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.
Royal Kahana Maui 120 Garden View 2 Bedroom 2 Bath
This inviting two-bedroom garden-view unit provides a serene setting surrounded by lush greenery, ideal for families or small groups looking to unwind while staying close to Maui’s beautiful coastline. Unit 120 Garden View 2 Bedroom 2 Bath• First floor condo in a garden...
Amazing views! Exclusive & peaceful Hawaii Kai. Walk to ocean & hikes, Pool, AC,
A pristine, quiet neighborhood on the backside of Hanauma Bay, your Honolulu/Oahu adventure begins at this lovely 4-bedroom house. With 2 king beds, 1 full bed, and 1 queen bed, this newly rebuilt property is perfect for families or small groups of friends. Three of the...
Deluxe Garden View w/WiFi & A/C-Maui Banyan
Maui Banyan T108A: Tasteful artwork, chic floral patterns, and rustic island color tones set the mood in this wide-open 1st-floor unit that boasts sleek hardwood flooring and oversized garden-facing windows. The functional layout is furnished with premium furniture that...
Hale Nalu (Lower Level) by Gather: Oceanfront w/ Lanai, Grill & Views
At Hale Nalu (Lower Level), the Pacific Ocean stretches out from your backyard while the famous beaches of O'ahu’s North Shore frame your days. This three-bedroom, two-bath home offers relaxed beachfront living with its own full kitchen, living spaces, and covered...
Peaceful Ground Floor Unit- Hale Kaileia Kai with Infinite Pool & Hot tub
Welcome to your serene island hideaway at Fairway Villas #C2, in the beautiful Wāikoloa Beach Resort on the Kohala Coast. This spacious 2-bed, 2-bath ground-floor villa (1,170 SF) blends modern comfort with relaxed resort living. Enjoy golf course + Mauna Kea views from...
Stunning Studio w/Pool & Includes Free Dedicated Parking Space
Welcome to this charming studio in Honolulu. Guests will find a tremendous living area featuring a comfortable queen bed and sofabed (for 3rd guest), perfect for relaxing after a day of exploring. The bathroom includes a refreshing shower and a handy hair dryer for...
Ideal Long term remote work space close to the beach
Enjoy the sound of the birds and the convenience of being in Lahaina. Workout facility, community pool and short walk to the beach. Spacious kitchen with eat in counter. Van also available for additional fee and long term rentals. Pet friendly community.
KBM Resorts | FREE CAR | Napili Point | Oceanfront 1-Bedroom Condo with Luxury Amenities! NAP-B26
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Live Local Redwood Pole house panaramic Ocean views quiet convienent nbrhood
. Wailupe is on mountain side , 5 blocks facing ocean. enjoy tennis, bball/park across street, great views. Convenient location to town, Waikiki 4 miles away. Two bedrooms in large great room. Main bedroom has a queen size bed, sons room has a twin, and living room has...
2 Bedroom Premier (2BX) at Grand Waikikian, a Hilton Grand Vacations Club
Step into the tropical oasis of The Grand Waikikian by Hilton Grand Vacations Club and prepare for the Hawaiian vacation of a lifetime! Nestled within the renowned Hilton Hawaiian Village® Waikiki Beach Resort, this upscale resort offers a perfect blend of island charm,...
Maui Resort Rentals: Honua Kai – 4 Total Bedrooms + Den w/ Beautiful Ocean & Mountain Views!
Unquestionably one of Honua Kai’s best values, this exceptional 4BR plus den offering combines two neighboring partial oceanview suites with an adjacent mountain view suite. Together, the residences provide the perfect retreat for large groups or families seeking a...
Kaanapali Alii Residence 464
Ka’anapali Alii 4643 Bedrooms | 2 Bathrooms | Sleeps 5 | Ocean View________________________________________Welcome to Kaanpali Alii 464, a gorgeous two-bedroom condo with a fully enclosed den that serves as a third bedroom. This coastal-inspired residence offers a...
Aqua Aloha Surf Waikiki 209 Moderate Studio with Partial City Views, Sleeps 2
Aqua Aloha Surf Waikiki 209 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 219 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
Maui Resort Rentals: Kaanapali Alii - 4BR Retreat with Ocean and Mountain Views!
Suite 241 is ideally situated within one of the resort’s most desirable interior columns, showcasing sweeping views of the Pacific Ocean, the island of Lanai, and the impeccably landscaped Kaanapali Alii grounds below. These captivating vistas extend effortlessly...
Ocean View Queen Room at Kaimana Beach Hotel | Right on the Beach
Nestled between the iconic Diamond Head and Waikiki Beach, Kaimana Beach Hotel combines coastal charm with easy access to local attractions. The Ocean View Queen offers partial ocean views and a relaxed island atmosphere. It's a perfect hideaway to watch the waves and...
2BR+Den High Floor Ocean View Free Parking
Enjoy ocean and city views from this spacious 2BR+Den condo 798 sqft/74 sqm at high floor with floor-to-ceiling windows. Save $$$ with secured free parking in the building plus free wifi and fully equipped kitchen. Walk to the best restaurants and bars, Chinatown, and...
Amazing Kauai 2 BR Condo Ocean View Location ~ Beautiful Interior ~
BEAUTIFUL Princeville, KAUAI, check-in, Saturday to Saturday: This is paradise on a bluff -Amazing Ocean View ~ Amazing Location ~ Amazing Interior ~ • Paradise Found..! Surrounded by Lush Tropical Landscape ~ On a bluff on the north shore of Kauai, The Cliffs Club...
Just Listed! Oceanfront Paradise Views and Luxury
Relax and replenish at this lovely and clean hotel room at the sought-after Outrigger Kauai Beach Resort. Situated with amazing views of the pools, ocean, and tropical paradise of the unmatched landscape . See the sunrise from your private lanai over the Pacific while...
Wyndham Makai Club Cottages|Two 2BR/2BA Suites - Sleeps 12!
Summary:Explore all the beauty, fun, and heritage of the “Garden Island” from your private cottage, situated serenely along the first fairway of the Trent Jones-designed Makai Golf Course in beautiful Princeville.The Space:This listing is for two suites at Club Wyndham...
Kapalua Ridge Villas | Ocean Views, Grass Lawn | KBM Resorts | 2 Units, 3 Bedrooms | ML-2516
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kihei Condo 8-363 - Steps to Kam II Beach and Sunsets
Welcome to your perfect Maui getaway at Kihei Kai Nani 8-363, where Aloha Chic design meets stunning sunset, sunrise and mountain views. This thoughtfully appointed 1-bedroom condo is at the back of the property, furthest from the main road, making it more peaceful....
Waikiki Compact Family Room 10Guests /2 Studio/ 2Full bathroom
This Waikiki Sudio/condo, nestled against an iconic backdrop, is truly one of the area's hidden gems! Close to everything, it offers modern accommodations, canal views from its upper floors, and free access to condo amenities: an outdoor pool on the 6th floor and...
Enjoy this 18th-floor 1br apartment with stunning ocean and Diamond Head views!
This newly renovated 18th-floor 1br apartment is the perfect retreat for up to 4 guests, offering beautiful diamond head, ocean and city views in the heart of Waikiki. Just a short stroll from world-famous beaches, you’ll be swimming, surfing, or snorkeling in no time....
Waikiki Gem! Renovated, Steps Away From The Beach!
Prime location and fully renovated studio! Revel in vibrant hues, new furnishings, and a lanai offering a peekaboo ocean view. Enjoy comfort with a kitchenette including basic cooking utensils and a luxurious bathroom. Explore our modern oasis, ideally located within...
Waipouli Beach Resort Courtyard View 1 BD 2 BA
Courtyard View 1 Bedroom 2 Bath- Spacious condo offers full kitchen to include granite countertops and includes Wolf cooktop and convection oven, microwave, 2-drawer Fisher-Paykel dishwasher, full size Sub-zero refrigerator, coffee maker, blender, toaster, cookware and...
Beachfront Condo at Makaha Beach Cabanas
IMPORTANT UPDATE:The rate has been reduced to account for the construction occurring outside the building. During the weekdays, there is intermittent noise from the outside construction. There is no construction on the weekends. Construction on the building will...
Aqua Aloha Surf Waikiki 1208 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1208 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, 365 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
Charming Coconut Plantations 2/2.5 Townhome in Ko Olina Resort Community
Situated on the 13th fairway of the famous Ko Olina Resort, overlooking a beautiful pond inhabited by the graceful Ko Olina black swans, this fully furnished single level, 2 bdrm, 2.5 bath home feels like your own private oasis in an exclusive gated community. This...
5BR Ocean View Home close to shopping, dining, beaches
Welcome to Kainani Vacation Home 10- where trade winds, golden sunsets, and effortless island living come together in one stunning home. With ocean and golf course views, nearly 4,700 square feet of indoor-outdoor living, and a layout designed for gathering, relaxing,...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Large Master Suite | 2 Units, 3 Bedrooms | ML-2017
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Royal Kahana Maui 410 Oceanfront 2 Bedroom
Step into your oceanfront two-bedroom retreat with expansive views of the Pacific, just moments from the beach. Ideal for families, couples, or friends seeking a memorable Maui escape. Unit 410 Oceanfront 2 Bedroom 2.5 Bath• 4th floor condo with large balcony with views...
Regency 620 - Beautiful 3 Bedroom Overlooking Regency Pool
REGENCY 620 AT KOLOA KAI VACATION RENTALSSpacious Top-Floor Home in Poipu Kai ResortEscape to sun-soaked Poipu Kai Resort and enjoy the island lifestyle at Regency 620, a beautifully appointed three-bedroom, three-bath vacation home just a short stroll from Poipu Beach...
Comfortable, Spacious with Great Location in Waikiki!
1 Bedroom Ocean View on the 9th Floor of Discovery Bay! Fully equipped and furnished condo with complete kitchen including dishwasher and built-in microwave. Unit has been recently updated with new furnishings and artwork and new refrigerator and range. The remodeled...
Oceanfront Bliss at Makani A Kai, AC Included!
Welcome to Makani A Kai Unit A8, your perfect Hawaiian retreat nestled on the tranquil shores of Maalaea Bay in Maui. This charming 1-bedroom, 1-bathroom beachfront ground-floor condo offers a serene escape with all the comforts of home, ideal for couples or small...
The Spirit of Aloha-1Bed/1Bath in Tropical Resort
Located in Kihei, this welcoming apartment lets you experience it all. There's convenient onsite parking, so you can leave your vehicle behind and head out to Maalaea Bay Beaches and Kalepolepo Beach Park, just a short walk away. Relax by the outdoor pool or sip a drink...
Kaanapali Alii Residence 466
Kaanapali Alii 4662 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 466, a beautiful two-bedroom condominium in Maui’s exclusive Kaanapali Alii Resort. This 1,788-square-foot residence offers stunning views...
Stunning Luxury Family Estate in Kona
In 1998, the Lenett family decided to purchase a plot of land on the beautiful Big Island of Hawai’i, after years of visiting as tourists. The Lenett's, natives of San Francisco, fell in love with the island’s natural beauty, tropical weather, and kind people. For the...
301 - 2 Bedroom end-unit with Breathtaking Ocean Views!
This third floor oceanfront condo at the Kihei Surfside Resort is located at the ocean end of the building. The end units of 2 bedroom condos boast the closest proximity to the ocean in all of Kihei or Wailea.It has a spectacular 180 degree view from the kitchen, living...
Ilikai Hotel Lite #1836: Studio Ocean View condo
**PROPERTY PROJECT**Ilikai Hotel Spalling and Exterior Painting ProjectAn exterior painting and spalling repair project to enhance the building’s structural integrity and appearance with minimal disruption will commence on August 18, 2025. Work Schedule: 9 AM – 5 PM,...
Panoramic Ocean View condo with AC, WiFi in beautiful Waikiki
Right in the heart of Ala Moana corridor, 1 block to the beach. Everything is walkable: Waikiki Marina, Magic Island, Hilton Lagoon, Ala Moana shopping mall. Gorgeous Sunset view and Friday Night Fireworks!
Honua Kai Hokulani | 2 Free Rental Cars | KBM Resorts | Amazing | 2 Units, 4 Bedrooms | ML-1323
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Ocean view 2-bedroom condo at Kaanapali Shores 903, Lahaina, West Maui.
Kaanapali Shores 903 Beautiful Blue Ocean Views from this 9th Floor North Kaanapali Condo Just an Elevator Ride to the Beach, Pool, & JacuzziWelcome to your Maui Retreat: Kaanapali Shores 903 is a freshly updated 2-bedroom, 2-bath penthouse perched on the top floor of...
Honua Kai Konea | 2 Free Rental Cars | KBM Resorts | Massive Lanai | 2 Units, 3 Bedrooms | ML-1433
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Waipouli Beach Resort Garden View 2 BD 3 BA
This inviting two-bedroom condo overlooks beautifully maintained gardens, creating a calming setting for your Kauai getaway. Perfect for a family to enjoy the nearby beaches and attractions.Garden View 2 Bedroom 3 Bathroom• Kitchen features granite countertops, Wolf...
Cute Kihei Akahi Studio - Recently Renovated and Close to Beaches
Aloha! Our recently renovated studio is located within the very desirable Kihei Akahi Condominiums.The studio is located in the 'C" Building on the 5th floor, and was renovated in March 2018.You will find new floors throughout the unit, granite countertops in the...
Cozy, clean, and comfortable condominium home in wonderful Kona!
Be truly at home here! Stretch out. Eat good food. Relax. Sleep well. Then, go maximize your fun time! Exhaust yourselves at Kona’s world renowned beaches. Hike until your shoe tread gives traversing the mauna. Or, if in fact, your experience includes the words, “big...
Rustic retreat with panoramic views at Pu'u O Hoku Ranch
Pu'u O Hoku Ranch offers a unique getaway for travelers seeking a rustic retreat. You can hike, swim, stargaze, and see a working ranch in action. Pu'u O Hoku is one of the few places in the islands where you can feel Hawaii as it once was. The Sunrise cottage is just a...
1-bedroom condo across from Kahana Beach
Our 1 bedroom has all the perfect amenities and conveniences for yourself or your guests. Enjoy the cool Kahana breeze and peekaboo ocean views from your private patio. Take a short walk to Kahana Beach located right across the street. Kahana Manor is a mixed-used...
Ocean View Studio at Marriott’s Maui Ocean Club – Beachfront Paradise
Discover island comfort and breathtaking views in this Studio Ocean View Villa at Marriott’s Maui Ocean Club – Molokai, Maui & Lanai Towers, located along Kaʻanapali Beach. This well-appointed studio accommodates up to four guests and is ideal for couples or small...
2 Bedroom Ocean View - Gold
Kaanapali Alii 2952 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Experience the warmth of Hawaiian hospitality in Kaanapali Alii 295, a beautifully appointed two-bedroom ocean-view residence featuring classic Hawaiiana décor,...