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.
Oceanview Luxury Estate - Multi-Suite Retreat in the Kona Uplands in Holualoa
Luxury Oceanview Estate – 2 Suites + Cottage + Additional Bedroom | Infinity Pool | Gym | High-Speed WiFiWelcome to our breathtaking ocean-view estate, designed for ultimate comfort, privacy, and relaxation. This luxurious retreat features two spacious suites, a...
Maui Kamaole J116: Ground floor one bedroom condo with many upgrades throug
Beautiful updated bedroom furniture and King bed in this Ground floor one-bedroom Condo. The kitchen opens up to the dining and living areas providing an open living space. The bedroom has a king bed and a flat-screen TV. The living room has a pull-out sofa bed. This...
Old Style beach house on Hanalei Bay;stunning mountain view, ocean breezes
The Old Style is a stand alone beach house just steps from the sand as seen above (Standard occupancy is 2*). There is lots of light, great views & a very restful feeling. Single wall redwood was the preferred building style back in the day. It is beautifully painted to...
Breathtaking Oceanfront Condo
Downstairs master bedroom has A/C, kitchenette, and a private entranceBig screen smart tvs in all three downstairs bedroomsLarge upstairs 2nd master bedroomFully stocked kitchen, including DeLonghi espresso machine, Instant Pot, Vitamix blender (for the BEST smoothies),...
Romantic, Luxury, Sensual Retreat - Couples Only
Welcome to The Palms at Wailea – Your Island Paradise Awaits! Located in the prestigious Wailea resort community, The Palms at Wailea condo complex stands out as one of Maui's most elegant destinations. Our 1-bedroom, 2-bathroom condo (Unit #1603) has been custom...
As seen on Discovery Channel's "Building off the grid" Volcano Home!
To watch the episode and see more about the home:Internet search for:Building Off the GridSeason 7 Episode 5 "Volcano Home" This 2-bedroom house in Volcano is perfect for your escape to relaxation. With 2 queen beds and 2 bathrooms with showers, guests can unwind in...
Waikiki Shore 1404: The Full Beachfront Experience w/ Incredible Ocean Views!
Waikiki Shore #1404 – 2161 Kalia Rd.Bask in cool trade wind breezes as you enjoy your morning coffee on the lanai or as you walk along beautiful Waikiki Beach! With its incredible ocean and sunset views, this 14th-floor condo (1 floor below Penthouse level) is unique...
NEWLY remodeled Modern Maui condo across the beach.n
Enjoy a stylish experience at this centrally located Maui Vista condo steps to popular Charley Young beach. Beautiful sunsets and a relaxing breeze on the lanai overlooking lush lawn and tropical plants. Beautifully renovated (2021) modern design. This 1bd 1 bath is...
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 updated unit can comfortably accommodate 4 people, offers a fully equipped kitchen, & outdoor dining area to enjoy your ocean view....
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 | 354
Kaanapali Alii 354 draws inspiration from its ocean views to help influence the color scheme of this vacation rental. Different shades of blue can be found in the living room rug, throw pillows on the oversized sectional couch, comfortable arm chair, wall art, and even...
Kaanapali Alii | 4114
Kaanapali Alii #4114 is a stunning two-bedroom ocean-view vacation rental that offers a luxurious retreat on Maui's renowned Kaanapali Beach. Spanning 1,843 square feet, this elegantly designed condominium features an open floor plan that seamlessly blends indoor and...
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
Imagine every comfort, every convenience, endless thoughtful touches, all in a breathtakingly scenic location. No need to imagine; you’ve found it at Sunglide Vacations Suite, where guest comfort is top priority. You’ll delight in access to the pool and hot tub, and...
New! Bright, Airy 2BR Split-Level Condo w/Spacious Layout & Stunning Ocean Views
Perfect Ocean View Retreat!Experience the magic of Hawai‘i in our well-appointed 3-bedroom, 2-bathroom condo, perfectly situated in the highly sought-after 200 building of Makanui in Poipu. This split-level paradise offers a harmonious blend of comfort and island...
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...
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...
A Plush Two-level Condo with Ocean and Golf Course Views From its Lanais
DescriptionKanaloa at Kona is in Keauhou on the water between Heeia Bay and the Keauhou Kona Golf Course. This resort boasts three swimming pools, including one that is absolutely oceanfront. There are also three hot tubs, two tennis courts, and a game room. Enjoy...
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...
Beachfront Tropical Dream House!! TVNC#4299
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)
One Rate, You Choose the Length of Stay!All rates quoted will be based on a 30 day period. Our monthly rentals will be made available to you for your use and occupancy for a period of thirty (30) days. You are not required to stay for a full 30 day period. Just stay for...
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...
Wailea Ekahi Village | 30D
Nestled in the prestigious Wailea Ekahi Village, condo 30D is an exquisitely decorated island-inspired vacation rental that offers a perfect blend of luxury and comfort with breathtaking ocean views. The lanai provides an idyllic setting for outdoor dining or morning...
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 located, along a championship golf course, is an 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 beach. This...
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...