Vacation rentals with a pool in Kihei

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kihei

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Kihei

4.96 out of 5 average rating, 389 reviews

Stunning ocean view, heated pool at home by Wailea

Last minute bookings 5 days before arrival, and week long stays are 10% off. Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Sep. 19 – 26

$868 CAD per night

Guest favourite

Condo in Kihei

5.0 out of 5 average rating, 136 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom are newly remodeled with maple cabinets and elegant granite counter tops. There is a very comfortable king size bed, a well-stocked kitchen, central AC, bamboo floors throughout, and a washer / dryer. The Condo is owned and maintained by Maui residents.

Mar. 27 – Apr. 3

$769 CAD per night

Guest favourite

Condo in Kihei

4.96 out of 5 average rating, 122 reviews

'E Komo Mai' ! 1 Bed/1 Bath in Tropical Gardens

Across the street from Kalepolepo Beach this 621 sqf. condo is nestled in the tropical Zen gardens of Kihei Resort and features a spacious lanai. The one-bedroom unit was completely renovated and has all amenities including a Queen bed in the bedroom and a futon sleeper in the living room, fully equipped kitchen, WiFi, Samsung Smart TV, keyless entry, indoor laundry, designated parking, beach equipment (chairs, towels, toys, Snorkel gear) Pool and Hot Tub. 10% DISCOUNT for stays 7+ days.

Mar. 19 – 26

$358 CAD per night

Guest favourite

Condo in Kihei

4.93 out of 5 average rating, 139 reviews

1-Bedroom Tropical Getaway, Kihei Bay Vista

You home away from home in Maui! Kihei Bay Vista is steps away from white sand beaches while still conveniently located near shops, restaurants, and transportation; 5 mins. in any direction. This 1-bdrm unit is a newly converted rental and shows pride of ownership. Kihei Bay Vista is known as the choice for many returning Maui vacationers due to its quiet low key ambiance yet resort-like amenities, with pool, jacuzzi, bbq area, and private lanai for hanging out and enjoying the breeze.

May 11 – 18

$348 CAD per night

Guest favourite

Townhouse in Kihei

4.79 out of 5 average rating, 283 reviews

Kihei Bay Surf #149 / HI Taxes included in price

Kihei Bay Surf #149 is a first floor studio with patio and grass area. The unit is located across the street from the State Beach and the National Humpback Whale Sanctuary. Quiet split system A/C (no noisy window unit) 55 inch Samsung TV, DVD, Wireless and wired internet. Full Kitchen with all amenities. In addition, there is a large pool, hot tub, tennis court and gas grills in the pool area for your use. Free parking and no additional resort fees or taxes are added to your daily rate.

Oct. 8 – 15

$283 CAD per night

Guest favourite

Condo in Kihei

4.89 out of 5 average rating, 166 reviews

Barbs Beachside Bliss. Steps to 14 miles of beach!

This is it! Open May 1-4. April throu Aug Weekly discounts. About $1000 for 4 nts. Amazing! Relaxing, chill vibe, quiet, convenient, resort amenities. 80 steps to beach. Super clean and comfortable. 5* reviews, Superhost. Enjoy Hana, Crater, and Hikes in quieter times. Our cozy, spacious corner unit overlooks tropical plantings. Full kitchen. Historical Kings Pond, turtles, sunsets, and 14 miles of beach across the street. Large pool, hot tub, bbq, tennis ct. Pickleball 5 min. walk.

Jul. 23 – 30

$309 CAD per night

Superhost

Condo in Kihei

4.86 out of 5 average rating, 182 reviews

Your Island Home - KBS

LAHAINA IS CLOSED BUT MAUI IS OPEN Newly remodeled! This corner unit is conveniently located across Kalepolepo Beach Park, & the Humpback Whale Sanctuary. Ideal for couples, a small family or a group of friends. The condo has a queen bed, queen sleeper sofa, full kitchen, bath & walk-in shower. You are minutes away from restaurants, shopping & groceries. Parking is located in front of the condo, air conditioned, and free wifi. Kick back, relax & enjoy what the Valley Isle has to offer.

Jun. 18 – 25

$293 CAD per night

Guest favourite

Condo in Kihei

4.99 out of 5 average rating, 114 reviews

Romantic, Luxury Maui Getaway with Ocean View

This is a luxury 1 bedroom 2 bathroom condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our Wailea Palms condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525

Mar. 29 – Apr. 5

$734 CAD per night

Superhost

Apartment in Kihei

4.83 out of 5 average rating, 212 reviews

Quiet Studio, Great location across from beach

My place is located in sunny Kihei and only 20 minutes from the airport. The studio is right across the street from Kalepolepo Beach and the Whale Sanctuary. The studio is centrally located in Maui near many beaches, restaurants, and shopping centers which is very convenient. The famous Ululani's shaved ice along with various fruit stands are only a few minutes away. You can whale watch, paddleboard, snorkel, sight see, and enjoy the most amazing sunsets in Maui!

Apr. 15 – 22

$258 CAD per night

Superhost

Condo in Kihei

4.85 out of 5 average rating, 310 reviews

1 minute to Beach & Downtown! Remodeled XL Apt!

In Downtown Kihei AND across the street from the sand! The world famous Kihei beaches are literally at your backyard! Everything is literally within walking distance! Entire place with free parking! 1 min walking distance to beach, supermarkets, restaurants, bars, post office and also night market (last Friday night every month) ! 30 min to Lahaina, 15 min to Wailea, and 15 min to Kahului where airport, Costco, Target and Walmart is at.

Oct. 6 – 13

$372 CAD per night

Superhost

Condo in Kihei

4.83 out of 5 average rating, 138 reviews

Updated Air Conditioned Condo Steps from the Beach

We have a beautiful condo in the sleepy beachfront community of Kihei, Maui across the street from Kamaole II, one of the most incredible beaches on Maui. Our unit is full air-conditioned with a dual system, even though you may find you don't need it because of the gentle breezes flowing through the condo. We have everything you need to make your visit something you will remember fondly for a lifetime.

Sep. 2 – 9

$343 CAD per night

Guest favourite

Condo in Kihei

4.86 out of 5 average rating, 124 reviews

Island Surf #206 Your South Maui Gem is here

Welcome to your perfect private hideaway right in the center of town. Located in the heart of South Maui with ocean views, only steps to the beach, shopping,restaurants and beautiful sunsets every night from your private patio.This is one of the most sought after locations on Maui. So don’t delay. Book today.You will NOT be disappointed!

Aug. 8 – 15

$303 CAD per night