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.
Astonishing top-floor condo in North Kihei
This stand-out designer property has breathtaking views and hand-crafted beautiful details throughout! There is no elevators in this resort. This 3rd-floor condo features beautiful craftsmanship and tasteful furnishings and décor as well as an excellent Maui location!...
Hale Hui Kai 206 - Newly Renovated!!
This private garden condo is on the second floor of the south side of the building ...about 60 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on the south shore of Maui, Hawaii, is known for its stunning natural beauty...
Sleek Waterfront Condo w/ a Shared Pool, Fast WiFi, & a Full Kitchen
Maunaloa Shores 109Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Bright, bold, and breezy, this waterfront condo offers deluxe amenities and comfortable furnishings to make your...
Beautiful Napili Shores Condo!
Napili Shores Condo #D130Kick back and relax at beautiful Napili Shores! You can do as much or as little as you want! Lounge poolside, kick back in the jacuzzi, or lay out on the golden sandy beach at Napili Bay and let the stress of daily life just melt away. Or maybe...
Nihi Kai 509 Resort Center - 2 bedroom/2 bath, AC
Summary:Stay cool and comfortable in this fully air-conditioned 2BR/2BA condo just a short walk from Poipu Beach and Brennecke’s Beach. Nihi Kai 509 features a two-level layout with garden views, an updated kitchen, private lanai, and access to a heated oceanfront pool,...
14th Floor Penthouse On Hawaii's Gold Coast At The Diamond Head Beach Hotel
Legally permitted vacation rentalâ¤2947 Kalakaua Ave 1401âš•âš•For your health and safetyâš•âš•We utilize additional Sterilization procedures between reservations.⬆Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head crater....
Captivating & Relaxing 5th Floor, Ocean Surrounds, A/C in Bedroom
Sunset Kahili is a 5th floor vacation rental property located in the beautiful Poipu Beach area of Kauai, Hawaii. The property was specifically designed to capture the breathtaking sunsets over the ocean, providing guests with a truly unforgettable experience.The condo...
Nihilani Family Condo 33A, Townhome Style, Close to Pool
Three bedrooms plus den with 1 king bed, 2 queen beds and 1 single bed, multiple lanai spaces, 2.5 bathrooms, washer and dryer in unit, 2 story town home, attached garage for one car, close to pool.Very spacious, this 3 bedroom, 3 bathroom town home is beautifully...
Renovated Condo in an Oceanfront Complex with AC, Lanai, and Pool/Hot Tub Access
Kauai Beach Villas D10Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy paradise with long strolls along the shoreline, and catch some of the most beautiful sunrises on Kauaʻi at...
Island dream Getaway PK-E304
Pono Kai's pool and spa will be closed January 6-31, 2026 for the installation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Island Dream Getaway is your perfect Kauai island escape! Nestled in the...
Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Aloha! This great condo is ground-floor, oceanfront, two-bedroom, two-bath — overlooks beautiful Wailua Bay on the Garden Isle of Kauai. From the lanai you look across the broad green lawn with its palm trees and tropical plantings to a natural sandy swimming beach.A...
❤️PiH❤️ Seabreeze ★Amazing Family Home ★ Private Pool & Spa ★ Bikes ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Seabreeze, a part of our Hawaiian Luxury Collection. Seabreeze at Mauna Lani Villages is a wonderful 4 bedroom home that features a private pool and spa, with luxurious high end finishes in a premier resort...
LIGHT & BREEZY Unit #115. West Maui open, Reserve now Maui Strong!
LIGHT & BREEZY style studio! Oceanview and is just steps from the sand. Located at The Napili Bay in West Maui, it is walking distance to Kapalua. Enjoy the blissful sandy beach and serene tropical water, not to mention the wonderful West Maui breezes. Discover why...
Upgraded Quiet Garden Oasis, Split System AC
This beautifully upgraded condo is meticulously cared for by the owners and it’s the first time in years that they have made this condo available for rental. While this unit enjoys a garden view from the lanai, the resort itself is situated right on the ocean bluff and...
Beautiful ground floor unit!
This spacious one bedroom condo sleeps four people comfortably. Step off your private lanai (patio) onto plush green grass for a short few steps to a beautiful heated swimming pool, surrounded by colorful tropical foliage. Then, take a few more steps through more...
Menehune Shores #623 – Top-Floor Penthouse with Stunning Ocean Views
Menehune Shores #623 – Top-Floor Penthouse with Stunning Ocean and Mountain ViewsWelcome to Menehune Shores #623, a beautifully remodeled penthouse that offers soaring ceilings and breathtaking views of both the ocean and mountains. This top-floor retreat blends modern...
Pali Ke Kua #241 - Top Floor Ocean View
Perched on an ocean bluff near Hanalei Bay, Pali Ke Kua Unit #241 is a one-bedroom + loft, two-bath, second-floor unit with sweeping ocean views. As of July 2021, there are 3 A/C portable units in the condo. Please note this condo does not have central AC. The family...
Time to go to Maui $125. per night! May and June only. Ocean view!
Aloha, Our spacious one bedroom condominium C309 at the popular Kihei Akahi complex in South Maui is located on the 3rd floor of the C bldg, C309, with a nice ocean view. We have a new King Size bed and new bedroom furniture. Overlooking the blue Pacific waters at...
Ocean Front Pool Club. Includes Beach Gear! Halii Kai 24H
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 24H. Stunning 3 bedrooms. Ocean Front Pool ClubPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin...
Traditional Hawai'i home near Hilo town - solar powered!
E komo mai (welcome!) to this 1940s plantation-era home in Hilo, the cultural center of Hawai’i. Here, you can hang loose and absorb the spirit of aloha while you explore the windward, tropical side of our island, including the Hamakua Coast and Volcano National Park....
❤️PiH❤️ Island Song Villa♥Dual Master★Amazing Views★Newly Decorated
Island Song Villa brought to you by Paradise in Hawaii Luxury Homes.Welcome to Island Song Villa, a part of our Hawaiian Luxury Collection. Island Song Villa at Islands is a wonderfully large, 2,189 square foot, two-bedroom home that can sleep 5. Located in the Islands...
Great Wailea studio Condo
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully this provides some clarity if you have been following this process and were concerned about booking in the next couple of...
Hilo SunShine Rental.2bds1ba,common swimming pool.
Two bedroom have window Air condition!The apartment is located in the center of Hilo, with an area of 575sf, located on the second floor, with two bedrooms, one living room, one bathroom and one balcony. Brand new decoration, brand new furniture! The community is safe...
Keauhou Palena - 2nd floor unit overlooking the golf course KP604
TMK: 780100320024TA: 008-300-1344-01Welcome to our beautiful unit at Keauhou Palena! The complex is right on the Kona Country Club and only a short walk to Keauhou Bay (1/4 mile). Keahou Shopping center nearby offers a movie theater, grocery shopping and plenty of local...
Malia Kai#5: Beautiful Townhome in Heart of Kona Town: Walk to everything!
Malia Kai#5 is a unique & special rental opportunity for your upcoming Hawaii Vacation! Enjoy Townhome Living with no one above or below you in the heart of Kona Town! You'll notice this intimate complex is extremely peaceful & the perfect oasis for one to enjoy the...
DISCOUNTED RATES! 113 Darling little ground floor 1 bed, 1 bath with A/C
Kulakane Resort is a West Maui vacation rental property, located just a few miles north of historic Lahaina Town. Each vacation rental property is professionally managed and superbly maintained to the highest standards. Your Maui vacation can be enjoyed in one of our...
Ocean view in Paradise
Our newly remodeled ocean view condo has a new Queen size bed and a full size kitchen that is fully stocked. It has a full size stove with oven, microwave and full size refrigerator.The Condo has everything you will need for your stay in paradise.It is a fully furnished...
#225 Your Slice of Paradise.
A LITTLE BIT ABOUT THIS CONDO... Polynesian Shores 225. Everything you need for your Maui dream vacation is here... just bring your suntan lotion and flip-flops and enjoy the Hawaiian sunshine. This condo has recently been refurbished to make your stay even more...
Stunning Views, Walk to Beach! Spacious Ekahi 49F
This listing has views from your lanai will have you coming back year after year--and the beach is a short stroll across the condo property! A cozy one bedroom and one bath second floor, this unit supplies you with everything you need for a memorable vacation. Choose...
Tropical Oceanfront Escape *Pure Elegance*
Step inside this newly remodeled tropical oasis, where panoramic ocean views greet you from the open concept living room, primary bedroom, lanai, and guest bedroom. Thoughtfully designed with comfort and style in mind, this condo boasts brand-new furnishings, plush...
Oceanfront condo with lanai, full water view, hot tub & pool
Kona Bali Kai #418Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Come in from the sun and enjoy the cool ceiling fans inside this tropical condo. A full view of the Pacific sets...
Escape to "Heavenly Haven", our beautiful, by the sea, comfortable Condo
This is a gorgeous one bedroom, completely handicap accessible, and completely remodeled condo. Our condo is one of the best in Kihei Garden Estates with granite countertops, tiled floors, large flat screen TV, marble shower, air conditioning, expanded digital cable ,...
Island View - Studio - Westin Kaanapali Ocean Resort Villas - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their...
Charming Historic Hilo House – Minutes to Beach!
Hula your way to Hawaiian paradise when you book this fully restored 1960's vacation rental house! This 3-bedroom, 2-bath Hilo home features a covered lanai and peek-a-boo ocean views from the yard. The University of Hawaii campus is a mere 1 block away while downtown...
ISLANDER AT THE BEACH OCEAN FRONT CONDO # 145
**** WE ARE UNDERGOING CONSTRUCTION , FOR THE MONTH OF JULY AND AUGUST AND ARE DISCOUNTING THE NIGHTLY RATE **** This ground floor ocean front condo next to pool and spa offer the perfect Kauai getaway. New Queen size bed, , studio offers comfortable accommodations and...
Hale Kamaole 117 first floor condo, easy access to best beach on Maui!
Hale Kamaole is just a short walk from the Kamaole Beach III, where milder tides, full facilities and a lifeguard post makes for a low stress family atmosphere. Kamaole III is one of Maui’s favorite beaches and is great for snorkeling, a morning swim and postcard...
KKSR2103 DIRECT OCEANFRONT, Ground Floor, REMODELED KITCHEN, AIR CONDITIONING
Welcome to Paradise! You found the perfect condo for your Hawaiian Vacation. 2-103 at the Surf & Racquet Club is a gorgeous, 2 bedroom, 2 bath DIRECT oceanfront ground floor property. This property has EVERYTHING you'll need. Wifi, Beach Gear, all available for your...
Whale watcher's delight! Spacious penthouse, views
This spacious top floor condo in the upscale Puu Poa complex on the north shore of beautiful Kauai is located directly next door to the Princeville One Hotel. You'll love the newly renovated oceanfront pool! Also available onsite are tennis courts, pickleball court, and...
ALOHA-WAIKIKI OCEAN VIEWS, POOL, FREE PARKING, SLEEP 4 and MORE!!! WB28
Large one bedroom Apartment has nice peeks of the Ocean & Diamond Head from balcony, bedroom & living room. FREE PARKING for one vehicle with this unit, Pool, BBQ and other perks on site makes this a great singles, couples and family destination within Waikiki AND only...
Panoramic Ocean Views, Pools & Hot Tubs
Welcome to your slice of paradise at Country Club Villas #325! This top-floor corner unit is one of only four exclusive residences in the complex, offering 1,271 square feet of extra living space and breathtaking views. Perfectly positioned with frontage on the golf...
Enjoy Vintage Hawaiiana! Napili Maui awaits!nFree reserved parking spot for unit
5 MINUTE WALK TO NAPILI BAY BEACH. Our Napili condo is walking distance to Napili Beach, Kapalua Beach and Kapalua golf resort. You can enjoy the best of both worlds, amenities you would find at a local condo resort plus the quiet and privacy of a local resident.Free...
☀️5br / 4ba ★Huge - 2500sf★Sleeps 11 ★Walk to Beach, 30 seconds to pool.★Hyatt
Spread out in this massive 2500sf of interior space spread across 5 bedrooms, 4 bathrooms, and spacious common living. It's great to vacation together, but it's a bonus to not be stepping on people's toes when relaxing after a long day at the nearby beach. ♔★This 5br...
Lahaina Shores Oceanfront Ocean Views Oasis
Beachfront Oasis: Stunning Views, Steps to the SandEscape to our beautiful oceanfront studio condo, where the rhythmic sound of waves will be your daily soundtrack. This newly renovated studio retreat offers the perfect blend of luxury and location, putting you just...
Oceanfront on Oahu's Gold Coast!
Colony Surf #604 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)The best of Hawaii awaits you in this large (1519 sf) oceanfront double-sized corner condo at renowned Colony Surf on...
Palms at Wailea - Fully Air Conditioned
Welcome to our Wailea Condo at the Palms of Wailea. Our condo is a large 1200 square foot newly renovated two bedroom, two bathroom condo that is walking distance to some of the best beaches in the world. For your convenience, we provide beach chairs, beach towels,...
Just finished complete renovation in March, 2025
Welcome to your Hawaiian Acacia tree oasis. Some call it the rain tree. Others call it the Monkeypod or Saman. You will call it home while you enjoy Kauai. Every detail of this remodel was meticulously crafted by hand using actual Monkeypod trees sustainably harvested...
Manualoha 901 - Minutes to Poipu and Brennecke`s Beach
Summary:Manualoha 901 is a spacious 3-bedroom, 3-bath condo just a short walk to Poipu Beach, Brennecke’s Beach, and Shipwreck Beach. This ground-floor retreat features portable A/C in all bedrooms, a large open layout, private lanais, and access to Manualoha’s pools,...
Two Bedroom Ocean View Deluxe Luana Kai A303
A303 is a deluxe, 2 bedroom, 2 bathroom ocean view condo with AC. A303 is on the third floor, there are NO elevators, so you are walking up stairs.A303 is on the third floor with great views of Molokini, Kahoolawe, Lanai, Maalaea Bay and the West Maui Mountains. It is...
Hoyochi Nikko A Quaint Oceanfront Retreat in Maui
Hoyochi Nikko 202This two-bedroom unit features a master bedroom on the main level with a king-size bed and a spiral staircase leading to a large lofted second bedroom with a queen-size bed. The unit is tastefully decorated with many custom features, and high vaulted...
Unit #209-3BR/2 Bath: 3 BR, 2 BA Condominium in Lahaina, Sleeps 6
Honokeana Cove 209 is a 3-bedroom 2-bath top floor unit just a quarter mile south of Napili Bay's sandy public beach. This lush, tropical 38-unit property sits on a secluded cove with breathtaking views of passing whales (in season), dolphins and the island of Molokai....