Apartment vacation rentals in Wailea

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Top-rated apartment rentals in Wailea

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Guest favorite
The exterior of the end unit on the second floor is showcased, featuring a light-colored facade with green accents. Lush tropical plants surround the base, and a set of stairs leads to the entrance, providing a sense of privacy.
Apartment in Wailea
4.94 out of 5 average rating, 142 reviews

Private Top-Floor Apartment with Mountain and Ocean Views

Many units in the Palms only have air conditioning in the master bedroom. We substantially upgraded the unit (new floors, cabinets, appliances), and while we were at it we installed AC throughout the unit. -Unit #906 -Beautiful Views -End Unit on Second Floor Provides Awesome Privacy -Air conditioning throughout unit...3 zones -Private Lanai With It's Own Weber Gas BBQ -2 Lounge Chairs -Quiet Location -All New Appliances -Brand New Full Sized Washer And Dryer -Luxury King Bed In The Master Bedroom -2 Twin Beds In The Second Bedroom can Also be Converted into a King Sized Bed -Free WiFi Internet -Free Local And Long Distance Phone Calls Within US And Canada -Pullout Sleeper Sofa -Fully Equipped Kitchen With BBQ Platters And Utensils -Flat Screen TV In The Living Room -Pac-n-Play and Booster Seat for young ones -Keawakapu Beach just a short walk away -Tommy Bahama Beach Chairs -Boogie Boards -Beach Umbrella -Beach Coolers -Pool / Beach Towels -Large Pool Area -Hot Tubs The entire condo and grounds are yours to enjoy. Wonderful pool and spa just a 2 minute walk from the unit. My On-Island Representative is available when needed. She lives in Kiehi and is handles several units for me. You will receive her phone number and email address upon booking the unit. Rest assured someone is on call should you need help. If golf, shopping, and being pampered is the aim, then Wailea is ideal. Walk to Keawakapu, one of Maui’s best beaches, play at 3 championship courses at Wailea Golf Club, and choose from 3 top spas. For an ocean adventure, rent an outrigger canoe. One dedicated parking spot just outside the front door to your condo. Multiple first come first serve parking spaces 40 feet away from this spot. We provide beach gear (chairs, umbrella, boogie boards, cooler) and baby gear (booster seat, pack n play).

Top guest favorite
A modern kitchen features sleek cabinetry and stainless steel appliances, including a refrigerator and microwave. A light grey tile backsplash complements the white marble countertop, which hosts a built-in stove. Natural light enters through a small window, enhancing the airy space.
Apartment in Kihei
4.93 out of 5 average rating, 106 reviews

High-end, On Beach, View Balcony, with Pool & BBQ!

Free Parking. Building is right on the beach and under 3 min walk to small market and world famous Ululani's shave ice shop. This condo is on the second floor with balcony with ocean view! This World famous Sugar Beach is in the backyard w/ 10 miles of sand. Fully Remodeled with High End Finishings. TWO FULL BATH. One with Tub and One with Shower. KING ADJUSTABLE BED. Split System AC. One in Living Room and One in Bedroom. Super Quiet. TWO TV's. One in the Living Room and One in the Bedroom.

Top guest favorite
The kitchen area features warm wooden cabinetry and sleek granite countertops, accented by pendant lighting. A spacious island with two high stools invites casual dining. Stainless steel appliances are visible, and the open layout allows for a seamless flow into the adjoining living area.
Apartment in Wailuku
4.95 out of 5 average rating, 100 reviews

Grnd Floor Oceanfront Condo- Great View, A/C,Wi-Fi

The convenient location in Maalaea leaves you minutes away from beautiful beaches, restaurants, and all Maui destinations. An open layout consisting of 1 bedroom and 1 bath gives an expansive feel to this exquisite unit. Central A/C. Luxury upgrades include: travertine flooring, custom kitchen and bathroom cabinetry, granite counter-tops, new stainless appliances, stone flooring and stone/glass shower. Meticulously maintained grounds along with a refreshing swimming pool and grilling area.

Top guest favorite
A serene landscape view features tropical greenery and palm trees leading to the ocean. Sun umbrellas are visible along the shore, providing shade, while calm blue waters stretch into the distance. Lush foliage surrounds the area, enhancing the tranquil outdoor environment.
Apartment in Wailea
4.96 out of 5 average rating, 142 reviews

Wailea Couples Retreat, 300 FT To Keawakapu Beach

Ekahi Ocean Studio is perfectly located in the lower village of Wailea Ekahi (ground floor), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat. You can spend your days lounging at the beach or oceanfront pool, running along the nearby beachfront pathway, exploring nearby Wailea restaurants and resorts or enjoying our cook's kitchen and your private Lanai.

Top guest favorite
A bright living area features a comfortable sofa and armchairs, complemented by a coffee table. Large windows offer stunning ocean views, while a dining table and chairs are positioned nearby. A TV sits on a wooden unit, and vibrant artwork adorns the wall.
Apartment in Kihei
4.93 out of 5 average rating, 147 reviews

Maui Oceanfront Penthouse at Nani Kai Hale (609)

Bask in the breathtaking ocean views from our Maui penthouse! Centrally located, our beautifully remodeled suite offers full beachfront, ocean and pool access. The master bedroom features an incredibly comfortable California king bed with an en suite bathroom and stone walk-in shower. There is also a king size cozy sleeper sofa in the living room which has direct access to the second full bathroom. The modern kitchen is fully equipped with everything you need!

Top guest favorite
A cozy living area features a sofa and coffee table, illuminated by natural light through large sliding glass doors. An outdoor seating area overlooks a tropical garden, with BBQ grills available nearby. A view of the community pool and palm trees adds to the relaxing atmosphere.
Apartment in Kihei
4.98 out of 5 average rating, 104 reviews

Walk to Everything- Beach, Eat, Shop, Whale Watch!

Whale Season 2026 is here! Best location to see humpback whales day long! We are centrally located in Kihei Town, in the Maui Vista Condominiums building #3 (peaceful & quiet located on the 3rd floor) - one of the best locations in South Maui! Stay with us and you'll be within walking distance of all the best attractions in Kihei! ✅ Best Beaches ✅ Surfing ✅ Snorkeling ✅ Restaurants ✅ Nightlife ✅ Shopping You name it- we are close to EVERYTHING!

Guest favorite
A serene coastal scene features a palm tree beside gently lapping waves. Inset images showcase a modern kitchen with stainless steel appliances, a pool area, and a beach view, illustrating the condo's amenities and nearby recreational options.
Apartment in Kihei
4.86 out of 5 average rating, 321 reviews

3 minutes walk to the beach 2BR/2BA Top floor

You'll love this stylish newly renovated condo. Enjoy easy walks to everything you desire for the perfect Maui vacation. This truly is the best holiday location on the island. You'll love the neighborhood, the shopping, the beaches, the pool, the kitchen, sunsets, restaurants, cafes, bars, turtles & whales! You'll be staying directly opposite the famous Charley Young beach! In the cutest little beach town on island. Complementary car park

Guest favorite
Apartment in Wailuku
4.92 out of 5 average rating, 268 reviews

1929 Restored 1BR Plantation Home | Walk to Town

Experience authentic Maui at The Blue Door on Church Street, a renovated 1930s plantation home in historic Wailuku. This one-bedroom villa features a King-sized Nectar bed, memory foam sleeper sofa, spa-like bath, and a fully equipped bar area. Enjoy the on-site infrared sauna and walk to cafés, restaurants, and shops. Centrally located near ʻĪao Valley, beaches, and top Maui attractions—your perfect base for adventure and relaxation.

Guest favorite
A bright, open living area features modern furnishings including a spacious sofa and lounge chairs. Large sliding glass doors provide views of the garden and ocean, while a ceiling fan enhances airflow. A round coffee table sits on a woven rug, complementing the hardwood floors.
Apartment in Wailea
4.94 out of 5 average rating, 100 reviews

A.R.A Retreats: Garden Oasis

Nicknamed “Garden Oasis” for its beautiful little garden walk out off the Lanai onto a beautiful field. While it also has a amazing view of the pacific ocean the beautiful private walkout really set the tone for a relaxing and private oasis. Wailea Ekolu Village is a three-minute drive or 18 minute walk to the beautiful golden sands of Wailea Beach. The Shops at Wailea, Monkeypod Kitchen and so much more just a short walk away!

Guest favorite
A private lanai features a round table set for two, complete with glasses and a bottle, with palm trees visible in the background. The cozy bedroom includes a queen bed and ample sunlight from large windows. The living area is designed with modern furnishings, showcasing a blend of tropical decor and comfort.
Apartment in Kihei
4.74 out of 5 average rating, 280 reviews

Best Location Across Best Beach! New AC throughout

This sunny second floor 621 square foot condo is located in the heart of Kihei. The complex (Kihei Kai Nani) boasts beautifully manicured tropical gardens, fruit trees, a large fresh water swimming pool, picnic tables, shuffleboard, an activity pavilion and several BBQs for our guests to use. Enjoy traditional Hawaiian decor, a private lanai and the warm Maui sunlight streaming through the many windows in this beautiful unit.

Guest favorite
A modern living area is featured, showcasing a comfortable sofa with decorative pillows and a coffee table. The open kitchen is visible in the background, equipped with stainless steel appliances and a countertop with bar seating. Light fills the space through large windows.
Apartment in Wailea
4.95 out of 5 average rating, 115 reviews

Kamaole Sands 7-207-Stunning Remodel-Large Lanai

This 1 bedroom, 2 bathroom condo was just completely remodeled with beautiful modern finishes. The condo is located in Building 7 at Kamaole Sands and has a large lanai. PMI Maui manages many units in South Maui. Please let us know if you are interested in any of our units and we will send you the Airbnb link to view all of our listings and reviews.

Guest favorite
A private Lanai is furnished with a round glass table and four comfortable chairs, overlooking lush green lawns and distant blue mountains. The serene outdoor space invites relaxation, enhanced by a warm tropical breeze and clear blue skies.
Apartment in Wailea
4.92 out of 5 average rating, 123 reviews

Grand Champions - Ocean & Golf View, King Bed, A/C

We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next to the Wailea Tennis Club and Wailea Blue Golf Course.

Popular amenities for Wailea apartment rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$72,369 GYDG$73,206 GYDG$72,787 GYDG$57,100 GYDG$54,381 GYDG$59,192 GYDG$57,728 GYDG$55,218 GYDG$55,636 GYDG$55,636 GYDG$59,610 GYDG$71,532 GYD
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

Quick stats about apartment rentals in Wailea

  • Total vacation rentals

    Explore 220 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at G$29,282 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,910 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    210 properties feature pools

  • Rentals with dedicated workspaces

    110 properties have a dedicated workspace

  • Wi-Fi availability

    220 of Wailea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wailea rentals

  • 4.9 Average rating

    Wailea stays are highly rated by guests—averaging 4.9 out of 5!

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