Apartment vacation rentals in Wailea

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Quick stats about apartment rentals in Wailea

  • Total vacation rentals

    Explore 250 vacation rentals in Wailea

  • Nightly prices starting at

    Wailea vacation rentals start at G$23,014 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,390 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    250 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!

Top-rated apartment rentals in Wailea

Guests agree: these apartments are highly rated for location, cleanliness, and more.

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Superhost
An inviting private balcony features comfortable seating, including a round, woven chair and rattan seats with cushions. A telescope is positioned for views of the ocean and adjacent landscaped garden, showcasing palm trees swaying in the breeze and a glimpse of the heated pool.
Apartment in Kihei

The Whale Watch 208-Oceanfront Kihei

HOTEL ZONED, NOT affected by new Hawai’i legislation banning 1/2 of Maui’s Airbnbs Next to Pacific Whale Sanctuary, this newly renovated 2bed, 2bath is a modern oceanfront oasis. On the 2nd floor, overlooking a heated pool with sweeping ocean, sunset, and mountain views. Steps away to a protected ancient Hawaiian beach perfect for snorkeling, viewing sea turtles and whales shopping, dining and sightseeing just moments away. Sip cocktails or grill out on the rooftop deck with 360* views of Maui.

4.88 out of 5 average rating, 139 reviews
Top guest favorite
A spacious living area features a large sectional sofa adorned with various throw pillows. A wooden coffee table sits in front of the sofa, while built-in shelves display decorative items and a flat-screen TV is positioned for easy viewing.
Apartment in Wailea

Go Golfing from a Peaceful Apartment in a Beach Community

Unit #903 – Key Features Garden views, ground floor A/C (3 zones) Lanai seating Quiet Updated appliances; washer/dryer Primary: king bed Second: twins (convert to king) Sleeper sofa Kitchen TV, Wi-Fi Free U.S./Canada calls Amenities Beach chairs, umbrella, boards, cooler, towels Baby gear: Pack ’n Play Pool, hot tubs Location Wailea—near beaches, golf, shops, dining. Keawakapu Beach is a short walk. Guest Support On-island contact after booking. Parking Dedicated space + guest parking.

4.88 out of 5 average rating, 173 reviews
Top guest favorite
Apartment in Kihei

Updated 1st Floor Maui condo

A welcoming 1st floor, one bedroom 723 sq ft condo at Kihei Kai Nani complex across from beautiful Kamaole II beach, in Kihei. It is recently updated, fully furnished and equipped with full kitchen, Queen size bed and a crib for an infant and a twin air mattress (no sofa-bed). NOTE: The Kihei Kai Nani resort has been zoned as a Hotel / Business Resort since it was built in the 70's. It is not one of the resorts being targeted by current legislation to curb Short Term Rentals on Maui.

4.76 out of 5 average rating, 132 reviews
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

Wailea Large Ocean View Condo

Experience Maui from your spacious retreat in the heart of Wailea. Enjoy ocean views, tropical breezes and beautiful sunsets from your covered lanai. Walk to The Shops at Wailea and restaurants, with golf and tennis nearby and Wailea Beach just a 5-minute drive. The bright, open-plan living area provides plenty of space to relax after exploring Maui. Skip the crowded hotel and enjoy the privacy of your own island home. Come experience the warmth of aloha and beauty of Wailea.

4.89 out of 5 average rating, 111 reviews
Guest favorite
A spacious living area featuring high vaulted ceilings and large windows offering ocean views. Comfortable seating arrangements include an oversized sofa and stylish armchairs. A dining table accommodates four, complemented by a decorative feature wall. Natural light enhances the airy atmosphere throughout the room.
Apartment in Wailea

Luxurious Wailea Ocean Vistas

Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while enjoying a charming well-designed hideaway. We have considered every detail to provide the most effortlessly luxurious stay possible. With beaches nearby and two pools onsite, this island paradise has everything and more.

4.98 out of 5 average rating, 108 reviews
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

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

4.9 out of 5 average rating, 343 reviews
Top guest favorite
A covered private lanai features a comfortable seating arrangement with a coffee table, while natural light enhances the space. Sunset views are visible through palm trees, providing a serene backdrop. The entrance to the indoor living area is seen through glass doors.
Apartment in Wailea

Ocean Front Vibes Maui

Wake up to panoramic ocean views and end your day with sunsets from your private lanai in this top-floor corner condo at Haleakala Shores. Just steps to Kamaole Beach Park III with easy elevator access. Beautifully remodeled in 2020, fully stocked, and walkable to dining, shops & snorkeling. Light road noise possible. See more videos & details on social at oceanfrontvibesmaui Maui's airport code is OGG

4.96 out of 5 average rating, 202 reviews
Superhost
Apartment in Kihei

OCEANFRONT, Prestigiously REMODELED Chic Condo**

An incredible beachfront location and boutique tranquility make this condo feel like your own luxury resort. Watch the waves tumble on shore as you sip your favorite cold beverage from your own private lanai facing the golden sands and turquoise waters of Kamaole I Beach. Lush garden areas, high ceilings, original artwork and a secluded feel make this unit the perfect getaway.

4.85 out of 5 average rating, 168 reviews
Guest favorite
Tall palm trees frame a view of a serene coastline at dusk, where gentle waves meet the shore. The scene includes a hammock suspended between two trees, and soft pastel hues illuminate the sky, transitioning from light blue to warm pink. A green lawn completes the tranquil atmosphere.
Apartment in Kihei

Charley's Hideaway (Oceanfront)

Say Aloha to this 2 bedroom, attached beach bungalow built for family, friends and guests to relax and read, nap in the afternoon and play in the surf. Places like this have become a rarity in the islands, this charming, old Hawaiian house sits on a bluff overlooking the beach and predates a time before resorts and generic condo’s became the norm.

4.91 out of 5 average rating, 136 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

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.

4.92 out of 5 average rating, 133 reviews
Guest favorite
An open living area features a modern kitchen with stainless steel appliances and a light countertop. A comfortable gray sectional sofa is arranged around a small coffee table on a patterned rug. Shelving displays decor, and a large mirror reflects the space, enhancing brightness.
Apartment in Kihei

Next to Beach, Foods & Shops - Updated w/ View!

Centrally located in south Downtown Kihei. The place is literally next to the world famous Kameole Beach, next to many restaurants, next to bakery, next to ice cream shop, next to bar, next to small market. Literally walk to everything. Your family will be close to everything when you stay at this centrally-located place.

4.95 out of 5 average rating, 224 reviews
Superhost
Apartment in Wailea

Hawaiian-style 1 BR Condo - steps from the beach!

This beautifully decorated Hawaiian-style, first floor, one bedroom condo is the perfect place for you to stay during your vacation in Kihei, Hawaii. Located inside the Hale Kamaole resort and just across the street from Kamaole Beach Park III, this condo has the ideal location!

4.83 out of 5 average rating, 187 reviews

Popular amenities for Wailea apartment rentals

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$72,809 GYDG$80,968 GYDG$73,227 GYDG$67,369 GYDG$61,720 GYDG$58,163 GYDG$57,745 GYDG$55,234 GYDG$55,653 GYDG$55,653 GYDG$59,628 GYDG$71,554 GYD
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

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