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.
Oceanview Poolside Paradise – Maui Kamaole L-201 - Your Dream Island Escape!
Maui Kamaole, #L-201 – Modern Island RetreatEscape to Maui Kamaole #L-201, a beautifully remodeled 2-bedroom, 2-bathroom condo located on a scenic hillside in South Kihei. This spacious upper-level unit offers a tranquil atmosphere with tropical garden surroundings,...
Tranquil condo with pools, hot tub, jetted tub, grill & board games - near beach
Poipu Mermaid 912Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'From the sands of Hawaii to the shores of Kauai, you'll be astounded by the beauty of this slice of paradise! You'll...
Free Parking! 6 Minute Walk to Waikiki Beach!
This is a legal conforming vacation rental. Please see our listing details for our license number.1990/NUC-1393TMK: 260280110114TA-111-582-2592-01This 1-bedroom vacation rental lies in the heart of Waikiki and is walking distance to the world-famous Waikiki Beach and...
🏖️Great Location | Modern Island condo | AC Included | vrKCV
vrKCV - Casa de Emdeko 221, Professionally Managed by Kona Coast VacationsWelcome to Casa de Emdeko #B221, your serene island escape just 150 yards from the ocean. This spacious 780-square-foot second-floor condo is perfect for 2–4 guests seeking comfort, relaxation,...
Aloha Royal Garden Studio | Pool + Great Amenities
Enjoy the refreshing Hawaii breeze and overlook the palm tree dotted Ala Wai Canal from the private Juliet lanai of this beautifully updated, hotel-style studio. As part of the luxurious Club Wyndham Royal Garden at Waikiki building, our guests enjoy the lovely gardens,...
Wai'ula'ula 308 - Upcountry Residence
This chic and sophisticated, ‘upcountry’ oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, an epicurean kitchen outfitted with Wolf appliances, including a gas range, double ovens and wine refrigerator, three guest...
Maui Parkshore 409: Have fun in this two bedroom, two bath Ocean View condo.
Have fun in this two-bedroom, two-bath Ocean View condo. Conveniently located in South Kihei, there are shops and restaurants just a block away. There is a popular beach park across the street and other beautiful beaches are just a short walk or drive away. There is a...
Oceanfront condo - ocean-view lanai - steps to beachside pool & hot tub
Islander on the Beach 250Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover the perfect ocean getaway at Islander on the Beach, a 6.5-acre oceanfront resort with stunning...
Perfect Location for your Maui Stay! Pacific Shores B118!
The best location on South Maui! Pacific Shores is all about convenience and location. Who needs a car when you are across the street from favorite Charley Young Beach, 1 block from popular surf spot ''The Cove'' and half a mile from many restaurants, shops, and...
Kona Mansions | Ocean Views & Amenities!
Summary:A complete Hawaiian experience can be found at Kona Mansions. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:This unit is a 1 bedroom, 1 bathroom ocean view condominium capable of accommodating up to 3 guests. Vacationers on...
Waiakea Villas Gem. Shared Pool & Private Balcony!
Your family will be close to everything including shopping, dining, activities, beaches and airport when you stay at this centrally-located place. Enjoy beautiful view of the flora, steps away from the Wailoa River state park, watch Nene, ducks and Koi. Or enjoy your...
Hale Kamaole 202 Second floor condo, easy access to best beach on Maui!
Welcome to your beach getaway! This 2 story, 2 bedroom plus loft, beautiful beach front condo comes with all the comforts of home including WI-FI, three flat screen TV’s, everything you will need in the kitchen to cook delicious meals and more. The kitchen is remodeled...
Lovely Room. Wir Sprechen Deutsch. Tropical Garden, Quiet
Centrally located on the hillside overlooking Kona Coast 7 miles north of downtown Kailua Kona, this is one of several accommodations we offer. A lovely room with queen bed, sleeper sofa, full bath, cable TV, small lanai, refrigerator, microwave, coffeemaker, hot water...
Oceanfront Condo with Gorgeous Views near Harbor with Pool, AC, WIFI
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to your perfect Maui getaway in the heart of Maalaea! This beautifully renovated 2 bedroom, 2 bathroom condo offers stunning ocean views from the living room, kitchen, lanai, and primary bedroom,...
Second Floor Oceanview with Gorgeous Sunsets
Hawaii Tax ID: TA-055-659-1104-01TMK: 390080030048This Hale Kai O'Kihei 219 condo is located directly on the ocean edge and boasts a 180 degree panoramic view of the mighty Pacific. Newly remodeled in 2015 kitchen and bathroom in this beautiful property offer the...
Kauhale Makai Unit 122: Ground floor 1 Bedroom condo at Ocean Front Resort
Spacious and comfortable describe this ground floor condo with a beautiful garden view and partial ocean/mountain views. This unit, which sleeps 4, boasts a fully equipped kitchen, separate dining, central AC and a large bedroom with a comfortable queen bed. Perfect for...
Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112
Book with us and come to Maui to explore everything we have to offer!This spacious Wailea Grand Champions Villas 2 bedroom 2 bath second floor unit is tastefully decorated and has everything you need for a relaxing vacation. Great ocean, tennis courts and tropical...
Family-friendly condo w/shared hot tub, outdoor pool, mountain and garden views
Pali Ke Kua #4Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Transport yourself to a tropical and magical paradise when you book this condo plus loft! Ideal for four people, this...
Unique Private Ocean View House With Pool - Walking Distance To Wailea Resorts
Wailea Freedom House is pure and simple elegance in an unmatched location backing onto the Wailea Blue Golf Course. This home has a large heated swimming pool with beautiful ocean views from the spacious pool deck area and upstairs lanai. The unique architecture boasts...
New baths, king bed, open & tranquil pool hot tub
Summary:Large, tastefully updated unit in desirable Shores at Waikoloa. Immerse yourself in the essence of Hawaiian paradise - light and bright, two-bedroom, two-bathroom haven offers a spacious retreat. Enjoy expansive, private lanai (balcony) with tropical views. With...
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
Min 30 days requiredLush tropical gardens make this private home into a quiet, comfortable retreat. Large enough for six adults, plus a couple of keiki (children), this home was designed by the late Vladimir Ossipoff, award-winning Hawaii architect. Mr. Ossipoff's...
Ilikai Apt 1822 - 2BR/2BA Modern Unit with Ocean & Harbor Views No resort fees!
Oceanfront 2BR/2BA at Ilikai | Sleeps 6 | Prime Waikiki LocationProperty Overview:Welcome to your spacious ocean-view retreat in the iconic Ilikai Hotel, just steps from the Hilton Lagoon and Waikiki Beach. This fully equipped 2-bedroom, 2-bathroom condo offers...
Ocean View Lanai W/Full-Kitchen – Waikīkī Shore #506
Castle Waikīkī Shore #506: Island living meets modern convenience in this recently upgraded one-bedroom and one-bathroom ocean-view suite.The full-size kitchen with modern furnishings and stainless-steel appliances makes this unit ideal for small families or a group of...
Kahakai Place - AC, Gated, 1 Block from the Ocean
Enjoy relaxed island living in this two-story, 3-bedroom, 2.5-bath Hawaiian home. Nestled in a small gated community, this private retreat offers a lush, tropical lanai and peaceful surroundings—yet you’re only minutes from the heart of downtown Kona. All the comforts...
Tropical condo near the beach with shared pool, hot tub, & private washer/dryer
Tropical Getaway at the Shores Waikoloa Beach #138Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha Waikoloa Beach! Escape to sheer tranquility when you stay at this luxe condo....
Oceanfront condo with loft, WiFi, shared pool & hot tub, balcony
Pali Ke Kua 213Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pali Ke Kua, situated in the planned community of Princeville on Kauai's magical North Shore, is often described as the...
Stunning Ocean View Hawaiian Downtown Getaway
Welcome to our tranquil oasis in the heart of downtown Kailua Kona! Perched on a hill, our stylish condo boasts breathtaking ocean views and easy access to all that the vibrant town has to offer.Step onto the private lanai and immerse yourself in the beauty of the...
2 Free Parking!! Spacious 1 Bedroom Penthouse in Palms at Waikiki.
You cannot find a penthouse, 2 parking, 1 bedroom vacation rental in this price!Room rate will be less than a half of the small studio class hotel room. More space, less price and 2 parking. You may also enjoy the diamond head and ocean view from the room!!From the...
Hale Kai 115: Oceanfront Paradise with Stunning Views and Poolside Access!
Hale Kai 115 offers magnificent ocean views and just steps to the pool! This ground floor 1 bedroom/1 bath is a perfect getaway for couples or a small family!As you enter, you are immediately drawn to views of Molokai, Lanai', and the beautiful Maui waters. Catch a...
Kona by the Sea Oceanfront Condo KBTS407
TMK: 750200160027TA-053-340-5696-01Relaxing Ocean Front Condo! Stunning direct ocean views. This one bedroom - two bath condominium has been fully updated with quality materials. Custom solid cherry wood cabinets and interior doors. Gleaming granite counter-tops in...
One Bedroom Deluxe Garden View Luana Kai Resort B108
B108 with AC is a Ground floor, 2 bedroom, 2 bathroom garden view condo. It offers easy access to the putting green, pool, bbq's, tennis, pickleball and ocean. B108 was totally remodeled and features a wonderful kitchen complete with everything you need to enjoy your...
Oceanfront views, top floor privacy, bright tropical interior
Sealodge C7 enjoys top floor privacy with endless oceanfront views at Sealodge Kauai. Inside you'll find charming vibrant decor and many updates and upgrades. You won't mind at all spending a quiet day inside when you can enjoy relaxing on the punee window seat in the...
Large 2 Bed 2 Bath in Gorgeous Maui Kamaole Complex South Maui
Perfectly perched on the second floor, our vacation rental offers a serene retreat elevated above the ordinary. Upon arrival, conveniently park your vehicle in the space directly in front of the property. A welcoming staircase leads you to the entrance of the condo,...
Modern, New King Bed, Luxury, Spacious Waikiki Condo with Great View 100% Legal!
Relax in paradise in your luxury suite on the 29th floor of the Hawaiian Monarch Hotel in fabulous Waikiki Beach! This apartment is designed for the discriminating traveler who wants to stay in a clean, spacious, and modern studio with a full kitchen (sorry but the oven...
🏖️Ocean View | Close to Pool & BBQ Area | vrKCV
vrKCV - Sea Village 2102, Professionally Managed by Kona Coast VacationsWelcome to Your Tropical Paradise at Sea Village in Kailua-Kona, Hawaii!Escape to this delightful one-bedroom, one-bath condo, perfectly situated just a short distance from downtown Kailua-Kona on...
Sugar Beach Resort Condo w/ A/C, Shared Grill-Close to Beaches
Sugar Beach Resort 309Our 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...
Golf Course Front Condo Near the Beach W/ Shared Pool, Balcony & WiFi
Kapalua Golf Villas 16V3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'What better place than Maui to let all of life's worries simply slip away with the tide? Sitting in the heart...
Cozy Mountain View Haven with Free Parking!
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Experience paradise in this renovated 1-bedroom condo at the family-friendly Waikiki Banyan (Tower 2)....
Ilikai Hotel's Deluxe One-Bedroom Unit with views of the Ala Wai Yacht Harbor and Ala Moana Beach!
Look no further, welcome to your dream vacation spot! This great condo is located within the OCEANFRONT Ilikai Hotel on the 12th floor and offers exquisite views of the ocean overlooking the Ala Wai Yacht harbor and Pacific Ocean. You'll be love waking up to the...
Magnificent ocean-view condo with golf, pool, balcony, & grilling area
Kauhale Makai Penthouse 607Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy spectacular views of daily sunrises and sunsets when you book a stay at Kauhale Makai Penthouse 607!...
Plantation Hale w/pool next to Coconut Marketplace in Kapaa (J15)
Welcome to our beautiful coconut coast condo! This is a one bedroom condo in Kapaa on the island of Kauai. It has a King size bed in the bedroom and a double sleeper sofa in the living room. That means it comfortably sleeps up to 4. The condo features a full kitchen,...
Maui Sunset Vacation Rentals B506
The island life from your top floor suite, relax on the large private covered lanai deck at the end of a long day of island living. Or see the ocean from the a/c living room, its time to unwind.Popular B side building on the 5th floor. Large private condominium...
Kaanapali Plantation 7 - Remodeled - Summer Discounts!
** Last-Minute Cancellations...take advantage of special end-of-year rates! ** Kaanapali Plantation #7 - Single level, spacious, two bedroom/two bath with central air conditioning. The jewel of this condominium is the lanai which can be accessed from the main living...
Tropical mini resort home in paradise 1ac yard. Whole home beautifully upgraded
For a group of 8 or less, one story of this beautiful tropical themed home would be sufficient space. For more than 8 people we provide extra sleeping with beautiful pull out queen beds .And lower level for super amount of storage space. bathroom , dining and living...
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches and Beyond
Hale Kai O Kihei 206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This Hale Kai O’ Kihei condo offers a breathtaking ocean view from every room and includes a private lanai that...
Turtle Bay Condo w/ Pool Access & Golf Course!
Pack your bags and retreat to Oahu's peaceful North Shore in this well-appointed and updated 1-bedroom, 1-bathroom Kahuku vacation rental. This modern masterpiece of a condo offers a flat-screen Smart TV, a private, screened patio with golf course views, access to 3...
Stunning! Diamond Head Oceanfront Lanai Condo - Sleeps 5
Legally permitted vacation rental - 2947 Kalakaua Ave #201A Spacious Condo with incredible Ocean views from our private oversized Lanai.Fitted with a new kitchen in March 2021 along with new living room furniture and 2 new comfortable Queen beds in the bedroom- We are...
Valentines Special! 10% OFF! Kahana Reef 212, Direct Oceanfront, 1B/1B, Sleeps 4
Indulge in the ultimate oceanfront retreat and discover your perfect Maui escape at Kahana Reef 212! A beautifully appointed second-floor condo nestled right on the ocean’s edge in the tranquil Kahana Reef community. This inviting one-bedroom retreat boasts expansive...
Aloha Condos, Keauhou Kona Surf and Racquet Club, Townhome 187, Oceanfront, AC
Direct Oceanfront LocationFree Wireless High Speed InternetFully Equipped Kitchen & Washer/DryerPrivate Oceanfront LanaiOceanfront Master Bedroom• Great Oceanfront Location• Pool, Cabana & BBQs• 3 Lighted Tennis Courts• Tropical Gardens & Flowers• Golfing, Swimming,...
Westin Nanea in Maui Available December 23-Dec 30, 2024
Come visit the lovely Westin Nanea Villa on the Kaanapali Coast of beautiful Maui. This property features a spacious 2 bedroom villa with full kitchen, living room, dining area, balcony or patio and washer/dryer. A Large Pool and Hot tub and Just Steps to the Beach,...