Family-friendly vacation rentals 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.

Kitchen · Indoor spaces · Pool

Family Oceanview | Pool + Hot Tub | Private Lanai

Make family memories in this top-floor ocean-view condo in Kihei. Enjoy Pacific views, ocean breezes, year-round sunsets, and seasonal whale watching from the private lanai. Just steps away, the beach across the street is ideal for morning walks, beachcombing, dipping your feet in the water, and sunset strolls. The shallow, rocky shoreline is not ideal for swimming, but some of South Maui’s favorite swimming beaches are just a short drive away. A comfortable home base for Maui adventures nearby.

Family · Indoor spaces · Grill

Groovy bright condo 2 bed / 2 bath South Kihei

Enjoy our home away from home! Bright Groovy Beach Condo offers you a naturally lit and engaging space to relax with two bedrooms each with their own en suite bathrooms (4th bed is the pull out sofa bed in the living room). Enjoy your morning coffee on the lanai and listen to the birds. Haleakala Shores is located 300 meters from world famous Kamaole Beach III. You are also located within a casual stroll (or snorkel or paddle board) north to Kamaole Beach II, I and finally Charley Young Beach.

Indoor spaces · Kitchen · Accuracy

Sweeping Panoramic Ocean Views - Private Ohana

Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

Family · Kitchen · Sleep quality

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 the ideal location, on the border of Wailea and Kihei. Our condo is designed with a modern surf feel in mind, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, 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 PM in Maui, Tracy O'Reilly to take amazing care of you!

Family · Kitchen · Laundry

Lovely Oceanfront Condo with pool

Discover Paradise: Lovely Oceanfront Condo with Pool & Unforgettable Views Wake up to the symphony of waves and endless blue horizons in this stunning oceanfront condo, your ideal escape for relaxation, romance, or family adventures. Nestled right on the edge of the beach, this beautifully appointed retreat offers breathtaking panoramic ocean views from your private balcony—perfect for sipping morning coffee as the sun rises over the water or unwinding with a glass of wine at sunset.

Kitchen · Family · Bathroom

Very Comfortable Kamaole Sands Condo Sleeps 4

Very comfortable end unit 1 bedroom condo 2 bathrooms (818 sq ft) with views of the pool, partial ocean view, remodeled kitchen and bathrooms, recently painted, new flooring in living room and conveniently located to everything you need, unit is airy and bright with extra windows. The kitchen is well stocked with all the essentials and cooking utensils. A 5 mins walk to the beach and 10-15 mins leisurely stroll to nearby shops and stores. I take my own photos for my unit.

Family · Indoor spaces · Access

Kihei Condo: Steps from Beach & Yummy Eats!

✨ Your Maui Escape Awaits! 🌺 Nestled in the heart of Kihei, our condo is just steps from Kamaole Beach Park—famous for golden sands, calm waters, and stunning sunsets. Stroll to local shops, food trucks, and restaurants, or unwind on your private lanai in true island comfort. With a central location near Haleakalā, the Road to Hana, and Twin Falls (waterfalls), this tranquil retreat is the perfect home base to savor all of Maui’s beauty, flavor, and adventure. 🌴☀️

Family · Kitchen · Long stay

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.

Indoor spaces · Family · Nearby

15 Steps to Beach! 2 Bedroom w/XL Kitchen & Pool!

The orange dot on the cover photo is the wall of the unit! It is literally 15 Steps from your door to the sand! World famous Sugar Beach of 10 miles of pristine beach. Beach side condo with full amenity. Next door to bar/restaurant. Walking distance to bus stop, bakery, ABC store and world famous shave ice! The place is very central. 30 min to Lahaina, 15 min to Wailea, and 15 min to Kahului where airport, Costco, Target and Walmart is at.

Indoor spaces · Kitchen · Hiking

3BR spacious Condo with Ocean View in top location

Enjoy ocean views and island living from this spacious 1,400 sq ft 3-bed/2-bath condo in the heart of Kihei. Located directly across the street from the beach, you can watch whales from the lanai or relax by the pool and BBQ area. Shores of Maui offers easy access to Kihei’s best beaches, shops, and restaurants, all within minutes. A perfect home base for families and groups looking for comfort, convenience, and the South Maui lifestyle.

Kitchen · Family · Backyard

Whales and sunsets, front row seats every day!

Charming three-bedroom home offers a private, "local" experience in one of Maui's rare oceanfront neighborhoods. Our charming and cozy home is complete with all you need and will make your transition from daily life into a vacation as seamless as possible. GE and TA taxes will be added after booking. Cleaning fee of $575. Amy Russell, reservations manager, and Jordan McEntire, property manager.

Indoor spaces · Kitchen · Checkout