Vacation rentals with a pool in Hawaiian Islands

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hawaiian Islands

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

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Guest favorite

Guesthouse in Kailua-Kona

4.87 out of 5 average rating, 149 reviews

180 degree ocean view, private pool

Family friendly, NON SMOKING PROPERTY has a cottage with a 180 degree ocean view & beautiful pool. Enjoy incredible sunsets from the large deck, outdoor showers in the ginger garden & relaxing evenings in the hot tub. We welcome guests of all Races, religions, and sexual orientation! THERE IS NO LIFEGUARD ON DUTY NO DIVING IN THE POOL PLEASE THE SLIDE IS FEET FIRST ONLY! WE INVITE YOU TO PLEASE READ THROUGH THE FOLLOWING SECTION AS THERE IS OTHER PERTINENT INFORMATION FOR YOU AND YOUR FAMILY

Guest favorite

Guesthouse in Keaau

4.94 out of 5 average rating, 190 reviews

Adorable Jungle Bungalow + Pool

You awaken to birdsongs that rival the first spring on earth. A gentle rain falls, casting a silence over the cozy cabin. Do you stay in bed a little longer and soak up this soothing soundtrack of white noise? Or do you wake yourself up with a cup of Hawaiian coffee and an outdoor shower? Or maybe you start your day with a float and yoga. Whether you are looking for a quiet place to get a good night’s rest, a solo escape into nature, or a romantic getaway for your honeymoon, this is the place.

Top guest favorite

Condo in Kapaʻa

4.96 out of 5 average rating, 134 reviews

Kauai Paradise-3 hot-tubs-2Waterslides-2bdrm-3bath

Looking for the perfect Air-Conditioned condo for the ultimate Kaua'i vacation? Our premium condo offers brand new furniture & beds & huge tv's! It’s the perfect place for families to come together for an amazing vacation. Waipouli Resort has Kauai's ONLY heated soft-water relaxing river & walking pool w/ 2 water slides, 3 sand-bottom whirlpool hot tubs, 3 waterfalls & a child-friendly sandy beach & plus beautiful 3rd floor views! Plus I'll send you a list of activities, hikes, beaches & more!

Guest favorite

Condo in Princeville

4.92 out of 5 average rating, 123 reviews

Stunning Views of Paradise - Pool ~ Jacuzzi & BBQ

Spectacular Unobstructed Views - Steps away from the Resort Pool, Jacuzzi and BBQ Grills. The Furnished Patio boasts Stunning Views of the Jungle Valley, Distant Ocean Vista and Waterfalls. The Kitchen is Fully Equipped and ready for your culinary adventures. This rental is centrally located condo in the Heart of Princeville & a few minutes drive to Beautiful Beaches, Shops and Restaurants - Equipped with High Speed Internet / WiFi, Cable TV, Beach Chairs, Towels and Igloo Cooler - NO A/C

Superhost

Condo in Lahaina

5 out of 5 average rating, 4 reviews

Resort Stay Entire 1Bdr Villa Kaanapali Beachfront

This resort has the most amazing pool on the island, Salt Water Based !! So easy on the skin ;) Olympic size pool about 2.5 Acres with Slide, waterfalls , plunge pool, volleyball. Snorkel Equipment rental , Beach chairs etc. All you need to have a great Hawaiian Vacation with The Family. Awesome Luau on Site every Teus Night! This price is for scenic if avail. Otherwise upgrade is additional if oceanview is what we have for your dates:) Mahalo For coming back to The West Side Best Side!

Superhost

Apartment in Mākaha

4.84 out of 5 average rating, 195 reviews

Beach Beauty and Comfort in remote Oahu Paradise

This is among the nicest locations in all Hawaii. You are literally over a quiet, beautiful pristine beach. Beautiful valley views East. Sparsely populated beach below. Excellent sand and swimming. Beach amenities on hand. The condo is beautiful, comfortable, and nicely updated. Great local swimming, snorkeling, surfing, hiking, dolphins, turtles. Personally, I do not know a better place in Hawaii to visit if you do not need bars and shopping. Nice facility amenities below.

Guest favorite

Cottage in Hanalei

4.94 out of 5 average rating, 329 reviews

Romantic Garden Cottage,View! Pool! TVNC#1065

Escape to a secluded romantic haven nestled on an acre of lush gardens in Kauai’s breathtaking Wainiha River Valley. Perched on a bluff with panoramic valley views, this retreat offers tranquility and luxury. Unwind by your private pool and spa, surrounded by vibrant tropical flora, where nature creates an atmosphere of enchantment. Just a short drive away, explore some of the world’s most stunning beaches. Let this serene paradise immerse you in romance and blissful relaxation

Superhost

Condo in Lahaina

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!

Superhost

Condo in Kihei

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.

Guest favorite

Condo in Princeville

4.96 out of 5 average rating, 156 reviews

Beautiful studio in a top resort( pool,jacuzzi,AC)

This very comfortable resort provides 2Swimming pools and 2jacuzzis and Free bike rent and so on. The spacious studio has a comfortable Cal king Size bed with a private full bath. The roomy fully equipped kitchenette. We don't have a hot plate but offers you a dishwasher, Airfly,Electric Skillet, Omelet & Frittata Maker, Mini toaster oven and all kitchen stuff and there are many outdoor BBQ area. We could cook easily simple meal and BBQ.

Guest favorite

Home in Kapaʻa

4.96 out of 5 average rating, 179 reviews

Sleeping Giant Cottage with Plunge Pool TNVC 1244

We're thrilled to share our house in Kauai with you! There's a swimming pool, botanical garden-like setting, and location that's extremely convenient for exploring the island. Our plunge pool is perfect for cooling off after a day at the beach or just lounging in all day while staring at the 100 year old monkeypod tree overhead. Check-in 3:00PM * Check-out 10:00AM Our permit number is TNVC #1244.

Superhost

Condo in Lahaina

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.