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.
Aloha Experience in a Comfortable Waikiki Studio: Hotel Amenities: Pool, Hot Tub
A clean small studio apartment where urban meets hotel. This comfortable space is ideally located in a condo/hotel building in a corner of Waikiki near Convention Center, dining & shopping, attractions and beach. Location allows you to live like a local and enjoy rest...
Mystic Mermaid Island Retreat! Entire Home
This home is not your typical VRBO, this home is designed for guests who appreciates CLEANLINESS, COMFORT, CARE, SAFETY AND QUALITY! Escape to Your Mystic Mermaid Island Retreat, your private, spacious oasis near Oʻahu’s majestic mountains! NO neighbors behind the home...
Laule‘a #13 by Gather – Mauna Lani 4BR Villa w/ Golf Frontage, Private Pool/Spa
Welcome to Laule‘a at the Mauna Lani Resort #13, a refined 4-bedroom, 4.5-bathroom retreat on the Kohala Coast where modern elegance meets effortless island life. With golf course frontage, panoramic views of Mauna Kea, and a private pool and spa framed by tropical...
New Modern Hawaiian 2-bedroom house in Kapaʻa with amazing ocean/mountain views
Modern Beachside Escape in Kapa‘a – Steps from the Ocean!Welcome to your island getaway! This beautiful, newly built 2-bedroom home in Kapa‘a is just steps from the beach. Designed with modern island style, it features open and airy living spaces, a fully equipped...
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 of...
Walk to Beach | Pool + AC | Heart of Kihei
Welcome to your tropical retreat at Kalama Terrace in South Kihei — a bright, comfortable 1-bedroom, 1-bath condo perfectly situated for exploring Maui’s best beaches, restaurants, and activities. This clean and well-stocked unit offers the ideal mix of comfort,...
Maui Resort Rentals: Kaanapali Alii 241 - Interior Courtyard 2BR with Stunning Ocean Views from Nearly Every Room!
Maui Resort Rentals is proud to present this luxurious 2BR/2BA suite at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach. Newly launched on October 13th, 2025, the suite is now open for reservations with first arrivals beginning on November 10th, 2025.Suite...
Oceanfront Paradise: Breathtaking 3bd/2ba with Panoramic Views of Hilo Bay
Welcome to Hilo Hale, an oceanfront sanctuary with panoramic views of Hilo Bay.Built around the sweeping vistas of the bay, this light-filled home offers a seamless blend of comfort and natural beauty. From the moment you arrive, the rhythm of the waves and the changing...
Perfect Getaway, Steps to the Ocean, Puamana 145-4
Summary:Aloha and E Komo Mai (Welcome) to your Maui retreat at Puamana 145-4! Nestled in the heart of the beloved Puamana community, this well-appointed 2-bedroom, 2.5-bath townhouse offers the perfect balance of comfort, convenience, and tropical charm. With direct...
Oceanview 1 Bedroom at Lawai Beach Resort, modern and updated!
Our newly updated ocean view condo on the 2nd floor of Lawai Beach Resort is ready for you!Recently updated with chevron flooring, new bathroom vanity, refreshed kitchen cabinets (new appliances coming in October), all new furniture...we are ready to host you!Lawai...
Nalu Lani | Ocean Bluff Haven w/ Breathtaking View
Summary:Nalu Lani | Stunning Oceanfront Hideaway with Panoramic Ocean Views! Unwind in island luxury near Hanalei Bay, pristine beaches, golf, and golden sunsets.The Space:Now offering new All-Inclusive Pricing with NO GUEST SERVICE FEES! Welcome to Nalu Lani, your...
Wailea Point | 3203 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays
Wailea Point #3203 offers a luxurious and serene retreat with stunning ocean views, located in the exclusive gated community of Wailea Point. This elegant condo is perfect for those seeking privacy and a minimum stay of 30 nights, providing an ideal setting for a...
Wailea Grand Champions 97 - 1 Bedroom Golf Course View Condo
Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite property combines elegant design with modern amenities to provide a truly exceptional getaway experience. Upon arrival at Wailea Grand Champions 97,...
Wailea Grand Champions 95 - 3 Bedroom Golf Course View Condo
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant reminder that you are vacatioing in paradise. This vacation rental offers a perfect blend of comfort and luxury, making it...
Wailea Grand Champions 84 - 3 Bedroom Golf Course & Partial Ocean View Condo
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. This spacious three-bedroom, two-bathroom condo offers views out over the Wailea Blue Golf Course as well as a partial ocean view. It\'s size and...
Wailea Grand Champions 73 - 1 Bedroom Partial Ocean View Condo
Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, and stunning views in the heart of Wailea, Maui. As you enter the villa, you\'re greeted by a bright and spacious great room, ideal for relaxation...
Wailea Grand Champions 71 - 2 Bedroom Golf Course & Partial Ocean View
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and private lanai. This spacious two-bedroom, two-bath condo comfortably accommodates up to six guests, providing ample room for...
Wailea Grand Champions 43 - 2 Bedroom Garden View Condo
Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with breathtaking views and unparalleled comfort. This elegantly designed property is ideal for those seeking both relaxation and adventure on the...
Wailea Grand Champions 31 - 2 Bedroom Golf Course View Condo
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and convenience in the heart of Wailea. This two-bedroom, two-bathroom condo features modern upgrades including granite countertops, new cabinetry, and...
Wailea Grand Champions 183 - 2 Bedroom Garden View Condo
Welcome to Wailea Grand Champions 183, a luxurious vacation rental that perfectly blends comfort and style in the heart of Maui\'s paradise. This stunning two-bedroom, two-bathroom retreat offers an exceptional experience for discerning travelers seeking a memorable...
Wailea Grand Champions 159 - 3 Bedroom Golf Course View Condo
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This ground-floor condo offers a spacious layout with three bedrooms and two bathrooms, making it ideal for families or groups...
Wailea Grand Champions 152 - 1 Bedroom Golf Course View Condo
Relax on your private lanai at Grand Champions #152, perched upon the second-floor, and enjoy views of manicured fairways, putting greens, and tee boxes as golfers tackle the Wailea Golf Course. This vacation rental is ideally situated to showcase Maui’s natural...
Wailea Grand Champions 111 - 2 Bedroom Garden View Condo
Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal choice for families or friends traveling together. The first bedroom features a comfortable king-sized bed, while the second...
Wailea Grand Champions 104 - 1 Bedroom Golf Course View Condo - PLATINUM
Villa 104 at Wailea Grand Champions Villas is a beautiful Maui vacation rental that offers an exceptional blend of style, comfort, and convenience. This modern and hip condo boasts stunning golf course views and thoughtfully curated interior design elements that create...
Wailea Beach Villas PH512 - 3 Bedroom Ocean View Penthouse
Penthouse 512 at Wailea Beach Villas offers an unparalleled top-floor experience with expansive ocean and island views, ideal for a Hawaiian dream vacation. This 2,300-square-foot home features a wrap-around lanai, providing one of the most breathtaking views in the...
Wailea Elua Village 910 - 1 Bedroom Garden View Condo
Wailea Elua Village 910 is a stunning one-bedroom, one-bathroom vacation rental located in the exclusive Wailea community on Maui. This beautifully remodeled condo offers a luxurious retreat a short stroll to one of the best snorkeling beaches on Maui. Located on the...
Wailea Elua Village 905 - 3 Bedroom Garden View Condo
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury, making it an ideal retreat for families or friends traveling together. This condo is...
Wailea Beach Villas PH502 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual décor. Your private elevator...
Wailea Elua Village 904 - 3 Bedroom Ocean View Condo
Wailea Elua 904 is a stunning vacation rental property that offers a luxurious island getaway. Nestled within the upscale Wailea resort community, this spacious three-bedroom, two-bathroom condominium provides guests with all the comforts of home combined with the...
Wailea Beach Villas PH411 - 2 Bedroom Ocean View Penthouse
Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of...
Wailea Elua Village 804 - 3 Bedroom Ocean View Condo
The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island of Maui. From the moment you step inside this stunning, 1,700-square-foot condo, you\'re enveloped in a sense of luxury and tranquility. The...
Wailea Beach Villas PH410 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kaho’olawe, Molokini and Lana\'i. From your private elevator landing, the suite opens...
Wailea Elua Village 708 - 2 Bedroom Ocean View Condo
Wailea Elua Village 708 is a luxurious two-bedroom, two-bathroom vacation rental located in the prestigious Wailea community on Maui\'s southern coast. This beautifully remodeled condo offers a serene retreat, accommodating up to six guests, making it ideal for families...
Wailea Beach Villas PH406 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 406 is desirable for its remarkable Pacific Ocean and Island views. This upscale penthouse vacation rental features two bedrooms, two bathrooms, exotic hardwood furnishings, an incredible antiquities collection, and an amazing ocean view....
Wailea Elua Village 705 - 2 Bedroom Garden View Condo
Wailea Elua 705 is an exquisite vacation rental located on the stunning shores of Maui. This newly renovated, two-bedroom, two-bathroom beach house inspired condominium offers a spacious layout ideal for families or groups of friends seeking a luxurious getaway. With...
Wailea Beach Villas PH402 - 2 Bedroom Ocean View Penthouse
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
Wailea Beach Villas PH309 - 3 Bedroom Ocean View Penthouse
Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private...
Wailea Elua Village 2402 - 1 Bedroom Ocean View Condo
Wailea Elua Village 2402 is an exquisite ocean-view second-floor condo located in the prestigious Wailea area of Maui. This elevated condo with vaulted ceilings enjoys great views out over the South Maui coastline, especially remarkable during whale season, since you...
Wailea Beach Villas PH307 - 2 Bedroom Ocean View Penthouse
In Wailea Beach Villas PH307 you can immerse yourself in luxe tropical comforts blended with blue ocean views. This delightful Maui ocean view vacation residence will cultivate long lasting memories and leave you feeling rejuvenated upon departure. Centrally located on...
Wailea Beach Villas PH306 - 2 Bedroom Ocean View Penthouse
Settle into your very own slice of Maui paradise with a stay in Wailea Beach Villas PH306. This exquisite two bedroom, two bathroom penthouse with exceptional ocean and island views are sure to inspire the luxury, comfort and serenity you deserve. Thoughtfully designed...
Wailea Elua Village 2104 - 2 Bedroom Garden View Condo
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired aesthetic, this condo blends comfort with contemporary style, making it an ideal getaway for families or groups of friends....
Wailea Beach Villas PH210 - 2 Bedroom Garden View Penthouse
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish...
Wailea Elua Village 2012 - 1 Bedroom Ocean View Condo
Wailea Elua Village 2012 is a luxurious vacation rental located in the stunning Wailea area of Maui. This one-bedroom, two-bathroom condo offers an ideal retreat for couples or small families, providing a perfect blend of comfort and elegance. The property is part of a...
Wailea Beach Villas PH209 - 3 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the family pool. This open and airy vacation rental is designed for relaxation and leisure, featuring an expansive tiled great...
Wailea Elua Village 2006 - 2 Bedroom Ocean View Condo
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom, two-bath condo offers an ideal retreat for families or friends seeking a relaxing island escape. The residence boasts a...
Wailea Beach Villas PH201 - 3 Bedroom Garden View Penthouse
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements everywhere you look. This contemporary vacation residence spans 2,500 square feet and captures the true allure of vacationing in...
Wailea Elua Village 2004 - 1 Bedroom Ocean View Condo
Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui\'s southern coastline. This one-bedroom, one-bathroom condominium offers an ideal retreat for couples or small families, featuring a spacious layout that maximizes comfort and ocean views...
Wailea Elua Village 1704 - 2 Bedroom Oceanfront Condo
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious two-bedroom, two-bathroom corner unit spans approximately 1,600 square feet and comfortably accommodates up to six guests,...
Wailea Elua Village 1703 - 2 Bedroom Oceanfront Condo
Elua 1703 is a distinctive oceanfront vacation rental, perfectly situated directly in front of the renowned Ulua Beach and the Wailea Beachfront Walking Path. What sets it apart is its unique privacy, surrounded on three sides by lush, meticulously landscaped gardens...
Wailea Beach Villas PH111 - 2 Bedroom Garden View Penthouse
Curated with our guests in mind, Wailea Beach Villas PH111\'s outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located...