
Vacation rentals with a pool in Captain Cook
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Captain Cook
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

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, and ample windows and 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 cooler temps than busy downtown while not being far from the action. Solar/Tesla batteries keep power on!

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

Reefside Suite at Seaspray Ocean View
Treat yourself to a fabulous ocean view suite. A great place to start your day of adventures on the Big Island. Come home to a dip in the pool and a relaxing night with the sound of waves from Kahaluu Beach Park. Prepare a meal in this fantastic new kitchen with fusion granite that looks like artwork. Enjoy the beach, snorkeling and surfing just across the street or just relax from your lanai & watch surfers catch the waves. YOU'RE COMING TO HAWAII,,,, Choose the Reefside Suite w/Ocean views.

Aloha Paradise! Remodeled with A/C & Ocean View!
Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

Longboard Studio at Kona Magic Sands Beach
Welcome to LongBoard Studio – Kona’s premier direct oceanfront escape at Magic Sands Beach! This stylish, film-featured studio offers stunning ocean views, a brand-new lanai with teak furniture, and full-width NanaWall doors for seamless indoor-outdoor living. Enjoy a gourmet kitchen, AC, queen bed, in-unit laundry, and the sound of waves at your doorstep. Perfect for relaxing, writing, or watching dolphins & whales from your lanai. Steps to the beach, serenity, and aloha! TA-005-037-8752-01

Kona Ocean-View Retreat | Pool, Sunsets & Aloha
Wake up to sweeping ocean views, coffee in hand on your private lanai, with nothing on the agenda but deciding which beach to hit first. This beautifully styled ground-floor suite in Kailua-Kona is your personal slice of Hawaii — breezy, bright, and designed for guests who want comfort without compromise. Rated 4.98 stars by 166 guests, this is a top 5% Airbnb home on the Big Island — and guests keep coming back for the views, the beds, and the aloha spirit Tracy and JD bring to every stay.

Kona Paradise with Oceanfront views!
Fall in love with this bright and beautiful End Unit across from Surfers Paradise, ocean access to Lymans Bay, oceanfront complex. Dedicated parking spot in front of unit, first floor, private Lanai with amazing views of the surrounding hills, located on the famous Alii Drive directly across from Ocean. Under 1 mile and walkable to Magic Sands Beach, steps away to Banyans popular surf spot and Da Poke Shack! Just outside the heart of DT Kona & access to all parts of the Big Island.

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

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC
Bringing the whole crew—or two families? This breezy 4BR, 3BA Kona home is built for fun and flexibility. Two stories mean plenty of space to gather—or sneak off for quiet time. With two kitchens, two living rooms, A/C, smart TVs, and indoor laundry, everyone gets room to relax. Take in an almost 180° ocean view of Kona bay, lounge on breezy lanais, fire up the BBQ, or float in the pool. Pick fresh mangoes and starfruit on-site. Just 5 mins to Kona town—your perfect island escape awaits.

Suite Magic Sands Beach
Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

Pineapple Palace~Stunning Ocean Views~Private Pool
The Pineapple Palace is located on one acre in the quiet rural area of Milolii. The home is near City of Refuge, Punalu'u Bakery, South Point, Pu'uhonua O' Honaunau, The Coffee Belt, and is on the way to Volcanoes National Park. You’ll love my place because of the comfy beds, the high ceilings, the views, the Private Pool, the well stocked kitchen. My place is good for families (with kids) and big groups. NEW FIBER OPTIC HIGH SPEED INTERNET 600 MBPS INSTALLED APRIL 2024.
Popular amenities for Captain Cook rentals with a pool
House rentals with a pool

Romantic Keauhou Retreat | Pool + Tropical Lanai!

Kahaluu Bay Get-Away

Tropical Oasis Home with Pool and Steps to Beach

Pool, 6 mins to Beach, Ocean View, H7

Walua Oasis 2/2 Private Pool

Big Island Koi Hale

Panoramic Ocean Views With Private Saltwater Pool

Tranquil Hawaiian Pineapple Poolhouse with A/C
Condo rentals with a pool

Discounted A35 Kona Reef Oceanfront AC Park Free

Absolute Oceanfront Property

Inna's Downtown-Walk to Beach and to Supermarket!

Kona 1BR Condo w/ Pool, Office, Walk to Beach

Ali'i Dr w/ Ocean Sunsets next to Farmer's Market

Peaceful Keauhou Condo. A/C. All Taxes included.

Royal Kahili Condo with Lanai Ocean View

2 Bedroom Penthouse Condo With Ocean View And Pool
Other vacation rentals with a pool

Modern Bungalow • AC • Walk to the Ocean

Best ocean view deal! Owner managed! 5 star stay!

Beautiful Modern Ocean Front Condo

Cozy jungle 2-bedroom cabin (TA-154-746-2656-01)

Kona Mansion Infinity Pool & Ocean Views (Hosted)

Brand NEW Oceanfront Retreat! Steps to Beach!

Stunning Oceanfront Beach Condo!

Luxury Ohana, 60ft Salt Pool,
Quick stats about vacation rentals with a pool in Captain Cook

Total vacation rentals
Explore 10 vacation rentals in Captain Cook

Nightly prices starting at
Captain Cook vacation rentals start at ﺩ.ﺇ588 per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Wi-Fi availability
10 of Captain Cook vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Captain Cook rentals

4.8 Average rating
Captain Cook stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with pools Hawaii County
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- Hapuna Beach
- Waikoloa Beach
- Waikōloa Beach
- Mauna Lani Beach Club
- Mauna Kea
- Makalawena
- Manini'owali Beach
- Spencer Beach Park
- Puʻuhonua o Hōnaunau National Historical Park
- Kilauea
- Big Island Retreat
- Kaloko-Honokohau Nat'l Hist Park
- Waialea Beach
- Papakōlea Beach
- Sea Village
- Punaluu Black Sand Beach
- Kona Farmer's Market
- Kua Bay
- Magic Sands Beach Park
- Volcano House
- 49 Black Sand Beach
- Kilauea Lodge Restaurant
- Hapuna Beach State Recreation Area
- Green Sand Beach





