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.
Poipu Condo! Newly updated - Sleeps 5 - 5 minute walk to the beach!
Aloha! We warmly welcome you to our amazing condo! A 5 minute walk to the best beach on always-sunny south shore of Kauai. It just doesn't get better than this for your vacation get-away!Professional Cleaning and Disinfecting Castle Resorts handles all resort cleaning...
Experience paradise at Maui Sunset: spacious 2BR with stunning ocean views!
Maui Sunset offers the perfect Hawaiian getaway. This spacious two bedroom, two bath offers gorgeous views of the ocean and West Maui mountains.Experience a magical Maui sunset or peaceful morning on your private lanai. Perfectly located overlooking the pool that is...
Luxury Oceanfront 2 Bedroom 2 Bath Penthouse
Completely Remodeled and Renovated, our Corner 2-Bedroom, 2-Bathroom Penthouse is simply gorgeous. The living room and lanai offer beautiful, unobstructed Pacific Ocean and West Maui views. Through the long wall of windows stretching from the kitchen to the living room...
Kauai Kailani 204. Ocean View Condo in the Heart of Kapaa! Walking Distance to many Establishments.
This condo has it all. Elevated view of the ocean with the sun rising over the water. The large covered lanai is perfect for outdoor dining/living. The second bedroom contains a Queen size bed. Stacked washer and dryer. Only steps to the ocean and walking distance to...
QUIET COMFORT! SALE!!! 199/nite APRIL, MAY, JUNE 2025!!!nPL-STVR-2024-000967
New paint, new bathrooms, new floors throughout. Exceptional townhouse condominium in the Colony Villas at Waikoloa Beach Resort, a gated community on the perimeter of the Kings golf course in the sunny crescent of the Big Island with sunshine 350 days a year. Two pools...
Oceanfront Honokeana Cove! Beautiful condo #215
BEAUTIFUL REMODEL TO THIS VACATION RENTALBeautifully remodeled(11/22) for welcoming ambience, this newly updated second floor unit is light and bright, featuring bamboo and teak cabinets, LVP flooring, and updated furnishings for your home away from home. Lovely views...
Ocean Front with a beach and Swimming pool fantastic Views at Nohonani on Maui
Stunning sunsets from your lanai, whale-watching in season, ea white sandy beach right in front, swimming pool, fantastic view from the lanai and master bedroom,. Just some of the features of our wonderful home. Old Lahaina town, Restaurants and grocery stores just a...
Hawaii Life Rentals Presents Hale Honu
Welcome to your private oasis on the east side of the Big Island. The first thing you will notice are the breathtaking ocean views, picturesque palms, and refreshing sea breeze - Hawaii’s natural air conditioner! A covered lanai offers the ideal location to experience...
Kukuiula Cottage #36 By Parrish Kauai - spacious plantation style home w/ AC, po
This luxury Kauai vacation rental is located in the newest resort community of Kukuiula. This fabulous new home has lovely garden views from the main living and pool deck area and the upstairs guest suite with den and private lanai has a lovely distant ocean...
Waikoloa Colony Villas#903 2 Bedroom 2.5 Baths with AC!
Welcome to your tropical retreat at Waikoloa Colony Villas! This spacious 2-bedroom, 2.5-bathroom offers the perfect blend of comfort and luxury in the heart of the stunning Waikoloa Beach Resort area. WELCOME! The villa features an open-concept living area with high...
Modern, Updated, & Clean Oceanfront Get-A-Way at Napili Point.
This property is not on the Minatoya List, so unexpected cancellations due to the county potentially cancelling short term rental permits is not an issue with this property. Nestled on Kaelekii Point overlooking Honokeana Bay on West Maui, this clean, modern, and...
Oceanfront Kihei Sands Beachfront Condos B3 – 2 bd 2ba
Our property is NOT impacted by the news of potentially prohibiting Short Term Rentals (STR) in Maui. Kihei Sands is zoned as a hotel property so meaning it is exempt from any of the potential STR regulations being proposed by the County.Located in North Kihei just...
Lae Nani #222 - Wailua Beachfront with pool, tennis and amazing ocean views!
This two bedroom condo is on the 2nd floor of a 3 story building. The two bedrooms have a king bed and a queen bed and each have an attached bathroom. The kitchen has been recently remodeled and has all the tools you need to make a good meal. The wifi service is...
Deluxe Penthouse Oceanfront Studio with Breathtaking Views and Central A/C.
This direct ocean front deluxe penthouse studio is the perfect place to spend a relaxing vacation right on the ocean's edge!! Literally 20 feet from the ocean, you cannot beat the view anywhere from the lanai!! Perfect for lounging, dining, reading or just relaxing. You...
Ocean Front ground floor cozy condo with brand new bedroom remodel!
This cozy little Condo is perfectly situated just 60 feet from the edge of the ocean with panoramic views of both Lanai and Molokai! You can watch whales and sea turtles while sipping your morning coffee right from the table on the lanai, or you can explore the area,...
Island Beach House 1 minute walk to Sand ~ Kids Welcome Lic#TVNC1058
Ask us about a DISCOUNT for any Nov. dates still open in 2025. This is a legal permitted vacation rental. Permit #TVNC-1058Please see our rental agreement or ask us for ACTUAL CANCELLATION POLICY and REFUNDS. We DO give refunds and have a cancellation policy. Please let...
Wailea 1 BR Condo, amazing lanai, close to everything, good pricing
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully this provides some clarity if you have been following this process and were concerned about booking in the next couple of...
❤️PiH❤️ Kamilo Luana ★ Relax, rejuvenate & unwind
Brought to you by Paradise in Hawaii Luxury HomesKaMilo Luana is a stunning and spacious 4-bedroom, 3.5-bathroom home in the highly desirable KaMilo community at Mauna Lani.Thoughtfully designed with both comfort and style in mind, this home truly lives up to its...
Baby Beach Bungalow I - Beautiful Bungalow Steps from Beach
Discover Baby Beach Bungalow I – Your Perfect Kauai RetreatNestled in the highly sought-after Baby Beach neighborhood along Ho'ona Road, Baby Beach Bungalow I offers the perfect blend of comfort and convenience. This charming, single-level cottage features a spacious...
OCEANFRONT CONDO MAUI SUNSET#215-A, SLEEPS 4
MAUI SUNSET IS A FABULOUS OCEAN FRONT PROPERTY. Has a community swimming pool, heated during winter months, hot tub, gym, tennis courts, putting green, barbecue grills.Just STEPS TO THE BEACH allows for WINDSURF, WHALE WATCHING in season, and be on the look out for...
Direct Oceanfront - Intimate, Contemporary Studio Condo
ALOHA and thank you for considering our home for your Maui vacation! Our condo was completely renovated in Dec. 2011 and we hope you like what we've done.Just 10 feet from the ocean and located on the second floor, you will not be disappointed! Upon entering the condo,...
Newly Renovated 1BR w/ King Bed & Great Ocean View
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...
BHTS Kauai Vacation Condo - No Housekeeping Fee
Nestled on a hillside overlooking Kalapaki Bay. Make yourself at home in our 2-bedroom apartment that has a full kitchen, dishwasher, washer & dryer. Banyan Harbor is only 2-miles from the Lihue Airport and centrally located on the Island of Kauai which makes it...
Kona’s Best Golf and Beaches
Step through the doors of our beautiful 1,950 SF three bedroom two and half bath townhome and let your Hawaiian experience begin. Located at the picturesque Fairways of Mauna Lani, a tropical paradise situated on 20 acres. This exclusive gated community is set between...
Magnificent Ocean View Penthouse, FREE PARKING-n Pool renovation until 2026
Enjoy being on top of the world and just one block from Waikiki's best beach. Our one bedroom beach house has breath taking panoramic ocean views from front and side windows, a separate fully equipped kitchen, 50" flat screen Smart T.V., large lanai facing the ocean,...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Condo, Recently Updated, Sunsets! HKH-412
** 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...
2 Bedroom Paradise Getaway on Molokai
Spacious and wonderfully positioned corner unit condo on the third floor that offers privacy, no noise from above and only one wall connecting this unit with others. The main living area and bedroom face the ocean for spectacular views. There are no elevators on Molokai...
The Best of the Best JUST GOT BETTER with 3rd Remodel
Papakea dies not charge So now you save more monet staying at Papakea! Book with no fear the government will cancel your booking and you lose your payment as described below:We are very sorry that the Maui Government is trying to use fear tactics to get the short term...
Amazing Ocean View 2BR 2Bath with Modern AC. Beautifully Upgraded. KKSR 9-305
Aloha! Welcome to Keauhou Kona Surf & Racquet Club #9-305This spectacular top floor, beautifully decorated, highly desirable corner unit has an impressive 1,188 interior square feet, plus a covered wrap around lanai with ocean views. Unit features two bedrooms & two...
HOME & GUEST HOUSE FOR PRICE OF 1 POIPU BEACH ESTATES 5 BR/ 5 BA WALK TO BEACH
ALOHA & WE WELCOME YOU TO OUR COMFORTABLE HOME AWAY FROM HOME! LOCATED IN THE SUNNY SOUTH SIDE OF THE GARDEN ISLAND OF KAUAI IN POIPU BEACH, THESE 2 HOMES HAVE BEEN RECENTLY CONSTRUCTED WITH TOP OF THE LINE FEATURES, PERFECT FOR A PARADISE FAMILY GATHERING OF MULTIPLE...
Luxury Kolea Villa in Waikoloa Beach Resort-Oceanfront Development
If you are looking for five star accommodations with incredible views, Or you want to own part of paradise this is the spot! Brand new Villa, newly furnished in an upscale gated oceanfront community located across from a private beach club and direct access to Waikoloa...
Last minute discount, 4/26 - 5/12. Huge 3/3 Oceanfront Penthouse
This beautiful Ocean Tower 10th floor Penthouse end-unit is huge, recently renovated, and has a unique floor plan with glass doors on both sides of the main living area that slide completely into the walls, creating a wide open space more than 75 ft wide with east,...
Seaside Zen Cottage - A beach is your front yard
This is an ideal place to relax with family and friends. The lagoon in front of the cottage is a great place for snorkeling, for teaching small children to swim and to rest in the healing waters.Rental of the Cottage can be combined with rental of the "Robertson's Beach...
Oceanfront Paradise! Breathtaking Pacific Views Await at Sugar Beach #319
SUGAR BEACH RESORT, #319Welcome to Sugar Beach Resort #319, a beautiful one-bedroom oceanfront condo in North Kihei. With direct beachfront views, modern comforts, and central AC, this unit is the perfect retreat for couples or small families seeking a true Maui...
DISCOUNTED RATES! 311 Beautiful oceanfront 2 bed 2 bath 3rd floor condo
Located on the 3rd floor of a small (only 42 units) quiet complex, you will have unlimited views of the beautiful sunsets, turtles feeding and playing in the reefs, right in front of the complex, and whales at play, during their season, on your private lanai. We have...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...
Maui Resort Rentals: Honua Kai Hokulani 448 - Spacious 2BR w/ Partial Ocean & Mountain Views!
Hokulani 448 is a luxurious two-bedroom suite offering gorgeous views of both the blue Pacific Ocean and the lush West Maui Mountains. Suite 448 affords a perfect opportunity to gather, reconnect, and celebrate. The suite can accommodate up to six guests in two...
Gorgeous Oceanview at Kaleialoha 214 Special 175 nightly for Nov- Dec
Amazing ocean views in an oceanfront condo at Kaleialoha. Nicely furnished and updated with a/c in living room and bedroom unlike other units in this complex, fully appointed kitchen and bathroom. Washer/dryer inside the unit for your convenience. Very quiet and private...
❤️PiH❤️ Island Melody Villa ♥ Stunning Views ★ Free Hilton Resort Passes ★ Bikes
Brought to you by Paradise in Hawaii Luxury HomesIsland Melody Villa at The Islands is a spacious 2,600-square-foot home that effortlessly blends luxury, comfort, and thoughtful design.Featuring three beautifully appointed bedrooms, this villa comfortably accommodates...
Imperial Hotel at the Waikiki Beach Walk Penthouse
PLEASE READ THIS IN IT'S ENTIRETY......Hawaii Tax ID #TA-137-632-1536-01 & GE-137-632-1536-01 TMK/Parcel# 260020140286 Address: 205 Lewers St Unit C/12B, Honolulu, HI 96815Located atop the newly remodeled Imperial Hotel at the Waikiki Beach Walk! New salt water rooftop...
Palekaiko Estate - Kailua Kona Luxury Home with Ocean View
Palekaiko, meaning paradise, is our 3200+ sq. ft. home away from home situated on over an acre in a gated community. Palekaiko has three bedrooms, three and a half bathrooms, an office and almost 1000 sq. ft. of outdoor living space. On the property, you will enjoy over...
Lehua Lounge in the Heart of Downtown Kona
This place truly is hard to beat! Just 10 minutes walk to all Kona town, the beach & pier. In a peaceful neighborhood where you don’t hear any traffic noise at all. Newly installed AC (October 2025) keeping you cool & comfortable throughout the entire home. AC in both...
Oceanfront condo with pool, water view, & high-speed WiFi
Mahina Surf 114Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a lovely view of the ocean on your own privately furnished deck, as well as a view of the shared pool! This home...
Best of Mauna Lani! Clean, Spacious Resort Townhome, Pool/Beach Club!
This wonderful townhouse will help you make your Hawaiian vacation dreams come true! Beautifully decorated and well appointed you will find all of the comforts of home in this amazing tropical setting. The luxurious master suite will not disappoint with a king bed,...
"Drift Away" Studio Oceanview at Islander on the Beach 259
Drift Away – Oceanview Studio at Islander on the Beach 259Welcome to Drift Away, a second-floor oceanview studio at Islander on the Beach where you'll be transported to the peaceful beauty of Old Hawaii. Wake to the sound of the waves, breathe in the fresh ocean air,...
At Awapuhi Views, you can check out the surf conditions, and enjoy the breezes
Our home is located halfway down the Miloli'i Rd. We have a very large master bedroom with a King bed, the Master has bow- windows and its own door to the wrap around deck.oceanside deck. The Master bedroom has a walk-in closet, and en suite bath with tub and shower and...
Luxury condo in prestigious Hali'i Kai oceanfront community. Ocean bar and grill
Condo, 2 bedrooms, 2 baths, ( Sleeps 6 )Hali' i Kai is a 30 acre gated oceanfront complex on the Big Island of Hawaii with numerous luxurious resort like amenities. It is about a 20 minute drive from Kailua-Kona airport. Our condo, #23D is a spacious second floor end...
Tropical hideaway with pools, hot tub & grill - the waves await
Maui Kamaole H206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.n
Aloha. Have you noticed how we're constantly towards the top of Kihei and Maui Vista searches. Well, vrbo has a system of metrics they use that ranks all listings, basically putting the best units available in front of guests...and we're crushing those metrics and have...
Modern, Oceanfront with A/C, discounted for 2025, plus monthly discounts!
Welcome to your Hawaiian Haven on Maui!Please scroll down & read the full description & FAQ's as we have likely already answered your questions below! You can also find out more (and get exclusive discounts) by searching for Hawaiian Haven and the Elikapeka Suite...