Holiday rentals with a pool in Kailua-Kona

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Top-rated rentals with a pool in Kailua-Kona

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Guest favourite

Condo in Kailua-Kona

4.93 out of 5 average rating, 183 reviews

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!

Guest favourite

Guest suite in Kailua-Kona

4.95 out of 5 average rating, 128 reviews

Cozy Island Bungalow in Kailua-Kona

Your home away from home after exploring the island’s many beaches, coffee farms, snorkeling/diving spots, downtown Kailua-Kona, etc. Sun-kissed ocean & pool views await you in this cozy, stylish space. A perfect budget-friendly, clean, cool place to rest between your island adventures. Located near downtown Kailua-Kona and 500 ft above sea level, this property offers cooler temperatures and breezes that delight guests. This suite best fits solo travelers or couples who like to be cozy.

Guest favourite

Condo in Kailua-Kona

4.97 out of 5 average rating, 202 reviews

Ocean Front Kona Reef A35! It doesn't get better!

Absolute Ocean Front Condo just a couple minute walk to Kona Town. Amazing views. Beachfront. Amazing pool! Our condo is completely remodeled! You will love the fresh, clean updated style & comfort of this fabulous condo! NEW Full A/C, Stainless Appliances, Completely Stocked Kitchen & Beach & Golf Equipment. ATTENTION GOLFERS! 2 sets of Callaway Clubs! Ready for you to take on the course and enjoy 18 holes! Check out our 2 other Kona Reef condos D33 and B31! TA-109-936-6880-01 STVR-19-352037

Guest favourite

Condo in Kailua-Kona

4.91 out of 5 average rating, 117 reviews

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.

Guest favourite

Guest suite in Hōlualoa

4.91 out of 5 average rating, 355 reviews

Monkey Pod Villa- Guest Suite w/ Pool & Patio

Perched on the cool hillside above Kona, escape to this private retreat on a country estate. Located off the beaten path and away from tourist areas but a 7 mile scenic drive to town & pristine beaches. Awaken from a peaceful night’s sleep to a symphony of the island’s delightful birds. Enjoy a cup of coffee on the garden patio under the shade of a majestic monkey pod tree. After a day of Big Island adventures, unwind with a dip in the sparkling pool and savor the breathtaking Hawaiian sunset.

Superhost

Condo in Kailua

4.82 out of 5 average rating, 103 reviews

Kailua Kona Downtown Condo Walk to Pier & Beaches

In the center of Kailua Kona Village, a new wall to wall renovation has succeeded in bringing beautiful accommodations at a reasonable price to the heart of Kailua Kona Village. This top floor [2nd] air-co unit located in the historic Kona Kai complex has a peek-a-boo view of the coastline. Inspired by the Hawaiian Paniolo, there are unique one-of-a-kind features, and a gentle country-like appearance. Two blocks to beautiful beaches around the Kailua Pier and access to many ocean activities!

Superhost

Condo in Kailua-Kona

4.81 out of 5 average rating, 249 reviews

Downtown Kona Condo with Hot Tub, Pool & Beach!

Experience a haven of serenity in our meticulously crafted Hawaiian paradise garden condo. Nestled within lush surroundings, this exquisite retreat offers the perfect blend of elegance and relaxation. Unwind in our bubbling hot tub, take a refreshing dip in the pool, or simply step across the street and find yourself on a beautiful sandy beach just a few steps away. Whether you seek rejuvenation or adventure, our garden condo provides the ideal sanctuary and is the epitome of tranquility.

Guest favourite

Home in Kailua-Kona

4.95 out of 5 average rating, 152 reviews

Private Pool - 180° Ocean View - Minutes to Beach

This is real Hawaii (except we have fast reliable Wi Fi). Located at 900 ft. elevation, 4 miles to the center of town where there are many restaurants to choose from and just minutes to the nearest beach where the sea turtles are sunning themselves on the shore. This is on one acre in Kona's safest and most desirable neighborhoods. It is the downstairs of a large home where I live quietly upstairs. You share nothing, the pool and spa are yours exclusively while you are here.

Guest favourite

Condo in Kailua-Kona

4.9 out of 5 average rating, 408 reviews

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

Guest favourite

Guest suite in Kailua-Kona

4.96 out of 5 average rating, 119 reviews

1-Bedroom Suite with Private Pool and Garden Lanai

🌬AC included in price! ☀️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. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

Guest favourite

Condo in Kailua-Kona

4.98 out of 5 average rating, 226 reviews

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

This luxurious condo with custom interior design is located in historic downtown Kona from where you can walk to sandy Kailua Bay beach just 2 blocks away, restaurants, supermarket, shopping and entertainment. The condo features: pool with BBQ deck, private laundry, full kitchen with dishwasher and ice maker, two zoned ultra quiet AC, Cal. King bed, a screened-in Lanai with peekaboo view of the ocean, fiber optic internet, and a 65” 4K smart TV!

Superhost

Rental unit in Captain Cook

4.83 out of 5 average rating, 211 reviews

Tropical Hideaway w/ Pool, Hot Tub

Tropical Hideaway is a charming Hawaii-style downstairs studio apartment in a lush garden setting, with ocean views, a salt swimming pool with waterfall, & private hot tub--just three minutes away from fabulous snorkeling, kayaking & diving experiences. The Hawaii accommodation tax of 18% will need to be paid upon arrival (no place to add it in Airbnb's pricing). No kids under 10, renters must be 25 or older.