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.
Waimea Beach Cottage by Destination Kauai - Charming 2BD, A/C, Walk to Ocean/Pier
TVRNC-1316E Komo Mai, Welcome to Waimea Beach Cottage!This charming cottage and yard are privately yours to enjoy. Fully updated, there are two bedrooms each with a queen size bed and split unit AC for cooling off on Kaua'i's west side. The living area is cozy and...
Pali Ke Kua 223: 2 BR Princeville Condo with Ocean View
SPECIAL SALE! Reduced from $595 to $445 nightly during the remodel in unit 123 below. If you plan to go out and about during the day you might not be affected by the work below!Pali Ke Kua 223 COMPLETELY REMODELED.Perched on the bluff 200 feet above sea level,...
Beautiful Ocean View, totally remodeled Condo! SEE OUR REVIEWS!!!
Papakea Resort is a beautiful complex located on 13 oceanfront acres of lush tropical landscaping. ***New Bathroom counter/cabinet remodel******We installed a beautiful new tiled shower with solid glass door! July 2014***Our beautiful studio offers all the luxuries of...
Hale Kamaole 172 Ground floor condo, easy access to best beach on Maui!
Beautiful ground floor unit with Ocean View from lanai, close to the pool & easy access to BBQ. New wooden flooring.The unit sleeps 2 people. Unit 172’s living room area, offers comfortable couch and 2 sitting chairs, also a large flat screen TV. Up to date kitchen...
Waipouli Beach Resort Exceptional Condo Pool View Condo
Gorgeous Pool View! The Experience: Exceptionally well decorated, featuring Tommy Bahama furnishings. 2 King Beds and a queen Sofa SleeperThere is Central AC in this condo as well as a full size washer and dryer for laundry! Come indulge your senses on the enchanting...
Stunning 3 BR Penthouse: Ocean Views, AC, Lanais, Steps to Beach
Escape to South Maui & feel the warm Aloha when you treat yourself to this slice of Hawaiian penthouse! This corner unit boasts huge 1145 sf fits 8 comfortably inviting guests to bask in sunny wide views and glorious sunsets from either of 2 unobstructed balconies:...
Unobstructed oceanfront: sunsets, whales, breezes
Maui Kai 204 is a newly remodeled 1-bedroom, 1-bathroom condo that features a new fully stocked kitchen, bathroom, floors, ceiling, furniture, and appliances. With a king-size bed and two twin couches (day bed), this condo can accommodate up to 4. guests Open the double...
Clean and Beautifully Remodeled at Maui Kaanapali Villas-Sleeps 4 **
Lofted Condo, 1 Bedroom + Convertible single bed(s), 2 Baths, (Sleeps 4)Kaanapali Beach was rated #1 beach in North America and the island of Maui is rated #1 island in the world!We also own the unit right below B133 if you have additional friends or family joining you....
Tropical Garden End Unit A/C with Ocean & sunset Views! Walk to Keawakapu Beach!
Attention: Beach Lovers! Our condo is in the best location in the sunny beach town of South Kihei, bordering Wailea and across the street from the most beautiful sandy beach on Maui...Keawakapu Beach. This unpretentious Maui complex has a wonderful Hawaiian feel with...
Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,
The fabulous Keawakapu Beach is just a short 10 min stroll. The Palms at Wailea is a gorgeous property with a large pool and hot tub. A magnificent view of the ocean from the pool area. Unit #1801 is a spacious 2 bd, 2 ba ground floor unit. It has a fully-equipped...
Beachfront, Peek-a-Boo Ocean Views, Washer/Dryer, A/C, Wi-Fi!
Waikiki Shore #308 – 2161 Kalia Rd.NEW TO OUR INVENTORY! You'll adore this beautiful one-bedroom condo (706 sqft) right on the beach in Waikiki! Just imagine stepping right from the building onto world famous Waikiki Beach! After a day shopping or relaxing on the...
Honu Hideaway, Maui Kaanapali Oceanfront Penthouse
Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every nightLocated on the top 10th floor with close touch to ocean...
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Situated on a well groomed acre, Luana Cottage offers privacy as well as easy access to hiking, swimming, and exploring the beautiful Eastern side of Maui. Reverse Osmosis drinking water and solar hot water (with electric backup), along with a complete kitchen and...
Elegant & Serene Wai'ulu Villa 115D w/AC, Resort Pool & Golf Course Views
Chairman’s Club Event NoticeThe Hualalai Resort will host the annual Chairman’s Club event from December 1–6, 2025. Access to certain resort amenities may be limited during this time. Please inquire prior to booking if your stay falls within these dates.Mitsubishi...
NEW RENTaL! Experience Aloha *Hawaiian Style Hale*
High quality rental with Hawaiian Style home feeling. Upgraded kitchen. Fresh and clean. Relax and enjoy.PLEASE NOTE: Our prices include TAT/GET tax - Perfect for 1-5 people. This is a fully furnished guest 2 bedroom/1 bath house w/ full kitchen and has nice tropical...
Tropical Paradise in Luxurious 1br, 2ba Ground Floor Unit, Garden View, Palms 801
Welcome to Palms at Wailea 801, your ultimate tropical getaway on the island of Maui. At over 1000 square feet, our spacious and comfortable 1 bedroom, 2-bathroom ground floor unit is the perfect choice for a romantic escape or a small family vacation.As you enter the...
Kona Hawaii's Most Unique Ocean-View Vacation Home...Sweeping Ocean Views
Welcome to Villa LongBoard – Kona, Hawaii’s most unique and unforgettable vacation rental experience!Perched hillside on the gentle slopes of Mt. Hualalai, Villa LongBoard offers breathtaking panoramic ocean views, serene tropical breezes, and an atmosphere unlike...
Lovely Ocean View Second Floor End Unit, Great Views, Tennis Club Included
Unit 25 has certain attributes that make it especially desirable. It has recently been remodeled to improve the white water views while keeping the unique Kiahuna style redwood trim throughout. This is a second floor unit, which provides more privacy than the ground...
BEAUTIFUL OCEANFRONT MODERN West Maui Condo with Sunset Views!
Location! Location! Location! Ideally situated between famed Ka'anapali and Lahaina to the south and Kapalua to the north. At those locations you will find some of the best beaches, dining, shopping, golf, and water activities to be found in all of Hawaii. Our...
Ocean and Mountain Views - Spacious Cliffs 5-301 - 2 BR/2 BA
Perched on a bluff above the beautiful Pacific Ocean, Cliffs 5-301 is on the third floor (no elevator) with King bed in the Master bedroom and 2 Queen beds in the loft. You can enjoy wonderful views of the ocean and mountains as well as the lush foliage for which the...
Mauna Lani Palm Villas H4 Corner Two-story Villa with Floor to Ceiling Views
The Mauna Lani Resort is a world-famous, four-diamond resort with very nice restaurants, three pristine private beaches and miles of walking and jogging paths, two world-renowned golf courses, sunset cruises, fishing, whale watching, scuba, and the some of the best...
Hale Maluhia - 2 Minutes from the Big Island's Best Beaches
This darling and affordable two-bedroom, one bath house boasts an excellent view of the Kohala Coastline's blue water. Conveniently located in Kawaihae Village just minutes from luxury resorts and numerous white sandy beaches, this home is perfect for a small family....
Updated, Surf-Chic Condo w/ Amazing Mountain/Garden Views & Shared Pool/Hot Tub
Pali Ke Kua #3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a gorgeous lanai that opens to views of the mountains and the manicured gardens of Pali Ke Kua, this two-level...
**RENOVATED 07/20!** Corner Beachfront Penthouse in Kapa'a w/AC!!
As of April, 2023 our condo now has AC! Enjoy the Royal Coconut Coast in a 180 degree view oceanfront penthouse!Located on the trade wind side of the Garden Isle, you’ll relax your days away in tropical sun and gentle breezes. Soak in beautiful sunrises on the lanai...
Waikiki Cozy Apartment, 2 Bedrooms, FREE parking, Sleep 6
Aloha! BLACK FRIDAY LUXURY OFFER - 30% OFF.Reserve your one-week stay in paradise and enjoy exclusive savings and elevated amenities.Make your stay memorable at our island lifestyle vacation rental! Newly renovated 2 bedrooms with anti-noise windows, prime location in...
*Penthouse Condo with Panoramic Ocean Views!*
Summary:🌺 Welcome to our top-floor condo with breathtaking views of the Kilauea Lighthouse & Anini Reef! Large windows flood the space with light, showcasing the natural beauty all around. Enjoy the open-concept design & sip your morning coffee on the private lanai...
Family friendly condo near beach
This 'Regency at Poipu Kai,' non-smoking, two bedroom, two bath, garden view condo is centrally located in the Poipu area. The lush green surroundings are accentuated with palm trees, ginger, and hibiscus. This secluded, very private condo is a ground-floor unit with...
WHALER1257 1BR2BA, King and Wall Bed, Kitchen, W/D, SLEEPS 4, Great Ocean Views
We do not advertise on Craig's List, so please don't respond to any Craig's List listing for this condo. We don't want a crook to swindle you!Ocean View #1257, located high up on the 12th floor of the Whaler, offers amazing vistas of the Pacific Ocean, Kaanapali Beach,...
Maui Beach Front Condo Walking Distance to Beaches and Restaurants, ocean views
Newly remodeled spacious 1180 sq feet 2 bedroom, 2 bathroom condo with vaulted ceilings. Located within easy walking distance to shops, restaurants, and the best beaches on Maui. This unit is perfect for singles, couples, or families!This is not just an investment...
Fabulous, Ocean & Golf Course Views! Air Conditioning in Both Bedrooms
This beautiful, spacious condo is in a quiet location next to the Makai Golf Course and close to two other golf courses, within walking distance from the 1 Hotel Hanalei Bay, beaches and snorkeling sites, and near the Princeville Golf Clubhouse. It is almost 1500 square...
STUNNING BRAND NEW REMODEL-OCEAN VIEWS-LARGE LANAI-AC-WELL EQUIPPED
Book with confidence, this stunning brand new remodeled 1 bedroom, 2 bathroom (818 sq ft.) condo at Kamaole Sands. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and...
Steps from the pool and across the beach! Maui Vista 1118
Soak in the sun and unwind at this stunning condo in the heart of South Kihei. Located on the bottom floor in the first building and only steps away from the pool. We are a short walking distance from the famous Charley Young Beach, and close to fantastic restaurants,...
Lae Nani 114 Beautiful Ground Floor Beachfront Condo in Kapa'a!
This beautiful ground floor condo is 50 steps from one of the best looking pools on Kauai. The condo is blessed with great sunset views then shade in the afternoon and the lanai has the sounds of the ocean waves kissing the shore.This condo has been updated with...
Ocean-view penthouse with beach access, 2 balconies & amazing location
Island Surf 601Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This property is zoned in a Community Business District, ensuring short-term rentals are permitted now and in the...
Chic Mountain View Unit Near Waikiki 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...
Private home across the street from the beach. Minutes from downtown Hilo
This extraordinary property is across the street from the most beautiful beaches in Hilo. This property, with multiple Ka Wai Ola, (Living Springs) offers you all that Hawaii Island has to offer. Once only a place for Hawaii's royalty, we offer this very special...
Three Palms
Situated at 600 feet elevation on the side of Hualalai Volcano, Three Palms is a private, two-room (plus a bath) suite in a private residence in a quiet neighborhood overlooking Kailua Kona and the Pacific. The location is ideal...only a few hundred yards up the...
Maui Kihei 2bd oceanfront getaway
Welcome to Maui Sunset B420, a charming and inviting 2-bedroom, 2-bathroom condo located on a stunning oceanfront property. This delightful retreat offers a blend of comfort, convenience, and breathtaking views, making it the ideal destination for your Hawaiian...
Luxury townhouse on Turtle Bay - Kuilima Estates West
Aloha my friend! We invite you to come and experience your tropical paradise...your new home away from home at Turtle Bay Kuilima Estates! Located on the North Shore of Oahu at Turtle Bay, this townhome sits on the Championship Fazio Golf Course with a lake view and a...
Waipouli Beach Resort Exquisite Ground Floor Pool View
Waipouli Beach Resort - Amazing Inner Courtyard One Bedroom CondoThis ground floor deluxe 1 bedroom, 2 bath condominium has a fabulous view overlooking the lazy river-like pool, garden and towards the ocean.There is Central AC in this condo as well as a full size washer...
Unit 520 Ocean Front Condo "serene and affordable"
Aloha and welcome to Menehune Shores condo 520!Enjoy the ocean breezes in our fifth-floor, ocean-front unit. Whether you are here for just a few days or a month, you’ll find everything you need: smart television, Wi-Fi, a fully stocked kitchen, and a private lanai...
TMK 570010290064nNeighbor island feel - with the benefits of Oahu nearby.
Like being on a neighbor island, The location, views and overall ambiance gives you a true island feel but you also have the benefit of Honolulu's city life too! Our unit is on the West side of the island and our guests have full access to the Condo's onsite swimming...
FULLY REMODELED COASTAL DESIGN*DIRECTLY ON BEACH!
For travelers seeking luxury and an escape from life in the full resort, this complex is one of the most exclusive sanctuaries. This beautifully renovated 767 square foot property is a spectacular beachfront vacation rental with million dollar ocean views. You will love...
Luxury 4 Bedroom with private pool & Spa
Enjoy your own private pool with fairway views in this exclusive location off the 4th hole of the Mauna Lani golf course. Utilize and enjoy the open kitchen connected through sliding doors to the lanai with outdoor BBQ grill and fridge. Finished with luxurious details...
Newly Remodeled--2 Minute Walk to Charley Young Beach--Maui Vista #1216
Welcome to Maui Vista unit #1216! Just bring your Aloha spirit and we will provide all the rest. This unit has undergone a complete remodel as of October 2022. We are the same owners as before and look forward to continue providing our guests with the best stay possible...
OCEANFRONT Kona Reef, Top Rated Reviewsnn
Kona Reef, beautiful one-bedroom, direct oceanfront condominium, on world-famous Alii Drive. Our condo is 23 feet from the ocean and offers spectacular sunsets. Watch the surfers and the dolphins from the lanai.This immaculate, recently upgraded condo has every thing...
🏖️Exquisite Ocean Front | Beautifully Upgraded | Corner Unit | vrKCV
vrKCV - Surf and Racquet 1206, Professionally Managed by Kona Coast VacationsKeauhou-Kona Surf & Racquet Club #1206 – Oceanfront Luxury with Breathtaking ViewsStep into Pilialoha ("beloved") Kona Ocean Condo and experience casual Hawaiian luxury at its finest. This...
5 Bed/5 Bath Craftsman Home with large lanai, Central A/C. Close to Beach.
Makalae is a warm welcoming and luxurious home with fine furnishings and fantastic views. This stunning property was expertly built to take full advantage of memorable sunsets in the western Hawaiian sky and the southern trade winds known as Ku'amanini of Weliweli or...
Experience Kamaole Sands 6-202, Stunning Renovation, Ocean View, Wi-Fi, Split AC
Welcome to Kamaole Sands 6-202, a beautifully updated 1-bedroom, 2-bathroom condo in the heart of South Kihei - just a short walk to the golden sands and calm waters of Kamaole Beach Park III. Nestled in the highly desirable Building 6 of the Kamaole Sands Resort, this...
Coastal Oasis on the Beach w/ Shared Pool, Ocean View, Private Balcony, & WiFi
Wailua Bay View 211Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Let all of life's cares slip away as you look out to the emerald blue water and golden sand with a favorite drink...