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.
SEArider TWO at Turtle Bay (1 bedroom / 1 bath) - Kuilima Estates East
Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal...
Hualalai Golf Villa 4202 - Oceanfront + Prime Location + Room Service
Whale watch while listening to the breaking waves from the shoreline from the Primary bedroom's private lanai with unobstructed ocean views! This beautifully appointed three bedroom villa has over 2,500 square feet of living area. Each of the three bedrooms are...
White Sands Village #217 – Perfect Tropical Escape
Summary:Whether you seek serenity along ocean shores or adventure beneath the waves, White Sands Village offers an unforgettable getaway immersed in the culture of the Hawaiian Islands. Located on Hawaii’s Big Island in beautiful Kailua-Kona, this 2-bedroom vacation...
Laid back Molokai beach-hideaway
One of the few Paniolo Hale units within steps to the beach! 2 Bedroom, 2 Bathroom, & Wrap Around Lanai with Ocean ViewsOur spacious, ocean-view townhouse is only steps from Kepuhi Beach. This 2000 sq ft townhouse feels more like a beach home with its generous living...
Naupaka Hale - Lanikai Beach Home & Cottage
NAUPAKA HALETA-151-566-1312-02THIS PROPERTY RENTS ONLY MONTHLY FOR 30 DAYS AND LONGER.Idyllic classic Hawaiian style vacation rental home on large lot with huge sandy beach right in front of your very eyes. This beautiful vacation rental home offers breathtaking views...
Wailupe Seaside Haven: Beachfront Luxury Home w/ Pool & in City Proximity
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 Wailupe Seaside 4 Bedroom by...
Luxe, 1st-floor condo with sunset mountain views, lanai, pool, hot tub & gym
Plantation at Princeville #511Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find your own little piece of paradise on the spectacular North Shore of Kauai at this garden-level...
Best of Kaanapali Ali'i Suite 382 - Walk Whalers Village - Ocean Views
E komo mai (welcome) to your Hawaiian paradise on the eighth floor of the renowned Kaanapali Alii Resort, where island elegance and modern luxury come together in harmony. This two-bedroom, two-bathroom suite comfortably sleeps six guests. This suite is uniquely located...
❤️PiH❤️ BLUE TRANQUILITY ★ E-Bikes ★ Golf Clubs ★ Heated Private Pool & Spa ★
Enjoy Big Ocean Views, Hapuna Estates Amenity Center with Waterslide, Fitness and covered Hale's ** NEWLY ADDED ** Enjoy Blue Tranquility's 2 Adult E-bikes & Complimentary set of Men's and Women's Golf Clubs. Welcome to Blue Tranquility, a guest favorite, exquisite 4...
Estate on Tropical Acre - Harmony in Paradise
Modern home, over 3,500 sq ft; a resort-quality property that can sleep up to 10 guests, on an amazingly lush, fully-landscaped acre. Large living room, exceptional kitchen and dining areas, four lovely bedrooms, a study has been equipped with children in mind, and...
Remodeled Kiahuna Ocean View Condo with A/C, Close to the Beach! No cleaning fee
Kiahuna Plantation Beach House #179 – Our Hawaiian HeavenWe welcome you to our Kiahuna Plantation Beach House. Unit #179 is our home away from home, and we look forward to sharing it with you. Our unit was completely remodeled with an open concept kitchen with quartz...
Stunning Panoramic Ocean Views
Welcome to Maui Ka’anapali Villas!Our beautiful One Bedroom, 2 Bathroom Corner Unit is extremely rare! Located on the 5th floor of the Aloha Tower featuring breathtaking panoramic ocean views from the Living Room, Open Kitchen and the Bedroom. Enjoy both morning...
Oceanfront Bliss Pool & Stunning Views Hono Kai C3
Relax and rejuvenate with stunning Ocean and Haleakala views from your living room and lanai. Perfect for whale watching, this beachfront escape features a fully stocked kitchen and all the comforts you need. Lounge by the oceanfront pool, savor BBQs, bask in the Maui...
High Floor Ocean View Wyndham Waikiki Resort
Aloha! Enjoy the boutique-hotel ambiance of the Royal Garden Hotel and the beautiful Hawaiian tropical setting. It’s the perfect spot for your vacation, business trip, or a refreshing getaway.Our condo is located in the heart of Waikiki, just a short walk from the main...
great for families & professionals
We welcome everyone and especially love hosting families and traveling professionals for extended stays. Easy access to highways in both directions for access to Waikiki, downtown, military bases and hospitals. Our guest house is completely free-standing and elevated...
4 BDR, 3 BR, A/C, walk to beaches, restaurants and The Grand Hyatt
Nani O'Hana is a 4 bedroom, 3 bathroom luxury home located in the quiet neighborhood of Poipu Kai. The house is located in the Lanai Villas subdivision of Poipu Kai community where you can easily walk to beaches, tennis courts, pool, Grand Hyatt, Spa, restaurants and...
🏖️Air-Conditioned Ocean Front Free Standing Townhome! | Sleeps 6 | vrKCV🏖️
Welcome to Hale Kai Aloha – Kona Onenalo #10!Experience island living at its finest in this free-standing townhouse located within the exclusive gated community of Kona Onenalo. Slide open the floor-to-ceiling doors and step onto one of two lanais to enjoy breathtaking...
Hilton Hawaiian Village Lagoon Tower, private beachfront resort
Hilton Hawaiian Village one-bedroom villa in the heart of Waikiki.Thank you for choosing Dash Realty Group of Windermere, Florida. We are a registered Fla. Seller of Travel Ref. No. ST42435.Our rates are based on a standard island view, additional views may be available...
Spacious two-bedroom split-level Kihei condo
Welcome to Maui Kamaole M210, a stunning 2-bedroom, 2-bathroom split-level condo that combines modern comfort with tropical island charm. Located in one of Maui's most sought-after complexes, this beautiful retreat offers everything you Welcome to Maui Kamaole M210, a...
Unforgettable Ko Olina 11th Floor Penthouse, Direct Ocean View
This ocean tower 11th floor two bedroom, two bath 1466 SF luxury Penthouse villa is located in Oahu's most prestigious beachfront destination - Beach Villas at Ko Olina ('Place of Joy'). You'll experience breathtaking panoramic ocean views from your private lanai while...
Mauna Lani Designers Golf Course View Beach Club Access
The Fairways at Mauna Lani is a privately-gated development located in the prestigious Mauna Lani Resort located on the sunny Kohala Coast of the Big Island. Enjoy golf on the world-renowned championship Frances H. I'i Brown North and South Golf Courses. Mauna Lani also...
Cozy Oceanfront 2BR Condo with Pool and Epic Views
Summary:Embrace the ultimate Hawaiian escape in this stunning oceanfront condo, meticulously remodeled to capture the luxurious yet laid-back essence of Maui. Enjoy breathtaking views as sea turtles gracefully swim by while you sip your morning coffee on the private...
🏝️SUMMER Special -Ocean View Renovated Condo in Napili🏝️
This one bedroom/one bathroom condo has been remodeled from top to bottom and beautifully furnished with clean modern design, perfect for your Maui getaway. The lanai has sitting area to enjoy morning coffee or sunset cocktail overlooking the water and the island of...
Beachfront Estate On The North Shore with AIR CONDITIONING 90/TVU-0043
Hukilau Beach and the blue waters of the Pacific Ocean on one side and the Ko'olau mountains on the other, Hale Lani lives up to its name as the “House of Heaven.” The perfect choice if you’re traveling with a large family or a group of friends, this home is one of only...
Minutes From Kealakekua Bay In The Midst Of Kona Coffee Country
The property is a one-acre lot with a small mango orchard (30 trees), fruit trees (lime, lemon, orange and avocado) and a beautifully manicured landscape. The cottage is separate from the main house, so your privacy is assured. There is a bathroom (with tub/shower), an...
Secluded Waimea Hideaway w/ Lanai & Views!
Experience the beauty of Waimea, HI, like a local while staying at this spacious 3-bedroom, 2.5-bath vacation rental! With a lanai and outdoor dining area, you can enjoy the stunning views of the surrounding mountains while enjoying a home-cooked meal. Explore the...
Beachfront Oasis for Two on Sugar Beach in Kihei - Kealia Condominiums #302
Kealia 302 offers beachfront living right on Sugar Beach! This beach is known as the best walking beach on Maui. And after a full day of sightseeing, shopping or other activities, you can fall asleep to the gentle sound of the surf. It's the best sound machine in the...
Makena Surf G-201 - Amazing corner unit, Luxurious Renovation, Panoramic Views
Makena Surf G-201 is on one of the most luxurious and prestigious properties on the island of Maui. With oceanfront access and spectacular views, it offers a secluded and tranquil setting for your next island getaway. Unit G201 is located on the second floor of the G...
Beautiful fully AC 2 BR/2BA Kanai a Nalu beachfront condo 20 ft from the waves
Grand reopening 12/20/25/! We helped FEMA house Lahaina fire responders and then fire survivors, and now our condo returns, refreshed throughout with all repairs and replacements complete, as a vacation rental where YOU can “have it all”! Updated photos coming...
PoipuBeach-3rdFl-Partial Ocean- AC-Pool-Garden-313
Private top-floor corner unit in a peaceful building with AC and upgrades—tons of privacy! Enjoy access to the pool, stroll through lush Moir Gardens to reach Kiahuna Beach, and skip the resort fees. Beach gear is included for your convenience. This serene retreat is...
Serene home with enclosed nature walk, meditation spot, & gardens
E Komo Mai Retreat Ohana | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Channel your yogi self and experience the serenity and spirituality of the EKomoMai Retreat....
Holua Moana Hale: Spectacular Oceanfront Home with Private Pool & Spa
Nestled within the private, gated community of Holua Kai in Kailua Kona, Holua Moana Hale offers a seamless blend of modern comfort and barefoot island luxury. Overlooking the rolling greens of Kona Country Club and the endless Pacific beyond, this two-story residence...
Breathtaking Oceanfront Suite @ Kalapaki Bay
Luxury oceanfront suite in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this suite is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate indoor-outdoor...
Malia Kai #12 condo in Kailua-Kona Town!
Three story townhome corner unit located in Malia Kai condominiums w/private carport walking distance from just about anywhere in Kona! Share our private retreat and where you can work from Paradise with laptop workstation featuring a high end 32” screen and the fastest...
Beautiful, Family Friendly 2 Br 2Ba Across Street From Beach.
Beautiful 2 bedroom 3 bed unit offers a quiet getaway and island view. Newly updated furniture and decor. Each building has a pool, tennis courts and barbecues. Quick stroll across the street to Beautiful Charley Young Beach. Great Shopping and dining options are a...
Laule‘a #13 by Gather – Mauna Lani 4BR Villa w/ Golf Frontage, Private Pool/Spa
Welcome to Laule‘a at the Mauna Lani Resort #13, a refined 4-bedroom, 4.5-bathroom retreat on the Kohala Coast where modern elegance meets effortless island life. With golf course frontage, panoramic views of Mauna Kea, and a private pool and spa framed by tropical...
Walk to Dtwn Hilo: Island Escape w/ Pool!
5 Blocks to Bayfront & Beach | 1 Mi to Rainbow FallsPack up for paradise, where relaxation and adventure blend seamlessly. This 2-bedroom, 1-bath Hilo vacation rental places you within just 1 mile of hot spots like the lively Hilo Farmers Market and the breathtaking...
Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC
Mana Kai 314 is a beautifully upgraded two-bedroom condo offering a serene retreat for up to four guests. With panoramic ocean views from the living area and private lanai, this unit provides a front-row seat to Maui's stunning sunsets and soothing wave sounds. Inside,...
Coastal Chic Ocean Front Stunning View w AC
Escape to paradise in this modernly furnished 1-bedroom oceanfront condo! Relax on your private Lanai while watching mesmerizing waves and turtles. Enjoy a fully stocked kitchen, heated pool and hot tub. Fall asleep to the waves crashing in the comfy king-sized bed or...
Newly Remodeled-Quiet Location-Ac-Well Equipped-Meticulous Cleaning
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all new furnishings. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of...
Gorgeous Private Home with Pool and Spa in Waikoloa Resort, Big Island
Our commitment to you, our guests, is to provide a high level of satisfaction through attention to details, high quality amenities and outstanding customer service. Please read on to discover what a special place our Ainamalu home truly is.DISCLAIMER** Please keep in...
Luxurious golf villa with updated appliances
Welcome to Kapalua Golf Villa 20V1, a luxurious 1-bedroom, 1.5-bath condo that can accommodate 4 guests and is located in the prestigious Kapalua resort, offering the perfect blend of elegance, comfort, and breathtaking natural beauty. As you enter the villa, you'll be...
7 Mi to Volcanoes NP: Serene Cottage w/ Deck!
8 Mi to Volcano Golf Course | Picturesque ViewsNamed ‘Halakea Hale (Pineapple House),' this peaceful 2-bedroom, 1-bath cottage combines traditional charm with modern comforts. Sip coffee on the deck as you marvel at the natural beauty of one of the few remaining ancient...
Island Breeze Oasis - Newly Furnished
Welcome to our slice of paradise! Prepare for a vacation that feels like a dream – our villa is not just a place to stay; it's an experience waiting to unfold!Imagine waking up to the sun-kissed charm of four stunning lagoons right at your doorstep. These crystal-clear...
April SALE-9,10,14,15 SALE 159-TreeHouse Vibe AC-WiFi-BBQ-W&D-Cliffs-Sleeps 6
(Please Note we do not rent longer than 7 days)Casa by the Sea Welcomes you.Relax in Paradise with 1 acre of Tropical Jungle to explore and the sounds of the Ocean,Birds & Frogs. 5 Min short walk to Paradise Cliffs & Parks. COME SEE THE ONLY HAWAIIAN ISLAND WITH AN...
Spectacular Lakeside, Bali Hai Mountain View, Fairway Home
Welcome to Hale Mahina! Long hidden as a luxury private residence, this Princeville pearl is now yours to enjoy. All one level, Hale Mahina offers unobstructed expansive views of the bejeweled Nanolokama Mountains and Bali Hai across the lake and the world renowned...
SALE Aug-Dec! Upgraded BeachFront Ocean View 3-BR 2.5BA Villa 1734 sq.ft Floor 7
Luxury Oceanfront Villa with Panoramic Views – 7th Floor at Ko Olina Beach VillasWelcome to paradise! This newly updated 7th floor villa in the Ocean Tower at Ko Olina Beach Villas offers breathtaking panoramic ocean and sunset views, direct beach access, and all the...
Doesn't get better than this! A201
A LITTLE ABOUT THIS CONDO...Lokelani A201 is a 1130 sq. ft., 2 Bedrooms (A/C), 2 Bathrooms (sleeps 4), corner unit. Unobstructed panoramic ocean views, 30 feet from the private sandy beach with surf break. Boogie boarding, paddle boarding, surfing, snorkeling right out...
Maui's Best - Wailea Ekahi 47A
Aloha and mahalo for your interest in our spot in Paradise. Ekahi says it all. This one bedroom (with comfortable sleeper sofa), two-bath renovated unit is on the ground floor. This means the lanai is much larger than upper units. It also means that when you step off...
Kauai Bay House, Ocean Front, AC
Summary:Oceanfront three-level home perched above Kukuiula Bay with sweeping ocean and mountain views. Features two king bedrooms, an open loft with two queen beds, split-system A/C, multiple lanais, a full kitchen, beach gear, and direct access to paddleboarding and...