Resort vacation rentals in Kailua-Kona

4.33 out of 5 average rating, 3 reviews

Amazing Kona 2BR Mauna Loa Village Pool HotTub BBQ

##Please verify availability first. Mahalo! Escape to a serene Big Island oasis at Mauna Loa Village (a beautiful timeshare resort). Located just next door to the Kona Country Club, which features a championship golf course. This tantalizing Kailua-Kona resort is a quiet oasis tucked away from the town traffic and crowds, yet only two blocks from shopping, restaurants, and movie theaters. Plus, there's a wide array of golf courses, beaches, as well as hiking/biking/horseback riding trails nearby

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Ironman Week•2BR/2BA•Walk to Kailua Pier•Oct 4-11

Stay at Club Wyndham Kona Hawaiian Resort during Ironman World Championship Week! This newly renovated 2BR/2BA villa sleeps 6 and is about a 25-minute walk (1.4 miles) along scenic Aliʻi Drive to Kailua Pier—ideal for athletes and spectators who want to avoid race-day parking. Enjoy a full kitchen with stainless steel appliances, private lanai, A/C, in-unit washer/dryer, plus resort pools, hot tubs, BBQs, lush tropical grounds, and nearby beaches, dining, shopping, and breathtaking Kona sunsets.

4.67 out of 5 average rating, 3 reviews

Kailua-Kona Resort @ Holua Mauna Loa- 2 Bd Suite

Discover the beauty of Hawaii's Big Island at Holua Resort at Mauna Loa Village. Nestled along the scenic Kona Coast, this peaceful retreat offers spacious villa-style accommodations surrounded by lush tropical landscapes. Enjoy sparkling pools, tennis courts, and nearby championship golf, or explore pristine beaches, snorkeling, coffee farms, and volcanic wonders. The perfect home base for relaxing and experiencing the island’s natural beauty and aloha spirit!! *Kamaʻāina discounts available~

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Resort in Kailua-Kona

4.76 out of 5 average rating, 123 reviews

CONTEMPORARY Studio by the Ocean!!

🌊 Escape to Paradise on Historic Alii Drive 🌺 Welcome to your beachside retreat in the heart of Kona! Just one minute from the oceanfront and located along the iconic Alii Drive, this beautifully renovated unit offers the ultimate Hawaiian getaway. Unbeatable location — walk to the beach, shops, and restaurants Fully upgraded with a kitchenette (includes pots, pans, dishware, and wine glasses) High-speed internet — perfect for remote work Only 15 minutes from Kona International Airport

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A resort pool area is visible with clear blue water and a rock feature. Lounge chairs are arranged around the pool, and palm trees are scattered throughout the landscape. The two-story building provides a backdrop, featuring multiple balconies and flower gardens.

4.81 out of 5 average rating, 36 reviews

Shell Kona Coast Resort Ohana Suite Honu

Shell Kona Coast Resort offers spectacular views of palm trees and calm waters. This resort is situated on the ocean, giving you access to the magical setting where the land meets the sea. This resort features swimming pools, hot tubs and a sauna, plus you can try Hawaiian dining at Sunset Terrace restaurant. This suite offers a king bed in the master and guest bedroom and a sleeper sofa in the living room. Additional amenities include a kitchen, dining area, washer/dryer, and lanai.

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The image captures a spacious resort area featuring multiple swimming pools that curve gracefully through lush landscaping. Palm trees surround the pools, and views of Anaehoomalu Bay can be seen in the background, highlighting a serene ocean ambiance.

Marriott Waikoloa Ocean - Stunning one bedroom

We are able to offer reservations in weekly increments with arrivals and departures, Fridays, Saturdays, and Sundays Marriott's Waikoloa Ocean Club mirrors the natural beauty and rich culture that defines Big Island, sharing the grounds with Waikoloa Beach Marriott Resort & Spa. Guests will enjoy the Hawaii Call Restaurant & Lounge, Mandara Spa, Sunset Luau, a total of three swimming pools, two children's pools, a fitness center and more!

An outdoor swimming pool is surrounded by a paved area and is enclosed by a white fence. Lounge chairs are positioned along the edge, and tropical palm trees create a lush backdrop under a clear blue sky.

4.76 out of 5 average rating, 17 reviews

Holua Resort at Mauna Loa | 2BR King Bed Suite

Spectacular natural beauty welcomes you the moment you arrive. Stay in spacious villas featuring private lanais with stunning views, then enjoy 18 holes of championship golf or watch the sea turtles at nearby Kahalu'u Beach Park. Holua Resort at Mauna Loa | 2BR/2BA King Bed Suite • Kitchen: Full • Baths: 2 • Accommodates: 6 Guests Beds • Bedroom 1: 1 King Bed • Bedroom 2: 1 King Bed or 2 Twin Beds • Living Area: 1 Sleeper Sofa

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5.0 out of 5 average rating, 3 reviews

A seaside view showcases vibrant turquoise waters against a backdrop of palm trees and coastal buildings. A wooden railing frames the scene, while a patterned canopy adds shade. The outdoor dining area is visible, enhancing the relaxed atmosphere with ocean breezes.

Resort in Kailua-Kona

Kona Hawaiian Resort- 2Bd Dlx

Authentically Hawaiian in this charming Resort @ Kona Hawaiian. You'll have a great time at this comfortable place to stay. On the Big Island’s west coast, you’ll find this delightful retreat built to capture the natural wonder of Kailua-Kona. Beautifully designed to capture the charm of the 1930s, you’ll want no modern amenity. Outdoor pools and the nearby beach are just the beginning of what’s within reach..~ Mahalo~

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2BR @ Wyndham Kona Hawaiian Resort

Unwind at Club Wyndham Kona Hawaiian Resort, a charming hideaway just steps from the beach in beautiful Kailua‑Kona on Hawaii’s Big Island. Palm‑lined paths and lush gardens surround two outdoor pools and spa tubs, while a picnic and BBQ area invites relaxed gatherings. With easy access to the waterfront, shops and local dining, you’ll be perfectly placed to soak in island life.

Guest favorite

A tranquil pool area is framed by tropical landscaping, featuring a mixture of palm trees and vibrant greenery. Natural stone accents surround the pool, and comfortable lounge chairs are arranged nearby. Tiki hut structures provide shaded seating, enhancing the relaxed atmosphere of the space.

5.0 out of 5 average rating, 12 reviews

Kona Hawaiian Resort-2 bedroom

Kona Hawaiian Resort bungalows are located near the action. Just a short walk to restaurants, shopping, and the beach. Come relax by the pool or watch the waves crash on the black shores of Kona. These spacious 2 bedroom bungalows are nestled among the trees and give you the privacy you want. Enjoy breakfast on your balcony and listen to the birds chirp.

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5.0 out of 5 average rating, 3 reviews

Hilton Kings' Land - 2 Bedroom

Lavish Lagoon-Style Pool Escape with Golf Views – Waikoloa Village Begin your morning on your private lanai, overlooking lush golf fairways. Explore lava-rock waterfalls and waterslides at the resort pool, then ride the shuttle to nearby Hilton Waikoloa Village. Finish your day with starlit BBQ.

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Resort view 1 king bed

Resort view room with one king bed offers tropical resort views, balcony with outdoor seating, wifi, flat screen TV, mini refrigerator, coffee and tea maker, work desk, in room safe, premium bath amenities, and calming decor, ideal for a relaxing and convenient stay.

Popular amenities for Kailua-Kona resort rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly resort rentals

New place to stay

Hilton Grand Vacations Club Kings' Land Waikoloa

Kona Hawaiian Resort - 2bd/2ba-2King beds/Sofa bed

Resort in Kailua-Kona

Kona • Couples Island Retreat • Pool + Ocean

New place to stay

Tropical 1bd - Check-in's Fri, Sat & Sun ONLY!

The outdoor pool area is surrounded by lounge chairs and tropical plants, providing a relaxing environment. A covered seating area is visible nearby, and the bright sky reflects on the water's surface, enhancing the peaceful atmosphere of the resort.

Kona, Hawaii 2 Bedroom (sleeps 6) at WorldMark

Kona • Island Family Trip • Pool + Views • 2Br

Hilton Kohala Suites - 2 Bedroom Premier

Ironman Special: 10/7-10/14 Oceanside Sleeps 6

Resort rentals with a pool

Resort in Waikoloa Village

An outdoor swimming pool surrounded by lounge chairs is featured, with vibrant yellow umbrellas providing shade. Lush trees line the background, and a clubhouse is visible to one side, enhancing the tropical atmosphere of the resort.

4.84 out of 5 average rating, 37 reviews

Wyndham Paniolo Greens | 2BR/2BA King Suite

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An outdoor swimming pool is surrounded by stone decking and lounge chairs. Palm trees provide shade, and nearby, the modern resort buildings reflect a coastal design. The sky is partly cloudy, contributing to a relaxed, inviting atmosphere.

4.83 out of 5 average rating, 6 reviews

Wyndham Royal Sea Cliff | 1BR/1BA King Balc Suite

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Resort in Waikoloa Village

A shimmering outdoor swimming pool is surrounded by lounge chairs under yellow umbrellas. Lush tropical trees frame the scene, while a building offers amenities in the background. The patio is paved with natural stone, contributing to a relaxed poolside atmosphere.

4.76 out of 5 average rating, 33 reviews

Wyndham Paniolo Greens | 2BR/2BA King Suite

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An outdoor swimming pool is surrounded by palm trees, with lounge chairs lining the edges. A shaded bar area and dining space are visible in the background, providing a relaxed atmosphere. The pool is designed with varying depths, featuring a gradual slope at one end.

5.0 out of 5 average rating, 8 reviews

Wyndham Kona Coast Resort|1BR/1BA King Balc Suite

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The outdoor swimming pool is surrounded by palm trees and features a patio area with shaded seating. The pool's clear blue water reflects the sky, with a gradual slope leading to a shallow end marked by a 3-foot depth sign.

4.7 out of 5 average rating, 10 reviews

Wyndham Kona Coast Resort|2BR/2BA Queen Balc Suite

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An outdoor swimming pool is surrounded by lounge chairs, with palm trees providing shade. The pool area features a stone deck, and modern resort buildings are visible in the background. Clear skies with subtle clouds create a serene tropical atmosphere.

4.75 out of 5 average rating, 8 reviews

Wyndham Royal Sea Cliff | 2BR/2BA King Balc Suite

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The outdoor pool area is surrounded by lush palm trees and tropical foliage. A thatched-roof hut provides shade, while wooden lounge chairs invite relaxation. Natural rock formations outline the pool, which reflects the soft colors of the sky at dusk.

4.6 out of 5 average rating, 5 reviews

Wyndham Kona Hawaiian | 2BR/2BA King Bed Suite

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An outdoor swimming pool is surrounded by a secure fence and manicured landscaping. Several lounge chairs are positioned near the pool, which features a hot tub area. Sunlight filters through palm trees, creating a relaxing atmosphere.

4.67 out of 5 average rating, 3 reviews

Holua Resort at Mauna Loa | 2BR King Bed Suite

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Resort rentals with a gym

A bright living area features green walls and large windows framed by sheer curtains. Two comfortable armchairs and a sofa surround a circular table, while a textured lamp adds light. A colorful patterned rug enhances the overall vibrant ambiance.

Resort in Waikoloa Village

Private Tropical resort in Kona

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A multi-story building is shown, featuring expansive balconies that overlook a landscaped area. The structure is complemented by vibrant greenery and colorful flowers in the foreground, creating a serene outdoor setting. The clear blue sky enhances the inviting appearance of the resort.

WYDHAM Paniolo Greens HI

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Wyndham Mauna Loa Village 1BR – Near Kona Coast

A spacious outdoor swimming pool is surrounded by palm trees, with inviting lounge areas and a bar in the background. Sunlight reflects off the water, and an accessible ramp leads into the pool, enhancing ease of access.

4.33 out of 5 average rating, 6 reviews

Wyndham Kona Coast Resort|1BR/1BA King Balc Suite

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The outdoor swimming pool is framed by palm trees and a stone patio. A designated children's area is visible, along with a bar area beneath a canopy. Lounge chairs are arranged around the pool, creating a relaxing environment. Soft clouds are seen in the blue sky above.

Wyndham Kona Coast Resort|2BR/2BA Queen Balc Suite

Accuracy

An outdoor swimming pool is framed by lounge chairs and umbrellas, surrounded by palm trees. The modern resort buildings are visible in the background, with a clear blue sky overhead. The setting offers a serene environment for relaxation.

Wyndham Royal Sea Cliff | 1BR/1BA King Balc Suite

An outdoor swimming pool is framed by palm trees and lounge chairs, inviting relaxation. The pool area is surrounded by stone flooring and features a light blue tile trim. The resort buildings are visible in the background, complemented by a bright, clear sky.

Wyndham Royal Sea Cliff | 1BR/1BA King Balc Suite

An inviting outdoor swimming pool is surrounded by palm trees and features a stone deck. A swim-up bar with shaded seating areas is visible in the background, enhancing the resort’s tropical ambiance. The sky reflects soft hues, suggesting a serene atmosphere.