
Holiday rentals with a pool in Kailua-Kona
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Kailua-Kona

Total holiday rentals
Explore 2,070 holiday rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona holiday rentals start at $72 AUD per night before taxes and fees

Verified guest reviews
Over 78,370 verified reviews to help you choose

Family-friendly holiday rentals
980 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 80 rentals that welcome pets

Rentals with dedicated workspaces
1,090 properties have a dedicated workspace

Wi-Fi availability
2,070 of Kailua-Kona holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kailua-Kona rentals

4.8 Average rating
Kailua-Kona stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Kailua-Kona
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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

Ocean, Sunset, Mountain & Celestial Views
🌴 Guest Favorite - Top 10% on the Big Island Enjoy stunning ocean, mountain, sunset, and starry views from nearly every room in this cozy, family-friendly three-bedroom, two-bathroom Waikoloa Village, Hawaii home. The house includes everything you'll need on your paradise escape including a fully equipped kitchen, beach gear such as boogie boards, snorkels, coolers, umbrellas, towels and Wi-Fi. We also provide bath towels, bed linens, soaps/shampoos, coffee, children's toys, and a BBQ grill.

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

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.

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.

Million Dollar View | Sunsets & Aloha
"The photos don't do this view justice!" That is the most common guest comment. 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. Wake up to sweeping ocean views with nothing on the agenda but deciding which beach to visit. This beautiful ground-floor suite in Kailua-Kona is your personal slice of Hawaii — breezy, bright, and designed for guests who want comfort without compromise.

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.

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

Discounted A35 Kona Reef Oceanfront AC Park Free
The Kona Reef is being renovated in 2026. Check out our special construction rates. Reno hours 8a-5p Mon-Sat while you are out at the beaches, volcano etc. You’ll love this condo! Absolute Ocean Front. 5 minute walk to downtown. Free parking! Completely remodeled! Fresh, clean, stylish & comfortable. NEW Full A/C, Stocked Kitchen & Beach & Golf Equipment. ATTENTION GOLFERS! 2 sets of Callaway Clubs! Check out our 2 other Kona Reef condos D33 & B31 TA-109-938-6880-01 STVR-19-352037

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.

Oceanfront Gem, Walk to Beach/Town, AC, Elevator
Right-on-the-ocean, newly renovated, spacious, upscale condo in a gated boutique complex. Unbelievable views from the lanai, living room and bedroom. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and shops in Kailua Village. New king bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Heated, ocean-front salt water pool with outdoor shower and community BBQ. Quiet; no noise from Ali'i Drive. Reserved parking spot. A/C. Elevator.

Updated condo with ocean views & air conditioning
Kick back and relax at this renovated condo with partial ocean views, an oceanfront saltwater pool, and lusciously landscaped grounds. This air-conditioned unit boasts a central location just 1.3 miles from the heart of downtown Kona. Conveniently located between downtown Kona and the world-famous Magic Sands beach, this is the perfect home base to explore everything Hawaii Island has to offer. Enjoy the shared BBQs and private sandy beach area as you soak up Kona's sensational sunsets.
Popular amenities for Kailua-Kona rentals with a pool
House rentals with a pool

Island Views Hale

Kahaluu Bay Get-Away

Tropical Oasis Home with Pool and Walk to Beach

Tiny House Hawaii

Pool, 6 mins to Beach, Ocean View, H7

Tranquil Hawaiian Pineapple Poolhouse with A/C

Big Family Home, Pool, Views, Yard, Lanai, Clean!

NEW! Luxury 2BR/2BA Ocean View Retreat, Pools + AC
Condo rentals with a pool

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

2 Bedroom Penthouse Condo With Ocean View And Pool

Hawai'i paradise at Kona Isle

Blissful paradise with epic view- Hale Mahana

Aloha Paradise! Remodeled with A/C & Ocean View!

Ocean Front Corner Condo in Paradise

Oceanview Kailua-Kona Condo with Lanai

OCEANFRONt 3+2.5 FREE AC BeachGear
Other holiday rentals with a pool

NEW! Expansive OceanView Retreat/Best Beaches/ AC

1 BR condo steps from Kona's premier surf break

Modern Bungalow • AC • Walk to the Ocean

Seahorse Luxury Suite at Seaspray Ocean View

Stunning Oceanfront Beach Condo!

Luxury Ohana, 60ft Salt Pool,

NEW! ADORABLEbungalow Kona Sept specials inquire!

High-End Ocean Sanctuary with Upgraded Interiors
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $361 AUD | $367 AUD | $350 AUD | $335 AUD | $312 AUD | $315 AUD | $305 AUD | $279 AUD | $288 AUD | $319 AUD | $304 AUD | $341 AUD |
| Avg. temp | 6°C | 6°C | 6°C | 7°C | 9°C | 10°C | 9°C | 9°C | 9°C | 9°C | 7°C | 6°C |
Destinations to explore
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- Rentals with pools Hawaii County
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- Hapuna Beach
- Waikōloa Beach
- Mauna Kea
- Kohanaiki Private Club Community
- Waikoloa Beach
- Kilauea
- Mauna Lani Beach Club
- Sea Village
- Manini'owali Beach
- Kona Country Club
- Makalawena
- Spencer Beach Park
- Puʻuhonua o Hōnaunau National Historical Park
- Magic Sands Beach Park
- Waialea Beach
- Big Island Retreat
- Kaloko-Honokohau Nat'l Hist Park
- Pololū Valley Lookout
- Punaluu Black Sand Beach
- Kona Farmer's Market
- Kua Bay
- Hapuna Beach State Recreation Area
- 49 Black Sand Beach
- Kealakekua Bay State Historical Park
- Things to do Kailua-Kona
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