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 lanai features a small table with two blue chairs, offering a direct view of the ocean and surrounding palm trees. A decorative flower pot sits at the center of the table, enhancing the tropical ambiance. The space is shaded and overlooks a green landscape.

4.67 out of 5 average rating, 159 reviews

OCEAN FRONT Kona Studio with Spectacular View.

ALOHA! We invite you to sit back, relax in this spectacular view from our lanai. Absolute BEST location with direct ocean front view at historical Alii Drive. This unit has a tropical theme and is 15 minutes from the Kona airport and 1 minute walk to the ocean!! FAST INTERNET - for those of you decided to escape to paradise to work!! Kitchenette with pots and pans, plates and cups and wine glasses. Kona Town right next door with open air. eateries, live music, outdoor market next. door.

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.

4.75 out of 5 average rating, 207 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.

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.

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!

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.

4.75 out of 5 average rating, 16 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 resort-style pool area is surrounded by lush palm trees and tropical plants. Waterfalls cascade over natural rock formations into the clear blue pool, which features multiple levels. Comfortable lounge chairs are placed along the water's edge, offering shaded spots for relaxation.

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.

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.

A sparkling swimming pool is framed by tall palm trees, providing a refreshing retreat. Nearby lounge chairs and an inviting hot tub complement the outdoor space. The building's balcony overlooks the pool area, enhancing the relaxed atmosphere of the resort.

Wyndham Mauna Loa Village - 2 Bedroom Condo

Tropical Golf-Course Oasis & Lagoon Views – Kailua-Kona, HI Start with coffee on your lanai beside a peaceful lagoon, tee off at the nearby golf club, lounge by sparkling pools, snorkel Kona’s clear waters, and unwind with a sunset breeze.

Popular amenities for Kailua-Kona resort stays

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly Resort Stays

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.

4.78 out of 5 average rating, 27 reviews

Wyndham Paniolo Greens | 2BR/2BA King 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 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

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 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 lounge chairs and umbrella-covered tables, providing a relaxed setting. Palm trees are seen in the background, lining the resort's terrace, while a clear sky complements the modern architecture of the adjacent building.

4.5 out of 5 average rating, 8 reviews

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

Resort rentals with a pool

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

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

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

The resort's exterior features a unique round structure with a vibrant blue, multi-tiered roof. Lush tropical landscaping includes palm trees and colorful plants, framing the building. Water features are visible in the foreground, enhancing the serene setting.

4.78 out of 5 average rating, 45 reviews

Club Wyndham Mauna Loa Village One-Bedroom Condo

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 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.

4.75 out of 5 average rating, 110 reviews

CONTEMPORARY Studio by the Ocean!!

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

5 out of 5 average rating, 4 reviews

Hilton Ocean Tower - Studio - Resort View

A tropical resort showcases a distinguished architectural design with a blue metal roof, surrounded by lush greenery and palm trees. Water features are nestled among vibrant plants, creating a serene atmosphere under a clear blue sky.

4.6 out of 5 average rating, 72 reviews

Club Wyndham Mauna Loa Village Two-Bedroom Condo

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

5 out of 5 average rating, 5 reviews

Hilton Ocean Tower - Studio - Resort View

4.87 out of 5 average rating, 31 reviews

Hilton Ocean Tower - Studio - Resort View

4.91 out of 5 average rating, 46 reviews

Hilton Ocean Tower - Studio Resort View

5 out of 5 average rating, 8 reviews

Hilton Ocean Tower - Studio - Resort View