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.

Luxury 3-bedroom, 3-bath, 2500 sq. ft. Penthouse Villa J205 at Wailea Beach Villas with ocean views, gourmet kitchen, and resort amenities.

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.

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.

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.

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.

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

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.

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.

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.

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.

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

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

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.

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.

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.

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.

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

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.

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.

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.

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.

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.

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.

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

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.

Fully remodeled 2BR/2BA Maui condo with sweeping ocean views. 4-minute walk to the beach. Beautifully landscaped grounds, ocean-side pool, and pavilion.

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.

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.

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

Newly remodeled Wailea Ekahi Unit 39C, a ground floor condo with ocean views, 2 master suites, beach toys, entertainment system, and beach access.

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.

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.

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.

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

Luxurious 1300 sq ft Wailea Elua 201 ground floor unit offers stunning 180-degree panoramic ocean views, whale watching, and year-round sunsets from a 500 sq ft lanai.

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.