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.
Enjoy ocean views, refined interiors, and an infinity pool that embodies Kauai’s tropical beauty.
Perched on Kauai’s North Shore, this 4,000 sq. ft. villa by architect Mark Eyler blends Hawaiian, Balinese, and modern design. With sweeping ocean views, elegant interiors, and an infinity pool overlooking lush tropical scenery, it’s the perfect blend of island luxury...
New Listing! Modern, cozy 2bd getaway by the Shore
Welcome to Kahana Manor 208 — Your Relaxed West Maui Retreat. Perfectly located in the heart of Kahana, this 2-bedroom, 2-bathroom condo is ideal for families, couples, or friends. With two queen beds and a queen-size sleeper sofa, it comfortably sleeps up to six...
Oceanfront Penthouse 2 bed with AC in Kona at Banyan Tree Condos on Alii Drive
Your Kailua-Kona adventure begins with a gorgeous oceanview from the lanai, living room, kitchen, and even primary bedroom. Watching the surfers, sealife, and sunsets are amazing! Guests will unwind in a fabulous space featuring one king bed and one queen bed, perfect...
Brand New, Luxury Volcano Hideaway, Minutes from National Park
Escape to this Brand-New Luxury Hideaway in Volcano.This brand-new, 575 sq ft fully furnished hideaway offers a romantic and luxurious escape in the heart of quiet Volcano. Nestled amidst native forests, häpu'u ferns, and wild ginger, this private retreat is just...
Large studio/bedroom unit in Haleiwa with beach access and next to the park.
Haleiwa is waiting for you at this studio unit. Inside, guests find a nice space featuring a cozy twin bed and a clean bathroom with a refreshing shower, all new renovated. The layout is simple and inviting, perfect for a relaxing getaway. Whether you’re unwinding after...
Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
Welcome to Wailea Beach Villas Penthouse K107 - A luxurious and spacious 2-bedroom, 2-bath with a den that functions as a workspace or third bedroom offering 1,899 square feet of elegant island living.Perched directly above the upper pool, this villa enjoys lush...
Waikoloa Colony Villas 1702
Luxurious 3 Bedroom Villa with Stunning Views Welcome to your dream getaway at Waikoloa Colony Villas 1702! This freshly renovated 3-bedroom, 2.5-bath villa offers a perfect blend of modern amenities and breathtaking natural beauty. With stunning views of the Kohala...
Pali Ke Kua Beautiful Garden, Mountain View Condo with AC & Beach access!
Your Kauai adventure begins at this terrific 2-bedroom condo. Absolutely the best location in the heart of Princeville...can you say paradise!This condo is beautifully decorated with high end furnishings to help you relax while you take in commanding garden and...
North Shore Condo At Turtle Bay
Escape to the North Shore in this furnished 1-bed, 2-bath Turtle Bay retreat. Enjoy a large bedroom with king bed and private bath, open living area, full pull-out sofa, and private covered lanai. Located in a gated community with pools, BBQ areas, tennis courts,...
NEW! KBM Resorts Niki Lani Condo | FREE CAR | Kuilima Estates | 3-Bedroom Condo at Turtle Bay! KUL-W11
** 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...
Oceanfront, Friendly Sea Turtles, Epic Snorkeling!
Summary:Treat yourself to timeless Old Hawai‘i elegance. This bright and breezy 4th-floor oceanfront 2-bedroom condo—with secure elevator access—offers stunning garden and ocean views as your front-row seat to paradise. Perfectly perched above the turquoise waters of...
Spacious Oceanfront 3/3 Villa Kahana Outrigger 4A1
You can't get closer to the Pacific Ocean than this! Situated on the West edge of Maui between the renowned golf course Kapalua and Ka'anapali beach, you are perfectly positioned to access Maui's top beaches, elite golf courses, shopping, restaurants, & tourist...
Barefoot Beach House at Richardson's Beach
Barefoot Beach House is located directly across the street from Richardson Beach Park, Hilo's premier beach. The house was built in 1938 and was once the area's post office. It is now a beautifully updated and fully furnished cottage perfect for your dream vacation. The...
Kilohana Makai - 4 Bedroom Luxury Home w/Private Pool
Discover the perfect Garden Island retreat at Kilohana Makai, Hawaiian for ''Unsurpassed Excellence near the Ocean.'' This four-bedroom, three-and-a-half-bath villa truly lives up to its name, offering a picture-perfect tropical family retreat on Kauai’s sunny south...
Hale Wa'a - 4-bedroom, 3.5-bathroom vacation rental in the Prestigious Kukui'ula
Welcome to Hale Wa'a (House of the Canoe), a stunning 4-bedroom, 3.5-bathroom vacation rental nestled in the prestigious Kukui'ula community on Kauai's southern coast. This brand-new modern home, located in the Kaulu neighborhood, seamlessly blends contemporary design...
Hale Anuenue - 3 Bedroom Luxury Home w/Private Pool
Settle into a blissful sense of calm at Hale Anuenue, which means ''House of the Rainbow'' in Hawaiian. This three-bedroom, three-and-a-half-bath villa features beautifully appointed interiors featuring contemporary coastal décor and expansive grounds, allowing you and...
Stunning four-bedroom villa at The Lodge at Kukui'ula
This stunning four-bedroom villa at The Lodge at Kukui'ula is the ideal Kaua'i getaway. The airy, open floor plan opens onto a stunning outdoor living area with a private plunge pool, lounge area, outdoor kitchen and dining area. Inside, enjoy high ceilings, a large...
Lodge at Kukui'ula Villa 9
Villa 9 at The Lodge at Kukui'ula is a luxurious four-bedroom retreat designed for discerning travelers seeking an exceptional Hawaiian experience. This stunning residence offers an unparalleled blend of comfort, privacy, and island-inspired living.The villa features a...
Lodge at Kukui'ula Villa 7
Look no further! This four-bedroom villa 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,...
The Lodge at Kukui‘ula - Villa 1
Villa 1 at The Lodge at Kukui'ula is a discerning traveler’s dream vacation home in Koloa, Kaua'i. With three bedrooms in the main house featuring a king bed in the primary and second bedroom and two twins that can convert into one king in the third bedroom, as well as...
The Lodge at Kukui‘ula - Cottage 1
The three-bedroom cottages 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...
The Lodge at Kukui‘ula - Bungalow 16
Bungalow 16 at The Lodge at Kukui'ula offers a luxurious retreat on the stunning south shore of Kaua'i. This exquisite three-bedroom, three and a half-bathroom vacation rental is designed to accommodate up to six guests, making it ideal for families or groups seeking an...
The Lodge at Kukui‘ula - Bungalow 8
Discover the luxurious Lodge at Kukui'ula Bungalow 8, a stunning one-bedroom retreat nestled in the heart of Kaua'i's most exclusive resort community. This meticulously designed bungalow offers guests an intimate and sophisticated Hawaiian getaway, blending contemporary...
The Lodge at Kukui‘ula - Bungalow 4
The Lodge at Kukui'ula, located on the picturesque south shore of Kaua'i, offers a unique blend of luxury and comfort in its Bungalow 4. This one-bedroom bungalow spans approximately 1,275 square feet and is designed with an authentic plantation-style architecture that...
Sea Turtle Suite - Steps from Carlsmith Beach!
Explore nature - marine life, lush jungle greenery, palm trees, and paradise in Hilo on Hawaii Island. Sea Turtle Suite, unit 403 is located on the 4th floor at Maunaloa Shores oceanfront condo in Hilo, Hawaii. The screened-in lanai brings a nice sea breeze from the...
Hilo Bayview - Modern family-friendly 4-bedroom home with views & office
Located in Hilo, this charming house offers 4 bedrooms with a mix of 1 king, 2 twin, and 1 queen beds. With 3 full bathrooms, guests will feel right at home. With great views and only a short distance from downtown Hilo, Hilo airport, downtown shopping, restaurants, and...
Stunning Kaanapali Oceanfront Mahana 1107!
Welcome to Mahana 1107! Located on the eleventh-floor, this one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands! Highlights include hardwood floors, 55` HD TV, and sectional with queen sofa bed. Kitchen has...
Oceanview Paradise at Kiahuna Plantation #207 w/ AC in Beautiful Poipu!
Brand new owners! Take advantage of our discounts for our new guests.Welcome to your slice of Hawaiian paradise at Kiahuna Plantation Unit 207 in sunny Poipu, Kauai! Nestled among 35 acres of lush tropical gardens, this spacious two-bedroom, two-bath condominium offers...
Oceanview King Studio | Maui Banyan, Walk to 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.Enjoy your Maui getaway in this top-floor Maui Banyan studio featuring ocean views from your private...
Sunset Ocean Views & Pool • Spacious 4BR, Deck & AC
Welcome to your slice of paradise! This newly updated 4-bedroom, 2-bath vacation retreat offers the ultimate Hawaiian experience, featuring: -Large open deck with breathtaking sunset and ocean views-A renovated kitchen fully equipped with cookware and essentials-A...
Waikiki - Resort amenities for condo prices, just steps from the beach!
Enjoy your stay at this condo in beautiful Waikiki, at the iconic Ilikai Hotel where the King himself, Elvis stayed. This cozy retreat features 1 bedroom with 2 queen beds and a full-sized pullout sofa bed, perfect for a small group of guests, or a solo traveler....
Kona Islander Inn#305: Downtown Kona, Walk to everything, Affordable Studio
Welcome to "Pacific Blue" your charming studio in the heart of downtown Kailua-Kona! This adorable unit offers the perfect blend of comfort and convenience, making it an ideal getaway for your Hawaiian vacation. Just steps away from the vibrant shops, restaurants, and...
Charming Beachside Garden Vistas
Summary:**Bright, modern, and spacious—**this completely remodeled one-bedroom, two-bath condo has been carefully designed to elevate every part of your Maui experience. From the moment you enter, the space radiates an inviting sense of calm and sophistication. Clean...
New Owners! 3-Bedroom Home with Sunset Views! Beach Club/Pool/Fitness Center
Luxurious and family friendly vacation home in The Villages at Mauna Lani! Enjoy captivating sunsets with partial ocean views from the main floor lanai. Flow effortlessly to the indoor living area with spacious living, dining, and chef's kitchen. Each bedroom features...
Stunning Views & Swaying Palms from your 5th-Floor Oceanfront Retreat
Welcome to your peaceful Maui getaway—a beautiful 5th-floor oceanfront condo with sweeping views of KahoÊ»olawe and LÄnaÊ»i islands. From your private lanai, watch palm trees sway over sparkling blue waters and feel the gentle quiet that defines this part of West Maui.Our...
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...
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...
"Hale Opaka" | Beach Access, 6 BR, 2 Kitchens, A/C
Vrbo Premiere Host new rental: Experience the ultimate Hawaiian getaway in this spacious oceanfront estate just steps from the beach. This unique property combines upper and lower units connected by external stairs for maximum space, privacy, and breathtaking ocean...
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...
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
Welcome to Nalu Lani, your “heavenly wave” retreat on Kauai’s breathtaking North Shore. Perched on the bluff at Sealodge in Princeville, this beautifully remodeled one-bedroom condo offers panoramic ocean views that will take your breath away. From your private lanai,...
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...