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.
3 Bedroom Ocean View Townhome
The main living area of Halii Kai 11F has two luxurious soft sofas facing an armoire with a SMART TV and a DVD player. Adjacent is the dining area with a large table seating 6. The large kitchen has a wrap around granite counter with 3 bar stools and stainless steel...
Beautiful Oceanfront Estate with heated saltwater pool, Hamakua Coast Acreage.
From the moment you arrive, your every care will melt away at this spectacular gated oceanfront estate. The open floor concept, covered outdoor spaces with BBQ, and poolside gathering areas, are ideal for family vacationing. Hear the sounds of the surf along the rugged...
Gorgeous two-level condo with resort-style pool & hot tub - close to beach
Ka Pu'uwai at Nihilani 29BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A lush exterior, with a gorgeous resort-style pool and hot tub, and a bright, modern interior with two...
Ko'Olina Retreat - Short Walk to Resorts, Golf, Restaurants & Lagoons!
Welcome to your dream retreat in the heart of Ko'Olina! This beautifully remodeled 3-bedroom, 3-bathroom townhome is nestled in the exclusive, gated community of Ko'Olina Kai, offering the perfect blend of luxury, comfort, and island charm.Step inside and be captivated...
Mahana Beachfront Walkout
Maui Gov’t Approved Short Term Rental. We are the owners (Barry Travers and Rhonda Anderson) of Mahana 118 and we own several Maui properties with hundreds of 5 Star reviews for our properties as we provide the ultimate guest experience! Mahana 118 is an AMAZING...
Waipouli Beach Resort Luxurious 5 Star Ocean Front Complex A-201 Pool and AC
If you’re seeking a 5 Star premier vacation condo experience, look no further. This deluxe oceanfront condominium property offers luxurious units with rich hardwood furnishings, gourmet kitchens, and spacious baths. A beautiful, heated river pool meanders through the...
New!-*Fall Special Rates* #510-Ocean-Sunset Views! Steps from It All!
New Listing!*Autumn Specials: Reduced rates and discounts for stays 7 nights or more. Excludes Dec 20-Jan 5*Stay with a small, local company with the experience to make your trip seamless, but who truly cares that you feel at home and enjoy every moment of your...
🌊 EPIC Oceanfront Condo at Hale Kona Kai #403, TOP FLOOR, ELEVATOR, CENTRAL AC 🐬
Aloha and welcome to HONU HIDEAWAY at Hale Kona Kai #403. This is the absolute destination should you want a relaxing vacation getaway on the Kona coast. The location of this condo complex adds convenience as fun activities and amenities are within walking distance. The...
Bamboo Canopy with Shared Bath and Common House
Escape to the enchanting Bamboo Canopy, a glamping-style retreat. This unique accommodation offers the perfect blend of rustic charm and modern comforts, making it an ideal choice for those seeking a tranquil yet luxurious getaway.The Bamboo Canopy features a queen-size...
Magnificent Views of the Mighty Pacific Ocean from Every Room
Enjoy the beautiful North Shore of Kauai at our lovely Alii Kai I Condominium. It is a ground floor, corner unit sitting on a bluff overlooking the magnificent Pacific Ocean. In the winter be mesmerized by 15 to 25 foot waves. Whales cavorting in the ocean and...
Gorgeous 3b/2b house minutes from Natl Park & Volcano Village. Family friendly!
Tree Fern Escape is a cozy and comfy getaway just minutes from the Volcano National Park. This 3 bedrooms, 2 baths charming property, has gorgeous hardwood floors, newly furnished with large private backyard. Large enough for big families, cozy enough for couples.Large...
Steps from Paniau Beach
House or Cottage or both together(see listing #956147 for Cottage) PLEASE NOTE... Listed rates are based on two guests. An additional $50/per nt per extra guest will be added. Please enclose total number of guests when booking......Located at the private and quiet end...
Watch for albatross and nene from ocean view beauty
Located on the North Shore of Kauai in Princeville, Ka Mea Nui is surrounded by lush tropical landscapes overlooking the Pacific Ocean and the 15th hole of the Makai golf course. The verdant golf course is a favorite playground for endangered nene (Hawaiian geese) and a...
Maui Resort Rentals: Kaanapali Ali'i – Oceanfront Ground Floor + Yard Area, 4 Total Bedrooms+DEN, Sleeps 14
This one-of-a-kind Oceanfront 4BR+DEN ground-floor offering at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach is comprised of two luxurious adjacent suites. Together they offer a massive 5,188ft of combined interior living area and a sleeping capacity of...
Waikiki Beach Penthouse
Located just a block from Waikiki Beach and surrounded by top-tier hotels, this gorgeous penthouse condo offers the style and comfort of a luxury hotel with the added benefits of 1700+ square feet of living space, a large well-appointed kitchen, extra-large private...
Makanui 711 - Garden/Mountain View
MAKANUI 711 AT KOLOA KAI VACATION RENTALSYour Charming Beach Oasis in PoipuWelcome to Makanui 711, a delightful 1-bedroom, 1.5-bath condo offering a perfect retreat in the heart of Poipu. Located just a short stroll from Poipu Beach, Brennecke’s Beach, and Shipwreck...
Beautifully remodeled Sugar Beach #104, meticulously cleaned and maintained
Welcome to our beautifully remodeled ground-floor condo at Sugar Beach Resort #104 in North Kihei! Experience island living in this beautiful condominium situated along Maui's 5 mile Sugar Beach. With direct access to one of the longest stretches of sandy beach on the...
Live like a Local. Stay at a Beautiful Boutique Get Away Mokuleia Beach Colony
Mokuleia Beach Colony is a perfect country base or north shore retreat in a manicured tropical gated community! 200 yards from the ocean. Easy private beach access, outdoor shower, heated pool, tennis courts, one reserved parking stall and pickball on-site. Fully...
Relaxing Ocean Front Views on Maui! Island Sands Condominium
This rare ocean-front condo is stunning! Listen to the sound of the ocean from the comfort of your home, while watching whales (Dec-April) and Hawaiian Green Sea Turtles all year long! Located a five minute walk from boats, Maui Ocean Center Aquarium, shops and...
Pauoa Beach Estate: Stunning Villa with Ocean Views, Pool, Home Theatre + Resort Amenities
Enjoy luxury living and ultimate relaxation at the gorgeous Pauoa Beach Estate. The 4 bedroom, 5.5 bath villa is located in the exclusive oceanfront enclave of Pauoa Beach, a short 800 feet from the sparkling blue Pauoa Bay.Over 1000 square feet of outdoor lanais...
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 five-bedroom, five-and-a-half-bathroom hideaway designed for up to twelve guests. Located off the first tee of the Kukui‘ula Golf Course in Koloa, this 3,500-square-foot single-level estate blends barefoot luxury with...
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...
Blue Hawaii: Luxurious Oceanview Home with Pool, AC & BBQ Lanai
Blue Hawaii by Gather delivers a grand island escape in Kona’s sought-after Keauhou Estates. With 3,200 square feet of interior space, an expansive solar-heated infinity pool, and multiple private sleeping suites, this home was designed for large groups to relax,...
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...
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...
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...
4Bed Beachfront home near Pipeline
Make yourself at home in this 4-bedroom 3.5-bathroom North Shore piece of paradise. This wonderful house boasts 1 king bed, 3 queen beds, and 1 twin bed, perfect for a tranquil getaway. With beachfront views from 3 out of the 4 bedrooms and all bedrooms with their own...
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...
Sept-Oct Special! 1,800! Hualalai Four Seasons 5-Bedroom House Close to Resort
"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...