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.
Two Luxury Homes @ Richardsons Beach Park-Hilo Bay. Sleeps 16. Best Location.
HILO'S BEACHES & SURFRIDER BEACH HOMES:Houses front best swimming, and snorkeling beach on the Big Island of Hawaii. For larger groups we rent both homes together. Please inquire and I'll respond immediately if both homes are available. This listing and price is for...
MV 3202 Remodeled Condo Pool Pickleball AC Across Beach
Maui Vista 3202 Remodeled 1Bedroom Condo in Kihei, Maui, with AC, Pools, Tennis and Pickleball Courts. Across the Street from Sandy Beach for Year-Round Beach Walks and Swimming FREE daily activities included with your stay value up to $554! Complimentary admission,...
Discover Beachfront Paradise: Sugar Beach #121 - Luxury and Serenity Await You!n
SUGAR BEACH RESORT, #121Welcome to Sugar Beach Resort #121, a beautifully remodeled ground-floor condo that combines modern design with the ease of direct beachfront access. Perfectly located in North Kihei, this upgraded one-bedroom, one-bathroom retreat offers...
Dreamy beach condo with balcony, pool, full kitchen & fast WiFi
Mahina Surf 222Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself basking by the shared pool or sipping a favorite cocktail on your private balcony in bliss with the sound...
Oceanview: Walk to Poipu Beach, AC, Private Lanai!
Get away to our luxurious hideaway with killer ocean views, and is 2100 square feet in size, fully air conditioned, and has two bathrooms and three bedrooms. It is equipped with a gourmet kitchen, large TVs in the living area and master bedroom, making it an ideal...
KR604-Spectacular Direct Beachfront Condo on Top Floor - Ocean and Palm Trees
Experience the ultimate beachfront getaway at Kealia 604, a remodeled condo with impressive amenities. This spectacular, top floor unit offers breathtaking panoramic ocean views from the open floor plan featuring a fully equipped kitchen, dining area, and living space....
KS 613 Spacious Kaanapali 2BD Condo Ocean View Pool AC
Kaanapali Shores 613 Spacious Kaanapali Shores 2BD/2BA Family Fun Resort for Everyone KAANAPALI SHORES IS A HOTEL ZONED LEGAL VACATION RENTAL PROPERTYFREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale...
Spacious 2bd plus loft and ocean views
Papakea C405 is a 3-bedroom, 2-bathroom condo located on the top fourth floor, offering fantastic ocean views! The fully equipped and remodeled kitchen is perfect for cooking meals for your group. The kitchen features custom cabinets and lighting, granite countertops...
STUNNING OCEAN & POOL VIEWS in FULLY UPGRADED Condo!
Step into tranquility with this newly remodeled 1-bedroom, 1-bathroom haven, spanning a generous 638 square feet, mere steps from the enchanting Pacific Ocean. Nestled within the conveniently located Kauhale Makai complex, this fully upgraded condo is a testament to...
Pali Ke Kua 245 .. Updated Oceanfront Condo, Views are Expansive!
Location and luxury with a spacious interior (renovated in 2021), high-end furnishing/appliances and large bedrooms/bathrooms.Well-equipped kitchen and additional amenities, including high-speed internet, 80" TV, and air conditioning in the both bedrooms.Located within...
Ko Olina Beach Villas B202: 2BR w/ Gourmet Kitchen, Steps from Pool & Beach
Welcome to Ko Olina Beach Villas B202, a beautifully designed retreat nestled in Kapolei, HI. This vacation condo offers an inviting blend of comfort and elegance, boasting 1,171 square feet of thoughtfully curated living space along with the allure of ocean views.What...
Hale Imaka - 4 Bedroom/3 Bath with Air Conditioning
HALE IMAKA AT KOLOA KAI VACATION RENTALSSpacious Retreat Near Poipu's Best AttractionsWelcome to Hale Imaka, the ideal getaway for families and groups seeking comfort, convenience, and the best of Poipu. This spacious 4-bedroom, 3-bathroom home offers privacy, modern...
Amazing Oceanfront Views!
Amazing Oceanfront views! Simply Stunning. First time offered as a vacation rental since it has been completely remodeled from floor to ceiling! Don`t hesitate to rent this one- you won`t be disappointed! This 2 Bedroom, 2 bath condo has been furnished with a King bed,...
110/Night ...2BR/1BA House in Rural Kamuela
Centrally located to most fabulous Big Island attractions, world renowned beaches, mountain biking, world class golfing, star-gazing with astronomers atop majestic Mauna Kea, halfway to Hilo, the gateway to Volcanoes National Park, this 2 bedroom, 1 bath house with...
Princeville corner unit for 5; Ocean, Sunset, Golf Course Views w/AC & pool.
Pa'ani's corner unit breezy, open feel has a well equipped kitchen for making gourmet meals from the fresh island produce and fish from our farmer's markets and fish markets (Standard Occupancy is 4*/ Max Occupancy is 6*). You'll enjoy the gas grill on the deck while...
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
“Waiohinu” – Unit 204 – is an upper floor 1-bedroom, ocean view unit located in Hana Kai Maui’s Mauka (upper) building. 204 accommodates 1-4 guests with 1 king bed and a queen hide-a-bed. There is a pass-thru window from the kitchen to the lanai with a dining...
🏖️Direct Ocean Front | Sunsets! | Walk to Snorkel Beach | vrKCV
vrKCV - Surf and Racquet 4203, Professionally Managed by Kona Coast VacationsWelcome to Keauhou Surf & Racquet 4203, as known as Kona ʻO ka lā (Sunset), where a true Hawaiian escape awaits. Set against the sound of rolling waves, this serene 2-bedroom sanctuary offers...
MAY the discounts be with you! Spring into summer with these deals on Maui!
TMK #390200010155Hawai'i Tax ID #205-260-2880-01 October is upon us, and that's a great time to beat the fall doldrums with a stay on Maui! And you can do that at our 1-bedroom, 1-bath condo in a genuine paradise-on-earth -- at a special nightly rate! You'll be able to...
Ko Olina's Hillside Villas 1538-2: 3BR, Comfort & Style with Lanai
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 Hillside Villas 1538-2 by Gather, a...
Kiahuna Plantation #215
Aloha and welcome to paradise! We are located on Kauai's beautiful south shore known for it's sunshine and pristine beaches. The Kiahuna plantation sits on 35 tropical acres landscaped with rolling lawns, koi ponds, the renowned Moir gardens, palm trees, and our OWN...
🌴Aloha Moana Penthouse, Top-floor with Ocean Views & Private Elevator 🌴
Enjoy a FREE round of golf at the Waikoloa Beach Golf Resort when you stay 7+ nights! Experience the pinnacle of island luxury at Kolea 13C — a three-bedroom, 3.5-bathpenthouse offering expansive ocean views, curated elegance, and unmatched privacy.Welcome to Kolea,...
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
https://youtube.com/watch?v=F0l15thrQpsIsland architecture offers year round resort-type lifestyle. A Guest House (2 bed/2 bath) with salt water swimming pool (separating it from the main house) can accommodate 4 guests comfortably. All rooms have decks with incredible...
2 Bed/2 Bath Modern & Elegant Oceanfront Vistas
Summary:Spacious and elegant. Completely remodeled recently, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is within...
Pali Ke Kua 114 .. Breathtaking ocean panoramas, Colorful sunrises & sunsets
This delightful, one bedroom condo on the oceanfront overlooks the spectacular North Shore and Hanalei Bay with 180 degree views. Breathtaking ocean panoramas, colorful sunrises, and stunning sunsets with the famed Bali Hai mountain await you, right from the comfort our...
Wailea Luxury on a Budget at Grand Champion Villas - 2 Bd+2 Bath
6th night free! discounts applied when booked. offer good until Dec 15th, 2025.Bldg. 13 - Unit #118 - wonderful upgrades in a comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. Wailea Grand Champions Golf...
Great Oceanfront 3 BR, 3 BATH, Kihei, Maui Condominium with Panoramic Views!
Great oceanfront views! Great sunsets and 180 degree panoramic views from any of the two lanais/ balconies. There is FREE Wifi Access. Recently installed new floors throughout the unit and in the master bedroom. The condo is situated on the second floor of the Maui...
Beautiful grounds close to the beach!
Welcome to our family's 2 bedroom, 2 bathroom ground floor condo! We work hard to make our condo an inviting and relaxing space for you to use as your home base while you explore the amazing island of Maui.Sunny Kihei has earned its nickname - often when there is rain...
Aloha Condos, Kanaloa at Kona, Condo 2601, Oceanfront, AC
This condo is great for couples and families that want to Vacation by the Lovely Oceanfront Pool at Kanaloa: Incredible Pool & Ocean ViewsLarge Oceanfront LanaiSunset Dining• Oceanfront Location• Sunset Views Year Round• Quiet, Residential Location• Walk to...
Gorgeous Remodel! Two King Suites & Huge Ocean Views! Close To Wailea Beaches
Come experience this recently renovated gem located in the highly desired Wailea Ekolu. Expansive panoramic ocean views, natural lighting, gorgeous art, stylish furniture, and a spacious lanai are just a few of the highlights of this beautiful space. This unit has been...
Great Ocean View At The Ilikai Hotel! A++++ One-Bedroom Fully Re-Modeled Unit
Look no further, you've found PARADISE! This condo is located on the 15th floor of the Ilikai Hotel. Enjoy the your morning coffee while enjoying the views of the lagoon & Pacific Ocean. End your week with Friday night fireworks off the lagoon from your private lanai....
🏖️Almost Ocean Front | Beautiful Woodwork | Top Floor | vrKCV
vrKCV - Casa de Emdeko 318, Professionally Managed by Kona Coast VacationsCasa De Emdeko 318 – Spacious One-Bedroom Condo with Ocean ViewsExperience breathtaking ocean views and year-round stunning sunsets from the spacious lanai of this beautifully appointed...
Westin Ka’anapali Resort, Full Kitchen, Access to Resort Amenities
Come enjoy this comfortable two-bedroom Lock-Off south villa which offers plenty of space. This Lock-Off combines a one-bedroom premium villa which features a king-size Westin Heavenly bed in the main bedroom, living area with sofa bed, Armoire in living area equipped...
Oceanfront Corner Condo near Lawai Beach w/Balcony, Free WiFi, Shared W/D, Grill
Kuhio Shores 201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to a peaceful tropical vacation at this Kuhio Shores condo just steps from Lawai Beach, a local...
Steps from the beach, Sunset from your balcony!
A favorite condo by seasoned Maui visitors, this 1 bedroom. 1 bath unit is charming and comfortable with many extras. Shores of Maui 113 is just steps from the pool and hot tub. Imagine cooking dinner at the BBQs while watching the ocean or sitting around the table by...
Tutu's Getaway Owned and Operated by Local Kauai Resident
Nihilani Townhouse unit 19 A is located in the resort community of Princeville. This plantation style townhome complex completed in 2006 makes it one of the newest developments within the Princeville Resort community. Spacious and beautifully decorated, 3 bedrooms and 2...
Aloha Kai-Ocean View Condo | 1 Bed, 1 Bath
This little piece of Maui paradise will make you feel like you are in a home-away-from home! You'll love the amazing ocean view and private lanai where you can enjoy sipping your morning coffee or tea and marvel at the sunsets as you enjoy a cocktail and "pu-pu's".Our...
Top-floor beach corner unit - sweeping views - steps to oceanside pool & hot tub
Islander on the Beach 339Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Promotional Rate for October and November 2025 is $119 a night.Discover the perfect ocean getaway at...
Hilton Hawaiian Village Lagoon Tower, pristine beachfront resort, private lagoon
Please choose a Friday, Saturday, or Sunday check-in and enjoy a seven night stay.Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.Need a...
Hidden Gem Next to Sugar Beach in North Kihei
Aloha. This gorgeous one-bedroom condo is truly a hidden gem. Walk across the street for a sunset stroll or a morning walk on a 4-mile stretch of Sugar Beach, the longest beach on Maui. This well-appointed condo, pristine gardens and beautiful pool provide you with all...
Ko Olina Beach Villas B204: Serene Ocean Views from Lanai
Discover the renewed charm of Ko Olina Beach Villas B204 by Gather, a stunning three-bedroom, three-bathroom villa on the second floor. Accommodating up to eight guests, this vacation rental blends luxury and tranquility, offering the perfect island retreat within the...
Condo w/ Private Lanai, Ocean View & On-Site Pool!
Trade those snow-capped mountains for sunny, sandy beaches and stay at this 1-bedroom, 1-bathroom vacation rental condo! Spend your mornings surfing on the waves of Cove Park Bay, your afternoons exploring the local town, and your evenings inside the cozy condo,...
Heart of Waikiki! Modern 2 bedrooms/1 bath, short walk to the beach!
Regency on Beachwalk #56 – 255 Beach WalkYou'll appreciate the comfort and convenience of this modern, fully-furnished two-bedroom, one-bath corner condo (fully renovated in 2024, 693 sqft plus two lanais with tables and chairs, for a total of 910 sqft) at the Regency...
Luxury escape with AC, pools & hot tub - close to beaches
Maui Kamaole J118Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Oceanfront Penthouse at Maalaea in South Maui
Immerse yourself in the splendor of direct oceanfront living at this charming fourth-floor condo, offering unparalleled panoramic views of the Pacific. Start your day by savoring your morning coffee while turtles gracefully swim below and whales breach during their...
Lush Garden Island Condo | Pono Kai Resort | PK-F105
Pono Kai's pool and spa will be closed January 6-31, 2026 for the instillation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Lush Ocean View Condo is a 1 bedroom, 1 bathroom ocean view condo located...
Contemporary City View One Bedroom Condo at the Ilikai w/King Bed & AC!
Experience the beauty of Waikiki with Happy Vacations! Our team is excited to offer you a contemporary condo at the Ilikai. You'll love the spacious balcony, thoughtfully furnished with attention to detail, providing an ideal spot to sip your morning coffee and take in...
Bright, open-concept living area with ocean view
Papakea B306 is a bright 1-bedroom, 1-bathroom condo with a stunning ocean view, featuring amenities such as a washer/dryer, and air-conditioning! The condo was remodeled in 2021 and 2024 and can accommodate up to 3 guests with a King-size bed in the bedroom and a...
Sunset Oasis in Paradise
Wake up to songbirds every morning, enjoy breakfast on the lanai and watch the day unfold. End the day on the lounger as the sun sets right before your eyes after exploring the island. Our home in paradise offers:o Step through the front door and be greeted by...
Majestic North Shore "Cliffs" Condo
Princeville is one of the most majestic places in the world and our spacious condo allows you to take in the views of both the ocean and the mountains.Corner unit, tons of natural light, 2 lanais (off bedroom and living room) offering gorgeous views and cooling ocean...