Resort holiday rentals in Kailua-Kona

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, Marriott's newest Vacation Club property opened in 2017. 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!

A resort building features warm, earth-toned exterior walls and a distinctive red-tiled roof. Two spacious lanai areas are visible, surrounded by lush green landscaping and palms. A pathway leads towards the entrance, with well-maintained grass and tropical foliage in the foreground.

4.73 out of 5 average rating, 192 reviews

Club Wyndham Kona Two Bedroom Bungalow

Every detail at Club Wyndham Kona Hawaiian has been designed to re-create the charming traditional island ambiance found back in the 1930s but with all the modern amenities you expect in a tropical resort. This resort is near waterfalls, museums, golf courses, volcanoes and a multitude of shops and restaurants. This suite offers a king bed in each bedroom and a sleeper sofa in the living area. Additional amenities include a kitchen and dining area, whirlpool tub, washer/dryer and lanai.

Newly Renovated King Room in Oceanfront Resort

Discover our newly renovated Outrigger Kona Resort & Spa with island inspired décor and furnished lanais overlooking Keauhou Bay, the lava cliffs, mountains, and beautifully landscaped grounds. The oceanfront pool and water slide offer family-friendly fun for both kids and adults. Immerse in the vibrant history and traditions of Hawai‘i Island with our activities from cultural tours to getting up close with manta rays, as well as Kona’s premier oceanfront lū‘au experience.

New place to stay

Wyndham Mauna Loa Village 1BR – Near Kona Coast

Escape to the beauty of Kailua-Kona at Club Wyndham Mauna Loa Village. This spacious 1 Bedroom Deluxe Suite features a full kitchen, washer and dryer, living room, and private lanai overlooking tropical gardens. Enjoy six outdoor pools, hot tubs, tennis courts, and nearby golf courses. Located minutes from beaches, dining, and historic Kona sites, this peaceful resort is perfect for couples or small families seeking a relaxing Hawaiian getaway.

A spacious sleeping area features a neatly made bed with a light coverlet and decorative pillows. Above the bed, the word 'KONA' is displayed on a shelf. A full-length mirror and soft lighting enhance the serene aesthetic of the room.

4.62 out of 5 average rating, 157 reviews

Modern and Renovated Ocean Front Condo in Kona!

🌊 Get Lost in Paradise — Steps from the Ocean! Experience the best of Kona in this beautifully upgraded unit, just steps from the sparkling oceanfront. Located only 15 minutes from Kona International Airport, this is the perfect spot to relax, explore, or work remotely with fast, reliable internet. Enjoy the vibrant Kona Town right next door — featuring open-air eateries, live music, and an outdoor market for local flavors and culture.

New place to stay

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.

New place to stay

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

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 for no modern amenity. Outdoor pools and the nearby beach are just the beginning of what’s within reach. Maximum occupancy of 6 person strictly enforced. No exceptions!

Guest favourite

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 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.

A serene outdoor pool is framed by lush tropical landscaping and palm trees, offering a relaxing atmosphere. Comfortable wooden lounge chairs are positioned nearby. A thatched-roof structure is visible in the background, adding to the inviting setting.

4.73 out of 5 average rating, 15 reviews

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

Enjoy your time in Kailua-Kona with this beautiful condo! Located on the Big Island's west coast, it presents a unique blend of 1930s architecture and contemporary comforts. Featuring outdoor swimming pools and convenient beach access, it's a perfect location for an unforgettable holiday. You'll find yourself immersed in the beauty of the Kona coast.

A serene resort pool area surrounded by lush tropical landscaping features a rocky waterfall and various interconnected swimming pools. Sun loungers and umbrellas create inviting spaces for relaxation, while palm trees sway gently in the background under a clear blue sky.

Resort in Waimea

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.

The image captures the resort's beachfront location along Anaehoomalu Bay, featuring a sandy beach bordered by lush greenery and palm trees. The calm turquoise waters create a tranquil setting, with the resort buildings visible in the background against a clear blue sky.

5 out of 5 average rating, 6 reviews

Waikoloa Ocean - 1 Bedroom

Ocean‑view Villa with Kitchen & Pools – Waikoloa, Big Island Wake to sea breezes over ʻAnaehoʻomalu Bay, sip coffee on your lanai, stroll to the beach or pool, snorkel or BBQ, then catch sunset views from your balcony before resort Luau or dinner.

A sparkling pool is framed by palm trees and lounge chairs in a vibrant setting. Colorful umbrellas provide shade, while the resort building is visible in the background. The reflection of the sky on the water enhances the serene ambiance of the pool area.

5 out of 5 average rating, 3 reviews

Hilton The Bay - 2 Bedroom

Resort-Style Villas with Pool, Golf & Island Views – Waikoloa, HI Start your morning with a tropical breeze on your lanai, tee off at the nearby golf courses, unwind by the pool, then enjoy Hawaiian-inspired cuisine as sunset paints the sky.

Popular amenities for Kailua-Kona resort stays

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly Resort Stays

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.

4.8 out of 5 average rating, 5 reviews

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

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

An outdoor swimming pool is surrounded by lounge chairs and palm trees, creating a relaxing environment. The resort buildings rise in the background, with balconies accessible from each unit. Umbrellas provide shade for guests enjoying the poolside area under a clear sky.

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

An outdoor swimming pool is surrounded by palm trees and tropical plants, featuring a shallow area and a set of stairs for easy entry. Lounge chairs are placed along the poolside, inviting relaxation in a serene environment.

4.5 out of 5 average rating, 4 reviews

Holua Resort at Mauna Loa | 2BR King Bed Suite

An outdoor swimming pool is surrounded by lounge chairs, with orange umbrellas providing shade. A poolside building is visible, showcasing large windows. Lush trees are seen in the background, creating a serene environment.

4.67 out of 5 average rating, 6 reviews

Wyndham Paniolo Greens | 2BR/2BA King Suite

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.

4.57 out of 5 average rating, 7 reviews

Holua Resort at Mauna Loa | 2BR King Bed Suite

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

An outdoor swimming pool is surrounded by a safety fence and palm trees. Lounge chairs are positioned around the pool area, with a small shaded gazebo in the background. Clear blue waters reflect the sky, creating a welcoming atmosphere for relaxation.

Holua Resort at Mauna Loa | 1BR King Bed Suite

Resort rentals with a pool

Studio @ Hilton Ocean Tower Waikoloa Village

The resort is positioned along the coastline, surrounded by lush greenery and clear turquoise waters. A series of pools and pathways can be observed, connecting various amenities. The landscape showcases palm trees and gently rolling hills, emphasizing the serene oceanfront environment.

Studio @ Hilton Ocean Tower Waikoloa Village

Hilton The Bay - 2 Bedroom

Hilton The Bay - 2 Bedroom

Lush greenery and tropical palm trees frame the spacious grounds of Hilton Ocean Tower Waikoloa Village. A view of the ocean is visible in the background, complementing the vibrant landscaping and well-kept lawns, providing a serene backdrop for guests.

Partial Ocean View Studio @ Hilton Ocean Tower

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

A clear, inviting pool reflects the sky, framed by lush palm trees and lounge chairs. The adjacent building features spacious balconies and colorful outdoor furniture, creating a relaxed atmosphere. Umbrellas provide shade, enhancing comfort for guests enjoying the tranquil surroundings.

Hilton The Bay - 1 Bedroom

An outdoor swimming pool is framed by lounge chairs and yellow umbrellas. A poolside bar is visible in the background, along with well-kept landscaping featuring tall trees. The area is bathed in natural light, contributing to a relaxed atmosphere.

Wyndham Paniolo Greens | 2BR/2BA King Suite

Resort rentals with a gym

A refreshing outdoor pool is surrounded by palm trees and lounge chairs in inviting turquoise. Cozy seating areas with umbrellas are positioned nearby. The two-story resort building is visible in the background, providing a scenic view common to the tropical environment.

Hilton The Bay - 1 Bedroom

An aerial view showcases the Hilton Ocean Tower Waikoloa Village surrounded by lush greenery and clear blue waters. The ocean is visible in the background, while the resort's circular structure is complemented by palm trees and landscaped gardens. Multiple pools can be seen within the resort grounds.

Partial Ocean View Villa @ Hilton Ocean Tower

Hilton The Bay - 2 Bedroom

The inviting pool area features clear blue water with the words 'The Bay Club' elegantly displayed on the bottom. Lounge chairs and umbrellas surround the pool, while palm trees add a tropical ambiance to the space. A cozy seating area is situated nearby.

Hilton The Bay - 1 Bedroom

Hilton The Bay - 2 Bedroom

An outdoor swimming pool is surrounded by palm trees and lush greenery. Loungers are arranged on the pool deck. A shaded seating area is visible beside the pool, offering relaxation options.

Holua Resort at Mauna Loa | 2BR King Bed Suite

A spacious pool area features a central hot tub with waterfalls surrounded by lounge chairs. Lush palm trees frame the scene, providing a tropical atmosphere. The well-maintained resort buildings are visible in the background, highlighting the inviting outdoor environment.

2BR @ Hilton Kohala Suites Waikoloa

A tranquil pool area is surrounded by lush palm trees and lounge chairs, providing a relaxing atmosphere. Umbrellas offer shade to a few seating areas, while the resort buildings create a welcoming backdrop for guests enjoying the sun-drenched outdoor space.