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.
Timbers, Hawaii's Finest 5 Star Resort, Luxury Pools, Golf, Dining, Oceanfront!
Experience refined island living at our luxury oceanview residence at Timbers Kauaʻi, Hawaii's finest 5 Star Resort. Overlooking the Hokuala lagoon, Kalapaki Bay, and the Haʻupu mountain range, this elegant residence features three ensuite bedrooms, a gourmet kitchen,...
Lanai Luxury, Expansive Suite Connect, Sleeper Sofa - Romer House Waikiki
This listing is for a room within a hotel.✦ Your room is 878 sq. ft, equipped with complimentary toiletries, TV.✦ Cleaning services included in the nightly price.There are a few additional details to know before you book:✦ The minimum age required for check-in is 18...
Aloha Surf Condo - Private Deck - Pool - E-bikes
About this spaceWelcome to the Aloha Surf Condo at Kuilima Estates East, nestled within the Ritz-Carlton Turtle Bay Resort on Oʻahu’s North Shore. Wake up to palm trees swaying across the golf course, then stroll or ride your two Rad Power RadRunner Premium E-Bikes...
Lahaina Luxury One Bedroom Villa at Maui Bay Villas Hilton Grand Vacations
Escape to Maui Bay Villas, Hilton Grand Vacations’ stunning oceanfront resort located along Maui’s picturesque western shore. This one-bedroom villa located n the Mauka side of the resort, blends contemporary island elegance with all the comforts of home, making it the...
Hapuna Beach Residence B12 at Mauna Kea Resort
This island luxe, oceanfront, newly-constructed, ground level island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a fantastic chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
First Floor Beach Studio Across the Street from the Beach!
Welcome to our bright & clean beachside retreat in North Kihei! Our studio condo is directly across from the beach and stocked with all the comforts of home. Enjoy keyless entry, fast WiFi, free parking directly in front of the first floor condo, and a stocked, full...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Ocean View | 3 Units, 4 Bedrooms | HK ML-1766
** 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...
Modern Tropical Retreat with Kitchen, Relaxing Ambiance and Serene Surroundings
Our villa offers sweeping Pacific Ocean views and island breezes from a private lanai. Enjoy bamboo linens, a gourmet kitchen, and access to the oceanfront club with lagoon pool and seaside dining. Steps from Waikoloa Beach Resort golf and minutes to Hapuna Beach,...
Sun-Soaked Balcony with Ocean Views, Walk to Beach, Shops, & Cafés
Family-friendly property located just steps from the beachThis listing is for a room within a hotel.✦ Your room is 443 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high definition 32-inch TV, available with Premium cable, ensuring...
Making The Best Memories Along The Way! Outdoor Swimming Pool, Gym Access!
The excitement of Waikiki Beach is at your doorstep at this Honolulu property!This listing is for a room within a hotel.✦ Your room is 453 sq. ft, equipped with complimentary toiletries, high definition 46-inch TV, available with Premium cable.✦ Cleaning services...
Royal Kahana Maui 202 Ocean View Studio
Enjoy stunning sunsets from your ocean-view studio, an ideal retreat couples looking to relax in paradise. Unit 202 Ocean View Studio• 2nd floor studio with balcony • Studio kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, toaster, blender,...
Island Colony 9th Fl Studio - Pool View
🌴 Island Colony Studio – Pool Views & Steps to Waikīkī BeachGorgeous modern studio with views overlooking the recreation deck and pool, perfectly located in the heart of Waikīkī. The spacious lanai with seating for four invites you to relax, share meals, or simply enjoy...
Island Escape – 2BR Lockoff Villa at Sheraton Kaua‘i Resort
Enjoy the perfect combination of space and flexibility in this 2-Bedroom Lockoff Villa at Sheraton Kaua‘i Resort, located on the sunny South Shore in Po‘ipū. With about 1,100–1,200 square feet of space, this villa comfortably accommodates up to six guests, making it...
Royal Kahana Maui 306 Ocean View 1 Bedroom
Step into this inviting one-bedroom unit featuring sweeping ocean vistas and a cozy atmosphere near many beaches. Perfect for couples, small groups, or retreat seekers. Unit 306 Ocean View 1 Bedroom 1Bath• 3rd floor condo with nice views of ocean and the island of...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Exceptional Value | 3 Units, 6 Bedrooms | HK ML-1628
** 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...
Peek-a-Boo Ocean View Studio in Waikiki w/ AC - Bamboo Waikīkī Hotel #803
Castle Bamboo Waikīkī Hotel #803 - Expansive sliding glass doors allow for natural sunlight and open to the private outdoor lanai where you can relax in comfort while taking in the views and enjoying your morning cup of coffee. The sleeping/living area is furnished with...
Vehicle to rent, Hilton Pass, Family Friendly, Grill, Beach Gear, 3bedroom, N1
This pristine 3 bedroom, 3 bathroom home has 1,725 square feet in 2 stories with expansive outdoor spaces and backs up to Hole 3 of the prestigious Waikoloa Beach Resort Golf Course.Primary Bedroom: enjoy serenity in your primary suite. King bed, large walk-in closet,...
Ohana Villa Princeville • Pool & AC • Sleeps 20+
Aloha & Welcome to Ohana Villa — Your North Shore Retreat!Escape to paradise at Tropical Ohana Villa, "Ohana" means family, and this is a spacious and newly upgraded 6-bedroom, 2.5 bathroom, AC & private pool/jacuzzi home perfectly situated in the heart of Princeville,...
New Listing! Lovely 2bd in Kihei, paradise awaits!
Welcome to Maui Banyan P409 – Bright 2-Bedroom Suite Relax and unwind in this beautifully updated 2-bedroom, 2-bathroom corner unit at Maui Banyan, comfortably accommodating up to 6 guests. With two separate entrances and a lock off option for added privacy, it's...
Waikiki Cozy and Spacious Studio with Balcony
Relax at Luana Waikiki Hotel and Suites, a newly renovated, spacious unit. Conveniently located near the entrance of the iconic Waikiki strip, a short walk to Waikiki Beach, shopping, dining, and the Convention Center.It comes with one queen bed & one queen sofa bed,...
Ocean Views Top Floor Across from Beach - Kihei Akahi D606
Book with us and come to Maui to explore everything we have to offer!Looking for an ocean view, close to the beach, and a convenient location that fits your budget? This condo is for you! New: furniture including Cal King bed, couch, Roku TV, artwork linens. A sofa...
Kahana Villas Resort & Spa, Lahaina, Hot Tub, Pool
Enjoy returning each day to your luxurious suite with views of the ocean worthy of a postcard! Kahana Villa offers one-bedroom and 2-bedroom suites featuring a fully equipped kitchen, in-room washer/dryer and private lanai. All two-bedroom units at this resort are two...
Fully renovated ocean facing condo in Kauai with Pool/AC/Hot-tub
ALOHA! Welcome to our fully renovated ocean-facing, beach-house–style condo at Plantation Hale in Kauai. Bright coastal décor, natural textures, and island breezes create an effortless, relaxing vibe. Wake up to the sounds of the ocean and relax on our expansive lanai,...
Kapalua Golf Villas | Large Bedrooms | KBM Resorts | 3 Units, 4 Bedrooms | ML-2297
** 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...
Sunny Hilo Home w/ Game Room: Walk to Golf Course!
Aloha, and welcome to Hilo! This spacious 3-bedroom, 2-bath vacation rental, on a quarter-acre of lush Hawaiian land, offers all the comforts necessary for an ideal extended stay. Boasting a game room, in-unit laundry, and a central location near many attractions, this...
1 bedroom condo with great Waikiki view
Perfect 1 bedroom in 38th floor. You may view 180 degree panoramic ocean view from the living room!!As you enter, you will find the fully equipped kitchen just remolded. In the bedroom, there is queen size bed for your full recharge. Through the bedroom, you can go to...
Hawaiian Getaway: 2BR at Hilton Grand Islander in Waikiki
Discover the perfect blend of space, comfort, and resort living in this two-bedroom, two-bathroom suite at The Grand Islander, a Hilton Grand Vacations Club in Waikiki. With accommodations for up to six guests and all the comforts of home, this suite is ideal for...
Relax, Unwind, Repeat – Lahaina Shores 527 Getaway
Wake up to the sound of waves and endless blue horizons — this 5th-floor oceanfront studio puts Maui's beauty right outside your door.Set directly on the shoreline in historic Lahaina Town, Lahaina Shores is a charming boutique resort where the ocean is just steps from...
New Listing Kalnikai 213, close to Ironman start! by Coldwell Banker
New Listing Kalanikai Unit 213, Walk to Ironman Start, Pier and Ali'i Drive!Welcome to Kalanikai Unit 213, your perfect Big Island getaway nestled in the heart of Kailua-Kona! This beautifully maintained unit offers a serene retreat just steps from the action. Ideal for...
Dreamy Ocean Views, Private Lanai, Updated Kitchen
Experience the best that Maui has to offer at our updated coastal retreat with dreamy ocean views and a large private lanai. Stroll to the beautiful, world-renowned beaches, dine at delicious local restaurants, and shop at charming boutiques. South Maui's main surf...
** 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...
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,...
Sleeps 12! Ocean Views! 4 BD/4BA! 2 Renovated Condos!
Room for 12! Welcome to Pineapple Paradise Maui - The Original and 2.0!Bring your whole group to enjoy these TWO incredible 2 bedroom 2 bathroom condos only 1 minute walk from each other and a 2 minute walk to the beach! Both condos have just been completely remodeled!...
🏖️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,...
Free parking 2-bedroom condo in Waikiki, cool breeze w/A/C. Sleeps 6
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...
Beautiful Modern Decor in a Light-Filled Condo, Hale Kamaole, Steps to Beach
This ground floor unit is perfectly located and easily accessible to all the complex's amenities: sparkling clean pools, gas and charcoal BBQs (cleaned daily), and a tennis court. You also have your own personal lanai to enjoy the cool island breeze as you sip your...
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...