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.
Charming Studio Apartment with WiFi, AC in beautiful Diamond Head Beach Park!
Enjoy a peaceful stay at this wonderful studio apartment on the Gold Coast. The space features a queen bed and open floor plan. The bathroom includes bath and shower combo. In the additional living space, there's a comfy sofa bed for extra guests. Fall in love with this...
Luxury Fairwayfront Estate w/Private Pool, Spa, AC & Stunning Views: Kamilo #217
This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details.Welcome to Mauna Lani KaMilo #217 by Gather, a cozy and inviting four-bedroom, three-bathroom home in Kamuela, HI. Nestled on the stunning Kohala Coast within the...
Wavecrest Resort Building C ground floor
This is a newly renovated 1 bedroom condo on the ground floor in the 'C' building at Wavecrest Resort. It has been renovated with attention to detail including soothing colors, "black-out" curtains, crown molding throughout, beautifully tiled "step-in" shower, all new...
Resort beach condo - ocean-view lanai, fast WiFi - steps to pool & hot tub
Islander on the Beach 235Our 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...
Nicely appointed 1bd condo with ocean view
Hale Ono Loa 203 is a 1-bedroom, 1-bathroom 2nd-floor condo featuring stunning ocean views and an expansive lanai. This unit does not have A/C. The condo can accommodate up to 4 guests with a king-size bed in the bedroom and queen sleeper sofa bed in the living area....
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 condo. This 3rd-floor condo features beautiful craftsmanship and tasteful furnishings and décor as well as an excellent Maui location!...
HOLUALOA BAY VILLAS#105: REMODELED, SPACIOUS, OCEAN VIEWS, AIR CONDITIONING!
Holualoa Bay Villas, Unit#105 is absolutely STUNNING! This gorgeous remodeled 2 bedroom, 2 bathroom condo is right in the heart of Kailua-Kona, just across the street from the ocean, specifically gorgeous "Holualoa Bay". Watch waves crashing against the rocky coastline,...
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
NIHI KAI 509 AT KOLOA KAI VACATION RENTALSYour Garden View Escape in the Heart of PoipuWelcome to Nihi Kai 509, a beautifully updated 2-bedroom, 2-bathroom condo in the heart of Poipu. Located within walking distance to Brennecke’s Beach and Poipu Beach, this charming...
14th Floor Penthouse On Hawaii's Gold Coast At The Diamond Head Beach Hotel
Legally permitted vacation rental❤2947 Kalakaua Ave 1401⚕⚕For your health and safety⚕⚕We utilize additional Sterilization procedures between reservations.⬆Rooftop Penthouse - Sitting above the Pacific Ocean and nestled under Hawaii's iconic Diamond Head...
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...
Big Island Condo w/ Pool Access: Walk to Beach!
With its unbeatable location and access to on-site amenities, this Kailua-Kona condo provides the perfect launching point for your Hawaiian adventures! Start days with fresh fruit at the Kona Farmers Market, then explore Ali'i Drive's 'Ocean Front Mile' with unique...
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,...
2Bed/2Bath Penthouse Ocean/Diamond Head views, near Convention Center
You'll be sitting on top of the world at this spacious 2-bedroom, 2-bath Penthouse with an open living room and fully-equipped kitchen.The jaw-dropping 270-degree view includes Diamond Head, a sweeping ocean view, the Ala Wai Canal, the Ala Wai golf course, Ft DeRussy...
Fairway Terrace F-107: Waikoloa Condo Golf Course View With Pool
Gated Community in Waikoloa this 2 bedroom and 2 baths is situated on the 10th fairway of the Robert Trent Jones, Jr. golf course in Waikoloa Village.Hula your way to the Big Island for an incredible stay at this renovated 2-bed, 2-bath vacation rental condo Waikoloa...
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!'Lounge by the pool, take long strolls on the beach and catch some of the most beautiful sunrises you've ever...
Island dream Getaway PK-E304
Pono Kai's pool will be closed for repairs September 2025 through November 2025.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 Kapaa, this charming one...
Cute Plantation Cottage; Walk into Wailuku Town; Central Location!
Committed To Clean We’re committed to enhanced cleaning protocols developed in partnership with experts in health and hospitality. Here’s what we’re doing to clean and sanitize: We use cleaners and disinfectants effective against COVID-19.We thoroughly check each...
❤️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...
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...
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...
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...
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...
Bamboo Treehouse for 2 Near Volcanoes National Park
This secluded Treehouse is just minutes from the National park. Beautiful features, inside and out. Test out treehouse living while you enjoy Hawaii. Perfect for couples with 1 queen bed (We only allow 2 guests at a time) and is perfect for any romantic couple wanting a...
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...
New Listing! Kona Isle Oceanfront|1 BR|Pool,Lanai
Oceanfront Paradise at Kona Isle E32 – Cozy 1BR | Steps from the Sea!Escape to the tranquil beauty of the Big Island and make yourself at home in Kona Isle E32, a top-floor oceanfront condo nestled in one of Kailua-Kona’s most beloved communities. This thoughtfully...
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...
Maui Resort Rentals: Honua Kai Konea 515 - Upgraded 5th Floor Oceanview Studio
Incredible ocean views await you within steps of entering Konea 515, an opulent oceanview studio that provides impressive vistas of the Pacific Ocean and solitude from the prevailing trade winds. Relax and reconnect in the ample living space fully appointed for your...
#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...
Air-conditioned, elegant and spacious, golf course view, walk to beach!
Emmalani Court is a small tranquil Princeville condos complex adjacent to the Makai golf course, offering scenic ocean and golf course views, large air-conditioned units, and convenient access to the many beaches and attractions that north shore Kauai has to offer. The...
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...
Kona Isle C28. Corner Unit, 2nd Floor, Ocean Views, & Air Conditioning!
Kona Isle C-28 is a fantastic addition to Knutson & Associates Property Management! We're proud to represent this wonderful second floor, corner end unit in highly desirable Building C at the Kona Isle! These second floor units are truly remarkable. High enough for a...
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...
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
Enhanced COVID cleaning and disinfecting procedures for every check-in.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 St Regis Hotel. You'll love the newly renovated...
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!
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.The...