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.
15th Floor Studio at the Luana Waikiki Hotel
Beautiful high floor studio at Luana Waikiki, a fantastic boutique building located in the heart of Waikiki. The room sleeps 4 in a queen size bed and a full-size sleeper sofa. The kitchenette features granite countertops, under-counter fridge, microwave, 2 burner...
Spectacular Oceanfront 2 bedroom Villa with Sweeping Views, AC & pool.
Introducing our exclusive Oceanfront 2-bedroom Alii Villa, just 30 feet from the water! This luxurious home boasts an expansive great room with panoramic ocean views that seamlessly extend to the covered oceanfront lanai, offering the best sunset views in Maui. The...
Turtle Bay Luxury 2 Bedroom. Upper Floor with Upgrades. 90/TVU-0512
Come relax and play at our Turtle Bay hideaway. Our lovely 2 story condo is perfect for families or couples who like more spacious accommodations while staying here at Turtle Bay. Vaulted ceilings and a large lanai add to the feeling of roominess. Well stocked, gourmet...
GREAT HOME LARGE FAMILIES
Wonderful single family home with three bedrooms plus small den area off of master. Great for a family. Additional 1 BEDROOM Granny Flat has queen with a futon in the sitting area.WIFI upgraded to best Hawaii has to offer.Washer and dryer, wireless internet,...
Maui Oceanfront, Top Floor Ocean View in Kahana Reef
Hurray...after three years, construction on the sea wall is complete with new landscaping, new steps to the ocean and beach. It looks beautiful. Also, because of COVID-19 we have updated our cleaning process to include complete sanitation of the condo including all...
Professionally decorated 2bd ocean view condo
Papakea G302 is a 2-bedroom, 2-bathroom condo located on the third floor and can accommodate up to 6 guests. In the living room, you will find a Queen size sleeper sofa, bar stools, and dining table with chairs for four. You will also find a flat screen TV with cable...
Heart Of Waikiki, Perfect Location, Free Wi-Fi
239 sq/ft, super clean, all brand new furnishings and appliances, free Broadband and Wi-Fi Internet. Queen-size bed with designer linens, comfortable memory-foam mattress, and a premium brand pillows.40' flat screen Samsung Smart TV, browse Internet from your TV, watch...
Bungalow 1 with large kitchen, outdoor private shower and 1/2 bath.
On half acre of lush tropical setting, minutes away from the historic Holualoa village, (driving), home of the best coffee in the world, also 10 minutes away from Kailua-Kona and beaches, (driving). This room has its own private bathroom and kitchen with an outdoor and...
Laie Ohana Escape - AC Bedrooms, near beaches, PCC
*PER COUNTY REGULATION THIS PROPERTY ONLY ACCEPTS 1 BOOKING PER 30 DAYSAIR CONDITIONING in every room. Wow! This newly remodeled 5-bedroom, 2-bath home speaks comfort and convenience. Aside from having cool and relaxing bedrooms, the home interior has a bright and fun...
2bd with ocean views, steps from beach
Kana'i A Nalu 210 is a 2-bedroom, 2-bathroom condo located on the 2nd floor and offers an ocean, pool, and garden view along with 2 split A/C units, and a private washer/dryer. This property has an elevator for easy access. Unit 210 can accommodate up to 6 guests. The...
Beautiful Home Just Up From Brennecke's Beach w/Free WiFi and Ocean Views
Hale Kahanalu #3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Just walking distance to two world-class beaches, this lovely two-bedroom home is close to everything Southshore has...
Tropical downtown suite w/private hot tub & gazebo, washer & dryer, patio
Kailua View Estates -HoeneOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A serene paradise located just two minutes from downtown, this thoughtfully upgraded five-bedroom, five-bath...
414 - Gorgeous 2 Bedroom Oceanfront property with A/C!
Enjoy Hawaiian Paradise in our comfortable fourth floor, two bedroom, two bath, air-conditioned oceanfront condominium (830 sq ft). Kihei Surfside 414 features a relaxed environment with a tropical ambiance. We are very pleased to share the modern and spacious feel...
New Listing! 45 Seconds to Maui's Sugar Beach, Beautifully renovated Kihei Bay Vista B-102
Kihei Bay Vista B-102 is located just a 45 second walk to the longest stretch of white sand beach on Maui, this air-conditioned condo is fresh, newly updated, and completely furnished to host your romantic Maui getaway or family (up to four) adventure. Spectacular Sugar...
Elegant 3BR Ko Olina Beach Villa O505 Pool & Ocean View Luxury Escape
Welcome to Ko Olina Beach Villa O505 by Gather, a splendid 3-bedroom, 2.5-bathroom retreat in Kapolei, HI, designed to host up to six guests in a perfect blend of luxury and comfort. Perched on the 5th floor, this villa offers breathtaking views of the pool and ocean...
Keauhou Akahi Condo; Beautiful Ocean Views. Peaceful, Clean, Newly Renovated.
Fully Furnished Condo, with easy access. Our remodeled unit features recently upgraded master bedroom suite and full bath. Well maintained and meticulously cared for and just a few steps to the pool. Beautiful, ideal location above Keauhou Bay; Master Bdrm suite...
**SPRING SPECIAL*** Relax with Ocean breezes! Includes BBQ, Wifi, A/C in Bedrooms
Oceanfront Escape at Kahalu‘u Bay – Prime Location on Ali‘i DriveWelcome to your oceanfront haven at Kahalu‘u Bay! This beautifully renovated 3-bedroom, 3-bath retreat sits directly on iconic Ali‘i Drive and offers unforgettable coastal views, just steps from...
North Shore Turtle Bay Condo - Kuilima Estates East
750 sq ft ground one bedroom condominium with a fully stocked kitchen with granite counter-tops and glass top stove. A full bathroom with a tub, screened in lanai looking out over Turtle Bay’s Fazio Golf Course, open living area with a flat screen TV and couch. This...
Oceanfront Condo/Hawaiian Style. 1Bd, w/AC & Wifi
Honu's Hideway-a newly renovated condo with all the amenities, located just steps from the warm tropical waters and on Ali'i Dr a few minutes from Old Kona town Enjoy swimming, snorkeling sun bathing or surfing at Banyons, a local favorite. Swim, sun and enjoy the hot...
Kaha Lani Resort #224, Oceanfront, Sunrise Views, Walk to Lydgate Beach
Kaha Lani Unit #224 , Oceanfront Beachfront Resort, Wailua, Kauai. Steps to sandy beaches, surrounded by parks, a golf course, and the ocean. Relax to the sound of the waves. Enjoy one of Kauai's favorite "hidden secrets" at the Kaha Lani Resort! Oceanfront 2 bedroom, 2...
Gorgeous Luxury Ocean View 1 Bedroom Kamaole Sands 10-304
Book with us and come to Maui to explore everything we have to offer!Sought after building 10 third floor unit with large lanai lanai and ocean views. Constantly getting updated from the new owner with new TV's, new refrigerator, new lights. Air conditioning in both the...
Tropical oceanfront retreat with WiFi, hot tub, pool, and sweeping ocean views
Paki Maui 122Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to a vacation you'll never forget when you reserve your spot at this oceanfront getaway in Lahaina....
KS 725 Kaanapali 2BD in BeachFront Resort w Ocean Views
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...
Perfect North Shore, Oahu Vacation House.
This charming property is located in the heart of Oahu`s North Shore coastline. This gated property is located on a bike path so walk, bike (or drive) to Waimea Bay, Sunset Beach, Pipeline and Shark`s Cove. Grocery store and coffee shop is close by. The property offers...
Ocean-view condo with furnished lanai & pool - walk to beach & dining
Kailua Village Resort 605Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy central access to the best of Kailua-Kona from this breezy, ocean-view condo at Kailua Village. Cool...
Kona Mansions#C211 2nd Floor, Beautiful unit/Ocean views & Air Conditioning
Knutson & Associates is proud to be representing a spectacular condo!Kona MansionsC#211 is a wonderfully appointed property that has a phenomenal location. Stunning ocean views, just steps from lively nightlife and the best of Island fare, this 1 bed, 1 bath,...
Premier Ocean Bluff Condo with Spectacular Surf and Sunset Views
A completely remodeled modern vacation home with aesthetic island motifs that is ready to make your romantic getaway or your family adventure a Hawaiian dream. Take in stunning, vast oceanfront views from the private lanai and unique atrium of this modern Puu Poa ocean...
Newly Updated, Local Art, Well Equipped, Near Pool
Welcome to your tropical retreat at Waikoloa Colony Villas - the perfect blend of comfort, style & resort living on Hawaii’s Big Island! Enjoy vaulted ceilings, pools, and easy beach access:• Sleeps 6 | 2 bedrooms | 3 beds | 2 baths• 2 pools (1 w/ waterfall), hot...
Tropical Gem Near Waikiki Beach with Free 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...
Upgraded 2 Bed/2 Bath oceanfront property at the Royal Sea Cliff Central A/C
E Komo Mai to our Hale Pau Hana "house of no work”When you step into our slice of paradise at the Royal Sea Cliff, all your worries magically check out! **Oceanfront Bliss** Experience the magic of the Pacific Ocean right from your Lanai. Enjoy breathtaking ocean...
PK H106 Remodeled 2BD Condo w Pool Hot Tub Pickleball
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...
Oceanfront 2Bd 2Ba Sunset Suite in South Maui
Unbeatable Location, Unmatched Views – Your Dream Vacation Awaits!Get ready to experience the vacation of a lifetime in this renovated 2-bedroom, 2-bath oceanview condo at Kamaole Nalu. With jaw-dropping views of the sparkling Pacific, this gem is the perfect blend of...
NP B44 Remodeled OceanFront Getaway Relax Recharge in Comfort
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...
Spectacular Unobstructed FULL Oceanfront Unit
Nestled within the picturesque Kihei Beach Resort, this enchanting 1-bedroom, 1-bathroom unit invites you to experience the allure of an authentic Hawaiian aesthetic, effortlessly blending modern comfort with the timeless charm of the Aloha spirit.As you step inside, be...
Islander on the Beach 245 Direct Oceanfront View
"Kauai Mega Savings: August Deals Extended Through October! Book Now!".Important Notice:* Nihau Building Discount (Spalling Work)Special discounted rates are available in the Niihau building from June 23 to July 21, 2025, due to scheduled staircase, walkway, and lanai...
Sugar Beach Resort Condo w/ Shared Grill, A/C-Beach Lovers Dream
Sugar Beach Resort 136Our 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...
Ocean view room, Beachfront Kauai Beach Resort, Jacuzzis, 4 pools, restaurants
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful fourth floor unit with King bed. Lovely resort with amazing pools! Beautiful resort and ocean views from the room!!! The Outrigger Kauai Beach Resort and Spa is a...
Sugar Beach PH21 - Direct Oceanfront 1 bedroom
Book with us and come to Maui to explore everything we have to offer!Just Renovated!Beautiful views from a great unit. You will love the well maintained, upgraded corian kitchen and white cabinetry. Enjoy your coffee on the top floor balcony while looking at whales and...
Maui Kamaole H106: Beautifully remodeled 1 br, 2 ba Ocean View condo within
Remodeled one (1) bedroom Oceanview Condo. The Kitchen has new cabinetry, fixtures, granite countertops, and white appliances. This one-bedroom and two-bath unit sleeps up to 4 people with a king bed in the bedroom and a pull-out sofa bed in the living room. The bedroom...
Kihei Akahi #D-208: Calm & Tranquil One Bedroom Condo in South Kihei
The living area in this 2nd-floor one-bedroom condo and is thoughtfully furnished making the area comfortable and inviting. Tastefully remodeled, you will feel right at home in this recently updated vacation rental. Enjoy your morning coffee or afternoon Mai Tai on our...
5 minutes from the Beach | 3 Pools | Pickle Ball & Tennis Courts | BBQ areas
Discover your Maui haven—a one-bedroom, one-bath retreat of comfort and island charm. From the moment you arrive, the relaxed pace of Hawaiian living takes over. Sip your morning coffee on your private lanai, take a refreshing dip in the pool, or wander just five...
Direct OCEANFRONT, Rare Enclosed Lanai, AC - Maui Kai 804
Experience elevated island living at this beautifully updated 1-bedroom, 1-bathroom oceanfront condo at Maui Kai Resort on North Kaanapali Beach. With unobstructed views of Lanai and Molokai, a fully enclosed lanai for extended living space, and central air...
3rd Floor Condo Kiahuna A/C. Walk to Beach Shop and Restaurants. Ocean nView!n
4 guests-1 bedroom-2 beds-1 bath.You'll have a great time at this comfortable place to stay.Kiahuna Condo 331 overlooks beautiful Moir Gardens and has partial ocean views. The condo is tastefully redecorated with granite countertops and tiled shower. It has...
Makahuena 4304 by Destination Kauai - Partial Ocean View
E Komo Mai, Welcome to The Makahuena 4304!“The Makahuena” is located on the southernmost point of Kauai. This unique oceanside resort is situated on the edge of a bluff providing spectacular coastal views. This 2-bd/2.5-ba is a multi-level condo on the second story...
OCEANFRONT, SWEEPING Ocean Views Amazing Condo
Step into your own tropical perfection in the stunning "Keto Condo", at Kamaole One! This vibrant rental is tastefully furnished, recently remodeled and fully equipped for your comfort and enjoyment. Savor a refreshing morning breakfast while overlooking the sparkling...
Oceanfront, Beach , Pool, Wifi ,View! Relax Haw'n style #206 Portable AC
There is some construction to the left side of this unit the interior is the same ROMANTIC DIRECT OCEANFRONT CONDO A SHELLS TOSS TO THE WATER! Check out my video by clicking the icon to the left. Imagine yourself there!Wow! oceanfront! Treat yourself to a real Hawaiian...
Heart of Downtown Kona: Quiet, AC, Pool View
Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Tower 2 Suite 3709 - QQP by Koko Resort Vacation Rentals
Incredible Panoramic Views - 37th Floor, Free parking & Wi-Fi Enjoy paradise with an incredible mountain view Waikiki Banyan condo suiteonly one block from world famous Waikiki Beach! Condo suite is located on the37th floor and has a spectacular view of the mountains...
Quaint stand-alone cottage - 2 bedroom 2 bath
GE/TAT #181-710-4896-01 - "Hawaiian Cowboy Cottage"This is a unique stand alone cottage in the Princeville Paniolo condominium complex. The cottage has two large living spaces. Walk in the front door and turn right, that leads to the main living area, featuring living,...
In Town Ocean View Condo-Walk to the Beach, Shops, Restaurants and Bars!
This top floor condo is spacious with open beam ceilings and an ocean view. It is located in the center of Kailua Kona. You can walk to the pier, to restaurants, shopping, even the bank and the grocery store are nearby. The condo has two bedrooms with California King...