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.
Hale Kauwela | Ko Olina | Resort Villa w/ Views
Summary:Welcome to Hale Kauwela in Ko Olina. Kick your feet up at this gorgeous villa perfect for your paradise vacation. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Professionally and locally designed, this condo captivates...
207 - Lovely Oceanfront One Bedroom Unit!
* This is one of the nicer one bedroom one bath units at the Kihei Surfside! * This ocean front condo has been significantly upgraded * 70 feet from the ocean - Watch the whales from your private Lanai * 100 feet from one of the finest beaches in Maui - Wonderful...
Unobstructed View of the Big Blue Pacific and A /C Throughout
Enjoy awesome ocean views from almost every room in this ocean front, three bedroom, 1126 square feet, fabulous unit! Living room, dining room, kitchen, Master bedroom and second Master offer 'front row' spectacular views of the Blue Pacific, West Maui mountains,...
Modern Ground Floor Retreat - Kihei Surfside #110 - Perfect Oceanfront Grounds!
Kihei Surfside #110 – Ground-Floor Oceanfront Condo with Stunning ViewsLocated just steps from Keawakapu Beach, Kihei Surfside #110 offers the perfect blend of comfort, convenience, and breathtaking oceanfront views. This ground-floor one-bedroom,...
Waikiki Sunset Mountain View Near Beach + 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...
Aloha Vibes w/ Ocean Views, Near Beach + 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...
Maui Kamaole Kihei Resort I Beaches, Pools, Tennis
Prime South Kihei location across the road from Kamaole Beach lll and a 15 minute walk or 5 minute drive to Keawakapu Beach. Set on a 23 acres, Maui Kamaole is a lush, tropical resort with two swimming pools + spas, and two tennis courts.J201 is a large, upgraded condo...
Ma'alaea Surf Unit E5-2BD Beachfront Condo, AC, Wifi, Pool, TV, Kitchen
Ma'alaea Surf, Unit E5, the most glorious and romantic sunset views at is why the architect who designed Ma'alaea Surf chose this unit for his home. Steps away from the wonderful walking beach and pool. This fully equipped unit features flat screen tv, cable, wifi,...
Oceanfront Resort steps to pool/beach via your lanai, 4 Beautiful Pools
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful first floor unit with excellent views of the resort and pools. Comfortable king bed with chaise lounge. Walk right out your lanai and you will be at the pools and...
Gorgeous Diamond Head Penthouse Studio Stunning views, Private Balcony.
Legally permitted vacation rental - 2947 Kalakaua Ave, Penthouse 5Stunning style with incredible Ocean & Diamond Head views.The care and attention to detail our owners put in, bringing their pride and joy on Hawaii's Gold Coast to fruition shows in every corner of this...
Tropical-view escape with pools, hot tub, tennis, AC, W/D - beaches await
Maui Kamaole D209Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Beachfront/View MAK-B1 -Quality Remodeled Condo in Ma’alaea Great Value
Are you looking for a luxurious and comfortable vacation rental that feels like home? Look no further than Makani A Kai # B-1, a deluxe condo located in a beachfront resort. With a minimum stay requirement of just five nights, this unit is perfect for a short or long...
Maui Banyan #Q-104: 2 Br in S Kihei, Walk to Beach, Shops and Dining
Located in building Q at the Maui Banyan, this two-bedroom condo has many upgrades and remodels. The Master bedroom has a queen bed and a full bathroom ensuite. The second bedroom has two full beds. There is a full bathroom just outside the second bedroom. The living...
Westside Magic Garden 3bed 2 bath house
Welcome to our charming vacation house located on the beautiful west side of Oahu, Hawaii! Our cozy rental is the perfect spot for travelers seeking a mix of adventure and relaxation, as we are conveniently located near some of the island's most stunning beaches, hiking...
Luxurious Makai Villa with Pool and Ocean Views
Aloha and welcome to our custom pool in Kailua-Kona! We have tastefully decorated this casual luxury home for your enjoyment. The large pool and lanai are set up for entertaining during sunny warm days or star-filled nights. This home has space for a large family or...
Sept.-Nov. Special $350 nt! BEAUTIFUL NEWLY RENOVATED OCEANFRONT
CONDO had A FULL RENOVATION,WITH BEAUTIFUL UPGRADES AND ALL NEW FURNISHINGS. The condo is a 1700 sq ft. ocean front, fifth floor, two bedroom, two bathroom condominium with AC that offers stunning views of Hawaiian sunsets, whales, sea turtles, and the islands of...
1 Bedroom Corner Oceanfront #701
Our One Bedroom Corner 701 unit is spacious and well-appointed with a King Bed in the bedroom and a Queen sofa bed in the living room. There is seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The...
Serene 5-acre tropical hideaway with lanai and circular wood-burning fireplace
Hale Hapu'uOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled on five acres of rainforest, Hale Hapu'u is a serene two-bedroom, three-bath hideaway home in Volcano Village. This...
Charming 1br Top Floor Condo in Poipu, AC, Athletic Club, Beach Access
Welcome to Sunny Poipu Beach! This charming top floor Kiahuna Plantation condo was freshly remodeled with you in mind! Relax on your private lanai overlooking the garden while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips....
Akahai at Poipu Beach By Parrish Kauai - elite home private pool & central AC!
Tucked back in one of Poipu Beach’s newest vacation rental neighborhoods, Akahai offers an exquisite and distinguished private luxury Kauai vacation rental unmatched by many. This exquisite three bedroom home offers a modern and open floorplan with designer touches,...
Ocean Front Pool, Private and Newly Renovated Top Corner Unit
Welcome to our condo in Hawaii, we like to give everyone a well deserved and affordable vacation. This is a very private and newly renovated, top floor corner unit centrally located in Kailua-Kona, Big Island Hawaii. 350 days of sunny weather in a year with some of the...
KBVC3 · Tropical 1 Bedroom with 2 Full Bath at Resort
Welcome to "Wahi Maluhia"! Peace to replenish your soul at this beautiful, simple Tropical Condo. Walk to the beach, enjoy the pools and spas, play some tennis and take advantage of grounds of adjacent Resort and picturesque oceanfront setting. Free parking affords you...
Village Manor B22, In the Heart of Kapaa Town, Walk to Shops and Beaches
Plumeria Hale, Village Manor Apartment: #B22. Waipouli, Kapa'a, Kaua`i Vacation Rental. Accommodates up to 4 guests, including children and infants."Plumeria Hale" is a bright and airy second story, two-bedroom condo with partial ocean views, located a short walk to the...
New! Lae Nani 536, Oceanfront, Tropical Oasis, Steps to Beach and Town
Lae Nani Resort Kauai #536, Beautiful Oceanfront Unit on a Tropical Beachfront Oasis. This Kauai Vacation Rental is conveniently located in Kapaa Town within walking distance to shops, restaurants, and just steps to beautiful white sandy beaches. Accommodates up to 4...
Waikoloa Beach Villas M2 - Ground Floor Villa, Fairway Views, Close to Beach!
Discover the spirit of Aloha! Tucked away next to one of the Aloha states largest and most luxurious resorts, this 2 bedroom 2 bathroom villa is a destination in itself. Located on the golf course, and only a few minutes walk from the beach, there is no better way to...
RK 104 BeachFront West Maui Studio w Pool and AC
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 Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Charming studio with killer ocean views, balcony & outdoor pool
Kapa'a Sands 11Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ever dreamed of spending time in a cute little Hawaiian bungalow overlooking the ocean? This is it! Kapa’a Sands is...
DISCOUNTED RATES! 213 Beautiful oceanfront 1 bed/bath, 2nd floor condo
Gene and I live in Portland, Oregon. We first came to the Kulakane for our honeymoon in 1987 and that makes this our honeymoon home. We loved Hawaii and returned often, to The Kulakane and to other properties and islands. We kept coming back to the Kulakane as our...
Ohi'a Kona Estates: Hosted Bed & Breakfast with 5 Bedrooms
Celebrate your Hawaiian holiday with friends & family in your own Bed & Breakfast dedicated to you and your group!!Away from the hustle and bustle of tourists and traffic, Ohi'a Kona Estates is located in the hills above Kona with beautiful views of the Pacific and 15...
Pali Ke Kua 244, Overlooks the Pacific Ocean.
This two-bedroom condo is located in the resort community of Princeville which overlooks the Pacific Ocean. The vaulted ceiling in the living area lends a spacious and airy feel to this nicely appointed condo. You can take in the gorgeous ocean views from the living...
Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!
Waikiki Sunset #2503 – 229 Paoakalani Ave.Enjoy the lush greenery of the Ko'olau Mountains and exquisite Hawaiian trade winds from your private lanai! This cozy rental features central A/C, a full kitchen, and free Wi-Fi—perfect for couples and small families!The...
Hawaii Life Presents "Kahua Kai" Whaler 102- Direct Oceanfront 2BR/2BA
***DISCLOSURE: Please be advised that the BBQ area is currently restricted and unavailable for use due to ongoing reconstruction.As a result of this construction, ocean views from certain areas may be temporarily affected by equipment, materials, and the presence of...
Perfect Ocean View! Ilikai 1 Bedroom Harbor View, Minutes to the Beach!
1 Bedroom Yacht Harbor View on the 18th Floor! NEWS FLASH! This condo was completely gutted & renovated with brand new stainless steel appliances and furniture! Nothing was spared when completing this upgrade, it checks off all the marks for everything you'll need to...
Oahu North Shore Vacation Home @ Kuilima Estates West
Elegant Hawaiian Home: A Spacious Retreat with Resort-Style Living on Oahu’s North ShoreWelcome to this beautifully appointed 3-bedroom, 2-bathroom Hawaiian home, where elegance meets comfort. Located in a prime North Shore setting, this fully air-conditioned home has...
Maui Resort Rentals: Honua Kai Hokulani 822 – Expansive 2BR Corner Suite w/ Gorgeous Mountain Views!
One of the absolute best values available at Honua Kai, Hokulani 822 is a luxurious 2BR/2BA suite offering panoramic views of the lush West Maui Mountains from its fantastic 8th-floor corner location. You can even catch glimpses of the tranquil blue Pacific in the...
TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Maui Banyan complex and condo are located just a short walk to the Kamaole Beach Park II. This is one of South Maui's best Life Guarded Beaches.The unit is fully furnished with all the comforts of your own personal home. Also includes amenities you will enjoy during...
Kihei Bay Surf 144 Tropical Hawaiian Style Condo, Beachy Theme New Split A/C
Kihei Bay Surf Studio #144 is a beautifully remodeled studio with a new split system A/C that can sleep up to 3 with a queen bed and a queen Tommy Bahama sofa bed. The unit is conveniently located on the lower level, and the lanai overlooks the pool area. This tiled...
OCEANFRONT 1 Bdrm Condo next to the water! Air conditioned - Kaleialoha 209
Enjoy breathtaking oceanfront views from this upgraded 1-bedroom, 1-bathroom condo at Kaleialoha, ideally located between Kaanapali and Kapalua. Perfect for couples or small families, this fully furnished unit features island-inspired décor, air conditioning, and a...
If you're looking for your get-away spot, look no further.
***NEWS ALERT!*** This condo was gutted, fully renovated and tastefully decorated with brand new stainless steel appliances, furniture, roller shades, painting, the works!! This condo is located on the 6th floor of the Ilikai Hotel. Live in luxury with this spacious 500...
Suite 422 at The Waikiki Grand
Legally permitted rental - ☀WAIKIKI GRAND HOTEL®134 Kapahulu Ave #422Sleek and modern, remodeled from top to bottom & with one of largest floor plans at the WAIKIKI GRAND HOTEL® - privately owned and operated - It's ideal for longer stays with kitchen and full-size...
Reduced Summer Rate at North Kihei oceanfront condo with spectacular views
Village by the Sea at Kauhale Makai 530Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to a Hawaiian paradise at Kauhale Makai in Kihei, offering breathtaking sunsets,...
Puu Poa 204
Puu Poa 204Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up in paradise when you stay at this spacious oceanfront condo. When you're not having a beach day, enjoy alfresco...
Honolulu Vacation Rental: Walk to Waikiki Beach!
Discover your Hawaiian paradise with a stay at this 1-bedroom, 1-bathroom vacation rental condo in beautiful Honolulu! Located only moments away from Waikiki Beach, this cozy retreat offers a private balcony with ocean views, access to tennis courts, and more! While...
Third-Floor Beach Condo w/ an Ocean View, Free WiFi, Washer/Dryer, & Shared Pool
Nohonani 306Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get a taste of the tropics both inside and out at this darling, third-floor condo. Save a little money and prepare...
Heavenly Enchanting Waterfall in Hilo
Immerse yourself in the magic of the Kikala Waterfall Lodge, where cascading waterfalls and the enchanting Mauna Kea Cloudforest Bioreserve create a one-of-a-kind escape. Wake to the soothing sounds of waterfalls just steps from your door and explore lush botanical...
Amazing Pacific views from 2bd Top Floor condo
Paki Maui 405 is a 2-bedroom, 2-bathroom oceanfront condo located on the top/4th floor with wonderful unobstructed ocean views from your lanai and floor-to-ceiling double sliding glass doors, bringing natural light into the condo. The condo has a split AC conditioning...
KBR #208 - 1 Bedroom/1 Bath Serene Ocean Front unit on Stunning Sugar Beach!
This beachfront one-bedroom / one-bath condo in North Kihei, Maui offers a serene and beautiful retreat on Sugar Beach. The unit features quality finishes such as granite countertops, tile flooring, and lovely furniture. Central A/C, a spacious bedroom with a king bed,...
Maui Resort Rentals: Honua Kai Konea 839 - Top Floor Deluxe 2BR, Expansive Corner Floor Plan, Stunning Ocean Views!
As one of the finest two-bedroom suites available to rent at the entire Honua Kai Resort, Konea 839 boasts an exceptional 8th-floor penthouse corner vantage point and is among a class of the most sought-after 2 bedroom floor plans at Honua Kai.What distinguishes this...
Comfortable condo, ocean views from both lanais
Kahana Sunset E4 is a ground floor, 2 bedroom, 2-bathroom condo that features ocean views and split A/C units located in both bedrooms and the living room. Unit that can accommodate up to 7 guests. The master bedroom has a king-size bed and its own TV with cable. Enjoy...
34th Floor Ala Moana Large Regal Suite - 2Br/3Ba, Book Now at Special Rate!
Here in our 34th floor 2 bedroom/3 bath Regal Suite at the Ala Moana Hotel condo, you will experience island-style comfort in one of Hawaii's most convenient locations. This unit is located very close to the beaches and the state's largest shopping mall, Ala Moana...