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.
Maui 2BR Ocean-View Villa at Marriott’s – Full Kitchen, Lanai & Kaanapali Beach
Discover island comfort and spacious living in this two-bedroom, two-bath villa at Marriott’s Maui Ocean Club – Lahaina & Napili Towers, nestled on the sun-drenched Kaanapali Beach in West Maui. Ideal for families or groups, the residence features a master bedroom with...
Stunning remodeled oceanview in the heart of Kihei
Welcome to Kihei Akahi C610. This beautifully remodeled 6th floor ocean view condo is the perfect place to make your Maui memories. This condo has been completely remodeled with high end finishing, and split AC throughout. Admire sunsets & ocean views from your private...
4 Suites with Balcony and Living Area | Outdoor Pool & Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
🏖️Tropical Top-Floor Getaway • Fairway Villas G32 w/ Loft & Views
Fairway Villas G32 – Welcoming, Bright, and Tropical Top-Floor RetreatWelcome to Fairway Villas G32, a spectacular sun-filled condominium offering charming, bright, and tropical living in the heart of Waikoloa Beach Resort. Designed for guests seeking a quiet,...
Convenient free parking 2-bedroom condo in Waikiki with cool breeze and A/C.
THIS CONDO IS CURRENTLY BEING REMODELED AND WILL BE FINISHED IN APRIL. PICTURES MY OTHER UNIT IN THE SAME BUILDING, SAME FLOOR PLAN, SIMILAR FURNISHINGS.Welcome to this fabulous condo in Honolulu. This perfect two-bedroom retreat features a queen bed and a full bed,...
Hillside Villas 1498-3 by Gather w/ Garden Views, Close to Golf & Beach
Set within the quiet Hillside Villas community in Ko Olina, Hillside Villas 1498-3 by Gather offers a comfortable retreat designed for long-stay relaxation. This two-story townhome features soothing garden views, a welcoming open layout, and the convenience of nearby...
Brand new! Cozy and safe lockout unit in Kihei condo. Close to everything!
Escape to this charming studio in picturesque Kihei. This fabulous rental features 1 cozy bedroom with a queen bed, perfect for a single or couple's getaway. Enjoy the convenience of amenities like WiFi and AC during your stay. Experience the magic of Kihei at this...
Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to Attractions
Welcome to Kailua Hale Kahakai, a serene beachfront estate set along one of the most breathtaking stretches of Kailua Beach. With six bedrooms, five bathrooms, and over 4,300 sq. ft. of breezy living space, this expansive retreat blends open-air island design, panoramic...
Westin Princeville Ocean Resort Villas | 2BR Villa
Summary:With its cascading waterfalls, tropical rainforests, and mountainous landscapes, Kauaʻi is a magnificent vacation destination. The Westin Princeville Ocean Resort Villas offers a collection of amenities to keep you entertained without ever having to leave the...
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
Named after one of Kauai’s most majestic places Waipo’o Falls, this brand-new home is the perfect place to enjoy all the best that Kaua’i has to offer. With luxury and elegance from the moment you pull into the driveway, Hale Waipo’o is sure to be your luxury home away...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Breathtaking Ocean Views + Luxury Amenities + Gorgeous Beachfront Retreat
The Space:Welcome to our 1 BR Oceanfront home in Kahana, conveniently located at the prime location in the heart of West Maui within walking distance to some of the island’s most popular spots, including local favorites. ✔ Oceanfront Home✔ Air Conditioning (A/C)✔...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Stunning Views-North Shore jewel. One block to beach.
Aloha! North shore Kauai, deep in the jungle but only 5 houses to the beach. One mile to the famous Tunnels Beach. Private and quiet gated estate. Half acre of flowering plants and ediable fruit trees- flat land with stunning views of the mountains. You're in mystical...
Ko Olina Kai 1105E: Upscale 3BR, BBQ Lanai, Near Golf & Disney Resort
Tucked within the serene Ko Olina Resort community, Ko Olina Kai 1105E offers a welcoming retreat where comfort, connection, and island living come together effortlessly. This refreshed 3-bedroom, 2-bath upstairs condo spans 1,427 square feet and is designed with...
Tropical Paradise Awaits: Marriott's Maui Ocean Club for Family Fun
Immerse yourself in Hawaiian luxury at Marriott’s Maui Ocean Club - Molokai, Maui, & Lanai Towers, a breathtaking resort on the golden shores of Ka’anapali Beach, where every moment feels like paradise.Spacious accommodations designed for families include one-, two-,...
Marriott's Kaua‘i Beach Club | Two Parlor Suites
Summary:Experience the beauty of Kauai from the cozy parlor suite, the resort offers ocean views and easy access to Kalapaki Beach, consistently ranked among Hawaii's best swimming beaches. Enjoy resort amenities including a communal pool and hot tub, and relax on your...
Hale Namakeha! Brand New Construction with Exquisite Design! Mins to Beach with Air Conditioning!
Summary:Nestled in the heart of Princeville, this exquisite home captivates luxurious amenities, and meticulously designed interiors.The Space:Enjoy brand new construction & professional design with air conditioning! Located in the lush landscapes of Princeville,...
Making The Best Memories Along The Way! Outdoor Pool, Oceanfront!
When it comes to comfort, convenience, and an aloha spirit - you found the right place to stay. Relax by the pool, indulge in our buffet dinner, and enjoy views out over Kahului Bay. All this is yours within 10 minutes of the airport, and you'll be close to many of the...
Cozy 1-bedroom condo with AC, fitness room in welcoming Kihei
This brilliant 1-bedroom condo in Kihei is perfect for your escape to relaxation. With a cozy king bed and a charming living room featuring a comfy murphy bed, guests can unwind in style. Enjoy the convenience of a fitness room, washing/drying machine, full kitchen,...
Aqua Aloha Surf Waikiki 1513 - Studio hotel room with a Lanai and Partial City V
Aqua Aloha Surf Waikiki 1513 - Studio hotel room with a Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, Sleeps 2. Square footage: 301.Aqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for...
2 Spacious Room Perfect For Family Stay with Balcony | Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
ML - Nohea Stylish Home w Perks I Near Top Sight
Summary:This home is perfect for families or groups of friends looking for a relaxing and luxurious vacation located in a gated private community in the heart of the Makaha Valley It s just minutes away from Makaha Beach Park a popular surfing spot and the great golf...
Kaanapali Maui Eldorado H204 Garden 1BD + Bonus BD
Tucked away on Kaanapali golf course, this garden-view retreat includes one bedroom and a bonus room for extra flexibility. Just a short walk to the beach, it features a fully equipped kitchen, comfortable living space, and plenty of room to relax. Unit H204 Garden View...
Spacious Waikiki Beach Condo with 2 bedrooms 2 baths
Just a few minutes walk from the famous beaches of Waikiki, this spacious, ocean facing unit with 2 bedrooms 2 full bathrooms in Discovery Bay gives you the perfect opportunity to live the Hawaii city life with tree top and ocean views. Just two floors away from the...
High Floor 1 BD Condo - Steps away from the beach!
Wake up to gorgeous mountain views in this 30th Floor, corner-end unit at Waikiki Banyan!Perfect for hosting guests while you visit, this unit features a large, leather couch, a work station, a dining table with seating for 4, as well as 2 adjustable bar-stool chairs...
Luxury Meets Aloha — Oceanfront Paradise at Lahaina Shores 529
Lahaina Shores 529 is a perfect studio getaway!Outstanding, endless Pacific Ocean and neighboring island views from your private lanai. Set directly on the shoreline in historic Lahaina Town, Lahaina Shores is a charming boutique resort where the ocean is just steps...
Renovated 3BR w/ AC, Vaulted Ceilings & Lanai Ocean View Near Airport
Enjoy a partial ocean view from the lanai at this freshly remodeled (July 2025) Kona retreat. The bright, spacious home features vaulted ceilings, air conditioning, and year-round comfort at 1,070 ft elevation. Just 3.5 miles from the airport, you’re minutes from...
Kiahuna Plantation Resort Ocean View 2 Bedroom
Enjoy sweeping ocean views from this spacious split-level two-bedroom condo on Kauai’s most iconic beach. Perfect for families or couples traveling together, it offers comfort, space, and stunning scenery. Ocean View 2 Bedroom 2 Bath• Fully equipped kitchen includes...
15th Fl Luana Waikiki Studio | City & Mountain Views | Pool | Balcony
Enjoy a stylish 15th-floor studio at the Luana Waikiki, featuring city and mountain views just steps from Waikīkī Beach. Perfect for couples or small families, this boutique stay sleeps up to 4 guests and includes a kitchenette, pool, fitness center, and BBQ area — all...
Kapalua Bay Villa 36B3 Oceanfront 1 Bedroom
- Split level Condo- Villa closest to Kapalua Beach- No stairs between parking lot and front door- Tile flooring throughout and carpet in bedroom- Kitchen with stainless steel appliances – fridge with ice maker, stove/oven, microwave, dishwasher, cookware, tableware-...
Ilikai Hotel One-bedroom Unit with am AMAZING view of the Duke Kahanamoku Lagoon and Waikiki Beach
This condo is located on the floor of the 12th Ilikai Hotel.This AMAZING condo has beautiful views of the ocean overlooking the lagoon at the Ilikai Hotel. Relax in this cozy, Hawaiian styled condo. You'll love waking up to the beautiful and calming view of the ocean...
Hapuna Beach Residence B11 at Mauna Kea Resort
This oceanfront, newly-constructed, ground-level masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a magnificent chefs' kitchen with Wolf, Sub-Zero and Miele appliances, including double ovens and a wine refrigerator, as...
Penthouse Paradise 2 Bedroom Apartment on the water, overlooking Hilo Bay!!
Nestled in Hilo, this delightful condo offers a serene escape for guests. With 2 bedrooms featuring a queen and king bed, along with 2 bathrooms equipped with showers, this phenomenal property ensures a comfortable stay. Enjoy amenities like WiFi, a fitness room, AC,...
Maui Resort Rentals: Kaanapali Alii 313 - Ground Floor 1BR Steps from the Beach with Expansive Lawn!
Maui Resort Rentals is proud to present this luxurious 1BR residence at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach—newly launched on October 21, 2025 to start taking bookings for check-ins starting December 19th, 2025!Nestled just one column back from...
Our newly renovated attached studio is located between Sunset Beach & V-land one block to the beach. Well suited for a single guest or couple (queen loft bed) who want to enjoy the comforts of home while experiencing the North Shore culture. Walk distance to beautiful,...
Ocean View by Beach - Kihei Bay Vista A106
Book with us and come to Maui to explore everything we have to offer!This updated and comfortable vacation home is just steps from the beach. The unit has both a queen bed and queen sofa bed. The bedroom has an A/C. The stylish bathroom features a tiled, walk-in shower....
Kaanapali Alii 11111 Bedroom | 2 Bathrooms | Sleeps 4 | Partial Ocean View_________________________________________________Welcome to Condo 1111 at the Kaanapali Alii Resort, a stunning 1-bedroom with a partial ocean view overlooking the turquoise waters of Maui’s famed...
Hanalei Bay Resort 4302: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Overlooking the legendary Hanalei Bay on Kauai’s lush North Shore, Hanalei Bay Resort 4302 offers an inspiring island retreat with sweeping ocean, mountain, and Na Pali Coast views. Designed for couples or solo travelers who crave both tranquility and connection, this...
Oceanfront condo with pool, hot tub, sauna, tennis, BBQ, putting green, & lanai
Pono Kai Resort A308Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to your dream vacation and make yourself at home in this magnificent top-floor oceanfront condo, offering...
Hualalai 4 bedroom 5 bathroom privacy, central to all Four Seasons amenities
Make yourself at home in this 4-bedroom Kailua-Kona house. The space offers five bathrooms, providing plenty of privacy and comfort for guests. Step inside to find a pleasant environment where air conditioning keeps things cool and a hair dryer and iron add convenience...
The Cliffs at Princeville Resort, Tennis Courts
You’ll love the stylish decor of this charming place to stay. Located on the north shore of Kauai, The Cliffs at Princeville lies within the Princeville Resort on over twenty acres of lush tropical land. This dream of a resort overlooks the Pacific Ocean from atop a...
Oceanfront Poipu Pool Home - Fabulous 7 BR Estate
This beautiful 7 bedroom for 14 oceanfront pool home is only 75 yards to famous Brenneckes Beach! Enjoy uninterrupted sunrise and sunset views from your oceanfront pool and jacuzzi. Enjoy the playfulness of breaching whales and spinner dolphins by day and the quiet calm...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
New Listing! Paniolo Club, Ground floor, BBQ, WIFI by Coldwell Banker
Welcome to the Big Island Paniolo Club 114, a stunning two-bedroom, two-bathroom vacation rental nestled in the heart of Waikoloa Village. This thoughtfully designed property comfortably sleeps up to four guests, making it perfect for family getaways or a group of...
Walua Trail Oceanview Hideaway:A/C/W/D/Parking
A small suite to the side of a home. No one above or below you. Separate parking, entrance makes it quiet and private. Guests can access to yard to pick fruit when in season. Nice two person deck that has Ocean views and beautiful sunsets. Split A/C unit recently added....
One-Bedroom Villa with Balcony and Resort View
Nestled in Lahaina, this delightful villa offers a cozy retreat for guests. With 1 charming bedroom featuring a king bed and a lovely living room with a sofa bed, this marvelous property is perfect for a relaxing getaway. Enjoy the convenience of WiFi, a washing...
Bay Villas Gold Ocean View 1 Bedroom at The Kapalua Villas Maui, Kitchen
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
1 Mi to Magic Sands: Waterfront Big Island Condo
Resort-Style Pool & BBQ Area | 3 Mi to Shopping Area | Covered Parking Space AvailableYour next dreamy island getaway awaits at this oceanfront vacation rental in Kailua-Kona, Hawaii! Start each day with coffee on the private balcony as you admire unbeatable views....
Ocean View Sky Ala Moana Condo w/Amazing Amenities Near Restaurants & Shops
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to The Sky Ala Moana, the newest pinnacle of luxury in Honolulu. This exquisite property, consisting...