Vacation rentals with a pool in Kihei

4.98 out of 5 average rating, 121 reviews

Condo in Wailea-Makena

Grand Island Paradise on Golf Course w/Ocean Views

🌅 Enjoy sunset ocean views every night! 🏖️ <1 mile from Wailea Beach! Inside are 3 bedrooms w/ a King, Queen, 4 Twin, and 2 trundle beds! There are 2 private balconies, private laundry, and it's ground level- NO STAIRS! The complex has 2 POOLS and Parking for 2+ cars. Close to Wailea, Makena, Keawakapu! This property will be transitioning to another Superhost. If you would like to make a reservation beyond August 18th 2025, please do so via the new listing at http://airbnb.com/h/hoku-hale.

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!

4.92 out of 5 average rating, 336 reviews

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

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!"

4.97 out of 5 average rating, 114 reviews

A clear swimming pool is surrounded by palm trees and tropical foliage, providing a serene view. In the background, a shaded gazebo adds to the landscape while the ocean can be seen beyond the pool, complementing the tranquil atmosphere.

Condo in Lahaina

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

A serene outdoor area features well-maintained green grass and several lounge chairs positioned to face the ocean. A table with decorative items is visible in the foreground, while palm trees sway gently in the breeze against a clear blue sky, providing a view of the distant mountains.

Condo 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!

A private pool area features a vibrant blue swimming pool surrounded by a spacious deck. Sun loungers are positioned around the pool, inviting relaxation. Lush greenery and tropical plants frame the area, contributing to a serene outdoor environment with a communal building visible in the background.

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%.

4.83 out of 5 average rating, 146 reviews

A serene pool area is surrounded by lush tropical landscaping, with sun loungers positioned along the water's edge. Palm trees provide shade, and vibrant flowers add color to the scene. The pool's clear blue water reflects the sky, enhancing the tranquil ambiance.

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!

The image depicts a serene swimming pool surrounded by a paved deck with multiple lounge chairs. Lush palm trees sway in the gentle breeze, and the ocean can be seen in the background under a partly cloudy sky.

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.

4.98 out of 5 average rating, 184 reviews

The outdoor pool area features a large, inviting pool surrounded by palm trees and lush tropical plants. Comfortable lounge chairs are positioned around the pool deck. A small waterfall adds a serene touch to the setting, with sunny skies illuminating the landscape.

Condo in Lahaina

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.

A large swimming pool is surrounded by palm trees, with clear blue water under a partly cloudy sky. A hot tub is situated on the left, and a green bridge spans the pool area, connecting both sides. Lush landscaping enhances the tranquil setting.

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.

A clear blue pool is surrounded by tropical landscaping and palm trees, offering a relaxing atmosphere. A heated spa is located adjacent to the pool, with steps leading into both water areas. A bridge crosses over part of the pool, adding to the scenic view.

4.87 out of 5 average rating, 108 reviews

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.

A spacious community pool area is surrounded by tropical landscaping and palm trees. The inviting blue water of the pool spans a large area, complemented by a sun deck with lounge chairs. A well-maintained pool house features large windows and essential amenities.