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.
Ko Olina Beach Villas O1006: Luxe Penthouse w/Pool, Golf, & Ocean Views
Welcome to Ko Olina Beach Villas O1006 by Gather, a stunning two-bedroom, two-bathroom tenth-floor penthouse with space for up to six guests in the exclusive Ocean Tower of Ko Olina Resort. This exquisite villa offers breathtaking ocean views, complemented by serene...
1br/1ba Condo Steps From The Pavilion pool, Mokapu Beach with beautiful views.
This is a 1 bedroom, 1 bath upper level condo for a maximum of two people. It is well furnished and equipped, is very comfortable and located in well maintained lush Ekahi Village. The unit is air conditioned with a Lanai off of the living room and the Bedroom, there is...
Amazing beach views from Lae Nani condo with new updates!
Enjoy a beautiful ocean view from our condo overlooking the beach. At Lae Nani you can relax at the pool while surrounded by lush gardens just steps from the beach. Located on Kauai's central coast, 10-15 minutes from the airport, Lae Nani is secure with gated access...
87-1 Escape to Paradise at Puamana's Hale Nalu
Welcome to Hale Nalu, a beautifully updated townhome in the tranquil Puamana community just south of Lahaina. This 30-acre private paradise offers a peaceful retreat away from high-rise hotels and crowded tourist areas, yet remains close to world-class beaches and golf,...
Beautiful Spacious Oceanfront Condo on Wailua Bay
Welcome to 'Wailua Hale Lani'; our beautiful, Kauai, one bedroom, one bath condominium at Wailua Bayview. The condominium is on the second floor (#201) of a three-story, 45 unit complex. Continually updated and meticulously maintained, the unit boasts island-themed...
Ground floor, ocean view, and steps to all the amenities.
Welcome to Hale Ono Loa 114. This 1 bed/ 1 bathroom ground floor, ocean view gem has everything needed to make amazing Maui memories. This unit can comfortably accommodate 4 people, offers a fully equipped kitchen, & outdoor dining area to enjoy your ocean view. Admire...
Hale Hapu’u. A unique Hawaiian experience.
E Komo Mai (welcome) to Hale Hapu’u! Our little Hawaiian hut is perfect for couples seeking an authentic Big Island experience. The Hale is adorned with hand carved art from local artists, an outdoor bath set in the midst of a tropical garden of ferns, palms &...
Kaanapali Alii | 4114
Welcome to Kaanapali Alii 4114, your luxury vacation rental on Maui's renowned Kaanapali Beach. This stunning two-bedroom ocean-view condo offers a serene retreat with breathtaking views of the Pacific Ocean. Spanning 1,843 square feet, the property features an open...
Pahoa House with Lanai, Walk to Ocean!
Escape to the beauty of Pāhoa and experience the perfect balance of luxury and location at this 3-bedroom, 2-bath vacation rental. Situated 5 miles from Puna Kai Shopping Center, this home is a dream come true for adventurers and relaxation seekers. Immerse yourself in...
A Perfect Kapalua Beach and Golf Getaway - Specials!!!
Come enjoy our spacious 1 bedroom, 2 bathroom condo in one of the most beautiful spots in all of Maui. Located directly on the 4th fairway of the Kapalua Bay Course can be both entertaining and comical as you watch the golfers pass by. A picturesque ocean view with the...
"Sea World" at Your Feet + Casual Elegance + Absolute Privacy = Whales Play
Wonderful experiences await your arrival at Whales Play, a secluded and tranquil retreat. Take in the panoramic views while lounging on the upper lanai, watching whales and dolphins at play. Savor a lingering sunset and then be dazzled by the starriest night sky from...
Relax in the Kapalua Golf Villas - Listing newly back on the market - Specials!
Relax in paradise! Top floor condo with a one level floor plan. All new furnishings, carpet and paint. Lovely lanai to watch the golfers go by and enjoy the views and smells of the island of Maui. There are 4 pools in the Kapalua Golf Villas, with a heated pool right...
Stunning oceanfront cottage
This beautifully restored one-of-a-kind oceanfront home has all the charm of yesteryear with the added conveniences and sustainability of today. Meticulously appointed and private, the views and location are spectacular. The Guardian newspaper has listed Kona Moana Hale...
Pristine Hawaii Retreat with Ocean, Golf & Palm Tree Views. Top corner unit!
Feel at home in this gorgeous corner, top floor villa in the Hali'i Kai oceanfront development in upscale Waikoloa Beach Resort. This fabulous 2 bedroom villa is perfect for 4 adults (plus one child with owner approval).Enjoy your morning coffee on the lanai, taking in...
Cozy Condo in Kihei - Steps from Kamaole 3 beach for a family or couples holiday
Embark on a journey into serenity within the confines of a remodeled 1-bed, 2-bath condo, spanning over 800 sq. ft. Under the dedicated stewardship of an attentive owner, this unit serves as a promise of a peaceful escape amidst the enchanting landscapes of South...
Charming Condo with AC/Saltwater Pool/HotTub, Close to the Best Beaches and Golf
Step into the kitchen and hallway area of Sunglide Vacations Suite via convenient keyless entry – and go claim your bedroom from your choice of two bedrooms!Discover the second-floor Master Suite with its California king bed flanked by bedside tables with lamps. There...
Maui Resort Rentals: Kaanapali Ali'i 312 - Luxurious 2BR Ground Floor w/ Partial Ocean Views & Large Lawn Area, Steps to Pools, Beach, BBQs!
Luxuriously remodeled, this 2br gem provides an expansive 1500 sq ft of interior living area and features a convenient ground floor location. Enjoy peek-a-boo ocean views from the expansive ground floor lanai and the large adjacent lawn area. Due to the convenient...
Luxurious 2-Bedroom Retreat in the Heart of Waikiki.
Waikiki Landmark Unit 2901. Escape to paradise in this spacious and luxurious 2-bedroom, 2.5-bathroom condo at Waikiki Landmark, Unit 2901. Located in the heart of Waikiki, this expansive unit offers everything you need for an unforgettable Hawaiian vacation. Fully...
Oceanfront remodeled 1-bedroom condo
Maui Kai 1001 is a 1-bedroom, 1-bathroom corner condo on the 10th floor with central air conditioning that can accommodate up to 4 guests. Island charm and classical Maui decor adorn this west-facing condo making it a wonderful location. Unit 1001 boasts an enclosed...
PRIVATE OCEAN VIEW MAIN HOUSE + EXTRA SUITE, 5 MIN WALK TO POIPU BEACH, A/C
Enjoy A/C throughout the entire house. Our newly remodeled 1920's Hawaiian owned and built by my great grandparents, was originally the first house on the hill above Poipu Beach. Entering Poipu Hale Ohana, you will be stunned with views that overlook Poipu Beach, the...
Ocean View Villa on 6th floor w/Semi-Private Elevator
Our condo is both beautiful and luxurious. Take advantage of the view by opening the lanai doors that disappear into the walls for the ultimate in indoor/outdoor living. It has a full frontal ocean view from the Lanai, the living room, kitchen, and dining room. The...
Waiohai Beach Club - Island View
Experience the unparalleled magic of Hawaii at Marriott's Waiohai Beach Club, a premium vacation ownership resort on Kauai. Located by the ocean on Poipu Beach, we offer spacious villa rentals and an array of resort amenities for your visit to the Garden Isle. Find your...
Island Style Elegance on a Beach Access
Island style elegance with beach access.Immerse yourself in the island inspired luxury of Portlock Paradise. Sitting on large lush ocean access property, Portlock Paradise offers four bedrooms, 3 with ensuite bathrooms, an indoor and outdoor dining areas, elegant...
Boho Island Paradise - Remodeled 2BR/2BA
Welcome to your tropical retreat in the heart of Waikoloa, Hawaii! Our recently renovated 2-bedroom, 2-bathroom condo blends boho-chic style with modern conveniences, providing the perfect backdrop for your dream vacation. Whether you’re in search of relaxation or...
Naue Beach Tropical Dream House on Kauai's North Shore
Vacation 'Hawaiian Style' with Beautiful Naue Beach right outside your door. This home has a premium ocean/beachfront location right at Naue Beach. You are surrounded by North Shore beauty. No parking worries for you. It is perfect for watching whales (in season),...
Lani Paradise - Oceanfront Retreat with Private Pool
Discover paradise with a private pool, surrounded by natural oceanfront scenery. Revel in the charm of this tastefully decorated 4-bedroom, two-story Villa and romantic 2-bedroom Cottage overlooking Maui's North Shore.This exclusive property offers private waterfront...
Dream Vacation at Ko Olina Hillside Villa (1498-8)
Escape to paradise and immerse yourself in our amazing 3-bedroom, 2.5-bath vacation rental nestled within the prestigious Hillside Villas of the Ko Olina Resort. This beautifully furnished retreat offers a perfect blend of comfort, and convenience, ensuring an...
Family friendly condo, bright and beachy, walk to the beach! AC, pool, hot tub!
Maui needs your help. I live here on Maui and have been volunteering in the medical tents and with organizations delivering supplies to those in need. And the ongoing effort will need to continue in Lahaina for years to come. But Maui is open for tourism and thousands...
Kksr#1203: Direct Oceanfront, 2nd Floor, Remodeled, Stunning Location
Keauhou Kona Surf & Racquet Club#1-203 DIRECT OCEANFRONT, INCREDIBLE 2ND FLOOR FULLY REMODELED UNIT!Welcome to unit #1-203 at the Keauhou Kona Surf & Racquet Club! Knutson & Associates Property Management is so proud to be newly representing this absolutely breathtaking...
Sugar Beach Maui! Direct Ocean Front! Best View! Best Value! Penthouse!
Sugar Beach Maui! Direct Ocean Front! Best View! Best Value!Best views! Best kitchen! Best bed in the price range! If you are looking for the best view in Maui direct ocean front with central air! This is it! Updated & upgraded gorgeous granite kitchen! The super bowl...
4 Bedroom Mountain View Condo at Pili Mai!
Pili Mai is located along the Kiahuna championship golf course and is the ideal location on the island of Kauai's south shore in Poipu Beach. This luxurious 4 bedroom 3.5 bathroom corner end unit is the perfect spot for touring the island and relaxing after a day at the...
Oceanfront with AMAZING Views and AC! 2 Bedroom, 2 Bath Corner Unit KKSRC #3104
Oceanfront condo with amazing views! Two bedrooms, each with a Cal King bed, two full bathroom ground floor corner unit with extra large lanai and AC. Well equipped kitchen with everything you could need. Located in the Keauhou Surf and Racquet Club, which has a...
Romantic, Luxury Condo with Spectacular Ocean Views
1 BR, 2 BA condo. Close to beach, golf, tennis, restaurants, and shopping.Aloha. We are excited to be the owners of this very special condo. We have been coming to Maui for over 25 years, and we love the magic that this island has had in our relationship. With...
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
Aloha! This unit will continue to be a short-term rental (as a second home for our family to visit on Maui, to employ locals, and to share it with our guests). Come experience the spirit of aloha while staying at our oceanfront coastal themed townhome, designed with a...
Coconut Plantation by AvantStay | Resort Access, 0.4mi Walk to Beach!
Please note that this home is available for 28+ night stays only.Aloha from Coconut Plantation! Immerse yourself in the island lifestyle at this stunning two-story condo, surrounded by swaying palm trees and lush tropical landscaping. With 4 bedrooms and 3 full...
Oceanfront condo with lanai, grill, & beach gear - pool, hot tub, & beach access
Pali Ke Kua 124Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Embark on the Kauai vacation of a lifetime in Pali Ke Kua unit 124, a fully-renovated and modern oceanfront condo...
SPECIAL RATE! 5/11/25 to 5/16/25 1,150 per nightnLOCATION! LOCATION! LOCATION!
Hale Halia is just steps from Poipu Beach park with unparalleled oceanfront views and is a great family vacation destination. This lovely two-story floor plan is a design that takes full advantage of the magnificent Poipu coastline and sunset views. The large spa...
Spacious Newly Remodeled 4 Bdrm Oceanfront Unit in Premium Puamana Location
Experience a relaxing Hawaiian vacation in one of Maui's most serene oceanfront settings. Despite the devastating fire in Lahaina, Puamana remains a haven of tranquility and beauty, where the spirit of "Old Hawaii" lives on. Unit 9-1 is located within Puamana, a gated,...
#1 GUEST FAVORITE for Napili & Kapalua Bays !
#1 GUEST FAVORITE! Enjoy this luxury residence with beautiful bamboo flooring, contemporary island design, dramatic floor-to-ceiling windows and easy access to heavenly Napili & Kapalua Bays. This home offers you a chance to fill it with laughter as you entertain your...
Weekly Discount! Includes Golf and Yoga Discounts - Ocean View!!
Kings Club Gold Membership Exclusively for guests of 16G included! Big Savings! This membership gives overnight guests of the unit (16G) access to golf at Hawai`i’s premier 27-hole golf experience is comprised of three nine-hole loops, Beach Nine, Lakes Nine, and...
Newly remodeled ocean view condo - Kihei Alii Kai
Unit D-205. Located across the street from the kamaole beach park. This property has all new furnishings and king size bed. Air conditioning, 65 in tv, full queen mattress wall bed as well as two twin sofa sleepers,, full kitchen with all the amenities . Owner supplies...
Moloaa Bay Cottage: 1 BD/1 BA Home with Den, Loft & A/C
Moloaa Bay Cottage is located in Moloaa just steps away from a white sand beach. The Cottage: At the south end of the property near the entrance is a detached separate 2nd story guest house consisting of 994 square feet of air-conditioned living area with 1 bedroom +...
Kaanapali Alii | 361
Welcome to Kaanapali Alii 361, your luxury vacation rental in Maui, where every detail is designed for comfort and elegance. This stunning sixth-floor condo offers breathtaking ocean views and a serene escape for up to four guests. Step inside to discover a spacious,...
Princeville Mountain View Private Home
Private home within walking/biking distance of Sea Lodge Beach, Golfing, Tennis and Princeville Center. Distant ocean views from upstairs office. Enjoy wonderful mountain and waterfall views as you sip your coffee or cocktails from the back deck. Downstairs bedrooms are...
KBM Resorts | FREE CAR | Islands at Mauna Lani | 2-Bedroom Condo with Golf Cart & Exclusive Private Beach Club Access! IML-E4
** 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...
Pau Hana Hale - Private Mini-Resort with Pool
Pau Hana Hale, Princeville Pau Hana Hale is a tranquil and secluded residence nestled at the end of a peaceful cul-de-sac on a spacious lot, surrounded by verdant valleys in your own private mini-resort. Offering sweeping views, you can relax under the shade of the...
Hale Pono- Oceanfront, private, gated, great views, AC, large property
Welcome to Hale Pono!The North Shore of Oahu’s premier luxury getaway.Please message me with any questions about available bookings.This hidden, elegant beauty sits on pristine property within the exclusive, gated community of the Sunset Beach Colony. Surround...
Maui Resort Rentals: Luana Garden Villas 5A – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3Bedroom/3Bath residence is conveniently set within Enclave One of the Luana Garden Villas. This premiere grounded offering's southern orientation offers a bright inviting setting for you and your ohana (family) and its designation within our "Grounded"...
A/C OCEAN VIEW LUXURIOUS HAWAIIAN GEM
AMAZING OCEAN VIEW, GROUND LEVEL CONDO, SLEEPS 4. #B112 Perfect for a family vacation, special occasion or that romantic getaway for two This contemporary condo offers everything you could need and more....including zoning to the crashing sounds of the ocean waves from...
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
Zone for vacation rentals and not impacted by proposed zoning changes. Fully legal and stable rental unit. Fresh out of helping the Lahaina fire victims, our unit is back on the market. Modern, fully updated spotless condo with a great view of the beach. Everything is...