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Resort holiday rentals in Island of Hawai'i

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Top-rated resort rentals in Island of Hawai'i

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Superhost
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.
Resort in Waikoloa Village

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.
Resort in Kailua-Kona
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 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.
Resort in Kailua-Kona

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.

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.
Resort in Waikoloa Village
4.86 out of 5 average rating, 21 reviews

Wyndham Paniolo Greens | 2BR/2BA King Suite

This resort is a lush, tropical retreat in the heart of Hawaii's Big Island featuring spacious suites with private lanais. There’s plenty to do on-site, including a swimming pool, spa, tennis court, and scenic barbecue areas. This listing is for a 2BR/2BA suite at Club Wyndham Paniolo Greens. Guests will have full access to resort amenities. Suite Details • Size: 1400 Sq Ft • Kitchen: Full • Baths: 2 • Accommodates: 6 Guests • Beds: King Bed - 1 Queen Sleeper Sofa - 1

Superhost
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.
Resort in Waikoloa Village

Studio @ Hilton Ocean Tower Waikoloa Village

Experience paradise at Hilton Ocean Tower Waikoloa Village, perched along the Kohala Coast in Waikoloa Village. Steps from beautiful A-Bay beach and part of Hilton Waikoloa Village's 62-acre oceanfront playground. Access to multiple pools, lagoon, dolphin encounters, and waterslides. Minutes from world-class golf, shopping, and dining. Perfect base for exploring Big Island's volcanoes, beaches, and cultural sites.

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.
Resort in Kailua-Kona
4.78 out of 5 average rating, 36 reviews

Club Wyndham Mauna Loa Village One-Bedroom Condo

Escape to a serene Big Island oasis at Club Wyndham Mauna Loa Village. Nestled amidst the striking greens of 18 holes of championship golf you will enjoy six swimming pools and six hot tubs all within a 5 minute walk to Keauhou Bay. This one- bedroom suite ranges in size from 970to 1,024sq. ft. with private lanais, a fitness facility, water features, gas bbq grills, and a full service activities desk.

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.
Resort in Kailua-Kona
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.

Guest favourite
A comfortable living area features a navy sofa with accent pillows, paired with two armchairs. Natural light enters through large sliding doors, revealing a view of outdoor seating on the patio. A wooden coffee table is placed centrally, with a soft lamp providing additional illumination.
Resort in Kailua-Kona
4.89 out of 5 average rating, 47 reviews

Memorable Hawaii Getaway on the Kona Coast

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

Superhost
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.
Resort in Waikoloa Village
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.
Resort in Waikoloa Village
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.
Resort in Waikoloa Village
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.

An aerial view of an oceanfront resort showcases multiple white buildings surrounded by lush greenery and palm trees. The coastline is visible, with waves breaking against the rocky shore. A clear blue ocean stretches into the distance under a partly cloudy sky.
Resort in Kailua-Kona

Royal Sea Cliff Resort - 1 Bedroom Deluxe

When it comes to amenities, you can expect to be treated royally, much like the ancient kings of the Hawaiian Islands, at Club Wyndham Royal Sea Cliff. Depending on your mood, you can sit by the ocean on the pool deck (rocky coastline) or choose to swim in either of the two outdoor pools.

Popular amenities for resort rentals in Island of Hawai'i

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Family-friendly resort rentals

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.
Resort in Kailua-Kona

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.
Resort in Kailua-Kona

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.
Resort in Kailua-Kona
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.
Resort in Kailua-Kona
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.
Resort in Waikoloa Village
4.6 out of 5 average rating, 5 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.
Resort in Kailua-Kona
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 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.
Resort in Kailua-Kona

Holua Resort at Mauna Loa | 1BR King Bed 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.
Resort in Kailua-Kona
4.5 out of 5 average rating, 8 reviews

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

Resort rentals with a pool

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Resort in Waikoloa Village

Studio @ Hilton Ocean Tower Waikoloa Village

Superhost
A clear pool reflects the sky, surrounded by lounge chairs and umbrellas. The vibrant pool area is complemented by tropical palm trees. The Bay Club's name adorns the bottom of the pool, while a spacious building stands in the background, featuring balconies for guest enjoyment.
Resort in Waikoloa Village

Hilton The Bay - 1 Bedroom

Superhost
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.
Resort in Waikoloa Village

Partial Ocean View Villa @ Hilton Ocean Tower

Superhost
A clear blue swimming pool is surrounded by lounge chairs and umbrellas under palm trees. The Bay Club logo is visible on the pool's surface. A spacious patio features seating areas and colorful chaise lounges, providing a relaxing outdoor space with lush greenery.
Resort in Waikoloa Village

Hilton The Bay - 2 Bedroom

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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.
Resort in Waikoloa Village

Partial Ocean View Studio @ Hilton Ocean Tower

Superhost
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.
Resort in Waikoloa Village

2BR @ Hilton Kohala Suites Waikoloa

Superhost
The image showcases a scenic view of lush tropical gardens and traditional Hawaiian-style buildings, including a roof with bright red shingles. The vibrant green palm trees accentuate the landscape, while the ocean glimmers in the distance under a clear sky.
Resort in Kailua-Kona

2BR @ Wyndham Kona Hawaiian Resort

Superhost
A refreshing outdoor swimming pool is framed by palm trees and lounge chairs. The pool displays the name 'The Bay Club' at its bottom. Nearby, colorful umbrellas provide shade over a seating area. The hotel's second level features balconies overlooking the pool.
Resort in Waikoloa Village

Hilton The Bay - 2 Bedroom

Resort rentals with a gym

Superhost
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.
Resort in Waikoloa Village

Hilton The Bay - 1 Bedroom

Superhost
The image depicts a serene pool area at The Bay Club, featuring clear blue water with a logo on the bottom. Lounge chairs in vibrant colors surround the pool, while palm trees sway gently in the background, complemented by umbrellas and outdoor furniture.
Resort in Waikoloa Village

Hilton The Bay - 2 Bedroom

Superhost
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.
Resort in Waikoloa Village

Hilton The Bay - 1 Bedroom

Superhost
A clear blue swimming pool is featured, revealing a decorative logo at the bottom. Surrounding the pool, lounge chairs in turquoise are arranged alongside shaded umbrellas. Palm trees sway gently in the background, with a two-story building and vibrant seating visible, enhancing the inviting atmosphere.
Resort in Waikoloa Village

Hilton The Bay - 1 Bedroom

Superhost
A serene outdoor pool area is surrounded by palm trees and lounge chairs. Colorful umbrellas provide shade over some chairs, while a bright orange structure is visible in the background. The pool features a decorative logo at its center, enhancing the inviting atmosphere.
Resort in Waikoloa Village

Hilton The Bay - 2 Bedroom

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.
Resort in Kailua-Kona

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

Superhost
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.
Resort in Waikoloa Village

Hilton The Bay - 1 Bedroom

Superhost
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.
Resort in Waikoloa Village

Hilton The Bay - 2 Bedroom

Destinations to explore