Holiday rentals with a pool in Wailea, Wailea-Makena

Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops

Location and Quality! You will feel the relaxed beach vibes from the very first step walking into this tastefully updated & beach luxe unit. Directly sit across the famous Cove surf spot & in the middle of all, you will be memorized by the ocean waves along with surfers, paddlers and the breathtaking sunset views, and the incredible walk distance to everything Kihei has to offer including activities, shopping, dining, nightlife and more! Experience the best of Maui from our Luxe-design condo!

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

Oceanfront Condo with Pool and Jacuzzi

Relax in this peaceful gem on Maui. Located on the ground floor, you can walk into the ocean from your back porch. You'll see Turtles on our little secluded beach, amazing sunrises and sunsets over Maalaea Bay, and Whales during whale season! Maalaea Banyan is the only property in the area that includes a pool and jacuzzi. Just 1/4 mile away is Maalaea Harbor featuring snorkel, SCUBA, and sunset boat trips, the world famous Maui Ocean Center aquarium, restaurants and gift shops!

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!

Whale Season Special! T-046-692-0448-02

We love to host! Listing was paused to help fire families! Read our 5*reviews! Directly across from a State Beach Park with morning sea turtles and the best Maui Sunsets. Food Trucks,Grocery store, Badass coffee, Miso Phat Sushi all in walking distance and give it a neighborhood feel. Onsite BBQ, Newly Updated Pool and Free Parking! 10 min to Kaanapali / Napili. Beach towels/Chairs provided. Clean, comfortable unit with lots of privacy and a great local vibe!

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.

Top Floor Stunner! Highly Upgraded! Summer Special

"The Kaleialoha" #414 Maui is open and ready for your arrival! Please come help us rebuild our community! This TOP FLOOR unit has unobstructed Ocean and outer island Views! This beautiful completely remodeled unit will take your breath away! New AC unit in living area! New High end sofa sleeper in living room! Cal King Bed and second TV in bedroom. Bosch Washer and dryer in unit.

Koa Resort Unit 5C - 1 BR Garden View

Back on Airbnb after 1 year rental by fire displaced Lahaina resident 1 Bedroom Garden view, ground floor condo on 5.5 acres across from beach in central Kihei. Close to all of the Kihei beaches, restaurants, shopping. Short drive to Wailea, Makena, Sugar Beach. Unit is 750 sq ft, with air conditioner in the bedroom and a 200 sq ft lanai with outdoor dining area.

Tropical Paradise Close to Everything

Aloha Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Located on 5 acres of lush tropical grounds, with open grassy spaces and private walk paths, one of the only heated pools on Maui, private tennis courts, bocci ball court, ping pong, and the ocean directly across the street, Koa Resort is a private oasis in central Kihei.