Wailea Vacation Rentals

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Showing top 200 rentals. Use the Search Filters button to narrow down the choices based on your preferences (like oceanview units, pricing, and dates).
$350/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (178 reviews)
Luxurious custom remodeled condo in Palms at Wailea, Maui. Elegant decor, Brazilian teak wood floors, Italian travertine stone, and scenic views. Gourmet kitchen, Bose sound system, and flat-screen TVs. Not suitable for children/babies.
Location: Elua Village, Wailea
Bedrooms: 2 - KQT (sleeps 4)
5 (160 reviews)
Luxury 2-bed, 2-bath condo with ocean views, a large lanai, and top-to-bottom remodel. Gated community on Ulua Beach with pools, BBQs, and amenities.
$995/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 3 - KTQT (sleeps 8)
5 (151 reviews)
Luxury 3-bedroom, 3-bath, 2500 sq. ft. Penthouse Villa J205 at Wailea Beach Villas with ocean views, gourmet kitchen, and resort amenities.
$645/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQQ (sleeps 4)
5 (151 reviews)
Wailea Ekahi 34F: modern 2-bed condo in Wailea, Maui. 2 master suites, 2 private lanais with ocean views, renovated, beach toys/chairs, 4 pools, beach access.
$378/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KQ (sleeps 4)
5 (148 reviews)
Fully renovated condo with ocean/mountain/garden views, California king bed, A/C, new furnishings, travertine floors, and full kitchen. Access to pools, BBQs, and Wailea's beaches, shopping, and golf. Suitable for 4 adults or 2 adults and 2 children.
$356/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (143 reviews)
Ground floor, remodeled condo with ocean views in Ekahi Village. Short walk to the beach. Fully stocked kitchen, washer/dryer, beach amenities.
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (142 reviews)
Fully renovated top floor condo with ocean and fairway views, air conditioning, vaulted ceilings, and high-end furnishings. Located in Wailea, Maui, with access to golf and tennis facilities, two swimming pool areas, and a private parking space. Pet-free complex.
$449/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 5)
4.9 (185 reviews)
Newly renovated condo closest to the beach in Wailea, Maui. Fully stocked high-end kitchen, comfortable furniture, and ocean sounds. Sleeps 6 with 2 full baths. Beach gear provided.
$670/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQQ (sleeps 5)
5 (134 reviews)
Luxury 2BR condo in Wailea resort, Maui. Newly renovated, high-end design, ocean & pool views, near beach & pool. King & 2 queen beds, full kitchen, 4K TVs, beach amenities. Ideal for families & couples.
$368/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 2 - KF (sleeps 6)
4.9 (179 reviews)
Wailea Grand Champions #48: 2bd, 2ba penthouse w/ 180° ocean views, 2 suites, sleeps 6. 2 pools, sundecks, spa tubs, BBQ grills, near golf & tennis.
$950/nt (avg.)
Location: Hoolei, Wailea
Bedrooms: 3 - KKKX (sleeps 8)
5 (132 reviews)
Deluxe Ocean View villa in the top row 'A' building with unobstructed panoramic views of the ocean. Private elevator, gourmet kitchen, and outdoor BBQ. Nearby amenities include restaurants, golf courses, shopping, and white sand beaches.
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (129 reviews)
Luxury 1 bed, 2 bath top floor condo in Grand Champions Villas, Wailea. Overlooks the "serenity pool" with garden and peek-a-boo ocean views. Upgraded kitchen and bathrooms with high-end amenities. Access to Wailea Tennis Club and Wailea Blue Golf Course.
$345/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (127 reviews)
1-bedroom condo with 2 full baths in Ekahi Village, Maui. Second floor unit with ocean views, air conditioning, and updated amenities. Complex has 4 pools, beach access, and a new pavilion. BBQs available at the pavilion and other locations on the property.
$898/nt (avg.)
Location: Hoolei, Wailea
Bedrooms: 3 - KQX (sleeps 10)
5 (127 reviews)
Luxurious 3 bed, 3.5 bath townhome at Hoolei Wailea Beach with private elevator, ocean views, BBQ area, entertainment system, and resort amenities.
$1400/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KKTQX (sleeps 6)
5 (127 reviews)
The Maui Escape is a luxurious 2.5 bedroom, 2 bathroom villa with 2,200 sq ft of living space. It has views of the upper pool, a private lanai, and offers unique appointments such as custom wood shutters, granite and hard wood finishes, and honed marble floors.
$404/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQQX (sleeps 8)
4.9 (169 reviews)
Luxury condo in Wailea Ekolu with ocean, mountain & golf course views. Largest floor plan, split A/C system, 2 levels, 2 pools, beach supplies & more.
$406/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KXX (sleeps 4)
5 (124 reviews)
Fully renovated ground-floor one-bedroom/two-bath vacation condo in Wailea resort district on Maui's "sunny side." Short walk to beach and pool, with partial ocean views. Luxurious master bedroom, fully equipped kitchen, pull-out queen sleeper sofa, and entertainment system.
$375/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (123 reviews)
Luxurious tropical retreat in Maui's Ekahi Village. Spectacular ocean and volcano views, privacy, short walk to Keawakapu Beach. Modern amenities.
$408/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 2 - KTX (sleeps 5)
5 (120 reviews)
Gorgeous ocean & golf course view 1BR condo in Wailea, Maui. Sleeps 4, ground floor access, 2 master suites, beach chic decor, AC, pool, beach gear.
$1131/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KQX (sleeps 6)
5 (119 reviews)
Spacious 2 bed/2 bath villa with den as 3rd bedroom. Ocean and pool views. Elegant island style decor. Resort amenities including pools, gym, concierge.
$349/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KK (sleeps 4)
4.9 (160 reviews)
Newly renovated vacation rental with stunning artwork, new furnishings, and top-notch amenities, including a 65" TV and Bose surround sound system. Enjoy a king-size bed, split unit AC, and filtered water.
$435/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 3)
5 (118 reviews)
Renovated, spacious condo in prestigious Wailea resort district. Quiet, corner unit close to the beach and pool with private garden and ocean views. Luxurious master bedroom, fully equipped kitchen, and entertainment system. Includes beach amenities.
$436/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KTT (sleeps 4)
4.9 (158 reviews)
Spacious 2BR/2BA ground floor condo in Wailea Ekolu with ocean views. Fully equipped kitchen, 2 pools, beach gear, A/C, WiFi, and golf discounts.
$530/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQX (sleeps 6)
5 (117 reviews)
Stunning 2BR vacation rental in Wailea with breathtaking ocean views, central air conditioning, flat screen TV, DVD player, Wi-Fi, and more.
$349/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (116 reviews)
Ground floor, fully furnished unit with beautiful views of the lush green lawn. Located in Wailea Ekahi, directly on the beach with easy access. Amenities include a family pool, shaded pavilion, and keyless access. Accommodates up to 4 guests with a king bed and twin Murphy bed.
$370/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KXQ (sleeps 4)
4.9 (156 reviews)
Clean, open condo w/ ocean view & lanai in Wailea Ekolu. Close to beautiful beaches, golf courses, shopping, & dining. Perfect for a Maui retreat.
$947/nt (avg.)
Location: Polo Beach Club, Wailea
Bedrooms: 2 - KQX (sleeps 6)
5 (114 reviews)
Escape to paradise at Polo Beach Club in Wailea! This ground floor unit offers stunning ocean views, direct beach access, lush gardens, elegant furnishings, and proximity to shopping, dining, and golf.
Location: Hoolei, Wailea
Bedrooms: 3 - KKQ (sleeps 8)
5 (114 reviews)
Maui Breeze Retreat at Ho'olei is a luxurious 3 bedroom, 3.5 bath townhome with stunning Pacific Ocean views. Amenities include a swimming pool, hot tubs, sauna, fitness facility, private elevator, and gourmet kitchen.
$595/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQFT (sleeps 8)
4.9 (152 reviews)
Vacation rental condo in Wailea Ekahi Village, Maui. Ground floor unit with private tropical lawn area, 2 lanais, and patio. Sleeps 8, fully air-conditioned, with 3 pools, gym, BBQ grills, and beach access. Cleaning practices include non-toxic disinfectant and UV light wand.
$338/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (112 reviews)
Luxurious and affordable vacation rental in Wailea, Maui with stunning views, modern finishes, and access to 5 beaches, golf courses, and shopping.
$545/nt (avg.)
Location: Wailea
Bedrooms: 3 - KKQ (sleeps 6)
5 (111 reviews)
Private fully equipped home on 1 acre at cul-de-sac; stunning ocean views; pool, spa, and beach gear; indoor/outdoor kitchens; AC, WiFi, parking.
$395/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - QQ (sleeps 5)
5 (108 reviews)
Enjoy panoramic ocean views from this private 2-bed, 2-bath condo in Wailea Ekolu. Vaulted ceilings, 3 lanais, and resort amenities. Walk to beaches and restaurants.
$375/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (108 reviews)
1 bedroom, 2 bath condo in Wailea Ekahi, Maui with ocean views. Located on the front row, steps from Keawakapu Beach. Air-conditioned, remodeled with stone counters, large lanai, and vaulted ceilings. Ekahi Village has 4 pools, one oceanfront, and 35 acres of tropical gardens.
$225/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (145 reviews)
Ground floor, 1BR/1BA condo with reserved parking, tropical garden views, and easy access to pools, BBQs, golf, tennis, and shops at Wailea. Sleeps 4. . Noise from adjacent units possible.
$270/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (107 reviews)
Ocean view 1 bed/2 bath condo in upper Wailea Ekahi Village, sleeps 4 guests. Double lanai, outdoor dining, and chaise lounges. 4 pools, pickleball court, and BBQ stations. Fully stocked kitchen, washer/dryer, and outdoor equipment. 7 min walk to Keawakapu Beach.
$279/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (107 reviews)
Spacious 1BR, 2-bath luxury condo in Wailea with panoramic ocean views. Includes fully-equipped kitchen, mini-split AC, and close to top golf, tennis, shopping, dining. Sleeps 2, beach gear included.
$500/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 3)
5 (106 reviews)
1BR/2BA ocean view condo in Wailea Ekahi Village. Direct access to Keawakapu Beach. 4 pools, AC, newly remodeled kitchen, memory-foam king bed.
$337/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (141 reviews)
Luxury ground floor condo at The Palms at Wailea, Maui. Split AC units, updated, fully stocked kitchen, beach gear, Weber gas BBQ, and pool access.
Location: Grand Champions, Wailea
Bedrooms: 1 - (sleeps 4)
5 (104 reviews)
Luxurious ocean-view, golf-front villa on 2nd fairway of Old Wailea Blue golf course. Fully equipped kitchen, spacious living area, and lanai. Two pools, two whirlpool spas, and BBQ facilities. Adjacent to Wailea Tennis facilities. Short walk to world-famous Wailea beaches.
$470/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KK (sleeps 4)
5 (102 reviews)
Olu'olu is a newly remodeled, 2 bedroom, 2 bath condo in Wailea Ekolu. It has stunning views of the ocean and mountains, and is equipped with high-end amenities such as a Sonos Sound/TV entertainment system, a gourmet kitchen, and a 3 Zone, Split AC System.
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