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.
Breathtaking View on Beautiful Sandy Beach Oceanfront
This Oceanfront Condo has an amazing view. It has a gorgeous Great Room and a beautiful fully equipped kitchen. With the roar of the ocean just a few yards away, you will not want to leave the Lanai after relaxing on the Tropitone furniture.This Condo has a beautiful...
The Islands at Mauna Lani | F4
The Islands at Mauna Lani F4 has everything you could want in a vacation rental for a memorable stay on the Island of Hawaii. This ground floor two-bedroom condo that sleeps up to six guests is 2,189 square feet and enjoys peaceful vistas across a beautiful golf course...
Luxurious Ground Floor, Perfect Family Spot, Private Lanai, 1 Min to Pool/Beach
Hokulani 142, Honau Kai Resort, is a fabulous ground floor unit with a beautiful private lanai and garden area. Our lanai extends out to an open grass area which many of our guests use to relax, play games, or enjoy the quiet surroundings. There are no elevators exiting...
Hale Makani Nui: Sea-View Hilltop Villa Near Beaches
This lovely hilltop villa—Hale Makani Nui, or House of Strong Wind—is delightfully elevated, in every sense of the word. Its picturesque placement at the crown of a gently sloping lot gives an enchanting estate-like feel to the entire property, while also providing...
Ocean Views from Private Lanai 1 bed/1 bath Cottage on a 100% organic Farm!
Kona Mauna Kai is a working farm on the slopes of Mauna Loa on the Big Island of Hawaii. Mauna Kai means mountain and ocean and that’s exactly what you get on our farm. 180 degree views of the beautiful Kona coastline.On the farm, we grow avocado, macadamia nuts, and...
Includes Beach Gear! Spacious lanai with resort views. #2 Shores at Waikoloa
This vacation rental is professionally managed by ResorticaHawaiiShores at Waikoloa Villa 2Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: 2 Queen BedsAmenities:Beach Equipment: All of our vacation rentals...
Whaler on Kaanapali Beach Oceanfrnt 2 Bdrm April openings! Whales Whales Whales!
Breathtaking views of Black Rock, Molokai, and Lanai - Whaler 552 is a beautiful 2 bedroom, 2 bathroom suite located oceanfront at The Whaler on Kaanapali Beach. Enjoy year-round sunset views and seasonal humpback whale watching right from your own lanai! Just steps...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Stunning 3rd Floor Ocean Views!
This unique offering combines two neighboring 3rd-floor two-bedroom suites to create an exceptional 4-bedroom package that is perfect for large families or groups. Located only one stack back from oceanfront, Konea 303 provides stunning views of the blue Pacific Ocean...
Hui Pu: Beachfront Home at Waialea Bay with AC & Ocean View
Welcome to Hui Pu by Gather, a luxurious beachfront compound situated on the pristine shores of Waialea Bay on the Big Island of Hawaii. This A-frame Tahitian-style estate has been meticulously renovated to offer modern luxury while preserving its timeless charm. With 4...
Resort getaway with views of Hanalei Bay, pools & tennis
Hanalei Bay Resort 4204/5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 4204/5 is an air-conditioned condo, featuring two bedrooms, two bathrooms, kitchen, living...
Secluded home with spectacular ocean and sunset views
Kihei's Hidden Gem (B&B permit #BBKM20210002)offers an ideal setting for your family or group to experience a memorable Hawaiian getaway. This brand new south Maui vacation rental boasts ocean, mountain, and sunset views, a private pool, central air conditioning, and a...
It's Special - This Award Winning Designer Masterpiece is Phenomenal!
Kauai Haven is nestled within a classic Hawaiian style backdrop, resting on the edge of a bluff overlooking the spectacular Pacific Ocean. An award-winning designer, who is part of the Coastal Living Network of designers, has designed this exquisite condo that offers...
New Listing Perfect Ocean Front Location 2BR Kaha Lani 223.
The Location:Perfectly positioned to accommodate everyone's interests, the Coconut Coast is flanked by epic coastline threaded together by the Ke Ala Hele Makale coastal bike and walking path. Just a 7-minute walk along the path or the golden sand beach brings you to...
Ocean View. Hilton Waikoloa Pass for 2025. B305 Vista Waikoloa
Vista Waikoloa B305. Ocean Views!This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationHilton Pool Pass: Valid for stays through December 31, 2025. Maximum 6 persons per pass (children under the age of 5 are not...
Beautiful Condo in Kihei Alii Kai, steps from Kam 1 beach
Welcome to our bright and beautiful condo, ideally situated near the front of the complex—just steps away from the beach! Thoughtfully upgraded with new furniture in Summer 2022, this is the only condo we own, and we’ve equipped it with all the comforts needed for...
Stunningly Renovated! Ocean View! Elua 2305
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to Elua 2305. Your ultimate Maui vacation awaits at this fabulous listing! Don’t miss this incredible opportunity to enjoy the very best that Maui has to offer.Say Aloha to...
Maui Resort Rentals: The Whaler 1061 - Upgraded 10th Floor Studio w/ Stunning Pacific Ocean and Mountain Views!
Perched high above the palm fronds, guests are treated to unobstructed views of the tranquil blue Pacific and the soft sands of world-renowned Kaanapali Beach from this luxurious 10th-floor studio suite. Fold away the floor-to-ceiling glass doors and step out onto your...
Wailea Ekolu Village | 706
Towering oleander and bougainvillea grace the front entry of Wailea Ekolu 706. Enjoy views out over the tropical grounds and beyond from the elevated second floor positioning of this condo. During the winter months, you can whale watch right from the lanai as you gaze...
Molokai Shores Resort Condo
Set sail to Molokai and book an unforgettable stay at this Kaunakakai vacation rental. The 1-bedroom, 1-bathroom tropical condo, located in the Molokai Shores Resort community, boasts access to the year-round outdoor pool, shuffleboard, picnic areas, and 4 acres of...
Summer sale! Fairways at Mauna Lani: Deluxe Island Getaway
10% discount for bookings 7 nights or more.The deluxe 2 bedroom town home will delight you and the island of Hawaii will not disappoint. Golf course view, private patio, 2 coaster bikes, resort pool and on-site gym. Enjoy the beautiful walking/running trails and the...
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
The Makani suite is named after the wonderful trade winds we receive here on Maui! Enjoy the breeze in the front lanai rocking chairs while sipping your cup of coffee. Though this is our economy suite it is spacious and has all the comforts and amenities. Designed in a...
"The Happy Seal" Oceanfront House, watch seals sunbath from our deck while BBQ
[A legal rental of minimum 30 days]This is the story of a little beach house doing its part in preserving a sanctuary on this stretch of sand for the endangered Hawaiian monk seals. For many years the beach in front of the house was known as the home of a famously...
Pure comfort in Paradise!
Location is everything with this property. Not only is the beach right across the street, you are also a short walking distance from restaurants and shops of every kind. This unit is away from the street completely remodeled from top to bottom in 2020 and on the second...
MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!
Modern Luxury at Kapalua Golf Villas – Your Ultimate Maui RetreatWelcome to Modern Hawaii at Kapalua Golf Villas, a rare three-bedroom, three-bathroom retreat offering over 2,000 sq. ft. of beautifully remodeled living space. Nestled in the front row of the...
Pili Mai Family Condo 5C, 3 Bedroom 3 Bath, Mountain View, Cool Lanai,
Three bedrooms, 1 King bed, 1 Queen bed and 2 Twin beds plus a sleeper sofa, 3 full bathrooms, upgrades throughout, washer and dryer in unit, single car garage, spacious lanai space perfect for family and friends! Your dream vacation is waiting at this 3 bedroom, 3 bath...
Aloha Waikiki Condo 2Beds, 2Baths, Free Parking.
Aloha, thanks for checking in our listing. A Newly remodeled penthouse 2 bedrooms and 2 full baths. There are 4 queen beds and 1 single beds, full kitchen with kitchenette. It's spacious 1,000 sq. ft. with 2 patio and 3 Air-Con. It’s on 17 top floor with beautiful...
Hale Nana Kohola – Puako Oceanfront Vacation Home
Hale Nana Kohola (Whale Watch House) Located in the heart of Puako, offers a tropical retreat that showcases the best of Hawaii and is perfect for a romantic getaway or a family vacation. Escape to the sunny Kohala Coast on the Island of Hawaii. Hawaii's perfect...
Maui's BEST AC Beachfront – Panoramic Ocean Views! No Cleaning/ Parking Fees
Free Parking | Free WiFi | No Resort FeesWelcome to your dream Maui getaway! Our stunning beachfront corner unit condo on Kahana Beach offers breathtaking panoramic ocean views with floor-to-ceiling windows and doors, filling your space with endless blue horizons. Relax...
ICC 41 Remodeled 3BD Kaanapali Cottage w Heated Pool
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Hale Leimomi: Luxurious Comfort + Pool + Views!
In this sparkling new villa, laid-back comfort harmonizes—beautifully—with the ultimate in luxurious appointments & upscale amenities. Extraordinarily spacious, with 3,902 square feet under roof, Hale Leimomi combines the elegance of a 4-star resort hotel with the...
Spacious 2bedroom/2bath Beach Front Condo
Royal Kahana end unit condo 620 offers what need to make lasting memories in comfort and private. The master bedroom includes King size bed, with private master bath and its own private access to the lanai. The second bedroom has 2 Full size beds. The condo is central...
Halehikiola: 3 BR, 2 BA House in Volcano, Sleeps 10
Aloha, we invite you to stay at our “house of new dawns.”Halehikiola was named for the refreshing way it evokes the Hawaiian value of Ka la hiki ola each morning as the house fills with light. As “the dawning of a new day,” Ka la hiki ola is the value of...
One Bedroom Oceanview Deluxe Luana Kai A202
Aloha!Welcome to Luana Kai Resort Unit A202. As you walk into the unit you are drawn to the direct unobstructed panoramic views of the ocean where the beach is just a very short walk away, across from the greenbelt of the Waipuilani Park without having to cross any...
Beautiful Pili Mai Condo-2 Bdrm + sleeping den, sleeps 6, with A/C
Relax and enjoy modern living at Kauai’s newest townhome community, Pili Mai! This condo, also known as Nani Ka Hale, is located on the second and third floor of the building. It overlooks the lush greens of Kiahuna Golf Course and offers stunning distant ocean views...
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
**Looking for other accommodations, please view my other unit located in the same building #2773517**This unit is located on a high floor of the Aston Waikiki Sunset Hotel, this condo offers one bedroom (one king size bed), one bath, expansive living area (queen sofa...
This modern Princeville gem shines in comfort, luxury, and design
This modern Princeville gem shines in comfort, luxury, and design. Artfully remodeled and curated by published designer, special features include a stylish sunken living room and open concept living area with twenty-foot beamed ceilings. Relax inside with AC and ceiling...
Kihei Akahi D614 -Top Floor/Panoramic view-Hotel zone- Full A/C Owner managed
Kihei Akahi D 614 is a top floor condo across from Kamaole II Beach Park with views of the ocean and outer islands of Molokini, Kahoolawe, and Lanai, renovated and fully stocked with everything you could need for a complete tropical vacation. ELECTRONIC KEYLESS ENTRY...
Relax in this OceanView Estate w/ Lava stone-lined Infinity Pool & Private Spa
The Hualalai Resort will host the annual Chairman’s Club event from December 1–6, 2025. Please note that access to certain resort amenities may be limited or restricted during this time for residential rental guests. We recommend inquiring prior to booking if your...
Hale Kai - Large Enclosed Lanai - Sleeps 2
Hale Kai - Spacious Enclosed Lanai - Sleeps 2Welcome to Hale Kai, your “Home by the Sea” in the charming Kuilima Estates East community. This beautifully designed island-style retreat offers 875 square feet of living space, including a large enclosed lanai, perfect...
Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011
Pineapple Cottage enjoys a 5-star rating. Enjoy peace and quiet overlooking a private gulch and stream with a bit of with ocean view. Pineapple Cottage offers hardwood floors, shaker cabinets, granite countertops, newly purchased leather sofa, and a covered lanai with a...
Mahina Cottage, Mahina Cottage
Mahina Cottage is a charming and romantic Thai-inspired guest house. It is perfectly set up for a truly rejuvenating stay or intimate retreat.This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a large bamboo-rail deck which looks out onto...
Spacious 2BR Best Ocean Views -Kapalua Golf Villas 11P 5-6
This is a legally permitted vacation rental according to the County of Maui ordinances.Oceanfront Bliss & Golf Course Serenity – Kapalua's Premier Escape AwaitsE komo mai (welcome) to the Hawaiian escape of your dreams, where every sunrise whispers serenity and every...
Tropical style Luxury Townhome, newly renovated - Paradise!
Located in Princeville on the island of Kauai, this beautifully fully redone property will have everything you will need for your vacation in one of the most beautiful places.The master bedroom features a king bed, television and an en suite bathroom. The second bedroom...
☼ Stylish & Bright 2bd Oceanfront Condo｜5★ Views
Step into the comfort of this stylish 2BR, 1Bath condo in the heart of Maui, Hawaii. Located right on the oceanfront, just steps from the beach, this is your perfect retreat close to top restaurants, attractions, and stunning beaches!Enjoy modern design, breathtaking...
Waikīkī Beach Loft Near Restaurants
Stay close to Waikīkī Beach, minutes to Fort DeRussy Beach Park. Our 2-bedroom designer loft is in a secure building with a free offsite parking pass. Highlights include a full kitchen, unique wet room, beach gear, kids accessories and onsite laundry room. Find an ABC...
Largest Ocean Villa at Turtle Bay! Fully Renovated 4BR w/ beach, pool & hot tub
The Ocean Villas are located at the heart of Oahu’s fabled North Shore, nestled within the grounds of the world-famous Turtle Bay Resort. Locals call this ‘country’ for its exquisite beaches, surf heavens, and relative lack of tourists — yet the metropolis of...
Waikiki Ocean View with AC, Full Kitchen, Washer/Dryer, FREE Parking & Wi-Fi!
Waikiki Skytower #2604 – 2410 Cleghorn St.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! Enjoy magnificent Pacific Ocean views from this contemporary, updated high-floor, one-bedroom condo (585 sqft plus private 90-sqft...
Kailani #315, Top Floor, Walk to Kapaa Town and Beach, AC
Kauai Kailani #315, Kapaa, Hawaii. Kauai vacation rental conveniently located in Kapaa Town on Kauai’s Royal Coconut Coast. This cute boutique condo is walking distance to the ocean, shops, restaurants, coffee shops and more! No Resort Fees.Newly remodeled Unit! Two...
Ground floor just steps away from sandy beaches
Hono Kai A4 is a ground-floor, 1-bedroom, 1-bathroom condo that offers a portable A/C in the bedroom and ceiling fans throughout, which helps to keep you cool. Unit A4 can accommodate up to 4 guests. The bedroom presents a queen-size bed, while a queen-size sofa sleeper...
Maui Resort Rentals: Honua Kai Hokulani 112 – Super Quiet and Private Ground Floor 2BR, Easy Access to Pools, Beach, and BBQs, Large Lawn Area!
Boasting a convenient ground-floor location, Hokulani 112 features numerous upgrades throughout and offers partial ocean views from the large adjacent lawn area. Enjoy easy and convenient resort access with the pools, beach, gourmet market, and BBQs just steps away.The...