Holiday rentals with a pool in Kaunakakai

4.95 out of 5 average rating, 102 reviews

Cottage in Molokai

Oceanfront 2-Bedroom Cottage, Stunning Views, Pool

Enjoy stunning sunset views of the Pacific Ocean, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, oceanfront cottage with a large covered lanai. This No Smoking two-Level cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore or just unplug and relax. You will experience colorful sunsets, breezes, tropical birds, beaches, and breaching whales in the winter.

4.93 out of 5 average rating, 120 reviews

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!

Top guest favourite

4.97 out of 5 average rating, 114 reviews

60%OFF APRIL-JUNE/25! Ocean views! Air Conditioned

Thank you for checking us out! We have dropped our price 60% for the month of April 2025 to end of June 2025. They are doing re-piping to the building adjacent to us and there will be construction noise Monday to Friday 9:00am to 4:30pm. NO work to be done evenings, weekends or holidays. You must acknowledge this at time of booking. Most people are at the beach, pool or touring the island during the day so this might be an opportunity for you to stay in an amazing condo for a great price!!!

4.89 out of 5 average rating, 120 reviews

Apartment in Wailuku

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!

4.82 out of 5 average rating, 131 reviews

Cozy 2 Bedroom Condo with pool near beach

Popular Vacation Rental near Kihei's best beaches! This highly sought after 2 bedroom, 1 bath corner unit at Kalama Terrace is close to Charley Young, Kamaole One, and The Cove beach parks. Located on the top floor, you'll enjoy ocean, Lanai and West Maui Mountain views. This condo is perfect for couples and families with a comfortable King bed and a Queen bed. note: The nightly pricing includes taxes like General Excise Tax 0f 4.712% and Transient Accommodations Tax of 10.25%.

4.82 out of 5 average rating, 162 reviews

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!

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.

4.71 out of 5 average rating, 173 reviews

Apartment in Kaunakakai

*VEHICLE INCLUDED! Wavecrest Resort EAST MOLOKAI

TA-075-407-5648-01 THIS UNIT COMES WITH THE ABILITY TO USE OF AN SUV...... UPDATE!!!! We now have dedicated internet!!!!No more bad resort Wi-Fi!!! This unit is located on the island of Molokai. After years as a long term rental, my cozy,semi-private location at Wavecrest Resort is a vacation rental again. Often described as a home away from home this unit will bring a warm feeling to your heart and soul.

Top guest favourite

4.98 out of 5 average rating, 184 reviews

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

A legal short term rental! 1 bedroom, 1 bath with open floor plan. This condominium has a comfortable Cal-King bed in the bedroom and sofa sleeper in the living-room. **Central A/C*Fully equipped kitchen w/ granite counters*refrigerator*stove top + oven*coffee maker* microwave* dishwasher* washer/dryer* Free in room WiFi** Onsite gym is managed by an outside contractor and charges $9/day for useage.

4.86 out of 5 average rating, 102 reviews

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.

4.92 out of 5 average rating, 175 reviews

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.