Wailea Ekahi Village 20H | Ocean Views, 4 Resort Pools, at Keawakapu BeachFrom $924/night · Sleeps 6
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
Wailea Ekahi Village 20H | Ocean Views, 4 Resort Pools, at Keawakapu BeachFrom $924/night · Sleeps 6
Prime Wailea Location! Split AC! Wailea Ekahi 36EFrom $183/night · Sleeps 4
Wailea Ekahi 52B | Resort Level Amenities!From $315/night · Sleeps 4
Grand Champions | Ocean View 1 BR | Car Incl. w/ 6+ Nights | GCH-121 by KBMFrom $172/night · Sleeps 4
Oceanfront Makena Surf G202 - Professionally ManagedFrom $1,025/night · Sleeps 6
Ocean Views of Molokini - Makena Surf F304From $1,151/night · Sleeps 6
Walk to the Beach in Seconds - Makena Surf E102From $1,672/night · Sleeps 4
3BD Wailea Villa - Great for FamiliesFrom $2,744/night · Sleeps 6
Walk to Locals Favorite Beach - Wailea Ekahi 40FFrom $339/night · Sleeps 4
Wailea Elua Village 401 | Ocean View, Pool, Wrap Lanai, 2 Min to Ulua BeachFrom $1,060/night · Sleeps 6
Wailea Grand Champions 116 - Professional ManagedFrom $217/night · Sleeps 4
Wailea Ekahi Village 44B – Remodeled Garden-View Studio by the Pool and BeachFrom $221/night · Sleeps 2
Wailea Elua Village 1511 | Ground Floor, Step-Free, 2 Min to Ulua BeachFrom $610/night · Sleeps 4
Ground Floor Bliss By The BeachFrom $631/night · Sleeps 6
Ocean Views in the Heart of Wailea | Elua Village 2005From $680/night · Sleeps 6
Wailea Elua Village 1501 | XL Lanai, 2 Min to Ulua Beach, 2 Pools & PickleballFrom $1,167/night · Sleeps 6
Wailea Elua Village 1502 | Ocean View, 2 Min to Ulua Beach, Pools & PickleballFrom $1,057/night · Sleeps 6
Wailea Ekahi 18C | Garden View Walkout Retreat,4 Resort Pools & Beach GearFrom $242/night · Sleeps 4
Wailea Ekolu Village 1404 | Ocean Views, Golf Clubs & Walkable to WaileaFrom $232/night · Sleeps 4
Makena Surf F207 Beachfront ResortFrom $1,377/night · Sleeps 6
Beachfront / Oceanfront Private Home Sleeps 8From $3,500/night · Sleeps 8
August Sale! Unwind in a Wailea Ocean-View Condo with Pool, Hot Tub & W/DFrom $403/night · Sleeps 4
*NEW* Fall Special Ground-Floor Wailea Oceanview Retreat Near the BeachFrom $218/night · Sleeps 4
NEW Fall Sale Ocean-View Wailea Townhouse with Two Shaded LanaisFrom $408/night · Sleeps 4
*New* Wailea Fairway Condo with Pool and Hot TubFrom $240/night · Sleeps 4
Chic Coastal Wailea 2BR Condo Lush Tropical Grounds Saltwater Pool BeachFrom $635/night · Sleeps 6
Wailea Beach Villas with Private Plunge Pool | 3 BR Sleeps 8 | Car Incl. w/ 6+ Nights | WBV-G101 by KBMFrom $1,361/night · Sleeps 8
Grand Champions | Ocean View 1 BR | Car Incl. w/ 6+ Nights | GCH-181 by KBMFrom $172/night · Sleeps 4
Platinum Rated and Professionally ManagedFrom $289/night · Sleeps 4
Premier Wailea Elua Village 1702- 2Bdr+2Bath Condominium-Steps to the Ocean!From $640/night · Sleeps 5
Snorkel Directly Out Front - Makena Surf C105From $793/night · Sleeps 6
Beachfront Wailea condo w/ 4 pools and direct beach accessFrom $222/night · Sleeps 7
Quiet Retreat Between Fairways - Grand Champions 140From $436/night · Sleeps 6
From $924/night
Wailea Ekahi Village 20H | Ocean Views, 4 Resort Pools, at Keawakapu Beach
Wailea, Hawaii
★★★★★ 8.6/10 · 14 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 20HThis spacious 1,505 sq.ft. second-floor condo, offers captivating ocean views over...
From $183/night
Prime Wailea Location! Split AC! Wailea Ekahi 36E
Wailea, Hawaii
★★★★★ 8.2/10 · 37 reviews
Wailea Ekahi 36B is a great ground floor location with lush garden views. This 1bedroom/2 bath condo offers the perfect Hawaiian retreat!Welcome to...
From $315/night
Wailea Ekahi 52B | Resort Level Amenities!
Wailea, Hawaii
★★★★★ 8.0/10 · 15 reviews
Welcome to Wailea Ekahi 52B, a studio vacation rental condo in Wailea, Maui, Hawaii that comfortably sleeps 4 guests with 1 bathroom, just steps from...
From $172/night
Grand Champions | Ocean View 1 BR | Car Incl. w/ 6+ Nights | GCH-121 by KBM
Wailea, Hawaii
★★★★★ 8.0/10 · 3 reviews
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $1,025/night
Oceanfront Makena Surf G202 - Professionally Managed
Wailea, Hawaii
★★★★★ 8.0/10 · 3 reviews
Makena Surf G202 is a charming oceanfront vacation residence located on the serene south side of this luxurious resort. Just a short stroll from the...
From $1,151/night
Ocean Views of Molokini - Makena Surf F304
Wailea, Hawaii
★★★★★ 8.0/10 · 3 reviews
Makena Surf F304 is a stunning oceanfront vacation rental located in the beautiful Makena region of Maui, Hawaii. This luxurious third-floor condo...
From $1,672/night
Walk to the Beach in Seconds - Makena Surf E102
Wailea, Hawaii
★★★★★ 8.0/10 · 3 reviews
Makena Surf E102 is a prime oceanfront vacation condo that offers a perfect blend of luxury and natural beauty. This 1,510 square foot residence is...
From $2,744/night
3BD Wailea Villa - Great for Families
Wailea, Hawaii
★★★★★ 8.0/10 · 3 reviews
Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant ocean view penthouse spans...
From $339/night
Walk to Locals Favorite Beach - Wailea Ekahi 40F
Wailea, Hawaii
★★★★★ 8.0/10 · 2 reviews
Discover the charm of Maui from the comfort of Wailea Ekahi 40F, a beautifully appointed one-bedroom, one-bathroom condo located in the desirable...
From $1,060/night
Wailea Elua Village 401 | Ocean View, Pool, Wrap Lanai, 2 Min to Ulua Beach
Wailea, Hawaii
★★★★★ 8.0/10 · 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 401Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $217/night
Wailea Grand Champions 116 - Professional Managed
Wailea, Hawaii
★★★★★ 8.0/10 · 1 reviews
Wailea Grand Champions 116 is a luxurious vacation rental located along the southern coast of Maui in the desirable tourist area of Wailea. This...
From $221/night
Wailea Ekahi Village 44B – Remodeled Garden-View Studio by the Pool and Beach
Wailea, Hawaii
★★★★★ 8.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 44BA recently remodeled 600 sq.ft. ground-floor studio, offering step-free access and...
From $610/night
Wailea Elua Village 1511 | Ground Floor, Step-Free, 2 Min to Ulua Beach
Wailea, Hawaii
★★★★★ 8.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1511Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $631/night
Ground Floor Bliss By The Beach
Wailea, Hawaii
★★★★★ 8.0/10 · 1 reviews
Makena Surf G105 is a prime oceanfront vacation condo that spans 1,510 sq. ft. and is situated on the ground floor. This inviting unit features two...
From $680/night
Ocean Views in the Heart of Wailea | Elua Village 2005
Wailea, Hawaii
★★★★★ 8.0/10 · 1 reviews
Wailea Elua Village 2005 is a stunning two-bedroom, two-bathroom vacation rental located in the desirable Wailea region of Maui. This beautifully...
From $1,167/night
Wailea Elua Village 1501 | XL Lanai, 2 Min to Ulua Beach, 2 Pools & Pickleball
Wailea, Hawaii
★★★★★ 8.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1501Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $1,057/night
Wailea Elua Village 1502 | Ocean View, 2 Min to Ulua Beach, Pools & Pickleball
Wailea, Hawaii
★★★★★ 7.0/10 · 2 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1502Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $242/night
Wailea Ekahi 18C | Garden View Walkout Retreat,4 Resort Pools & Beach Gear
Wailea, Hawaii
★★★★★ 6.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 18CA spacious 1,000 sq.ft. 1-bedroom condo with 2 full bathrooms, and step-free...
From $232/night
Wailea Ekolu Village 1404 | Ocean Views, Golf Clubs & Walkable to Wailea
Wailea, Hawaii
★★★★★ 4.0/10 · 1 reviews
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1404 Perched above Wailea on the second floor, this 1,069-square-foot condo opens up...
From $1,377/night
Makena Surf F207 Beachfront Resort
Wailea, Hawaii
★★★★★ 120 reviews
Welcome to the Makena Surf F207, where luxury meets the ocean's edge. This beautifully renovated 2-bedroom, 2-bathroom oceanfront condo is perfect...
From $3,500/night
Beachfront / Oceanfront Private Home Sleeps 8
Wailea, Hawaii
★★★★★ 117 reviews
ONLY DIRECTLY MANAGED listing site. This home defines the best of Maui with direct access to a sandy, swimming beach on one side and a lava rock...
From $403/night
August Sale! Unwind in a Wailea Ocean-View Condo with Pool, Hot Tub & W/D
Wailea, Hawaii
★★★★★ 30 reviews
Summary:Start the morning on your lanai with coffee, ocean blue on the horizon and golfers moving across the fairway below. This remodeled...
From $218/night
*NEW* Fall Special Ground-Floor Wailea Oceanview Retreat Near the Beach
Wailea, Hawaii
★★★★★ 22 reviews
Summary:Take your first Kona coffee to the private lanai and watch Wailea wake up beyond the ocean view. This ground-floor, two-bedroom condo sleeps...
From $408/night
NEW Fall Sale Ocean-View Wailea Townhouse with Two Shaded Lanais
Wailea, Hawaii
★★★★★ 19 reviews
Summary:Catch sunrise from one lanai, bring lunch outside on the other, and watch the colors change over the ocean at sunset. This airy, two-story...
From $240/night
*New* Wailea Fairway Condo with Pool and Hot Tub
Wailea, Hawaii
★★★★★ 16 reviews
Summary:Begin with tropical fruit on the balcony overlooking the fairway, then trade a quiet morning at home for a swim at Wailea Beach or a snorkel...
From $635/night
Chic Coastal Wailea 2BR Condo Lush Tropical Grounds Saltwater Pool Beach
Wailea, Hawaii
★★★★★ 9 reviews
** PLEASE NOTE: The Pool will be closed from September 15th - September 18th, 2026, for yearly maintenance. A brand-new split air-conditioning system...
From $1,361/night
Wailea Beach Villas with Private Plunge Pool | 3 BR Sleeps 8 | Car Incl. w/ 6+ Nights | WBV-G101 by KBM
Wailea, Hawaii
★★★★★ 9 reviews
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $172/night
Grand Champions | Ocean View 1 BR | Car Incl. w/ 6+ Nights | GCH-181 by KBM
Wailea, Hawaii
★★★★★ 3 reviews
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more...
From $289/night
Platinum Rated and Professionally Managed
Wailea, Hawaii
★★★★★ 3 reviews
Escape to paradise in this beautifully appointed one-bedroom vacation rental nestled in the lush tropical gardens of Wailea Ekahi Village. Located on...
From $640/night
Premier Wailea Elua Village 1702- 2Bdr+2Bath Condominium-Steps to the Ocean!
Wailea, Hawaii
★★★★★ 3 reviews
Don't wait. Treat yourself and reserve this holiday property for your vacation. Spoil yourself with a dreamy, beachfront 2 bedroom/2 bath Wailea Elua...
From $793/night
Snorkel Directly Out Front - Makena Surf C105
Wailea, Hawaii
★★★★★ 3 reviews
Enter the cool marbled foyer of Makena Surf C105, a luxurious 1,600 sq. ft. ocean view vacation rental on the first floor of the prestigious Makena...
From $222/night
Beachfront Wailea condo w/ 4 pools and direct beach access
Wailea, Hawaii
★★★★★ 2 reviews
Welcome to Tutu’s House! Step into 25B and be transported back to the days as a child visiting your favorite Auntie or Tutu’s (grandma) home....
From $436/night
Quiet Retreat Between Fairways - Grand Champions 140
Wailea, Hawaii
★★★★★ 2 reviews
Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charming property combines elegance...