« New Search
Only showing top 200 highest rated rentals. Use the Search Filters button to narrow down the choices and see more options.
Search results (200)
$688/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 1 - K (sleeps 2)
5 (207 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.
$815/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KQQ (sleeps 6)
5 (204 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.
$1529/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KTQT (sleeps 8)
5 (184 reviews)
Luxury 3-bedroom, 3-bath, 2500 sq. ft. Penthouse Villa J205 at Wailea Beach Villas with ocean views, gourmet kitchen, and resort amenities.
$1369/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KQX (sleeps 10)
5 (171 reviews)
Luxurious 3 bed, 3.5 bath townhome at Hoolei Wailea Beach with private elevator, ocean views, BBQ area, entertainment system, and resort amenities.
$680/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 5)
4.9 (229 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: The Palms at Wailea , Wailea
Bedrooms: 2 - KTTXX (sleeps 6)
5 (170 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.
Location: Elua Village , Wailea
Bedrooms: 2 - KQT (sleeps 4)
5 (164 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.
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (163 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.
$1348/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKTQX (sleeps 6)
5 (162 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.
$491/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (160 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.
$1256/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KKKX (sleeps 8)
5 (159 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.
$378/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 2 - KF (sleeps 6)
4.9 (213 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.
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 2)
5 (154 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: Hoolei , Wailea
Bedrooms: 3 - KKQ (sleeps 8)
5 (152 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.
Location: Grand Champions , Wailea
Bedrooms: 2 - KT (sleeps 4)
5 (150 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.
$462/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (149 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.
$1158/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KQQX (sleeps 8)
4.9 (201 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.
$886/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KQFT (sleeps 8)
4.9 (200 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: Grand Champions , Wailea
Bedrooms: 2 - KTX (sleeps 5)
5 (147 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.
$612/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 1 - KXQ (sleeps 4)
4.9 (192 reviews)
Clean, open condo w/ ocean view & lanai in Wailea Ekolu. Close to beautiful beaches, golf courses, shopping, & dining. Perfect for a Maui retreat.
$376/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 2)
5 (142 reviews)
Luxurious and affordable vacation rental in Wailea, Maui with stunning views, modern finishes, and access to 5 beaches, golf courses, and shopping.
$540/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (138 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.
Location: The Palms at Wailea , Wailea
Bedrooms: 1 - KK (sleeps 4)
4.9 (185 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.
$1946/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 4 - KKQK (sleeps 8)
5 (136 reviews)
Beachfront penthouse with panoramic ocean views, 4 bedrooms, 3 baths, complete 2017-2018 renovation, sleeps 8, direct elevator access, on-site amenities.
Location: Grand Champions , Wailea
Bedrooms: 1 - (sleeps 2)
5 (135 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.
$509/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (134 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.
$514/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KTT (sleeps 4)
4.9 (179 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.
$398/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - TTQXK (sleeps 5)
5 (131 reviews)
Oceanfront, 2nd floor corner unit with stunning garden view. Recently remodeled kitchen, equipped with modern amenities, and state-of-the-art AC units.
$848/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 2)
5 (131 reviews)
Ocean-view condo in Wailea Ekahi's Lower Village with panoramic views. Master suite with secluded lanai, A/C & king bed. Remodeled kitchen with granite counters & new appliances. Close to beach, main pool & pavilion. Whale watch from Dec-Apr.
$681/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 2)
5 (130 reviews)
Luxurious tropical retreat in Maui's Ekahi Village. Spectacular ocean and volcano views, privacy, short walk to Keawakapu Beach. Modern amenities.
$484/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 1 - K (sleeps 2)
5 (127 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.
$311/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (169 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.
$430/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (167 reviews)
Ground floor, remodeled condo with ocean views in Ekahi Village. Short walk to the beach. Fully stocked kitchen, washer/dryer, beach amenities.
$471/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (123 reviews)
Beautiful one-bedroom, two-bath ground floor condo with ocean views in Wailea Ekolu Village. Fully stocked kitchen, king-size bed, and updated finishes throughout. Amenities include free local and long-distance calls, secure high-speed internet, and in-room safe.
$816/nt (avg.)
Location: Elua Village , Wailea
Bedrooms: 2 - KT (sleeps 6)
5 (123 reviews)
Luxury 2-bedroom condo in Wailea with ocean views, renovated in 2018. Beachfront complex with private lanai, upscale furnishings, and amenities.
$678/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KTX (sleeps 6)
5 (120 reviews)
Fully remodeled 2BR/2BA Maui condo with sweeping ocean views. 4-minute walk to the beach. Beautifully landscaped grounds, ocean-side pool, and pavilion.
$1128/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 4 - KTQXKK (sleeps 9)
5 (114 reviews)
Luxury 4BR Maui condo with panoramic ocean views, gourmet kitchen, Baby Grand piano, 75" smart TV, fitness center, 2 pool/spas, and underground parking. Located between The Grand Wailea & The Shops at Wailea with excellent shopping and dining options.
$773/nt (avg.)
Location: Elua Village , Wailea
Bedrooms: 2 - XKX (sleeps 6)
5 (114 reviews)
Newly remodeled 2BR/2BA condo on 2nd floor with ocean view, large lanai, 2 pools, gym, and steps away from Ulua Beach. Walking distance to shops and restaurants.
$578/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - KQX (sleeps 6)
4.9 (153 reviews)
Spacious 2BR Polynesian-style condo at Palms at Wailea Resort on Maui's southern coast. Peek ocean views, vaulted ceilings, tropical decor, DVD players, and large laundry/utility room. Tranquil waterfall, whale-shaped pool, lush gardens, and BBQ grill.
$521/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - KT (sleeps 4)
5 (113 reviews)
Luxury condo at Palms at Wailea with ocean views, no stairs, fully air-conditioned, renovated bathrooms, personal safe, and fully equipped kitchen.
$334/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (112 reviews)
1BR/2BA condo in Wailea Resort, S. Maui. By Ol' Blue Golf Course & top-rated Tennis Center. Boasts 2 pools, 2 Jacuzzis, 4 BBQs, sunset views. Near shopping, dining, beaches. Beach gear included.
$710/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - QKX (sleeps 7)
5 (109 reviews)
Newly remodeled Wailea Ekahi Unit 39C, a ground floor condo with ocean views, 2 master suites, beach toys, entertainment system, and beach access.
$398/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KQTTX (sleeps 5)
4.9 (146 reviews)
Oceanfront one-bedroom, two-bath ground-floor unit in a quiet Hawaii complex with beautiful garden view, equipped kitchen, A/C, HDTV/DVD, free Wi-Fi. Family-friendly and well-stocked. Premier unit with great reviews.
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KTT (sleeps 8)
5 (107 reviews)
Luxury 3BR/3BA penthouse in Wailea with a large lanai, BBQ, gourmet kitchen, and access to pools, beach, fitness center, and concierge service.
Location: The Palms at Wailea , Wailea
Bedrooms: 3 - XKX (sleeps 6)
5 (107 reviews)
Luxurious, modern, family-friendly 2BR/2BA vacation rental in Wailea with fully-stocked kitchen, new linens, beach gear, and ocean views from lanai.
$1050/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KQ (sleeps 6)
5 (106 reviews)
Luxurious 2 bedroom, ocean view condo with AC, 3 flat panel TVs, fast internet, Sonos speaker, and multiple lanais. Close to beach, shops, and restaurants. Resort amenities include 4 pools, paddle tennis, and shuffleboard. Parking, wifi, and cable included.
$494/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (105 reviews)
Condo, 1 Bedroom + Convertible bed(s), 2 Full Baths, (Sleeps 2-4)
$781/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KQ (sleeps 6)
5 (105 reviews)
Spacious 2-story, 2BR/2.5BA end unit condo/townhouse with ocean views, 2 separate entrances, 2 pools, and beach gear. Fully renovated with new appliances, AC units, and beach chic decor. Located in Wailea Ekolu Village, close to beaches, golf, tennis, and shopping.
$469/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 2)
4.9 (141 reviews)
1BR/1BA upper level condo, newly furnished, air conditioned, with lanai, WiFi, parking, and ocean views. Close to beaches, trails, and shopping.
$1058/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KT (sleeps 5)
5 (104 reviews)
Experience the Hawaiian Island lifestyle at Ekahi Village. Premier two-bedroom townhouse with ocean views, four pools, tennis courts and beach access.
$691/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (101 reviews)
Totally remodeled lower village, ground floor unit with ocean view, 4 pools, easy access to Wailea walk, A/C bedroom and living room, fully equipped kitchen, beach gear.
$602/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 3 - (sleeps 7)
5 (101 reviews)
3BR Wailea home on 1st hole of golf course. Ground floor, private entrance, large lanai, beach gear, 2 pools, tennis club access, walk to beaches & shops.
$487/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (100 reviews)
Grand Champions Villas is a beautifully remodeled 1 bed/2 bath vacation rental in Wailea, Maui. It has ocean views, quiet surroundings, and central A/C.
$434/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (100 reviews)
Refurbished ground-floor unit in Wailea Ekahi Village beachfront. King bed, pull-out sofa, A/C, ceiling fans, garden views, private lanais. Steps from pool & beach. Near top resorts & shops. Features shuffleboard, pickleball, oceanfront pavilion.
Location: Ekahi Village , Wailea
Bedrooms: 1 - K (sleeps 5)
5 (98 reviews)
Beautifully upgraded and fully air-conditioned 1 bedroom, 2 bath vacation rental in Ekahi Village, Wailea with ocean and mountain views, just steps away from the beach and pools.
$1529/nt (avg.)
Location: Wailea
Bedrooms: 4 - KQKKX (sleeps 10)
5 (97 reviews)
Maui Meadows Guesthouse is a 4-bedroom, 5-bath, 2700 sq ft house with a heated pool, hot tub, waterfall, cabana, outdoor shower, and parking. It's close to beaches, golf, shopping, and restaurants.
$421/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (97 reviews)
Exquisite 1-bed, 2-bath condo with stunning ocean views. Enjoy a modern open-concept living area, private lanai, full kitchen, and dedicated office space. Access to 4 pools, beachfront pavilion, and Keawakapu Beach. Ideal for relaxation.
$833/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 2 - KK (sleeps 6)
4.8 (173 reviews)
Luxurious 2BD/2BA condo in Grand Champions with 2 master king suites, upgraded kitchen, vaulted ceilings, AC, beach amenities, and sunset views.
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 2)
4.9 (128 reviews)
The Tree Top One Bedroom is an elegant, 2nd floor unit with a tropical modern king bedroom, spacious bath, well-stocked kitchen, and a sunny lanai with a washer/dryer. It offers privacy amid tree top blooms and tropical birdsong.
$424/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KTTX (sleeps 4)
4.9 (128 reviews)
Luxury 2Bd/2Ba condo in Wailea Ekolu, Hawaii with scenic ocean/mountain views, contemporary furnishings, AC, full kitchen, and outdoor dining.
$301/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 1 - KX (sleeps 4)
4.9 (128 reviews)
Newly purchased 1BR/2BA condo at Grand Champions Villas with ocean view lanai & front row view of Wailea Blue golf course. AC, free wifi, parking, 2 pools/jacuzzis, BBQs, beach gear. Close to beaches, shopping & dining. Can accommodate up to 4 guests.
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - KKT (sleeps 6)
4.9 (127 reviews)
Luxurious, modern retreat in Wailea with ocean glimpses from the lanai. Fully air-conditioned with all new appliances, beach gear, and high-quality linens. Family-friendly with a private second bedroom and low-profile tub. Free laundry, parking, Wi-Fi, and long-distance calling.
$1029/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - KQT (sleeps 5)
5 (94 reviews)
Newly remodeled 2BR/2BA condo with ocean views, steps from Polo Beach. Enjoy AC, pool, BBQ, herb garden, and Wailea resorts.
$1122/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - KK (sleeps 4)
5 (94 reviews)
Experience paradise in this updated oceanfront condo at Polo Beach Club! Enjoy breathtaking views, steps from the beach, and access to private pool and BBQ.
$711/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KQK (sleeps 6)
5 (94 reviews)
Wailea Ekahi Unit 32C is a renovated and upscale vacation condo with ocean views and close to the beach. It has two master suites, high-end amenities, and two private lanais. The property provides beach equipment, free Wi-Fi, and an entertainment system.
$754/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KXKQ (sleeps 6)
5 (93 reviews)
Two 2-bedroom units in Ekahi Village with ocean views, renovated interiors, and gourmet kitchen. Convenient location near Ulua Beach and Wailea shops.
$678/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - KQ (sleeps 4)
5 (93 reviews)
Recently remodeled 2BR/2BA unit in Wailea, Maui. Smart home with Google Assistant and voice-controlled lighting. Private patio with BBQ, AC, and WiFi.
Location: Grand Champions , Wailea
Bedrooms: 1 - KK (sleeps 2)
5 (92 reviews)
Luxurious 1bed/2bath suite in exclusive Wailea resort with high-end furnishings, Italian marble flooring, fully-equipped kitchen, and beach gear. Enjoy convenient access to pools, hot tubs, grills, golf course, tennis club, shopping, dining, and beaches.
$352/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 1 - Q (sleeps 4)
4.9 (121 reviews)
Luxury 1BR/2BA condo in Wailea's Grand Champions Villas with beautiful views of Old Blue golf course and Haleakala. Free parking, WiFi, and amenities.
$651/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - KTT (sleeps 4)
4.9 (119 reviews)
Palms at Wailea #1503: Inner circle location with stunning views, walk-out access to central grounds and pool. Custom designed with full kitchen, air conditioning, and soundproofed second bedroom. Walking distance to beach, shops, and promenade.
$601/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - (sleeps 6)
4.9 (119 reviews)
Experience luxury living in a 2BR/2BA air-conditioned condo at Wailea, Maui, boasting stunning ocean and volcano views. Amenities include a fully-equipped kitchen, washer/dryer, and beach gear. Sleeps six adults comfortably. Access pristine beaches, world-class golf, and dining.
$609/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 4)
5 (88 reviews)
Renovated ground floor unit with easy access, modern decor, and AC. Steps away from pool and beach, private lanais, and bar for socializing.
$849/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KQ (sleeps 4)
5 (87 reviews)
Luxury 2-bedroom condo with 180-degree ocean view, Japanese-style Jacuzzi tub, gourmet kitchen, and beach access. Panoramic 3-island ocean view.
$527/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KKX (sleeps 6)
4.9 (117 reviews)
2BR, 2BA unit in Wailea Ekolu with kitchen, A/C, washer/dryer, and spacious living area. Includes beach gear, community grills, heated pools, and sunset views from lanai. Near golf, tennis, beaches, shops, and eateries.
$2586/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 2 - KXT (sleeps 6)
5 (85 reviews)
Wailea Beach Villas offers a luxurious 2 bedroom + den/2 bath penthouse villa with a private elevator, BBQ, and ocean views. Amenities include pools, hot tubs, fitness center, and beach attendants. Located near golf courses, spas, and upscale shopping/dining.
$898/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 2 - KK (sleeps 4)
5 (85 reviews)
Wailea Ekahi Unit 41C: 2 master suites, ocean views from lanai, close to pool, beach access, well-appointed with beach toys, entertainment system.
$1610/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 4 - KXKQ (sleeps 8)
4.9 (113 reviews)
Newly renovated townhouse-style villa with 4 private bedrooms, 3.5 bathrooms, vaulted ceilings, Italian cabinetry, and a secure garage. Closest to the pool and beach, with a semi-private backyard. Features a 5-star pool, sauna, and waterfall.
$1800/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKQT (sleeps 7)
5 (82 reviews)
Luxurious Beachfront Penthouse with panoramic ocean views, gourmet kitchen, Viking grill, infinity pool, spa, concierge, fitness center, and more!
$461/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KQT (sleeps 5)
4.9 (110 reviews)
Spacious 2 bed/2 bath remodeled ground floor condo with stunning ocean views of Molokini, Kaho'olawe and Lana'i. Short walk to Wailea shops and beaches. Updated amenities, keyless entry, and free WiFi. Ideal floor plan with separate wings for privacy. No stairs.
$445/nt (avg.)
Location: Grand Champions , Wailea
Bedrooms: 2 - KQX (sleeps 6)
4.9 (109 reviews)
Vacation home with 2 bedrooms, 2 bathrooms, private lanai, and beautiful views. Access to 2 pools, BBQ areas, golf, tennis, and 5 nearby beaches.
$732/nt (avg.)
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - KK (sleeps 8)
5 (81 reviews)
Renovated 2BR/3BA condo on 10th hole of Blue Golf Course in Wailea. Ocean views, 2 lanais, 2 BBQs, split system AC, beach gear, and fully equipped kitchen. Walk to shops, restaurants, and beaches. Self check-in/out. No contact with owner necessary.
$404/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KTT (sleeps 4)
4.9 (109 reviews)
Spacious 1 bed, 2 bath condo with fully renovated kitchen, private laundry, 2 lanais, ocean & mountain views, 4 pools, beach gear, sleeps 4.
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (81 reviews)
Wailea Grand Champions #162: Top floor corner unit w/ golf & ocean views, walking distance to beaches, newly furnished, fully equipped kitchen, 2 pools, BBQs.
Location: Ekahi Village , Wailea
Bedrooms: 1 - KX (sleeps 3)
4.9 (109 reviews)
Ocean-view studio at Wailea Ekahi Village #48-D offers upscale furnishings, a king bed, sofa bed with memory foam mattress, SmartTV, and AC. Enjoy stunning lanai views and community grilling stations. Close to shops, restaurants, golf courses, and beaches. Sleeps 3.
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 2)
4.9 (108 reviews)
Tropical studio with private lanai, king bed, remodeled bath, and kitchenette. Quiet corner unit with treetop views, pool access, and free parking.
Location: Hoolei , Wailea
Bedrooms: 3 - XKQK (sleeps 10)
5 (80 reviews)
Luxury 3BR/3.5BA condo near the beach with breathtaking views. Private elevator, gourmet kitchen, lanai with BBQ, and pool with waterfall. Sleeps up to 10.
Location: The Palms at Wailea , Wailea
Bedrooms: 1 - XK (sleeps 4)
4.8 (143 reviews)
Ground floor villa w/ large lanai & sliding doors expanding living room to 1500 sq ft. Shared pool & hot tub w/ ocean views. Full entertainment system & BBQ.
$534/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - QK (sleeps 4)
4.9 (106 reviews)
Experience paradise at our spacious 1 bed/2 bath condo in Wailea Ekahi, South Maui. Includes a king bed, queen murphy bed, 4 pools, lush gardens, and beach access. Walking distance to golf, tennis, shops, and restaurants. Enjoy the lanai and tropical landscaping.
$598/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - (sleeps 4)
4.9 (105 reviews)
Fully-renovated 1BR/2BA condo with ocean views, located near a quiet pool and beachfront pavilion. BBQ facilities, picketball court, and green belt.
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - QK (sleeps 6)
5 (78 reviews)
Spacious 2-story, 2BR/2.5BA townhouse in Wailea with ocean & Haleakala views. Fully furnished, new furniture, appliances, split AC, 2 lanais, 2 pools.
$1333/nt (avg.)
Location: Hoolei , Wailea
Bedrooms: 3 - KK (sleeps 8)
5 (77 reviews)
Luxury 3BR villa in Hawaii's #1 resort, with ocean views, gourmet kitchen, private lanai, pool, jacuzzis, fitness center, and beach access.
Location: Grand Champions , Wailea
Bedrooms: 2 - KQ (sleeps 4)
4.9 (103 reviews)
2nd floor ocean view condo with double master bedrooms, newly renovated kitchen and baths, on-site manager, and beach equipment provided.
$492/nt (avg.)
Location: The Palms at Wailea , Wailea
Bedrooms: 2 - KTX (sleeps 6)
5 (75 reviews)
Luxurious 2 bed, 2 bath vacation rental condo at The Palms in Wailea. Fully remodeled with AC in every room, private guest room, and ocean views.
Location: Wailea Ekolu , Wailea
Bedrooms: 2 - (sleeps 4)
5 (75 reviews)
Enjoy a serene 2-bed, 2-bath condo with breathtaking Wailea Blue golf course and ocean views. Features include AC and washing machine. Ideal for a relaxing getaway.
$447/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KQ (sleeps 4)
4.8 (135 reviews)
Panoramic ocean view, renovated 1 bed/2 bath condo, oversized lanai, Tommy Bahama furniture, AC, WiFi, fully equipped kitchen, short walk to beach/pools.
$1153/nt (avg.)
Location: Polo Beach Club , Wailea
Bedrooms: 2 - XQK (sleeps 5)
4.9 (100 reviews)
"Relax in style at Polo Beach Club! Updated 2 bed/2 bath with private lanai and ocean views. Steps from Polo Beach and Wailea beach path. Beach gear included."
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 2)
4.9 (99 reviews)
Affordable top floor studio condo in Wailea with modern tropical furnishings, king bed, private lanai, upgraded kitchenette, and washer/dryer. Walking distance to white sand beaches, two pool and whirlpool spa areas, and preferential rates for golf and tennis.
$333/nt (avg.)
Location: Ekahi Village , Wailea
Bedrooms: 1 - KQ (sleeps 4)
5 (73 reviews)
Beautiful 1BR smoke-free condo in Ekahi Village, less than 4 min walk to Keawakapu Beach. Private ground floor unit in Building 19, 4 swimming pools, BBQ pavilion, updated bathroom, king bed, free long distance calls, high-speed internet, Apple TV and Netflix.
$3244/nt (avg.)
Location: Wailea Beach Villas , Wailea
Bedrooms: 3 - KKTX (sleeps 8)
5 (73 reviews)
Wailea Orchid Villa is a luxurious 3-bed penthouse with stunning Pacific Ocean views. It has a gourmet kitchen, marble floors, and sleeps up to 8.
Location: Grand Champions , Wailea
Bedrooms: 1 - K (sleeps 4)
5 (73 reviews)
Fashionably decorated, top floor 1BR/2BA condo with unmatched ocean views, modern furnishings, high ceilings, and access to Grand Champions Resort amenities.
12