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

Apartment 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

Apartment in Kailua-Kona

4.97 out of 5 average rating, 203 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

Apartment 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

Apartment 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!

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

Apartment in Kailua-Kona

4.9 out of 5 average rating, 409 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

Apartment in Kailua-Kona

4.82 out of 5 average rating, 110 reviews

Oceanview condo walking distance to Kona Town

Location! Location! Location! Welcome to our centrally located studio condo #345 in the heart of Kona Town! Nestled between Ali’i Drive and Kuakini Hwy, you’ll be within walking distance of Kona’s best restaurants, shops, beaches, and bars. Enjoy swimming & snorkeling at the nearby pier, just a short walk away. Unwind by the pool or hot tub, take an evening stroll for a nightcap, or start your day with a morning walk for a cup of Kona coffee. Your perfect getaway awaits!

Guest favourite

Apartment in Kailua-Kona

4.89 out of 5 average rating, 216 reviews

Kona Hideaway > Pool > Ocean View > AC > Fast Wifi

Hawaii is about views - and this space offers lucky eyes the vast Pacific ocean straight ahead and lush fruit and greenery to the left and right. Under your breath you whisper "I could get used to this", planning your next trip back already in your mind. The bedroom is pointed directly at the view, a pool, an avocado tree and starfruit tree, and a glorious island paradise lanai. Practical too: laundry, excellent wifi, smart TV, and a full kitchen.

Guest favourite

Apartment 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

Apartment in Kailua-Kona

4.85 out of 5 average rating, 158 reviews

Luxury in the Heart of Kona

We are located in the heart of Kona town. You can walk to yummy restaurants, the farmer's market, 2 beaches, great island shopping and fun island activities. Our condo has been remodeled with tile floors, granite countertops, an added kitchenette, and beautiful all wood furniture. We recently replaced the mattress as well. Our unit overlooks the pool and the beautiful Islander Inn tropical gardens.