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.
Wyndham Ka Eo Kai | Four 2BR Suites - Sleeps 24!
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...
Fully renovated unit on the 14th Floor overlooking the surrounding Waikiki area!
1 Bedroom City View on the 14th Floor! Look no further, you've found PARADISE! This condo offers the comforts and conveniences of home. It is well maintained, reasonably priced and conveniently located in Waikiki. This updated condo has over 500 sq ft of living space...
Ocean View, Renovated Waikiki King Suite with 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...
Four Seasons Villa, Eternity Pool, Ocean Views!
*Inquiry only*Spanning over 3,500 square feet of luxurious interior space, this stunning retreat offers expansive outdoor living areas, a private pool and spa, and breathtaking panoramic ocean views.The bold and beautiful open-concept great room seamlessly extends...
Princeville Kauai 2 Bedroom Ocean View Oasis
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Perched high on the bluff above Hideaway Beach, this wonderful condo awaits you! Guests can delight in the front row ocean views and tropical breezes from this recently updated and...
Marriott Maui Ocean Club, Oceanfront 1 Bedroom Villa, 2 Bath 06/14/26-06/21/26
Experience the ultimate oceanfront Maui retreat at Maui Vacation Club – Lahaina Towers! Located directly on Ka’anapali Beach, this inviting 1-bedroom, 2-bath unit offers a serene escape with incredible resort perks.Your mornings begin with a Starbucks® conveniently...
Waialua Beachside Cottage: Lovely! Direct Beach 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.This stunning property is now accepting...
Westin Ka'anapali - Beautiful Resort On The Beach! Family Friendly! Island View!
The Westin Kā‘anapali Ocean Resort Villas South, located on Maui’s renowned Kā‘anapali Beach, offers an upscale island escape. These spacious villa-style accommodations feature kitchens, private lanais, and luxurious touches. Enjoy multiple pools, a spa, fitness...
Modern Elegant Studio w oceanviews..Royal Gardens
Elegant Studio at Royal Gardens Hotel Waikiki.....unit on the 20th floor offering panoramic views of Waikiki from mountain to ocean!Kitchenette is a plus for light preparation of meals promoting you to eat in.....Efficient and comfortable accommodations.Wyndham owners...
Westin Ka'anapali Ocean Resort Villas - OCEAN VIEW 1 Bedroom Villa
Luxury 1-Bedroom Ocean View Villa at Westin Ka’anapali Ocean ResortAvailability:7 nights from August 31 to September 7, 20257 nights from April 5 to April 12, 2026Enjoy a relaxing getaway at this stunning oceanfront resort on Maui’s west side, located on North...
Honua Kai Hokulani 305 Ocean View 2 Bedroom 2 Bath
- Exclusive on-site provider with the only homes meeting the prestigious AAA 4-Diamond designation- Perfectly located on the very sought-after inner courtyard overlooking the aquatic pools and breathtaking Pacific Ocean. - Spacious lanai (balcony) with outdoor dining...
Charming Puako ocean and sunset view retreat, w/d, expansive deck
New Listing Special!Welcome to your Big Island oasis at Puako Beach—just steps from world-class snorkeling, surf, and unforgettable sunsets. Enjoy ocean views, the soothing sound of waves, and a spacious lanai perfect for relaxing or dining al fresco. Expertly managed...
Remodeled 1 bedroom coastal stunner, AC, ocean & island views, resort amenities
Welcome to Royal Kahana 808. This beautifully remodeled coastal style 8th floor condo boasts expansive ocean and surrounding island views from multiple rooms. This condo can accommodate 4 people with its 1 bedroom and sofa sleeper. Stay cool year round with central AC...
Cozy Studio with Ocean Views, AC in Kahana
The Space:Notice - This home is in the HOTEL ZONE, so it will NOT be banned by the new law that will restrict short term rentals in the Apartment Zone.Welcome to our Kahana Studio, where you can enjoy views of Molokai and the Pacific Ocean!Our home is conveniently...
OAHU HAWAII OCEANFRONT HOME with POOL and BEAUTIFUL SUNSETS, WEST SIDE of ISLAND
NOTE: FOR SHORTER STAY PLEASE BOOK FOR 30 NIGHTS SO WE CAN DISCUSS RATE ADJUSTMENTS. (ADJUSTMENT WILL BE DRASTICALLY MADE)NOTE: OWNER/HOST CAN NOT SEE GUESTS CONTACT INFO UNTIL BOOKING IS MADE.NOTE: REMEMBER ANY BOOKING IS 100% REFUNDABLE IN FULL, INSURANCE AND ALL 14...
New Listing! Tranquil 1bd Condo with ocean views
Welcome to Kaanapali Shores Unit 733! This comfortable 1-bedroom, 1-bath condo is located on the 7th floor and can easily accommodate up to 4 guests. Stay cool with central air conditioning or step out onto your private lanai to enjoy the ocean breeze and relaxing views...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | 1-Bedroom Condo with Gourmet Kitchen! KGV-24T1
Luxury 1-bedroom, 2-story townhome in Kapalua with ocean views, Cal King bed, 2 lanais, full kitchen, 2 spa-style baths, and modern upgrades. Close to beaches, golf, and Maui's best sunsets.*Special Offer- Book any KBM rental home in Hawaii for 6 nights or more with an...
Kaanapali Alii | 481
Welcome to your perfect Maui retreat at this one-bedroom plus sleeping den residence in Kaanapali Alii, featuring partial ocean views that enhance your tropical experience. This spacious condo is designed for comfort and relaxation, accommodating up to four guests with...
Discovery Bay deluxe city view, near Ala Moana Shopping Center & the beach!
Welcome to your island escape in the sky! Located on the 24th floor of Discovery Bay, this beautifully renovated 1-bedroom, 1-bathroom condo offers 852 sq ft of comfortable living space and stunning views of Diamond Head, the city, and the lush mountains.Unit...
Magic Skies Koi Pond View Handicap Accessible Room
With double doors leading to a koi pond on the main level this koi pond themed room is quaint and comforting. The room is fully handicap accessible with 36" doors, has a king size bed, a sitting chair, bench, no steps, private bathroom with tiled walk-in shower with...
Waipouli Beach Resort E304 Ocean View 1 BD 2 BA
- 3rd floor condo with balconies- 898 square feet / 84 square meters- Maximum 4 persons including children and infants- 1 king bed, 1 queen sofa bed- Crib on request at no charge- Aerobeds on request at 15 USD per night- TV with cable channels and in living room -...
Westin Kaanapali Ocean Resort Full Resort Access Studio ocean OR island view
Westin Kaanapali Ocean Resort Villas provides the ultimate in pampering and relaxation.The units I list are managed and maintained by the Marriott resort. Guests will check-in at the resort’s front desk using their resort confirmation number and guest name....
Ground Floor Maui Sunset B105 on the oceanfront in Kihei
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot patio. Ground floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck and renovated interior. Doesn't get any better....
Marriott's Kauai Beach Club, 1 Bedroom/2 Bathroom, Free Wi-Fi
ACCOMMODATIONSOne king bed or 2 double beds, 1 wall bed (not a traditional bed)Two Full BathroomsGENERAL AMENITIESMaking your home-away-from-home comfortableAlarm clockIron/ironing boardPillows: FoamKITCHENETTE AMENITIES3/4 size refrigeratorDishwasherMicrowave (no oven...
Royal Kahana Maui 504 Ocean View Studio
- 5th floor condo with balcony on the north side of the building- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea-...
Hale Maia at Kukui ula - Elegant Pool Retreat with Golf Views in Poipu
Summary:TA-101-738-2400-01Discover Hale Maia at Kukuiʻula, a stylish and spacious 5BR, 5.5BA home in Kauai’s most exclusive community. This modern retreat features panoramic fairway views, a private heated pool, and seamless indoor-outdoor living. With each bedroom...
Westin Kā‘anapali Ocean Resort North - 1 BR
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour...
The Westin Nanea Ocean Villas | 1BR Premium Villa
Summary:The Westin Nanea Ocean Villas maintains is situated on 16 acres of Maui's North Kā'anapali Beach and is designed to provide a relaxing haven replete with culturally inspired programs and authentic Hawaiian experiences. Depart from The Westin for a close...
2 Oceanview Luxury Suites+ pool and Jacuzzi
Stay with us at this 2 Suite luxury estate with a spectacular ocean view.The home is composed of 2 suites, each with 2 bedrooms each (4 total bedrooms in the rental)! There are 2 enormous gourmet Kitchens/2 Living Rooms/2 Dining Rooms, along with 2 laundry rooms! All...
Experience Tropical Bliss at Hyatt Vacation Club at Ka'anapali Beach Resort-2 Bd
Looking for the perfect family-friendly island getaway? Hyatt Vacation Club at Ka'anapali Beach offers the ultimate blend of luxury, adventure, and relaxation on the world-famous shores of Maui. Nestled along the stunning Ka'anapali Beach, this resort is your gateway to...
Marriott's Waikoloa Ocean Club | Two-Bedroom Villa
Summary:Experience the lush beauty of Hawaii's big island at Marriott's Waikoloa Ocean Club Resort. Located on the pristine sands of the Waikoloa Beach, this resort is what dreams are made of! Enjoy a day at the resort swimming in the pool, playing at the beach, booking...
Waipouli Beach Resort A106 Ocean Front 2BD 3 BA
- Extra-large floor plan featuring 2 master bedrooms and 2 balconies on ground floor with private patio- Located just steps from the beach and near the pool- Condo offers full kitchen to include granite countertops and Wolf cooktop, convection oven, microwave, 2-drawer...
Charming 3-bedroom home in Hilo town
Stay comfortably in this 3-bedroom house centrally located in Hilo town. The bedrooms feature a king bed, queen bed, two full beds, and a twin bed, ensuring a good night's sleep for all guests. With two bathrooms equipped with showers and a cozy living room with two...
3BR/2BA New Build | Pool | W/D | Garage | Park
Welcome to this brand-new home: a spacious 3-bed, 2-bath, 1600 sqft retreat perfect for guests seeking ample space and a peaceful, safe neighborhood. Enjoy an open-concept living area with vaulted ceilings, extending to a covered lanai. The modern kitchen boasts sleek...
*Spacious Getaway Near Beach & Golf* | 1st Floor
Summary:🌴 Experience island perfection in this beautifully furnished, single-level 2 bedrooms /2 bathrooms retreat at the end of a peaceful cul-de-sac in Princeville. Vaulted ceilings and wall-to-wall sliders fill the space with 🌞 natural light. Step out onto not...
Wyndham Bali Hai | 3BR Suite with Resort Access
Summary:Wyndham Bali Hai Villas | 3BR/3BA Balc King Suite• Size: 1459 - 1459• Kitchen: Full• Baths: 3• Accommodates: 8 Guests• Beds: King Bed - 2 VariesThe Space:Room Amenities• Pack ’n Play/travel crib available upon request• Ceiling Fan• Hairdryer•...
Oceanfront Villa! Westin Ka'anapali - Beautiful Resort On The Beach! Family Friendly!
The Westin Kā‘anapali Ocean Resort Villas South, located on Maui’s renowned Kā‘anapali Beach, offers an upscale island escape. These spacious villa-style accommodations feature kitchens, private lanais, and luxurious touches. Enjoy multiple pools, a spa, fitness...
Beachfront Condo in Kihei!
Kick back and relax in this calm, stylish space. This condo features an upgraded interior that provides a comfortable and enjoyable stay. It is ideally located for easy access to the airport and nearby attractions, perfect for exploring the area. The condo is...
KBM Resorts | FREE CAR | Papakea | 1-Bedroom Condo with Beach Access! PKD-104
Charming ground-floor Papakea condo with A/C, modern kitchen, private lanai, resort pools, tennis, pickleball, and lush landscaping. Steps to beaches, dining, shopping-perfect Maui escape.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an...
Central Waikiki Location with Rooftop Pool & Dining Within Walking Distance
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, TV, ensuring cleanliness and comfort throughout your stay.✦ Daily...
The Whaler Resort - 314 - Garden View Studio
Garden View Studio featuring a king size bed, fully equipped kitchen, dining area and private balcony. The unit is over 500 square feet and has all the amenities needed for your vacation in paradise. The spacious unit is conveniently located steps from Ka'anapali Beach...
Beachfront Home
Get away from the hustle and bustle of Waikiki and come to the Windward side of Oahu.Please note:-There's a third, 2 tenant-occupied unit onsite. The tenants do not access the lanai area unless absolutely necessary. -Absolutely no unregistered guests are allowed on the...
Ocean Front Condo, Modern & Bright
Location is key for our newly renovated 1 bedroom sunny South Kihei unit. Watch spectacular sunsets and whale watch from the comfort of your second story lanai. Experience island life at its best! Shopping, dining, surf lessons, and great beaches are all within walking...
The Westin Nanea Ocean Villa | Three-Bedroom Villa
Summary:The Westin Nanea Ocean Villas maintains is situated on 16 acres of Maui's North Kā'anapali Beach and is designed to provide a relaxing haven replete with culturally inspired programs and authentic Hawaiian experiences. Depart from The Westin for a close...
Family-Friendly Room! Pool View, Full Kitchen! Near Waikiki Attraction!
Discover a serene oasis just steps from the iconic Waikiki Beach, where tranquility meets excitement. Enjoy breathtaking views of Fort DeRussy Park while indulging in local activities like lei-making classes and wine nights. Explore nearby treasures such as the Royal...
Oceanview updated condo w/AC on a 6 mile stretch of sandy beach
Welcome to Nani Kai Hale 305. Enjoy an ocean view from your private lanai. Feel right at home in this updated condo with everything from split AC in both the living room and bedroom, sofa sleeper, fully equipped kitchen, beach gear, & essentials. This condo can...
Luxury fantastic ocean view huge private pool/spa, central AC, walk to the beach
This luxurious, beautiful, and amazing ocean view retreat is located within walking distance to beaches, just 10 minutes from downtown Kona, which offers many shops, restaurants, the farmers market, the pier, and beaches. The airport is only 20 minutes...
Wyndham Ka Eo Kai | Four 2BR Suites - Sleeps 24!
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...
Royal Kahana Maui 203 Garden View Studio
- 2nd floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry, kitchen and bathroom;...
Royal Kahana Maui 1005 Ocean View Studio
- 10th floor condo with balcony on north side of building- Updated kitchen with granite counter – fridge, stove/oven, microwave, cookware, tableware- Bathroom with walk-in tile shower and granite vanity- 1 king bed and 1 twin sofa bed- 431 Square feet / 40 Square...