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.
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 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 Beach Villas PH207 - 2 Bedroom Garden View Penthouse
Upon entering your Wailea Beach Villas PH207, you'll be captivated by the open floor plan, which seamlessly integrates a cozy living room, a quiet den with shoji screen doors, a gourmet kitchen, and a dining area. Sliding doors lead to a lanai equipped with a built-in...
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...
Wailea Elua Village 1604 - 2 Bedroom Oceanfront Condo
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty that Wailea Elua 1604 offers. Evenings offer gorgeous sunsets framed by swaying coconut palms, perfect for a relaxing...
Wailea Beach Villas G302 - 3 Bedroom Ocean View Villa
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking...
Wailea Beach Villas F201 - 3 Bedroom Ocean View Villa
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious 3-bedroom, 3.5-bath villa is perfect for families or couples seeking a serene getaway. Villa F201 is a decorator\'s dream,...
Wailea Beach Villas E202 - 3 Bedroom Garden View Villa
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color...
Wailea Beach Villas D302 - 3 Bedroom Ocean View Villa
Welcome to Wailea Beach Villas D302! Recently renovated, this residence features a custom gourmet kitchen and dining area, offering a luxurious and spacious retreat in one of Maui\'s premier locations. Spanning over 2,900 square feet of indoor and outdoor living, it...
Wailea Elua Village 1301 - 1 Bedroom Oceanfront Condo
Experience the ultimate Hawaiian getaway when vacationing at Wailea Elua 1301. This beautifully designed vacation rental featuring an open floor plan showcases spectacular ocean views from the living room, dining area, and kitchen. The great room is perfect for...
Wailea Elua Village 1203 - 1 Bedroom Oceanfront Condo
Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the prestigious Wailea Elua Village community. This condo offers direct access to Ulua Beach, where guests can enjoy swimming and snorkeling in the gentle...
Wailea Elua Village 1102 - 1 Bedroom Ocean View Condo
This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to the white-sand Ulua Beach that fronts this property. Be one of the first in the ocean in the morning to snorkel the...
Wailea Elua Village 107 - 2 Bedroom Ocean View Condo
Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor residence that offers the perfect blend of comfort and island elegance. With a spacious layout and tasteful décor, this vacation...
Wailea Ekolu Village 706 - 2 Bedroom Ocean View Condo
Towering oleander and bougainvillea grace the front entry of Wailea Ekolu 706. Enjoy views out over the tropical grounds and beyond from the elevated second floor positioning of this condo. During the winter months, you can whale watch right from the lanai as you gaze...
Wailea Ekolu Village 1607 - 1 Bedroom Garden View Condo
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful Wailea. This beautifully appointed condo features calming views of the lush landscapes of the Wailea Blue Golf Course, providing a serene backdrop...
Wailea Ekolu Village 1107 - 2 Bedroom Ocean View Condo
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana\'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Wailea Ekolu Village 1007 - 2 Bedroom Ocean View Condo
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
Wailea Ekahi Village 7B - 1 Bedroom Garden View Condo
Wailea Ekahi 7B is a beautifully appointed vacation rental located within the serene Wailea Ekahi Village. This spacious one-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury. The interior of Wailea Ekahi 7B features a contemporary design with...
Wailea Ekahi Village 54D - 1 Bedroom Ocean View Condo
Wailea Ekahi 54D is a stunning second-floor vacation rental offering breathtaking views of the ocean and West Maui mountains. This one-bedroom, two-bathroom condo boasts panoramic vistas from multiple vantage points, including the living room, kitchen, and primary...
Wailea Ekahi Village 4D - Studio Garden View Condo
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit offers an elevated retreat with a bird\'s eye view of the surrounding tropical landscaping and peek-a-boo ocean views. The 600-square-foot condo is more...
Wailea Ekahi Village 42C - 1 Bedroom Garden View Condo
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to the pool, but offers a quiet sanctuary surrounded by lush greenery. Featuring contemporary, yet comfortable décor –...
Wailea Ekahi Village 3E - 1 Bedroom Garden View Condo
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo offers elevated views over the tropical grounds lush with colorful island landscaping. The vaulted ceilings and oversized...