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.
Trade Winds Blow..Surrounded by Glass!
This magnificent 2 bedroom/2 bath luxury home is waiting for you with its spacious, upscale furnishings, located steps from the ocean. Walls of glass highlight the panoramic ocean view with Haleakala as a backdrop. The sound of the ocean serenades as you read your book...
Waterfront condo with pool & hot tub, loft & lanai with ocean views
Sunrise Hale at the CliffsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy captivating ocean, mountain, and waterfall views from this top-floor Cliffs Resort condo. Tall vaulted...
360 Ocean Views + Full Remodel! Top Floor # 904!
When you think of Hawaii you imagine awe-inspiring views, amazing sunsets and the natural beauty of the wild blue Pacific. These sights are a daily pleasure from the comfort of your own private lanai. This beautiful ocean view home is one of a kind!!Watch the sunset...
Maui Resort Rentals: Kaanapali Alii 113 – Expansive 3BR Ground-floor Residence, Luxuriously Remodeled, Steps to the Beach!
Gorgeously remodeled, this 3-bedroom gem provides an expansive 1850 sq ft of interior living area and boasts an abundant sleeping capacity of up to 9 guests. Step outside and enjoy the largest outdoor lanai on offer at the entire resort. Since this residence is located...
Luxury Beachfront Home w/ Pool, Spa, AC & Stunning Sunset Views at Mermaid Cove
Mermaid Cove is an expansive three-level oceanfront estate in Kailua-Kona, crafted for family gatherings and multigenerational retreats. With 4,000 square feet of living space, four bedrooms, a kids' room, and thoughtful extras, this beachfront haven welcomes up to 14...
Cozy Hawaiian Studio, Budget Price, Steps 2 Beach, Free Wifi
This quiet studio condo in North Kihei sleeps 2 people on a queen murphy bed and queen sleeper sofa. The well kept complex offers a nice pool, jacuzzi, tennis court, BBQ area and on site laundry. The full kitchen offers the budget traveler the option of cooking although...
BEACHFRONT LEGAL PRINCESS CONDO-FREE PKG/WIFI-POOL, HOT TUB,TENNIS/PICKLE BALL 2
LEGAL VACATION RENTAL! AWESOME 180º UNOBSTRUCTED BEACH, OCEAN & SUNSET VIEWS! FREE PARKING IN GATED LOT and FREE INTERNET/HI-SPEED WiFi. NO RESORT FEE. POOL-HOT TUB-TENNIS-PICKLE BALL-PING PONG-BBQ**NO CENTRAL AC--HAS PORTABLE AC IN BEDROOM, BUT IT WILL NOT COOL OTHER...
Ilikai 2122 Deluxe Ocean, Lagoon Views Kg Bed, Sofa Bed, Parking Included
STUNNING OCEAN & Lagoon VIEWS! STEPS TO WAIKIKI BEACH. SPECIAL - Includes Parking Stall. Memorable Meals & Views from the Lanai. , shops, buses, rental cars, parks & Waikiki night life.Beautiful remodel. Fully equipped and very clean. Parking spot included. AC, cable,...
Diamond Head Views! Freshly renovated! A/C, Parking and Wi-Fi Included!
Waikiki Banyan #2603-T1 – 201 Ohua Ave.Fresh and modern, you'll love the feel of this contemporary one-bedroom air-conditioned suite (533 sq.ft. plus lanai with table and chairs) at the repeat-guest favorite Waikiki Banyan! Gorgeous Diamond Head, Kapi?olani Park, and...
Sugar Beach Resort Condo w/ Shared Pool/Hot tub, Private W/D-Surf, Bike, More
Sugar Beach Resort 405Our 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...
KBM Resorts | FREE CAR | Wailea Elua Village | Ocean view | Spacious 2-Bedroom Condo! WEV-2103
Oceanview 2-bedroom, 2-bath villa in Wailea Elua with gourmet kitchen, large lanai, luxe resort amenities, and beach access. Includes complimentary rental car for 6+ night stays through 2025.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with...
Oceanfront 2BR Condo w/ Stunning Views & Lanai
This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances.Oceanfront Luxury with Panoramic Views, Modern Upgrades, and Beach Access in LahainaAloha and E Komo Mai (Welcome) to Your Hawaiian Oasis! Step into a world where the...
Private Oceanview Oasis w/Pool, Spacious Lanai, & Stunning Sunsets: Ono Oasis
True to its name, Ono Oasis offers a unique tropical retreat for a dream Big Island vacation, with distant ocean and sunset views, a solar heated saltwater pool, and over 2,800 square feet of luxury living space. This extraordinary home provides the perfect setting for...
Luxury Living at the Allure in Waikiki (30 Nights Minimum Stay)
This beautiful 2 bedroom condominium at Allure Waikiki #2709, offers state of the art kitchen appliances, great for people that love to cook. It also has a washer and dryer in the unit. The Allure is located in a prominent Waikiki location, within easy reach to many...
Newly Remodeled 1br/2bath F101 Maui Eldorado
ALOHA!! Welcome to this beautifully remodeled spacious modern 1 bedroom condo 2 full bathrooms at the Maui Eldorado Kaanapali F101!! Perfect for a couple or family get away with all the comforts of home. Enjoy a leisure stroll or a quick ride in a golf cart to one of...
Charming Coconut Coast Condo Centrally Located
Were back after a 4 year hiatus. We haven't shared our Home Away from Home since the pandemic, but we've decided that it's time to once again share our little getaway with those wanting to see what the beauty of Kauai has to offer.First Floor Unit - 1 bedroom, 1 bath...
🏖️AC | Resort Amenities | Comfortable & Spacious | vrKCV
vrKCV - Keauhou Gardens 3202. Professionally managed by Kona Coast VacationsWelcome to Your Spacious Kona Retreat at Keauhou GardensExperience the perfect blend of comfort, convenience, and island charm in this beautifully remodeled, air-conditioned 1-bedroom,...
Hanalei Bay Villas #12, Waterfall and Ocean Views, walk to beach and One Hotel
This lovely Hanalei Bay vacation rental home, is a classic Hawaiian style pole house - suspended on poles and giving the house fabulous circulation from the cooling ocean breezes. The location and the views are unbeatable for a relaxing beach vacation. From nearly every...
Luxurious Getaway
Private oceanfront lounge for relaxing under the Hawaiian sun. Smell the salt water, listen to the ocean and allow yourself to be caressed by the warm trade winds. Ocean access to surf, swim, snorkel and sun bath along the Gold Coast. Luxury at affordable price: Simple...
Tropical Poolside Condo on Napili Bay Beach with AC, #E141
Escape to Paradise: Your Ideal Maui Getaway Awaits!Tranquil Garden-View Condo: Step into our charming ground-floor condo at the prestigious Napili Shores Resort in Maui. This inviting one-bedroom, one-bathroom haven features a comfortable living area, a fully-equipped...
Gorgeous Ocean View! Beachfront! Full Kitchen, Washer/Dryer, A/C, Wi-Fi!
Waikiki Shore #1110 – 2161 Kalia Rd.Not only is this beachfront OCEAN VIEW one-bedroom condo (706 sqft plus 124-sqft lanai/balcony) a favorite with our return guests, but Waikiki Shore is the only condo in Waikiki where you can step right from the building onto the...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo with Beach & Kid Amenities! HKK-225
Beautiful ocean view villa in the Konea building featuring a spacious 475-sq-ft lanai, and modern amenities. Perfect for up to 6 guests seeking comfort and luxury in Maui.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date...
Prime Wailea Location! Wailea Ekahi 37E
Limited-Time Offer: Stay 5 Nights, Get the 6th Night FreeBook a stay between October 09 and October 18 and enjoy the 6th night free - perfect for extending your getaway at no extra cost!Discover Hawaiian paradise at this beautifully decorated 1 bedroom, 2 bath premium...
Carefree In Paradise. Just steps to the beach!
Experience the classic charm of Napili Shores Resort while enjoying the modern comforts of this updated studio condo.The studio features a king-sized bed and a twin-size sofabed. You’ll find it conveniently located near several communal BBQs. The pool is close enough...
Maui Resort Rentals: Honua Kai Hokulani 402 – 4th Floor Oceanfront Crown Jewel 3BR w/ B.B.Q on Balcony
Commanding an incredible 4th-floor vantage point above the palm trees in the closest column to the ocean at the entire Honua Kai Resort, Hokulani 402 is without question one of the most sought-after "Ali'i" (Hawaiian word for royalty) residences on offer at Honua...
Elegant Windsor Waikiki Condo
Surround yourself in luxurious, island-style furnishings with spectacular views of Diamond Head and the crystal blue waters of Waikiki. This elegant corner unit(1046 sq. ft.) offers 2 spacious master suites, 2 full baths and includes a fully equipped gourmet kitchen,...
Coastal Keaau Home: Ocean & Sunrise Views, Pool
Spend your next exciting Hawaii getaway staying in style at this incredible Keaau vacation rental! Featuring a private outdoor pool, beautiful ocean views, and a prime location directly on the coast, this 5-bedroom, 2.5-bath house makes a perfect spot for a memorable...
Oceanfront - Beautifully updated - Ground Floor - Kuleana 607
Beautiful - Oceanfront - Ground Floor - Walk OutFabulous updated oceanfront condo location: Kuleana 607 is right on the ocean on Maui's pristine West Coast with gorgeous panoramic views of the Pacific Ocean and the lovely off-shore islands of Molokai and Lanai. This...
Kona Ali'i Condo in the Center of the town awaits your presence!
The heart of Kona, Comfortable secure condo in Kona Ali'i. 1 Bedroom / 2 Bath. Close to public transportation, shops and beaches. 3rd floor, Makau site with view of pool, mountains and ocean. Tidy unit has additional sleeping arrangements and can accommodate 4...
Spacious Townhouse w/ Shared Pool & Hot Tub, Private Washer/Dryer, & Mtn. Views
Villas of Kamali'i Apt 44Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sprawling mountain and golf course views make this home the friendly retreat of your dreams! Partial air...
Kihei surf side Great ocean view #309
Great location to beach and terrific snorkeling. New A/C unit installed in both living room and bedroom to keep you comfortable both day & night, new pillow top mattress, big screen TV, fast internet and stocked kitchen. Close to restaurants and rental shops for all...
Kihei Condo: Steps to Kalepolepo Beach Park!
Pack your sunglasses, swimsuit, and favorite beach read; it's time for your dream Hawaiian vacation! Check into this 1-bedroom, 1-bathroom vacation rental in Kihei, where you'll find everything you need for a relaxing stay. Start each morning with coffee on the balcony...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | Recently Remodeled 2-Bedroom Condo, Corner Unit! HKK-334
Spacious remodeled 2-bedroom, 2-bathroom corner villa in Honua Kai's Konea Tower offering expansive lanai with panoramic ocean and mountain views, plush amenities, and Wi-Fi.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date...
Stunning Princeville 3BR/3BA Home on Golf Course-Views, screened in Lanai🌴🌴
This is a beautiful three bedroom, three bath home on the second fairway of the Lakes Course in beautiful Princeville, Kauai. Enjoy the breathtaking views from literally EVERY room! Seriously--each room is like a 'Photograph'.. Split level design for entertainers...
Elevate Your Hawaiian Getaway at Lagoon Tower by Hilton – 2 Bd. Ocean View
Nestled within the stunning Hilton Hawaiian Village® Waikiki Beach Resort, the Lagoon Tower delivers a vibrant vacation experience that’s both luxurious and family-friendly. With breathtaking ocean views, spacious accommodations, and endless activities, this is the...
Maalaea 5 star Island Sands 501 1 bed Oceanfront
A wonderful just renovated modern unit on Maalaea Bay with a beautiful ocean view that was recently renovated with all new kitchen, bathroom, floor surfaces and furniture. The oceanfront pool is a wonderful place to spend the day followed by a wonderful evening and...
Wailea Ekahi Village 43B 1Bed/2Bath near quiet pool
This spacious one bedroom, two bath ground-floor condo is just steps away from one of four pools and a short walk through the beautiful grounds to the beach. Free parking a few steps away.This condo has a California king bed in the air conditioned bedroom and a fold...
Hidden Tiki Ohana at Punalu'u Black Sand Beach with ocean views, near Volcano National Park
**Special Fall Rate - Book your getaway today!!**Dramatic ocean and lava rock shoreline views, walk to black sand beach(All about Julie’s place)Relax and reconnect in one of the most stunning and serene locations in all of Hawaii! Sea Mountain Resort is a truly...
Panoramic Oceanfront & Diamond Head views, just steps to beach. FREE Parking!
Colony Surf #PH6 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)You'll fall in love with the amazing Diamond Head and ocean views from this 540 sqft 20th floor penthouse studio in...
Sugar Beach Oceanview SALE 165 May 17-31, SUMMER 180
Spectacular ocean front condo with views from every room in this 3rd floor elevator access. Feel the white sands of Sugar Beach between your toes! Sliding glass doors open from both the living room and bedroom, with the lanai offering comfortable seating to dine and...
Renovated w/ City View at Aqua Palms Waikiki
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...
🏖️Great Oceanviews | WIFI | Free Concerige | Top Floor | vrKCV
vrKCV - Sea Village 3310, Professionally Managed by Kona Coast VacationsEnjoy stunning sunsets and the shimmering city lights of downtown Kona as they reflect on the ocean waves from your top-floor condo at Sea Village. With tiki torches and exotic lighting enhancing...
The Most Amazing Haleiwa Beach Front Condominium
The Best of the Best! Relaxation - Romance - Recreation.Aloha! We love our slice of paradise and take great care to provide our guests with a relaxing experience. We are especially proud that it is always neat and clean so that our guests can begin their vacation the...
Modern and well-appointed 3bd oceanfront condo
Noelani 303 is a spacious and beautifully decorated three-bedroom, two and a half bathroom condo located on the 3rd floor and accommodates a maximum of eight guests. Enjoy this oceanfront view while staying cool inside from the split air conditioning system that...
Mana Kai 815: Top-Floor Kihei Condo with Stunning Panoramic Ocean Views
Mana Kai 815 offers water, beach, and palm tree views! One of the best condos in Kihei has sandy beaches, a reef for snorkeling, lounge chairs in shaded grassy areas, an oceanfront pool, kayaks, and paddle boards for rent right on the property. All making this the best...
Kona Plaza#210 REMODELED BEAUTY 1/1 IN HEART OF KONA TOWN! AC & Elevators!
Knutson & Associates Property Management is proud to be representing Kona Plaza#210. It's amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village.This 2nd floor unit of Kona...
Ground-Floor Oceanview Home w/Private Lanai, WiFi, Shared Pool + Lots of Privacy
Wailea Ekolu Village 203Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a prime location and all the comforts of home, Wailea Ekolu 203 is the perfect setting for your next Maui...
Kauai Princeville Luxury Vacation Home
Couples vacationing together will find that this home has an open layout and airy rooms suitable for a lively gathering with friends, while also offering space for some quiet-time and privacy.Princeville is the gateway to Kauai's north shore and a myriad of activities....
Keaau Getaway w/ Patio, 3 Mi to Shipman Beach!
Spend plenty of time exploring the beautiful beaches of the Big Island when you stay at this exciting Keaau vacation rental. Located just down the road from the stunning Shipman and Haena Beaches, this 3-bedroom, 2-bath duplex guarantees plenty of opportunities for fun...
Gated Community Located Within Walking Distance To The Beach
Welcome to The Ilio Hale!Our spacious, fully furnished, family friendly retreat is located within the prestigious gated subdivision of Kahakai Estates in Kailua-Kona on the Big Island, Hawaii. The historic Great Wall of Kuakini runs along the back of the property, while...