Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas
Welcome to your guide for Hawaii vacation rentals, where tropical luxury meets everyday comfort. From sunrise-facing lanais on Maui to private bungalows near the lush valleys of Kauai, each rental is handpicked for quality, location, and local charm.
Why Book a Vacation Rental in Hawaii?
Unlike traditional hotels, vacation rentals provide full kitchens, private lanais, and dedicated living space—ideal for families, couples, or long stays. Many homes are steps from the beach, offer high-speed Wi-Fi, and include perks like pools, BBQ areas, or resort access.
Popular Vacation Rental Locations
- Waikiki, Oahu – High-rise condos near beaches, shops & nightlife
- Kihei, Maui – Walkable, affordable, and family-friendly
- Princeville, Kauai – Scenic cliffs, golf, and luxury condos
- Kailua-Kona, Big Island – Oceanfront escapes with sunset views
Rental Types Available
- Beachfront Condos with resort amenities
- Private Beach Homes with full kitchens
- Luxury Villas with pools & panoramic views
- Studios & Bungalows for solo travelers or couples
What Makes To-Hawaii.com Rentals Stand Out?
- Verified properties across all major Hawaiian islands
- Detailed descriptions, amenities, and photo galleries
- Helpful internal links to top Hawaii activities and Hawaii rental cars
- Flexible booking options, from weekend getaways to long-term stays
Plan Your Dream Island Escape
Explore the beauty of the islands with confidence. Whether you're whale watching on Maui, snorkeling on Oahu, or enjoying a peaceful sunrise on Lanai, our vacation rentals offer the perfect base for unforgettable memories. Start planning your Hawaiian adventure today.
Hale Kamaole 113 - Relax and Enjoy the Beach
Book with us and come to Maui to explore everything we have to offer!Well maintained condo conveniently located very close to world class beaches, shops, and restaurants! Fantastic location close to the pool with lots of parking on site. Relax on your lanai with the...
Studio Villa
Starting from $500 per night - request your dates nowThe Westin Ka'anapali North in Maui has just what you need for your first, or next, relaxing vacation — a beautiful one bedroom villa. This well-equipped, fully furnished property offers elegant, luxurious living...
Perched at Pearl Harbor
Nestled atop a hill, our home offers an enchanting view of Pearl Harbor. Perfect for remote professionals and families alike, our property provides the perfect blend of comfort and scenic beauty.Welcome to our inviting home, where you can savor breathtaking Pearl Harbor...
Kalama Terrace 2BR with Pool, BBQ & Walk to the Beach
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Experience the best of Maui in this nice island-style 2-bedroom, 1-bath unit at Kalama Terrace! The main...
The Turtle House, a 5 Bedroom Oceanfront Villa!!!
The Turtle Villa is the perfect location for an unforgettable and authentic Hawaiian experience. One of the best oceanfront views on the island with the most stunning sunsets. Our home is great for family getaways or large gatherings. Create family memories that will...
2BR Ocean View condo resort in Princeville. Private path to walk to the beach!
This condo is located in Hanalei Bay Resort and is available for both Christmas week and New Years weeks this year December 20, 2025 to January 3, 2026. Best price per night is staying all 7 nights each week Saturday to Saturday. If you are looking to stay at a place in...
The Lodge at Kukui‘ula - Villa 2
The four-bedroom villas at The Lodge at Kukui'ula on Kaua'i offer luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf–designed golf course, sprawling spa...
Ocean-City Luxurious Vacation at the Sky Ala Moana with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is Honolulu's newest symbol of luxury, featuring two distinct towers: The Residence and...
Maui Ka’anapali Villas #205: One bedroom ocean view on N. Kaanapali Beach
Maui Ka’anapali Villas #205: One bedroom ocean view on N. Kaanapali Beach with Pool and Beach Access. Maximum occupancy: 2Bed size: King BedAC: Central ACOffice space: Desk and desk chairBright, open and spacious one bedroom condo with ocean views. The expansive...
Ocean View, Beach, Pool, Hot Tub, Spa, Waterslide, Lanai
🌺 Kauai Dreams Escape – Oceanfront ParadiseExperience the lush natural beauty of Kauai at this stunning top-floor oceanfront retreat—the best spot in the entire building. Step onto your private lanai and feel as if you're standing on the bow of a luxury ship,...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Large Floorplan | 2 Units, 4 Bedrooms | HK ML-1790
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Elegant Waikiki Retreat - Ocean View & Luxe Decor
Experience refined island living in this modern Waikiki condo with an ocean view. Designed for the discerning traveler, the space features SoHa Living décor, Nordstrom and Neiman Marcus-inspired furnishings, and Cozy Earth luxury linens. Enjoy a private lanai, stylish...
Island Comfort: 2BR at Wyndham Kona Coast Resort
Enjoy your Hawaii retreat in this spacious two-bedroom suite at Wyndham Kona Coast Resort, designed to accommodate up to six guests. The villa includes two separate bedrooms, a full kitchen with modern appliances, two bathrooms (one with a whirlpool tub in many suites),...
Breathtaking Ocean Views, You'll Never Want To Leave Waikiki!
Construction Notice 10/20/25: Exterior painting work is currently scheduled from 10/29 - 12/12/2025. During this time, the lanai will be locked and not accessible to guests. For your safety, please do not attempt to use the lanai at any time. You may also hear...
Oceanfront Retreat! Near Waihee Coastal Dunes and Wetlands Preserve, Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Islands at Mauna Lani M1
Tropical furnishings, island-inspired wall art, and blonde wood flooring combine to make the Islands at Mauna Lani M1 a welcoming and relaxed vacation rental option on the Island of Hawaii. This two-bedroom two and a half bathroom split-level townhouse is perfect for...
Kaanapali Alii 3106
Welcome to Kaanapali Alii 3106, a luxury vacation rental nestled in the heart of Maui's exclusive Kaanapali Alii Resort. This deluxe oceanfront condominium offers stunning, unobstructed views of the sparkling Pacific Ocean and neighboring islands of Lana'i and Molokai....
Luxurious Tent for a Romantic Getaway in Mountain View Village, Hawaii
This luxurious tent is located in the lush rainforest of Volcano, Hawaii, and provides the perfect setting for a romantic getaway, solo traveller, or just a place to detach from your every day bustle and hustle. Inside, the tent boasts a contemporary interior with a...
Kai Lani Luxury 6D by Gather: Ground-Level 3BR w/ Ocean View Lanai
Set within Ko Olina’s premier oceanfront community, Kai Lani Luxury 6D by Gather offers a serene single-level retreat where tropical landscapes, gentle ocean breezes, and modern comforts blend seamlessly. This three-bedroom, two-bathroom villa spans 1,320 sq. ft. and...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Family Friendly | 2 Units, 3 Bedrooms | HK ML-1355
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
NEW! KBM Resorts | Ocean Views | FREE CAR | Wailea Ekahi | 1-Bedroom Condo with Luxury Amenities! WKV-45C
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Beachfront, spacious, absolutely stunning Oceanfront Condo with FREE Parking
Aloha! Our spacious Fourth floor 1 bed 1 bath condo with spectacular views of the beach, ocean and Molokai & Lanai islands awaits your Hawaiian adventure. Enjoy the sights and sounds & breeze of the Pacific Ocean from the living room & kitchen! You can't miss watching...
Grand Opening Prices! Ocean Views! Steps 2 Beach!nEntire condo in Kihei, Hawaii!
Welcome to our slice of heaven - Pineapple Paradise! Our recently remodeled condo boasts a peaceful, laid back vibe, making it the perfect choice for a relaxing getaway to escape all your cares.This gem—steps from the beach—is tucked away from the hustle and bustle...
The Lodge at Kukui‘ula - Villa 3
Vacationing in Villa 3 at The Lodge at Kukui'ula offers a luxurious experience nestled in the heart of Kaua'i's stunning South Shore. This exceptional accommodation provides guests with an authentic Hawaiian retreat featuring sophisticated plantation-style architecture...
Waikiki Shore 518 Partial Ocean View 2 Bedroom
Located in the only condominium building on Waikiki Beach, this two bedroom, two bath condo offers partial ocean views and all the comforts of home. Perfect for families or couples traveling together, it’s just steps from the shoreline, shops, and dining.Unit 518...
Sands of Katana Vacation Club, Hot Tub, Pool!
Midway between the world famous Kaanapali and Kapalua beaches lies the Sands of Kahana Vacation Club. The perfect laid-back retreat, this resort is equipped with everything you need to experience a true picture-perfect vacation. Spend mornings walking on the beautiful...
Oceanfront Bliss at Royal Mauian #405–Stunning Views, Prime South Kihei Location
Royal Mauian #405 – Oceanfront Comfort with Stunning Coastline ViewsRoyal Mauian #405 is a two-bedroom, two-bathroom condo designed for guests who want to experience the very best of oceanfront living in South Kihei. With panoramic views of the Pacific Ocean and...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Panoramic Ocean Views 2-bedroom Luxury Villa At Kapalua Bay Villas Maui | 2 Units, 3 Bedrooms | KBV ML-2005
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kapalua Bay Villa 19G5 Gold Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- Split level condo with 19 stairs between the driveway and front door- Tile entry, kitchen and bathrooms, carpet in living area, dining room and bedroom- Living room, kitchen and ½ bath on first floor; bedroom, full bathroom and laundry...
2-Bedroom Condo near Downtown Kona | Close to Beaches & Dining
This bright and breezy 2-bedroom, 2-bath condo is perfectly located in the heart of Kailua-Kona. Located on Ali‘i Drive, you`re just minutes from beaches, shops, and restaurants, it’s the ideal spot to relax after a day of island adventures.Features:- A/C- Full...
34th FL Allure Waikiki | Parking | Pool | City & Mtn Views
The Space: This beautifully appointed 2-bedroom, 2-bathroom suite features floor-to-ceiling windows throughout and a curved lanai with incredible panoramic views. Located on the 34th floor of the luxury Allure Waikiki tower.Master Suite: King bed, ocean views, walk-in...
Waikiki Ocean City View 2 Bedroom 2 Bath
Summary:Newly Renovated Waikiki Split 2BR/2BA Efficiency Unit. Free garage parking.The Space:Reconnect with loved ones in this family-friendly place. Situated at the entrance of Waikiki, our delightful split 2Br 2BA efficiency unit in the Hawaiian Monarch building...
Hi6-ST1- The Dolphin Bay Estate
Escape to the enchanting Dolphin Bay Estate, a luxurious vacation rental nestled on the pristine shores of the Big Island, Hawaii. This exquisite property offers the perfect blend of serenity, elegance, and convenience, making it an idyllic retreat for those seeking a...
Island Living w/Ocean Views, Wi-Fi and Pools-G510A
Your Hawaiian dream vacation becomes a reality when staying at this tropical oasis set within walking distance to the iconic Maui shores. The Maui Banyan resort is sprawling with lush flora and top-notch amenities including two swimming pools, jacuzzis, tennis courts,...
Maui Vista 1406: Top Floor Large 2 br condo with Loft & Ocean Views Sleeps 4
Large two-bedroom condo with a loft with ocean views. This vacation rental features a queen bed in the master bedroom, two twins in the loft bedroom, and a pull-out sofa bed in the living room. This unit looks out over the pool. Relax on the lanai and enjoy paradise....
Idyllic Vacation at Ko Olina Hillside Villa 1528-4
Resort in Kapolei with a water park and a fitness centerA water park, a fitness center, and a hot tub are available at this smoke-free resort. Other amenities include laundry facilities. Limited housekeeping is available. Air-conditioned accommodations at this resort...
Diamond Head 1 Bedroom Condo Queen Bed & Bunkbed
Legal Vacation Rental - This beautifully furnished 1 bedroom suite with Queen bed & with separate living room offering twin bunkbeds.The full kitchen is bright spacious and well equipped. Condo has awesome views out over the Ocean and also Kapiolani Park - Includes flat...
Fabulous 7 bedrooms for 16 above famous Anini Beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This fabulous 7 bedrooms and 5 baths for 14 to 16 people, is situated right above famous Anini Beach, with an 8-10 minute walk down the Anini Beach trail just steps away from the...
Kaanapali Alii 264
Welcome to your dream luxury vacation rental at Kaanapali Alii 264, a stunning one-bedroom condominium nestled in the heart of Maui's exclusive Kaanapali Alii Resort. This deluxe residence offers breathtaking views of the West Maui Mountains and the vibrant tropical...
Kilipue Retreat by Gather | Luxe 3BR Home w/ Fenced Yard Near Ko Olina
Kilipue Retreat places you at the quiet end of a Kapolei cul-de-sac, minutes from beaches and big-city conveniences yet wrapped in the calm of a residential neighborhood. Newly refreshed and fully furnished, this 3-bedroom holiday home welcomes corporate guests,...
Hale Pau Hana #707 Ocean Front, Central AC, Oceanfront Complex
Hale Pau Hana #707 is a 2 bedroom, 2 bath unit on the 7th floor with a panoramic ocean view and central A/C throughout. It provides a fully-equipped kitchen, 2 flat-screen TVs, and free WIFI. Go to sleep in your comfortable cal king bed as you enjoy the sound of the...
Indulge in Home-Like Comfort Rooftop Swimming Pool and Hot Tub!
Family-friendly property located just steps from the beachThis listing is for a room within a hotel.✦ Your room is 443 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.✦ Daily...
Gorgeous Beachfront Nanea Resort+Amenities. 3BR Suite
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 3-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐎𝐜𝐞𝐚𝐧𝐅𝐫𝐨𝐧𝐭...
Charming Palm Suite at The Imperial Hawaii Resort
Honolulu is waiting for you at this enchanting 1-bedroom apartment. The cozy bedroom features a queen bed, perfect for a good night's sleep after a day of exploring. With 2 bathrooms and a living room with a murphy bed and sofa bed, there's plenty of space for guests to...
Hotel Room Partial Ocean View w/ WiFi and AC - Bamboo Waikīkī Hotel #1101
Castle Bamboo Waikīkī Hotel #1101 - Get the most from your magical Hawaiian experience in this cozy eleventh-floor unit located just blocks from the iconic shores of Waikīkī. With resort-style amenities and a prime location at the Bamboo Waikīkī, you’ll have...
Hilton Vacation Club Kaanapali Beach Club
Lahaina is waiting for you at this 1-bedroom resort. Step into a charming space featuring a king bed and a cozy living room with another king bed, perfect for relaxing after a day of adventure. The bathroom offers both a shower and a bathtub, making it easy to unwind....
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | Whale Watchng! | 3 Units, 4 Bedrooms | KBV ML-2080
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Colony Surf 208 - Studio
Nestled on the Outrigger Canoe Club Beach, this charming, fully furnished studio in Colony Surf is just steps away from the ocean. The unit boasts a complete kitchen and offers wifi & cable for your convenience. Colony surf is located next to the Outrigger Canoe Club,...
Charming 2-bedroom condo with Ocean views!
🌴🏠 Welcome to Your Slice of Paradise in Waikiki! 🏠🌴Available from September 15 - December 31Escape to your dream condo nestled in the heart of Waikiki, where breathtaking ocean and harbor views await you at every turn. This cozy yet luxurious retreat offers...
New Listing! Oceanfront 2bd bliss with a view
Step into paradise at Nohonani 202, a dreamy 2-bedroom, 2-bathroom oceanfront condo nestled on the second floor of a boutique beachfront property. With sweeping views of the sparkling Pacific and the gentle rhythm of the waves as your soundtrack, this is where your...