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.
Pinnacle: Upcountry Maui Retreat with Pool & Ocean View
Permit: STPH 2013/0024TA-091-083-1616-01 / GE-091-083-1616-01TMK-270031060000Fabulous views, privacy and quiet were foremost for us in choosing where to build our dream home in Hawaii. We looked for several years before finding this special Maui hilltop location on the...
Modern and Luxurious Beachfront Property at Polo Beach
Maui beachfront elegance Polo Beach Club is conveniently situated at the beginning of Makena and the Wailea oceanfront pathway that connects the luxurious Makena and Wailea Resorts. The interior is open, light and bright, fully furnished with creative flair and luxury....
(4101/02/03) 3Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4101/4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 3 bedrooms, 2 of which have King size beds and two large bathrooms with showers to rinse off after a...
A Gallery of Views and Art at Waikiki
Imagine indulging in a Hawaiian vacation experience from the moment you wake up and open your eyes. Leisurely laze in bed as you enjoy sunrise through the wall-to-wall windows from a variety of angles. Watch the backdrop throughout the day like an ever-changing...
Maui Resort Rentals: The Whaler 563 - Gorgeous 5th Floor Studio w/ Fantastic Pacific Ocean Views!
Enjoy gorgeous views of the Pacific Ocean and Maui's neighboring island Lanai from this luxurious 5th-floor studio suite at the Whaler in the heart of Kaanapali Beach.Beautifully upgraded, suite 563 offers a spacious 500+ sq. ft. living interior that can comfortably...
Hawaiian Retreat w/ Ocean Views in Captain Cook!
Indulge in the ultimate Hawaiian getaway at this stunning 3-bed, 3-bath vacation rental house in Captain Cook. Upon arrival, you’ll be greeted by 3 manicured acres of mature fruit trees. Past the front door lies access to the ocean-view lanai, which is the perfect...
0.1 mile to Waikiki Beach-Renovated 2B/2B Condo/Free Parking
Central Waikiki Condo. 2 bedrooms, 2 full baths, plus 1 free parking; new A/C.★ Sleeping arrangements* 2 queen beds* 2 full size sofa bed* 1 bunk bed that can sleep 2 (up to 250lb per bed)* 1 floor mattress* 1 crib.★ 1 assigned FREE parking spot, hotel public...
SPECIAL Rates - Mauna Kea Fairways South 14: Incredible Ocean Views
Hawaiian Charm Mauna Kea Fairways South 14 - Incredible Ocean Views.This comfortable Mauna Kea home offers vast indoor/outdoor space and is the perfect home for your next Hawaiian vacation. The ample lanai overlooks gorgeous ocean views over the famous Mauna Kea Golf...
Upgraded 3 bed w/Ocean View, Pool, Hot tub, 2*King
Summary:Enjoy daily sunsets over the ocean right from living room. This Corner unit is a privately owned part of Wyndham hotel, provides you best of both worlds - pool, tennis, spa, gym, billiards, ping pong etc. while being completely remodeled with brand new...
Hale Ylang Ylang: Steps to Beautiful Hanalei Beach
A relaxing Hanalei Vacation can be yours at Hale Ylang Ylang. Steps to the beach and near the heart of Hanalei, this luxury two bedroom townhome has views of the ocean and our north shore mountains.Relax in this comfortable home in Hanalei Bay. Feel more like a local...
Auntie Kali's Cottage: 2 BR Wailea Home with Pool & Tiki Bar
Experience the best in Maui Hawaii when you stay in this 2bedroom/2 bathroom private Hawaiian plantation style cottage located within minutes of the Luxury Resorts including The Four Seasons, Maui Wailea & The Grand Wailea Resort on Maui’s South Shore. When you open...
Kona Hillside Estate - Gated Property with Lap Pool
Welcome to our family's private gated estate located on the beautiful hillside of Hualalai mountain in Kailua-Kona. We recently renovated our 4,000 SF home and enjoy hosting guests when we have availability since 2022.Guests will appreciate soaring ceilings, open living...
Steps To Kailua Beach
Our beautiful home has been featured in Hawaii Home Magazine and has received a best in class award from the Hawaii Builders Association. The home is within a 2 minute walk to Kailua Beach Park, the Kalapawai Market and Buzz's Steak house. There is ocean, mountain and...
Gorgeous 5th Floor 2 Bedroom Condo. - Kihei Surfside #501
Kihei Surfside #501 – Top-Floor Oceanfront Views and Tranquility in a Rare 2-Bedroom LayoutWelcome to Kihei Surfside #501, a rare and spacious 2-bedroom, 2-bathroom oceanfront condo perched on the top floor of one of South Maui’s most sought-after properties. With...
Hokulani 836 at Honua Kai Resort ~ Extra Large Lanai With Amazing Ocean Views
Welcome to your Hawaiian paradise Hokulani 836 at the Honua Kai Resort! You'll fall in love with the stunning ocean and mountain views from the 8th floor and the huge private lanai that's perfect for entertaining or enjoying a delicious meal while the sunsets in the...
Absolute Beachfront with Million-Dollar Views at Hale Mahina A-302
Welcome to Hale Mahina A-302! With a direct oceanfront view and located on a secluded and gated white-sand beach, our condo is perfect for those looking for a quiet and relaxing West Maui getaway.Our favorite thing about this condo is the VIEW! Unobstructed views of the...
AwardWinning|PrvtBeach|RitzCarlton|$20K90"TV|3Spas with Beachfront Jacuzzis,Gym
Summary:-Call 310-579-2494 for booking availability-Out of 8 million listings, very rare selection as Airbnb Luxe-Prior rentals by A-list celebrities for six-figures-Corner single-level (with no steps) beachfront estate 12 min from Ritz Carlton with its OWN PRIVATE...
Frontal 5-Stars Oceanview Beach Villas at Ko Olina 2-Bedroom & 2-Full Baths
2nd most reviews on VRBO!!! See other unit we have available: VRBO #311592The Resort: Beach Villas at Ko Olina.The Beach Villa is located at Ko Olina, Hawaiian for Place of Joy. Ko Olina is a picturesque resort located on Oahu's western side nestled away from the hustle...
Luxury Wailea Condo - Incredible Ocean Views! 5 Star Reviews. Multi Zone AC.
Welcome to Olu’olu (meaning a “happy" home, in Hawaiian), which it will always be! Enjoy beautiful Wailea, in South Maui at our home!Olu’olu is remodeled, beautiful and relaxing. Your first view from the living room lanai, across the Wailea Blue Golf Course, to...
Look No Further...All You Need Is Here....including the sea turtles!
YOUR PERFECT MAUI VACATION ADVENTURE AWAITS! You'll enjoy amazing views from the lanai, including whale watching ( Dec-April) and sea turtles and the occasional visit from a monk seal year-round! Sunrises over Haleakala, tranquil Ma'alaea Bay, and of course surfers....
Hawaiian condo next to the Kaanapali Golf Course
Ka'anapali Plantation 54 is a 2-bedroom, 2-bathroom unit that offers split A/C in every bedroom and a main living area spanning out to the kitchen and ocean views from this ground-floor unit. Unit 54 can accommodate up to 5 guests. The master features ocean views, a...
Perch - Maalaea Banyan: Oceanfront 1BR | 20 Steps To Beach
Welcome to your recently updated home away from home! New appliances, new kitchen, and new paint throughout. Enjoy the panoramic ocean view while you are relaxing on the couch or preparing a drink in the kitchen. As a ground floor unit, you can extend your relaxation...
Beautiful Maui Kamaole 2 Br, 2 Bath condo with Ocean view! New Summer/Fall rates
Beautiful VRBO Premier Partner Designation and 5 Star Property is in the B building, across from main pool and a 5 min walk across from Kihei's favorite beach. 2 bedrooms, 2 bath, over- sized unit with many high quality, unique upgrades rarely found in a vacation...
Hawaiian Chic Crater Retreat- a tropical jungle escape in a secluded crater
***FYI- swimming pool will be closed April 15th-May 15, 2024 for repairs***Being on the ocean is amazing, but is it as amazing as having a one of a kind condo in a secluded crater? It has many of the same amenities as a $1000/night nearby resort does, for a much better...
Remodeled High Floor Waikiki Studio
This charming studio nested on 35th floor of the Hawaiian Monarch building is your perfect place to enjoy your Waikiki vacation! With awesome views of mountains and canal, the condo comes with a queen bed, a full bath and a kitchen that includes an induction cooktop, a...
Fabulous, Renovated Large 3BR Condo on Kahala Beach
Welcome to our newly renovated slice of paradise at Kahala Beach! Nestled in one of the most sought-after neighborhoods in Honolulu, this spacious 3-bedroom, 2-bathroom property promises a luxurious escape for your Hawaiian getaway.Step inside and be greeted by a...
Oceanfront with A/C Remodeled Amazing Views of Whales
Relaxing and Lovely Property on the Ocean, with Both Ocean & Garden ViewsThe condo provides a great ocean view and oceanfront location that keeps all the traditional Hawaiian Charm and feel in a low rise.. We have lush plantings and gardens, cool trade winds, and sounds...
KBM Resorts | FREE CAR | Kaanapali Shores | Ocean view | 2-Bedroom Condo with Stunning views & Great for Families! KS-260
Sleep to the sound of waves in this 2-bedroom, 2-bath villa on Kaanapali Beach. Stunning ocean views, A/C, full kitchen, lanai, resort pools, tennis, and steps to dining, shopping, and Black Rock.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Spectacular home with ocean views across the whole of the north shore.
Oceanview Paradise at Sunset BeachLocated on the majestic North Shore of Hawaii, this 3-bedroom, 3-bathroom retreat offers a slice of paradise with panoramic ocean views. Just a short stroll away from the world famous Sunset Beach, this home provides the quintessential...
Breathtaking Oceanfront Home on Lava Rock Beach.
Summary:Embrace the beauty of Hawaii with a stay at our breathtaking oceanfront home, where you're surrounded by the soothing sounds of the waves and the gentle Tradewinds. From our expansive, floor-to-ceiling windows to multiple lanais, you'll enjoy panoramic views of...
Stunning BEACHFRONT Ground Floor Condo – Fully Renovated & Ready to Welcome You
Experience the ultimate in Tropical Beach Living at this beautifully renovated, ground-floor 1-bedroom, 1-bath condo at Kihei Sands. Complex located right on the beach, this chic retreat combines modern style with the laid-back charm of Maui. With a design that blends...
Dolphin House by Gather: North Shore Escape w/ Direct Beach 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.Welcome to Dolphin House by Gather, a charming...
Maui Sunset #A216 - Oceanview King Bed, 1BR, 2 BA Condo
Maui Sunset is a beautiful oceanfront resort and is the perfect vacation home on Maui. Swim in the large swimming pool or just enjoy sitting on a chaise lounge by the pool or in the jet spa. It is especially beautiful in the evening relaxing under the stars and enjoying...
Spacious 3 bedroom 3 1/2 bath condo in Poipu Kai
Bring the whole family to this 3 bedroom 3 1/2 bath clean ,updated beach condo. We are located in the Poipu Kai greenbelt just a short walk to the beach with access to two pools and a Jacuzzi. Keep cool with AC in all bedrooms and ample space to keep the whole family...
Kauai North Shore Oceanfront - Mountain View Beachouse TVNC#1136 Tsunami Zone
Hawaiian Island Beachfront cottage with an incredible location on the North Shore of Kauai in between Hanalei and Haena close to Tunnels. The 3/4 acre property features a large sandy beach point. Some of the islands best snorkeling and shelling right out front of the...
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
After a full day of enjoying all that Maui has to offer, come home to your air conditioned oasis in the heart of the Kaanapali resort. Maui Eldorado J115 has been totally rebuilt to reflect the island lifestyle that you deserve.A ground floor unit in one of the best...
Maui Resort Rentals: Luana Garden Villas 2A – 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. Villa 2A's north facing orientation offers a Shady respite from West Maui's legendary endless sun and its designation within "Grounded" collection at the Luana...
Oceanfront Penthouse Sleeps 8! New Central Air! Gorgeous 180° Views- w/Loft!
Penthouse views, three breezy bedrooms, and front-row whale watching. This top-floor oceanfront condo offers Moloka‘i sunsets, honu in the surf, and open-air dinners on the lanai. With central A/C, three baths, and Papakea’s pools below—you may never want to...
A 5-Star Estate, Large Groups, Luxury Living
This luxury condo is situated a short walk from the beauty of the beach! A 3,700 square foot, 3 bedroom, 3.5 bath gem, it is the ideal place for a quiet retreat. Features a Master Suite with private lanai and two additional bedrooms with en suite baths, sleeping up to a...
Cozy ground floor condo, lush lanai, dining nearby
Welcome to Maui Kamaole F101 – your perfect island retreat! This beautifully appointed ground-floor condo features 1 bedroom and 2 full bathrooms, comfortably accommodating up to 4 guests. The dual-bathroom layout is ideal for families or couples traveling together....
Hawaii Life Rentals Presents Villas of Kamalii 17
This bright, spacious three-bedroom, three-bathroom townhome is located at Villas of Kamalii, in the prestigious resort community of Princevile. Perched on the highest part of world-famous Makai Golf Course, enjoy stunning mountain and waterfall views from your private...
Penthouse Condo with Ocean Views
Vista Waikoloa – Your Big Island Escape AwaitsPerched on the third floor in a coveted corner position, this newly updated condo is your private oasis in paradise in the Vista Waikoloa complex. Step inside to a light, airy tropical retreat filled with fresh décor and...
Beachfront Family Estate. Great for multiple families.
Nestled in central Kihei on the northern end of picturesque Halama Street, this family-owned, legal short-term rental features two accommodation options on a beachfront property: a two-story building with four individual units and a detached 2-bedroom cottage. Guests...
2 Bedroom Penthouse and Amazing Ocean Views!
Enjoy a top floor penthouse villa, directly overlooking the ocean and newly renovated pool at the Mauna Lani Terrace! Building "H" is one of the most requested and boasts a location directly on the seafront, nestled between the luxurious Auberge Hotel and the private...
VACATION DATES: OCTOBER 18-25, 2025: 2BR/2BATH VILLA KAANAPALI
ENJOY AN OHANA HAWAII EXPERIENCE AT A VALUE PRICE. EXPERIENCE PERSONAL CUSTOMER SERVICE FROM AN OWNER OF THIS VILLA TIMESHARE.OFFERING OUR 2 BEDROOM / 2 BATHROOM UPPER FLOOR OCEANFRONT VILLA AT $600 DAILY RENTAL PRICE. GUARANTEED UPPER OCEANFRONT VILLA ON FLOORS 9-...
Downtown condo with pool, tennis, & mountain view - walk to beach
Waikiki Sunset 1605Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your newly renovated 1-bedroom, 1-bath condo at the Waikiki Sunset in Honolulu, HI. This apartment...
(4102/03) 2Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 2 bedrooms, one with a King size bed and large en-suite bathroom with a shower to rinse off after a day...
Pili Mai Family Fun Condo, AC, Game Room, 2 Bedroom, 2.5 Bath, Sleeps 6
FAMILY FUN at Pili Mai, 2br + Game room (bumper pool, poker table, classic video game console, board games, piano, masks and snorkels, beach chairs, croquet, and small yard for the kids to play) 2.5 bath, sleeps 6, no stairs, back yard lawn. Condo is located near the...
Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking Views 14T 1-2
This is a legally permitted vacation rental according to the County of Maui ordinances.Spacious Lanai Retreat: Kapalua Maui's Golf Villa with Breathtaking ViewsImmerse yourself in the epitome of luxury with our recently refurbished 1-bedroom, 2-bathroom condo, nestled...
Epic Forest View, A/C, Fruit Trees, Beach 5m drive
Experience this forest retreat complete with a cozy queen bed, AIR CONDITIONING, vaulted ceilings, convenient kitchenette, half bath, and an outdoor hot/cold shower. Relax on the expansive deck facing breathtaking panoramic views of the untouched jungle. Immerse...