Waterfront holiday rentals in Wailea

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Top-rated waterfront rentals in Wailea

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

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Top guest favourite
Apartment in Wailea
4.99 out of 5 average rating, 125 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Top guest favourite
A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.
Apartment in Wailuku
4.98 out of 5 average rating, 106 reviews

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

Guest favourite
An outdoor dining area features a glass table and white chairs, situated on a balcony with a view of the ocean. Palm trees frame the scene, and distant mountains can be seen across the water, creating a serene coastal atmosphere.
Apartment in Kihei
4.91 out of 5 average rating, 128 reviews

Full Ocean- Full Sunsets- Beaches at Royal Mauiian

Hawaii License: T-174-283-2640 Full ocean & beach front - all year sunsets. Royal Mauiian - Highly sought location in S. Kihei. Nicely done 1 BR - 1 BTH Nicely furnished, very streamlined open feel. Walk to restaurants, steps to Kam 1 beach, close to shops & activities. Rent a paddleboard, buy Hawaiian memorabilia, or shop at Harvest Moons - close by. Split Air in Bedroom & Living Area. Fully equipped kitchen. In Unit Laundry GET & TAT tax total of 17.75% included in final price.

Top guest favourite
A serene beach scene is captured at sunset, with canoes resting on sandy terrain. The sky displays soft hues of orange and yellow, reflecting over the water. A sign stands nearby, providing information about the area, framed by gentle foliage and distant clouds.
Apartment in Kihei
4.9 out of 5 average rating, 148 reviews

Beautiful Studio Condo with Partial Ocean View

This second-floor ocean view studio has everything you need to feel at home: Fully equipped kitchenette, dining area, comfy queen bed, cozy sitting area, SmartTV with streaming apps, Wifi, bathroom with bathtub, beach equipment, and much more. Resort amenities include a coin/card operated laundry room, pool, hot tub and tennis court. Less than 1 mile from shopping and restaurants. Enjoy stunning sunset views from the lanai or cross the street to Kalepolepo Beach to be with the sea turtles.

Top guest favourite
A modern kitchen is shown with sleek gray cabinetry and stainless steel appliances. An island seating area with two wooden stools is present, topped with a decorative tray and two cups. Pendant lights with blue shades illuminate the space, enhancing the open and functional layout.
Apartment in Kihei
4.96 out of 5 average rating, 189 reviews

Renovated Condo | 3 Min Walk to Toes in the Sand!

Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

Top guest favourite
A bright living area features sliding glass doors that open to a private lanai with ocean views. Comfortable seating options include a cozy sofa and armchair, complemented by a round coffee table and decorative pillows. Natural light fills the space, creating a welcoming ambiance.
Apartment in Kihei
4.97 out of 5 average rating, 152 reviews

Stunning Ocean Views

Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

Top guest favourite
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Apartment in Kihei
4.99 out of 5 average rating, 244 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Top guest favourite
A private lanai offers a breathtaking view of the ocean and sandy beach. Two light-colored chairs with striped cushions are positioned around a small round table, accompanied by two glasses of water. Lush greenery and palm trees frame the serene setting.
Apartment in Kihei
5 out of 5 average rating, 182 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom have maple cabinets and elegant granite counter tops. There is a comfortable king size bed, a well-stocked kitchen, central AC, with all new bamboo floors throughout, and a new washer / dryer. The Condo is owned and maintained by Maui residents.

Top guest favourite
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.
Flat 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.

Guest favourite
A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.
Apartment in Wailuku
4.94 out of 5 average rating, 139 reviews

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

Top guest favourite
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.
Flat in Kihei
4.98 out of 5 average rating, 100 reviews

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

Whale Season 2026 is here! Best location to see them all 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 favourite
A modern kitchen is showcased with stainless steel appliances, including a refrigerator and oven. The wood cabinetry complements the granite countertops. A kitchen island with bar seating enhances the space, while pendant lights hang above, illuminating the area. A window provides a view of the outdoors.
Apartment in Kihei
4.89 out of 5 average rating, 361 reviews

In the heart of S Kihei! Across Best Beach!

Say aloha to this beautiful beach side retreat in easygoing Kihei! It's across the street from some of the worlds most famous beaches. Beautiful completely renovated mineral pool and grill area. Everything is in walking distance, restaurants, grocery stores, and surfing lessons. We provide beach chairs, beach umbrellas, coolers, beach towels, there is NO snorkel gear.

Popular amenities for waterfront rentals in Wailea

When is the best time to visit Wailea?

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Avg. price$501 SGD$513 SGD$500 SGD$455 SGD$382 SGD$428 SGD$386 SGD$365 SGD$368 SGD$353 SGD$414 SGD$476 SGD
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Quick stats about waterfront rentals in Wailea

  • Total holiday rentals

    Explore 320 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at $206 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,270 verified reviews to help you choose

  • Family-friendly holiday rentals

    210 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    310 properties feature pools

  • Rentals with dedicated workspaces

    240 properties have a dedicated workspace

  • Wifi availability

    320 of Wailea holiday rentals include wifi 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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