Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BAFrom $1,199/night · Sleeps 8
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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Find Wailea Rentals by Condo or Resort
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Wailea Vacation Rentals Listings
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Wailea Vacation Rentals Map
Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BAFrom $1,199/night · Sleeps 8
~ This Is Wailea Living ~From $400/night · Sleeps 4
Removed Trees=stunning ocean sunsets,@Wailea Beaches, Green, and Foodie Kitchen!From $275/night · Sleeps 4
1BR/2BA Maui Kamaole/Wailea Border. K Cluster @ Tropical Pool!From $259/night · Sleeps 4
Luxe Oceanview Hideaway on Wailea Old Blue Golf CourseFrom $275/night · Sleeps 2
Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split ACFrom $454/night · Sleeps 2
Picturesque Ocean View Condo - Last Minute Deal! Beautiful Wailea at Elua 2002From $900/night · Sleeps 6
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk EverywhereFrom $2,004/night · Sleeps 8
Wailea Grand Champion Villas 3-Bedroom updated Home centrally located in WaileaFrom $470/night · Sleeps 7
NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BAFrom $515/night · Sleeps 6
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on MauiFrom $719/night · Sleeps 6
Maui Wailea Escape 2 Bedroom, 2.5 Bath Condo #23A - View, Pools, Walk to BeachFrom $1,036/night · Sleeps 5
Wailea Ekahi 1B Recently Remodeled Ocean View 1st Floor Luxury 1BD 2BA CondoFrom $575/night · Sleeps 4
1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally OwnedFrom $401/night · Sleeps 4
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC!From $518/night · Sleeps 4
Newly remodeled corner unit w/ large patio -Wailea Treasure awaits you!From $420/night · Sleeps 4
Wailea Ekahi 54A: Panoramic Ocean View. Paint & Refresh August 2026!From $563/night · Sleeps 6
Tropical Wailea RetreatFrom $279/night · Sleeps 2
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to BeachFrom $595/night · Sleeps 4
Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shopsFrom $1,400/night · Sleeps 8
Direct Ocean Front Property Wailea Ekahi 16A 2 Bed 2 Full Bath Ocean Views 5starFrom $890/night · Sleeps 6
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea BeachFrom $1,520/night · Sleeps 12
There is NO PLACE like Wailea in a two-storey townhouse! Last Minute Deal!From $405/night · Sleeps 6
Wailea Ekolu 1207 2 Bedroom 2 Bath CondoFrom $348/night · Sleeps 4
Wailea Ekahi 33c Ocean View Condo - 500 Feet from the Beach!From $310/night · Sleeps 4
Gorgeous Wailea Elua 1 Bd+2Ba Executive Vacation Condominium - #2011From $536/night · Sleeps 4
Luxury Wailea Villa l Stunning Remodel l Couples Retreat l Only 5 Star ReviewsFrom $362/night · Sleeps 2
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, MauiFrom $1,350/night · Sleeps 5
On Wailea Blue Golf Course ⛳️with Ocean View. 🌊From $585/night · Sleeps 6
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!From $450/night · Sleeps 4
Luxury Villa Steps from Wailea Beach with Resort Amenities & Stunning UpgradesFrom $1,432/night · Sleeps 8
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu BeachFrom $440/night · Sleeps 2
Maui Family Owned & Managed - Wailea Grand Champions VillaFrom $504/night · Sleeps 6
From $1,199/night
Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BA
Kihei, Hawaii
★★★★★ 10.0/10 · 185 reviews
Wailea Beach Villas voted as one of the top 100 USA Hotels by the Conde Nast Traveler Readers Choice Awards!Luxury awaits in this exquisite three...
From $400/night
~ This Is Wailea Living ~
Kihei, Hawaii
★★★★★ 10.0/10 · 154 reviews
This is Wailea Living!Nestled in a private and secluded enclave between the Wailea Blue Course and the Wailea Tennis Club, the Wailea Grand Champions...
From $275/night
Removed Trees=stunning ocean sunsets,@Wailea Beaches, Green, and Foodie Kitchen!
Kihei, Hawaii
★★★★★ 10.0/10 · 140 reviews
To enjoy our GORGEOUS OCEAN VIEW, from our upscale, VERY GREEN, very sound proof, 2 Bedroom, 1 and 1/2 Bath Condo, just a 4 minute walk to the nicest...
From $259/night
1BR/2BA Maui Kamaole/Wailea Border. K Cluster @ Tropical Pool!
Kihei, Hawaii
★★★★★ 10.0/10 · 138 reviews
Personal Touch:We stock everything you need: dish soap, laundry soap, paper towels, napkins, Kleenex, TP, garbage bags, coffee filters etc... All you...
From $275/night
Luxe Oceanview Hideaway on Wailea Old Blue Golf Course
Kihei,, Hawaii
★★★★★ 10.0/10 · 135 reviews
WAILEA PARADISE HIDEAWAYEscape to a serene and elegant retreat in the heart of Wailea.Set on the renowned Wailea Old Blue Golf Course, this...
From $454/night
Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC
Kihei, Hawaii
★★★★★ 10.0/10 · 129 reviews
Experience the essence of Maui at Wailea Ekolu 407, a luxurious 1-bedroom, 2-bathroom condo that offers breathtaking panoramic ocean views from the...
From $900/night
Picturesque Ocean View Condo - Last Minute Deal! Beautiful Wailea at Elua 2002
Kihei, Hawaii
★★★★★ 10.0/10 · 117 reviews
Wailea Elua #2002 Ocean View CondoThis newly remodeled in 2021 second floor 2 bedroom and 2 bathroom condo has an open floor plan, large lanai that...
From $2,004/night
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Kihei, Hawaii
★★★★★ 10.0/10 · 109 reviews
The best location in Wailea! Quick 2-minute walk to Wailea beach, shops, restaurants & the stunningly scenic Wailea Beach Path. BOOKING...
From $470/night
Wailea Grand Champion Villas 3-Bedroom updated Home centrally located in Wailea
Kihei, Hawaii
★★★★★ 10.0/10 · 105 reviews
Aloha, our home is located in the center of Wailea on the first hole of the Wailea Blue Course and I is perfect for families or couples. The 3...
From $515/night
NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 105 reviews
Aloha! We are back on the rental market after a lengthy remodel! Enjoy beautiful ocean views while relaxing in our very spacious 2 story, 2...
From $719/night
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Kihei, Hawaii
★★★★★ 10.0/10 · 105 reviews
Stay just minutes from Maui’s most beautiful beaches in this newly remodeled 3-bedroom, 2-bath private home in Wailea/Kihei. Ideally located near...
From $1,036/night
Maui Wailea Escape 2 Bedroom, 2.5 Bath Condo #23A - View, Pools, Walk to Beach
Kihei, Hawaii
★★★★★ 10.0/10 · 104 reviews
Sun, fun and the Hawaiian Island lifestyle is waiting for you! Our townhouse is located in the beautiful beach front property of Ekahi Village....
From $575/night
Wailea Ekahi 1B Recently Remodeled Ocean View 1st Floor Luxury 1BD 2BA Condo
Kihei, Hawaii
★★★★★ 10.0/10 · 102 reviews
Unit 1B is located on beautiful Keawakapu Beach in gorgeous Wailea. This totally remodeled lower village, ground floor unit has one large lanai with...
From $401/night
1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned
Kihei, Hawaii
★★★★★ 10.0/10 · 101 reviews
Retreat and relax in this comfortable, serene, light and airy, completely remodeled unit. This ground floor unit in the quiet, beachfront Wailea...
From $518/night
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC!
Kihei, Hawaii
★★★★★ 10.0/10 · 98 reviews
* * * * The Wailea Ekahi main pool area will be closed for renovations from August 10, 2026 to October 15, 2026. The 3 other pools on property will...
From $420/night
Newly remodeled corner unit w/ large patio -Wailea Treasure awaits you!
Kihei, Hawaii
★★★★★ 10.0/10 · 93 reviews
In sunny Wailea, a short stroll to some of south Maui's most incredible sand beaches, you will find our WAILEA TREASURE! Close proximity to all of...
From $563/night
Wailea Ekahi 54A: Panoramic Ocean View. Paint & Refresh August 2026!
Kihei, Hawaii
★★★★★ 10.0/10 · 93 reviews
Our Family has Two - Two Bedroom/Two Bathroom Units above and Below Each other in Ekahi Village. This is great for Families or large groups traveling...
From $279/night
Tropical Wailea Retreat
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 92 reviews
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space...
From $595/night
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 87 reviews
"Comfortable luxury with a magnificent view," wrote a recent guest. Wailea Ekahi 14F is an upper-floor 2-bedroom 2-bath condo. Situated in a quiet...
From $1,400/night
Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops
Wailea-Makena, Hawaii
★★★★★ 10.0/10 · 87 reviews
Dramatic ocean views, this spacious town home is approximately 2500 sq ft of interior footage and 596 sq ft of lanai space. The Hoolei community is...
From $890/night
Direct Ocean Front Property Wailea Ekahi 16A 2 Bed 2 Full Bath Ocean Views 5star
Kihei, Hawaii
★★★★★ 10.0/10 · 85 reviews
Wailea Ekahi Villas Unit 16A: A ocean view 2 bedroom 2 full bathroom unit with a layout designed specifically for couples or young families with...
From $1,520/night
4-bedroom mini-splits AC vacation home just 5 minutes drive to Wailea Beach
Kihei, Hawaii
★★★★★ 10.0/10 · 81 reviews
Discover the breathtaking Wailea area in Kihei and indulge in top-notch tropical life at this lavish four-bedroom holiday house. Nestled just minutes...
From $405/night
There is NO PLACE like Wailea in a two-storey townhouse! Last Minute Deal!
Kihei, Hawaii
★★★★★ 10.0/10 · 78 reviews
WELCOME TO OUR HAWAIIAN RETREAT in Wailea!Enjoy your getaway at our home-away from home! We keep it in excellent condition - take a look at some of...
From $348/night
Wailea Ekolu 1207 2 Bedroom 2 Bath Condo
Kihei, Hawaii
★★★★★ 10.0/10 · 75 reviews
Relax at our quiet 2 bedroom /2 bath condo with stunning views overlooking the Wailea Blue golf course all the way to the ocean. Guests can enjoy...
From $310/night
Wailea Ekahi 33c Ocean View Condo - 500 Feet from the Beach!
Kihei, Hawaii
★★★★★ 10.0/10 · 72 reviews
Welcome to this Wailea Ekahi Condo (Unit 33C -LINKS TO OUR PERSONAL WEBSITE ARE LOCATED BELOW). Our one bedroom, one bath ocean view unit is located...
From $536/night
Gorgeous Wailea Elua 1 Bd+2Ba Executive Vacation Condominium - #2011
Kihei, Hawaii
★★★★★ 10.0/10 · 72 reviews
*** Please note there is construction work to the right of the property by the Andaz from August 18th to 25th that will be pretty noisy**2011 Wailea...
From $362/night
Luxury Wailea Villa l Stunning Remodel l Couples Retreat l Only 5 Star Reviews
Kihei, Hawaii
★★★★★ 10.0/10 · 71 reviews
Your Maui Escape Starts HereBeautifully remodeled, meticulously cleaned, exceptionally comfortable, and perfectly located in Wailea. Make yourself at...
From $1,350/night
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Kihei, Hawaii
★★★★★ 10.0/10 · 67 reviews
Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unobstructed ocean view...
From $585/night
On Wailea Blue Golf Course ⛳️with Ocean View. 🌊
Kihei, Hawaii
★★★★★ 10.0/10 · 64 reviews
Hawaii GE & TA Tax ID # G/T 006-824-3456-01 Taxes on total amount is 17.42%. Not included in the vrbo quote. Required is a signed rental agreement...
From $450/night
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all!
Kihei, Hawaii
★★★★★ 10.0/10 · 62 reviews
DIRECT TO ROOM CHECK-IN: At 1206 The Palms, you go directly to your private condo without ever needing to check in. The same is true upon check-out....
From $1,432/night
Luxury Villa Steps from Wailea Beach with Resort Amenities & Stunning Upgrades
Kihei, Hawaii
★★★★★ 10.0/10 · 61 reviews
This property is hotel zoned, and not being affected by the recent proposed legislation.Wailea Beach, voted one of the top beaches in the world, is a...
From $440/night
Wailea Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Kihei, Hawaii
★★★★★ 10.0/10 · 60 reviews
IMPORTANT — August 10 to October 16, 2026 Only: OCEANFRONT POOL IS CLOSED AND SIGNIFICANT NOISE AND CONSTRUCTION WILL OCCUR DURING THESE DATES. RATES...
From $504/night
Maui Family Owned & Managed - Wailea Grand Champions Villa
Kihei, Hawaii
★★★★★ 10.0/10 · 60 reviews
Located on the world-class Wailea Blue Golf Course. Our Wailea Grand Champions condo has been newly redecorated and furnished with decor that depicts...