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.
Oceanfront Maui Sunset Condos ground floor in Kihei
Great location on ground floor renovated condo B104 at the Maui Sunset. Picture yourself on the ocean front in sunny south Maui. Kihei is well known for its laid-back atmosphere, world famous beaches, affordable highly rated restaurants, and central location.Large...
A Little Piece of Maui Paradise for You to Enjoy!
Aloha and welcome to our piece of Paradise in Kihei Garden Estates (KGE). Come and enjoy our beautifully upgraded, two-bedroom, two bath, first floor, garden view condominium. We are perfectly located in the heart of Kihei – just a few minute walk from the best...
Ilikai 1001 Mountain & Waikiki City Views - King Bed, Sofa Bed
BEAUTIFUL WAIKIKI CITY/MOUNTAIN VIEWS! STEPS TO WAIKIKI BEACH. Memorable Meals from the Lanai. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.The iconic Ilikai Suites are located at the gateway to Waikiki.Newly...
Walk to the Beach! Newly renovated. Many upgrades!
This newly upgraded condo for 6 offers a wonderful affordable vacation opportunity for the whole family. This end unit is located on the quiet side of the building with much privacy and upcountry views. There is a fully equipped kitchen with quartz counter tops, and all...
PREMIUM Remodeled 1 BD/2BA Oceanview Tropical Dream Come True
This Premium 1-Bedroom, 2-Bath ocean view condo located in Tower 1 on the 4th floor, is beautifully remodeled throughout. Enjoy a gourmet kitchen that is fully appointed with elegant granite counters and top rated appliances. A comfortable and spacious living room with...
Huge Ocean Views! Direct Ocean Front Condo Sugar Beach Resort #527
Fantastic ocean front view, this beach front condo features new flooring, a very comfortable California king-size bed, queen size sofa bed, central AC, and an entertainment center with digital HD flat-screen TV & surround sound, and free WiFi. The full kitchen has all...
Hali'i Kai Most Oceanfront Location! Walk to Pool, Gym and Restaurant
Enjoy oceanfront living at Hali'i Kai 14H, a 3-bedroom vacation condo that boasts the best oceanfront location at Hali'i Kai. Smell the sea breeze from your private ground floor balcony in a setting famous for watching the whales make their migration every winter. The...
Sugar Beach Resort Condo w/ Free WiFi, A/C-Beaches Await
Sugar Beach Resort 204Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Kona Reef A-24 - True Oceanfront Condo
Honu HavenKona Reef Unit A24 is a beautifully appointed one-bedroom, one-bathroom oceanfront condo nestled in the heart of Historic Kailua Village. Step into the unit and let the soothing sound of the ocean wash away all your worries and the hustle and bustle of the...
Steps to the Beach Guesthouse
A private setting in a detached home on a wonderful street! The longer the reservation the better, please contact for details. To answer the most common question, yes, we are 'steps' away: 80 medium sized steps for me! The beach is down a sandy path and is a one of the...
Beautiful Ground floor! Easy Ocean and Beach Access! Best Location! #102
ALOHA AND WELCOME TO HALE KAI # 102Beautiful one bedroom condo with king bed and sleeper sofa that can accommodate up to four people. Children and long term rentals are welcome. Located in Honokawai, which is between Kaanapali and Kapalua in West Maui. The condo is...
Ocean view home office
Right by the Four Seasons at Ko Olina, the house is beautifully located inside the luxuriously built Kai Lani with an ocean view from the balcony and the master bedroom. Only minutes away from the beach at the Ko Olina lagoons, you will also have direct access to the Ko...
~Kamaole Sands~Owner Pd Resort Fees~UPDATED!~
Embark on a Maui retreat like no other with our newly renovated beach vacation rental, strategically located across the road from the sun-drenched shores of Kamaole Beach III.The beach, with its pristine sand and crystal clear waves, becomes an extension of your living...
Keauhou Kona Surf and Racquet Club, Townhouse #5
Vacation in this spacious, absolutely oceanfront 2 bedroom, two story townhouse! It’s located on Hawaii's BigIsland, 5 miles from the town of Kailua-Kona at the Keauhou Kona Surf & Racquet Club. This gated 17 acre oceanfront complex has beautiful tropical landscaping,...
Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Ocean Views, and Orchard
The moment you enter the Royal Palm lined driveway of this gorgeous estate, you'll know you have arrived at your new sanctuary! Papa Belle Estate is a 3.5 acre oasis on the South Kona coast offering breathtaking views, wonderful amenities, and lush surroundings.Soak in...
Heart of Waikiki! Close to Beach! Free Parking Nearby.
Regency on Beachwalk #64 – 255 Beach WalkYou'll really appreciate the convenient location of this fully-furnished 6th-floor end unit condo (494sf plus 145sf lanai with table and chairs, for a total of 639 sf) at Regency on Beachwalk, right in the heart of Waikiki and...
Mana Kai Maui Resort condo with pool & WiFi - snorkel, surf, swim
Mana Kai Maui Resort 202COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Swim, lounge, and snorkel at the fabulous Mana Kai Maui Resort, the jewel at the end of one of Maui’s best...
Magnificent mountains of Kauai's north shore provide a spectacular backdrop.
Many large windows in this roomy, newly built townhouse offer wonderful views of the championship Prince Golf Course's verdant greens and fairways. The magnificent mountains of Kauai's north shore provide a spectacular backdrop for this scenic vista. Relax on the lanai...
Modern Beautiful Renovated Maui Vista 3220
Discover the newly renovated charm of Maui Vista 3-220, where a fresh tropical ambiance awaits your Maui escape. Immerse yourself in the clean, inviting theme that sets the stage for an unforgettable adventure. Just steps away from the renowned Kamaole I and Charlie...
Haleakala Shores A-302 - Stunning Ocean Views, Beautiful Renovation, Wi-Fi, & AC
Indulge in the ultimate Maui escape at Haleakala Shores A-302, a meticulously appointed two-bedroom, two-bath ocean-view condo nestled within the coveted A Building of the Haleakala Shores complex. Immerse yourself in luxury and comfort with a newly remodeled, fully...
Kona Coast Hideaway w/ Patio & Pacific Ocean Views
The clear Pacific waters, volcanic rock beaches, and vibrant hibiscus flowers of the Big Island await at this 3-bedroom, 2-bath vacation rental bungalow overlooking the sea. This house is the perfect launching point for all your Hawaiian adventures! Snorkel at places...
Hale Kona Kai 312 - Absolute Oceanfront Condo with wraparound lanai
Hale Kona Kai unit 312 is one of our most popular units at Hale Kona Kai. This 3rd floor corner unit features a wraparound lanai facing west and south for full, unobstructed ocean views and the best possible breeze! The unit has been beautifully updated and has...
❤️PiH❤️ BLUE SERENITY ~ Sleeps 14 ~ Private Pool & Spa ★ Detached Ohana Suite ★ eBikes ★ water slide
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Blue Serenity, a brand new exquisite 4 bedroom, 4 1/2 bath home located in Hapuna Estates within the Mauna Kea Resort. Prepare to embark on a truly remarkable escape where luxury, comfort, and natural beauty...
312 - Fantastic remodeled oceanfront with great ocean view and A/C!
* FREE HI SPEED INTERNET CONNECTION * FREE LONG DISTANCE CALLING TO USA AND CANADA * Ocean front condo has been nicely upgraded and newly installed A/C!* 100 feet from one of the finest beaches in Maui * Wonderful snorkeling and water sports at your doorstep - watch the...
The Onion House "Architecture so full of life it seems to breathe"
PLEASE READ COMPLETELY PRIOR TO BOOKING REQUEST:Created for the McCormick Spice family, the Onion House is a unique architectural treasure with stunning visual aesthetics. It has been featured on MTV, Travel Channel, Learning Channel, Fine Living Channel, HGTV, Global...
Private Handcrafted Cottage, Walk to Secluded Beach, Hot Tub, Tandem Kayak, WiFi
"Twin Hearts", a Kauai North Shore vacation rental homestay cottage, is a wonderful private one bedroom, one bath handcrafted rental accommodation located at the ocean end of our 7.6 acre Kauai North Shore estate and farm parcel. The handcrafted cottage features tons of...
Private Island Retreat. Tropical Sanctuary.
UALANI RETREAT Fully Licensed & Permitted. Locally Owned & Operated B&B BBPH 2012/0002 SUP2 2012/0001Terrific Discounts Thru October. Private detached 1 bedroom cottage on 3 acre tropical retreat. Lush haven surrounded by fruit trees and bamboo groves. Nicely equipped....
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Welcome to your Maui escape — an exquisitely remodeled 1-bedroom, 1-bathroom villa in the exclusive gated oceanfront community of Kapalua Bay Villas. Perched between Oneloa Bay and Kapalua Bay Beach, this luxury retreat offers the perfect blend of elegance, comfort,...
Hale Kahili: 8BR Ocean View Estate w/Pools+Spa!
This spacious, sparkling compound offers ideal large-group accommodations in an idyllic setting. Two elegant new villas nestle on an expansive 1-acre lot, with views that might have been plucked from a rack of curated postcards: glittering swatches of ocean, craggy...
Cozy Oceanfront Home - Secluded Beach, North of Sunset Beach - Near Kawela Bay
Hawaii Tax I.D for both TAT & GET. No. 027-702-8864-01Our oceanfront home, Kawela Kai, is located on the North Shore of Oahu in between Sunset Beach and the Turtle Bay Resort. The stretch of beach where we are located is beautifully secluded and uncrowded. The beach is...
Sunseekers Walk To Kamaole Beach I, One Of Maui's Best For Swimming And Sunsets
Ground floor, super clean unit in one of maui's favorite south kihei complexes. Across the street from the great kamaole beach park. Three tennis court, three pools and lots of barbecues for fun and entertaining. Big lanai for dining and extra room rolling out to the...
Beautiful 1 bedroom condo. Private ocean-view lanai overlooking fairway!
Welcome to paradise! At a time when there was much uncertainty in the world, we made a big decision to purchase in May 2021, as our lifelong dream is to snowbird in Maui. Until that time comes, we would love to share our home with others. MAUI IS OPEN AND WELCOMING —...
Welcome to Hokulani 345, Great Ocean View! Third Floor 2 Bed 2 Bath condo
Aloha and welcome to Maui!Our unit is in the Hokulani Tower, Unit #345Beautiful Ocean View Condo**We have a collection of beautiful Honua Kai condos in both towers. We have several one bedroom, 2 bedroom and 3 bedroom condos.The Honua Kai (HK) resort is located at the...
Hale Lokelani O-403 elegance and beauty to relax
The Beach Villas at Ko Olina is the ultimate getaway, perfectly situated oceanfront on the second lagoon in the exclusive Ko Olina Resort. This luxurious property combines tranquility and convenience, located next door to Disney’s Aulani yet far enough from the crowds...
Menehune House, quick walk to tide pool beach
Maui County Vacation Rental Permit: STPH2013/0010 GE-066-317-9264-02/TA-066-317-9264-01TMK-260120340000The Menehune property is located in Kuau Point, a residential sea-side outcropping near Paia, on Maui's well-loved North Shore. It is a quick walk to the Kuau Channel...
Hale Anu Keanu: Serene Garden Getaway w/ AC & Hot Tub
Hale Anu Keanu is a recently remodeled, plantation-style retreat on Kauai’s north shore, nestled in Princeville’s peaceful and upscale neighborhood. With 2,400 square feet of elegant island living, four inviting lanais, and a private backyard hot spring spa, this...
Wailea Ekahi 4E, Bordering Private Tropical Greenbelt, Split AC and Beautiful!
Welcome to Wailea Ekahi 4E, a serene one-bedroom, one-bathroom retreat nestled in the heart of Maui's lush Wailea coast. Perched on the second floor of a low-rise building, this corner unit offers a private and peaceful setting, surrounded by tropical greenery and just...
BRAND NEW REMODEL-QUIET END UNIT LOCATION-AC-2 PRIVATE BEDROOMS-OCEAN VIEWS
Book with confidence, this stunning newly remodeled, 2 bedroom, 2 bathroom spacious condo. Located in a great location within Kamaole Sands, this condo has a rare floor plan with 2 private bedrooms, ocean views, and is a short walk to Kamaole Beach 3. It is managed by...
LOVELY*Piece of Paradise in Beautiful South Maui!
This South Maui studio boasts pure privacy from your quaint outdoor seating area. The exclusive studio can comfortably accommodate up to 4 guests. The luxe complex has so much to offer. Located just steps from some of Maui's top beaches, restaurants, and shops.Enjoy a...
KBM Resorts | FREE CAR | Honua Kai Konea | Ground Floor, 2-Bedroom Condo with Easy Pool Access! HKK-140
** 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...
Kuilima Estates West 3 Bedroom
TMK (1)570010290042 Welcome to Kuilima Estates West. Location! Location! Location!Only steps to the grounds of the famous and newly renovated Turtle Bay Hotel on the North Shore. We are a Legal Vacation Rental.The condos are Surrounded by Two Beautifully manicured golf...
Beautiful 3 Bedroom AC Beach Home, Close to the Best Snorkeling Beaches in Hilo
WHY STAY ANYWHERE ELSE IN HILO BUT CLOSE TO BEACHES AND OCEAN WHERE THE WEATHER IS BEST!!!WE'RE EXCITED TO NOW PROVIDE GUESTS WITH THE COMFORT OF A NEWLY INSTALLED SPLIT AC SYSTEM!!Our islands have been experiencing the warmest and most humid weather we have had in...
Modern Ocean Breeze Oasis, Beautiful Maui Condo
Welcome to my cozy condo located on the 2nd floor at Napili Shore on West Maui. This studio apartment is just a 2-minute walk from the beautiful world-class beaches where you can relax, swim, and snorkel. This prime location offers the perfect retreat for those seeking...
NEW! Waikoloa Hills 2 Bedroom, 2 Bathroom Condo, Pool and Golf!
Get the best central location for your Big Island vacation! Our condo at Waikoloa Hills is a bright and comfortable two story unit with two bedrooms and two full bathrooms. Both bedrooms are upstairs and each has a queen sized bed and lovely garden views. The master...
Includes Hilton Pool Pass for 2025 and Waikoloa Gold Member Golf Discounts. Waik
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 302Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted...
Tower 1 South facing. Beautiful Ocean, Lanai , koi pond and courtyard views
This breathtaking studio has amazing views. From the lanai looking towards the right you can see the white sand of Kaanapali Beach, lapping waves, catamarans, ocean and the Island of Lanai. Looking towards the left you will see the beautiful west maui mountains, golf...
KAUAI KONG QUARTERS OCEANVIEW 2 Bdrm 2 KINGS 1 TWIN. NextDoor2Hyatt Dining&Bars.
See over ONE HUNDRED Five Star Reviews for this condo. A/C is in the bedrooms and NEW furnishings Installed. New Luxury Beauty Rest mattresses. Coastline OCEAN VIEW of Shipwreck BEACH and the Mountain Range as seen in Jurassic Park. Walk to Poipu Beach and Shipwreck...
GORGEOUS REMODEL-GROUND FLOOR CONVENIENCE-WELL EQUIPPED-AC-PRIVATE LOCATION
Book with confidence, this gorgeous remodeled 1 bedroom, 1 bathroom, ground floor condo at Kamaole Sands. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available...
Luxurious & Spacious Ground Floor Gem with Panoramic Oceanview - Wailea Elua 305
Wailea Elua #305 – Stunning Ocean View Retreat with Luxury Comforts and Designer FinishesExperience the elegance and serenity of Wailea Elua #305, a spacious 2-bedroom, 2-bathroom condo beautifully redecorated with high-end furnishings and panoramic ocean views. This...
Upscale Mauna Lani, 4BDRM, 2MSTR BTHS, 5 Beds for 8, Spacious W/Bikes Near Beach
Spacious and well-maintained home in Kamilo at Mauna Lani, 10% off for 1 week's stay. Many amenities - including card key to access private beach club at Mauna Lani, bicycles and a wonderful rec cen. Walk or bike to 5 gorgeous beaches.***Please note this home is managed...