Family-friendly vacation rentals in Wailea, Wailea-Makena

4.89 out of 5 average rating, 132 reviews

Incomparable Maui Sunset condo, includes all taxes

This Renovated, beach themed condo in the Oceanside Maui Sunset is shaded from the afternoon sun on the B side. Our rate includes the 19% state tax! 2 full bathrooms, a new 75" TV, stove, dwasher quartz counters and new thick futon mattresses. The view from the lanai is over the resort's beautiful grounds (with largest private pool in Kihei) to the ocean. Good architecture and concrete construction keep units in this well managed complex private and safe. High speed internet (196Mbps).

4.86 out of 5 average rating, 126 reviews

Ocean front property- Sugar Beach!13531117

No lobbies to walk thru. Safer, disinfectants at hand. Great outdoor areas, a few step walkway to beautiful sugar beach . 1 easy flight up or elevator.Blackout drapes. Fun fancy dishes large oven. Easy walk 2 bakery /farmers mkt, ABC store,shave ice. 20 min fr airport, close to bus stop. quieter side of Kihei. packnplay, 2TVs,a/c SPECIAL SPORTS PKG. king bed,queen futon,twin air mattress,2 bathrooms!NO SMOKING ON PROPTY.Cook inside, BBQ outside and lovely tables to eat out n lighted area.

4.68 out of 5 average rating, 101 reviews

Kamaole Beach Condo SALE$165 5/9-13, 22-27 Jun$180

Just 3min walk to Kamole Beach, & swim with turtles! This gorgeous fully equipped, completely remodeled condo features new Split Unit A/C in bedroom and living room, King-size bed, Queen convertible couch, Queen air bed, Ultra speed Wifi, large fully stocked Gourmet Kitchen with nonstick pans, coffee maker, toaster, blender, Vizio 65” smart TV for streaming, Washer/Dryer, Pool, Hot tub, Sauna, BBQ grills, Pickle ball, Shuffle board, Tennis courts, walk to shopping, restaurants, & activities.

4.83 out of 5 average rating, 146 reviews

Condo in Wailea

Beautiful Palms At Wailea #608-April/May Discount

Beautiful Palms At Wailea ,2BR/2BA,Condo, located in the heart of Wailea. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

4.91 out of 5 average rating, 209 reviews

Condo in Wailuku

Rare Beachfront Ground floor Oceanview from Lanai!

Enjoy a Romantic yet affordable Direct BeachFront, Ground floor condo with a partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea- the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April) and turtles are often seen in the waters. On a a quiet, non-through road, this is like your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

4.7 out of 5 average rating, 265 reviews

Oceanview Surfrider

Scenic unobstructed sea views, steps away from the pool. Remodeled August 2021. We are across the street from Cove Beach and Kalama Park. Ideal location for paddleboarders, beginner surfers, wave rider rentals next door. Convenient short blocks to restaurants, bars and entertainment, Foodland and convenience market. New sofa and queen mattress July 2022. King Cool Gel Bed. There is no dedicated work space. Island in the kitchen with 3 stools.

4.94 out of 5 average rating, 120 reviews

Family Friendly Condo! Best Location!

Escape to Maui! Family Friendly Condo with Discounted Rates - Book your Tropical Getaway Now! Spacious, walkable Kihei condo that sleeps 6 - with parking, pack n play, and tons of kid friendly gear! Due to last minute cancellations, we are offering a HUGE DISCOUNT off our normal rates for our family friendly 2-bedroom, 2-bathroom (2 bathtubs) beach condo. If you are looking for the perfect place for your family to call home in Maui, this is it!

4.83 out of 5 average rating, 159 reviews

Awesome Maui home away from home. Includes taxes!

A/C throughout. Work desk with dependable wi-fi. 2 Cable TVs . Grass area off lanai. Walk to the beach, stores, restaurants, the park or bus stop. Full kitchen, W/D, 2 queen beds and 1 queen sofabed, 4 beach chairs, 4 beach towels, a beach umbrella and travel cooler, Pak-n-Play, Booster Seat, 2 pking spaces. This condo is comfortable and well-eqipped for a wonderful stay and vacation on Maui. New pool and jacuzzi.

4.83 out of 5 average rating, 172 reviews

Spectacular Direct Ocean Front location!

Spectacular oceanfront location only steps away from the beach! This stunning space provides everything a Maui vacation should offer. Positioned right on the water, this quaint condo offers direct ocean views and access along with a dreamy sight of the West Maui mountains. Wake up in paradise to the sound of the ocean waves crashing right outside your door!

4.79 out of 5 average rating, 160 reviews

Apartment in Kihei

Beautiful Remodel Great Value Book Now!

This beautiful remodeled Two-bedroom/One bath condo is only 126 steps from the beach!! Enjoy beautiful sunsets and long walks on miles of beautiful beach! Watch the whales in the bay and enjoy snorkeling, swimming and boarding. This spot is a well kept secret - close to shopping and dining spots!

4.84 out of 5 average rating, 164 reviews

Maui Kamaole Kihei Wailea Direct Ocean View

Located at the beautiful Maui Kamaole complex in the front row full ocean view " G" building right across the street from Kam 111 beach. All new beds, mattresses, towels etc. See whales from the lanai ! Convenient parking right in front of unit. Price includes occupancy tax .