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.
Hawaiian Family Paradise Retreat – Near Beach & Golf!
Escape to your paradise in this luxurious Hawaiian retreat! This exquisite home offers the perfect blend of relaxation and convenience. Just minutes from the Kohala Gold Coast’s finest beaches and resorts, a short walk to local shops, restaurants, a community pool,...
Westin 2BD Ocean Front - One of only 24 units on property 6/7/2025-6/14/2025
DELUXE OCEAN FRONT 2 bedroom Lock-off Villa - 6/7/2025 - 6/14/2025. This premium, deluxe villa (ocean front NOT just ocean view) in the SOUTH property is amazing with supersized lanai!! Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70%...
New! Upgraded Kiahuna 425 Plus Athletic Club
Rare Find with A/C at Kiahuna Plantation – Newly Upgraded & Steps from the BeachKiahuna Plantation #425 | 2nd Floor Corner Unit | Building 41Looking for cool comfort in paradise? This beautifully updated condo at Kiahuna Plantation now features brand-new A/C — a...
2 BR Luxury Oceanview Condo in Kukuiula
Kainani #1 is a 2-bedroom, 2-bathroom villa nestled in the heart of paradise, offering an unparalleled experience of comfort, convenience, and tranquility. As you step through the ground-level entry, you'll be greeted by the seamless fusion of indoor and outdoor living...
SALE! REDUCED 489nt 4/26/-5/2 2bd2bth condo HUGE 1680sf,50ft to ocean,AC,views
We are very saddened by the devastation and loss of life in Lahaina. Our condo is NOT IN Lahaina, we are 6 miles from it. Thankfully since we are not close to Lahaina, our condo, complex, and all surrounding areas are in the same pristine condition as it always has...
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
*Please note that per Maui county law, that two adults and two minors are allowed per bedroom. We are allowed to host up to 4 adults and 4 minors for a total of 8 guests. This is a private top floor unit of a 2 level home. Our favorite aspects of the home are:*Large...
Oceanfront Kailua-Kona Home, Walk to Kahaluu, Wifi & AC
Welcome to Hale Lula o' Nai'a – "House of the Dolphins" – your oceanfront retreat on scenic Alii Drive!Ideally situated just north of Kahalu'u Beach Park in Kailua-Kona, this prime location offers easy access to surfing, paddle boarding, and snorkeling.Designed for...
2 bed/2 bath luxury condo in sunny Poipu with AC
*** Welcome to our Regency Villa in Poipu *** NEW LISTING!We recently bought this luxurious 2 bedroom condo and fell in love with the garden views, chic decor and the prime location. The boutique resort is one of the newest in Poipu. You will love staying here with your...
Charming Oceanside 2-bedroom condo with A/C in fabulous Kapaʻa
Located in Kapaʻa, this 2-bedroom condo offers an enjoyable stay with 1 queen bed and 1 king bed. The property comes with essential amenities like WiFi, AC, and a washer/dryer. Guests can relax in this adorable and peaceful space, perfect for both short getaways or...
Surfers & Sunsets-Kona Reef Ocean Front Unit
Watch the Surfers from Your Lanai - Kona Reef Ocean Front UnitLight and Airy with direct Ocean Views from the Lanai, Living and Kitchen areas. Large Ocean Front 611 square foot condo with a full 128 square foot Lanai. This fully equipped Ocean Front 3rd floor condo is...
Luxurious 4 Bedroom Retreat, Private Pool, Located in KuKui' Ula Community.
Situated on the upper tier of the Kainani neighborhood in the beautiful Kukui'ula Community, this exquisitely designed, newly constructed custom home, features custom imported teak flooring, cabinetry, vanities, trims, natural wood, stone, lava rock, and hand selected...
Escape to Paradise- AC, Kayaks,Ocean across street
*30 day rental. Please inquire.Come, Escape to Paradise! This beautiful secluded home is in the perfect spot along the Windward shore of Oahu. This 2500 sqft Ka'a'awa, air-conditioned home can sleep 8-10 people in 3 bedrooms and an open den. Planning on working from...
Boutique 1-bedroom condo in Waikiki! WiFi, AC, Pool, Hot Tub, BBQ Free Parking
Enjoy a pleasant stay at this newly rennovated 1-bedroom condo in Waikiki, Honolulu with Free Parking. This 11th floor home features 2 queen beds,a pullout sofa-bed, Japanese tolilet, magnetic arm and rainshower head,perfect for a small group of guests and families....
Oceanfront Maalaea Harbor Two Bedroom Condo within walking distance to beach
We are thrilled to announce the completion of our condo's remodel in January 2025—everything in the unit is brand new! The property offers one private parking spot, with additional off-street parking available. Located on the second floor, the unit features easy...
Modern and Cozy Ocean View Condo - 10% Discount on 7 days Booking
Sugar Beach Resort sits steps away from the Pacific Ocean in North Kihei and a 5-mile white sandy beach that fronts the property. Guest enjoy taking morning and sunset beach walks while enjoying the panoramic view of Pacific Ocean. Watch Humpback whales visit the...
Ko Olina Beach Villas - Beachfront (Beach Tower 709)
Our spacious 1,500 square foot suite is the only beach-front penthouse available for rent at the prestigious Beach Villas Resort in Ko Olina and the only privately rentable condo with panoramic ocean views from every room.Watch the video of our property -...
Huge Luxury Condo | partial Ocean View on Beach 1 BD
Condo, 1 Bedroom, 1 Bath, (Sleeps 1-4) Aloha! Welcome to Paradise! Important: Although this is a privately owned vacation rental home this complex is zoned "Hotel" so not part of any potential changes to vacation rental property use. Welcome to the Honua Kai Resort and...
Mauna Kea Villa 3037 - Architectural Island Estate
This dazzling, single-level, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living and Sonos system, a chefs' kitchen with Wolf and Sub-Zero appliances/wine refrigerator, a dining area with adjoining wet bar, a...
Beautiful Ground Floor Golf Villa @ Fairway Villas Waikoloa
Welcome to our spacious 2 bedroom/2 bathroom premium ground floor villa overlooking the fourth hole of the Robert Trent Jones II-designed Waikoloa Lakes Golf Course. The Fairway Villas complex is a part of the Waikoloa Beach Resort area, located just 20 minutes north of...
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...
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...
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
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...
POIPU BEACH HOME, Kauai's famous sunny south shore.
What's not to love! This house is situated in a very peaceful neighborhood within walking distance to everything that Poipu has to offer.World famous beaches, restaurants, resorts and spas. Being in the Poipu Kai Resort provides Guest Pools, Tennis, and an expansive...
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...
Ocean View Chic Condo at Carlsmith Beach Park in Hilo!
Welcome to Sandy Toes, our chic one bedroom condo at Carlsmith Beach Park in Hilo, Hawaii! On the fourth floor our private lanai boasts lovely ocean and park views below. Hang out on the lanai lounger or eat your meals al fresco while looking out at the ocean and...
Park Lane Ala Moana 8803
Welcome to the exquisite Park Lane at Ala Moana residential resort community. Park Lane’s luxury residences offer resort-like amenities and are ideally located in the heart of Honolulu, just across the street from Ala Moana Beach Park. Built on the ocean side of the...
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, & steps to dining, shopping, & Black Rock.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with...
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...