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).
$627/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (182 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 (161 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.
$792/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQQ (sleeps 4)
5 (156 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.
$1384/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 3 - KTQT (sleeps 8)
5 (153 reviews)
Luxury 3-bedroom, 3-bath, 2500 sq. ft. Penthouse Villa J205 at Wailea Beach Villas with ocean views, gourmet kitchen, and resort amenities.
$409/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KQ (sleeps 4)
5 (150 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.
$460/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (144 reviews)
Ground floor, remodeled condo with ocean views in Ekahi Village. Short walk to the beach. Fully stocked kitchen, washer/dryer, beach amenities.
$488/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 5)
4.9 (193 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.
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (143 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.
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (141 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.
$471/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 2 - KF (sleeps 6)
4.9 (186 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.
$507/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (134 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.
$1203/nt (avg.)
Location: Hoolei, Wailea
Bedrooms: 3 - KKKX (sleeps 8)
5 (133 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.
$888/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQQ (sleeps 5)
5 (131 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.
$1263/nt (avg.)
Location: Hoolei, Wailea
Bedrooms: 3 - KQX (sleeps 10)
5 (129 reviews)
Luxurious 3 bed, 3.5 bath townhome at Hoolei Wailea Beach with private elevator, ocean views, BBQ area, entertainment system, and resort amenities.
$712/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KQQX (sleeps 8)
4.9 (173 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.
$1279/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KKTQX (sleeps 6)
5 (128 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.
$462/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (125 reviews)
Luxurious tropical retreat in Maui's Ekahi Village. Spectacular ocean and volcano views, privacy, short walk to Keawakapu Beach. Modern amenities.
Location: Grand Champions, Wailea
Bedrooms: 2 - KTX (sleeps 5)
5 (125 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.
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KK (sleeps 4)
4.9 (164 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.
$1348/nt (avg.)
Location: Wailea Beach Villas, Wailea
Bedrooms: 2 - KQX (sleeps 6)
5 (121 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.
$390/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (121 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.
$383/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - KXQ (sleeps 4)
4.9 (161 reviews)
Clean, open condo w/ ocean view & lanai in Wailea Ekolu. Close to beautiful beaches, golf courses, shopping, & dining. Perfect for a Maui retreat.
Location: Hoolei, Wailea
Bedrooms: 3 - KKQ (sleeps 8)
5 (119 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.
$587/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 3)
5 (119 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.
$454/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.
$760/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 2 - KQFT (sleeps 8)
4.9 (158 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.
Location: The Palms at Wailea, Wailea
Bedrooms: 2 - KTTXX (sleeps 6)
5 (116 reviews)
Luxurious, modern 2BR/2BA vacation rental at The Palms at Wailea. Recently renovated, with ocean views, a private lanai with BBQ, and family-friendly amenities. Free laundry, on-site concierge, and access to a hot tub and saltwater pool.
$709/nt (avg.)
Location: Wailea
Bedrooms: 3 - KKQ (sleeps 6)
5 (115 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.
$363/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (114 reviews)
Luxurious and affordable vacation rental in Wailea, Maui with stunning views, modern finishes, and access to 5 beaches, golf courses, and shopping.
$326/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (111 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.
$299/nt (avg.)
Location: Grand Champions, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (149 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.
$515/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - QQ (sleeps 5)
5 (109 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.
$347/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 4)
5 (109 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.
$370/nt (avg.)
Location: The Palms at Wailea, Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (145 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.
$593/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - KX (sleeps 3)
5 (107 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.
$383/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - TTQXK (sleeps 5)
5 (106 reviews)
Oceanfront, 2nd floor corner unit with stunning garden view. Recently remodeled kitchen, equipped with modern amenities, and state-of-the-art AC units.
Location: Grand Champions, Wailea
Bedrooms: 2 - KT (sleeps 4)
5 (106 reviews)
Private & secluded Wailea Grand Champions Villas offer a renovated 2-bedroom ground-floor unit with en-suites, A/C, and a private lanai. Enjoy golf, tennis, spa, and beaches. Fully stocked kitchen.
$414/nt (avg.)
Location: Ekahi Village, Wailea
Bedrooms: 1 - K (sleeps 2)
5 (105 reviews)
1BR/1BA upper level condo, newly furnished, air conditioned, with lanai, WiFi, parking, and ocean views. Close to beaches, trails, and shopping.
$565/nt (avg.)
Location: Wailea Ekolu, Wailea
Bedrooms: 2 - KK (sleeps 4)
5 (105 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.
Location: Grand Champions, Wailea
Bedrooms: 1 - (sleeps 4)
5 (105 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.
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