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.
Escape to Paradise at the Maui Vista "3rd Bld 1b/1b"
Maui Vista Resort is South Maui's Best Value, offering 1 and 2 bedroom condos. Consisting of 3 buildings, pools, tennis courts, and BBQ areas at each building. This complex is in prime location to everything in Kihei located across from famous Kamaole 1 and Charley...
HK 322 Luxurious Kaanapali BeachFront 2BD w Pool AC
Honua Kai 322 Luxury Resort Honua Kai 2Bedroom in Kaanapali, Maui FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm...
Updated Wailea Condo in Oceanfront Complex!
Enjoy your open and airy living area with breathtaking views of the picturesque foliage through your lanai door in unit 52A! Ample seating available as the dining table for four and two seats at the bar area provide comfort and relaxation as you entertain family and...
Maui Sunset Vacation Rentals B207
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. New flooring throughout 2023. Easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck and renovated interior....
Waikiki Moana Inn
Location, Location, Location. Relax to the gorgeous views of flowing canal waters, or walk to the beach. It's at your fingertips. Built for your comfort, and located for your convenience. Experience windows wrapped around the new corner unit on the 18th floor. 2...
Charming home with balcony, washer/dryer & free WiFi – stunning ocean views
Waipio Glass HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Unwinding into vacation mode is easy at this ocean-view home! Feel the breeze through the palm trees as you lounge...
Tropical Ocean View! Escape to the Rainforest getaway of your dreams!
We are pleased to now offer THE HOUSE OF THE FULL MOON on VRBO!!!Indulge in the serenity that will be yours as you sleep with the sound of singing frogs and crashing waves. Awaken to birds chirping and warm, tropical breezes. Appointed with everything you need in a...
🌴 Very Comfortable and Spacious Townhome in a Resort Like Community🌴
Enjoy a free late checkout on bookings made before December 15th 2025!This bright and spacious townhome offers quiet island living and resort-style amenities a mile from Kahaluu Beach and Kona Country Club. Your 1,778 square-foot townhouse has an open floor plan for...
Partial Ocean View W/Private Lanai-Kamaole Sands
Kamaole Sands unit #10-201: This charming unit provides the space and design allows you and your family or friends plenty of room to relax among the modern décor and high-quality finishes. Cooling flooring, ceiling fans, and a wall AC unit will keep you comfortable...
Lae Nani 123 Ocean and Pool Penthouse
Paradise Found! Oceanfront Resort Lae Nani - Penthouse Ocean and Pool View Unit 123! NEW AC! The Best of the Best! From the moment you walk in you will know you made the best choice! This Royal Hawaiian Penthouse Ocean and Pool View Condo has a Stunning Ocean View with...
Hana Garden Room 1 & 2 night stays, its Perfect! Longer stays available.
Hana Maui1 & 2 Night Staysit's PerfectOn 4 acres of tropical gardens/farmland for you to enjoy during your stay. A very friendly 100 lb dog and 9lb cat. Both will approach you for affection. When You Want To Explore Hana For More Than An Afternoon, Enjoy a 1 or 2 Night...
North Shore 2-Story Rustic Yurt Glamping Lodge Tropical Nature Rental Near Beach
Tropical North Shore Island Nature Retreat! 2.5 blocks to the beach & famous surf breaks. Close to historic Haleiwa town & many other gorgeous North Shore beaches & world-class surfing!Rental is a 2-Story Yurt with a generous 1500+ square foot open-concept floor plan....
Diamond Head Ocean Views! Parking/Wifi included
Panoramic views of Diamond Head Crater and the ocean is the WOW factor to this unit on the 31st floor in the Royal Kuhio!Newly upgraded bathroom to a “luxury 5 star spa”. Also the unit has “washer/dryer combination”.The spaceOpen floor plan featuring a "pocket...
Waikomo Stream 402 - Private, Peaceful, Garden View Condo With 2 Lanais
This charming one-bedroom, plantation-style condo is a tropical retreat in sunny Poipu on the garden island of Kauai. Located near many of Hawaii's best beaches, restaurants and shopping, come stay and relax in paradise.Indulge in the charming ambiance of this recently...
Spacious house with private gas grill, shared pool, close to golf
The H-HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The award winning "H House", designed by George Heneghan, is truly one of Waikoloa's finest architectural specimens. In the...
Discounts! Experience WaikaloAloha! Cozy. Comfy. Convenient. Views.
The Hawaiian term ‘aloha’ runs deeper than a word of salutation. Over many years of visits to the Big Island, we are grateful to have experienced aloha: kindness, mutual regard, warmth in caring. Now, with our renovated condo in Waikoloa Village, we are eager to...
Golf course adjacent condo with heated pool, hot tub, fitness room, tennis
Fairway Terrace G101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pack up your clubs and make your way to this golf course adjacent condo where you'll also enjoy access to a host...
Beach Condo by the Shared Pool w/ Free WiFi, a Full Kitchen, & Furnished Patio
Kihei Kai Nani 120Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next beach getaway awaits at this ground-floor, tropical-themed condo located just steps from the resort pool...
Beautiful home with great room, lanai & private hot tub - walk to Anini Beach
Blue Hawaii HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located on a quiet cul-de-sac, this magnificent, custom home was built in 2008 by a contractor for his personal...
Spacious 2 bedroom Villa with large loft over Pool and Abay with amazing sunsets
Located in the beautiful resort of Waikoloa Beach near Marriott and the Hilton hotel in the Kohala Coast is a beautifully furnished 2 bedroom condo with 2 full bathrooms along with a 2nd level loft that can serve as the 3rd bedroom if necessary. The condo overlooks the...
OCEANFRONT RESORT, 2BDRM, fresh towel changes, WIFI, wshr/dryr, pool, bar&grill
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM, 2 BATHROOM (King in master and 2 Twins or we can request a Queen for the 2nd bedroom), OCEANFRONT RESORT, short walk to...
Princeville Paradise Studio @ 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...
Stylish condo just a short stroll from top beaches
Welcome to Pacific Shores B110, a delightful 2-bedroom, 1-bathroom ground-floor condo that can accommodate up to 4 guests. As you step inside, you'll be greeted by an inviting open-concept living space. The living room, designed for both relaxation and entertainment,...
Elegant 2bd golf course villa with vast Maui views
E Komo Mai "welcome” to Kapalua Golf Villa 23T 6&7! This luxurious 2-bedroom, 2-bath condo can accommodate up to 6 guests and is located right on the Kapalua Bay Course. Step inside to enjoy the bright and airy main living space that features a Queen sleeper sofa with...
Oceanfront Escape: Kihei Surfside #211 – W/ Gorgeous Views & Groundsnnn
Kihei Surfside #211 – Stylish Remodel with Ocean Views, A/C, and Spacious LivingKihei Surfside #211 is a beautifully remodeled one-bedroom, one-and-a-half-bathroom condo offering a seamless blend of modern upgrades and oceanfront serenity. Perfectly positioned on the...
KV E601 Updated Condo AC Pool Sunset Views Near Beach
Kahana Villa E601 Beautifully Decorated Air-conditioned Condo with Stunning Sunset View FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca...
Sunny Hawaii BeachFront Property
Welcome to Paradise! Enjoy 180 degree ocean view from the Diamond head to Sunsets. From the 1sr floor you will see the endless views of the Pacific Ocean. Leave the windows open and sleep to soothing crashing waves just a few feet from you and enjoy the cool ocean...
2bed/2bath Penthouse Ocean View...upgraded
Summary:My place is close to restaurants, shops and transportation. The Hawaiian Monarch Hotel is conveniently located near the main strip of Kalakaua Ave and the Hilton Hawaiian Village is 15 minutes away with the Waikiki Beach fronting the Hilton.Nearby popular places...
9th-Floor Mountain View Suite and Expansive Lanai at Honua Kai
This condo is zoned hotel and is in legal compliance with all Maui County ordinances.Ninth-Floor Mountain View Suite and Expansive Lanai at Honua KaiE komo mai (welcome) to Kai Mauna (“The Mountain Sea”), where the tranquil beauty of the West Maui Mountains meets...
Maui Resort Rentals: Honua Kai Hokulani 640 - Luxurious 1BR w/ Partial Ocean & Mountain Views!
Hokulani 640 is a luxurious one bedroom suite that offers views of the tranquil blue Pacific Ocean as well as views of the lush West Maui Mountains. You will have plenty of space to relax in the 700 sq. ft. interior. To fully enjoy the warm Hawaiian breeze, fold away...
Magnificent 2BR Condo with Outdoor Pool and Stunning View
Experience the very best of the North Shore at this upgraded private & spacious condo in Princeville. This luxe island style retreat is located near all the attractions the infamous Garden Island offers. Enjoy the pool or take a stroll down to Anini or one of the many...
Enjoy Multiple Private Lanais W/AC–Kanaloa at Kona
Kanaloa at Kona unit #406: One look inside this massive two-bedroom/two-bathroom tropical-themed vacation retreat and you’ll see why it’s a favorite. This retreat has chic island décor with attractive furniture and modern touches that provide a comforting...
Cheerful, Classic Hawaiian Retreat w/ Incredible Views & Updated Kitchen/Bath
Located on the seaside cliffs of Kauai’s beautiful North Shore, Ali'i Kai 4303 is a comfortable, top-floor retreat with the most incredible ocean views in every room! It's truly a whale watcher's dream come true. Inside you'll find two attractive bedrooms, each with...
Maui Vista 1310: Beautifully Renovated 1 Br condo with Partial Ocean Views
Beautifully Renovated one-bedroom condo with partial ocean views. This unit sleeps up to four people with a queen bed in the bedroom and a pull out sofa bed in the living room. The kitchen has been renovated with all new granite countertops, white appliances, cabinetry,...
Kona Paradise - Stunning Ocean Views from Lanai - Captain Cook, Hawaii
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
OCEANFRONT Condo with Incredible Views - Maui Kai 805
Oceanfront Maui Kai 1 bedroom, 1 bath on North Kaanapali BeachWalk to restaurants and storesHeated Swimming Pool & Jacuzzi with BBQ AreaACFree parking and NO Resort Fees!Beautifully renovated one bedroom/one bathroom oceanfront condo boasts unobstructed, 180 degree...
Newly Remodeled, 27th Floor, 1 Bed 1 Bath Deluxe Ocean View, Free Parking & Wifi
Deluxe Ocean View Unit 2714 Tower 2 Unit, Free Parking & Wifi - 2019 Brand New RemodelThe pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck renovation project. Enjoy...
Pacific Views w/Private Lanai – Kaha Lani 208
Castle Kaha Lani Resort #208 - Stylish Island living defines this 739-sf condo with lanai off the living area and master bedroom. Replay the day overlooking expansive lawns, heated pool and gorgeous Pacific. Homey perks include a full kitchen for meal ease, WiFi, flat...
Poipu Sands Beach Villa
Experience Paradise Living: Your Dream Hawaiian Getaway Awaits!🌴 Welcome to your own slice of Hawaiian paradise at Poipu Sands! 🌴Nestled on the stunning shores of Kauai's Poipu Beach, this exquisite three-bedroom, three-bathroom condo offers the ultimate island...
Waikiki Condo | Sleeps 6 + Pool Access
Nestled in the heart of Waikiki, this 2-bedroom, 1-bath condo is the perfect island retreat. Enjoy a fully equipped kitchen, a private balcony with outdoor seating, and vibrant tropical decor. Just steps from shopping, dining, and Waikiki Beach, this cozy getaway offers...
Sugar Beach Resort Condo w/ Ocean View, Shared Pool/Hot tub-Swim, Surf, and More
Sugar Beach Resort 116Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Maui Sunset B302, 1 BR, 2 BA, Partial Ocean Views!
One bedroom, two bath partial ocean view third floor condo. Full kitchen, washer / dryer, air conditioning in living room and bedroom, sofa sleeper, and a queen bed in Master. A couple of minutes away from Kamaole Beach I, II & III which are some of the great beaches on...
Oceanfront updated 2 bedroom/2bath condo on 6 mile beach
Welcome to Kihei Beach Resort 301. This 3rd floor 2 bedroom 2 bathroom condo is ready to be your Maui home away from home. Beautifully updated & perfectly located on the sandy six mile stretch known as Sugar Beach. This condo accommodates 6 people and features central...
Punahele A301: Panoramic views, 3 BED, 3 BATH, open living areas + ocean vistas
Welcome to Keauhou Punahele, A301! Located in Keauhou with great views of the golf course and the ocean. This three-bedroom, three-bathroom condo has an open layout of the living area and lanai. Amenities include televisions, high-speed internet, and more.Enjoy your...
Lovely oceanfront condo with view, hot tub & pool
Kona Bali Kai #403Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Homey comforts abound in this oceanfront condo with a private lanai with sweeping ocean views, perfect for enjoying...
Luxury, upgraded Waikomo Streams condo with pool - walk to Poipu Beach
Waikomo Stream Villas 322Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find island-inspired luxury, every modern comfort, and a gorgeous tropical setting at this beautifully...
Maui Resort Rentals: Honua Kai Hokulani 613 - Premier 6th Floor Interior Courtyard 1BR w/ Stunning Ocean Views!
Boasting an incredible 6th-floor location in the only column of interior courtyard 1br suites at the Honua Kai Resort, Hokulani 613 is simply one of the best. Enjoy gorgeous Pacific Ocean and Molokai views from this incredible 1br vantage point.The kitchen is fully...
ILIKAI 2BR/2BA ISLAND STYLE CITY VIEW APARTMENT. OCEAN FRONT PROPERTY.
Island style nice property. It has 2 bedrooms and 2 bathrooms and it can accommodate up to 6 guests! Unit has two balconies, two TV's. Hotel itself has two pools, breakfast place, coffe shop and it is beach front!Located at the gateway to Waikiki, the Ilikai is just...
Aloha Suites ~ 2 Bedrooms~ Cloud Forest
Welcome to Aloha Suites, a completely private retreat with its own entrance, two bedrooms, one bathroom, and no shared spaces. Originally built as an ʻohana unit (Hawaiian for in-law quarters), this serene hideaway is just 7.5 miles from Kona International Airport and...
Kihei Surfside 210 : Walk to Keawakapu Beach Park from 1 Bedroom Condo
New split AC system installed in 2024! Come experience the dynamic direct oceanfront views from this 2nd-floor vacation rental located in S. Kihei. Recently upgraded with new carpet throughout, a new sofa-bed and new window treatments. The hallway photo art reflects the...