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.
Tropical "Jungalow" Near the Sea
Enjoy indoor-outdoor living in our bright, open home... Relax on the lanai overlooking lush vegetation and lava outcrops, smell the fragrant Hawaiian air and listen to the waves crash in the distance. Secluded and quiet--a garden oasis far from the maddening crowd. Open...
Kuhio Shores designer 2br oceanfront condo w/ AC
This beautiful 2 bedroom and 2 bathroom condo has been fully updated and sits directly on the ocean. You will not find a better view and location in Kauai.All beach amenities such as towels, chairs, and boogie boards are provided.3 AC UnitsFully remodeled...
Executive Balinese Vacation Home in Hawaii Kai
Find serenity,luxurious style, at Hale Maluhia. This Oahu vacation rental, whose Hawaiian name translates to "house of tranquility," is a beautifully contemporary resort close to some of the island's best beaches and east oahu coastline. Invite up to eight friends or...
On Golf Course, Cedar Hot Tub, Walk to Beach, Market, Trails! BOHO Modern
Welcome to Paradise – The Luana HouseExperience modern island living at The Luana House, a Boho Modern retreat designed by a local architect and nestled on the scenic Makai Golf Course in Princeville. This newly rebuilt spacious 4-bedroom, 4-bath home features vaulted...
Oceanfront Chic | 2BR Ocean View High Floor
This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to your front-row seat to Maui’s magic.Perched on the 5th floor of a coveted oceanfront resort in Ma'alaea, Island Sands 502 is a fully remodeled and beautifully...
PRIVATE LUXURY HOUSE POOL/ SPA -AIR CON - AMAZING LIFE
LIVE YOUR DREAM IN PARADISE ! 3 LOVELY BEDROOMS - EACH WITH THEIR OWN BEAUTIFUL VIEW... AMAZING PRIVATE POOL - WITH TURTLES ETCHED INTO THE FLOOR BELOW... THE SPA GIVES A GENEROUS MASSAGE AS THE WATER CASCADES INTO THE POOL. STAY FOR A MONTH AND GET A FEEL FOR WHAT...
Gated 2-story beach house with big yard
Hoku Lani, or “Heavenly Star” is a two story air conditioned 3 bedroom, 2.5 bath home with lofty ceilings, concrete construction and gorgeous details throughout. You’ll love the mahogany and kiwi custom cabinetry and granite countertops in our gourmet chef...
Hale Koaniani - 3BR Beachfront Home in Ha'ena
TVNCU#1059 - TA# 121-109-0944-01 - "House with the Cooling Breeze"A true oasis, Hale Koaniani is a meticulously cared for three bedroom, two and a half bath home and a rare find on Kauai's spectacular North Shore. It’s elegantly constructed and furnished and has ocean...
Wailea Ekahi 10C - Close to Main Pool & Beach! Spacious condo -Sleeps Up to Four
Our home is in the 1st (and closest) phase of Ekahi and is just steps away from the main pool pavilion, the beach, and a second pool even closer. Ekahi is a huge complex, so check the complex maps we included before booking. Some units are in another zip code!You have...
4 Mi to Beach: Keaau Retreat w/ Relaxing Porch!
'Ke'ena Ma Puna' | Private Outdoor ShowerA tranquil paradise awaits you and your loved one at this cozy 1-bathroom studio in Keaau, Hawaii! After exploring the nearby Paradise Cliffs or Shipman Beach, rinse off in the outdoor shower and unwind on the front porch while...
Luxury Vacation Rental Napili Gardens | 3 Bedrooms
Summary:Aloha Future Guests,Relax in luxury in this clean, comfortable, and modern Maui home, designed with elegant island-style touches that reflect the beauty of Maui. Just moments from the golden sands of Napili Bay, this serene retreat offers the perfect blend of...
Makai Hideaway 600ft from Ocean Giant Deck/GameroomnAsk about 10 day special
10 day special in September through early December.https://www.youtube.com/watch?v=VigSB3M4z3w The above is the link to a video of my house.Makai Hideaway is quiet and peaceful. Unwind and relax from city life. House is an an hour south of Kona and one hour ten minutes...
🏖️Beautiful Oceanfront | Air-Conditioned | Sleeps 6 | Walk to Beach | vrKCV🏖️
vrKCV - Kona Onenalo #1, Professionally Managed by Kona Coast VacationsEscape to Paradise - Air-Conditioned 3-Bedroom, 3-Bathroom Townhome in an Oceanfront CommunityDiscover the perfect combination of comfort, location, and island beauty at Kona Onenalo 1. This...
Maui Sunset A111, ground floor paradise
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Maui Sunset A111, ground floor paradiseGround floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck...
Kamaole Sands 6-110 3 bed 2 bath Luxury Tropical Oasis split AC W/D
***MAUI PROPOSED VACATION RENTAL BAN WILL NOT GO INTO EFFECT UNTIL 2030 IN THE UNLIKELY EVENT IT PASSES- YOUR BOOKING IS SAFE!! Elevate your Maui experience at highly renowned Kamaole Sands resort condo. Lush, tropical grounds, swaying palm trees, waterfalls and ponds...
Maui Resort Rentals: Westin Kaanapali Ocean Resort North 2BR Oceanfront VIlla
2 Bedroom Oceanfront Luxury Villa at The Westin Ka'anapali Ocean Resort North! This two bedroom, two bathroom luxury villa features over 1200 square foot of interior space and incredible ocean front views of the tranquil blue Pacific Ocean. The fully equipped gourmet...
Designer Condo in Hawaii Kai! Close to beaches, shopping, hiking!
Kick back and relax in this calm, stylish condo located in Hawaii Kai in east Honolulu. This newly redesigned condo is outfitted with brand new, high end furniture to match the allure of the beautiful, newly constructed building and fabulous amenities.This beautiful...
Renovated Penthouse near Beach - sleeps 6!
Beautiful, newly renovated penthouse with big views at the acclaimed Waikoloa Resort. This highly desired loft floor plan is located at the Fairway Villas, an exclusive gated community with elevator access. F34 has high ceilings and a spacious layout for up to six...
Bright and airy garden condo in spectacular Princeville with air conditioning
High ceilings, wide green belts, and privacy in a quiet complex. Located in spectacular Princeville and just a short walk to lovely Anini Beach and the Westin Princeville. The air conditioning system provides nice cool air in both bedrooms and the living area. The home...
Hanalei Bay RESORT 2311, Amazing Views 269.00 May16-20 BlowOutSal 10StarReviews!
NEWLY REMODELED Well maintained Studio!!! One of the best locations on Kauai’s lush North Shore fronting the white sands of Hanalei Bay with amazing views of tropical sunsets, lush green mountains and the sparkling blue waters of the Pacific Ocean. These Kauai condos...
nEye-popping luxury with huge ocean views. Quick walk to Kihei's Best Beaches
Our condo is a totally remodeled townhome with a serene and uninterrupted ocean and mountain view, from the lights of Wailuku Town past the island of Lanai. J217 has neither power lines nor road noise; you'll see sunsets all summer long and whales all winter....
Turtle Paradise - King bed - Maui Vista/steps to beach, free parking, WiFi, AC
Congratulations - You have found your perfect next getaway location. This is an owner-managed unit so no hassle or frustration from third-parties! Attention to detail and personal support are first-class when you stay with us!!Come visit one of the best beaches in all...
KAS 7307 Remodeled Condo w Garden Views AC Walk to Beach
Kamaole Sands 7307 Remodeled 1Bedroom Condo Across the Street from Kamaole III Beach Park at One of the Best Resorts in Maui with Pool, Hot Tubs, Tennis, and More FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your...
Oceanfront, Million-Dollar-View, Newly renovated! B421
THE VIEWS DON'T GET ANY BETTER THAN THIS! True Oceanfront with a panoramic view of the Pacific Ocean, the island of Lana'i, the West Maui Mountains and Maalea Harbor. Spectacular sunsets and swaying palm trees. Great Whale watching (December through April). ** Private...
Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous Kihei
Located in the heart of Kihei, this condo is a dream. With 2 bedrooms featuring two king beds with ceiling fans, Queen size sleeper sofa in Living room, 2 bathrooms with rainfall showers. A chef's kitchen fully stocked with many culinary appliances. It also includes a...
Private Oceanfront w pool, hot tub, sunsets and Turtles
Front row center for Humpback whales (Dec-April) - from the lanai or from our kayaks ! Enjoy our beautiful, tastefully decorated Oceanfront 3 bedroom home (BBKM 2019/0003), accommodating up to 6 adults and 2 additional children. Kihei is the sunniest part of Maui and...
Breathtaking Ocean Views!
This spacious condo is completely renovated with beautiful tile throughout and comfortable island-style furniture. Its soothing atmosphere combined with breathtaking ocean views will be the perfect place for you to relax during your island holiday.Awaken to see the sky...
Tropical Garden Getaway Near Kehena Beach - 2 BR
Prime location for a Paradise Big Island experience! Enjoy peaceful, relaxing nights in Seaview Estates at the Tropical Garden Getaway. This luxurious garden ohana unit on the first floor has a private entrance, deluxe queen bed in one room with morning views of a giant...
Spacious Home Steps from Kamaole 3 Beach
Hosted by VacaMauiWelcome to your perfect Hawaiian getaway at Haleakala Shores! This beautiful condo, located directly across the street from the pristine white sands of Kamaole Beach Park 3, offers an unbeatable location for swimming, snorkeling, and boogie...
Seaside Splendor: Immerse Yourself in Luxury with this Stunning Oceanview Condo!
Oceanview bliss awaits! This condo not only boasts mesmerizing ocean views but also pampers you with luxury amenities. Enjoy a fully-equipped kitchen, spa-like bathroom, high-speed Wi-Fi, and beach equipment. Elevate your vacation - book this seaside sanctuary for the...
Surf, Sand & Serenity- Kihei Akahi D213 Ocean View
Aloha and Welcome to Your Maui Escape at Kihei Akahi D213!We're new owners and offering great prices. Discover your perfect island getaway at our beautifully updated one-bedroom, one-bathroom condo in the heart of South Kihei. Just steps from Kamaole Beach Park II and...
Stunning 3 bedroom beachfront property in Kahana close to all westside beaches
Available April 2026 after renting it for two years to a displaced family of the Lahaina fires. We lost our Premier Host status due to no bookings for two years but we pride ourselves on exceptional hosting at this beautiful property.Kahana offers a stunning beachfront...
"Sea Esta" at Lanikai #121- A Stylish Oceanfront 2nd Floor
Lanikai 121 – Stylish Oceanfront 2-Bedroom Retreat on Kauai's Coconut CoastWelcome to Lanikai 121, a beautiful second-floor oceanfront condo where spectacular sunrises and sweeping Pacific views frame your every moment. This chic and stylish 2-bedroom, 2-bathroom...
Includes Hilton Waikoloa Pool Pass thru 2025. 101 Waikoloa Colony Villas
Waikoloa Colony Villas 101.Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6 person max). Use of the Hilton Waikoloa Pass is...
Newly Renovated Top Floor Luxury Waikoloa Beach Villa F32, Fairway Views!!
Our beautiful gated villa overlooking the Waikoloa Beach Golf Course 3rd and 4th green and the King’s Lake, is our favorite place to vacation and we are confident you will find it the perfect place for your Hawaiian holiday.We are a short walk to Anaeho’omalu Bay...
Beautiful 180 Degree Ocean View With Spa And Pool
Unbelievable views from almost every room in the house!Located just minutes above Kailua-Kona town, this spacious two-story home is a beautiful island getaway for your whole family. Two master bedrooms with king size beds and private bathrooms, two additional bedrooms,...
NEW! "Aloha Kai": Oceanfront at Lae Nani's Newest Renovation + AC + Free Laundry
Welcome to "Aloha Kai" -- the newest-renovated condo in Lae Nani. Here, modern design meets jaw-dropping, unobstructed ocean views. Inside: AC; a fully-equipped kitchen; stone countertops; all-new, comfortable bedding and furniture; and a spa-like standing shower await....
Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!
Ka’ahumanu – Unit 5 – is a top-floor, deluxe oceanfront 2-bedroom/2-bath unit with a king bed in master bedroom, a queen bed in the 2nd bedroom and a queen hide-a-bed in the living room. Beautiful kitchen with porcelain tile floors, granite countertops, bamboo...
OCEAN VIEW CORNER UNIT LIGHT AND BRIGHT, GROUND FLOOR, BEACH GEAR INCLUDED
Welcome to your Maui home away from home! Our family-owned and operated condos have been lovingly cared for by our ohana for over 50 years. We personally live on island and treat each unit with the same attention, care, and aloha we give our own home. Staying here means...
Your own private cottage, 60+ FIVE STAR exceptional reviews!
Hibiscus Hideaway is a licensed Bed and Breakfast, permit # BBKM 2015/0004TA-001-473-5360-01Hawaii Tax I.D. NO W01511848-01This beautiful one bedroom one bathroom cottage is completely brand new and is kept immaculate. Tile floors throughout, granite counter tops in the...
5 Bedroom with Private Pool, Spa, Gym and Putting Green in Waikoloa Beach
Welcome to Aloha Sunrise, your private paradise in Ainamalu at Waikoloa Resort. This luxurious retreat offers seclusion, convenience, and endless relaxation, near Kona's dining and entertainment.Inside, experience elegance and comfort. This lavish getaway accommodates...
Makena Surf F208 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor, this 1,313 square foot residence is designed to provide the ultimate in comfort and relaxation, featuring elegant touches...
★O‘ahu Perfect Vacation • Million Dollar Views, Pool, Near Beach, 4BR Sleeps 14★
Aloha! Welcome to Paradise Mahalo! Nestled in stunning mountains and ocean views, enjoy our modern, luxurious and cozy home located in the majestic Mākaha Valley. Whether it's a few rounds of golf, a hiking trails near by or a five minute drive down to the world famous...
Charming 1bd gem with oceanfront views
Noelani 207 is a 1-bedroom, 1-bathroom condo featuring amenities such as panoramic ocean views, air-conditioning, and a washer/dryer. The condo can accommodate up to 4 guests with a California King-size bed in the bedroom and a queen sleeper sofa in the living room. The...
Ma'alaea Surf, Unit E1-2 BR Ground Floor Beachfront Condo, AC, Wifi, Pool
Ma'alaea Surf, Unit E1 is a deluxe in every sense. E1 is a conveniently located ground floor unit, just steps away from the large pool and ocean. This unit is splendidly furnished and features AC, Wi-Fi, TV, kitchen, 2 outdoor pools, tennis and pickle ball courts,...
Breathtaking Ocean Views! Beach Front Luxury Penthouse, Polo Beach 2 Bed/2 Bath
Indulge in the ultimate Maui experience at this top-floor, direct oceanfront penthouse. Unit 804 boasts a brand-new, high-end luxury remodel and furnishings. There are unparalleled views of the Pacific Ocean and three picturesque islands: Molokini, Lanai, and...
VI 206 OceanFront Studio w Ocean Views Pool
Valley Isle 206 Beautiful Studio at Convenient Location and Close to Amazing Beaches! 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...
Kona White Sands B4 | 0 Bed, 1 Bath
Welcome to Kona White Sands – Your Beachside Retreat on Ali’i DriveNestled across from the iconic Magic Sands Beach, Kona White Sands offers the perfect blend of comfort, convenience, and breathtaking natural beauty. This charming condo provides a flexible layout...
VOK29 Hawaiiana 3br 3ba Villa of Kamalii, AC, Pool
Professional photos coming soon. Located in the resort community of Princeville are the Villas of Kamalii, a gated complex located across from the Makai Golf Club. Enjoy lush garden, mountain and waterfall views from Villa #29, an end unit, split-level townhouse with...
Waipouli Beach Resort & Spa Ocean & Pool Ground Floor in H Building!
Waipouli Beach Resort H104 2 Bdm, 3 Bath – Beautiful Oceanfront and Pool View! King, 2 Double Beds & Queen Sofa SleeperOceanfront! This is one of the most spectacular locations at Waipouli Beach Resort! This beautiful ground-level unit H-104 has spectacular views of...