 57 reviews
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 $806/night
Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium #2301
Wailea, Hawaii
★★★★★ 10.0/10 · 55 reviews
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 $519/night
Impressive 2 Bdrm+2 Ba Paradise Condominium at Wailea Grand Champion Villas
Wailea, Hawaii
★★★★★ 10.0/10 · 53 reviews
Treat yourself to an impeccable Front-Row 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is the finest that...