Holiday rentals with a pool in Hawaii County

4.97 out of 5 average rating, 210 reviews

A panoramic view of a lush outdoor space features a vibrant rainbow arching over the landscape. Tropical plants surround a solar heated pool, with lounge chairs positioned nearby. The tranquil setting offers glimpses of the ocean in the background, enhancing the serene atmosphere.

Home in Captain Cook

Tiny House Hawaii

The Tiny House is ready to welcome you to a drop of heaven on the Big Island!🌴 Please be my guest for an exquisite experience in beauty, peace, and tranquility! The Tiny House is a separate guest quarters attached to the main house by only a breezeway. It has its own private entrance, covered lanai, and private yard. Everything you need for an amazing stay is included--- all cooking amenities, beach towels and chairs. The main house has a solar heated pool which is available for Tiny House guests, and a large deck with magnificant ocean and sunset views. Contact us at hitinyhouse@gmail.com for more information or to inquire about booking a stay.

A serene outdoor space features a sparkling turquoise pool and a hot tub, with a stunning sunset in the background. Comfortable seating under an umbrella is arranged nearby, surrounded by lush greenery and palm trees, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 174 reviews

Private Pool - 180° Ocean View - Minutes to Beach

WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

4.95 out of 5 average rating, 117 reviews

The modern villa features a large swimming pool reflecting the clear blue sky. A spacious outdoor area is bordered by tropical landscaping, with a combination of floor-to-ceiling glass walls and classic modernist design elements visible in the structure.

Villa in Pāhoa

Lava Flow House Pool Ocean View Kehena Beach w A/C

This luxurious modernist masterpiece with swimming pool and ocean view, sits in a serene setting in the untouched area of the Puna Coast on the Big Island of Hawaii. If you love great design and style, fantastic tropical weather, rugged yet lush landscapes, blue ocean, and relaxation, then you will love this place for your next vacation. The unique combination is a stunning contrast of rugged landscape and sharp minimalist architecture. This is a shared family home with a Main house and Studio.

Guest house in Kailua-Kona

The pool area is highlighted by a water slide and surrounded by palm trees under a colorful sunset sky. The shimmering water reflects vibrant hues, creating a serene atmosphere. Lounge chairs are positioned nearby, overlooking the expansive view of the ocean and landscape.

4.88 out of 5 average rating, 162 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

The image captures a panoramic view of a private heated swimming pool surrounded by lush greenery. Lounge chairs are positioned around the pool, and a shaded gazebo adds to the outdoor space. In the background, the vibrant blue ocean stretches under a clear sky.

4.99 out of 5 average rating, 110 reviews

Exceptional Oceanview Home - Pool & Stunning View

Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

A private solar heated pool is surrounded by tropical landscaping, featuring a waterfall cascading over black rocks. Comfortable outdoor seating is arranged nearby, with vibrant plants adding color and lushness to the serene atmosphere.

4.96 out of 5 average rating, 157 reviews

Tropical Oasis: Heated Pool, Waterfall, Ocean View

Welcome to Nakukui Hale, your own private Hawaiian sanctuary — a beautifully designed estate for up to 8 guests in a gated community. A resort-style waterfall spills over lava rock into a deep blue-tiled heated pool. Wander the lush landscape, listen to colorful birds sing, and unwind in the elevated private gazebo as the sun sets over the Pacific. Just minutes from Ali'i Drive, Magic Sands Beach, Ironman Pier and the best restaurants in Kona town. This is Hawaii living at its absolute finest.

4.88 out of 5 average rating, 190 reviews

An aerial view showcases a spacious property with a tropical style home set against a backdrop of the ocean. A manicured lawn surrounds the residence, featuring a small gated pool and a gazebo. Lush vegetation and palm trees enhance the landscape, contributing to the private atmosphere.

Home in Pepeekeo

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

The spacious home features natural wood accents, a wide balcony, and large windows that reflect the tropical landscape. Surrounding gardens with lush greenery create a serene atmosphere, while a small pond with a waterfall adds a soothing element to the exterior.

4.97 out of 5 average rating, 197 reviews

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai/Balinese architecture, hand-carved wood everywhere, and ample windows/skylights that showcase the beauty of the Big Island. The kitchen/living rooms connect to the owner's retreat via covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a quiet atmosphere and cooler temps than busy downtown while not being far from the action.

4.94 out of 5 average rating, 131 reviews

HAVEN: Poolside Sanctuary with Heavenly Views

HAVEN Where the changing colors of the heavens melt into the sea. This is a place where dreams are born and special moments unfold. Tranquility, privacy, and beauty await you. A masterclass of design in harmony with nature, this exquisite home beckons you; a salve for body and soul. Whether you are submerged in the saltwater pool or lounging inside one your deluxe bedroom suites, the views will enchant you, providing an ever-changing patina of color & light. Tax ID # TA-110-823-1680-01

5 out of 5 average rating, 229 reviews

An outdoor area features a vibrant saltwater pool with an infinity edge, set against a backdrop of lush vegetation and ocean views. A seating area with a small table and chairs is positioned adjacent to the pool, inviting relaxation while enjoying the scenery.

Guest suite in Keaau

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.

4.92 out of 5 average rating, 187 reviews

Farm stay in Papaikou

Zen Treehouse Private Retreat & Farm Stay

Retreat to a Zen-like setting in the trees; slow down and relax in this beautiful redwood octagon artist studio on a working coffee, vanilla and chocolate farm. Private lanai tucked in the treetops in a tropical rainforest setting. Stargaze from bed and wake to birdsong. De-stress, meditate, read, write, dance, create and breathe! New King bed, high quality linens, streaming TV and an awesome BedJet air cooling/warming system & more ensure the most comfortable sleep possible.

A large lap pool is surrounded by a wooden deck and tropical landscaping. Poolside loungers are positioned for relaxation, with views of the ocean and distant trees. The area is bathed in natural light, creating a serene outdoor atmosphere.