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.
NP B28 March price drop! 1BR gorgeous, private spot, full AC, well stocked
Whether your idea of the perfect Hawaii vacation includes snorkeling, surfing, golfing, paddle boarding, hiking, or just relaxing on the covered lanai, by the ocean or by the pool with a good book, Napili Point condo B-28 is your perfect home base. Our luxurious and...
WOW! WHALER's BEST-10th Fl. 1 BR- SLEEPS 6 -PANORAMIC Ocean Views 365 SUNSETS!!!
Unit 1059 is truly one of the absolute nicest 1 bedroom units at the Whaler. Unit 1059 is on the 10th floor and has one of the most spectacular views anywhere in Kaanapali. This total remodeled and professionally decorated 10th floor suite is one of the VERY nicest one...
Honua Kai Luxury in Paradise 2BR / 2BA Sleeps 6
Aloha! Welcome to our suite at the Honua Kai Resort and SpaUnit 212 Hokulani TowerWe do not charge a resort or parking fee. The quote listed is all in.We also have a 1 BR available in the same building one floor below. See VRBO # 1308715. One minute walk down the...
Puuwai Alii Estate: Stunning Luxury Home with Pool, Hot Tub & Ocean Views,AC!
Absolutely amazing property! A one of a kind 5-bedroom, 6-bathroom property that is built to impress with gorgeous high end materials and is one of just seven properties in the quaint "Pu'uwai Ali'i" subdivision. The gated entrance, majestic surrounding trellises, and...
Lowest Rates-Amazing Romantic Getaway- Studio On top of the ocean-Cold AC
Fall in love with The Hula Hideaway—a newly remodeled oceanfront studio just 10 feet from the water in Kahana, Maui. Enjoy stunning sunsets, whale watching, and island views from your private lanai. Includes king bed, full kitchen, AC, Wi-Fi, washer/dryer, and beach...
Kaulana Naue – Luxury Beachfront Home on Kauai’s North Shore
Exclusive Luxury Beachfront Home located around the point from Tunnel’s Beach. More secluded not so populated gorgeous beach which is just a beach walk from Tunnels.Imagine an island, a lush green paradise in the far-off reaches of the deep blue sea. Mango trees sway...
Fresh, Bright, New! Near Hanalei. Walk to the ocean in minutes.
Aloha and Welcome to Hale Honu O Hanalei ~ House of the Turtle.This hidden jewel sits on the ridge above the Hanalei Valley on Kauai's tropical North Shore. Tucked away on a quiet side road, and walking distance to one of the North Shore's best-kept secret beach trails....
5★Tropical Oasis, Heated Pool, Waterfall, Gazebo, OceanView,❤️of Kona,NEW Remodel
Located in a quiet, gated community, this house ticks off all the boxes. Located all on one level, there is room to spread out with the primary bedroom separated by a lovely open living/kitchen area from the second and third bedrooms. New furnishings and appliances...
Bright & modern dog-friendly oasis on two lush acres with generous patio & W/D
Orchid Land | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to paradise in this charming, newly built home in Keaau, Hawaii available for long-term stays....
KOLEA 6D ~ OCEAN VIEW GARDEN HOME
Welcome to Kolea 6D ~This 3 bedroom, 3 bathroom condo has a prime location just steps from the Kolea Beach Club. While it offers the convenience and ease of access to a large 3 bedroom home, it is extremely special as you wont need to sacrifice enjoying a lovely...
Pukalani a Marriott Grand Residence
Our second home is located 100 feet above the Pacific Ocean, with mountain views across the bay, and two ocean front golf holes of the 18 hole Jack Nicklaus, now called Hokuala, golf course in front of you. Even the back door has a great view of the 38 acre Kauai...
Christmas 2023 Maui! 2 Bedrooms-Sleeps 8-Dec 22 thru Dec 29 Friday-Friday
This year make it a very MAUI CHRISTMAS!!For years MAUI HAS BEEN VOTED #1 ISLAND IN THE WORLD. Come see for yourself...All of the amenities of a resort, with the comforts of home! The Westin Ka'anapali Ocean Resort Villas is all about the details, which makes it such a...
Kaanapali Alii | 445
Natural light and colorful garden views fill the residence of Kaanapali Alii 445. This two-bedroom vacation condo steps from Maui’s famous Kaanapali Beach is the perfect retreat for the dream Hawaii vacation. Modern features like wood flooring, stainless steel kitchen...
Idylliic beachfront private guest suite on the beautiful North Shore of Oahu
Beachfront property just walk onto the beach any time, located on a quiet cul-de-sac. The minimum length of stay is 14 days and I will block a 30 day period as the law regarding this property state that it may not be rented for fewer than 30 consecutive days; however...
Newly Remodeled Modern Condo + Free Parking Waikiki
Welcome to our spacious, modern one bedroom condo located on the 6th floor above the swimming pool/jacuzzi. Renovations on the condo were completed in January 2021. Along with 24 hr. security, amenities include free secured parking (hotels charge up to $50 a day), with...
3-bedroom lovely unit just across the street from beautiful beach.
Discover this fabulous 3-bedroom gem in Ewa Beach, Hawaii. This updated delightful apartment is fully furnished and in a convenient location for island fun. The cozy living room is the perfect for relaxing after a day of exploring. An open floor plan with plenty of...
Lae Nani 534 Fantastic view is what we have, none better on the island of Kauai
COMPLETELY REMODELED AND NEWLY INSTALLED SPLIT SYSTEM AC!! Come and enjoy this beautiful condo with unparalleled view of the Wailua Bay and Pacific. One our most requested condos. Very tastefully decorated and updated (just remodeled spring 2014), this condo offers...
This is the spa for your soul
Queen size bed, one bathroom with exquisite glass block enclosed walking shower with beautiful tile work depicting a swimming dolphin with tile floors and granite countertop.Living room features a queen sleeper sofa with a 52" flat screen TV. Cable is provided as well...
Remodeled 1BD/2BA in Best South Kihei Location, split A/C, 3 min from the beach!
Aloha and welcome to Tranquil Turtle Retreat at Maui Banyan! Our recently remodeled owner-managed condo is located right in the heart of South Kihei close to world-class beaches, shopping and amazing restaurants. We have thought through all the details to make your...
Townhome in Waikoloa Resort - Close to Pool & BBQ Area!
Enjoy resort living at Colony Villas 201, a spacious two-story townhome located at the renowned Waikoloa Beach Resort. This 2-bedroom home is perfect for families or friends, and is close to all the best beaches, restaurants and shopping on the Kohala Coast. The home...
New Listing! Kona Isle Oceanfront|1 BR|Pool,Lanai
Oceanfront Paradise at Kona Isle E32 – Cozy 1BR | Steps from the Sea!Escape to the tranquil beauty of the Big Island and make yourself at home in Kona Isle E32, a top-floor oceanfront condo nestled in one of Kailua-Kona’s most beloved communities. This thoughtfully...
Special ~ Kapalua Golf Villa 24T8 - 1BD Luxury
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! Indulge in the tranquil beauty of Maui at Kapalua Golf Villa 24T8, a beautifully appointed 1-bedroom, 2-bathroom villa that perfectly blends luxury, comfort, and panoramic ocean views. Step...
Puu Poa 211 Air Conditioned and Best View Too
Aloha Unit 211 is on the far right side of the complex and faces almost due west, thus having the best Bali Hai view. You can enjoy Bali Hai sunsets while dining, reclining in the living room, seated in the atrium, lying in the master bed, or of course, while relaxing...
Hoku Hale – Ainamalu at Waikoloa Beach Resort
***Luxury Golf Course Estate with Private Pool, Daily Hilton Waikoloa Pool Access, Concierge Services & Game Room | Sleeps 10+ in Waikoloa Beach Resort***Welcome to Hoku Hale at Ainamalu, your ultimate luxury retreat nestled in the heart of Waikoloa Beach Resort....
Home with mountain views, lanai, & near the ocean
Star of Waikoloa - Ainamalu House with Guest House - October Triathlon SpecialsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You'll be wowed by this newer-built home in the new...
Maui Resort Rentals: Kaanapali Alii 314 – Expansive 2BR+DEN Ground-Floor Residence, Luxuriously Remodeled, Steps to the Beach!
Luxuriously remodeled, this 2 bedroom den ground-floor gem delivers partial ocean views, an expansive 1850 sq ft of interior living area, and a sleeping capacity of up to 8 guests. The oversized outdoor living space and lawn area effectively doubles your lanai...
Views! Views!!!
Looking for that romantic getaway? Our little slice of paradise is ideal for Honeymoons, anniversaries, babymoons, or that special romantic escape. Looking for amazing sunsets and whale watching from you own private lanai? Check us out!!Experience oceanfront tranquility...
Wavecrest Resort Vacation Condo
Come share our little oceanfront slice of paradise on Molokai. When you visit the Wavecrest Resort, the A-building is where you want to be. Right on the water, the experience is totally different. You have a front-row seat for all the beauty of the ocean and all the...
Hali'i Kai 20G "WishWeWereHere" Newly renovated! Oceanfront resort, gears bikes.
PROPERTY DESCRIPTION: Ours is the most spacious floor plan at Hali’i Kai with 1677 square feet, 1930 square feet if include the two lanais. This is a two-story Townhome with the entrance on the second floor, no elevator.You will enjoy our newly remodeled condo with...
Place in Paradise - Kailua Beach Oceanfront Vacation Home
Place in Paradise - Kailua offers casual oceanfront accommodations on one of the most beautiful beaches in Hawaii. Kailua Beach has been voted "Best Beach in the United States" by a variety of publications. Five bedrooms and five and half baths make this an ideal home...
Luxury Mauna Kea Rental Home
The Hawaiian word for family is ohana and we affectionately call our home, O2 or Ohana 2, as it is our family vacation home and we would love to share it with the you!Marvel at the shimmering Pacific Ocean and tropical Kohala Coast views from our inside living space as...
Pristine End Unit, Mauna Lani Golf Villas, Beach Club+Golf Pkg savings!
STVR-21-559570Seeking a flawless, worry-free spot for your next get away? Look no further….Come, relax and make yourself at home in our well-appointed, high-end furnished, corner villa inside the Mauna Lani Beach Resort. Take advantage of our Kings Club membership at...
Hale Okale By Parrish Kauai - Hanalei Value & Location
Located in the quaint and historic beach community of Hanalei Bay, this comfortable Kauai vacation home offers its guests a spacious and relaxing place to settle in and enjoy beach life. Hale O’Kale is walking distance to all of Hanalei town with its shops and...
Maui Resort Rentals: The Whaler 1020 - Luxurious 10th Floor 1BR w/ Gorgeous Ocean and West Maui Mountain Views!
Enjoy beautiful views of the Pacific Ocean and Maui's neighbor island Molokai, as well as views of the West Maui Mountains from this luxurious 10th-floor one-bedroom suite at the iconic Whaler in the heart of Kaanapali Beach.Tastefully remodeled, this suite is the...
Aloha Condos, Na Hale O Keauhou, Townhome E-2, Ocean View, AC
Located in the highly desirable Na Hale Community, this beautiful well-appointed 2-bedroom, 2.5-bathroomtownhome offers spectacular ocean views and breathtaking sunsets. Bothbedrooms feature private, ensuite bathrooms. Additional in-home conveniences includea washer and...
Mauna Kea Villa 3022 - Ultra-Luxe Hawaiian Villa for Rent
This single-level, sophisticated, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living, a chef’s kitchen with Wolf and Sub-Zero appliances, a dining area for 10 with adjoining wet bar as well as bar seating in...
🏖️Walk to Beach, Restaurants, Shopping | Concierge Included | vrKCV
vrKCV - Kolea 15L, Professionally Managed by Kona Coast VacationsWelcome to Kolea 15LA luxurious haven within the renowned Kolea community, located in the heart of Waikoloa Beach Resort on the stunning South Kohala coast. This exclusive residential gem offers direct...
Captivating Ocean Front Condo Living-Poipu Shores
Every evening, the sky transforms into a masterpiece of warm colors, reflecting off the endless ocean, creating an unforgettable view from this coastal retreat. This beautifully designed vacation rental offers breathtaking views of the Pacific, where you can watch sea...
Moana Makai & Moana Mauka – Kailua-Kona Oceanfront Estate
We are 2 luxury oceanfront vacation rentals on the Kona Coast. Voted "Best Private Estate in - Kailua Kona Hawaii" October 1, 2016 These two beautiful homes share the estate’s lava rock saltwater pool and jacuzzi, lushly landscaped yard overlooking the Pacific ocean,...
Privacy + Luxury • Oceanfront • Panoramic View
Summary:Hali’i Kai in Waikoloa Beach Resort • 69-1033 Nawahine Place #13D • 5★ RatedHali’i Kai 13D is a Kohala Coast oceanfront corner villa located in the highly desirable gated property situated in Waikoloa Beach Resort. This upgraded villa boasts 2...
❤️PiH❤️ Shades of Summer ★ Fully detached home ★ Hilton Pool & Waterslide Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Shades of Summer, part of our Hawaiian Luxury Collection. Shades of Summer is a beautiful 3 bedroom / 3 bathroom freestanding home that offers everything that you would ever desire on your Big Island vacation...
Remodeled Quiet Oceanfront Corner Unit on 3rd Floor at Sugar Beach Resort
This unit is remodeled and ready for you to call home for your stay! Walk down the stairs and onto the longest walking beach in Maui! Heading South on the beach, you are a 5 minute walk to delicious Sugar Beach Bakery and Ululani Shave Ice. Head North on the beach for a...
Historic Upcountry Ranch Home
PERMITS: SUP2 2019/0015 and STMP T2019/0002MAUI’S VRBOS ARE NOW OPEN TO TRAVELERS FROM THE MAINLAND AND ELSEWHERE. FOR LATEST INFORMATION PLEASE GO TO travel.hawaii.gov. WE PROVIDE: 1. ENHANCED CLEANING PROCEDURES BETWEEN GUESTS 2. HAND SANITIZER AND DISINFECTING...
Sweet Lava Retreat with Epic Ocean and Volcano Views
** Please note that the House is not a fit for children under 6 years old or the elderly, as there are lots of stairs and balconies, a steep ladder within the Main House, and there is uneven lava in the yard.Welcome to the Hakuma House, a cozy off-grid retreat with...
Beachfront Kihei! A True Beachfront Experience!
Unbelievable main floor beach front condo. Unit 5 of Kamaole One is a 2 bedroom, 2 bathroom, 1100 + sq ft corner unit condo perfect for 4 people. Located in an unforgettable location directly on family favorite Charley Young Beach. The beach features a sand bottom,...
Ohia Lehua Hale-Hot Tub-Fireplace-Fire Table-3-Bed, 2-Bath Newly Renovated Home
Welcome to Ohia Lehua Hale, located just 6 minutes from Hawaii Volcanoes National Park. Escape to our recently renovated vacation home; we recently added many upgrades to enjoy a relaxing stay.*New Built-in Gas Fireplace *New Smart TV*New Outdoor Hot Tub *New Outdoor...
❤️PiH❤️ AQUA MARINE DREAM ★Big Golf Discounts★Free Hilton Passes★Tennis/Pickleball
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Aqua Marine Dream, a part of our Hawaiian Luxury Collection. It's is a wonderful 4 bedroom home and 4.5 Bath (Mahina Model) equipped for up to 10 people.The home has had recently been updated with lovely new...
Poipu Sands 214 - Ground-Floor Condo with Pool & Hot Tub Access, Steps from Stunning Beaches
POIPU SANDS 214 AT KOLOA KAI VACATION RENTALSA Tranquil Island Retreat on Poipu Kai GreenbeltWelcome to Poipu Sands 214, a beautifully appointed ground-floor condo just steps away from the lush Poipu Kai Greenbelt and the breathtaking Shipwreck Beach. Whether you're...
Coastal Remodeled ocean view Papakea Resort condo
Recently updated Papakea Resort 1 bed, 1 bath fully stocked condo is in a great location with beautiful Ocean Views. This bright and airy condo has coastal vibes throughout and can accommodate 4 people. It comes with all the household items and beach gear you'll need...
Whales and great reviews! Royal Kahana 2 Bd/2Ba ! Hotel zoned Safe to Book!
We welcome and need you to visit our beautiful island. We thank you for your support and welcome you! This property is hotel zoned which means that short term rentals will continue to be legal rentals at this property. The apartment zoned properties are proposed to be...