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.
Beautiful Poipu AC, Walk to Beach, Pool and Tennis KP117
PROPERTY DESCRIPTIONWelcome to Sunny Poipu Beach! This newly remodeled Kiahuna Plantation leaves nothing to be desired! Relax on your private lanai overlooking the garden while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips....
Remodeled 1bd, stunning sunsets & views
Nestled on the 3rd floor, Valley Isle 305 is a charming 1-bedroom, 1-bathroom condo that offers direct ocean views and ceiling fans throughout. This resort has elevators for easy access. Unit 305 can accommodate up to 4 guests. The master bedroom features a king-size...
NEW Listing: Special Rate - Mauna Kea Fairways South 22 - Dreamy Hawaiian Escape
Special New Listing Rate!Welcome to Mauna Kea Fairways South 22, where elegance meets contemporary comfort in a tranquil setting with breathtaking ocean views. Our *fully remodeled* 3,800sqft vacation rental is designed for peace and luxury, offering a haven for...
Hale Oka Nunu: Oceanfront Private, Spacious Paradise North Shore Home w/ Hot Tub
Hale Oka Nunu is a four-bedroom, three-bath oceanfront retreat on O’ahu’s North Shore, where the Pacific is just steps from your lanai. Designed for both relaxation and connection, this single-level home blends open living spaces, gourmet amenities, and sweeping...
Ocean Views ! Excellent Proximity to Hualalai Resort Amenities ! Includes Golf Cart
Located in the Award Winning Resort Community of Hualalai Four Seasons.Beautiful ocean views from this delightful two bedroom Garden Level Villa. Spacious Lanai with lounge seating extends seamlessly to a large lawn area. Enjoy the sounds of the ocean and glances of the...
Includes Hilton Waikoloa Pool Pass thru June 2025. Halii Kai 10G
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 10G. Ocean Views! Recently Updated in 2025!Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Queen BedLiving Room:...
Best in American Living Award Winner! Resort Villa, Short Walk to Beach
BEST IN AMERICAN LIVING AWARD WINNER!Welcome to Laule'a 6 at Mauna Lani Resort. Located within a brand new project (2018) which boasts the best of luxury and convenience located at the world-class Mauna Lani Resort on the Big Island of Hawaii. This exclusive community...
Exceptional Oceanfront Luxury Condo - Fully updated, AC, Top Floor, Quiet
Absolute direct oceanfront top floor, two-bedroom condo located in the heart of Kailua-Kona, Hawaii.Step inside and take in stunning ocean views from your private balcony—welcome to paradise!AC in all spaces, fully updated with high-quality furnishings throughout.From...
Sunny Family Oasis ☀ Tree House, Trampoline, Games, Toys
Single family residence with front and back yard. Wonderful trade winds keep the house cool and fresh year round. Relax on either of the front or back lanais. The house is stocked with all the necessities for the best possible stay in Princeville, Kauai. You will have...
"Coconut Crest Cottage"
"Coconut Crest Cottage" is a perfect tropical getaway for families, small groups, or visitors to BYU-Hawai'i. Nestled in the heart of Oahu's North Shore within convenient proximity to the ocean and the iconic Kahuku Sugar Mill, featuring numerous food trucks. Turtle Bay...
Ocean View Condo at Foster Tower Across from Beach w/Great Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Foster Tower located at 2500 Kalakaua Ave on the 14th floor.Welcome to The Foster, perfectly situated in...
4 Bedroom with Private Pool and Spa in Waikoloa Beach
Welcome to Ainamalu Breeze, where mainland cares and day-to-day worries are carried away to provide you the sanctuary you have desired. When you enter our exquisite property, you leave the mundane tasks of travel and are released into a world of luxury. Upon entering...
Kamaole Sands 4-213 - Beautiful Modern Renovation - Bright & Open - Split AC
Freshly remodeled throughout including a gourmet kitchen, Kamaole Sands 4-213 has been thoroughly updated to “second home” standards by its owners. Every guest convenience has been anticipated and addressed in this bright, open corner unit (more windows, more light,...
Private Penthouse Getaway At Waikoloa Beach Resort 5 minutes from A-Bay Beach
Beach Access, A-Bay Beach, a 5 minute drive. Our beautiful luxurious two-bedroom, two-bath penthouse condo located in a private gated community. Enjoy your vacation in a tropical paradise at the Waikoloa Beach Villas. From our third floor, enjoy beautiful mountain and...
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
GE: 184-440-0128-01TAT: 184-440-0128-01Aloha and welcome to the Hale Anna, Maui. The Hale Anna is a beautiful, private home located across a quiet street from miles of sandy beach. This home is a legal grandfathered vacation rental with the Maui County Department of...
Awesome Top Floor Unit with Amazing Views of Ocean and Pools
This beautiful, renovated 2 bedroom condo, is in the perfect location on the top floor of the Anthurium Building. It is an ocean front corner unit facing southwest; so the lanai is not exposed to the direct strong trade winds of the north side of the complex. The views...
Ocean View, Very Clean, Updated 1 BR Condo Steps from Beach, Shops, Restaurants
If you are looking for a well kept island-feel condominium at an affordable price, our unit, located 100 yards from the ocean, will not disappoint. Our beautiful second story condo is located in building 1 at the Kihei Kai Nani Resort. It has great ocean and beach views...
Kahalu’u Surf and Snorkel Beachfront Paradise, with Hot Tub
Incredible views of the bay and surfers! Modern house(built 2014) with A/C, across the street from Kahalu’u Beach. This is the BEST snorkeling and surfing in Kona. Surfboards,The Kona Trolley stop, and food trucks are steps away. The house has a hot tub, 4 bedrooms,...
Modern, serene condo + lush views and top-notch amenities at Grand Champions #29
Modern and sophisticated with a splash of Aloha, #29 is an ideal spot for honeymooning couples and those returning for their tropical anniversary celebration. Tucked in the lush foliage at the back of Grand Champions, this condo has the unique feature of being in one of...
Aloha Sands: Luxury Hawaiian Villa - Puako Beachfront
5 STAR REVIEWS! STUNNING VILLA! TASTE OF OLD HAWAII ON THE BEST BEACH IN PUAKO! This lofty and spacious Hawaiian villa lies on the Gold Coast of Hawaii, the sunniest spot in the state. Aloha Sands is also on the best sandy beach in Puako between the Mauna Kea and Mauni...
Jungle Retreat in Kona Cloud Forest Sanctuary, An unforgettable Cloud Forest Sanctuary retreat exper
Wake up in your cozy private jungle retreat immersed in the lush serenity of the Kona Cloud Forest Sanctuary. During your stay in our Sanctuary, experience our guided forest tours, yoga, sound baths, and more. Enjoy a morning walk for fresh brew and coffee tours at...
Located Directly on the Oceanfront with Spectacular Views
Aloha! Please enjoy the following photos of this wonderful condominium. I know you will enjoy your stay with us. Our private residence has one of the most spectacular views on the island. This vacation home is directly on the oceanfront and is a bottom floor unit. This...
LUXURIOUS POIPU SANDS CONDO SANCTUARY
You're invited to experience the 'ALOHA' spirit in this completely renovated, nearly 1000 sq. ft., one bedroom, one and a half bath luxury Poipu Sands Condo. Situated in Building 4 of the complex, our unit is among the closest to Grand Hyatt Resort and Spa, Shipwreck...
Remodeled ground floor Kihei studio with AC across from beachnn
Welcome to Kihei Bay Surf 140. This completely remodeled ground floor studio has all the comforts of home. Feel right at home in this quaint coastal styled condo that can accommodate 3 people with the window AC unit, sofa sleeper, and ceiling fan. Pool, spa and tennis...
'My Favorite Place on Earth'
This is the Hawaii you dream about! This little bungalow on the beach is an ideal tropical vacation destination for a couple or a family with children. It is the perfect island get-away for Honeymooners. The house and lanai open to expansive views of the beach, ocean...
BEACHFRONT KUHIO SHORES POIPU GORGEOUS OCEAN VIEWS 10 STEPS TO WATER FROM CONDO
Ready to relax to the sounds of the sea? Here is your amazing beachfront condo just steps to the water, located on the beautiful island of Kauai. This amazing oceanfront Kuhio Shores villa is located in Poipu on the south shore of Kauai. Our building is rare because It...
Luxury And Aloha Await You! Relaxation, Great Snorkeling, Large Unit
South Kona Hideaway is near some of the best snorkeling Hawaii has to offer. We are situated between Honaunau (Place of Refuge) and Kealakekua Bay at an elevation of 900 ft. Your beautifully decorated suite has a living room with a queen sofa bed, large flat screen...
Well Equipped, Local Art, Private, Near Pool
Aloha to your peaceful Waikoloa retreat - a relaxing island escape for families, couples & small groups exploring Hawaii’s Big Island:- Sleeps 5 | 2 bedrooms | 3 beds | 2.5 baths- Shared pool, hot tub & fitness room- Private lanai w/ outdoor dining- Fully equipped...
Breathtaking 180-Degree Ocean Views, Ilikai Marina, Full Kitchen!
Construction Notice 10/20/25: Exterior painting work is currently scheduled from 10/29 - 12/12/2025. During this time, the lanai will be locked and not accessible to guests. For your safety, please do not attempt to use the lanai at any time. You may also hear...
OCEAN FRONT top floor/penthouse 2bd/2ba + Loft + gorgeous lanai VIEWS & SUNSETS!
Return to Maui! 🩵Aloha! Welcome to Papakea and this beautiful OCEAN FRONT - 2 bedrooms, 2 bath + loft. The property is located within minutes of both Whaler’s Village and Black Rock and resides within a 13-acre resort like property. This “penthouse” style...
Hilton Pass, Poolside Villa w/BBQ, Ground Unit, BOB Stroller, Sleeps 6, D3
2025 check ins receive a bottle of sparkling to start vacation out right! This poolside paradise is within Waikoloa Beach Resort area - a perfect destination for your next vacation. Unit also includes access to the Hilton (just down the street) so you can enjoy resort...
Kailua-Kona Condo w/ Pool & Ocean Views
A tropical Hawaiian getaway awaits your arrival at this updated Kona Coast condo perched above Keauhou Bay! Upon entering the unit, guests of this 2-bed, 2-bath property are treated to a quintessential island experience with a contemporary flair. Whether guests spend...
Ocean + Skyline Views: Honolulu Retreat
1,400 Sq Ft | Walk to Wa'Ahila Ridge State Park | Connects to State Park Trail SystemEnjoy your island vacation in comfort at this picturesque Honolulu vacation rental. This 3-bedroom, 2-bath home features mid-century modern touches, a breezy lanai, and a living room...
Rainforest Retreat w/Outdoor Fireplace & Hot Tub
Located 10 minutes from Volcanoes National Park, come spend your days exploring, hiking, golfing or simply relaxing in our unique, tranquil setting. This beautifully crafted home has all of the amenities and comforts you need. From soaking in the large hot tub to making...
Ocean view, best location in Kapalua, walk to beach, remodel
Welcome to the luxurious fully remodeled Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a...
3 Bedroom Ocean View Townhome
The main living area of Halii Kai 11F has two luxurious soft sofas facing an armoire with a SMART TV and a DVD player. Adjacent is the dining area with a large table seating 6. The large kitchen has a wrap around granite counter with 3 bar stools and stainless steel...
Gorgeous two-level condo with resort-style pool & hot tub - close to beach
Ka Pu'uwai at Nihilani 29BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A lush exterior, with a gorgeous resort-style pool and hot tub, and a bright, modern interior with two...
Ko'Olina Retreat - Short Walk to Resorts, Golf, Restaurants & Lagoons!
Welcome to your dream retreat in the heart of Ko'Olina! This beautifully remodeled 3-bedroom, 3-bathroom townhome is nestled in the exclusive, gated community of Ko'Olina Kai, offering the perfect blend of luxury, comfort, and island charm.Step inside and be captivated...
Mahana Beachfront Walkout
Maui Gov’t Approved Short Term Rental. We are the owners (Barry Travers and Rhonda Anderson) of Mahana 118 and we own several Maui properties with hundreds of 5 Star reviews for our properties as we provide the ultimate guest experience! Mahana 118 is an AMAZING...
New!-#510-Ocean-Sunset Views! Steps from It All!
*For bookings with arrival dates during November 2025, we will donate money to the Maui Food Bank to feed a family of four this Thanksgiving*Ocean-View Condo with Double Lanai & Rooftop BBQ | 2BR/2BA | Steps to Beach + DiningWelcome to your Maui retreat at Kamaole Beach...
🌊 EPIC Oceanfront Condo at Hale Kona Kai #403, TOP FLOOR, ELEVATOR, CENTRAL AC 🐬
Aloha and welcome to KONA TIPSY TURTLE at Hale Kona Kai #403. This is the absolute destination should you want a relaxing vacation getaway on the Kona coast. The location of this condo complex adds convenience as fun activities and amenities are within walking distance....
Bamboo Canopy with Shared Bath and Common House
Escape to the enchanting Bamboo Canopy, a glamping-style retreat. This unique accommodation offers the perfect blend of rustic charm and modern comforts, making it an ideal choice for those seeking a tranquil yet luxurious getaway.The Bamboo Canopy features a queen-size...
Magnificent Views of the Mighty Pacific Ocean from Every Room
Enjoy the beautiful North Shore of Kauai at our lovely Alii Kai I Condominium. It is a ground floor, corner unit sitting on a bluff overlooking the magnificent Pacific Ocean. In the winter be mesmerized by 15 to 25 foot waves. Whales cavorting in the ocean and...
Gorgeous 3b/2b house minutes from Natl Park & Volcano Village. Family friendly!
Tree Fern Escape is a cozy and comfy getaway just minutes from the Volcano National Park. This 3 bedrooms, 2 baths charming property, has gorgeous hardwood floors, newly furnished with large private backyard. Large enough for big families, cozy enough for couples.Large...
Steps from Paniau Beach
House or Cottage or both together(see listing #956147 for Cottage) PLEASE NOTE... Listed rates are based on two guests. An additional $50/per nt per extra guest will be added. Please enclose total number of guests when booking......Located at the private and quiet end...
Watch for albatross and nene from ocean view beauty
Located on the North Shore of Kauai in Princeville, Ka Mea Nui is surrounded by lush tropical landscapes overlooking the Pacific Ocean and the 15th hole of the Makai golf course. The verdant golf course is a favorite playground for endangered nene (Hawaiian geese) and a...
Maui Resort Rentals: Kaanapali Ali'i – Oceanfront Ground Floor + Yard Area, 4 Total Bedrooms+DEN, Sleeps 14
This one-of-a-kind Oceanfront 4BR+DEN ground-floor offering at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach is comprised of two luxurious adjacent suites. Together they offer a massive 5,188ft of combined interior living area and a sleeping capacity of...
Waikiki Beach Penthouse
Located just a block from Waikiki Beach and surrounded by top-tier hotels, this gorgeous penthouse condo offers the style and comfort of a luxury hotel with the added benefits of 1700+ square feet of living space, a large well-appointed kitchen, extra-large private...
Makanui 711 - Garden/Mountain View
MAKANUI 711 AT KOLOA KAI VACATION RENTALSYour Charming Beach Oasis in PoipuWelcome to Makanui 711, a delightful 1-bedroom, 1.5-bath condo offering a perfect retreat in the heart of Poipu. Located just a short stroll from Poipu Beach, Brennecke’s Beach, and Shipwreck...
Beautifully remodeled Sugar Beach #104, meticulously cleaned and maintained
Welcome to our beautifully remodeled ground-floor condo at Sugar Beach Resort #104 in North Kihei! Experience island living in this beautiful condominium situated along Maui's 5 mile Sugar Beach. With direct access to one of the longest stretches of sandy beach on the...