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.
Waipouli Beach Resort E303 Garden Mountain 2B/3B
- 3rd Floor Condo with Balcony- Elevator access to all levels- Fully equipped kitchen includes granite countertops, Wolf cooktop and convection oven, microwave, dishwasher, full size Sub-zero refrigerator, coffeemaker, blender, toaster, cookware and tableware- Master...
*New Building 2 bd/2ba Parking & Pool| 30 day min
Summary:**30 DAY MINIMUM**This spectacular 2 bedroom 2 bathroom city view apartment is a fully furnished retreat!Conveniently located in the stylish Waikiki neighborhood, just 15 mins from the Honolulu Airport (HNL) the apartment is near to many local attractions,...
Stunning Beachfront Condo at Hapuna Residences
Welcome to your dream escape on one of Hawaii’s most iconic beaches. This stunning 2-bedroom condo at Hapuna Beach Residences offers unparalleled ocean and beachfront views, all upgraded and modern decor, and direct access to the soft white sands of Hapuna Beach.B48...
Fabulous 5 bedroom for 10 townhome above famous Anini Beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This beautiful 5 bedroom, 5 bath for 10 offering, is situated right above famous Anini Beach, with an 8 minute walk down the Anini Beach trail just steps away from the property. Short...
Maui 3 Bedroom Townhome Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This memorable townhome is the perfect home base for your trip to Lahaina. With 3 bedrooms including 2 king beds and 1 queen bed, this beautiful property offers everything you need for a...
Ocean view private studio W/free reserved parking!
【Basic Info】This is a studio room in Waikiki!!You can stay with you friends, partner, family. This unit has ocean view. You can enjoy the view in your stayThis condominium is located west area in Waikiki.You can walk to Hilton village lagoon and beach and Kahanamoku...
1BR Mountain View w/ Balcony, Pool & 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...
Beautiful 1-BR oceanfront villa in Ka'anapali, near the Lahaina Civic Center
PROPERTYLocated on Maui's western shore, the Westin Ka'anapali Ocean Resort Villas North is just a short distance from Black Rock Beach and Haleakala National Park. The property is less than 3 miles from the Lahaina Civic Center, where the 2025 Southwest Maui...
Tranquil Ground Floor Unit Central Honolulu w/ AC
Honolulu is waiting for you at this awesome 1-bedroom apartment - ground floor unit. This quaint space features a cozy living room with a sofa bed, perfect for relaxing after a day of exploring. The bedroom boasts a comfortable queen bed, ensuring a good night's sleep...
2 bed with office at oceanfront park & amazing views!
Just steps from the sea, this home is all about ocean view living. 2 ocean view bedrooms on opposite sides of the house maximize privacy while creating an open and social space between them. The kitchen and living space a have large French sliding doors that open wide...
New Listing! My Perfect Stays
Kaanapali Shores 732 is a Studio condo with central air conditioning that can accommodate up to 4 guests. Located on the seventh floor, you will find an open-concept layout and tropical-inspired decor with a sense of island serenity. When it's time to rest, unwind on...
Maui Ka’anapali Villas #515: One bedroom ocean view
Maui Ka’anapali Villas #515: One bedroom ocean view on N. Kaanapali Beach with Pool and Beach Access.This condominium is located on the 5th floor, and boasts magnificent ocean views. Sophisticatedly furnished with wood, tropical-themed elements, and art this suite was...
Kiahuna Plantation Resort 232 Royal Garden View De
- First floor end unit with lanai that walks out to the lawn- Bright and airy tropical ambience- Tile throughout unit- Fully equipped kitchen includes full size refrigerator, stovetop/oven, dishwasher, microwave, coffee maker, blender, toaster, cookware and tableware;...
Princeville Paradise 2BR Suite @ Wyndham Ka Eo Kai
Summary:Escape to a serene South Pacific paradise overlooking the breathtaking Anini Bay on the mesmerizing north shore of Kauai. Our resort offers a tranquil retreat where you can immerse yourself in the natural beauty and tranquility of the island. With stunning...
Ocean Villa Emilie – Contemporary Luxury with Panoramic Views in Honolulu
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Ocean Villa Emilie by Gather is a newly built,...
Palms at Wailea Garden Villas 1 Bedroom 2 Bath
Garden View 1 Bedroom 2 Bath Villa- Full kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- 1 king bed or 1 queen bed- Queen sofa bed- 1022 square feet / 95 square meters- Maximum 4...
The Westin Nanea Ocean Villas Resort & Spa, Pool!
Marriottu2019s Maui Ocean Club - Lahaina Villas is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5-acre super pool complete with a water slide, waterfalls, and children's area. The poolside...
The Blue Tide House: Steps to Maui beaches + nearby eats
Experience the best of Kihei, Maui from The Blue Tide House, located within the popular Kihei Kai Nani condos! Located on the first floor near the pool. Just steps across the street from the island's beautiful beaches, you can easily enjoy the sun, sand, and surf. A...
Maliula 2-Bdrm Superior,Unique Contempprary Traditional Hawaiian Interiors
The Hawaiian word “maliula” means enveloping in Aloha. Our Maliula vacation rentals embody a peaceful abode surrounded by nature. The interior is relaxing with greyed woods and textured white oak flooring and millwork with elegant touches of silvered iridescent...
Brand New! Luxurious Sky Ala Moana 2 Bed 2 Bath
Summary:*30 DAY MINIMUM* Discover the lively heart of Honolulu and enjoy leisurely walks along the beach with this 2 bed and 2 bathroom apartment on the 16th floor of Sky Ala Moana. Get a charming view of the city and take advantage of the convenience of being close to...
Stunning Ocean View One-Bedroom unit at Kiahuna Plantation!
New Listing on VRBO!This fabulous one-bedroom Unit, #11, is located on the second floor in Building Three. It is an upstairs middle unit with vaulted ceilings and iconic sunrises and sunsets off your deck. The unit has all the amenities of home. Including a full...
Maui Kamaole One Beachfront Condo at Charley Young Beach
Discover your perfect Maui beachfront getaway at Kamaole One #9, this beautiful 2-bedroom, 2-bath oceanfront vacation rental located directly on Charley Young Beach, the north end of the world-famous Kamaole I Beach Park in sunny South Kihei.This rare oceanfront condo...
Coconut Plantation 1222-2: Tropical Villa w/ Lanai & Pool Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available. Welcome to Coconut Plantation 1222-2 by...
Lovely Modern Complex Directly Across Kam II Beach **NEW AC!
**Magnificent Upgrade as of August 2024 - As Brand New Split AC system with individual controls in both the living room and bedroom has been installed.**Escape to paradise with this beautiful and meticulously maintained ocean view condo, nestled on the 5th floor for...
Maui Ka’anapali Villas #237: One bedroom 2 bath loft gard
Maui Ka’anapali Villas #237: One bedroom 2 bath loft garden view on N. Kaanapali Beach with Pool and Beach AccessThe space:Luxuriate in the lush garden and pool views in this Hawaiian oasis at the serene Maui Kaanapali VIllas. This condo offers indoor and outdoor...
Renovated in 2024 Studio! Just 1min to Beach@Waikiki
【Basic Info】This is a private studio unit in Waikiki!!You can enjoy your stay by yourself, friend or partner. The condominium is located east area in Waikiki.This area is really closed to the Diamond Head, Kapi olani Park.You can enjoy a walk while feeling the...
Perfect Island Getaway! 3 Spacious Units, Oceanfront, Watersports and Activities
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
Kapalua Ridge Villas Ocean View 1 Bedroom
Ridge Villas Ocean View 1 Bedroom- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Bedroom with 1 king bed or 1 queen bed-...
Hoʻonānea I Loko Kailua
If you're looking to work remotely, travel for work, remodel your home & have a place to live while it's worked on then this is the perfect home. This is a redesigned and remodel home that was originally built in the 1960's. The home is tastefully designed with a...
Waiulu Villa - Contemporary Luxury Coastal | Onsite Staff & Daily Housekeeping
This 2 bedroom, 2 bath single-level upper floor corner villa offers wrap-around views of Hualalai Mountain, the 5th hole of the Tom Weiskopf Keolu Golf Course and Punawai Pond. The large windows and 16’ sliding pocket doors provide plenty of natural light giving this...
Kapalua Bay Villa 34G5 Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- Split level condo with 16 stairs between the driveway and front door and 25 steps to Pool C- Carpet throughout and tile floors in kitchen and bathroom- Fully equipped kitchen with stainless steel appliances includes stovetop/oven,...
Ocean breezes greet you in this 12th-floor condo
Welcome to Valley Isle 1204, a 1-bedroom, 1-bathroom, 12th-floor condo that offers direct oceanfront views from your private lanai and ceiling fans throughout, as there is no A/C. This resort has elevators for easy access. Unit 1204 can accommodate up to 4 guests. The...
Brand New Rocky Point Beach Cottage
Enjoy a brand new studio just steps from Rocky Point on Oahu’s North Shore. This charming and spacious spot offers private beach access, making it the perfect getaway for surf lovers and beachgoers alike.
Newly renovated spacious studio! Great location!
Enjoy a very comfortable stay in this clean, newly renovated large studio unit with a king size bed. Just steps from beach, Honolulu Zoo, and Kapi’olani Park, this location is hard to top. Modern kitchen with cook top, allows plenty of space for meal preparation. This...
Ocean View! Marriott Ko Olina Beach Club - On The Beach- Family Friendly
Come experience Hawaii at this premium level Marriott Resort in Oahu. With luxurious amenities and great family entertainment, your family won't want to leave.This property has everything you need for a tropical vacation. There is a lagoon style family pool with...
Kaanapali Maui Eldorado B202 Garden View 1 BD
- 2nd floor condo with balcony- Wooden plank flooring throughout- Fully equipped kitchen with granite countertops and stainless steel appliances – stove, oven, microwave, dishwasher, refrigerator, coffeemaker, toaster, cookware and tableware- 1 King bed- Double Sofa...
Regency Waikiki Partial Ocean View 2 Bedroom
Unwind in your spacious two-bedroom condo, just a block from Waikiki Beach, restaurants, and shopping. Designed for up to six guests, it features a fully equipped kitchen, two cozy queen beds, and a comfortable sofa bed in the living room.• Kitchen includes ceramic...
New! Maui Banyan G105 – Heart of Kihei
Maui Banyan G105 – Ground-Level Comfort Near the Pool in South Kihei!Welcome to your perfect Maui retreat! Located in the desirable Maui Banyan Resort, this ground-floor 1-bedroom, 2-bath condo offers comfort, convenience, and a fantastic South Kihei location—just...
Maui Kam J209: Your Tropical Oasis in Maui
Escape to this spacious 2-bedroom, 2-bathroom loft condo at Maui Kamaole J209. Featuring an open living area, large primary bedroom with King bed, and a guest room with a Queen and a Twin bed, this condo comfortably sleeps up to 6 guests. Enjoy the lush tropical gardens...
Maui Resort Rentals: Honua Kai Hokulani 223 - Luxurious Studio w/ Lush Courtyard and Partial Ocean Views
Uniquely located, adjacent and with direct access to one of the largest ocean and island view lanais in all of Honua Kai. This unusually spacious Grand Lanai is only directly available to the residences on this floor, and offers guests an unparalleled lanai experience...
Renovated - Spacious 2BR/1BA Loft, AC, Close to beach
Our condo is conveniently located in South Kihei steps from the beautiful Kamaole I Beach Park and close to many shops and restaurants. Take in the beautiful views from your private lanai and watch the sunset.Our renovated 4th floor penthouse condo with floor to ceiling...
Kaanapali Alii | 156
Welcome to Kaanapali Alii 156, where luxury meets breathtaking views in an ultimate oceanfront corner location. This stunning condo offers expansive vistas of the beach, pools, tropical gardens, and the shimmering blue Pacific, making it a perfect retreat for those who...
Wailea Point | 2301 | 30+ Night Luxury Stays
Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, please select from one of our other beautiful Wailea resort properties.The finest development in the finest neighborhood on the finest Hawaiian...
Waikiki Shore 715 Ocean View Studio
Wake up to sweeping ocean views in this well-appointed studio, nestled in the only condo building on Waikiki Beach. With all the essentials and an unbeatable location, it’s the perfect home base for your island adventure.• Waikiki Shore address is: 2161 Kalia Road,...
Diamond Resorts The Point at Poipu - 2 Bedroom Partial Ocean View
*** Sanitation/Cleaning Update ***At Diamond Resorts, the safety and well-being of our guests and team members is of utmost concern. We remain diligent in our commitment to provide a safe, hospitable environment for all who visit our properties. Please read below for...
Watch Whales from your Bed - Double Master Sunset Suite
Inside your unit, discover a fully equipped kitchen, convenient washer and dryer units, cable television on a gigantic 75-inch Smart TV, private lanai, and sumptuous linens provided by 808 Maui Vacation Rentals. Immerse yourself in luxury and relaxation at Royal Mauian...
Royal Kahana Maui Garden View Studio
Garden View Studio- Open kitchen layout includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Air Conditioning- 1 king bed or 1 queen bed and a single sofa bed- 431 square feet/40 square...
Upgraded Oceanfront Terrace Condo - Private Beach Access!
D301 is an upgraded 2-bedroom oceanfront condo only a short walk away from the beach. Located in the world famous Mauna Lani Resort, the condo offers beautiful ocean and sunset views and a large outdoor lanai. The master bedroom has a king size bed and an en-suite...
Wai'ula'ula H102 - Wrap-around Lanai
This private, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with Sub-Zero, Fisher & Paykel and Wolf appliances/gas range and dual master suites. Additional features...
Pacific Sunset Paradise - Steps to beach and amenities
Welcome to your slice of paradise in Maui, Hawaii! Tired of crowded beaches? Say aloha to our this rental, just steps away from a white sandy beach off the beaten path. This beachside haven not only offers you the tranquility you crave but also puts you within flip-flop...