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.
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, Golf View, Well Equipped, Near Pool
Welcome to your Waikoloa escape - a relaxing retreat close to beaches, pools & island adventures!- Sleeps 6 | 2 bedrooms | 2 beds | 2 baths- 2 shared pools w/ waterfall & hot tub- Tennis courts & BBQ grill- Patio plus beach essentials- Kitchen, Wifi & workspace-...
PK H106 Remodeled 2BD Condo w Pool Hot Tub Pickleball
Papakea H106 Enjoy Fun Family Vacations at Our Remodeled Tropical 2Bedroom Ground Floor Condo at Papakea Resort with Pool, Hot Tub, Pickleball Court, and More On-Site Amenities FREE daily activities included with your stay value up to $570! Complimentary admission,...
Newly renovated 2nd floor condo — 150 yards from Mama’s Beach!
Right on the fabled road to Hana just one mile east of Paia Town, this little gem of a hideway offers a sampling of both sides of Maui, "mauka" (toward the mountain) and "makai" (toward the sea): From this home's front entryway, an unobstructed view of majestic...
KONA PACIFIC B-409 AMAZ OCEAN VIEW, Huge Lanai, WALK TO TOWN! Elevator, AC!!
Kona Pacific B-409 is a remodeled upper floor condo with breathtaking ocean views! The owners have extensively upgraded and made changes that every guest will absolutely LOVE!This condo has an extremely spacious lanai allowing access from all rooms: Living room, master...
NP B44 Remodeled OceanFront Getaway Relax Recharge in Comfort
Napili Point B44 Perfect OceanFront in Tropical Paradise Maui with Stunning 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...
Incredible Absolute Oceanfront Penthouse 🏝️ The Living Room Faces The Ocean! 🐠 KSR 1-305
Absolute oceanfront top floor condo with FREE AC thru-out! 3 bedrooms and 3 bathrooms - suitable for up to 6 guests. The person responsible for making the reservation must be at least 25 years of age for this property.From the moment you walk in you will see and hear...
Ilikai Marina 1792 Ocean / Sunset / Fireworks Views King Bed, Sofa Bed
UNOBSTRUCTED SUNSET/OCEAN VIEWS! STEPS TO WAIKIKI BEACH. Walk to parks, shopping mall, restaurants, shops, buses, rental cars & Waikiki night life. Parking available. No smoking room. Clean and fresh high floor.UNOBSTRUCTED SUNSET/OCEAN VIEWS! STEPS TO WAIKIKI BEACH....
Islander on the Beach 245 Direct Oceanfront View
"Escape to Kauai and Experience Warm Aloha! Enjoy Last-Minute Deals Through March 2026!".Direct Oceanfront Studio and Direct Oceanfront View with Split Fujitsu ACNEW Queen Alexander memory foam mattress and boxspring purchased November 2023! Plus full size pull-out...
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...
Maui Kamaole H106: Beautifully remodeled 1 br, 2 ba Ocean View condo within
PROPERTY PROJECT:The upper pool will be closed from November 11th through November 21st 2025 to re-coat the upper pool deck. Remodeled one (1) bedroom Oceanview Condo. The Kitchen has new cabinetry, fixtures, granite countertops, and white appliances. This one-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...
New Bathrooms Coming Soon! Heated Pool and Hot Tub!
This is a wonderful ground floor condo! Nice and quiet with a lanai that looks onto the complex grassy grounds. This condo is so close to the pool, too! Condo has been recently renovated.There are 2 bedrooms and 2 bathrooms. The master has a king size bed with...
Walk to Beach & Sunset-Luxury Villa - Princeville Golf Course -3BR pool&Jacuzzi
Panoramic Princeville Golf Course View - Peaceful and QuietWe now have 1 Gigabit (1000 Mbps) Fiber Broadband Internet SpeedWelcome! to our newly renovated spacious 3 bedroom, 3 bathroom Villa located on a prestigious Princeville Golf course. This is one of the few...
Wailea Beach Villas PH504 - 2 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kaho‘olawe, Molokini crater, and Lanai. This generous two-bedroom, two-bathroom condo provides over 1900 sq. ft. of living space, outdoor lanai, entertaining space, plus a den. Located...
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...
Hale Ulili: Island-Style Kauai South Shore Vacation Home
Located on the dramatic Poipu coastline, this casual and unassuming island-style Kauai vacation home has ocean views from every room. Watch dolphins, turtles and seasonal whales swimming right off the property, waves crashing on the rocky coastline, and palms swaying in...
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...
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,...
Stunning home with multiple lanais, private gym, lush green space & fruit trees
Ke Kai OlinaOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the heart of Princeville, Hawaii, this stunning 6-bedroom house is a true tropical paradise. Surrounded by lush...
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...
Oceanviews From ALL Rooms 2BR - Maui Eldorado L105
This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances.Oceanfront Retreat – Private Beach Cabana, Golf Course Views, and Spacious LanaiE komo mai (welcome) to your island sanctuary, where the rhythm of the kai (ocean) and...
Panoramic Ocean and Waikiki Views from 1267-sf Penthouse with 195-sf Lanai!
Lanikea Waikiki Penthouse #1 – 421 Olohana St.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Welcome to Lanikea Waikiki Penthouse #1, a spacious luxury penthouse in the heart of Waikiki designed for extended stays. With over 1,260 sq ft of living...
Waikiki mountain view, close to beach & restaurants! Parking, kitchen, pool!
Waikiki Banyan #1105-T2 – 201 Ohua Ave.NEW TO OUR INVENTORY! Enjoy this newly refreshed (December 2022) 1-Bedroom/1-Bathroom condo with sweeping green views of the Ko'olau Mountains and Ala Wai Golf Course. With a full kitchen, free on-site parking for 1 vehicle, free...
Koa Resort #5G 3BR/2BA, Large townhome, Pool, AC, WIFI, Sleeps 8
Gorgeous remodeled townhome, across from ocean - Remodel includes all-tile and granite in kitchen and baths!Steps from Pool, BBQ at Cabana, A/C througout, FREE WIFIThis Koa Resort townhome is a completely remodeled 3 bedroom 2 bath home, located across from Kalepolepo...
Tropical Private Getaway on Kauai's North Shore!
Welcome to Pali Ke Kua 10—your North Shore retreat with stunning mountain and waterfall views! Nestled in one of Princeville’s most sought-after enclaves, this spacious condo offers a peaceful getaway with unforgettable scenery right from your private lanai, living...
Maalaea Condo w/ Pool Access - Walk to Beach!
Island life is right around the corner when you book a stay at this 2-bedroom, 2-bathroom vacation rental in Maalaea! Located steps from the beach, this lovely condo boasts a newly remodeled interior, a fully equipped kitchen, and a balcony overlooking the pool and...
Best Deals Ever! Amazing Condo is Hotel Zoned.nApril 110/ nightnMay 200/night
Before and after each guest's arrival and departure, our unit is thoroughly cleaned and disinfected to the upmost care. We value the safety and comfort of our guests, so please let us know if you have any questions. Our one bedroom / one bath ground floor condo is Hotel...
Private Townhouse on the North Shore - Kuilima Estates West #131
The perfect mixture of resort life in a private home. This spacious 3 bedroom, 2 bath townhome is located adjacent to the Turtle Bay Resort and its two golf courses, the Fazio and Palmer Courses. This unit is located in the Kuilima Estates, which provides access to the...
Maalaea 5 star Island Sands 100 2 bed Oceanfront
A wonderful modern unit on Maalaea Bay with a beautiful ocean view. The unit was just totally renovated throughout to Five Star Quality with all new floor, bathroom, kitchen, bedroom, living room, and lanai surfaces and furniture. Pleae see the wonderful attached...
Location, Location, Location. You can't get closer to the ocean for this price
Aloha!Welcome to our ocean paradise at the Kahana Outrigger. We take great pride in our island home and want to ensure you have everything you need for a very enjoyable and comfortable holiday. Our best advertising is the feedback from our guests - please do check out...
Kauai Birdsong at Poipu Crater! Spacious and private 2/2 minutes from the beach.
Your home away from home in Poipu with 2 bedrooms. This fantastic townhome features a cozy queen bed and a luxurious king bed, perfect for a good night's sleep. With amenities like a hair dryer, washer & dryer, WiFi, and AC, you'll have everything you need for a superb...
#128 Ground floor condo, easy access to best beach on Maui!
Ground floor Garden View unit, perfect for your Maui stay! Beautiful comfy couch, reclining chair and sitting chair complemented by a large entertainment center in living room. The bedroom has king size bed, with an additional new Queen hide-a-bed sofa in the living...
Sugar Beach Resort Condo w/ Private W/D, Free WiFi-Beach Lovers Dream
Sugar Beach Resort 118Our 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...
🏖️180 degree view of the Pacific Ocean | Private Pool | Gated Community | vrKCV
vrKCV - Keauhou Estates 4, Professionally Managed by Kona Coast VacationsSunset Paradise at Keauhou EstatesWelcome to Sunset Paradise, your luxurious retreat nestled within the gated community of Keauhou Estates on the Big Island of Hawai'i. This beautifully renovated...
4 Star Oceanfront Property, Kauai Beach Resort, 4 Pools, Restaurants on Site
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.This is a beautiful second floor unit with a view of the park and ocean behind it. Comfortable king bed with chaise lounge and balcony.The Outrigger Kauai Beach Resort and Spa...
Kihei Akahi Condo w/ Private W/D, A/C-Great Location
Kihei Akahi C417Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step across the street and enjoy Kamaole Beach Park II, one of Maui’s best swimming and stunning beaches. Revel in...
Sensational Seaside Condo, remodeled in 2023 parking available, 1 block to beach
Our unit is located on the 9th floor and is a corner unit with a large furnished lanai's which provide you with amazing city, mountain and partial ocean views.Available to our guest we provide you with a soft queen size pillow top Serta mattress for a comfortable nights...
KR601 - Panoramic Ocean Front - Top Floor Condo - Quiet & Relaxing!
Kealia 601 is a top-floor condo boasting breathtaking, unobstructed ocean views from the living/dining room, kitchen, and private lanai. Situated in a tranquil beachfront resort, this unit offers access to an exceptional 2.5-mile stretch of pristine white sand leading...
Delightful condo 2-bd condo close to the beach
Island Sands 105 is a 2-bedroom, 2-bathroom ground-floor condo that offers easy access, 1 window A/C in the living room, and a private washer and dryer. This property has elevators for easy access. Unit 105 can accommodate up to 6 guests. The master bedroom offers a...
Steps from Beach! - Luana Kai C210
This well-maintained, original two-bedroom, two-bath condo is located in the desirable Luana Kai oceanfront complex—just steps from five miles of breathtaking Sugar Beach! Take long strolls along the shoreline, watch for whales in the winter months, or relax in the...
Beachfront Condo
Beautiful updated beachfront condo on low traffic beach. Away from the touristy Honolulu, but close to nice lagoons and bays for swimming. 20 minutes from Ko Olina 45 mins from Honolulu. Stove, Oven, Microwave, Dishwasher and fridge/freezer. Our unit has a queen size...