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.
Ultimate Oceanfront Luxury-Private penthouse in South Maui-Perfect for families
The Penthouse Maui, our luxurious 2,824-square-foot vacation rental, sits directly above the golden sand and shimmering surf of Kamaole Beach II in the heart of sunny Kihei, Hawaii. Whether you’re celebrating with family, vacationing with friends, or simply seeking a...
Hale Kai O'Kona #7: Luxury Oceanfront End-Unit, Only 2 Min Walk to Beach w/ AC
Experience the ultimate tropical vacation by staying at this Big Island Beach House, a luxurious oceanfront property located in the western condo community of Hale Kai O'Kona. This stunning vacation home is managed by Gather, the premier property management company in...
New Listing:Tall ceilings, ocean views, and more!
Ekolu 404 is a spacious 2-bedroom, 2-bathroom second-floor condo, perfect for up to 6 guests. It features three private lanais, air-conditioning, and a washer/dryer. The master bedroom and guestroom both have king beds, while the living area offers a queen sleeper sofa....
Oceanfront "Treehouse" at Hakalau cliffs
Welcome to our Treehouse at Hakalau! The only way to stay closer to the ocean would be in a boat. Watch the cruise ships slowly pass by knowing that the passengers aboard are truly envying your accommodations. This quaint and unassuming second story home offers 180...
Beautiful beach house Tunnels Beach, Kauai
This gorgeous property is a favorite vacation spot for well-known actors, musicians, athletes, artists, doctors and entrepreneurs. We have many repeat visitors who feel that our house is their second home.Rising from the Pacific, Kauai's signature peak (called Bali Hai...
North Shore Getaway w/ Ocean Views steps to Beaches and Surf
This beautiful getaway features a secure gated driveway accessed by remote in which you will enter. Drive up left side of Garage to recessed home where you will access a set of stairs only accessed by you and your guests. This entry leads to an open floor plan Private...
Minutes from Hawai’i Volcano National Park...Peaceful, tranquil and just awesome
Awarded Most Hopspitable Host for the State of Hawai’i, Gigi’s Volcano Cottage is the perfect place to stay if you want a quiet, cozy and peaceful retreat. Relax to the sound of local birds, wind in the trees, rain showers on the roof. Sit outside in the morning and...
NEW LISTING!! 2 bedroom/1bath Hale Honu with Jungle Views!
Beautiful newly updated condo 2 bd/1 ba duplex unit, on a quiet access road between Princeville and Hanalei, avoiding the bustle of the main Princeville thoroughfare. Relax in the natural tropical landscape and take advantage of all the northern side of Kauai has to...
Exotic garden cottage at amazing volcanic fissure
Escape to our cozy and romantic gem nestled in the heart of paradise. Our garden cottage is a stunning specimen of natural beauty located between magnificent Volcano National Park and the historic town of Hilo. Provides easy access to both attractions.The stunning...
Oceanfront & On the Beach! Mahana 114 Groundfloor 1 bed/1 bath, sleeps 4
Aloha! ~The Mahana has one of the nicest locations on Maui. Every unit is ocean front, about 50 feet from the waters edge with gorgeous views and waves rolling in almost underfoot. There is currently a Monk Seal that has been sunbathing directly in front of our...
nNEW KITCHEN REMODEL! Amazing View!
Condo, 1 bedroom + other (See Description) 2 baths (Sleeps 4)Peace of mind is important for where you are staying. Our cleaning care professionals have been trained to properly follow all CDC, VRHP (Vacation Rental Housekeeping Professionals) and VRMA (Vacation Rental...
Beautiful! Light & Airy Top Floor Condo! 3 Bed, 3 Bath + Lanai. Pool and Jacuzzi
This beautiful condo has been artfully designed with your comfort in mind. Fall in love with the white board and batten walls, natural contemporary furnishings, and high quality linens and bedding. Your home away from home comes fully stocked with kitchenware, small...
KR206-Beach Front /Ocean Views - South Maui Condo/AC in bedroom & living room
Unit 206 at Kealia offers a luxurious beachfront lifestyle, providing direct access to the beautiful Sugar Beach. This vacation rental condo is meticulously designed with a custom kitchen and bath featuring elegant granite countertops, modern appliances, and a walk-in...
OCEANFRONT PUAMANA 136-1 - FUN IN THE SUN!
Aloha E, welcome home. This beautifully remodeled oceanfront home at Puamana is like no other getaway. Incredible ocean views that soothe the spirit and calm the mind. Experience a feeling of joy (hau'oli), peace (maluhia) and love (aloha) here. Elegantly furnished,...
Ko Olina Resort, The Sunset Villa - Beach Tower 6th floor Beach Villa- sleeps 5
6th Floor Beach Tower, 2 Bedroom 2 Bath Ko Olina Resort Beach Villa, with Gorgeous Sunset Ocean Views. 2 Units from Ocean-Front! Breath-taking Panoramic Views!*5 person maximum (including kids).Enjoy spectacular ocean views from this luxurious Villa. Situated on lagoon...
Panoramic sea view
Luxury one bedroom two bath ocean view condominium at The Whaler. Located on the 8th floor, with panoramic ocean views, view of black rock and newly remodeled!! Clean & Fully equipped! One of the best condos at The Whaler!! New tile, carpet, paint, and quartz...
Luxe retreat with hot tub and pool access, private W/D, grill, AC, & gas range
Hale HaupuOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to your tranquil Hawaiian getaway! This newly-constructed upscale home is nestled in a quiet neighborhood away...
You'll Love The Ocean Views! 5 Star Hospitality! Hoʻokipa at Wailea Ekolu.
ALOHA!Immerse yourself in the warmth of Aloha at Our Maui Condos - Ho'okipa at Wailea Ekolu Village. Discover the true meaning of Hoʻokipa through our exceptional Wailea Ekolu home. Enjoy breathtaking Maui sunsets with panoramic views of Molokini and Kahoolawe.Our...
Enjoy The Beauty Of Kona! 3 Spacious Units, Oceanfront, Amazing Dining Options!
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
WBH D225 Aloha Ola2 – Relax in Oceanfront Paradise
Summary:This family-friendly beachfront, second floor 1-bedroom/1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper allowing the unit to sleep up to 4 people. Just steps from the...
Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8
IMPORTANT: Hawaii Senate Bill 1396 (SB1396) has been signed into law by Governor Josh Green. The legislation, signed on May 27, 2025, increases the state's transient accommodations tax (TAT) and introduces new fees to fund climate change mitigation and environmental...
Oceanfront Haven - Kihei Surfside #411 - Fun and Relaxation!
Kihei Surfside #411 – Oceanfront Views, Split-Duct AC, and Comfort for Up to Four GuestsWelcome to Kihei Surfside #411, a bright and airy 1-bedroom, 1.5-bathroom oceanfront condo offering panoramic views of the Pacific Ocean and Maui’s southern shoreline. Located on...
Hale Kanani Kauai: Steps to Hanalei Bay w/ AC, Mountain & Waterfall Views
Hale Kanani is NEWLY renovated inside and out! With fresh paint, brand new cabinetry, vanities, quartz countertops and flooring throughout, as well as a new high-performance washer and dryer, on-demand water heater and dishwasher, this two-bedroom, two-bath home will...
Jungle Oasis - Large 3-bedroom Post & Beam Farmhouse on 20 Acres of Privacy
This one-of-a-kind 20-acre off-grid property backs onto thousands of acres of state land and offers the ultimate in comfort and privacy.The home is nestled in pristine jungle close enough to the ocean to let the sound of the waves lull you to sleep at night.The forest...
This Is Your Home away from Home! Well equipped condo and breathtaking Views!
Your vacation of a lifetime starts with sprawling ocean, beach and mountain views. The cool northwest exposure #407 allows for views of sublime sunsets, beach activity on Kamaole I and the whirling windmills of the West Maui mountains. The lanai patio is the perfect...
Wailea Beach Villas | PH201
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements everywhere you look. This contemporary vacation residence spans 2,500 square feet and captures the true allure of vacationing in...
SPECTACULAR OCEANFRONT PENTHOUSE - Air Conditioned 3 Bedroom/3 Bathroom
Poipu Makai B3 is located on a bluff a couple of yards from the water with stunning, full uninhibited views of the ocean. Enhance your senses – the visual beauty of the waves crashing against the shoreline and the gentle sound of the living and breathing sea. Spend...
Wailea Ekahi Village | 23C
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you a relaxing, island-inspired retreat. Nestled within 34 acres of lush tropical landscaping, 23C is a ground-floor...
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
You will love the spectacular views from this luxury one bedroom, tenth floor, oceanfront condominium which overlooks Maui's beautiful Kaanapali Beach. It is located in the "Lanai building" at the highly rated Mahana at Kaanapali Resort.With our unobstructed views, we...
Papakea K404 - Penthouse with Gorgeous Ocean View!
Welcome to our home at the Papakea Resort, a 13 acre oceanfront resort with a true feeling of aloha. The complex is comprised of two sets of low-rise buildings, each with its own oceanfront pool area including a spa, a covered cabana and multiple gas barbecues. The...
Spring/Summer Fill in Special 249/nt Updated Designer Condo w/ Ocean Views
Welcome to Grand Champions 79! Located in the lush Wailea resort area, this 1 bedroom/two bath villa has been completely updated with new furnishings, a plush new King sized mattress and a fresh paint job. Once you step inside the professionally designed bottom floor...
Most desirable Ocean View Location 5 min walk to beach
At Maui Kamaole enjoy Hawaiian resort living on 23 lush tropical acres featuring 2 large swimmings pools with waterfalls and hot tubs, tennis courts and bar b q’s. Unit J117 is bright, beautiful, air conditioned with a Lanai and Ocean view. The fully equipped modern...
Discover the Natural Charm of Old Hawaii. Completely Relax & Recharge Your Soul
Staying at the Guest House at River Estate feels like stepping into your own private piece of old Hawaii—peaceful, lush, and untouched. The moment you arrive, you're embraced by the surrounding gardens, the gentle sound of the river just outside, and the unmistakable...
Remodeled 1BR Kihei Condo: Ocean Views, Gourmet Kitchen, Steps to Kamaole Beach
Kihei Alii Kai 1BD/1BA Remodeled with Ocean Views - Book 5 Nights, Get 1 Free!Kihei Alii Kai 1BD/1BA Remodeled unit with Gorgeous Ocean Views and Maui Sunsets from the Spacious Lanai.Beautiful remodeled 1 bedroom, 1 bath fully furnished condo is ready for your Maui...
Luxury Big Island villa steps away from the best beach, sleeps 10!
Located in a prime position, within the gated, luxury enclave of Pauoa Beach, in the Big Island’s Mauna Lani Resort, the Pauoa Beach Oceanfront Villa delivers a 5-star vacation rental experience. Travelers seeking elegant surroundings, access to private Club...
Cozy Space - 1 Mi to Ocean!
Experience the best of The Big Island from this 1-bath Keaau studio! This vacation rental features a comfortable living area with lovely natural lighting, a well-equipped kitchenette, and access to the area’s most popular sites. Catch some rays at Shipman Beach /...
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
• Split A/C units• King bed• Remolded 2019• Close to swimming poolKamaole Sands unit 6-302 was fully remodeled in September 2019, this bright one bedroom, two full bathroom retreat awaits you. Enjoy views of the Pacific from your third story lanai, freshly...
Charming 2-bedroom condo with ocean views in Keauhou with WiFi, fitness room, AC
Enjoy a peaceful stay at this fabulous 2-bedroom, 2 bath condo in Keauhou. Each bedroom has it's own bathroom, king bed, and separate temperature controlled AC unit. The bathrooms are equipped with a hair dryer and bathtub. There is in-unit washer dryer, and the condo...
Premier Oceanfront Retreat in Lahaina
Experience the epitome of luxury at Kaanapali Shores 502. This beachfront residence, renovated in November 2024, offers an unmatched blend of elegance, comfort, and stunning natural beauty. Spanning over 1,500 square feet, this two-bedroom, two-bathroom sanctuary...
Oceanfront Kihei Paradise Vistas
Summary:Spacious and elegant. Completely remodeled in April 2024, no expense was spared to create our gorgeous oceanfront oasis. This one-bedroom, condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is within reach....
Mauna Lani Palm VIllas F-1 Townhome
***DISCLOSURE (7/21/21): Home is listed for sale and guests may be required to accommodate showings with 48 hours notice.We look forward to welcoming you to this never before rented slice of heaven! Palm Villas at Mauna Lani is a tropical paradise just minutes away from...
Peaceful Private En-suite on Kona Coffee Farm
Get out of the hustle and bustle of downtown Kona and into your own private paradise. This suite offers privacy, ocean views, and acreage to explore. Enjoy the beauty of coffee trees, tropical fruit and nut trees, and the sounds of nature. This property is on a quite...
Beachfront Vacation Rental with AC throughout
This beachfront home on Hanalei Bay offers 3 bedrooms, 2 baths, and air conditioning throughout. Just steps from the sand and minutes from Hanalei town, it’s the perfect beachfront Hanalei location with views of Bali Hai. The Master Suite features a king bed and en...
The Jungalow is a charming renovated bungalow minutes from Volcano National Park
The Jungalow is a charming bungalow nestled among native hapu'u tree ferns and ohi'a trees in the high rain forest. The Jungalow has been lovingly restored with attention to detail. Recent upgrades include new exterior and interior paint, new driveway and landscaping,...
Your Hawaiian vacation starts here!
Welcome to Kona Shores, a complex situated right on Alii Drive, a designated Hawai‘i Scenic Byway (Ala Loa Foot Trail). This ground-floor, end-unit condo offers easy access to Alii Drive and is just one mile from downtown Kailua-Kona, where you'll find shopping,...
3BR/ 2BA Home + Own Private Tropical Orchard!
Summary:Your Tropical Home with a Bonus Orchard! Welcome to our inviting 3-bedroom, 2- bathroom home in lush Keaau. Wander in the backyard orchard and pick fresh fruit for your morning smoothie. With comfortable bedrooms, a fully-equipped kitchen, and a cozy living...
Popular Ground Floor 2BR/2BA villa Ko Olina Beach Villas
*Brand new furniture! New couch, new chairs, new coffee table, new stools, new dinning table and chairs and mattresses (As of April, 2025)This spacious Villa is located in the more secluded Beach Tower. Villa faces the sunset side of the Beach Villas at Ko Olina's 2nd...
Perch - Kihei Garden Estates
Discover beachside bliss in Kihei! this enchanting home captivates with its blend of cozy ambiance and unbeatable location. Steps away, discover a plethora of restaurants, shopping, dining, and coffee spots, all within walking distance. This tranquil refuge offers a...
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Maui County Permit # STHA 2016/0006Tax ID TA and GE 170-361-2416-01NOTE: Price listed is for 1-2 guests, add $45 per person up to 4 guests maximum Considered one of the best locations in all of Hana town area, the Gold Coast of Hana. Centrally located near the best...
Heavenly Hawaiian Hideaway...Oceanfront
WELCOME TO HALE I'A U'i: YOUR HAWAIIAN PASSPORT TO PARADISEExperience the ultimate seaside escape where luxury meets the natural beauty of the Big Island.Located in Puako, a charming community with an "Old Hawaii" feel, you will find yourself transported back in time...