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.
Wailea 1 BR Condo, amazing lanai, close to everything, good pricing
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully this provides some clarity if you have been following this process and were concerned about booking in the next couple of...
Baby Beach Bungalow I - Beautiful Bungalow Steps from Beach
Discover Baby Beach Bungalow I – Your Perfect Kauai RetreatNestled in the highly sought-after Baby Beach neighborhood along Ho'ona Road, Baby Beach Bungalow I offers the perfect blend of comfort and convenience. This charming, single-level cottage features a spacious...
OCEANFRONT CONDO MAUI SUNSET#215-A, SLEEPS 4
MAUI SUNSET IS A FABULOUS OCEAN FRONT PROPERTY. Has a community swimming pool, heated during winter months, hot tub, gym, tennis courts, putting green, barbecue grills.Just STEPS TO THE BEACH allows for WINDSURF, WHALE WATCHING in season, and be on the look out for...
Direct Oceanfront - Intimate, Contemporary Studio Condo
ALOHA and thank you for considering our home for your Maui vacation! Our condo was completely renovated in Dec. 2011 and we hope you like what we've done.Just 10 feet from the ocean and located on the second floor, you will not be disappointed! Upon entering the condo,...
Newly Renovated 1BR w/ King Bed & Great Ocean View
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...
BHTS Kauai Vacation Condo - No Housekeeping Fee
Nestled on a hillside overlooking Kalapaki Bay. Make yourself at home in our 2-bedroom apartment that has a full kitchen, dishwasher, washer & dryer. Banyan Harbor is only 2-miles from the Lihue Airport and centrally located on the Island of Kauai which makes it...
Coastal Ko' Olina Townhome - Walk to Beaches!
Find lush tropical landscapes, top-class resort amenities, and proximity to tons of historical sites at this 2-bedroom, 2-bathroom townhome. This Ko' Olina vacation rental is within walking distance of the crystal clear waters of multiple coves and beaches. Grab the...
Kona’s Best Golf and Beaches
Step through the doors of our beautiful 1,950 SF three bedroom two and half bath townhome and let your Hawaiian experience begin. Located at the picturesque Fairways of Mauna Lani, a tropical paradise situated on 20 acres. This exclusive gated community is set between...
Magnificent Ocean View Penthouse, FREE PARKING-n Pool renovation until 2026
Enjoy being on top of the world and just one block from Waikiki's best beach. Our one bedroom beach house has breath taking panoramic ocean views from front and side windows, a separate fully equipped kitchen, 50" flat screen Smart T.V., large lanai facing the ocean,...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Condo, Recently Updated, Sunsets! HKH-412
Luxurious 2-bedroom Honua Kai villa near the elevator with ocean-view lanai, two master suites, upscale finishes, and panoramic sunset views-perfect for a stylish, relaxing Maui escape!** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an...
2 Bedroom Paradise Getaway on Molokai
Spacious and wonderfully positioned corner unit condo on the third floor that offers privacy, no noise from above and only one wall connecting this unit with others. The main living area and bedroom face the ocean for spectacular views. There are no elevators on Molokai...
The Best of the Best JUST GOT BETTER with 3rd Remodel
Papakea dies not charge So now you save more monet staying at Papakea! Book with no fear the government will cancel your booking and you lose your payment as described below:We are very sorry that the Maui Government is trying to use fear tactics to get the short term...
Amazing Ocean View 2BR 2Bath with Modern AC. Beautifully Upgraded. KKSR 9-305
Aloha! Welcome to Keauhou Kona Surf & Racquet Club #9-305This spectacular top floor, beautifully decorated, highly desirable corner unit has an impressive 1,188 interior square feet, plus a covered wrap around lanai with ocean views. Unit features two bedrooms & two...
HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH
ALOHA & WE WELCOME YOU TO OUR COMFORTABLE HOME AWAY FROM HOME! LOCATED IN THE SUNNY SOUTH SIDE OF THE GARDEN ISLAND OF KAUAI IN POIPU BEACH, THESE 2 HOMES HAVE BEEN RECENTLY CONSTRUCTED WITH TOP OF THE LINE FEATURES, PERFECT FOR A PARADISE FAMILY GATHERING OF MULTIPLE...
Luxury Kolea Villa in Waikoloa Beach Resort-Oceanfront Development
If you are looking for five star accommodations with incredible views, Or you want to own part of paradise this is the spot! Brand new Villa, newly furnished in an upscale gated oceanfront community located across from a private beach club and direct access to Waikoloa...
Oceanfront Getaway on Oahu North Shore
Feel your stress melt away in this gorgeous 3-BR, 2-BA oceanfront sanctuary! House is in a gated community on the fabled Oahu Northshore. The secluded, aqua-blue waters of Kawela Bay are in your own backyard—swim, snorkel, surf, paddleboard, kayak and sunbathe...
Last minute discount, 4/26 - 5/12. Huge 3/3 Oceanfront Penthouse
This beautiful Ocean Tower 10th floor Penthouse end-unit is huge, recently renovated, and has a unique floor plan with glass doors on both sides of the main living area that slide completely into the walls, creating a wide open space more than 75 ft wide with east,...
The Flying Honu is located in the heart of Kona Town
The Flying Honu is located in the heart of Kona three blocks from the Ironman starting line. Built on the fragrant pathway from the mountain to the sea (Mauka to Makai ) it is a great example of Hawaiian single wall construction. Open floor plan with large windows to...
Seaside Zen Cottage - A beach is your front yard
This is an ideal place to relax with family and friends. The lagoon in front of the cottage is a great place for snorkeling, for teaching small children to swim and to rest in the healing waters.Rental of the Cottage can be combined with rental of the "Robertson's Beach...
Oceanfront Paradise! Breathtaking Pacific Views Await at Sugar Beach #319
Welcome to Sugar Beach Resort #319– Your Beachfront ParadiseExperience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with elevators,...
DISCOUNTED RATES! 311 Beautiful oceanfront 2 bed 2 bath 3rd floor condo
Located on the 3rd floor of a small (only 42 units) quiet complex, you will have unlimited views of the beautiful sunsets, turtles feeding and playing in the reefs, right in front of the complex, and whales at play, during their season, on your private lanai. We have...
Maui Resort Rentals: Honua Kai Hokulani 448 - Spacious 2BR w/ Partial Ocean & Mountain Views!
Hokulani 448 is a luxurious two-bedroom suite offering gorgeous views of both the blue Pacific Ocean and the lush West Maui Mountains. Suite 448 affords a perfect opportunity to gather, reconnect, and celebrate. The suite can accommodate up to six guests in two...
BEAUTIFUL OCEANFRONT CONDO
Relax and enjoy this beautifully decorated, spacious top floor apartment with stunning views on three sides. Floor to ceiling sheer curtains and giant slide-open screen doors lead to lanai with perfect ocean views. Open lounge and kitchen with wooden cabinets and...
Gorgeous Oceanview at Kaleialoha 214 Special 175 nightly for Nov- Dec
Amazing ocean views in an oceanfront condo at Kaleialoha. Nicely furnished and updated with a/c in living room and bedroom unlike other units in this complex, fully appointed kitchen and bathroom. Washer/dryer inside the unit for your convenience. Very quiet and private...
❤️PiH❤️ Island Melody Villa ♥ Stunning Views ★ Free Hilton Resort Passes ★ Bikes
Brought to you by Paradise in Hawaii Luxury HomesIsland Melody Villa at The Islands is a spacious 2,600-square-foot home that effortlessly blends luxury, comfort, and thoughtful design.Featuring three beautifully appointed bedrooms, this villa comfortably accommodates...
Imperial Hotel at the Waikiki Beach Walk Penthouse
PLEASE READ THIS IN IT'S ENTIRETY......Hawaii Tax ID #TA-137-632-1536-01 & GE-137-632-1536-01 TMK/Parcel# 260020140286 Address: 205 Lewers St Unit C/12B, Honolulu, HI 96815Located atop the newly remodeled Imperial Hotel at the Waikiki Beach Walk! New salt water rooftop...
Palekaiko Estate - Kailua Kona Luxury Home with Ocean View
Palekaiko, meaning paradise, is our 3200+ sq. ft. home away from home situated on over an acre in a gated community. Palekaiko has three bedrooms, three and a half bathrooms, an office and almost 1000 sq. ft. of outdoor living space. On the property, you will enjoy over...
Waterfront retreat w/ a furnished balcony, incredible view, & a shared pool
Kona Bali Kai #205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Paradise awaits at this two-bedroom, oceanfront, Kailua-Kona condo. Offering a variety of desirable amenities,...
Lehua Lounge in the Heart of Downtown Kona
EVERYTHING IN TOWN AT YOUR FINGERTIPS! Design inspired by my mom’s favorite colors purple and blue and her love for mermaids. Completely renovated home with nice appliances and furniture. 1250 square foot home, 2 Bedroom, 2 Bath, kitchen, top level town house with...
Oceanfront condo with pool, water view, & high-speed WiFi
Mahina Surf 114Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a lovely view of the ocean on your own privately furnished deck, as well as a view of the shared pool! This home...
Best of Mauna Lani! Clean, Spacious Resort Townhome, Pool/Beach Club!
This wonderful townhouse will help you make your Hawaiian vacation dreams come true! Beautifully decorated and well appointed you will find all of the comforts of home in this amazing tropical setting. The luxurious master suite will not disappoint with a king bed,...
At Awapuhi Views, you can check out the surf conditions, and enjoy the breezes
Our home is located halfway down the Miloli'i Rd. We have a very large master bedroom with a King bed, the Master has bow- windows and its own door to the wrap around deck.oceanside deck. The Master bedroom has a walk-in closet, and en suite bath with tub and shower and...
Luxury condo in prestigious Hali'i Kai oceanfront community. Ocean bar and grill
Condo, 2 bedrooms, 2 baths, ( Sleeps 6 )Hali' i Kai is a 30 acre gated oceanfront complex on the Big Island of Hawaii with numerous luxurious resort like amenities. It is about a 20 minute drive from Kailua-Kona airport. Our condo, #23D is a spacious second floor end...
Tropical hideaway with pools, hot tub & grill - the waves await
Maui Kamaole H206Our 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...
Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.n
Aloha. Have you noticed how we're constantly towards the top of Kihei and Maui Vista searches. Well, vrbo has a system of metrics they use that ranks all listings, basically putting the best units available in front of guests...and we're crushing those metrics and have...
Modern, Oceanfront with A/C, discounted for 2025, plus monthly discounts!
Welcome to your Hawaiian Haven on Maui!Please scroll down & read the full description & FAQ's as we have likely already answered your questions below! You can also find out more (and get exclusive discounts) by searching for Hawaiian Haven and the Elikapeka Suite...
Zen Home with AC, Pool, Near Kailua Beach
Inquire about short stays, we accommodate them where possible. Spend your vacation in our Hawaiian style 4 bedroom, 4 bathroom home a 3 minute walk from Kailua Beach. Our home features a balance of indoor and outdoor living. There is a Zen like courtyard and inviting...
Deluxe Ka'anapali Condo with AC Luxurious Retreat
**Kaanapali Plantation #16 – Your Peaceful Island Getaway**Welcome to Kaanapali Plantation #16, your serene island retreat with expansive views of lush landscapes, the Royal Kaanapali Golf Course, and the islands of Lanai and Molokai, all framed by the stunning blue...
3BR Nihilani Condo with AC, Pool & Close to Shops 8C
PROPERTY DESCRIPTIONCome stay in Hale Honu! A luxurious, newly furnished, split-level Nihilani floor plan. Nihilani 8C is in an interior building away from streets and traffic noise and just a short walk to the pool and BBQ area.This unit features hardwoods throughout...
KeALOHA - INCREDIBLE views, Spectacular Beach Park, the Best snorkeling, Turtles
The MAUNA LOA SHORES is right on the ocean in HILO; an exceptional town with plenty to do here on the east side of our beautiful island. The Beach Park next door where you can swim with sea turtles is a once in a life experience. My 45 years as a resident and 42 years...
North Shore Barefoot Hideaway -- come relax with us!
NUC Registration # 1990/NUC-1967TMK # 1570010270146Welcome to our one bedroom, 2 bath condo at Kuilima Estates East. We are an easy 5 minute walk to the beaches by the Turtle Bay Resort. This clean and comfortable condo has a king bed in the master, pull out couch in...
Luxury Private Vacation | 180° Ocean View | AC | Pool | WiFi
Wanting a little getaway? The perfect private oasis awaits you. Imagine the background of the sun setting in the distance drink in hand, and all from your backyard look no further. Upon arrival through the 24 hr guard gated neighborhood, you feel overwhelmed with the...
🏖️Concierge Included | Traditional Hawaiian Home | Steps from Keauhou Bay |vrKCV
vrKCV - Holua Makai, Professionally Managed by Kona Coast VacationsAloha & Welcome to Holua Makai!Nestled in the beautiful Keauhou area, Holua Makai is an expansive, fully renovated island retreat designed for relaxation and convenience. With 3,700 square feet of living...
Villas By The Cove, Villa 3 · Step to White-Sand Beach
Villa 3 at Villas By The Cove is a stand-alone, single story 1 bedroom Villa Suite with ocean views. Its prime location is just steps from two of South Maui's most popular white sand beaches. Newly remodeled, and conveniently located, this 600 sq. ft. 1 bedroom villa...
Maui Kamaole B114 Book with Owner Summer Specials
Maui Kamaole Vacation Condo Rental. WE ARE NOT A MANAGEMENT COMPANY. RENT DIRECTLY FROM THE OWNER AND SAVE!New King size bed, new paint and drapes.Maui Kamaole B114 Vacation Rental is located at the front of the property, close to the main pool, Peek a boo view, and...
AMAZING VIEWS-Kalapaki Cliffside Penthouse-Perched above, elevator to the sand!
Perched high on the Kalapaki cliffs overlooking gorgeous Kalapaki Bay this home serves as the perfect home base to explore the entire island on your unforgettable Kauai vacation. Fall asleep and awake to the relaxing ocean waves nightly at our home perched over the...
Poipu Vibes in Modern Comfort! New Remodel AC- OCEAN VIEW Washer Dryer Rare find
New Remodel in Tropical Paradise..... A/C and Washer Dryer in the unit. This Penthouse unit has a very private setting. Enjoy this beachfront property with Penthouse ocean view.7+ night discount on non peak dates.The lanai will keep you captivated for hours. Watch the...
Prestigious villa with endless ocean views
Kapalua Ridge Villa 2622 is a high-end 1-bedroom, 2-bathroom villa situated on the second level that can accommodate up to 4 guests. Step inside the bright and airy main living area featuring Hawaiian-inspired decor and furnishings with a window air-conditioner and...
"What a Deal, for a unit this nice" (3/30- 4/30) RATE DROPPED to $199 per night ~ FRESH & AFFORDABLE
Welcome to one of the exclusive members of the Platinum Maui Vacations Ohana. We call this Kapalua Golf Villa, Hale O Kauka'i. A Hawaiian phrase which translates to English to 'Home of Sunsets'.Hawaii Tax ID # TA-089-018-4704-02NEW CENTRAL AC, (including new ductwork);...
🏖️Concierge Included | AC | WIFI | Mauna Lani beach access card | vrKCV🏖️
vrKCV - Kulalani at Mauna Lani 802, Professionally Managed by Kona Coast VacationsWelcome to Your Island Retreat in Kulalani at Mauna Lani!Experience the essence of tropical luxury in this professionally decorated and furnished 3-bedroom, 2.5-bath townhome. Perfectly...