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, 140 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
An outdoor dining area is presented on a covered balcony, featuring a wooden table set with plates adorned with pink flowers. The view includes palm trees and neighboring structures, with a bright sky in the background.
Apartment in Wailea
4.89 out of 5 average rating, 108 reviews

Wailea Large Ocean View Condo

Enjoy the comfort and cleanliness of your own space. Located in the heart of Wailea, Grand Champions Villas is next to a golf course, tennis courts, a short walk from the Shops of Wailea, restaurants and a 5 minute drive to Wailea Beach. Open floor plan living area which opens to a covered lanai area for outdoor entertaining and dining with lush tropical, ocean views and stunning sunsets. Why stay in a crowded hotel when you can relax in the safety of your own large condo. Long stay discounts.

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, 141 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 spacious sleeping area features a pink bedspread with a view of a private balcony. A wooden dresser holds a flat-screen television, while a glass-top table and two chairs are positioned nearby, creating a cozy seating arrangement amidst tropical foliage.
Apartment in Wailea
4.91 out of 5 average rating, 397 reviews

Fall Special! - King Bed - Closest to Ocean!

We're happy to assure you that our condo in South Maui is fully compliant and properly zoned for short-term rentals. Book with confidence! As Maui residents, my wife and I can truly say there is no better place to live or vacation than Maui Banyan.. We bought our condo with a long-term goal in mind.. retirement later but fun now. We ask that if you choose to stay with us that the rental agreement that will be sent to you is respected and followed. Welcome to paradise!

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, 141 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!

Superhost
A coastal scene features rocky shoreline transitioning into gentle waves. Lush greenery and palm trees are visible along the land, contrasting with the blue ocean. The horizon reflects warm light, suggesting a serene atmosphere at sunset. The natural landscape provides a tranquil environment.
Apartment in Kihei
4.83 out of 5 average rating, 266 reviews

Quiet Studio, Great location across from beach

My place is located in sunny Kihei and only 20 minutes from the airport. The studio is right across the street from Kalepolepo Beach and the Whale Sanctuary. The studio is centrally located in Maui near many beaches, restaurants, and shopping centers which is very convenient. The famous Ululani's shaved ice along with various fruit stands are only a few minutes away. You can whale watch, paddleboard, snorkel, sight see, and enjoy the most amazing sunsets in Maui!

Guest favorite
An oceanfront view is captured from the lanai, showcasing gentle waves lapping at a sandy beach below. Lush palm trees line the shore, swaying in the breeze under a bright blue sky with scattered clouds.
Apartment in Kihei
4.92 out of 5 average rating, 142 reviews

Ocean Front With Ocean View! AC, King Bed, 2 Bath!

E Komo Mai to our remodeled oceanfront unit with stunning ocean view at the Nani Kai Hale. Feel the ocean breeze, listen to the waves, and watch the whales and sunsets from our tranquil, oceanfront condo. From our comfortable lanai seating you have view of the Islands of Molokini, Kahoolawe and Haleakala while enjoying your morning coffee, evening cocktail, or anytime meal. Walk along the beach and experience beautiful sunsets framed by swaying coconut palms.

Top guest favorite
A private lanai is shown, furnished with two lounge chairs and a round table. The area overlooks lush greenery and the ocean in the distance, framed by a wooden pergola. Bright blue skies complement the serene, outdoor setting.
Apartment in Wailea
5 out of 5 average rating, 203 reviews

Ocean View Loft -Own Private Hot Tub

Private outdoor entrance to your own space. No need to interact w/others. Like your own home. Secluded romantic couples retreat above Wailea 3-5 mins to Maui's best beaches/restaurants/shops/resorts. Bright open loft plan. 200˚rare ocean views. Large loft overlooks multiple islands/coast lights/star gazing. Secluded + sexy. Tropical private garden w/own hot tub. Full bath inside. Immaculate.Original art, clean contemporary design, due west exposure.

Guest favorite
A serene view showcases a circular pool surrounded by palm trees and tropical greenery. The backdrop features a cloudy sky over the ocean, with a glimpse of beach access visible. Smaller images highlight the interior amenities, including a modern bathroom and living area with ocean views.
Apartment in Kihei
4.91 out of 5 average rating, 310 reviews

Ocean View, 1 minute walk to the beach 2BR/2BA

You'll love this stylish newly renovated condo with stunning ocean view. 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, 3 pools, 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 parking

Guest favorite
An inviting lanai features a table and chairs, overlooking the ocean, with tropical palm trees framing the view. Nearby, the serene pool area is surrounded by lush greenery, while a spacious living area showcases a dining table adorned with fresh fruit and a well-equipped kitchen, enhancing the relaxed ambiance.
Apartment in Kihei
4.87 out of 5 average rating, 189 reviews

*Last Minute Deal Direct Oceanfront Remodeled Unit

This 1 bedroom, 1 bathroom 732 square foot unit is located just steps from the glittering Pacific Ocean. A water front complex, Kihei Beach Resort is conveniently located, beautifully updated and ideal for your next getaway! It comfortably accommodates up to four people. Take a stroll on the beach, bask in the trade winds or sip your coffee on your over-sized lanai overlooking the ocean. This romantic space will leave you with lifelong memories.

Guest favorite
Apartment in Wailuku
4.92 out of 5 average rating, 263 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.

Top guest favorite
A scenic view showcases palm trees swaying gently against a backdrop of the blue ocean and distant mountains. The foreground features lush greenery, while a clear sky enhances the vibrant colors of the landscape.
Apartment in Kihei
4.9 out of 5 average rating, 252 reviews

Cozy Central Kihei Condo

Aloha I would love to host you at my cozy place in Kihei! Great Location, Great Views, Great Value! Centrally located and walking distance to beaches, restaurants, shopping and more! Kihei is known for its year round sun and amazing beaches. Make sure you get the most for your money by staying in a residential, well appointed and centrally located condo! This is a 3rd floor unit that requires the use of stairs.

Popular amenities for Wailea apartment rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$72,442 GYDG$73,280 GYDG$72,861 GYDG$57,158 GYDG$54,436 GYDG$59,252 GYDG$57,786 GYDG$55,274 GYDG$55,693 GYDG$57,368 GYDG$56,949 GYDG$70,767 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 210 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at G$23,031 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,870 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    200 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    210 of Wailea vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Wailea rentals

  • 4.8 Average rating

    Wailea stays are highly rated by guests—averaging 4.8 out of 5!

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