Palms at Wailea Garden Deluxe Villas 2 BD 2 BAFrom $451/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
Palms at Wailea Garden Deluxe Villas 2 BD 2 BAFrom $451/night · Sleeps 6
Steps to Keawakapu Beach — Renovated Wailea Condo w/ PoolFrom $451/night · Sleeps 4
Palms at Wailea Garden Villas 2 Bedroom 2 BathFrom $452/night · Sleeps 6
Palms at Wailea Villa 805 Garden View 2 BD 2 BAFrom $452/night · Sleeps 6
Fall $250 Wailea Luxury Escape.Ocean & Haleakala Views.1 Bed/ 2 Bath.Huge Lanai!From $520/night · Sleeps 4
Palms at Wailea Ocean View Villas 2 Bedroom 2 BathFrom $543/night · Sleeps 6
Wailea Ekahi Village 3A - Townhome Near Keawakapu BeachFrom $566/night · Sleeps 4
Grand Champions | Ocean View 3 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-1499 by KBMFrom $595/night · Sleeps 10
Grand Champions | Ocean View 3 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-1481 by KBMFrom $629/night · Sleeps 10
Wailea Elua Village 104 | Ocean Views, 2 Baths & Steps to Ulua BeachFrom $735/night · Sleeps 4
Wailea Elua Village 1510 | 2 King Beds, Ocean View, 2 Min to Ulua BeachFrom $764/night · Sleeps 4
Wailea Elua Village 2102 | Renovated Ocean View, 2 Min to Ulua BeachFrom $854/night · Sleeps 5
Grand Champions | Ocean View 4 BR, Sleeps 14 | Car Incl. w/ 6+ Nights | GCH ML-1496 by KBMFrom $888/night · Sleeps 14
Wailea Elua Village 1202 | Ocean View Condo, 1-Min Walk to Ulua Beach and PoolsFrom $889/night · Sleeps 4
Makena Surf B305 Beachfront ResortFrom $917/night · Sleeps 4
Elevated 4th Floor Ocean ViewsFrom $1,133/night · Sleeps 8
Wailea Elua Village 307 | Wrap-Around Lanai, Seclusion & Steps to Ulua BeachFrom $1,181/night · Sleeps 6
Wailea Elua Village 707 | Ocean View, Private BBQ, 2 Min to Ulua BeachFrom $1,242/night · Sleeps 6
Wailea Elua Village 1603From $1,291/night · Sleeps 6
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview CondominiumFrom $1,386/night · Sleeps 6
Grand Champions | Ocean View 4 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-3777 by KBMFrom $1,424/night · Sleeps 10
Grand Champions | Ocean View 4 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-3780 by KBMFrom $1,424/night · Sleeps 10
Recently Renovated - Tropical Two Bedroom CondoFrom $1,488/night · Sleeps 6
Wailea Elua Village 1504 | Panoramic Ocean Views, Remodeled, 2 Min to BeachFrom $1,512/night · Sleeps 4
Grand Champions | Ocean View 5 BR, Sleeps 14 | Car Incl. w/ 6+ Nights | GCH ML-3786 by KBMFrom $1,864/night · Sleeps 14
Recently Renovated - Wailea Beach Villas ExcellenceFrom $1,885/night · Sleeps 6
Grand Champions | Ocean View 6 BR, Sleeps 16 | Car Incl. w/ 6+ Nights | GCH ML-3785 by KBMFrom $2,056/night · Sleeps 16
Wailea, Grand Champions Villas, Spacious 6 BR, Ocean View, Sleeps 16From $2,367/night · Sleeps 16
Redecorated! NEW Offering Summer 2025 - the Palm Coast F202 Ocean View Grand Luxe Villa Sleeps 8!From $2,895/night · Sleeps 8
Grand Champions | Ocean View 7 BR, Sleeps 20 | Car Incl. w/ 6+ Nights | GCH ML-3789 by KBMFrom $2,947/night · Sleeps 20
Wailea Beach Villas PH508 | Pools | Hot TubsFrom $3,007/night · Sleeps 8
Wailea Beach | Oceanfront 6 BR, Sleeps 12 | Car Incl. w/ 6+ Nights | WBV ML-3485 by KBMFrom $3,216/night · Sleeps 12
Auntie Kali's Cottage: 2 BR Wailea Home with Pool & Tiki BarFrom $810/night · Sleeps 4
From $451/night
Palms at Wailea Garden Deluxe Villas 2 BD 2 BA
Wailea, Hawaii
Deluxe garden-view villas offer a tranquil retreat surrounded by lush tropical landscaping in Wailea’s resort community. With a full kitchen,...
From $451/night
Steps to Keawakapu Beach — Renovated Wailea Condo w/ Pool
Wailea, Hawaii
Steps from Keawakapu Beach in the heart of Wailea, this fully renovated 1-bedroom, 2-bath condo sleeps up to 4 and puts you close to the sand, the...
From $452/night
Palms at Wailea Garden Villas 2 Bedroom 2 Bath
Wailea, Hawaii
Relax in a spacious two-bedroom villa with peaceful garden views, located in the prestigious Wailea resort community. Featuring a full kitchen, open...
From $452/night
Palms at Wailea Villa 805 Garden View 2 BD 2 BA
Wailea, Hawaii
Enjoy a peaceful stay in this two-bedroom garden-view villa nestled within the Wailea resort community’s lush surroundings. With a full kitchen,...
From $520/night
Fall $250 Wailea Luxury Escape.Ocean & Haleakala Views.1 Bed/ 2 Bath.Huge Lanai!
Wailea, Hawaii
Welcome to your own piece of paradise at Wailea Ekahi Village, one of Maui’s most beautiful and sought-after beachfront communities! Our spacious one...
From $543/night
Palms at Wailea Ocean View Villas 2 Bedroom 2 Bath
Wailea, Hawaii
Take in breathtaking ocean views from a spacious two-bedroom villa in Wailea’s resort community. Featuring a full kitchen, open living area, and...
From $566/night
Wailea Ekahi Village 3A - Townhome Near Keawakapu Beach
WAILEA, Hawaii
Wailea Ekahi Village 3A. Spacious 2BR/3BA Townhome Near Keawakapu BeachWelcome to Wailea Ekahi Village 3A, a spacious two-bedroom, three-bath...
From $595/night
Grand Champions | Ocean View 3 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-1499 by KBM
Wailea, Hawaii
** 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 $629/night
Grand Champions | Ocean View 3 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-1481 by KBM
Wailea, Hawaii
** 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 $735/night
Wailea Elua Village 104 | Ocean Views, 2 Baths & Steps to Ulua Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 104 Elua Village sits steps from Ulua Beach and connects directly to the 3.2-mile...
From $764/night
Wailea Elua Village 1510 | 2 King Beds, Ocean View, 2 Min to Ulua Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1510Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $854/night
Wailea Elua Village 2102 | Renovated Ocean View, 2 Min to Ulua Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 2102Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $888/night
Grand Champions | Ocean View 4 BR, Sleeps 14 | Car Incl. w/ 6+ Nights | GCH ML-1496 by KBM
Wailea, Hawaii
** 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 $889/night
Wailea Elua Village 1202 | Ocean View Condo, 1-Min Walk to Ulua Beach and Pools
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1202Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $917/night
Makena Surf B305 Beachfront Resort
Wailea, Hawaii
Welcome to Makena Surf B305, an extraordinary oceanfront retreat offering some of the most breathtaking views on all of Maui. Perfectly positioned...
From $1,133/night
Elevated 4th Floor Ocean Views
Wailea, Hawaii
Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square...
From $1,181/night
Wailea Elua Village 307 | Wrap-Around Lanai, Seclusion & Steps to Ulua Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 307At 1,336 square feet, 307 is the largest unit in the Elua — a remodeled 2-bedroom...
From $1,242/night
Wailea Elua Village 707 | Ocean View, Private BBQ, 2 Min to Ulua Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 707Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $1,291/night
Wailea Elua Village 1603
Wailea, Hawaii
Welcome to the serene and luxurious Wailea Elua Village 1603, a stunning 2-bedroom ocean front condo nestled in the heart of Maui’s resort town of...
From $1,386/night
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Wailea, Hawaii
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea...
From $1,424/night
Grand Champions | Ocean View 4 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-3777 by KBM
Wailea, Hawaii
** 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 $1,424/night
Grand Champions | Ocean View 4 BR, Sleeps 10 | Car Incl. w/ 6+ Nights | GCH ML-3780 by KBM
Wailea, Hawaii
** 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 $1,488/night
Recently Renovated - Tropical Two Bedroom Condo
Wailea, Hawaii
Wailea Elua Village offers tropical vacation condos set amid Wailea’s resort hotels, making it a perfect luxury destination. Enjoy easy access from...
From $1,512/night
Wailea Elua Village 1504 | Panoramic Ocean Views, Remodeled, 2 Min to Beach
Wailea, Hawaii
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1504Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea...
From $1,864/night
Grand Champions | Ocean View 5 BR, Sleeps 14 | Car Incl. w/ 6+ Nights | GCH ML-3786 by KBM
Wailea, Hawaii
** 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 $1,885/night
Recently Renovated - Wailea Beach Villas Excellence
Wailea, Hawaii
Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfront communities. This...
From $2,056/night
Grand Champions | Ocean View 6 BR, Sleeps 16 | Car Incl. w/ 6+ Nights | GCH ML-3785 by KBM
Wailea, Hawaii
** 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 $2,367/night
Wailea, Grand Champions Villas, Spacious 6 BR, Ocean View, Sleeps 16
Wailea, Hawaii
Summary:Six bedrooms, ocean views, and room for 16 at Grand Champions Villas in Wailea - this stay pairs Unit A and Unit B, two 3-bedroom...
From $2,895/night
Redecorated! NEW Offering Summer 2025 - the Palm Coast F202 Ocean View Grand Luxe Villa Sleeps 8!
Wailea, Hawaii
Brand New Offering! Our brilliantly refreshed and extensively redecorated The Palm Coast Villa F202 at Wailea Beach Villas that includes beautiful...
From $2,947/night
Grand Champions | Ocean View 7 BR, Sleeps 20 | Car Incl. w/ 6+ Nights | GCH ML-3789 by KBM
Wailea, Hawaii
** 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 $3,007/night
Wailea Beach Villas PH508 | Pools | Hot Tubs
Wailea, Hawaii
Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique...
From $3,216/night
Wailea Beach | Oceanfront 6 BR, Sleeps 12 | Car Incl. w/ 6+ Nights | WBV ML-3485 by KBM
Wailea, Hawaii
** 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 $810/night
Auntie Kali's Cottage: 2 BR Wailea Home with Pool & Tiki Bar
Kihei, Hawaii
★★★★★ 10.0/10 · 209 reviews
Auntie Kali's Cottage is a 2-bedroom Hawaiian plantation-style retreat on Maui's south shore, offering a private pool lagoon, tiki bar, hot tub, and...