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.
Beautiful Pili Mai 3E Condo A/C, Across From Pool
Summary:Experience the enchanting allure of Kauai in our 2-story, 3-bedroom, 2.5-bath condominium nestled along the scenic Kiahuna Golf Course in Poipu. Enjoy the breath-taking mountain views that surround this meticulously designed space. Our air-conditioned condo,...
Kamaole Sands 1-307 - Prime Location, Stunning Renovation, Large Lanai, New AC
Kamaole Sands 1-307 is a stunning second home for the new owners. This premium unit features an end unit location with stunning ocean views across the perfectly manicured lawn of Kamaole Sands. Completely remodeled from top to bottom, this one bedroom, two-bathroom...
❤️PiH❤️ Wahi Malu ★ Near Pools ★Fantastic Lani ★ 3 Full Bath ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Wahi Malu, a part of our Hawaiian Luxury Collection. Wahi Malu at KaMilo is a gorgeous 3 bedroom/ 3 bath home.This beautiful home is one of the newest KaMilo homes and is only a short stroll to the pools,...
Stay & Save Plenty this April & May! ~ Spacious, Comfortable & Clean ~ Platinum Maui Vacations
Aloha! Welcome to another exclusive member of the Platinum Maui Vacation Ohana! All villas in our program are given Hawaiian names. This Kapalua Golf Villa is named Hale O Ohana, in Hawaiian translates to: "Home of Family".We include, extras like:~ Secured wifi /...
Gorgeous Beachfront KoOlina Club Resort+Amenities, 2BR
Escape to a world of pure bliss at Marriott's Ko Olina Beach Club, a tropical haven nestled along the breathtaking western shore of Oahu. Imagine being greeted by cascading waterfalls and playful fountains as you step into your very own oasis of luxury and tranquility....
Lovely Private Kailua Cottage
Welcome to our newly renovated 1-bedroom spacious and private cottage that is super centrally located in the heart of Kailua. Our cottage is situated on a beautifully landscaped property which will lead you to a lusciously landscaped garden with outdoor dining & BBQ....
Spectacular Ocean Views
Napili Point, Unit A-5, is located on Maui's western shore. This fully-equipped one-bedroom ground-floor condo offers beautiful views of the Pacific Ocean from the lanai and living room, with the islands of Molokai and Lanai in the distance. Located just a few yards...
Luxury + Privacy • Sleeps 8 • Beach Club Access
Summary:Kulalani in the Mauna Lani Resort • Just across from the pools and gym!Kulalani 503 is a luxurious townhome located in the highly desirable Mauna Lani Resort. Boasting a lavish master suite featuring a spacious tile shower and an indulgent soaking tub. With...
*Maalaea Kai 104* NEW LISTING Maui Stunning Prime Ocean Front !
Enjoy this ground floor unit featuring gorgeous views throughout the unit of Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. The unit is tastefully decorated with the spirit of Aloha and has a portable a/c unit in the living room and...
Stunning Ocean View Beach Front Villa at Kahaluu
Enjoy this resort quality 2 bed 2 bath Penthouse condo with exceptional ocean views across the street from Kona's famous Kahalu'u Beach. Relax in the sand, learn to surf, snorkel with the turtles and tropical fish. All this is just steps away from your door.- Beautiful...
Gorgeous remodeled condo Oceanfront! SUNSET! <br>
Elegance on a budget! This quiet third floor end unit has spectacular ocean views from throughout the condo. Our air-conditioned condo overlooks the beautifully manicured grounds with unobstructed ocean views. The kitchen has concrete countertops and top-end appliances....
Dancing Volcano Estate - sleeps 8 Near Hawaii Volcanoes National Park
Dancing Volcano Estate in Volcano, Hawaii is a fantastic place to stay and visit Hawaii Volcanoes National Park just a few minutes drive from our property. Our main house has 3 bedrooms and 2 bathrooms, full kitchen, large dining area, large living area with SMART TV,...
KAANAPALI COTTAGEn 2 bedroom cottage within walking distance of Kaanapali Beach
International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10...
Ola'a House by Volcano Heritage Cottages in Village center-1 mile to Nat'l Park
Ola'a (meaning "lively" in Hawaiian) House is a 1,700 square foot home in the heart of Volcano Village featuring authentic Hawaiian furnishings and original art by local artists. The house is owned by the co-founder of Kilauea Lodge and former Magnum PI make-up artist...
Pristine 3br Ocean and Mountain View Home in Kukuiula
Tropical elegance with a modern touch and ocean and mountain views are what make Kukuiula Vacation Rental #39 a prime vacation rental. Located in the exclusive Kukuiula community in Poipu, this two-story vacation rental sleeps up to eight people with three bedrooms and...
Just Listed! Top Notch Rental Experience Awaits!
Experience breathtaking sunsets every evening from your private lanai and immerse yourself in the fresh ocean air at Kaleialoha 213. This West Maui vacation condo is perched right on the water's edge, offering unparalleled proximity to the ocean. The property boasts a...
Makaha Ocean Lullaby... The famous Makaha surf beach!
Remodeled fourth floor unit in Makaha's ONLY Beachfront Condo! The other condos you will find are located about 2 miles to the South. Our studio has been completely remodeled, and is located on the cool side of the building, with Ocean and Sandy beach views. We look...
The Crown Jewel of Kawela Bay! 30 day stay
Hale Keo Keo – Historic Beachfront Home on Kawela Bay, Oahu’s North Shore30 day rentals onlyWelcome to Hale Keo Keo, the only home built directly on the sand in Kawela Bay — a calm, crescent-shaped cove on Oahu’s iconic North Shore. With room for up to 17...
ROMANTIC AMBIANCE OF 'OLD HAWAII'. GROUND FLOOR, CLEAN, BEACH GEAR INCLUDED
*About the Property*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...
Newly remodeled 1bd with contemporary finishes
Discover the ultimate island retreat at Kamaole Beach Royale #208—a 1-bedroom, 1-bathroom oasis perfectly situated within walking distance to both the beach and Kihei's vibrant shopping centers. This unit comfortably sleeps up to 4 guests. Renovated in 2022, this...
Ocean front Beach Resort Hale Nalu ~ ~
Aloha ~Step inside and experience the sophisticated charm of a newly renovated space, featuring a state-of-the-art kitchen equipped with modern appliances and sleek finishes, perfect for crafting island-inspired meals. The studio boasts a sumptuous king bed for a...
Spacious lanai-Maui Vista Relax/Work/Play in this lush tropical getaway!
Perfect location! Newly remodeled 1 bedroom/1 bathroom corner unit that sleeps 4. Ideally located with ocean and mountain views. Stay in style with everything you need for work and play. Start your day with a walk on Charley Young beach-literally across the street,...
Posh, beachfront gingerbread home with 3 lanais- walk to parks, dining, tennis
Oceanfront Kalakaua Surf & SunsetsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located directly on spectacular Tonggs Beach, this posh 3BR/2.5BA home looks fresh from the pages of...
Rare, three bedroom Platinum Level remodeled townhouse, featuring the most premier ocean, island and coastal views!
*Please note that the Kapalua Resort and this property were not affected by the Lahaina fires, nor were our surrounding areas or Napili, Kahana and Kā‘anapali. West Maui communities of Kā‘anapali, Nāpili, Honokōwai, and Kapalua are fully open to visitors....
Breathtaking Ocean Views from Quiet Beachfront Condo! Free Parking!
Colony Surf #1005 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)Stunning ocean and Diamond Head views! This spacious (853 sq. ft.) open floor plan suite is the perfect spot to enjoy...
Lani Oasis - Princeville Vacation Home with Saltwater Pool
Welcome to Lani Oasis by Gather, a stunning four-bedroom, three-bathroom home that accommodates up to ten guests in Princeville, HI. Located on Kaua’i’s picturesque north shore, this beautiful home offers lush green cliffs, stunning sunsets, and family-friendly...
Beautifully Renovated with Parking, Steps to Waikiki Beach!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Your oasis by the sea, stay at B103!
Step off your lanai, & enjoy the pristine ocean, pool, or hot tub. Snorkel with sea turtles & colorful fish. Walk to Kaanapali Beach & boardwalk for casual dining or groceries. Additional shops & restaurants minutes away at Whaler's Village & downtown Lahaina. Papakea...
Kauai Dreams - Hanalei Bay Resort 1305/1306
Hanalei Bay Resort 1305 & 6: This beautiful spacious studio with an adjoining hotel room is located on the top floor with high open-beam ceilings. It is surrounded by tropical foliage and spectacular views of Hanalei Bay and Bali Hai. On your very own private lanais,...
❤️PiH❤️OHANA Time ★Closer to KaMilo Pools ★Hilton Resort Passes
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Ohana Time, part of our Hawaiian Luxury Collection.Ohana Time at KaMilo is a wonderful 4-bedroom home in the exclusive Mauna Lani Resort.We take great pride in offering some of the most coveted homes on the...
Regency at Poipu Kai 323: Beautifully Updated Poipu Resort Condo With A/C
** Fall 2025 Special Pricing**Welcome to Regency at Poipu Kai #323, your peaceful Hawaiian home away from home. This south shore Kauai vacation rental condo boasts an ideal location in the heart of sun-drenched Poipu, with easy access to the Garden Island’s best...
REMODELED-OCEAN VIEWS FROM EVERY WINDOW-GREAT BEACH ACCESS-AC-WELL EQUIPPED
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1033 sq. ft) condo that has been completely remodeled with beautiful modern finishes. The condo has ocean views from every window and great beach access as it is right across the street from Kamaole Beach 1....
Golf and Beach Paradise!
Mauna Lani Beach Club pass included! Enjoy beach towels, beach chairs, and toys.PLEASE NOTE: The swimming pool will be closed for Maintenance Mon-Fri from 8:30am-4:30pm Oct 6-27, 2025. Dates may be subject to change due to unforeseen delays.Viking grill on your own...
KM 131 OceanFront Ground Floor Condo w Pool AC Beach
Kauhale Makai 131 Island Style Updated 1Bedroom OceanFront Condo. Ground Floor for Easy Year-Round Indoor-Outdoor Living. Tropical Getaway to Relax and Recharge FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your...
Westin Nanea Ocean Villas, Kaanapali Beach, Gorgeous, 2BdRm Ocean view
Large inviting living room, Gorgeous dining room, breathtaking large Master Bd Rm and ensuite bath with a large modern tub, an attractive second bed room with ensuite bathroom. Gourmet kitchen. One large lanai and a second lanai - great for a meal or drinks anytime!...
Summer Special! 10% Discount With 7 Day Stay
Nestled in the heart of Waikoloa Villas, this top-floor 2 bedroom/2 bath condo offers serene views overlooking the Waikoloa Village golf course. Just a short drive away, you'll find the island's best beaches at Waikoloa Beach Resort, along with a variety of excellent...
Ocean views with Hawaiian-inspired decor
E komo mai! Come on in! Papakea J201 offers the best Papakea has to offer with its quiet shady-side location and broad ocean views. J201 is a 1-bed, 1-bath condo that accommodates 2 guests. The large windows on two sides of the living area offer sweeping views of the...
Island Living: Beachfront Penthouse Retreat at Sugar Beach PH#23
Sugar Beach Resort #PH23 – Island Living in a Penthouse Oceanfront CondoWelcome to Sugar Beach Resort #PH23, a beautifully appointed one-bedroom, one-bathroom penthouse condo with panoramic ocean views. Nestled along Maui’s longest stretch of sandy shoreline, this...
Hapuna Beach Residence B21 at Mauna Kea Resort
This magnificent, oceanfront, newly-constructed, island masterpiece offers floor-to-ceiling window walls that create indoor/outdoor living space, a sleek, gourmet kitchen with Wolf and Sub-Zero appliances, double ovens, a cappuccino machine, wine storage and...
Kona Makai 6303: Tropical Retreat 1BR w/ Ocean Views, Pool & Gym
Perched on the top floor of the beloved Kona Makai community, Kona Makai 6303 is a remodeled 1-bedroom, 1-bathroom oceanfront condo with a bonus loft. Featuring sweeping ocean views, breezy lanai dining, and resort-style amenities, this retreat is perfect for couples or...
Oceanview Maui Condo - Steps from Kamaole Beach!
Escape to paradise at this charming 2-bedroom, 2-bathroom condo in the highly sought-after Maui Kamaole complex in South Kihei. Located just across the street from the beautiful Kamaole Beach III, this second-floor unit offers stunning ocean views, perfect for catching...
Kauai Paradise: oceanview 2-bedroom condo with AC and private lanai
Aloha! Welcome to paradise on the amazing North Shore of Kauai.Our 2 BR/2 BA oceanview condo in Emmalani Court - Princeville, offers a comfortable haven to relax after exploring the Garden Isle. It has wonderful ocean and mountain views and a private lanai, cooled by...
Delightful condo 2-bd condo close to the beach
Island Sands 105 is a 2-bedroom, 2-bathroom ground-floor condo that offers easy access, 1 window A/C in the living room, and a private washer and dryer. This property has elevators for easy access. Unit 105 can accommodate up to 6 guests. The master bedroom offers a...
Fab Ocean View, largest 1 Bedroom Premium Villa!
Ignite your senses with warm, sunny beach days and dazzling sunsets! Ocean View, Beautiful 1 Bedroom, 1 Bath Premium largest size villa at 900 sq ft, sleeps 4. Parking included, no fees.Full Resort Access. On one of the world's most beautiful beaches!The Westin...
🏝Princeville Bliss, Huge Lanai - 3 bedroom, 4 queens, sleeps 10 🐠
Welcome to our large, spacious home in Princeville, Kauai. Perfect for families, couples, or anyone who loves to spread out, this 2000 sq ft 3 bedroom home has been painstakingly remodeled with luxury finishes throughout.Located in a quiet, stunning neighborhood just a...
Koa Resort 5i-updated 3BR, Pool, Tennis, Hot Tub, Zoned AC, Sleeps 9, pool view
Welcome to Koa Resort 5i, located across the street from the beautiful beaches of South Maui. With plenty of room for your entire family, Koa Resort 5i is a great spot to kick back and experience the Maui lifestyle. This is a 3-bedroom 2-bathroom second-story condo,...
Private Pool. Fully Air-conditioned .
This home is new on the rental market. Previously, it was reserved for our family use only. It has been completely refurbished this year. It is the perfect getaway for those that would like their private pool and is located in a peaceful subdivision close to all the...
Fairway Villas Waikoloa A21 Includes Waikoloa Gold King Golf Club Membership
Enjoy our 2 bedroom, 2 bath villa for you and your family quietly tucked away along the Big Island's sunny Kohala Coast, Fairway Villas Waikoloa offers the crisp style, gracious elegance, and modern sophistication. Villa has FREE WIFI and PARKING.VILLA UPDATE - brand...
Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops
Kahala Cottage – A Tranquil Retreat in HonoluluWelcome to Kahala Cottage by Gather, your home-away-from-home in the exclusive Kahala neighborhood on O‘ahu’s south shore. Offered as a monthly rental, this two-bedroom, two-bath island retreat blends laid-back...
An Endless Summer 132- Poipu Beach, Kauai
Located on the most popular beach in Kauai for a reason! Sandy beach and warm ocean water with a large grassy area for lounge chairs for the best sunrise and sunset views! Be as busy or not as you wish..."An Endless Summer" unit 132 is a ground floor end unit taking...