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.
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...
Absolutely Beachfront -- Hale Mahina Beach Resort -- B206
Absolutely beachfront, 1 bedroom condo just 20 meters from the ocean. Corner unit on the second floor of a four-story private beachfront complex giving you a spectacular, unobstructed, wrap around ocean view and memorable sunsets. Sleeps 4 with a queen-size bed in the...
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!'Discover the perfect ocean getaway at Islander on the Beach, a 6.5-acre oceanfront resort with stunning...
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,...
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 will be closed for repairs September 2025 through November 2025.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 on the ground floor and...
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...
Marriott Maui Ocean Club- Stunning Three Bedroom Villa Lahaina/Napili Towers
Concierge Realty is proud to present luxury villas at Marriott Maui Ocean Club TowersWe are able to offer 7 night weekly rentals with check-in on Saturdays only.Beginning Aug. 23, 2025, to Dec.16, 2025, Marriott’s Maui Ocean Club - Lahaina & Napili Towers will be...
Breathtaking Panoramic Bali Hai with Unobstructed Bali Hai Ocean View
Named by Condé Nast Traveler as one of the top tropical resorts in the world. This is truly the Hawaii of your dreams.Hanalei Bay Resort is a scenic paradise with awe inspiring views. You'll be surrounded by cascading waterfalls and lush foliage - a mixture of tropical...
"Oceanfront Condo: Coconut Tree & Ocean Views, Whale Watching, Paddlers, and Surfers at Wailua Bay!"
"Picturesque Oceanfront" Wailua Bay View Condo with an Coastline ViewScenic Oceanfront View from this attractive top floor condo at Wailua Bay View. Decorative upgrades with splashes of color with a tropical Hawaiian touch helps you to feel at home. If you are looking...
Wheelchair Accessible Ground Floor 2BR/2BA Makani a Kai
This is a unique property on Maalaea Bay. Recently upgraded and renovated, it boasts wheelchair accessible features such as a large master bathroom, ADA compliant, including a large roll-in shower. Ground floor accessibility and very close accessible parking stalls make...
Elua 2303: Gorgeous Luxe Condo, Ocean Sunset Views
This property is hotel zoned, and not being affected by the recent proposed legislation.This bright and spacious condo is perfect for honeymooning couples, anniversary stays, and those just looking to escape to their own island retreat. Stunning ocean views and lush...
Mauna Kea South Fairways 4 BR -4.5 Bath 180 Ocean Views & Private Pool, Sleeps 8
To see a walkthrough of the house, visit: https://my.matterport.com/show/?m=NffDEzCwbow&brand=0. Situated in the South Fairways of the Mauna Kea Resort, our home has beautiful views of the ocean and mountains, and is the perfect retreat for extended family or friends to...
North Shore Guest House @ Maui Adventure Villa
The North Shore Guest House is conveniently located on Maui's famous North Shore. Spacious, very comfortable, peaceful and quiet THREE (3) BEDROOM/TWO (2 BATHROOM HOME with a large living room and open-style kitchen. A king size bed in the master-bedroom and queen size...
Modern, remodeled, ocean views, comfortable and convenient 580 sf
Hawaii Transient Tax TA-110-236-4672-01Kamaole Beach Royale is located in South Kihei. The building is across the street from Kamaole I Beach Park. This condo building is seven (7) stories and is next to Dolphin Plaza. Solar heated pool is steps away and is in a serene...
OceanView Tranquility: Luxurious Condo with Spectacular Grounds - Elua #1104
Wailea Elua #1104 – Ocean View Comfort with Versatile Sleeping Options and Elegant Island StyleWelcome to Wailea Elua #1104, a beautifully situated ocean view condo offering space, flexibility, and island elegance in one of Maui’s most exclusive beachfront...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 5th floor Ocean AND West Maui Mountain Views
This tandem package is comprised of two fantastic 5th floor two bedroom suites that are right across the hall from each other. Hokulani 510 offers delightful partial ocean views along with views of the West Maui Mountains and Hokulani 511 offers full ocean views along...
Luana Hale: Peaceful Garden Home w/ AC & Serene Lanai in Princeville
Your Princeville paradise awaits in this luxury single-level home in a quiet neighborhood on the lush north shore of Kauai. Tastefully decorated with fine finishes such as travertine tile and Brazilian cherry flooring, Luana Hale offers over 2,800 square feet of stylish...
Quiet @ KOI Ponds! Awesome Garden View J103. Fits Whole Family!
Wake up to koi ponds and tropical gardens just outside your door. This 2BR condo at Papakea Resort puts you 100 yards from the ocean and a short walk to food trucks, coffee shops, and the beach. Spend your days snorkeling, swimming in the resort pools, or playing...
Fantastic Oceanfront Condo at the Cliffs Resort. Great amenities & free WiFi.
Large 1 bedroom / 2 full bath ground-floor condo in Princeville, on Kauai's North Shore at The Cliffs Resort. No need to worry about struggling up stairs with your bags to get to this easily accessible condo. Check out our:1. Queen sized sleeper sofa in living room.2....
Tropical breezes, ocean view and sunny white sand beaches.
Tropical breezes, ocean view and sunny white sand beaches make this an ideal vacation rental house. It is furnished in a traditional island style with a fully equipped kitchen. Upstairs is a large ocean-facing master suite with a California King, an adjoining sun-room...
3 Bedroom Home with a Pool at Waikoloa Beach Resort
Enjoy a 3 bedroom home in Waikoloa Beach Resort at a nice price. This home is situated on one of the larger lots at Ainamalu and offers an open view with both the Mauna Kea and Mauna Loa mountains in the background.The spacious great room offers ample space for...
New Ductless Split A/C System! Close to complex pool and grocery store.
Nestled next to the Kona Country Club Golf Course, this one-bedroom plus den, two-bath condo at the Keauhou Palena complex offers a cozy retreat for your Big Island vacation. Take a quick dip in the pool located just outside, or go for a stroll down the road and enjoy...
Kolea 1A ~ 3 Bedroom Ground Level Kolea Vacation Rental
This ground-level villa offers a prime location with convenient access to a spacious, open grassy area directly off the lanai—ideal for children and anyone looking to enjoy the scenic views in a private, relaxing setting.As you step into the villa, you'll be welcomed...
Tropical ocean front breezes and stunning views
Kahana Reef 321 does not have A/C, is a 1-bedroom, 1-bathroom condo on the 3rd-floor with oceanfront views! Kahana Reef offers an elevator for your convenience. Unit 321 can accommodate up to 4 guests. Fall asleep to the tropical sounds of Maui! In the master bedroom,...
Keoniana Kai - Pool & Hot Tub with Ocean Views
Keoniana Kai, Princeville Perched on a dramatic ocean bluff above the surf, Keoniana Kai, a 3-bedroom (King, Queen, Queen), 4-bath architectural masterpiece, that sits with panoramic ocean and white water surf views.Keoniana Kai, located in the prestigious town of...
All the beauty and tranquility that Kauai has to offer starts with this lovely villa.
Whether you are looking for an adventure-filled visit to Kauai or a peaceful retreat to recharge your senses, this is the place for you! Situated only five miles from Lihue Airport sits this wonderful vacation get-away within the Kauai Beach Villas.This...
This townhouse is a 2 bedroom(s), 2 bathrooms, located in Koloa, HI.
Explore our airy and roomy Royal Palm unit, which is situated in the midst of verdant tropical landscaping and measures 1550 square feet in size. The pure white sands of Poipu Beach are within a five-minute stroll. Luxurious deep tub in the master bathroom, a...
🌴Alii Villas #229 Absolute oceanfront getaway. Nicely upgraded and well equipped🌴
This is one of the most stunning oceanfront condos in Alii Villas. Totally upgraded and set up for your comfort. Sleeps 4 people comfortably in 2 queen beds, walk in showers in both bathrooms, high end appliances and fully equipped kitchen. Free Wifi and flat screen...
Spacious Cliffs Condo with Beach Gear & Ocean View
BEDROOMBedroom: King bed, dresser + closet, connecting bath, lanai w/seating for 2. Room darkening curtains, full length mirrors, mini-fridge, 55” smart TV.Our memory foam mattresses are medium firm with a 1.5" quilted top panel and multiple layers of memory foam,...
The Ishihara Home- Classic Quality!
TVNC-1317 TA-150-219-3664-01Recently refreshed and decorated, this executive style plantation home features fascinating exotic wood finishes with the feeling of home from days past. You will never tire of the expansive jaw dropping Waimea Valley and Ocean Views. Most of...
Hale Kaheka 6596, Oceanfront Private Home and Ohana with a Pool and A/C
Located along the iconic Ali'i Dr., this oceanfront home has privacy and world class amenities. Upon driving into the gate, you will be greeted with unobstructed ocean views. Take a ride down the slide into the pool. Or jump in the spa to relax from a long day of...
Rare Ground Floor Ocean Front, best at Maui Sunset
Ocean front! Ground Floor! B-122 is the closest 2 bedroom to the ocean. Best location and your living area is the 10 acres of manicured lawns and gardens just steps from the large "L" shaped swimming pool of Maui Sunset. Large private condominium apartment at the resort...
Newly renovated Oceanfront Condo! Incredible Sunsets, Endless Views
Hawaii Tax #172-837-0688-01Welcome to Sugar Beach #521. Your Hawaiian paradise -- and your home away from home.Your condo rests peacefully on the 5th floor of one of Maui's best resorts, Sugar Beach. From the spacious lanai (patio), you will gaze upon 4.5 miles of...
Great Deal Ocean View Condo on the North Shore of Kauai!
Welcome to your home away from home in paradise! This two-story condo at Pali Ke Kua offers peaceful garden and ocean views, located in the heart of Princeville on Kauai’s stunning North Shore. Whether you're relaxing by the pool, strolling down the private path to...