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.
Bright & Airy 3 Bedroom Condo in Princeville
This bright and airy 3 bedroom condo overlooks the Princeville golf course along with a partial ocean view.The Kaiulani of Princeville townhomes have a single family feel combined with amenities perfect for anyone looking for a tranquil setting with a fully equipped...
Gorgeous 5 br for 12 in Kapaa - Beachfront!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!The fabulous 5 bedroom, 4 bath oceanfront for 13, is made up of a 3 bedroom and 2 bedroom oceanfront townhome, just steps apart! Fabulous beachfront pool and sundeck onsite! Beautiful...
Beachfront Paradise
Never before or again will you be directly on the beach like this in America!Relax in paradise in this Hawaiiana 1-bedroom perfect place to call your own.Live like a local, experience your paradise that you deserve.Wake up to a completely emptyNever before or again will...
Luxurious 2-bedroom/2-bathroom oceanfront condo with pool, jacuzzi and parking
Escape to this oceanfront condo on Oahu’s North Shore. This spacious end-unit features 2 bedrooms, 2 bathrooms, and comfortably sleeps 4+ with 3 beds. Enjoy breathtaking ocean views from large bay windows or relax with the soothing sound of waves. The condo includes...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanfront Gem, Over 3400 combined Sq. Ft. w/ Built-in Viking B.B.Q.
This 5-bedroom gem combines one of our very finest 3BR oceanfront "Ali'i" residences with a spacious partial ocean view 2BR suite located directly next door and is perfectly suited to larger groups or families.The generous 3400+ sq ft of the combined interior living...
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just a bike ride away from the world famous Kailua and Lanikai Beaches. With stunning views of the Ko'olau Mountains and the...
Kapalua Golf Villas Gold Fairway View 2 Bedroom
Golf Villas Gold Fairway View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and bathroom- Guest bedroom with 2...
Kaanapali Alii | 124
Kaanapali Alii 124 is an exquisite two-bedroom ocean-view rental that is perfect for families or groups seeking a luxurious getaway in Maui. This spacious residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, creating a...
Tranquil Ocean View Condo!
A beautiful place in a great location! World-famous Queens and Waikiki Beach is just a 1-minute walk from our building. Dozens of restaurants, shops, and activities are within walking distance. Food options range from food trucks to fine dining. The world-class shopping...
New Listing! Save up to 25% Instantly on stays thru 5/31/25! 2B/2B, AC, Pool
Experience tranquil island living at Kaanapali Plantation 12, nestled on 10 acres of lush tropical gardens. This serene and spacious retreat is just minutes from the renowned Kaanapali Beach. This charming 2-bedroom, 2-bath condo is a haven for golf enthusiasts,...
Charming 2-bedroom apartment on beautiful farm in Honaunau with WiFi
Honaunau Farm Wellness Retreat is a 7-acre organic, regenerative farm with sweeping views of Kealakekua Bay & lush tropical surroundings.The Ohana house has a full kitchen, living room, & covered patio with access to our retreat area with infrared sauna, outdoor shower,...
2 One-Bedroom Suites w/ Lanai – Close to Dining, Shops & Cultural Sites
Make this comfortable and convenient property your next Waikiki adventure! Relax by the pool, enjoy dinner with family at one of three on-site restaurants, or grab a pastry and morning coffee at the coffeehouse. And best yet, the sun, sand, and surf of Waikiki Beach are...
Ko Olina Kai 1083C: Contemporary 3BR, Private Lanai, Walk to Beach & Dining
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.Welcome to Ko Olina Kai 1083C by Gather, a...
Charming 4-bedroom cottage with WiFi and AC in serene Laie
Consider this cottage your home away from home while you visit Laie. This delightful property boasts 4 bedrooms including a king bed, 2 bunk beds, a queen bed, and a futon. With 4 bathrooms equipped with showers, your group will have plenty of space to freshen up. The...
Cozy studio in Ka Eo Kai, Kauai, HI
About this spaceOverlooking Anini Bay, this cozy studio suite is the perfect place to be while on the island of Kauai. Lots of amenities to enjoy. The resort offers easy access to top Kauai shopping, dining, entertainment, state parks, national wildlife refuges,...
Maui Resort Rentals: Honua Kai - 5 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought after two-bedroom "penthouse" suites with three neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
Oceanfront Kona By the Sea 2-Bedroom Retreat with Central A/C
45-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside...
New Listing Specials! Walk to Beach. Sleeps 6. Fantastic Resort Amenities.
Centrally located in Kihei and a three minute walk to Kamaole Beach, where you'll have access to some of the area's best snorkeling, whale watching, and sunsets. Short drive to coveted Wailea beach!★ Ocean View★ Private bedroom and bathroom★ Two full bathrooms★...
Relaxing Kalakauan 1-Bedroom | Private Lanai
This family-friendly vacation home is tucked away at the beginning of the Waikiki strip and features secured entry. This 1-bedroom, 1-bathroom offers easy access to the Waikiki Strip, Hilton Hawaiian Village, Fort DeRussy Beach Park, world-famous Waikiki Beach, Hawaii...
4 Units Perfect for Groups! Outdoor Pool, Close to the Beach!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Lagoon Tower! Family Friendly Resort! Beautiful Hilton Condo On Waikiki Beach!
Set along the breezy coastline of Honolulu, and with all the comforts of home. You will have access to four swimming pools, one with multiple waterslides, a saltwater recreation lagoon, daily planned family activities, Waikiki Beach access, water sports, spa...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Hale Lu'u Kini Ea B-310 Stunning Ocean Front Villa
Hale Lu'u Kini Ea - Your Perfect Hawaiian RetreatWelcome to Hale Lu'u Kini Ea, a spacious 2-bedroom, 2-bathroom villa located in the tranquil Beach Villas at Ko Olina. This villa offers breathtaking ocean views from every bedroom, allowing you to wake up to the serene...
Escape to Paradise! Townhome in Coconut Plantation, just minutes from lagoons!
Welcome to the wonderful resort area of Ko Olina! Located within the gated community of Coconut Plantation, this gorgeous townhome offers guests the perfect blend of comfort and convenience, the ideal island getaway. Features of the townhome include: Prime Location:...
AVAILABLE NOW! The WATERMARK! 1551 Ala Wai Honolulu HI 96815 Unit 704
Available starting August 2023! Stunning Luxury 2BD/2BA/2PK with Ocean Views! The resort style luxury building, "The Watermark", is within the heart of Waikiki! Live amongst the clouds with First class amenities including recreation area with heated pool, relaxing...
Maui Resort Rentals: Honua Kai Hokulani 1029 - 2BR Deluxe Oceanview Grand Penthouse, BBQ on Balcony + Jaw-Dropping Ocean Views!
We are proud to present this jaw-dropping 10th-floor deluxe oceanview grand penthouse at the Honua Kai Resort—newly launched on 3/4/25 to start taking bookings beginning May 7, 2025!Unquestionably one of the finest residences on offer at Honua Kai, this stunning...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
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.Discover the epitome of island elegance at Ko...
1 BR Suite City View, w/ AC, WiFi and Kitchen - Bamboo Waikīkī Hotel #504
Castle Bamboo Waikīkī Hotel #504 - The living area is furnished with a and a desk/workspace for all those business travelers. Enjoy watching the Flat screen TV while sitting on the new couch, which doubles as a fold-out sofa bed to accommodate additional travelers....
Maui Resort Rentals: Honua Kai Hokulani 814 - Top Floor 1BR w/ Partial Ocean & Mountain Views!
This beautifully appointed top floor "penthouse" suite boasts one of the best one-bedroom locations available at Honua Kai. Enjoy generous partial ocean views from the balcony and primary bedroom in addition to great views of the verdant West Maui Mountains. This suite...
Charming 2-bedroom villa with WiFi, AC in wonderful Kapolei
Located in Kapolei, enjoy what this lovely 2-bedroom villa has to offer. With 2 king beds, AC, WiFi, and a fitness room, guests can relax and unwind in style. The charming decor and modern amenities make this vacation rental a terrific choice for your getaway. Fall in...
"BEAUTIFUL LUXURY CONDO WITH GORGEOUS VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA"
"MODERN LUXURY CONDO WITH BEAUTIFUL VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA""WELCOME TO SKY ALA MOANA" Luxury condominium built in 2023 conveniently located in Ala Moana. Enjoy beautiful views of city, mountain and sparking ocean. 1br/1ba /1assigned parking with Full...
Marriott Maui Ocean Club | Three 3BR/3BA Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ocean-MT Views From the Luxury Sky Ala Moana Condo with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to the luxurious building scene in Honolulu. Consisting of two...
Manele Bay, Lanai Hawaii Ocean Facing Home
Spacious home on the island of Lanai. Footsteps from Four Seasons at Manele Bay Hotel and Hulopoe Beach. All the comforts of home in an island paradise. Two bedrooms, each with king-sized beds, and two and one half baths, including an outdoor shower. Ocean view and...
Pet Friendly Private Room In Shared Guesthouse
Private Room Rental in Shared GuestHouseVery Walkable Location. We're Located Within Walking Distance To Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking Trail, Safeway Grocery Store, Restaurants, Starbucks, Jamba Juice, Honolulu Zoo, Close to...
Steps Away from the Beach! 3 Premium Units, Private Lanai, Onsite Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
2 Bedroom Mountain Garden at Marriott's Maui Ocean Club - Lahaina & Napili Tower
Spread out with the whole family in this spacious two-bedroom suite. This is as classic as a Maui oceanfront resorts get. Tropical greenery, koi ponds, palm trees, and Pina Coladas around every corner. Really, this place is situated perfectly on Ka’anapali Beach,...
Oceanfront balcony, 40 ft to ocean, 2 bed, 2 bath, remodeled! 3/8-3/15/2025!
This is Hono Koa, a timeshare resort located in Honokowai, 1 mile to Ka'anapali Beach resorts, and 3 miles to Kapalua. It's an easy 1-mile walk to the Times Market grocery store. We own only the KOA oceanfront units. They are bigger and nicer than the other units. The...
Kaanapali Alii | 341
Kaanapali Alii 341 is a luxurious oceanfront vacation rental located about a 35 minute drive from Kahului airport along Maui's beautiful western shoreline. This spacious condo offers breathtaking views of the Pacific Ocean, the islands of Lanai and Molokai, and the...
Maui Resort Rentals: Westin Kaanapali Ocean Resort Studio Oceanview Villa
Luxury Oceanview Studio Villa at The Westin Ka'anapali Ocean Resort Villas. This oceanview luxury studio villa features views of the Pacific Ocean and sleeps up to 4 with one king sized bed and one queen sized convertible sofa sleeper. The villa is equipped with a...
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Ocean-View Lanai (800 Sq Ft) | 4 Mi to Ho'okipa Beach Park | Newly Renovated Kitchen Experience the serenity and adventure of island living when you stay at this stylish Haiku vacation rental! Located just 4 miles from the coast, this 3-bedroom, 2-bath home makes it...
Charming 1-bedroom condo at Luana Kai in Kihei with WiFi B204
B204 is a charming one-bedroom, one-bathroom unit, situated on the 2nd floor (NO elevators so you are walking up stairs) is a wonderful tropical oasis for your dream vacation. Step into a spacious living area that comfortably accommodates up to four guests, making...
The Marbled Suite - Waikiki - Ala Moana - McCullynn
With all the convenience of Waikiki, but with free parking for your rental car. Located between Waikiki, Ala Moana, and the highway (without highway noise). For those looking to also explore outside of the tourist bubble called Waikiki, this location is golden. Minutes...
2-bedroom condo steps to the beach!🏝️
Located in Waialua, enjoy what this 2-bedroom condo has to offer. This delightful property features 1 queen bed, (second queen on request). Guests can relax in the cozy living space or take a 1 minute walk to the beach with family friendly amenities like a jungle gym,...
Kapalua Bay Villa 18B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- Split level villa with no stairs between parking and front door- Tile floors throughout- Updated kitchen with granite counters includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware, tableware and unique chef’s...
Tranquil Marina Front Pool House Resort
Marina Front Property in peaceful Cal-De-Sac with large tranquil salt water pool and marina access.Spacious outdoor patio lounge with BBQ grill and prep station and patio furniture and large TV.Parking for two cars! Close to Hanauma Bay, Kona Brewery, Costco, Koko Head,...
Kaanapali Maui Eldorado Garden View 2 Bedroom
Garden View 2 Bedroom 2 Bath- Full kitchen includes refrigerator, stove/oven, microwave, dishwasher, cookware, tableware- Master bedroom with 1 king bed- Guest bedroom with 2 double beds- Sofa bed in living area- 1700 square feet / 158 square meters- Bathroom with...
Dreamy Beachfront Home - Car & Parking Available
*** Aloha! Welcome to our happy place! ***** Newly Remodeled Coastal Retreat, with Floor-to-Ceiling Ocean View **Welcome to our beach house, where every detail has been thoughtfully designed by a professional interior designer to create a serene, luxurious...
Hapuna Beach Residence B13 at Mauna Kea Resort
This impeccable, oceanfront, newly-constructed, ground level island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a true chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
New Listing, Vistas Waikoloa B203 2/2. Ocean Views
Tropical Retreat at Vistas Waikoloa B203- AC, WIFI and ocean viewsAloha and welcome to your serene escape on the Big Island! Nestled in the heart of Waikoloa Beach Resort, Vistas Waikoloa B203 is a spacious 2-bedroom, 2-bath condo offering comfort, privacy, and ocean...