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.
Oceanview Serenity Meets Modern Comfort: Discover Wailea Ekolu #402
Wailea Ekolu #402 – Your Serene Wailea EscapeEscape to paradise at Wailea Ekolu #402, where stunning ocean views, serene surroundings, and the spirit of aloha combine to create the ultimate Maui getaway. Nestled above Wailea’s world-famous beaches and golf courses, this...
Charming Home in Mountain View
Newly remodeled home on a two acre property will provide you a real taste of big island living. Peaceful and relaxing environment. Fresh mountain air. Magnificent native foliage. Comfortable cool climate.Explore the island by kayaking in Hilo Bay. Complimentary rental...
koolkondo Ohana House with Pool by the beach
Welcome to koolkondo where you will experience luxury vacation rentals at its finest. Our stylish boutique hotel style condos and homes have it all. You will absolutely enjoy your home away from home with VIP concierge style services in modern island luxury!Aloha and...
Stunning Oceanfront TOP Floor Condo
Aloha and welcome to Kahana Reef #409. With an elevator and stairway right next to the private hallway that leads to our condo it makes it extremely accessible for all. Larger then most condos at the Reef it has 661 square feet. Bedroom is spacious with a Ca king size...
Oceanfront Penthouse, As Close As You Can Stay To Ocean, Stunning Views, A/C!
Banyan Tree Penthouse Condo 402 is a spacious, ocean front condo with an ocean view that will leave you breathless. Located on the quiet 4th floor, penthouse level yet so close to the water that you can actually look down and see tropical fish like the yellow tang! Sea...
Kahala Beachfront Estate – Private Resort-Style Living
For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10 Night Minimum over the Christmas/New Years Holiday Season at $7,500 per night.Spacious beachfront estate is situated on lush tropical grounds, nestled in...
Custom cottage feels bright & airy yet cozy and private in this country setting.
Cottage Cottage feels open and airy with high open beam ceilings in the living room and kitchen. Lots of windows let the trade winds in. Chill upstairs on the catwalk in a comfy recliner or outside on one of the 2 decks or on the relaxing dbl hammock outside. Short Walk...
Aloha Condos, Kanaloa at Kona, Condo 3103, Oceanfront, AC
Kanaloa at Kona Condo 3103 is a wonderful place to stay in Hawaii. Located next to the ocean, it offers stunning views and is fully furnished with everything needed, including a well-equipped kitchen, beach gear, and amenities like pools. Guests praise its cleanliness,...
Hapuna Beach Residence B27 at Mauna Kea Resort
This marvelous, oceanfront, newly-constructed, second level studio offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a luxe chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine storage and...
Emmalani Court 422 - Renovated Princeville Vacation Rental with Pool
Emmalani court is a small, quiet complex in Princeville, near the Princeville Resort. After visiting the 4 main islands in Hawaii, we decided on the North shore for it's lush setting and laid back vibe. There is truly no other place like it in the world. We have been...
Hale Terra 3br 2.5ba Beautiful Nihilani Condo, Central AC, Pool, Hot Tub
Escape to Hale Terra, a modern surf shack nestled in the heart of Princeville. This luxurious, beautifully furnished, 2-story Nihilani townhome offers a tranquil retreat just steps from the pool and BBQ area.Our 3-bedroom, 2.5-bathroom townhome features hardwood floors,...
Spectacular Oceanfront Corner Unit Condo at Kuhio Shores
Closest complex to the water in Poipu, this corner unit in Kuhio Shores is situated on the third floor. Repeat guests come year after year to enjoy our air conditioned oceanfront condo. Whether it's to be lulled to sleep by the sound of the waves, relaxing on the lanai...
Waipouli Beach D-303 2 Heavenly Cal King Beds We Pay Resort Fee's - Best Reviews
This unit is MOUNTAIN VIEW VIEW VIEW!Special* Book Now & We Pay Your Daily Resort Fee's!The Waipouli Beach Resort is a new concept in luxury accommodations on the lush island of Kauai, Hawaii and is centrally located within easy reach to any area of the island. Waipouli...
🏖️Close to Beaches & Restaurants | Spacious Townhome | Concierge Incl
vrKCV - Mauna Lani Village 606, Professionally Managed by Kona Coast VacationsWelcome to Your Slice of Paradise at Mauna Lani VillagesWhether you're planning a family vacation, a couples' retreat, or a relaxing trip with friends, this inviting 3-bedroom, 3.5-bath home...
Modern 3Bed, 2Bath Walking Distance to Beach! AC, 1 Free Parking, and More!
Aloha from Waikiki! Thank you for considering our short-term vacation rental company. We are pleased to offer you Kuhio at Waikiki, a newly remodeled minimalist-style unit in the heart of Waikiki. Our location is just two blocks from the famous Waikiki Beach, providing...
Waikiki Shore 2 Bedroom Condo
Welcome to our 2 bedroom Waikiki Shore Condo. This exclusive Waikiki Shore Condominium is located directly on Waikiki Beach, and is the only privately owned condominium building on Waikiki Beach, and sharing this world famous beach frontage along with some of the finest...
Ocean View Sky Ala Moana Condo w/Amazing Amenities Near Restaurants & Shops
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to The Sky Ala Moana, the newest pinnacle of luxury in Honolulu. This exquisite property, consisting...
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball
Welcome to our Luxury Farmhouse, perfect for large groups or families. Just a half mile from the beach, this property features 5 bedrooms, 4 baths, 2 family rooms, and 1.5 kitchens. Enjoy open shared spaces, private lanais, well-equipped kitchens, spacious baths, A/C...
🤙 APRIL+May Request SPECIAL 🏝️ at the upgraded LIVE ALOHA SUITE
Receive a discount from the listed price by contacting me through VRBO! And YES! Sugar Beach Resort and Maui continue to rank high by the travel periodicals as providing an excellent tropical experience. 📈 THE LIVE ALOHA SUITE is a tastefully designed condo by Stannard...
Calming Coastal Vistas
Summary:Renovated oceanfront 1 bedroom, 1 bath condo with fantastic ocean views. Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy your day at the beach! We strive to achieve a...
Kaanapali Shores Ocean View POST FIRE SAVINGS Unit 203 2BR 2BA
UNIT 203 (Remodeled in 2020) 2-Bedroom, 2-Bath Central Air-Conditioned Unit with a full kitchen, dining area, living room & 2 lanais. The bedrooms and Living Room all have an ocean view. A NEW pull-out sofa that turns into a Queen Bed allows for up to 2 additional...
Special Low Rates-Boutique Ocean Front Living- Cold AC- 5 stars-Romantic
Escape to Paradise at Surf Hale – Luxury Maui Vacation Rental in Kahana. Partake in this stunning luxury oceanfront rental in Maui, perched just 10 feet from the water’s edge on the second floor. Freshly remodeled, this romantic getaway in Kahana offers breathtaking...
Kalapana: 3 BR Luxury Home in West Maui with Pool & Hot Tub
Discover the best in hospitality: Your five-star retreat awaits!Kalapana is truly “Privacy in Paradise” as the home is surrounded by 1.5 acres of lush tropical gardens and fruit trees, in the beautiful neighborhood of Launiupoko, Lahaina. This luxury home is fully...
BEACHFRONT Condo OCEANVIEW -Quiet, SANDY Beach -Snorkeling, Free Parking, Extras
Our "Ocean Blue Paradise" is a BEACHFRONT condo with a beautiful, unobstructed OCEANFRONT view. On a quiet, sandy beach just steps away. Our beach is reef protected, meaning the waves break offshore, so the ones coming onto the beach are usually pretty calm. Making our...
Beautiful Lae Nani - Oceanfront 2 bedroom 2 bath condo with AC
For your comfort, new split air conditioners have been installed in the living room/dining area and both bedrooms. This recently remodeled and updated resort style condo with majestic ocean views is located on the bay on the Coconut Coast of the island of Kauai and is...
Private Oceanfront Top Floor Condo - Kona Reef D34
NEW OWNERS! NEW UPDATES AND IMPROVEMENTS! Welcome to our private and comfortable ocean front condo in paradise - Kona Reef D-34. As soon as you arrive to our very private top floor ocean front condo located on the romantic coastline of the Island of Hawaii you will...
One of Our Best, Now Thru Summer- 6th NIGHT FREE, (Ask Dave How) ~ Platinum Maui Vacations
Welcome to Hale I Ke Kai - which translates in Hawaiian to 'Home Towards The Sea'.From the moment you enter, you will be mesmerized by the breathtaking ocean views from every room of villa 'Hale I Ke Kai'. This impressive villa stands out from the rest with its 180°...
Wailea Grand Champions 159 - 3 Bedroom Golf Course View Condo
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This ground-floor condo offers a spacious layout with three bedrooms and two bathrooms, making it ideal for families or groups...
Pali Ke Kua #242, Stunning Ocean Views!
Pali Ke Kua #242, Princeville Ideally located above the edge of the striking ocean bluffs of Princeville, Pali Ke Kua #242 has all of the features you could want in your island getaway with the benefit of stunning ocean views.The condo community is just the right size...
Kona Bay Oceanfront Home close to Town & Shopping
Watch the Dolphins frolic and the whales in season from your own private lanai where the soft ocean breezes and the gentle waves lapping against the shoreline will relax your mind and body. Newly enclosed private patio with tropical garden is a great place to relax and...
Budget Friendly, ** starting at $ 145.00 Per. night** waterfront complex.
Before you consider booking with someone else in the Kona Isle Complex don’t get gouged and caught overpaying for you holiday, I offer you the best rate in the Kona Isle Complex without additional hidden fees. I welcome you to truly a little piece of Hawaiian Paradise...
Spacious Historic Estate ~ 5 Min Walk to Hilo & Bay Front
Beautifully appointed historic (once King Kamehameha's private lands) 1930s estate in close proximity to beaches, Botanical Gardens, Akaka Falls, and everything HiloTown has to offer! Walk to the Wailuku River & the Hilo Bayfront in only a few minutes from our home....
Close to ocean - 1750 sq ft Home with 4 Bedrooms, 4 Baths
Located in the heart of Hawaiian Paradise Park, the second largest sub-division in the United States, this exquisite vacation rental is only 3 minute drive to the ocean, conveniently located to many tourist attractions and adventure activities. Built in 2019, this...
Haleiwa Waterfront House
LEGALLY LICENSED VACATION RENTALLocation, location, location! This lovely home is perfectly situated on a beautiful white sandy beach, at the end of a quit cull de sac. You will find all the space and privacy that one needs to enjoy a nice peaceful holiday. Historic...
Paniolo Hale's Luxury Offering! ONE of the Best!
The BEST of the BEST at Paniolo Hale. This UPSCALE condo is very tastefully decorated with custom TOMMY BAHAMA furnishings, and has a double lanai to add extra living space. You have to see it, to believe it. This is the largest floor plan for the 2 bedroom, 2 bath...
Remodeled ground floor & easy walk to the beach! 10% is donated to the whales
Aloha and welcome to DG-14! Ground floor and closest unit to the pool and BBQ - no need to wait for an elevator or trek everything through hallways. Largest one bedroom layout within the Kihei Akahi.Steps away from Kamaole II beach, restaurants, the pool and BBQ....
Kepuhi Beach, Molokai, Oceanfront Gem! What a view! Steps to the beach!
This property is on Molokai! Our second-floor condo is a 1 bedroom, plus sleeping loft, 1 bath unit that sleeps 6 and sits yards away from the beach with lovely views of the Pacific Ocean and Kaiaka Rock. It features an updated bathroom, full kitchen, TV, Wi-Fi for cell...
Private and spacious Princeville cottage
The perfect landing for your adventures! Finely appointed cottage with expansive floorplan and private lanai. Walk to the beach for unforgettable sunrises or along the Princeville Path for epic mountain view and ocean bluff sunsets. Walkable to restaurants, shops,...
New Hula House- 3BR great Location Hilo
Welcome to the Hula-House! This home is in a great Location for your Hilo Adventures. We offer a unique 3BR1Bath stand alone Home which is freshly renovated and ready for hosting YOU. You will have 3 Air-Conditioner`s in the Bedrooms plus ceiling fans in every room. We...
🏖️Sunset & Golf Course Views | AC & WIFI | vrKCV
vrKCV - Kanaloa at Keauhou 1501, Professionally Managed by Kona Coast VacationsWelcome to Kanaloa at Keauhou 1501, a beautifully remodeled first-floor unit that offers the perfect blend of comfort, style, and convenience. While there are stairs to navigate upon entry...
Pacific Monarch. 29th Floor with Full Ocean Views. 1 Bedroom. Great Deal!
VIDEO OF CONDO: SEE #3 PHOTOTHIS IS AN '03 UNIT OR A REAL "1 BEDROOM OCEAN VIEW & KITCHEN". THE '02 & '03 UNITS HAVE 1 BEDROOM AND FACE THE OCEAN. THE '01 & '04 UNITS ARE STUDIOS FACING THE CITY. ALL OTHER UNITS ARE MOUNTAIN SIDE.LISTED AS A "1 BEDROOM SUITE WITH A FULL...
Spectacular Views and Prime Location! Oceanfront at Great Rates! Polo Beach 502
Start your day with a stroll along the world-famous beachfront path, which ends right in front of this property. You can enjoy the peaceful, uncrowded beach right out front, or sit poolside at the newly remodeled pool and jacuzzi! After soaking up the sun all day, plan...
Kamaole Beach Royale 405 - Expansive Ocean Views, Spectacular Remodel, Split AC!
Experience the true essence of Aloha in this completely remodeled South Maui hideaway. Kamaole Beach Royale 405 now boasts split AC with thermostatically controlled air handlers in both the bedroom and living room, a brand-new kitchen with stainless steel appliances....
Wailea Ekahi Gem! Remodeled Large 1BR+sleeper, Close to Beach & Pools, XL Lanai
Experience Maui paradise at Wailea Ekahi 21B, a fully renovated ground-floor one-bedroom/two-bath vacation condo nestled within the prestigious Wailea resort district. This beautiful unit showcases a designer remodel, offering a spacious, modern, and bright atmosphere...
Beautiful, Ocean Front Condo With An Ocean View In Sunny Kihei, Maui!
Aloha! Welcome to our beautiful luxurious Maui condo. We invite you to stay and enjoy all that the peaceful and beautiful Kauhale Makai (Village by The Sea) has to offer.We would like to share our vacation home with you! This condo offers; an open concept kitchen,...
❤️PiH❤️MAJESTIC OCEAN★Ocean Views★ Stunning Mauna Kea Resort ★ Best Beaches ★ Bikes
Welcome to Majestic Ocean Villa, a part of our Hawaiian Luxury Collection.Majestic Ocean Villa, located in the prestigious Mauna Kea Resort's Kumulani community, offers sweeping views of the golf course, mountains, and sparkling Pacific. From the moment you wake and...
New Listing! Lovely North Shore Gem in Princeville
Treat yourself to this beautiful North Shore retreat at The Plantation at Princeville. This meticulously maintained and thoughtfully decorated 3-bedroom, 3-bathroom condo offers the perfect blend of Hawaiian charm and modern comfort. Each room features its own en-suite...
Steps Away from Black Sand Beach
Unit 1Our DIRECT OCEANFRONT corner unit (#1) has its own beach only 27 steps away from the lanai (patio). This end unit (no one below you or above you) has added privacy including a quiet grassy area. Experience sunsets year round and let the sound of the waves relax...
Incredibly Large Polynesian Style Villa in Wailea
Spend your vacation in this villa like Polynesian style vacation rental located at the beautiful Palms at Wailea Resort on the Maui's prestigious southern coast. The central air conditioned 1,515 Sq Ft spacious two bedroom, two and a half bath unit is the dream Hawaii...
Maui Resort Rentals: Honua Kai Hokulani 309 - Deluxe 2BR Ocean View in Hokulani's Sought-After "09" Stack, Corner Floor Plan, Massive "L" Shaped Balcony, Gorgeous Ocean Views!
As one of only seven total suites in the Hokulani Tower's legendary "09" column, this suite boasts the closest deluxe 2BR floor plan to the ocean available at the entire resort. Your party will enjoy relaxing views of the Pacific Ocean, the dramatic skyline of Maui's...