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.
Steps to Beach! 2 King Beds and Extremely Walkable!
Listing SummarySteps from Lipoa Beach and walkable to shops, dining, and coffee, this bright, spacious condo is perfect for families, couples, or small groups.The condo is ideal for up to 6 guests, but can accommodate up to 8 using twin trundle beds (one in each...
Alii Villas#320 Fully Remodeled Top Floor End unit w/ Incredible Ocean Views
Welcome to your slice of paradise! This beautifully remodeled top-floor end unit at the highly sought-after Alii Villas offers the perfect blend of comfort, style, and breathtaking scenery. Enjoy panoramic ocean and sunset views right from your private lanai—ideal for...
Walk to the Beach! Modern 3Bed, 2Bath w/ AC, 1 Free Parking, and More!
Aloha from Waikiki! Thank you for considering our short-term vacation rental company. We are pleased to offer you Kuhio at Waikiki, a newly remodeled minimalist-style unit in the heart of Waikiki. Our location is just two blocks from the famous Waikiki Beach, providing...
2 Bedroom Condo-Princeville, Kauai-Family Friendly!
Perched above the sparkling waters of Hanalei Bay, this resort offers families a front-row seat to some of Princeville’s most awe-inspiring natural beauty—from the dramatic Na Pali Cliffs and iconic Bali Hai Mountain to cascading waterfalls, golden beaches, and palm...
Spacious Studio with AC and WiFi, Just One Block from Waikiki Beach
Just one block from Waikiki Beach! Located on the Diamond Head side of Waikiki, this spacious studio offers two queen beds, a full kitchen, bathroom, AC, a 65" flat-screen TV and high-speed Wifi. Beach amenities included: snorkel gear, sand toys, beach umbrella, towels,...
New Listing! Bedroom with private lanai access
Welcome to Nohonani 103, your newly refurbished oceanfront escape in West Maui! This inviting ground-floor, 1-bedroom, 1-bath condo offers all the comforts of home with unbeatable access to the beach—just steps from your private lanai. With space to accommodate up to 4...
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...
Tropical Garden Condo with AC and pool
Spacious, ground floor condo on the famous north shore - Princeville. 2 bedroom / 2 bath, 1500 sq feet. Lush, tropical landscaping! Huge private wrap-around lanai with lush landscaping, 4 sliders & walls of glass. Mauna Kai has the largest pool in the area! Grill on...
Spacious 5-Bedroom Oceanview House in Holualoa
This prime location has views of the ocean and coastline while being adjacent to a forest reserve. The custom 2-level home offers 5 bedrooms and 4.5 bathrooms, a cool elevation, and lush green areas. The home is equipped with air conditioning and a dehumidifier in each...
Wailua Bay View 107 Oceanfront condo
This 1-bedroom condo in Kapaʻa is perfect for your escape to paradise. With WiFi, and a washing machine, guests can enjoy a fantastic stay in this wonderful space. The pleasant atmosphere and convenient amenities make it a great choice for a relaxing getaway. Fall in...
Makaha Mountain Hideaway
The spacePlenty of drawers and cabinets for ample storage for all your travel items. Walk-in closet with storage. I have provided all the basic necessities to start your vacation comfortably upon arrival.Guest accessThe entire property inside and out are available to...
Kalo Homes - Makaha Modern
Welcome to your slice of paradise in Makaha.This spacious 4-bedroom home on Oʻahu’s west side offers the perfect mix of comfort, nature, and authentic local living. It’s ideal for families, multi-generational groups, or friends traveling together.Step outside and enjoy...
My Perfect Stays: New Listing Special
Maui Eldorado E106 is a studio condo that comfortably accommodates up to four guests, featuring a king bed and a queen sofa bed. Enjoy lush garden views and just 5 steps to a small pool—perfect for a relaxing island getaway.Savor your meals al fresco on the ground-floor...
Gorgeous Home on Landscaped Acre-2BR/2BA
Welcome to Pua Lani, a gated one acre estate two blocks from the ocean that features resort landscaping and large lawn areas that create a very private and serene setting for your stay. The two story home features 2 bedrooms and 2 baths along with a large high ceilinged...
BRAND NEW LISTING DISCOUNT-Amazing Ocean Views-heated pool-location-AC
Spacious & Updated 3rd Floor Condo with Ocean Views and Vibes Welcome to your home away from home at Royal Kahana, Unit 312, located in Kahana, MauiA beautifully refreshed condo designed for comfort, convenience, and relaxation.Inside the Condo:Private balcony on the...
Beautifully Renovated with Parking, Steps to Waikiki Beach!
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...
Modern Charm: Renovated 1BR, fast 600Mbps Wifi, W/D in unit, Stunning Views
Welcome to your island paradise! Soak in floor-to-ceiling mountain views with your morning cup of coffee; at night, savor the vista of twinkling city lights. You’ll love whipping up homecooked meals with the full kitchen, working comfortably with the remote work setup,...
New Listing! Beautifully remodeled!
The Kona Makai complex is right on the beautiful Kona coast! Kona Makai provides an ocean-side swimming pool, hot tub, minimal fitness center, ping-pong table, cabana, gas bbq areas, tennis courts, and complimentary parking. Kona Makai also has direct access to the...
Aloha Suite Near the Sea IV, 3 Block Walk to Beach
TMK260230500082, TA-166-694-5024, STR# 2667 Convenience & Location! Just 3 SHORT BLOCKS TO WAIKIKI BEACH! Enjoy the ocean with gorgeous sunsets day after day. Fun shopping, great restaurants & entertainment all around you!3 Additional studio suites available same...
🌴Luxurious Oceanfront Home on Golf Course – Paradise Awaits – Golf Package Available🌴
Set right on the golf course and ocean, this coastal style residence provides an idyllic setting for your ultimate Hawaii vacation. The 3 bed, 2.5 bath, 1,887 sq. ft. home rests along Kona Country Club's ocean course, where waves collide with the rugged coast and...
EXTRAORDINARY Hale Kuikahi Oceanfront Retreat - fully airconditioned!
Step onto the grounds of our oceanfront botanical garden retreat - Hale Kuikahi! Located in the quiet Paukaa area of Hilo just above famed Honolii surf beach, Hale Kuikahi boasts a private botanical garden walk onsite. Enjoy sweeping oceanfront views from almost every...
Absolute Oceanfront Gorgeous views 2-bedroom house with Air Conditioning!
Marvelous 2-bedroom 2-bath oceanfront estate on ancient lava cliffs and black sands with the most incredible wrap around ocean views on the island! The views make it feel more like you are living on a luxury yacht than a house. This tranquil retreat was designed by a...
Gorgeous 5th Floor 2 Bedroom Condo. - Kihei Surfside #501
Kihei Surfside #501 – Top-Floor Oceanfront Views and Tranquility in a Rare 2-Bedroom LayoutWelcome to Kihei Surfside #501, a rare and spacious 2-bedroom, 2-bathroom oceanfront condo perched on the top floor of one of South Maui’s most sought-after properties. With...
New Listing! Studio with direct ocean views
Mahana 913 is a beautifully updated studio condo that offers stunning, unobstructed oceanfront views and a serene, relaxing atmosphere. Perfect for a romantic getaway or solo retreat, this bright and airy space accommodates up to three guests and features a plush...
New Listing! Tropical-themed 7th floor studio
Kaanapali Shores 721 is a Studio condo with central air conditioning that can accommodate up to 3 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...
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...
New! Luxury Split-Level Retreat at Pili Mai 15E
Luxury Split-Level Retreat at Pili Mai #15E | Poipu ParadiseProperty OverviewWelcome to this stunning split-level home at the prestigious Pili Mai Resort in sun-soaked Poipu, Kauai. This immaculately maintained 3-bedroom residence offers the perfect blend of Hawaiian...
Sea Village Oceanfront ground floor unit
NEW TO THE VACATION RENTAL MARKET. Wonderful direct ground floor 2 bedroom/ 2 bath oceanfront condo with sweeping views of Kailua Bay and lots of ocean activity. Beautifully updated unit with everything you need for a great Hawaiian getaway. Note, this unit does not...
Beautiful Maui Condo Steps from the Beach in Kihei!
Live like a local during your stay at Kihei Bay Vista unit D110!This ground floor unit features a large lanai overlooking the tropical green lawn, mere moments from the sparkling shore!Our private oasis provides you a home away from home with a king sized bed, full...
New Listing! Modern Ocean-View Condo at Luana Kai C203
New Listing! Modern Ocean-View Condo at Luana Kai C203.Interior photos coming soon.Welcome to Luana Kai #C-203, your Maui home away from home! This beautifully updated 1-bedroom, 1-bath condo offers modern comfort, stunning views, and an unbeatable location on the...
Charming apartment in delightful Koloa with fitness room, AC, WiFi
This amazing apartment in Koloa is a hidden gem waiting to be discovered by guests.Charming, newly updated condo with AC, just steps from the ocean. Blending historic Hawaiian plantation style with modern comforts, this serene retreat is perfect for families,...
Pacific Shores B309: Ocean Views & Comfort in Maui
Experience paradise at Pacific Shores B309, where breathtaking ocean and sunset views meet comfort and convenience on the stunning island of Maui. This 2-bedroom, 2-bathroom condo features plush queen beds in both bedrooms, with ceiling fans and screened windows that...
Family Friendly Condo in Princeville with sparkling Pool-Jacuzzi and BBQ's
Reconnect with loved ones in this family-friendly place. This amazing condo, right across the street from the Makai Golf Course, has an adjoining door, one unit has a master bedroom with a king bed, and a loft with 2 full beds plus a sectional couch that is comfortable...
Newly renovated condo with multiple lanais, A/C, heated saltwater pool & tennis
Banyan Harbor I-101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Banyan Harbor, your perfect getaway in Lihue, HI! This beautifully remodeled condo offers stunning ocean...
Modern 3Bed, 2Bath Walking Distance to Beach! AC, 1 Free Parking, and More!
Aloha from Waikiki! Thank you for considering our short-term vacation rental company. We are pleased to offer you Kuhio at Waikiki, a newly remodeled minimalist-style unit in the heart of Waikiki. Our location is just two blocks from the famous Waikiki Beach, providing...
Pohailani Paradise, AC, Ocean Views, Sunsets
Wake up to breathtaking ocean views with Molokai and Lanai on the horizon. From the lanai, watch sailboats glide, sea turtles swim, and whales breach in the distance (during whale season). Golden beaches, swaying palms, and vibrant rainbows create a picture-perfect...
Lovely 1-bedroom condo w/beach view, mountain views, WiFi, AC & FREE Parking
Waikiki is waiting for you at this amazing 1-bedroom condo. The lovely 1 bedroom features two queen beds and full kitchen. Enjoy the excellent amenities like AC, WiFi, TV, and full kitchen. The living room offers an additional space with a twin daybed with two twin size...
Turtle Paradise - King bed - Maui Vista/steps to beach, free parking, WiFi, AC
Congratulations - You have found your perfect next getaway location. This is an owner-managed unit so no hassle or frustration from third-parties! Attention to detail and personal support are first-class when you stay with us!! Come visit one of the best beaches in all...
Stunning Ocean-View Retreat Overlooking Laupahoehoe Point
Welcome to your tropical escape! This stunning three-level home boasts panoramic ocean views and a tranquil setting, making it ideal for a peaceful and rejuvenating vacation.With 1,500 square feet of space, the main living areas are located on the upper level, while the...
Maui Kamaole A-206 - Prime Location, Stunning Renovation, Large Lanai, Split AC!
Welcome to Maui Kamaole A-206, a stunning 2-bedroom condo nestled in the heart of South Kihei, Hawaii. This beautifully appointed retreat offers a perfect blend of comfort and style, making it an ideal getaway for families or couples seeking a slice of paradise.With a...
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...
Beachy Kona Getaway. Located within walking distance to the heart of Kona Town.
Welcome to our dreamy Kona getaway! This newly refurbished, luxury beachy retreat is designed for relaxation and convenience in the heart of Kailua Kona. Walking distance from Kona`s best restaurants and bars, it provides easy access to Ali`i Drive and all it offers,...
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Nestled just a 30-second walk from the beach and three popular surf breaks, this beautifully remodeled 3-bedroom, 3-bathroom townhome in Puamana offers the perfect blend of modern comfort and laid-back island living. Located on the safe side of Puamana, untouched by the...
Maui Kā’anapali Villas 291: 1-bedroom condo located ocean side
Maui Kā’anapali Villas 291: 1-bedroom condo located ocean side in the Emerald building, overlooking the Pool, with partial Ocean views.The space:This one-bedroom condominium is located in the popular Emerald building, renowned for stunning views of the pool, grounds,...
Charming 1 bdr in LAIE Private yard and entrance! 5 minute walk to Hukilau beach
Located in a prime spot in Laie. 5 minute walk to famous Hukilau beach. Message if you have any questions. One bedroom attached unit with living room, kitchenette and full bathroom. Private yard and entrance. The whole group will enjoy easy access to everything from...
NEW Luxury OCEAN & SUNSET View with Huge Wrap Around Lanai and GOLF DISCOUNTS
Newly Listed Luxurious XL Ground Floor Hawaiian Condo with Stunning Sunset Views, overlooking the 3rd hole of the Waikoloa Beach Nine at Kings Golf Course. Enjoy huge golf discounts as Guests of Gold Members. Escape to your dream vacation at our beautifully appointed...
Adorable 1-bedroom condo with kitchen, pool, WiFi near Waikiki Beach, sleeps 6-8
Adorable newly upgraded condo with full kitchen, WiFi, AC and pool in the center of Waikīkī just blocks from Waikiki Beach and International Marketplace filled with famous art galleries restaurants and high end fashion! Furnished with a queen bed, king bed, 2 twins...
New Listing:Tall ceilings, ocean views, and more!
Ekolu 404 is a spacious 2-bedroom, 2-bathroom second-floor condo, perfect for up to 6 guests. It features three private lanais, air-conditioning, and a washer/dryer. The master bedroom and guestroom both have king beds, while the living area offers a queen sleeper sofa....
Hale Konane – Oceanview Luxury at Mauna Lani Resort
Hale Konane blends Big Island elegance with relaxed island living in the heart of Mauna Lani Resort. Set along the 17th green of the South Course, this 5-bedroom, 5-bathroom single-level estate offers sweeping golf and ocean vistas, refined interiors, an outdoor retreat...
Aston at the Whaler on Kaanapali Beach 964
Stunning ocean views are the highlight of this beautifully remodeled studio located on the 9th floor of Tower 2 at the Whaler on Kaanapali Beach. This studio condo has a King bed and central air conditioning. The living area features a large flat-screen TV and a comfy...