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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in Lahaina

4.98 out of 5 average rating, 130 reviews

Modern + Serene Oceanfront Napili Getaway w/ AC

Welcome to Napili Point! This oceanfront 1 bedroom directly on the stunning Honokeana bay is a relaxed, contemporary space designed to create special memories in a stylish, comfortable environment. Fully remodeled, this air conditioned property is surrounded by water with quick access to Napili bay beach (one of the Maui's favorite beaches), and there are no hidden resort or parking fees! This condo is perfect for couples, small families, or anyone looking for a great base to explore the island.

Aug 15 – 22

G$68,937 GYD per night

Guest favorite

Condo in Koloa

4.98 out of 5 average rating, 232 reviews

Slice of Kiahuna Paradise-A/C-BEACHFRONT-POOL

Remodeled bright & breezy top floor, corner unit in exclusive Bld 23. Steps away from top rated Poipu Beach. View. Whole home A/C (dual split in living room & window unit in bedroom). Super fast Wifi. New master bed & queen sleeper sofa in the living room comfortably sleeps up to 4 people. New living & dining furniture and appliances. 65” Smart tv. Unit is supplied w/extra amenities, suggested experiences & babysitting recommendations around the island to offer a fantastic & unforgettable stay!

Mar 9 – 16

G$108,115 GYD per night

Guest favorite

Condo in Kihei

4.9 out of 5 average rating, 298 reviews

Everything you need to enjoy true paradise!

After spending a month in Kihei, we didn't want to leave... we also wanted a place to invite other people to island living! Welcome to our Hawaii oasis. Steps away from food, drinks, the pool and the beach, what more could you ask for? Central to downtown Kihei and Wailea, it's the perfect location to explore Maui from. Walking distance to perfect sunsets, amazing eats, and Kihei's finest beaches our unit is tucked at the end of the cul de sac - serene, quiet, and away from any street noise.

Nov 23 – 30

G$65,460 GYD per night

Superhost

Condo in Honolulu

4.92 out of 5 average rating, 123 reviews

2BR 2BATH Oceanfront Family Home with Free Parking

Newly remodeled and refurbished home <5min from beach! This superb two bedroom offers city views and palm trees through large, panoramic glass panels and sliding glass doors. The master bedroom has a luxurious king size bed. The second bedroom is equipped with two ultra comfortable double beds and a sliding wall that closes off for ultimate privacy. A queen sized sofa bed graces the living room. We have in-unit washer/dryer, pack-n-play and high chair to make your stay as easy as possible.

Oct 28 – Nov 4

G$141,589 GYD per night

Guest favorite

Condo in Princeville

4.89 out of 5 average rating, 265 reviews

Airy Apt w/AC: Walk to Beach, King Bed, Pool

Situated in beautiful gardens between Anini Beach and Princeville Center, along bike paths and a golf course, this open, airy apartment is the perfect escape. From the second-story lanai, you will be treated to lush mountain views. Cook delicious meals in your air conditioned kitchen and take a short walk to snorkel at Anini Beach. Head ten minutes into Hanalei for all levels of surfing, from lessons to world class breaks. Enjoy happy hour at the Happy Talk at sunset for a one-of-a-kind view.

Apr 10 – 17

G$74,300 GYD per night

Guest favorite

Home in Pepeekeo

4.87 out of 5 average rating, 150 reviews

Hamakua Coast Tropical Home

A beautiful tropical style custom home featuring private ocean views and a small gated pool. Our home was thoughtfully designed to maximize Hawaiian indoor/outdoor living and entertaining in a manicured park-like setting. A palm lined driveway leads you to a single level 3 bedroom, 2 1/2 bath residence located in the exclusive Pepeekeo Point subdivision, approx. 15 minutes from Hilo. Featuring a fiberglass pool with a bamboo pavilion& bbq for outdoor dining No parties or unregistered guests

Oct 25 – Nov 1

G$87,059 GYD per night

Guest favorite

Guesthouse in Koloa

4.99 out of 5 average rating, 147 reviews

Poipu Tropical Retreat with AC & Pool/Gym Access

Discover beautiful Kauai from this spacious 1 bedroom vacation home, built in 2018, in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai, shops and restaurants. Create lifetime memories from this modern retreat with its tropical Asian decor. This is a stand alone house, very private, not an apartment. Enjoy a complimentary Poipu Beach Athletic Club membership.

Dec 23 – 30

G$134,684 GYD per night

Guest favorite

Guest suite in Keaau

5.0 out of 5 average rating, 122 reviews

Oceanfront! Spectacular 2BR/2BA w Pool & Hot Tub

Location Location Location!! You will absolutely love our beautiful oceanfront Harmony House Hawaii on the lush east side of Hawaii Island. Imagine sitting on your lanai overlooking the infinity edge saltwater pool, hot tub and Zen Garden, watching & hearing the ocean waves dramatically crash on to the rugged lava cliffs. Walk through the rear gate & stroll on the popular Beach Road walking path or take out camp chairs to just sit & enjoy the stunning view. Whale watching Dec - Mar.

Sep 19 – 26

G$81,651 GYD per night

Superhost

Condo in Princeville

4.78 out of 5 average rating, 212 reviews

BOHO Paradise Resort w/Pools, Hot Tubs, Kitchen!

Enjoy our 22-acre resort on Kauai’s romantic North Shore! Just 10 minutes from world-famous Hanalei Bay and tropical beaches, the resort offers two swimming pools with waterfalls, hot tubs, putting green, a gym, tennis courts, grills, and on-site bike rentals. Our beautiful garden studio has a fully-equipped kitchen and steps into a lush garden lanai full of tropical fruits and exotic birds. End the day on the cliff, watching whales and sunsets over the ocean with breathtaking views!

Apr 22 – 29

G$54,467 GYD per night

Guest favorite

Condo in Koloa

4.92 out of 5 average rating, 104 reviews

Poipu Beach Paradise Entire 1 Bedroom Condo

Welcome to Kauai and the beach town of Poipu! Your stay at our well appointed modern beach inspired condo will be a wonderful place for your Hawaiian vacation. Just a short 5 min walk to Poipu's beaches for activities ranging from leisurely strolls and sun bathing to surfing and snorkeling your access to the sun, beach and surf is right out the door. We look forward to spreading the Aloha spirit with you during your stay on the sunny side of Kauai! Mahalo, GP Family TA149523507201

Oct 26 – Nov 2

G$80,158 GYD per night

Guest favorite

Condo in Kihei

4.99 out of 5 average rating, 144 reviews

Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!

Mana Kai 608 is a remodeled oceanfront 2b/2b condo DIRECTLY on Keawakapu beach! This location is ideal, on the border of Wailea and Kihei. We have designed our remodel with a modern surf vibe in mind, we are excited to share it with you! If you enjoy Wailea's 5-star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach come stay with us! We have hired the best Property Manager in Maui, Tracy O'Reilly to take care of our guests.

Sep 2 – 9

G$166,902 GYD per night

Guest favorite

Home in Captain Cook

4.96 out of 5 average rating, 148 reviews

Milolii Whale House With Ocean Views and Pool!

The Whale House is a great home to watch the whales migrate down the Kona Coast in season! The house has 3 private bedrooms and 2 1/2 baths on two levels. The upper (primary level) includes a full service kitchen, two master bedrooms and 1 & 1/2 bathrooms. The lower living area is separate from the main living space, is handicap accessible (See Accessibility Notes) and has a private master bedroom and master bath. The house is perfect for couples or families.

Jan 8 – 15

G$72,290 GYD per night