Wailea Vacation Rentals

Escape to Aloha Moon. This calming island hideaway will have you falling in love all over again!

Tiki Tiki is a one of a kind experience. There’s nothing quite like it on Maui. From the plastered walls, soaking tub, luxury robes & cooling bamboo sheets.

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.

Ground floor, remodeled condo with ocean views in Ekahi Village. Short walk to the beach. Fully stocked kitchen, washer/dryer, beach amenities.

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.

Luxurious and affordable vacation rental in Wailea, Maui with stunning views, modern finishes, and access to 5 beaches, golf courses, and shopping.

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.

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.

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.

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.

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.

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.

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.

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.

Beautifully remodeled top floor condo with sweeping ocean and golf course views. Private lanai, designer kitchen, upscale washrooms, and tropical king bedroom. No shared interior space. .

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.

Elua Village 402 is a fully remodeled condo with a warm island feel, custom teak cabinets, granite counter tops, and top of the line appliances. The unit has a 180-degree view and is in a quiet location.

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.

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.

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.

Clean, open condo w/ ocean view & lanai in Wailea Ekolu. Close to beautiful beaches, golf courses, shopping, & dining. Perfect for a Maui retreat.

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.

Luxurious tropical retreat in Maui's Ekahi Village. Spectacular ocean and volcano views, privacy, short walk to Keawakapu Beach. Modern amenities.

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.

Beachfront penthouse with panoramic ocean views, 4 bedrooms, 3 baths, complete 2017-2018 renovation, sleeps 8, direct elevator access, on-site amenities.

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.

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.

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.

Stunning 2BR vacation rental in Wailea with breathtaking ocean views, central air conditioning, flat screen TV, DVD player, Wi-Fi, and more.

1BR/2BA ocean view condo in Wailea Ekahi Village. Direct access to Keawakapu Beach. 4 pools, AC, newly remodeled kitchen, memory-foam king bed.

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.

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.

1BR/1BA upper level condo, newly furnished, air conditioned, with lanai, WiFi, parking, and ocean views. Close to beaches, trails, and shopping.

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.

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.

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.

Wailea Ekahi 39E is a 2nd floor condo with unobstructed ocean views, well-appointed kitchen, home office, 65" TV, WiFi, and beach equipment.

Luxury top-floor 2BR/2BA condo w. ocean view, beach access, pool, and beach toys. Professionally decorated, walk to restaurants, and coffee shops.

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.

Luxurious 3 bed, 3.5 bath townhome at Hoolei Wailea Beach with private elevator, ocean views, BBQ area, entertainment system, and resort amenities.