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.
Hale Ohe - Best Value Beachfront Home Steps from Beach
The Hale O’he (Bamboo House) is twenty feet from an intimate white sand beach. All levels have lanais which invite you to relax and enjoy our beautiful Hawaiian sunsets. The kitchen and dining areas are open and spacious. The home sleeps six and has two bedrooms and...
Marriott Maui Ocean Club- Stunning One Bedroom Villa Lahaina/Napili Towers
Concierge Realty is proud to present luxury villas at Marriott Maui Ocean Club Towers.**Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only.Beginning Aug. 23, 2025, to Dec.16, 2025, Marriott’s...
Hale Pakika at Kukui'ula: Exclusive 5BR Estate with Private Pool, Golf & Ocean Vistas
Welcome to Hale Pakika at Kukui’ula by Gather, a luxurious 5-bedroom, 5.5-bathroom Koloa hideaway, perfect for up to 12 guests. Boasting ocean views and an exclusive location off the first tee of Kukuiula Golf Course, this home offers a serene escape on Kauai’s...
Steps to the Ocean, Puako "Dream House"
A wonderful relaxing get away to the magical, historic Puako on the Big Island. The rate covers 6 guests. The "Dream House" is located in the enchanting beach community of Puako on the Big Island of Hawaii, just north of the Mauna Lani resort and south of the Mauna Kea,...
Escape to paradise at Waikoloa Fairways' 2-bed, 2.5-bath condo + stunning views
Experience the ultimate in vacation comfort with our exclusive benefits. Enjoy complimentary late check-out (subject to availability) to maximize your stay. Book a 7-night stay and receive your 8th night completely free – perfect for an extended escape. Plus, as a...
Luxurious Oceanview Home w/Pool, AC & BBQ Lanai: Blue Hawaii
Blue Hawaii is a thirty two hundred square ft. property providing a great experience for family and friends. This expansive well-appointed home is perfect for a large group. Because of the size of this property, you have the space to entertain both inside and out. The...
4 bed/4 bath Entire custom-built house 5 mins from Volcanoes National Park
Enjoy peaceful Big Island Hawaii in a Contemporary Hawaiian Craftsman Cottage style home set in a Tropical Rainforest directly outside Hawai’i Volcanoes National Park. The custom designed & built home features artisan beds with fine linens, private baths, cozy...
Awesome Oceanfront Condo, Great Views, Steps to the Beach, KR#207
Enjoy the gorgeous ocean views while sitting on the lanai and soaking in the beauty all around. This condo sits right on Sugar Beach, with 6 miles of white sand beach right in front of our condo. Great for beach walks, playing in the ocean, or enjoy the shade trees in...
Hali'i Kai Resort - 8D Luxury 2-Bedroom Ocean View Villa
Summary:One of best views at Hali'i Kai! Recently re-painted with a fresh and bright interior! Hali’I Kai 8D is a premiere 2-bedroom ocean view villa in the private Hali'i Kai community. This recently added property, located on the sun-drenched shores of the Waikoloa...
KBM Resorts | FREE CAR | Hale Makai At Montage Kapalua Bay 3-Bedroom Beachfront Condo with Daily Housekeeping, Spa!
Elegant 3BR oceanfront villa at Montage Kapalua Bay with panoramic views, high-end finishes, private lanai, and resort amenities. Ideal for families or groups seeking a luxurious Maui escape.*Special Offer- Book any KBM rental home in Hawaii for 6 nights or more with an...
Please contact me for specific dates that you may be interested in.
This is your home away from home in an immaculate, spaciously designed guest house built for relaxing in comfort, style & convenience. This an attached 2 bedroom + 2 bath fully-equipped house + sofa bed and a very large stocked kitchen with a separate entrance and foyer...
Peaceful Volcano Home Near National Park!
A tropical paradise awaits when you book a stay at this 2-bedroom, 2-bathroom Volcano vacation rental! Located on the historic Volcano Golf Course, this home provides a fully equipped kitchen, a deck with a golf course, spectacular stargazing and Mauna Loa sunset views,...
Hale Kuilima: Condo on the Golf Course at Turtle Bay
Our bright and breezy Kuilima West condo is located steps away from Turtle Bay Resort, Lei Lei's restaurant, walking trails, golf, and the beautiful beaches of Oahu's North Shore. With two Tempur-Pedic king beds and AC in all bedrooms and the living room, you can enjoy...
Hokulani Villa: Pristine Tropical Getaway w/Ocean & Fairway Views, Pool & AC
Unwind in welcoming luxury at Hokulani Villa by Gather, a serene retreat with a private pool and stunning views of the Makai Golf Course, Bali Hai, and a peek of the ocean. This beautifully furnished home is designed for relaxation, with split air conditioning systems...
Perch - Maui Sunset: One Bedroom Suite, Part Ocean View with Big Lanai
Island Vacation at its finest! This partial ocean view condo is designed for comfort. Partial Ocean view, the unit has been nicely designed and features tile flooring, granite kitchen counters, stainless steel appliances and more. A large lanai Ideal for taking in that...
Island Cottage A/C-Pool-BBQ
Aloha! We welcome you to our beautifully decorated and loved island home. Located in the heart of Princeville and centrally located to stunning beaches, restaurants, retail, and more. This is the perfect place to recharge and relax after a day of island adventure. You...
One of the Most Beautiful Ocean Views in West Maui at Kaleialoha
Gorgeously and recently renovated unit at Kaliealoha tucked in the corner to avail of the amazing ocean views West Maui has to offer. It’s arguably the best unit at Kaleialoha. Entire left wall has tinted widows for privacy, feels like your outside with nature. The...
FOUR SEASONS RESORT "HUALALAI HALE”, MODERN LUXE RETREAT, OCEAN VIEW, 1.5 ACRES.
Hualalai Hale: Your Luxe Private 4-Bedroom/4.5-Bath, Hualalai Resort Retreat, Tropical Landscape, expansive yard, Big Island HawaiiWelcome to Hualalai Hale—Your personal luxury resort home nestled within the exclusive and gated Four Seasons Resort Hualalai on...
One Bedroom Ocean view Deluxe Luana Kai D105
D105 with AC is a gorgeous, 1 bedroom, 1 bathroom, ground floor, ocean view condo with a king size bed. It is located on the ground floor with a direct ocean view over the grassy park area and pickleball courts. The pickleball and tennis courts are located in...
Luxury 3 Bed, 3 Bath Beach Tower B-503 Great Ocean And Pool Views
Ko Olina Beach Villas.This property is one of the newest and most exclusive available for rent on the island of Oahu. But more importantly, this is our island home for much of the year. We love it here, and we know you will too.#503 in the Beach Tower has excellent...
Maui Resort Rentals: Westin Kaanapali Ocean Resort North Oceanfront Studio Villa
Luxury Oceanfront Studio Villa at The Westin Ka'anapali Ocean Resort Villas North. This oceanfront luxury studio villa features outstanding oceanfront views of the Pacific Ocean and sleeps up to 4 with one king sized bed and one queen sized convertible sofa sleeper. The...
2 - bedroom Waikoloa Townhouse 106, close to beaches and restaurants
New rental listing starting September 2023Welcome to our relaxing, freshly updated Villa at the Waikoloa Colony Villas. Unit 106.New furniture, and beds throughout the home! Waikoloa Colony Villas is a private gated community of luxury townhomes on the South Kohala...
🏖️Kolea Luxury | Walk to Beach, Restaurants, Shopping | Concierge Included | vrKCV
vrKCV - Kolea 16H, Professionally Managed by Kona Coast VacationsEscape to Kolea Villas – Your Hawaiian RetreatFeel your stress melt away as you step into this Hawaiian paradise, located on the edge of the Pacific Ocean. Nestled within the prestigious Kolea Villas in...
Hualalai Four Seasons Guest House Complete with Golf Cart
"Ka Hale Ulu Le'a" means "House of Happiness" in Hawaiian, and this is the feeling you experience when entering this Hualalai property.This 5-bedroom, 5 Bathroom Family Oasis sleeps 10 for the ultimate family getaway, in a prime, close-in location at the exclusive Four...
Hanalei Bay View Retreat - An Artistic home overlooking Hanalei Bay
Welcome to Hanalei Bay View Retreat, overlooking Hanalei. Nestled at the edge ofPrinceville/Hanalei and centrally located to stores and restaurants as well as all the NorthShore’s best adventures. Adjacent to a forested greenbelt just beyond your windows, you’ll...
Hale La- Luxury Beach House with Central Air Conditioning!
Hale La in Kekaha, Kauai~ TVNC-4251 TA-000-602-1120-01Imagine spending your next vacation at one of the most beautiful properties on Kauai! Your days are filled with exploring miles of white sand beaches steps from your luxury vacation home, hiking the adjacent Waimea...
Villa de Aloha at Kolea Villa Big island Hawaii !
Luxury Kolea Villa at Big Island Waikoloa ResortWelcome to Big Island's most luxurious condo Kolea Villas Resort in front of A bay ( aka Waikoloa Beach )! We just fell in love with Kolea Villas here so beautiful and luxurious ! Plea come and say Hi to anyone here with...
2 BDRM w/ 4 Beds + 2 Bath + Parking + Partial Ocean View, 2 mins walk to Beach
Legal vacation rental at a fabulous location! This renovated 876 sq ft, 2 bedroom 2 bath with 2 balconies home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! There are endless shopping, dining, and activities...
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage
Maui Permit #BBPH 2009/0002 , Hawaii Permit #SUP2 2002/0005Hawaii Tax I.D. TA035-442-8928-01 TMK (2)2-7-035-010-0000Maui's Ultimate Private, Romantic Cottage! ...a unique architectural Polynesian Pole home on Magical Maui. Secluded, romantic, beautiful island inspired...
UPGRADED-Oceanfront-3 BR-Sands of Kahana-Central AC.
Sands of Kahana unit 275 on the 7th floor in the ocean front building 2. Location, location, location! Located between Kaanapali and Kapalua you will the quaint town of Kahana. Kahana-Napili affords some of the best dining and Luaus on the island, and is perfect for...
Waikiki Tropical Getaway with Pool and Free Parking!
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...
Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach
RELAXING GARDEN RESORT:Kihei Resort offers a wonderful zen like experience. As you walk through the grounds of Kihei Resort, it is difficult not to enjoy the serenity of the beautifully landscaped grounds, smell the plumerias and hibiscus, as well as listen to the...
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with...
Fully Remodeled Ocean Front Comfort HKOK316
Hawaii Tax ID: TA-101-435-1360-01TMK: 390080030055Oceanfront Bliss in North Kihei CondoWelcome to your private slice of paradise in North Kihei, where breathtaking ocean views await you from the moment you step into Unit 316. Experience the magic of Maui's coastline...
KAANAPALI - FULLY RENOVATED WITH OCEAN VIEW
Welcome to B208! This is a stunning ocean view home at beautiful Papakea Resort. Our condo is conveniently located on the second floor with very close access to the ocean and the pool area in building B. This is a legally permitted vacation rental and hotel zone...
OCEANFRONT BEACH HOUSE WITH SUNSET VIEWS AND PRIVATE POOL
Kona Bay Estates is a gated and patrolled oceanfront community. The Sunset Beach House offers 2700 square feet of luxurious space. It is just 500 meters from the sea. Opening walls of glass offer indoor-outdoor living with spectacular views of the ocean and a private...
Paradise Awaits in this Luxurious Villa in Ko Olina
Luxurious 3 bedroom Villa located in West Oahu. Enjoy all 4 of Ko Olina's ocean lagoons. Walking distance to Four Seasons, Disney Aulani, Marriott Beach Club, Ko Olina Center (shops and restaurants), Ko Olina Golf Club, Roy's Restaurant, and Monkey Pod Restaurant.State...
Fresh 1 Bedroom with Parking at Waikiki Banyan !!
Freshly Furnished One Bedroom Unit at the Waikiki Banyan with Peakaboo Diamond Head Views! One Free PARKING already included (max 6'), Bedroom with 1 Queen + 1 Full Bed; Living room with 1 Full BedCoin and App Operated washer and dryer on the same floor.Waikiki Banyan...
❤️PiH❤️ Pualani Villa ★Elegance★Heated Pool & Spa★Private Cottage
Introducing Pualani Villa, by Paradise in Hawaii Luxury Homes.At Paradise In Hawaii, we pride ourselves on providing some of the most sought after homes on the Kohala Coast and are thrilled to add the exquisite Pualani Villa, a single level four bedroom home, with pool...
Hali'i Kai 12E: Beautiful Oceanview Villa w/Resort Pool, Spa, BBQ, AC & Lanai
Experience the epitome of island luxury at Haliʻi Kai 12E, a stunning 3-bedroom, 2-bathroom corner villa nestled within the prestigious Haliʻi Kai Resort on the sun-drenched Kohala Coast of Hawaiʻi's Big Island. This ground-level retreat offers sweeping views of the...
Papakea Resort E305 is Open! Please Visit West Maui & Help Our Businesses.
ALOHA,As an owner at Papakea Resort and living on the west side of Maui, we lived thru the devastation of the wildfires that took our precious Lahaina town, on August 8, 2023. Many locals lost their homes and businesses, and many need your help by returning to paradise....
Best View in Town, A205 come check out the View
Lokelani A205. Enjoy breathtaking, unobstructed views of neighboring islands Molokai and Lanai. The surf is just 30 feet away from two private balconies – the perfect vantage point for whale and sea turtle watching, as well as our legendary Hawaiian sunsets. Enjoy the...
Kona Palms#201:Oceanfront with great views, AC, elevator and wraparound lanai
Gorgeous views from this spacious and updated 1041 square foot condo with 2 bedrooms, 2 bathrooms and Sleeps 5 to 6! Picture yourself relaxing in this absolutely beautiful condo, enjoying the ocean views, while watching surfers and the magically blue waters of the...
2 Bedroom Kona Coffee Farm with Ocean Views in Holualoa
The rental is the entire downstairs with it's own private entrance and large patio with BBQ. The downstairs has two separate bedrooms with a large family room in the middle. The kitchen has a refrigerator, sink, microwave, two burner hotplate, toaster over, and coffee...
South Kihei Condo; Steps to Beach!!
Aloha!Enjoy this awesome 2nd floor unit, steps to the beach, shopping and dining, with a partial ocean view from the living room and lanai.The property has 1 pool, barbecue grills located directly outside the unit just downstairs, and beautiful landscaping throughout....
Maui Resort Rentals: The Whaler 724 - Corner 1BR/2BA w/ Wrap-Around Balcony, Gorgeous Partial Ocean and West Maui Mountain Views!
From its desirable 7th-floor corner floor plan, Whaler 724 delivers gorgeous views of the turquoise-hued Pacific, Maui's neighbor island Molokai, and the lush West Maui Mountains. During the winter months, this spacious 1BR/2BA suite enjoys an excellent vantage point...
Wyndham Kona Hawaiian Resort
Please note, that some holiday weeks require a seven-night stay, please confirm with an agent. Prime weeks and holiday weeks have higher rates, your agent will send you an initial quote based on the dates you have chosen.Thank you for choosing Dash Realty Group of...
Pili Mai 5D - Luxury 3bed/3bath, Sunny side
Make yourself at home in this luxury three bedroom, three bathroom condo located on Kauai’s sunny south side! A generously open-floor plan allows for abundant natural lighting and air flow throughout the entire home.The spacious living room features comfortable...
Tropical & Elegant- Sleeps 8- Ocean/Waterfall Views
Ala Hale is a luxurious island retreat with stunning views of the ocean & majestic mountain views. Located on the Makai Golf Course at the 6th hole, within the prestigious resort community of Princeville, Ala Hale's large private pool and spacious lanai's let you...
Newest 2 BR at Maui Eldorado, prime Ocean View
Enjoy your next family getaway in centrally located Kaanapali beach resort area with spacious 1440 square feet plus double length lanais. Ideal for a family up to 6 person, this accommodation offers premium ocean and golf course views and amenities such as shared pool,...