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.
Valley Isle Resort 1201 – Stunning, Newly Updated Oceanview Getaway in Kahana
Valley Isle Resort 1201 – Stunning, Newly Updated Oceanfront Top-Floor Corner Unit in KahanaWelcome to Valley Isle Resort 1201, a premier top-floor, corner unit offering sweeping ocean views and a dramatic backdrop of the West Maui Mountains. This newly updated...
NEW! KBM Resorts | FREE CAR | Kapalua Bay Villa | Oceanfront | 1-Bedroom Condo with Amazing views! KBV-35G2
** 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...
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...
Lovely oceanfront 3-bedroom, first floor corner unit
Vacation with the whole family at our lovely Maalaea oceanfront, ground-floor unit end unit with outstanding views, five windows from the sides plus 2 sliding glass doors to the ocean side, wonderful amenities, and a perfect laid-back location. Plenty of room in this...
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...
Wailea Beach Villas Penthouse K107 – Maui Luxury with Island Serenity
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...
Renovated spacious condo in Waikiki with central AC in waterfront building
Your cozy getaway awaits in Honolulu at this charming condo. Step inside to find a bright, comfortable space with a spacious king size bed, large screen TV, a large size closet for all your belongings, and a refreshing central air conditioner. The condo features one...
NEW! KBM Resorts | FREE CAR | Hali'i Kai | Ocean View | 2-Bedroom Luxury Condo! HLI-7A
** 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...
Private Luxury Home at Waikoloa
Discover this 3-bedroom house in Waikoloa. Step inside and enjoy a cool retreat where comfort meets charm. With two bathrooms, getting ready is a breeze for guests. The space feels inviting and spacious, perfect for relaxing after a day of adventure. Whether you’re...
Ground-Floor Gem in Wailea Ekahi Village
Discover true island elegance in this beautifully updated ground-floor residence at Wailea Ekahi Village, one of Maui’s most sought-after beachfront communities for vacation renters. Set within 34 acres of lush, low-density tropical gardens, the property offers direct...
Oceanfront with Panoramic Views I Maalaea Kai 416
Wake up each morning to sweeping panoramic ocean vistas visible from the lanai and the expansive floor-to-ceiling windows. From November through March, witness the unforgettable sight of humpback whales breaching just offshore, while sea turtles make their daily...
Cozy 2-bedroom apartment in Honolulu
Consider this apartment your home away from home while you visit Honolulu. With 2 bedrooms featuring a queen and king bed, this cool space is perfect for guests looking for a comfortable stay. Fall in love with Honolulu and enjoy the magic it has to offer.
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...
Beautiful Pali Ke Kua Garden/Mountain View Condo w/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...
Amazing 3-bedroom house with AC in Bayview @ Poipu Kai - Ocean View
Our private home offers convenient access to Poipu's best attractions. Located just a short stroll from The Grand Hyatt and Shipwreck Beach, it provides easy access to white sand beaches, fine dining, and local attractions.As part of the exclusive Poipu Kai Resort,...
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,...
12th Floor Waikiki City & Mountain Views! Full Kitchen! Walk to Beach!
Ilikai Marina #1299 – 1765 Ala Moana Blvd.Discover this spacious and beautifully upgraded corner-end unit offering stunning mountain and city views, located just steps from the ocean at the Ilikai Marina. Enjoy the tradewind breezes on either of your 2 private lanais....
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...
Oceanfront Ground-Floor Condo | Walk-Out Lanai + Pool
Step out of your lanai and into paradise, this newly listed ground-floor condo offers direct oceanfront views, breezy indoor-outdoor living, and access to the pool, BBQs, and lawn just steps from your door. Perfectly located between KÄÊ»anapali and Kapalua, enjoy sunsets...
Kona Isle B2 No Stairs, Beautiful unit, AC in bedroom and living room!
Kona Isle B2 — Serene Ground-Floor Escape with Modern ComfortsWelcome to Kona Isle B2, your peaceful island retreat on the sunny Kona coast. This beautifully updated ground-floor condo pairs comfort and convenience with a touch of Hawaiian charm — just steps from the...
Charming 2BD + Den Retreat in Princeville – Near Hanalei Beach
Stay near the beaches and beauty of Kaua‘i’s North Shore at Casa La Ola, a modern 2-bedroom + den condo in the heart of Princeville. Enjoy ocean views, walk to Queen’s Bath, and unwind in the pool and spa just steps from your door.Located in one of Princeville’s newest...
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...
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...
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 - 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...
Maui Resort Rentals: Kaanapali Alii 352 - Remodeled 5th Floor 2BR with Ocean and Mountain Views!
Maui Resort Rentals is proud to present this luxurious 2BR/2BA residence at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach—newly launched on October 31st, 2025 to start taking bookings for check-ins starting April 27th, 2026!This 5th-floor corner suite...
Golf Villas Mauna Lani 3 bedroom townhome, Stunning volcano views, Private beach
Stay comfortably in the Mauna Lani Beach Resort at this 3-bedroom townhome. Fully equipped kitchen, living spaces with huge 80 in TV with recliner movie theatre chairs. Each bedroom offers a unique sleeping arrangement with a king, queen, and twin bed. Enjoy the...
White Sands Village#313: Direct Beachfront, Top Floor Corner, Best Location
White Sands Village #313 — Beachfront, Top Floor. Corner Unit Luxury at Kona’s Most Iconic BeachWelcome to White Sands Village #313, the best of the best at one of Kailua-Kona’s most sought-after oceanfront destinations. Perfectly positioned as a front-row, end-unit...
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...
Oasis Kona: Luxury Ocean View peaceful Home with Pool, Spa & Outdoor Shower
Welcome to Oasis Kona, a beautifully curated ocean-view home for your perfect Hawaiian vacation. Relax by the pool, enjoy the spa & heated outdoor shower, and take in unforgettable sunsets. With an open floor plan, lush gardens, and a private setting, you’ll feel at...
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...
NEWLY Updated 4BR OceanView House- Pool, AC & Deck!
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...