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.
Newly remodeled 1bd with contemporary finishes
Discover the ultimate island retreat at Kamaole Beach Royale #208—a 1-bedroom, 1-bathroom oasis perfectly situated within walking distance to both the beach and Kihei's vibrant shopping centers. This unit comfortably sleeps up to 4 guests. Renovated in 2022, this...
Ocean front Beach Resort Hale Nalu ~ ~
Aloha ~Step inside and experience the sophisticated charm of a newly renovated space, featuring a state-of-the-art kitchen equipped with modern appliances and sleek finishes, perfect for crafting island-inspired meals. The studio boasts a sumptuous king bed for a...
Spacious lanai-Maui Vista Relax/Work/Play in this lush tropical getaway!
Book 7+ days receive 10% discount, 30+ days receive 15% discount.Perfect location! Newly remodeled 1 bedroom/1 bathroom corner unit that sleeps 4. Ideally located with ocean and mountain views. Stay in style with everything you need for work and play. Start your day...
Posh, beachfront gingerbread home with 3 lanais- walk to parks, dining, tennis
Oceanfront Kalakaua Surf & SunsetsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located directly on spectacular Tonggs Beach, this posh 3BR/2.5BA home looks fresh from the pages of...
Rare, three bedroom Platinum Level remodeled townhouse, featuring the most premier ocean, island and coastal views!
*Please note that the Kapalua Resort and this property were not affected by the Lahaina fires, nor were our surrounding areas or Napili, Kahana and Kā‘anapali. West Maui communities of Kā‘anapali, Nāpili, Honokōwai, and Kapalua are fully open to visitors. Lahaina Town...
Breathtaking Ocean Views from Quiet Beachfront Condo! Free Parking & Wi-Fi!
Colony Surf #1005 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)Stunning ocean and Diamond Head views! This spacious (853 sq. ft.) open floor plan suite is the perfect spot to enjoy...
Lani Oasis - Princeville Vacation Home with Saltwater Pool
Lani Oasis welcomes you with its serene ambiance and tropical charm, perfectly situated in beautiful Princeville, Hawaii. This luxurious villa is designed for both relaxation and recreation, featuring a private saltwater pool surrounded by lush gardens and inviting...
Beautifully Renovated with Parking, Steps to Waikiki Beach!
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...
Your oasis by the sea, stay at B103!
Step off your lanai, & enjoy the pristine ocean, pool, or hot tub. Snorkel with sea turtles & colorful fish. Walk to Kaanapali Beach & boardwalk for casual dining or groceries. Additional shops & restaurants minutes away at Whaler's Village & downtown Lahaina. Papakea...
❤️PiH❤️OHANA Time ★Closer to KaMilo Pools ★Hilton Resort Passes
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Ohana Time, part of our Hawaiian Luxury Collection.Ohana Time at KaMilo is a wonderful 4-bedroom home in the exclusive Mauna Lani Resort.We take great pride in offering some of the most coveted homes on the...
Regency at Poipu Kai 323: Beautifully Updated Poipu Resort Condo With A/C
** Fall 2025 Special Pricing**Welcome to Regency at Poipu Kai #323, your peaceful Hawaiian home away from home. This south shore Kauai vacation rental condo boasts an ideal location in the heart of sun-drenched Poipu, with easy access to the Garden Island’s best...
Polo Beach Club 301 - 2 Bedroom Oceanfront Condo
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies the indoor-outdoor lifestyle that Hawaii is famous for, making it perfect for both entertaining and relaxing with friends...
Remodeled-Ocean Views from Every Window-Great Beach Access-Ac-Well Equipped
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1033 sq. ft) condo that has been completely remodeled with beautiful modern finishes. The condo has ocean views from every window and great beach access as it is right across the street from Kamaole Beach 1....
Aqua Aloha Surf Waikiki 1401 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1401 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed, (1) Queen sofa sleeper, sleeps 4, 360 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
Golf and Beach Paradise! Beautiful townhome🌴
Mauna Lani Beach Club pass included! Enjoy beach towels, beach chairs, and toys.Viking grill on your own lanai!Relax in a peaceful setting at this Mauna Lani Fairways 2-bedroom/2-bathroom, 1300 square foot townhome! The primary bedroom is en-suite and located upstairs...
KM 131 OceanFront Ground Floor Condo w Pool AC Beach
Kauhale Makai 131 Island Style Updated 1Bedroom OceanFront Condo. Ground Floor for Easy Year-Round Indoor-Outdoor Living. Tropical Getaway to Relax and Recharge Aloha and welcome to our charming Maui getaway nestled on the ground floor of the Kauhale Makai Resort in...
Westin Nanea Ocean Villas, Kaanapali Beach, Gorgeous, 2BdRm Ocean view
Large inviting living room, Gorgeous dining room, breathtaking large Master Bd Rm and ensuite bath with a large modern tub, an attractive second bed room with ensuite bathroom. Gourmet kitchen. One large lanai and a second lanai - great for a meal or drinks anytime!...
Summer Special! 10% Discount With 7 Day Stay
Nestled in the heart of Waikoloa Villas, this top-floor 2 bedroom/2 bath condo offers serene views overlooking the Waikoloa Village golf course. Just a short drive away, you'll find the island's best beaches at Waikoloa Beach Resort, along with a variety of excellent...
Ocean views with Hawaiian-inspired decor
E komo mai! Come on in! Papakea J201 offers the best Papakea has to offer with its quiet shady-side location and broad ocean views. J201 is a 1-bed, 1-bath condo that accommodates 2 guests. The large windows on two sides of the living area offer sweeping views of the...
Island Living: Beachfront Penthouse Retreat at Sugar Beach PH#23
Sugar Beach Resort #PH23 – Island Living in a Penthouse Oceanfront CondoWelcome to Sugar Beach Resort #PH23, a beautifully appointed one-bedroom, one-bathroom penthouse condo with panoramic ocean views. Nestled along Maui’s longest stretch of sandy shoreline, this...
Hapuna Beach Residence B21 at Mauna Kea Resort
This magnificent, oceanfront, newly-constructed, island masterpiece offers floor-to-ceiling window walls that create indoor/outdoor living space, a sleek, gourmet kitchen with Wolf and Sub-Zero appliances, double ovens, a cappuccino machine, wine storage and...
Kona Makai 6303: Tropical Retreat 1BR w/ Ocean Views, Pool & Gym
Perched on the top floor of the beloved Kona Makai community, Kona Makai 6303 is a remodeled 1-bedroom, 1-bathroom oceanfront condo with a bonus loft. Featuring sweeping ocean views, breezy lanai dining, and resort-style amenities, this retreat is perfect for couples or...
Kauai Paradise: oceanview 2-bedroom condo with AC and private lanai
Aloha! Welcome to paradise on the amazing North Shore of Kauai.Our 2 BR/2 BA oceanview condo in Emmalani Court - Princeville, offers a comfortable haven to relax after exploring the Garden Isle. It has wonderful ocean and mountain views and a private lanai, cooled by...
Fab Ocean View, largest 1 Bedroom Premium Villa!
Ignite your senses with warm, sunny beach days and dazzling sunsets! Ocean View, Beautiful 1 Bedroom, 1 Bath Premium largest size villa at 900 sq ft, sleeps 4. Parking $35 per day.Full Resort Access. On one of the world's most beautiful beaches!The Westin Kā‘anapali...
Koa Resort 5i-updated 3BR, Pool, Tennis, Hot Tub, Zoned AC, Sleeps 9, pool view
Koa Resort 5i is a rare find—an ideal retreat for families and friends seeking comfort, beauty, and the best of island life. Discover the relaxed luxury of Koa Resort 5i, a beautifully renovated 3-bedroom, 2-bath condo just steps from South Maui’s stunning beaches....
Private Pool. Fully Air-conditioned.
This home is new on the rental market. Previously, it was reserved for our family use only. It has been completely refurbished this year. It is the perfect getaway for those that would like their private pool and is located in a peaceful subdivision close to all the...
The Lodge at Kukui‘ula - Bungalow 4
The Lodge at Kukui'ula, located on the picturesque south shore of Kaua'i, offers a unique blend of luxury and comfort in its Bungalow 4. This one-bedroom bungalow spans approximately 1,275 square feet and is designed with an authentic plantation-style architecture that...
Fairway Villas Waikoloa A21 Includes Waikoloa Gold King Golf Club Membership
Enjoy our 2 bedroom, 2 bath villa for you and your family quietly tucked away along the Big Island's sunny Kohala Coast, Fairway Villas Waikoloa offers the crisp style, gracious elegance, and modern sophistication. Villa has FREE WIFI and PARKING.Come and explore our...
Volcano Rainforest Estate & Lodge; 5 miles to National Park; Hot Tub; 3 BR/3BA<br>11-3203 Huakai Street, Volcano, HI, 96785, United States
ENTIRE MAIN HOUSE RENTALOwner Hosted, owner's cottage is located on the property down a separate drive, privacy for guests in main house.The Volcano Rainforest Lodge is a luxury craftsman house in an ancient forest. We are located only a few minutes from the Hawaii...
An Endless Summer 132- Poipu Beach, Kauai
Located on the most popular beach in Kauai for a reason! Sandy beach and warm ocean water with a large grassy area for lounge chairs for the best sunrise and sunset views! Be as busy or not as you wish..."An Endless Summer" unit 132 is a ground floor end unit taking...
Permitted Luxury Home, Stunning Views, Heated Pool, Perfect Location!
Luxury Home with the Best Views on the Kona Coast (Big Island of Hawaii). We have a STVR (short term vacation rental) permit issued by the County of Hawaii. You'll love our large, heated pool with travertine decking around the pool for the ultimate luxury. Cooks dream...
Maui Resort Rentals: Honua Kai Hokulani 542 - Extra Large One Bedroom w/ Den, Partial Ocean and West Maui Mountain Views!
Hokulani 542 is an expansive two-bedroom, one-bathroom suite boasting views of what West Maui is most famous for, the blue Pacific Ocean and lush West Maui Mountains. With its den converted to a second bedroom, this rare offering provides the space and privacy of an...
Maui Resort Rentals: Luana Garden Villas 16D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3 Bedroom/3 Bath residence is conveniently set within Enclave Three of the Luana Garden Villas. This premiere elevated offering is defined by its southwest-facing orientation with gorgeous views of sunrise skies and the West Maui Mountains. Its...
Gorgeous North Shore Kauai Estate with Saltwater Pool
Bright, cheerful and tastefully designed, this 5 bedroom home sleeps 10 comfortably. Each room has its own unique personality, while the estate is coordinated with aquamarine color schemes, hardwood accents and inspiring details. Cooking for many is an easy task with a...
Aloha Condos, Kanaloa at Kona, Condo 2602, Oceanfront, AC
Hawaii STVR Number: STVR-19-355146 ********FREE CANCELLATION 60 DAYS OR MORE PRIOR TO ARRIVAL***** This is not your “ordinary vacation rental”, but rather a completely renovated, highly upgraded luxury, condo, in an amazing oceanfront location that we rent out on a...
STUNNING OCEANFRONT PENTHOUSE 2Bd/2Ba *Fully Renovated, Pool * Poipu Palms Koloa
This magnificent end unit Penthouse was completely remodeled with everything new just a couple years ago! The Pacific Ocean stretches out as far as you can see in front of you. You often see turtles, spinner dolphins and even whales when they are in season! Enjoy the...
Relaxing Gardens - Peaceful Retreat w/Panoramic Ocean Views
Welcome to our private, peaceful retreat on Hawaii Island's Hamakua Coast - Relaxing Gardens. Unwind and enjoy the panoramic ocean views from our home atop a hill in Laupahoehoe, Hawaii. Our lush gardens will delight your senses with color, fragrance and even a few...
Pualani Villa by Gather: Luxe Princeville Retreat w/ Pool & Hot Tub
Escape to Pualani Villa by Gather, a stunning three-bedroom + den, 2.5-bathroom townhome in the heart of Princeville’s prestigious resort community. Offering a beautifully designed living space, this two-story retreat combines modern luxury with island charm, creating...
Ko Olina Kai 1083C: Contemporary 3BR, Private Lanai, Walk to Beach & Dining
Welcome to Ko Olina Kai 1083C by Gather, a beautifully furnished two story townhome in the gated community of Ko Olina Kai Golf Estates. This island contemporary retreat blends modern comfort with effortless indoor outdoor living, creating the perfect environment for an...
Poipu Sands 513 - Ocean Front with Awesome View of Beach
Summary:True oceanfront ground-floor retreat with unobstructed views of Shipwreck Beach and the Pacific. Poipu Sands 513 offers a private lanai, direct greenbelt access, and front-row seats for sunsets, whales in season, and crashing waves. Walk to Shipwreck, Poipu...
The Makai Manor - Beautiful Newly Built Spacious Home
This newly constructed home made it's grand debut August 2021. We are pleased to invite you to this stunning property. The home is located next to a beach park and has gorgeous ocean views. The neighborhood is quiet and extremely family friendly. Everything you will...
Amazing Hotel Zoned Beach Front Condo on Sugar Beach. Reserve with Confidence!
Ready for a beach vacation in paradise?!? Beach front complexes on the south shore of Maui are generally not this close to the shoreline and most are apartment zoned and may be subject to recent proposals to convert to longer term housing rentals. Nani Kai Hale is hotel...
Ocean front studio condo w/views of pool, ocean & Sleeping Giant Mountain
Great location in Kauai's Coconut Coast especially for sunrises over the ocean from your private balcony. This cozy 2nd floor corner unit condo offers guests a retreat with a king bed, views of the ocean, pool & Sleeping Giant mountain. Its sturdy cynderblock...
Maui Resort Rentals: Honua Kai Konea 929 – 9th Floor 3BR W/ Stunning Ocean Views from All 3 Bedrooms!
This exquisite three bedroom oceanview residence boasts epic views of the Pacific Ocean from its premier 9th-floor vantage point, well above the tropical foliage of the Konea Tower interior courtyard. The views are abundant throughout and even continue into all 3...
Tranquil cottage in peaceful Kohala farm setting
This studio cottage sits on 5 acres of orchard, gulch and gardens with the Kohala coast as a backdrop. The owners farm the back 20 acres with cattle, sheep, goats and chickens. We are located midway between the towns of Hawi and Kapa'au--both known for their quaint...
Corner Unit 1 Block to Beach in Heart of Waikiki! FREE Parking & Wi-Fi, AC!
Ni'ihau Apartments #605 – 247 Beach WalkLocation, location, location! Ni'ihau is a hidden gem found within the hustle and bustle of Waikiki just a block away from world-famous Waikiki Beach where surfers and paddlers spend their days! Beautiful corner unit (673 sqft)...
Brand New Luxury Maui Kamaole Condo Grd Flr D112
Mana Hale, Maui Kamaole D-112 is a totally renovated gorgeous ground floor, 1 bed 2 bath partial ocean view condo. It features a full kitchen, brand new air conditioning system, new amenities including large screen TV, Roku players, washer/dryer, workstation, and...
Wailea Ekolu 505 ~ Big Ocean Views ~ New Furnishings
Spectacular Ocean and Sunset Views!!A short walk or drive to Wailea’s best beaches.Newly furnished and well appointed home will provide an exceptional experience.Wailea Ekolu is peaceful and spacious development with dinning, coffee, shopping and Maui's best beaches...
Pualani Hale: Upcountry Maui Villa with Breathtaking Views
Aloha, sorry but at this time we are not hosting to families with children younger than 12 Mahalo.PermitsBBMP2019/0006 & SUP2 2019/0003GE-081-730-0480-01 & TA-081-730-0480-01This is a BnB not a STRHOwners live on property.We encourage you to respectfully enjoy our...
Newly Updated Alii Kai Princeville Condo w/ Yard & Stunning Views
NEW LISTING: Located in the Ali`i Kai Resort in picturesque Princeville, this newly-renovated, modern condo offers 2 bedrooms with Cal King and Queen beds, 2 full baths, washer and dryer, a spacious living room, well-appointed kitchen, and dining area. The condo is on...