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.
Recently Remodeled, Modern, Nice Condo in a Great Location
One bedroom, one bath condo with a great walk in shower. Nice kitchen to save money and prepare your meals. Large tv, fast wireless internet, full size in unit washer and dryer, and a free parking stall. Nice lanai to enjoy your morning coffee, and ac in the unit....
Gorgeous Kapalua Home with Views
This gorgeous Maui home is a two story end unit with expansive ocean views from lanais on each level! Located in the renowned Kapalua resort area on the northern coast of Maui, you are not only close to the beach (less than a 5 minute walk, to be exact), but within...
Aloha Charm on Maui's North Shore - Right by Mama's Beach.
2 rows off the sandy beach in a quiet north shore neighborhood. This property is perfect for family and friends or a couple. 'A breezy and charming home, Maui Winds invites rest and relaxation and offers exciting activities for top-notch athletes ready to windsurf,...
Gorgeous Gated Retreat Near Ocean w Pool & Deck!
Enjoy a blissful vacation at the Heavenly Hawaiian Paradise Beach House. This 3BR/2BA retreat is perfect for groups up to 10, offering welcoming spaces both indoor and outdoor to dine and relax in the beautiful Hawaiian weather. Spacious outdoor deck with swimming pool,...
STUNNING FAIRWAY VIEWS, HOME "E"-CLEAN-NEW-GATED, NEAR JBPHH, CAGE # AVAILABLE.
Welcome to Hillside Perfection overlooking the fairways at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers or visiting construction crews...
Luxury 1BD in ONE ALA MOANA with Beautiful View and Room with Free Parking!!
One of the most luxury condominium in Hawaii. You can experience the best vacation ever in One Ala Moana!!The minute you go inside, you will be astonished the amount of light coming through huge ceiling to floor windows overviewing the city and the mountains. The fully...
Tropical Acreage + Fruit Trees + Beach ~5m drive!
Welcome to "Pua Pono House," on Oahu's captivating North Shore, where country living meets relaxation, away from the hustle and bustle of Honolulu and touristy hotels. Nestled on a lush one-acre estate, our retreat offers a serene and secluded oasis. Centrally located...
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean Views
This property is hotel zoned, and not being affected by the recent proposed legislation.Luxury at its finest! Ho'olei Villa 17-1! Mesmerizing ocean views and bright open floor plan welcome you. Enjoy the beautiful Maui sunsets on your expansive private lanai.One of the...
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View and Peek Oceanview!SLEEPS UP TO 7! This Luxury Condo Offers Guests a Gorgeous View of Sleeping Giant Mountain and peek ocean view from the lanai. This Condo is a 2 Bedroom, 3 Bathroom Condo at...
Hale Malulani - Luxury Oceanfront Puako Villa with Pool, Hot Tub & Pickleball!
Immerse yourself in the unparalleled luxury and breathtaking beauty of Hale Malulani, an exquisite oasis nestled in the serene shores of Puako, now gracing the rental market once again, following a meticulous and extensive renovation. This exquisite property proudly...
Penthouse Waipouli Beach Resort E404 - Beautiful Ocean & Pool View
Penthouse - Ocean & Pool View 1 bedroom "Jewel" - ACExperience your vacation in this Beautiful Ocean and Pool View, a 1 bedroom, 2 bath condo "Jewel" in this Oceanfront Resort & Spa. From the moment you walk into the living room and master bedroom you will know you made...
Golf Course Views | AC & Shared Pool |vrKCV
vrKCV - Holua Kai 6, Professionally Managed by Kona Coast VacationsHolua Kai 6: Luxury Home with Stunning Golf Course Views and Modern Comforts in a Gated CommunityWelcome to Holua Kai 6, your home away from home! Nestled within the private, gated community of Holua Kai...
nKaanapali, Ocean Front Condo, Free parking and NO Resort Fee’s, Cabana Access.
EXTRA AMENITY If you are arriving early or departing late, we have a Cabana for your convenience with a pool, spa, full kitchen, refrigerator, rest rooms, TV, WiFi, Bar B Que, books and games, for your use. Come for our winter season and see the Whales from our lanai....
***SPRING SPECIAL*** Charming Home, Just Minutes from Town and the Beach with Ocean View.
Kona Ocean View Vacation RentalWelcome to your Big Island retreat—a spacious two-story vacation home in a peaceful neighborhood just minutes from downtown Kona and some of the island’s best beaches.The open kitchen flows into inviting living spaces, while an outdoor...
Poipu Tropical Retreat with A/C & Pool/Gym Access
Discover beautiful Kauai from this spacious 1 bedroom vacation home (built in 2018) in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai,...
Kuhio Shores 113 - Exquisite Ground Floor Unit Right Next To The Ocean
Located on the sunny South Shore at Poipu Beach, just 10 steps from the water's edge, this 1 bedroom condo offers the best oceanfront vacation rental that Kauai has to offer. At Kuhio Shores #113 nothing can beat the location and views. Perfect paint, perfect...
Beachy Kona Getaway. Located within walking distance to the heart of Kona Town.
Welcome to our dreamy Kona getaway! This newly refurbished, luxury beachy retreat is designed for relaxation and convenience in the heart of Kailua Kona. Walking distance from Kona's best restaurants and bars, it provides easy access to Ali'i Drive and all it offers,...
25% OFF for MAY 2025-Direct Ocean Views From Every Window - 3bd/3bth Honua Kai
THE MAUI LUXURY RESORT LIKE NO OTHERPicture the perfect Hawaii vacation: Of time spent with family and friends, of cares washed away by sand and sea—and the discovery that life can still hold magic, especially in a place called Maui.Now picture the perfect setting:...
NEW - Luxury 4BR, 3.5 BT, Hot Tub, Cold Plunge, Steps from Queens Bath
Discover the perfect balance of comfort, adventure, and relaxation at Honu House Kauai. Just renovated and brand new for guests to enjoy. Steps from the famous Queens Bath or walking/biking to Hideaways Beach, The One Hotel, and Makai Golf Club. Private hot tub and...
Papakea H201 - Vacation West Maui
Escape to Paradise in Maui's Premiere Oceanfront ResortNestled in the heart of Papakea Resort, unit H201 beckons you with breathtaking ocean and garden vistas. This corner unit on the second floor offers more than just a place to stay – it's your portal to the magic...
Country Club Villas#326 Top Fl Corner, Incredible Oceanview,Spacious Lanai,AC
Country Club Villas, Unit#326 is a phenomenal new addition to the Vacation Rental Market that Knutson & Associates Property Management is proud to represent. This top floor corner unit is completely remodeled, with soaring ceilings & lots of extra windows for natural...
Ko Olina Kai 1097C: 3BR Hawaii Haven with Golf, Lagoons, and Spa Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Step into the world of serene luxury at Ko...
Mauna Lani Treasure - Newly Decorated 3 Bed/2.5 Bath Townhome with Beach Club
Kick back and relax in Paradise in this 3 Bed/2.5 Bath Townhome decorated in Hawaiian style. Enjoy this spacious home with a custom kitchen, outdoor lanai with grilling area, and open concept living area. Sip a tropical drink off the lanai enjoying spectacular views of...
Hale Kai - Brand New Kukui'ula Luxury Home with Pool & Spa
Nestled in the exclusive Kukui'ula neighborhood in Poipu, this stunning, brand new luxury home offers the perfect blend of comfort, elegance, and island charm. With 4 bedrooms and 4.5 bathrooms, this meticulously designed residence comfortably accommodates up to 10...
Experience the perfect blend of privacy, tranquility, and luxury at Na Hale O Keauhou
Welcome to Kai Nani Hale – Luxury Living in ParadiseDiscover Na Hale O Keauhou, a prestigious gated community nestled in the heart of the Keauhou Resort area. This meticulously maintained 13.36-acre complex features 14 pods, each comprising six two-story townhouses,...
Moloa'a Bay Villa - Impressive Home and Guest Cottage
Moloaa Bay Villa, on the northeast shore of Kauai, is steps away from a secluded white sand beach! Welcome to Moloa'a Bay on the northeast shore of Kaua'i. This is a large, secluded, pristine white sand beach that lends itself to coastal hiking, snorkeling, body...
Kaanapali Alii | 352
Welcome to Kaanapali Alii 352, your perfect luxury vacation rental in the heart of Maui. This stunning one-bedroom plus den corner unit offers a blend of modern elegance and tropical charm, making it an ideal short-term rental for families seeking a serene and memorable...
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
"In order to comply with Oahu's 90 day minimum short term rental laws, we may not advertise to rent for a period shorter than 90 days."Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully furnished with a modern meets the...
Villa Sea Renity Remodeled Family Friendly Tennis
Experience the relaxing setting of this 1BR 1.5Bath condo in the lavish gated community just a stone's throw away from beaches, shops, restaurants, and attractions of Hawaii's Big Island. Take in the area's scenic beauty and diverse selection of water activities. After...
Luxury Mahana Oceanfront Condo -1bd/2ba - Premium 10th Floor- Fully Upgraded
Welcome to Mahana 1015, a breathtaking oceanfront condo located on one of the top floors of the exclusive Aston Mahana at Ka’anapali Resort. Offering two full bathrooms and spacious accommodations, this one-bedroom suite is the perfect place to indulge in Maui’s...
Beautiful Oceanview Condo with Spectacular Sunsets! - Recently Renovated
Located on five miles of sandy beach on Maui’s southwest shore, the lovely Sugar Beach Resort will capture your heart. Take a leisurely stroll down the sparkling white-sands of Maalaea Bay’s Sugar Beach, one of Maui’s favorite places to swim, snorkel, kite-board,...
Cozy studio, split AC, kitchenette, steps to beach in best South Kihei location!
Aloha and welcome to the Tranquil Turtle Retreat at Maui Banyan Resort! Our recently updated studio is located right in the heart of South Kihei close to world-class beaches, shopping and amazing restaurants. Enjoy Maui at its finest!The Tranquil Turtle first floor...
Spectacular 3 Bedroom Oceanfront Marriott Maui Ocean Club
Welcome to Marriott's luxurious 5-star resort and its spectacular Lahaina and Napili Tower villas! Your sophisticated, bright, spacious oceanfront 3 bedroom/3 bath villa, with breathtaking panoramic Ka'anapali Beach and expansive Pacific Ocean views...as well as every...
Loft Style Completely Remodeled Condo
This stunning condo is located in the oceanfront building of the Kona Bali Kai, although not an oceanfront condo. There isn't an ocean view, but your proximity to the ocean is VERY close!! Just a walk through the under building parking garage, and you're there!The unit...
Kauai Exclusive - Pili Mai 7E - Three Bedroom Suite - AC, Pool & Fitness Center
Pili Mai 7E is a three-bedroom, two-level suite with plantation-style architecture. Newly furnished and decked with bamboo floors, Koa cabinets, a gourmet kitchen and central A/C, this villa is a fresh find. Revel in all the bells and whistles of a new tropical vacation...
Hawaiian-style Oceanfront Villa - Outrageous Views, Beach Access, Ahh!
Enjoy Kauai's simple pleasures and grand landscapes right from home! From the moment you arrive, you immediately sense the Aloha spirit and the other-worldliness of Kauai's North Shore. Hanalei Bay Villas' surroundings are stunning and beyond beautiful; the unique...
Hoku Hideaway - AC, Ocean Views
*30 day listing. Please Inquire.Hoku Hideaway is a 3-bedroom, 2-bath home that offers the perfect blend of comfort and island charm. Located just across the street from the ocean, it provides easy access to stunning beach views and relaxing coastal breezes. The home...
Beautiful Mauna Lani Villages Townhouse
The Villages at Mauna Lani is a private gated community that offers the ultimate in comfort and convenience. This is our family’s dream vacation home and we think you will agree. This is a fantastic home for a family getaway. This is a two story townhouse with over...
Ground Floor & ac - KBV11G2 - Sullivan Properties
This unit proudly features:• 1 BD / 1 BA (king + queen sofa sleeper)• Air-conditioning (central)• Ocean Views from unit• Fully Equipped Kitchen• Washer/Dryer• WIFI in the condo• Spacious with over 975 sq.ft• Stairs from parking lot• Sandy beaches with...
Four Seasons Resort Hualalai at 4th Fairway, Ocean View with 2 Golf Carts
Beautifully maintained, this villa offers a welcomed amount of privacy from both the upper and lower levels without compromising stunning panoramic view of the ocean and the 4th fairway of the Jack Nicklaus signature Hualalai Golf Course. The retreat on the lower level...
Discount ending soon! Ocean View - 1 Bedroom Villa - Marriott's Ko’Olina -
Unit sleeps 4 (website error says sleeps 6). Discover paradise in our stunning 1 Bedroom Villa at Marriott's Ko Olina Beach Club! Enjoy breathtaking ocean views from your private balcony while relishing the luxurious amenities and exclusive activities we offer.Our...
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
PROPERTY PROJECT:The upper pool will be closed from November 11th through November 21st 2025 to re-coat the upper pool deck. Beautiful updated bedroom furniture and King bed in this Ground floor one-bedroom Condo. The kitchen opens up to the dining and living areas...
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...
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...
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!
Volcano Rainforest Retreat — As Seen on “Building Off the Grid”!To see our home featured on TV:Search online for Building Off the Grid — Season 7, Episode 5: “Volcano Home”Welcome to Volcano Home, a handcrafted 2-bedroom, 2-bath rainforest retreat on the...
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...