Beachfront vacation rentals in Wailea Beach

4.96 out of 5 average rating, 182 reviews

Spectacular ocean views @IslandSurf Aug Spec. $149

*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 RESTAURANT

4.98 out of 5 average rating, 157 reviews

Ocean view and beach by Wailea

Infants and children welcome! Ocean views, beach across the street. Large lanai. Indoor and outdoor dining. Large bedroom, king bed, ensuite, east facing second lanai off bedroom. Guest bathroom living room. Double height single air mattress, pac n play, high chair. Comfortable and quiet split system A/C. Toys, beach wagon, umbrellas, beach chairs, boogie boards, beach towels provided. Close to shops and restaurants. Tennis courts and two pools in complex. Reserved parking by front door.

4.99 out of 5 average rating, 196 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in an ideal location, right on the border of Wailea and Kihei! Our condo is designed 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, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

4.96 out of 5 average rating, 122 reviews

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

Hale Kamaole: Remodel to be completed Nov 2025. Romantic Bright & Airy Beach Condo Across Street from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for 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

4.99 out of 5 average rating, 117 reviews

Wailea Ekahi Oceanview, Beachfront King Bed Studio

Wailea Ekahi is a luxurious beach front resort offering the best of Maui and sunny Wailea. Unit 16B is a renovated ocean view studio unit with a King sized bed and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens. The resort fronts directly onto Keawakapu beach with miles of golden sand; perfect for walking, swimming and snorkeling. 16B is mid property and a short walk to the beach and one of the 4 pools.

4.8 out of 5 average rating, 287 reviews

Apartment in Kihei

*Last Minute Deal* Oceanview Full Remodel New Ac!

Centrally located in sunny Kihei, Waiohuli Beach Hale is a tranquil, tropical paradise. You will instantly fall in love with this well maintained, two story complex. Featuring lush landscaping, fruit trees, amazing ocean views, water features, a large heated lap pool and a quiet, relaxed atmosphere, this is the perfect oasis for your time on Maui. Located on one of the longest stretches of beachfront here on Maui, Waiohuli Beach Hale is the perfect complex for beach combers and snorkelers.

4.97 out of 5 average rating, 126 reviews

NEW Ocean View 1 Bedroom Condo with Common Hot Tub

Designed as our personal 2nd home, this beautifully furnished and decorated condo features high-end appliances. Your 5th-floor unit offers an unobstructed ocean view—no sidewalks, power lines, or parking lots in sight. Enjoy tennis, pickleball, pool, BBQ area, putting green, hot tub, and direct beach access—just steps away! The free parking lot is out-of-eyesight. 17.5% TA Tax is included. Sunsets are magical from your lanai. Both your living room & bedroom boast breathtaking ocean views.

4.99 out of 5 average rating, 222 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.

5 out of 5 average rating, 172 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.

4.96 out of 5 average rating, 134 reviews

Apartment in Kihei

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.

4.87 out of 5 average rating, 414 reviews

Can be 2 Units! Modern On Beach Ocean View Balcony

You get BOTH units. Free Parking. World famous Sugar Beach is in the backyard w/ 10 miles of sand. Fully Remodeled. This single property works like two connecting hotel rooms. It can split into TWO units simply by locking the bedroom door. One unit would be a hotel room with bath. The other unit would be a hotel room with bath + kitchen. The property has TWO entrance doors, TWO FULL BATH with Tubs, TWO KING BEDS, TWO AC's, and TWO TV's. The The property also has free parking!