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 cozy sleeping area features a headboard with soft, neutral tones. Two decorative pillows add a touch of color, while warm lighting enhances the peaceful ambiance. The wall above is adorned with the letters 'HILO,' providing a distinctive local touch.

4.74 out of 5 average rating, 101 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

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, 190 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.

A lagoon-style pool is surrounded by palm trees and beachfront views. Lounge chairs are evenly arranged along the pool's edge, offering relaxation spots. A twisting waterslide curves into the pool area, adding a playful feature to the serene setting.

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.

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.

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 spacious living area is showcased, featuring a comfortable seating arrangement with two armchairs and a sofa. A wooden coffee table is centered in front. Large windows allow natural light, with views of the patio visible beyond. A television is mounted on a wooden console.

4.97 out of 5 average rating, 33 reviews

Charming One Bedroom Unit on 22 Lush Acres

Kona Coast Resort is the perfect spot for your Hawaiian vacation or short term stay! • Must be 21+ to book • Must provide $250 fully refundable deposit to the resort at check in for incidentals (credit card only) • Resort tax of $11.47/night payable at check in • A/C is optional $10/night • Name on reservation must match photo I.D

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

The Bay Club at Waikoloa Beach Resort is a spectacular hotel on the Big Island of Hawaii and is designed as an ideal Hawaiian haven in the heart of Waikoloa. Superbly situated adjacent to championship golf courses, the premier location of the Bay Club resort provides an unsurpassed vacation setting.

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

Marriott's Waikoloa Ocean Club is a paradise in paradise, where the ancient love story between the goddess Pele and Kamapuaʻa comes to life and inspires every detail. Whether you’re seeking adventure or looking for relaxation, Marriott’s Waikoloa Ocean Club, is a truly unique vacation destination.

Guest favourite

A serene pool area features clear turquoise water, reflecting sunlight. A waterfall cascades over dark rocks, surrounded by lush tropical plants and palm trees. Lounge chairs are positioned along the pool's edge, providing a place to relax. The vibrant blue sky enhances the inviting atmosphere.

5 out of 5 average rating, 7 reviews

Hilton Ocean Tower - Studio - Resort View

Set in the Hilton Waikoloa Village Resort on the Kohala Coast, the Ocean Tower hotel is at the edge of Waiulua Bay. Explore the resort via tram and enjoy a choice of three pools and a four-acre ocean-fed lagoon. Perks include on-site shopping, our full-service spa, and access to Dolphin Quest.

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

Carved out of an ancient lava field, this 112-acre oasis in the heart of Waikoloa is complemented by a splendid collection of resort-style amenities with convenient access to the award-winning dining, plentiful shopping, and recreational activities of the nearby Hilton Waikoloa Village.

Popular amenities for Kailua-Kona resort stays

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-Friendly Resort Stays

A serene outdoor swimming pool is framed by palm trees and lush landscaping. Lounge chairs are placed around the pool area, inviting relaxation. A small spa is also seen beside the pool, surrounded by a protective fence ensuring safety.

Holua Resort at Mauna Loa | 1BR King Bed 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

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 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.

4.67 out of 5 average rating, 3 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 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 palm trees and tropical foliage, offering a relaxing atmosphere. A few lounge chairs are positioned around the pool area, and a small spa is visible next to the pool. A gazebo is present in the background.

4.75 out of 5 average rating, 4 reviews

Holua Resort at Mauna Loa | 1BR King Bed Suite

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 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

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

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

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

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 bordered by lounge chairs and shaded umbrellas, surrounded by palm trees. The modern resort buildings are visible in the background, complementing the serene atmosphere of the tropical setting.

4.25 out of 5 average rating, 4 reviews

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

Hilton The Bay - 2 Bedroom

Hilton The Bay - 2 Bedroom

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 serene pool area is highlighted, featuring a clear blue surface with the name 'The Bay Club' displayed at the bottom. Surrounding palm trees provide shade over lounge chairs, while colorful pool umbrellas add vibrant contrast. A two-story building is visible in the background.