
Holiday rentals with a pool in Kailua-Kona
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Top-rated rentals with a pool in Kailua-Kona
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Oceanfront/Hawaiian Charm W/Modern Amenities
Welcome to Hale Kani Moana (House of Ocean Soundsâ¤ď¸)âŚthe best location, city center on world famous Aliâi Drive. Cozy Hawaiian Charm w/ modern amenities. At your doorstep are the best restaurants, nightlife, and shopping. Stunning oceanfront unit w/sunset views (Fall/Winter). Listen to the ocean waves gently crash as you fall asleep. Fully stocked kitchenette, bathroom/shower, and all the beach equipment youâll need. FREE Parking+FAST Wifi :-) Note: 3rd (Top Floor) stairs only, no elevators

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 of your life unfold. Tranquility, privacy, and stunning beauty await you. A masterclass of design in harmony with nature, this exquisite and inspired 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.

Aloha Paradise! Remodeled with A/C & Ocean View!
Best unit at Kailua-Konaâs 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!

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.

True Oceanfront, Top-Floor, Downtown, A/C, Parking
Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a boutique complex, meaning no noise from the street or guests above. After a busy day at the beach and a night on the town, you'll appreciate the peace and quiet of your own space with only the sound of the ocean to lull you to sleep.

Ocean Views~by Honl's Beach~Heart of Kona~AC
ENJOY OCEAN VIEWS from a newly renovated Stylish condo in one of Kona's most desirable locations. Condo is an apx 6 to 8 min walk to a variety of Ocean Side Restaurants, entertainment and a quick walk to Honl's Beach. No rental car is needed as you are a short walk into town. The condo looks directly out to the Pacific Ocean and is on the ground floor so (no long stairs to climb). Free dedicated parking spot, which is so IMPORTANT in KONA now! 65" SMART TV, AC, the SOFA folds to a 2nd bed.

Right-on-Ocean; Renovated; Walk to Beach/Town, A/C
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.

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.

Stunning Serene Bali Retreat [Pool/AC/Ocean View]
Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai and Balinese architecture, and ornate, hand-carved wood. Floor-to-ceiling windows and skylights showcase the beauty of the Big Island. The kitchen and living rooms connect to spacious bedrooms with a covered dining lanai stretching back to the private pool. Perched on a hill with 180Âş ocean views, this secluded retreat enjoys a cooler breeze than busy downtown while not being far from the action.

Downtown Kona Plaza Condo w/AC
Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

1-Bedroom Suite with Private Pool and Garden Lanai
đŹAC included in price! âď¸We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. đŚOr stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. đżWhatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.
Popular amenities for Kailua-Kona rentals with a pool
House rentals with a pool

Tropical Oasis Home with Pool and Steps to Beach

Tiny House Hawaii

Private Pool & Spa-Beautiful Oceanview Home

Huge Kona Home ⢠Ocean View ⢠Pool ⢠4 bdrms ⢠AC

Panoramic Ocean Views With Private Saltwater Pool

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

Ocean, Sunset, Mountain & Celestial Views

Halia Hale
Condo rentals with a pool

Discounted A35 Kona Reef Oceanfront AC Park Free

RARE FIND - Spacious 2BR, Steps from Aliâi Dr.

Partial Ocean View, AC, King Bed, 2 Pools

Kailua Village Condo in the Heart of Kona

Oceanfront Condo/Hawaiian Style. 1Bd, w/AC & Wifi

Ocean Front Corner Condo in Paradise

Spectacular View, Direct Oceanfront Kona,Top Floor

O/F View, on ocean 1 Bdrm, Casa De Emdeko Ironman
Other holiday rentals with a pool

Centrally Located Downtown Kona Condo

Ocean view with central location tropical paradise

Brand NEW Oceanfront Retreat! Steps to Beach!

Downtown Kona Condo / Vintage Hawaii / Fast WiFi

1BR Kona Condo w/ Chefâs Kitchen & Tropical Lanai

Modern Kona Retreat ⢠Walk to Ocean & Town

Brand new Luxury Oceanfront Living in Kona with AC

Oceanfront Chic ⢠Just Renovated
Quick stats about holiday rentals with a pool in Kailua-Kona
Total rentals
1.9K properties
Nightly prices starting at
$86Â NZD before taxes and fees
Total number of reviews
71K reviews
Family-friendly rentals
960 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
1.1K properties have a dedicated workspace
Destinations to explore
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- Hapuna Beach
- Mauna Lani, Auberge Resorts Collection
- Four Seasons Resort Hualalai
- Kaunaoa Beach
- Pahoa Beach
- Kohanaiki Private Club Community
- Mauna Kea Golf Course
- KeâEI Beach
- WaikĹloa Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- Waikoloa Beach Golf Course
- 49 Black Sand Beach
- Hapuna Golf Course
- Kona Country Club
- Kona Dog Beach
- Kukiâo Golf & Beach Club
- Nanea Golf Club
- Kealakekua Bay State Historical Park
- Makalawena Beach
- Mauumae Beach
- Honokohau Beach
- ĘťAlula Beach
- PololĹŤ Beach
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