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.
Palm Villas at the Mauna Lani Resort, #F-2: Beautiful Ground Floor unit, AC!
Enjoy the tranquil beauty of this Luxury Palm Villas ground floor, 2 bedroom, 2 bath condo. This special unit has been recently upgraded and includes new Air Conditioning, Kitchen Appliances and Washer/Dryer. The private lanai is complete with a wet bar and gas grill...
OCEANFRONT 3 Bdrm condo with great views of Lanai & Molokai - Noelani 304
Sophisticated Oceanfront LivingThis tastefully appointed condo features two private lanais, offering front-row views of the Pacific Ocean. Enjoy whale watching during the season, mesmerizing sunsets, and the calming sounds of the waves—all from the privacy of your...
Ground Floor Unit on the beautiful island of Maui
Unit 128 building 13 is a clean, and equipped unit. Beautiful ground floor with amenities. Beautiful patio across from pool and steps from the beach. Walking distance from restaurants, bars and a safe crosswalk to the beach. Beach chairs, umbrella and scuba equipment...
North Shore Bungalow with AC - newly renovated ocean view condo
Hale Moi #216A. Welcome to your Garden Island oasis: a stylish island-style retreat in the heart of Princeville. This beautiful, newly renovated studio is your perfect home base for trips to Hanalei town (10 mins) and the incredible beaches on Kauai's North Shore. Enjoy...
Charming 1BR: Waikiki Banyan, Ocean View + Parking!
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...
Kailani Kona- Ocean view, top floor Downtwn w pool
Aloha! Enjoy Kona in our serene 1br top-floor corner unit condo with a sweeping view of the ocean! We are centrally located steps from downtown Kona and across the street from beach access. There's a dedicated parking spot, community pool, in-home laundry, and all the...
Modern AC Home w/ Golf Course & Mountain Views!
Experience the best of Kaua‘i’s North Shore at Hale Lani, a beautifully designed 4-bedroom, 3-bath home in the exclusive Princeville community. With air conditioning throughout, breathtaking views of the Makai Golf Course and Bali Hai mountains, and a quiet cul-de-sac...
1 BEDROOM CONDO IN OCEANFRONT RESORT W/ CENTRAL AC
Relax in Paradise at Casa de Emdeko – Oceanfront Comfort on Alii DriveDiscover the charm of Casa de Emdeko, a well-loved oceanfront property located just minutes from historic Kailua-Kona town. This peaceful resort setting on iconic Alii Drive features convenient...
Wailea Elua 805 - 3-Bedroom Ocean View Luxury Condo in the Heart of Wailea, Maui
Welcome to Wailea Elua 805, a beautifully remodeled 3-bedroom, 2-bathroom vacation rental located in the exclusive, gated beachfront community of Wailea Elua Village on Maui's stunning south shore. Just a two-minute stroll to Ulua Beach, one of Wailea's top snorkeling...
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.
Summary:Fetching Ocean View Condo in the Heart of Kapaa! Plenty to do and see all within walking distance.The Space: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...
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...
Wailea Oceanfront Private Home
State of Hawaii Transient Accommodations Tax License #TA-001-750-7840-01County of Maui Short-Term Rental License #Hotel-ZonedThis home defines the best of Maui with lava step access to a sandy, swimming beach on one side and a lava rock beach on the other side.This...
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 apartment zoned, 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 spacious...
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...
Ko Olina Beach Resort BT-903 3 Bdr 3 Bath Condo!
Aloha and E’ Komo Mai! Hello and welcome to our luxurious vacation rental, at the Ko’olina Beach Rentals unit #B903. We are located in the Beach tower, on Lagoon 2, the least crowded of the four beautiful Ko’Olina Lagoons. This is a beautiful and unique location, where...
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
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 us know what your expectations are for your vacation. Is it a...
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 ★ Free 2026 Hilton Pool Passes
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! Each year we assess and make improvements to our home-away-from-home so our stay and yours are comfortable and enjoyable. Just 10 feet from the ocean and located on the second floor, you will not be...
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...
Coastal Ko' Olina Townhome - Walk to Beaches!
Find lush tropical landscapes, top-class resort amenities, and proximity to tons of historical sites at this 2-bedroom, 2-bathroom townhome. This Ko' Olina vacation rental is within walking distance of the crystal clear waters of multiple coves and beaches. Grab the...
Kona’s Best Golf and Beaches
Beautiful 1,950 SF three bedroom two and half bath townhome, with ONE parking space. Located at the picturesque Fairways of Mauna Lani, a tropical paradise situated on 20 acres. This exclusive gated community is set between the 4th and 12th fairways of the award winning...
Magnificent Ocean View Penthouse, FREE PARKING- 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...
Sun kissed 1-bedroom apartment minutes from Hawi.
This second story ohana is bright and airy with treetop views from every window. You’ll feel like your staying in a cozy treehouse. The bedroom boasts a comfy queen sized bed, ready to lull you into the best sleep of your life. There is plenty of room to stretch out,...
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...
Hale Keleka: 4 BR Hawaiian Plantation-Style Home in Poipu
Breezy, Hawaiian plantation-style getaways are yours at Hale Keleka, a 4-bedroom, 4-bath property in Poipu/Koloa that includes a 3-bedroom main house and a separate 1-bedroom Ohana (guest house). Bring your group of 12 and enjoy a roomy, open-concept floor plan,...
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...
White Sands Village#121: Beachfront Complex, AC, Spacious Unit!
Escape to Paradise at White Sands Village in Kailua Kona! Unit#121 has all the essentials one needs for a Beachfront Vacation. Welcome to your perfect Hawaiian getaway! Nestled in the heart of Kailua Kona, this 2-bedroom, 2-bathroom unit at White Sands Village offers a...
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...
Oceanfront Getaway on Oahu North Shore
Feel your stress melt away in this gorgeous 3-BR, 2-BA oceanfront sanctuary! House is in a gated community on the fabled Oahu Northshore. The secluded, aqua-blue waters of Kawela Bay are in your own backyard—swim, snorkel, surf, paddleboard, kayak and sunbathe...
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...