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.
Updated ocean-view condo with 2 pools & hot tubs - walk to beach / dining
Maui Banyan H404Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The beach is calling to you from across the street at this updated ocean-view condo. For endless sun-soaked leisure,...
FULL OCEAN VIEW, 2nd Floor 2 BR/1 BA, BEST STAND-UP PADDLEBOARDING ON MAUI!
2037 S Kihei Rd, Kihei, HI 96753 US, LOCATED 50' FROM THE BEST SURFING COVE IN South MAUI WITH AN UNOBSTRUCTED OCEAN VIEW, our condo is on the second floor of a FRIENDLY 16 unit complex. From the living room and private lanai you will have VIEWS FROM MAKENA TO THE WEST...
Super cute-great location -close to everything needed for a perfect vacation!
This charming condo provides you with a comfortable, easy and convenient way to enjoy your Maui vacation. This super cute unit is located in an excellent location between Kaanapali and Kahana/Napili. It's across the street from Honokowai Beach Park, so you can walk to...
Maui Eldorado ~ G108 ~ Stay in the Heart of Kaanapali
This is a legally permitted vacation rental according to the County of Maui ordinances.Oceanfront Bliss with Spacious Living, Private Lanai, and Unforgettable SunsetsE Kō Mo Mai! (Welcome!) Embrace the spirit of aloha as you step into your personal sanctuary, where...
Bright and Airy 2BR with Loft in Princeville
Welcome to your Hawaiian retreat—a newly renovated 1,300-square-foot townhouse offering the perfect blend of comfort and island living. This split level unit, backing onto serene green space, provides an exclusive setting for your island vacation.Property Highlights*...
Maui Resort Rentals: Hyatt Residence Club – 2BR Oceanfront Lower Floor VIlla
Exquisite 2 Bedroom Residence With Oceanfront Views at Kaanapali's Newest, Most Exclusive Resort!Proudly perched upon Ka'anapali, one of the world's most beautiful beaches, is the Hyatt Residence Club Ka'anapali. Within the lush borders of this sprawling tropical...
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!
This chic two story 3bdrm/2bth townhouse is located on the west side of Molokai in a quiet residential complex, located right on the beach! Your Molokai island getaway starts here! Offering one of the best locations on Molokai since it's located along one of Molokai's...
Waipouli Beach Resort Beautiful Ocean View Condo
Oceanview! Beautiful! Luxury Gorgeous Oceanview from Living Room, Dining Area and Lanai. Located in Coveted Oceanfront H Building, a one bedroom, two bath condominium at the "New" Waipouli Beach Resort on Kauai. This 2nd floor, oceanview with custom decorated Tommy...
Royal Mauian 309 - Direct Ocean Front, Renovated, Seconds to the Beach, Split AC
A unit renovation will take place in unit 310, next door to this unit, beginning April 7th through September 15th. Please expect noise as well as the potential for dust and debris during work hours. ------------------------------------------Royal Mauian 309 is a newly...
Kehena Moana Kai - Amazing OCEANFRONT Private Retreat
Perched in the sunbelt at the edge of a dramatic oceanfront sea cliff, this honeymooner’s paradise sits in the heart of the lush Puna District rainforest on the Big Island of Hawaii. With two air-conditioned bedrooms, this private cliff house retreat accommodates up...
Hanalei Bay Resort,2 Bedroom, AC Bali Hai & ocean views!
Hanalei Bay Resort unit 7101-2 is a privately owned and cared for two bedroom suite featuring countless amenities to please every guest. The condo features 1,324 square feet of spacious living area, with quality furnishings, with the living room freshly painted and...
Hale Moana - Ocean Front
HALE MOANA AT KOLOA KAI VACATION RENTALSOceanfront Elegance with Panoramic Views on Kauai’s South ShorePerched above the shimmering waters of Kukuiula Bay, Hale Moana is a luxurious oceanfront retreat that blends timeless charm, sophisticated design, and breathtaking...
One of the Most Spectacular Views at Sealodge in Princeville, Kauai
This premium Sealodge vacation rental has one of the most spectacular views in all of Princeville, Kauai! It is perched on an oceanfront cliff with expansive views of the Pacific Ocean, Kauai north shore coastline, Anini reef and Kilauea Lighthouse. From the lanai or...
Orchid House - Pool and Endless Ocean Views!
ORCHID HOUSETA # 087-311-0016-01With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors, granite countertops, slate stone...
Immaculate, Luxury Comfort, Stunning Views - Hawaiian-Chic, Mid-Century Modern
Experience the beauty of Wailea from the moment you arrive in your spacious and stylish villa. Situated in a secluded position of the Grand Champions resort property you can relax on the lanai and take in the views, get to that book you’ve been meaning to read, or...
Well Equipped Kitchen: 3Br Resort Luxury Condo-Private Beach Club, The Villages
COVID-Conscious Cleaning and Management Practices - Free long distance calls to US mainland, Canada and Puerto Rico. Free wireless internet and HBO and Showtime movies. You can Check Out on any date marked in Red on availability calendar.Enjoy a $1 million Luxury,...
Home in Kona, Hawaii
Take it easy at this unique and tranquil getaway. Who doesn’t dream of coming to Hawaii and staying in an original built Hawaiian home set on an acre surrounded by coffee, mango, avocado, papaya, passion fruit trees and much more! Surrounded by Kona coffee farms and...
Hanalei Bay Villas #17 - a 3br/2.5 ba ocean view condominium in Princeville
Hanalei Bay Villas #17 is a beautifully remodeled stand-alone condominium. This luxurious bungalow already had panoramic views of Hanalei Bay and the Hanalei Mountains and the interior reflects the beauty of its surroundings. Beautiful travertine tile floors, smooth...
Hale Kamaole #309 Spacious Ocean View Family Vacation Condo Near Kamaole Beaches
This outstanding condo, situated in the Kihei Hale Kamaole Resort, features ocean views from every room! Watch the whales from our lanai. The two bedroom plus loft, split level unit has over 1300 square feet of living area. Completely furnished in a casual, comfortable...
Plantation Hale Suites H15, Top Floor, AC, Walk to Beach
NOTE: Rates Automatically Discounted from September 15 through December 2025 due to construction repairs on various H-building decks during this time. We apologize for the inconvenience. Work Hours: Monday–Friday, 9:00 AM–5:00 PM.Plantation Hale Suite H15, Top/2nd...
Aloha Hale-Tranquil Ground Floor w/AC Near Beach!
Welcome to our tranquil Maui condo just steps from the beach! We are centrally located in Kihei, only 20 minutes from the airport and minutes from the best beaches, shops, and restaurants that South Maui has to offer!If you decide to prepare your own meals, our...
🏖️Updated Townhome | Ocean View | vrKCV🏖️
vrKCV - Na Hale O Keauhou D3, Professionally Managed by Kona Coast VacationsWelcome to Your Perfect Home Base in Na Hale O Keauhou!Experience the charm of this beautifully updated townhome in the serene and highly sought-after Na Hale O Keauhou complex. This gated...
Oceanfront Remodeled Condo! Can't Beat Views!! Air Conditioning
Premium 2 Bedroom/2 Bath ocean front condo with amazing ocean views and the best location in Central Maui (half way between Lahaina and Kihei). Enjoy the best views of Maalaea Bay from your large, private Lanai -- see the whales jumping, and enjoy beautiful sunrises and...
Ocean View Villa in Kahana, Maui
Experience the ultimate comfort and relaxation in our beautifully adorned Maui haven, Kahana Villa F404. This exquisite condo boasts an array of personalized touches that will leave you feeling right at home. Indulge in the breathtaking vistas of the Pailolo channel and...
Sea Village Oceanview Condo
Unwind with modern comforts, including a flat-screen TV with cable, high-speed WiFi, and a fully equipped kitchen perfect for preparing island-inspired meals. Step outside to soak up the sun in the oceanfront complex, where you can lounge by the pool, take a dip in the...
City-View Waikiki Beach Condo - Free Parking!
Who needs an ocean view when you can have majestic green mountains, blue skies, and lively street views from the 17th floor of Ilikai condo? Plus, you might even catch a rainbow or two! This cozy 500 sq. foot condo may not have a wall separating the bedroom from the...
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Under the Warm Maui Sun - Permit#BBKM\2016\0004 Due to cancellation last moment special forMon, Oct 31 - Thu, Nov 10, 2022 $350/nightRegular rates 2022: April 1 - December 27 2022$410/nite for 2 personsWinter rates 2023: January 3 - March 31 $490/nite for 2...
BEAUTIFUL! Cooks Landing at Hali'i Kai 18H
Welcome to Cooks Landing! A 3 bedroom 2 bath ground floor luxury villa (18H) in the prestigious Hali'i Kai gated condominium community of Waikoloa Beach. Includes gourmet kitchen, full sized washer and dryer, detached garage plus another reserved parking space. Access...
Charming 2-bedroom cottage with a hot tub. 5 Min to Volcanoes National Park!
Welcome to Kolea Cottage - where comfort meets environmental responsibility. Wake up to the peaceful sound of native birds singing surrounded by miles of lush native Hawaiian rainforest. It’s the perfect place to stargaze and relax in the private hot tub after a day...
1 Bedroom at Oceanfront Resort Kapaa
This spacious one-bedroom resort suite measures approximately 628 square feet. You will enjoy a queen bed in the master bedroom and one queen Sleeper Sofa/Murphy bed in the living area.. Additional amenities include a full kitchen and dining area and a balcony. Maximum...
Kiahuna Plantation Oceanfront Renovated Ground floor Steps to ocean W/D in unit
Guest to pay onsite management Castle Resorts direct at check in/out for required cleaning. Full check out cleaning for 1 bedroom units for 2025 is $268.00 plus 18.712% tax effective 1-1-26 Any stays over 10 nights also require a full mid stay cleaning at a cost of $110...
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Our Maui home is quiet vacation escape. The upstairs has a master bedroom with a California King mattress with a bathroom having a Jacuzzi tub separate from shower. The secondary bedroom also has a California King mattress with a 3/4 bath. The kitchen has all amenities...
Na Hale 3: Exclusive Family Retreat with Private Pool and Resort Privileges
Welcome to Na Hale 3 at Pauoa Beach Club, an embodiment of exquisite indoor/outdoor living nestled in the Mauna Lani Resort, Hawaii's premier destination. This single-family haven is a symphony of luxury and natural beauty designed to offer an unparalleled vacation...
Makana Nui - Beachfront Home on Hanalei Bay
Welcome to the Makana Nui, located on the famous Weke Road in Hanalei. This home sits directly on the beach and is just a short walk through your private lawn to the sand. The picturesque Hanalei coastline remains relatively undeveloped and provides breathtaking views...
Relax, with breathtaking ocean views. Makaha 1-bedroom condo near Ko Olina
Nestled in the town of Makaha, our 1-bedroom condo offers a tranquil retreat for your Hawaiian getaway. As you step inside, you'll be greeted by a gorgeous ocean view! A kitchenette, complete with a stove, oven, refrigerator, and all the necessary appliances and...
Maui Resort Rentals: Honua Kai Konea 613 - Upgraded 6th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan
Konea 613 is amongst a class of the most sought after 2 bedroom floor plans at Honua Kai. What distinguishes this column in the Konea interior are the direct ocean views from virtually every interior vantage point of the suite. This premier two-bedroom boasts a spacious...
Luxury Panoramic Ocean Views!
Summary:This beautiful and stylish remodeled home is perfect for group or couples vacations! You will be very comfortable in this large and upscale 2 bedroom 3 full bath home that is completely renovated!We are located in the Kapalua Ridge Villa Community. Only a 6 min...
Heart of Princeville w/AC minutes from everything!
Escape to our North Shore Kauai retreat in Princeville! A haven of beauty awaits you, with leisurely walks along Makai Golf Course offering breathtaking mountain and waterfall views. Experience mesmerizing sunrises, stunning sunsets, and starry nights in the tranquil...
Oceanfront Vacation Rental in Kihei Maui
Looking forward to relaxing on the lanai, enjoying the most beautiful view - morning, noon and night? Want to enjoy incredible sunsets, watching the sky burst with a fiery glow of mesmerizing color? Would you like to open all the windows and hear the sound of the waves...
Luxury Waikiki condo - 28th floor! Stunning views, convenient location, parking
Allure is one of the most luxurious private condominiums in Waikiki. The grounds, pool, and other amenities rival the resort hotels, but you get even more space, privacy and freedom. This property is ideal for couples or families seeking to feel at home in Waikiki for...
Turtle Bay Hale Lani by RedAwning
This lovely 1 bedroom w/loft upgraded unit has new kitchen cabinets &appliances, ceramic tile floors and granite countertops. The living room has aflat-screen TV, internet and WIFI, and ceiling fan. Window a/c in the livingroom and the bedroom. Reserved parking spot,...
Maui Eldorado K-106 - April Specials!
Centrally located in the heart of Ka'anapali, Maui Eldorado Kaanapali is the perfect place to enjoy your Maui Vacation. This ground-floor end unit with an elevated garden view is very close to the front desk and outdoor parking - handy for unloading luggage and...
Kailua Beachfront Vacation Home with Pool
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1783. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
KaMilo #503 by Gather: Luxury Mauna Lani Retreat Near Golf & Beach
Welcome to Mauna Lani KaMilo #503, a serene three-bedroom, three-bath villa tucked within the private gates of Mauna Lani Resort on Hawai‘i’s Big Island. Thoughtfully designed for seamless indoor-outdoor living, this residence combines island-inspired luxury with...
Maui Resort Rentals: Honua Kai Hokulani 506 - Spacious 5th Floor 2BR Corner Suite w/ Direct Ocean & Mountain Views!
Maui Resort Rentals is proud to bring you this 2BR Partial Ocean View Suite at the Honua Kai Resort, newly launched on May 7th, 2025 to start taking reservations for check-ins on June 7th, 2025!Just two stacks from oceanfront, this highly sought-after 2BR/2BA corner...
Beautiful Ocean View on Quiet Side of Honua Kai
NO RESORT OR PARKING FEES WHEN BOOKING WITH US!Honua Kai is a Four Star resort with four pools, five spas, a fitness center, Aina Gourmet Market, and beachfront Dukes Restaurant on premises. Our one bedroom condo (unit 514 in The Hokulani Building) has a partial ocean...
Lovely Palms at Wailea condo, spacious, large lanai, close to beach! Full A/C
Located in the highly desirable Palms at Wailea, this delightful condo offers a relaxing retreat for guests. This spacious condo sleeps 4 with 1 bedroom featuring a king bed and a queen size sofa bed in the living room. It also has two full bathrooms. It's upstairs...
Maui Resort Rentals: Honua Kai – 6 Total Bedrooms, Ocean Views, 3300 Combined Sq Ft, Sleeps up to 18!
This one-of-a-kind 6 bedroom offering combines one 2br ocean view suite with two 2br partial ocean view suites located directly across the hall to create a tandem package with 3300 sq ft of interior living space and the capacity to accommodate up to 18 guests. Enjoy the...
Luxury Ko Olina Beach Rental Panoramic Ocean View 3BR 3BA 8th floor 2 parking
Imagine yourself in a world-class Oahu, Hawaii oceanfront resort in Ko Olina beach rental bliss with exotic woods, natural stone, and an expansive lanai. Imagine as you lie down on a bed of total luxury. You sink down into silky softness that cuddles you as you are...
🏖️NEW LISTING | Brand New Renovation! | Professionally Managed | vrKCV
vrKCV - Mauna Lani Fairways 1601, Professionally Managed by Kona Coast VacationsFeel the Aloha Spirit and relax in tropical paradise at Sandy Feet Retreat! Newly renovated in the summer of 2022, enjoy the modern Hawaiian vibe in this two-bedroom, two-bathroom townhome...