Waterfront vacation rentals in Wailea, Wailea-Makena

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Top-rated waterfront rentals in Wailea, Wailea-Makena

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

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Guest favorite

Condo

4.98 out of 5 average rating, 141 reviews

Spectacular ocean views Kihei @iconic IslandSurf

*PLEASE NOTE A 14.8% HAWAII STATE TA/GE TAX WILL BE ADDED AND COLLECTED BY THE END OF YOUR STAY COMPLETELY REMODELED THIS SUMMER IN A COMFORTABLE MODERN-TROPICAL STYLE. THE HIGHEST THREAD- COUNT LINENS AND TEAK THROUGHOUT THIS HIGH STYLED CONDO. HUGE VIEWS FROM THE MODERN KITCHEN, LIVING ROOM AND LANAI All SET IN THE HEART OF KIHEI. FABULOUS LOADS OF BEACH GEAR SURFING LESSONS DOWNSTAIRS BIKE RENTALS DOWNSTAIRS PARKS AND BEACHES ACROSS THE STREET 2 BLOCKS FROM SOME OF KIHEI'S FINEST RESTAURANTS

Guest favorite

Condo

4.96 out of 5 average rating, 104 reviews

Romantic Beach Retreat, New King Bed & A+ Wi-fi

Hale Kamaole: Romantic Bright & Airy Beach Condo Across The Street from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for couple's getaway, anniversaries, honeymooners. Washer/Dryer. Spacious lawns & tropical gardens w/ 2 pools, Tennis court & BBQ grills. Popular snorkeling area. Eddie Pu walking trail w/ plenty of wildlife just steps away. Walk to shops & restaurants.Free Parking Pass NB:17.712% Hawaiian Transient Tax

Guest favorite

Condo

4.87 out of 5 average rating, 261 reviews

Oceanfront Condo. Pool & Spa, 1 Br.

MAALAEA OCEANFRONT. Oceanfront lawn, panoramic views, full kitchen, washer/dryer, granite counters, oceanfront lanai, all supplies, beach gear, quiet... with pool, jacuzzi/spa, BBQ, TempurPedic queen bed, desk, free wi-fi & parking. Nearby uninhabited 5 mile long beach walk & swim, Rooms have fans and windows /screens that allow cooling breezes along with one A/C unit Peaceful Maalaea neighborhood. Centrally located to explore Maui, 15 minutes to airport. Adults(2) only. No smoking.

Guest favorite

Condo

4.99 out of 5 average rating, 169 reviews

Mana Kai 608- Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on incredible Keawakapu beach! This location is ideal, right on the border of Wailea and Kihei. We have designed our remodel with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests.

Guest favorite

Condo

5 out of 5 average rating, 158 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 are newly remodeled with maple cabinets and elegant granite counter tops. There is a very comfortable king size bed, a well-stocked kitchen, central AC, bamboo floors throughout, and a washer / dryer. The Condo is owned and maintained by Maui residents.

Guest favorite

Condo

4.99 out of 5 average rating, 104 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

Aloha and E Komo Mai! (Welcome) Where Heaven meets Earth! Immerse yourself in the best location and ocean front views to spend your luxury vacation experience in South Maui. This Mana Kai penthouse is on the 8th floor (unit 806) that includes two bedroom suites on the world famous Keawakapu Beach. Located on the longest sandy beach in Wailea (2.75 miles), you will enjoy excellent body surfing, whale watching, snorkeling, scuba diving paddle boarding and kayaking literally at your doorstep.

Guest favorite

Condo

4.97 out of 5 average rating, 102 reviews

NEW Ocean View 1 Bedroom Condo with Common Hot Tub

NEW to vacation market! This condo was designed, furnished, decorated as our 2nd home using high end appliances & décor. Your 5th floor ocean view unit is unobstructed; no sidewalk, no power lines, no parking lot. Tennis/pickle ball, pool, BBQ, putting green, HOT TUB and BEACH are steps away! Your living & bedroom have ocean views. Other communities have the bedroom on the parking lot side. An exceptional Unit. 17.5% TA Tax included (not on VRBO). Sunsets are magical from your lanai.

Guest favorite

Rental unit

4.95 out of 5 average rating, 119 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 favorite

Condo

4.93 out of 5 average rating, 152 reviews

Oceanfront Condo on magic Sugar Beach - Ocean View

•EAST/SOUTH MAUI IS OPEN FOR BUSINESS AND WELCOMING TOURISM• Life is sweet on Sugar Beach. Our oceanfront condo is fewer than 100 steps to a world-class beach that stretches for 5 miles. The smooth sand, gentle waves, and warm water create the ideal swimming experience. And when you are ready to come in, you can relax on our private beachfront lawn with your own lounge chair, table, and umbrella. Or maybe you prefer the pool? It’s perfectly maintained and private.

Guest favorite

Rental unit

4.9 out of 5 average rating, 100 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.

Guest favorite

Condo

4.96 out of 5 average rating, 182 reviews

Oceanview Condo - Pool+Spa, Beach Access, Parking

LOCATION, LOCATION, LOCATION! Discover ultimate comfort in our newly remodeled condo with a full kitchen, in-unit laundry, and a private lanai boasting breathtaking ocean views. Enjoy resort-style amenities, including 2 sparkling pools, 2 relaxing spas, and lush tropical gardens. Just a short walk to premier shopping, dining, and the beautiful Kamaole II Beach. Your endless summer adventure awaits—book your stay today!

Guest favorite

Condo

4.99 out of 5 average rating, 216 reviews

“Paradise Views” Menehune Shores, Kihei, Maui

OCEANFRONT with UNOBSTRUCTED VIEWS of Stunning Sunsets, Gorgeous Beach Shoreline, Neighboring Islands, and the Moon reflecting across the Pacific. The 112 sf covered Lanai will give you a front-row seat for viewing many water sports, activities, and whales breaching in the winter months. This is Paradise!