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.
Waipouli Beach Resort A103 1st Floor Beautiful Garden View Steps from the Ocean
Special* Book Now & We Pay Your Daily Resort Fee's! No hidden fees, what you see after selecting your dates is the total price. The Waipouli Beach Resort is a new concept in luxury accommodations on the lush island of Kauai, Hawaii and is centrally located within easy...
Aston Kaanapali Shores - Oceanfront Treasure
Maui Gov’t Approved Short Term Rental. This amazing condo looks out to the Pacific Ocean from the upscale Aston Kaanapali Shores resort. The condo has gone through a stunning major renovation. The condo includes a new state of the art kitchen that includes everything...
OCEANFRONT RESORT - 5* LUXURY $349 to 5/15! Kihei Sands Beachfront Condos-B11
This HIGH-END five-star luxury condo's impeccable remodel was made with your comfort in mind. Kihei Sands' ONLY true 2-bedroom unit has a full upper floor - NO LOFT - PRIVATE BEDROOMS - PERFECT for two vacationing couples! Now's the time to book your holiday vacation &...
KKSR#1103 DIRECT OCEANFRONT, GROUND FLOOR, REMODELED, INCREDIBLE LOCATION
Keauhou Kona Surf & Racquet Club#1-103 DIRECT OCEANFRONT, INCREDIBLE GROUND FLOOR FULLY REMODELED UNIT!Welcome to unit #1-103 at the Keauhou Kona Surf & Racquet Club! Knutson & Associates Property Management is so proud to be newly representing this absolutely...
The Bungalow at Waimea Bay Point
The cozy North Shore Waimea Bay, 3 bedroom bungalow sits just a minutes walk away from two different world class white sand beaches and is centrally located on the most prime shoreline location of Oahu's North Shore. The ocean zone in front of the property is a...
THIS DOESN'T GET BETTER....Welcome to PARADISE! YES YOU CAN HAVE IT ALL! HEAVEN!
JUST INSTALLED SPLIT AIR CONDITIONING IN ALL THE ROOMS... ULTIMATE IN COMFORT, BRAND new 75" smart tv.... in 2022; New floors, paint, doors, linens, furniture, lights in fans, and and more;). this PERFECT LOCATION TO THE BEACH.... AMAZING MEMORIES, JUST TO START;)...
Ocean View - Studio - Westin Kaanapali Ocean Resort Villas North - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using their...
Luxurious 2BR/2BA in Poipu, Kauai: Island Paradise Awaits at Nihi Kai 507
Welcome to Your Tropical Retreat at Nihi Kai 507!Step into relaxation and luxury in this beautifully remodeled and professionally decorated 2BR/2BA split-level condo, one of the most sought-after spots in Poipu. With air conditioning throughout and thoughtful upgrades...
Savor The Best - Beautifully decorated with Golf Course And Ocean Views
Come enjoy Paradise the way it was meant to be experienced, in this 4 bedroom, 3.5 bath Luxury home in the new KaMilo development. Nestled at the edge of the 11th green of the Francis H. I Brown North Course, this unit's stunning Golf Course and Maui views await the...
Hale Kamaole 218 Second floor condo, easy access to best beach on Maui!
Good Ocean View and mountain View. Very updated condo with extra spacious kitchen cabinets. New walk-in shower with remodeled bathroom cabinets. King bed in bedroom and queen hide-a-bed in living room. Rattan bedroom furniture. Comfy furniture in living room. Full...
5 Star Must See C102 Maui Eldorado Kaanapali
Aloha! We welcome you to enjoy your next vacation at the Maui Eldorado Kaanapali C102 in this designer decorated 1 bedroom vacation condo - perfect for a couple, or a family up to four! This newly remodeled condo was just completed in end of 2020 with wood tile...
Snowbird-friendly oceanfront condo with heated pool, lanai, and amazing views
Poipu Shores 101COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Don’t just vacation in Hawaii, live in total luxury at Poipu Shores 101C with central air-conditioning and porcelain...
Newly renovated piece of paradise. Experience Old Hawaii at its best.
Located just past the town of Hawi in North Kohola, this historic Plantation House dates back to the 1940's when the Union Mill company farmed the land for sugar cane. It once belonged to the plantation doctor. Our renovation has focused on maintaining the style and...
Aloha Villas 1 Breathtaking Ocean View, Steps to the Beach, Great Location
Summary:"Ehaki" - Aloha Villa #1 offers unparalleled luxury and beachfront elegance in a great location with breathtaking ocean views and quick access to the beach.The Space:Escape to serenity at Ehaki Villa, your beachfront oasis in South Maui. Wake up to the sound of...
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
Big Discounts for Last Minute BookingsYour support is appreciated as a small private family owner who lives on Maui instead of renting from a large management company.Welcome to our 3 bedroom, 2 bath Cloud 9 Beach House right on the edge of Wailea. This property is...
Perfect Getaway! Newly Updated Condo! Steps to Beach & Dining! Read our Reviews!
Escape to paradise in our beautifully renovated one-bedroom condo in the popular Kihei Alii Kai complex in South Kihei! Just a one-block stroll from the golden sands of Kamaole Beach Park I, our "home away from home" is the perfect retreat for couples seeking a relaxing...
North Shore Oahu: Stunning Beachfront Custom Home
Welcome to our custom-built beachfront home on Oahu's picturesque North Shore! This stunning property is designed to provide you with the ultimate beachside retreat, complete with breathtaking ocean views.As you step inside, you'll be greeted by an open and spacious...
Kehena Beach Oceanfront Retreat - Incredible Views of Ocean from Every Room
Discover the ultimate oceanfront retreat on the Big Island at Kehena Cliffside Estate — a private, gated luxury rental designed to showcase breathtaking views of the Pacific Ocean from nearly every room. Nestled along the dramatic cliffs of Kehena, this spacious...
Oceanfront Beach House Makai
Minimum 30-day consecutive rental required. Please contact the Host for availability. Oceanfront 3-bedroom home on private, gated property. This unique property offers year-round swimming, private beach access, and astounding ocean and mountain views.This unique,...
Panoramic Oceanfront & Diamond Head views, just steps to beach. FREE Parking!
Colony Surf Penthouse #6 – 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...
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...
BEACHFRONT LEGAL PRINCESS CONDO VIEW FREE PKG/WIFI, POOL,HOT TUB,TENNIS/PICKLE 6
*See AC info below please!FREE PARKING & HI-SPEED WIFI! NO RESORT FEES!BEACHFRONT! AWESOME! 180º UNOBSTRUCTED OCEAN & SUNSET VIEWS! LIGHT, BRIGHT, AIRY, AND SUPER CLEAN CONDO THAT SLEEPS 4! POOL, HOT TUB, TENNIS, PICKLE BALL, PING PONG—2 OUTSIDE SHOWERS & BBQ...
🏖️Oceanfront 5 Bedroom Home | Pool | Close to Beaches | vrKCV
vrKCV - Hale Kipa, Professionally Managed by Kona Coast VacationsSituated directly on the ocean, this 5-bedroom 3-bathroom home has a gated entry and is located on Alii Drive, close to beaches, shopping & all the activities that the Big Island has to offer! The main...
Poipu Kapili 22 - Ocean Views * Deluxe Furnishings * Central Air Conditioned
Oversized 1 bedroom / 2 full bathrooms; ocean views from premium 2nd floor location Spectacular views and deluxe furnishings will make Poipu Kapili #22 your home away from home. This spacious and comfortable home has an air conditioned master suite and living room....
Luxury 3br Poipu Estates Home w Private Pool
This home is a true Poipu gem. Located in the Poipu Beach Estates neighborhood, this home features a spacious open floor plan with a covered lanai. The kitchen flows seamlessly into the living area creating the perfect place to gather and “talk story.” All of the...
AC!! Stunning Ocean Views - Walk to the beach #133-134
Cleaning is always a top priority and we are committed to ensuring the safety of our cleaning staff and guests. In addition to our normal full cleaning extra disinfecting includes all highly touched areas such as handles, knobs and switches. This condo has everything...
This Pic is Your Gorgeous Ocean View~Top Floor~Beachfront~Free parking, WIFI, AC
Aloha and welcome to our TOP FLOOR, gorgeous panoramic OCEAN VIEW, ISLANDER ON THE BEACH unit 341 in Kauai. Direct ocean view unit! This is a beachfront property. You are steps to the white sand Wailua beach. You get this ocean view everyday!Our unit offers the exact...
OCEANFRONT- THE WHALES ARE HERE! Kihei Sands Beachfront Condos - A9
Maui's Magical whale season is officially underway! Enjoy front-row seat seats from your own lanai as humpbacks breach and play just offshore. With our special seasonal pricing, you can witness nature's most incredible show while relaxing in tropical paradise!Are you...
Totally renovated, closest to the beach! Last minute specials!
TOTALLY RENOVATED & CLOSEST TO THE BEACH!! Welcome to Ekahi 20e! Our total renovation is now complete! After a day at the beach, relax on our super comfy furniture and watch our 50" Sony Bravia smart tv , or enjoy your playlist using our Yamaha Bluetooth sound bar. All...
Home Away from Home, totally renovated.
We have fully renovated the unit as of December 2013, and decorated it in a Hawaiian motif. We've installed new all wood cherry kitchen cabinets, granite counter tops, appliances, and kitchen utensils. Along with new paint throughout the condo. Both bathrooms have been...
Beachfront ,Groundfloor, Oceanfront Corner unit 114 - Steps to the Beach!!!
Feb and March 26 open dates still available !- Discounts and good ratesUnit 114 is beachfront Kihei -w perfect sunsets and wonderful fresh mornings - Remodeled and upgraded w/ granite countertops, new cabinets, crown molding- our unit is new ! Stainless appliances- Plan...
Ko’Olina Kai 1041F 30 day minimum rental in beautiful 2 BR ground floor villa.
This professionally decorated first floor end unit is located in a gated community just a five minute walk to the golf club or the shops at Ko'Olina Station. Each bedroom features a King Bed with lots of pillows, and ample closet space. There are two big screen TVs...
Puu Poa - Magnificent Oceanfront Condo
*Updated Magnificent Vacation Home* Incredible Ocean Views, Sounds, & Breezes* Directly on the Ocean, Bali Hai views* Updated Kitchen, Hard Wood Floors* High-speed Internet, 60 inch and 40 inch HDTV with extensive premium cable channels plus Netflix* New Furnishings,...
Luxury Mauna Lani Resort Villa - Beach Access!
Escape to the 'Paradise of the Pacific' with a stay at this idyllic 3-bedroom, 3-bath Mauna Lani villa! Guests will enjoy all of the comforts of home, as well as community amenities like an outdoor pool, spa, and historical fish ponds and trails on-site. This Kamuela...
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...
Oceanview Poipu Studio Condo with Pool, Gardens, Steps from the Ocean!
We welcome you to our little piece of paradise!Our lovely, oceanview, air-conditioned condo looks out on Prince Kuhio Park and beyond to the beautiful Pacific Ocean. Our place is the perfect honeymoon destination or a romantic getaway . . . . Enjoy ocean views and...
Upgraded! Steps to Kamaole II Beach, Sunset Views, Pools & Tennis #H505
Your dream Maui vacation awaits you at this beautifully upgraded condominium located across the street from Kamaole II Beach Park. Surrounded by lush tropical landscape, Maui Banyan is just steps away from restaurants, shops, and ocean activities. The island of Maui...
Right on the water! End Unit! C206
For the most memorable vacation, come stay with us at C206 Lokelani! C206 is the closest two bedrooms unit to the beach access. This 1350 sq. ft. unit has 2 bedrooms and 2 full bathrooms with large ocean front lanais on each level. The townhouse style will accommodate...
Waikiki Sunset * Newly Renovated * Parking * Diamond Head Ocean Views *
One bedroom One Bath with Ocean and Diamond Head views from Bedroom, Living area and lanai. Relax in the morning with a cup of morning coffee on the lanai to start your vacation. Full Kitchen complete with all you need to cook breakfast, lunch or Dinner. Rather BBQ.....
Cute, Peaceful Budget-Minded Studio Condo with full kitchen and Hawaiian Decor
Located on the Princeville Resort Makai Golf Course, this peaceful, Hawaiian style 600 Sq Ft condo has a private lanai, dedicated parking and a pool on site. Between the golf course and the lanai is the Queen's Carriage tree tunnel trail where you can walk in about 5...
Prince Kuhio Poipu ~ Ocean View, quiet, comfortable, end unit-ground floor
Welcome to Kauaʻi's sunny Poʻipū. Enjoy a cozy comfortable stay in our superbly situated ground floor quiet, private end unit. This studio opens onto an east facing lanai with gentle trade winds overlooking the historical Prince Kuhio Park. Enjoy a slice of the...
A Princeville Suite for all your Needs
This comfortable island suite is only 15 minutes from magnificent Hanalei Bay and just a short stroll to Queen's Bath, Hideaways, and Aninni Beach. And a short distance to shopping and restaurants. This charming suite has a large living, dining area and one bedroom with...
Hale Akaka Falls O-121 one of a kind luxury stay
Welcome to Paradise at Hale Akaka Falls O-121Discover the beauty and elegance of this stunning three-bedroom, three-bath villa located in the prestigious Beach Villas at Ko Olina Resort. This luxurious, ground-floor home offers a rare combination of comfort, style, and...
Kaanapali Royal Luxury Spacious Condo with Ocean View (sleeps 4-6)
Ocean View Condo within walking distance to Kaanapali Beach (voted one of the best beaches in America) and Whaler's Village, a popular dining and shopping complex! The spacious, over 1700 square foot property sits on the 16th fairway of the Royal Kaanapali Golf Course...
5A - 2 Minute Walk to the beach/main pool, well-equipped, see reviews!
Hawaii Tax ID: W66713090-01 Oceanfront complex, one-bedroom, two-bath, single-level, ground-floor unit. REMODELED.Quiet location. NO TRAFFIC NOISE (you are in paradise there should be none), very close to beach and main pool pavilion (2 min walk). Beautiful Garden View...
Christmas/Xmas and New Year's Weeks 51 & 52 @ Marriot's Maui Ocean Club Hawaii
Christmas and New Year's Eve at the Marriott Maui Ocean Club doesn't need much of a detailed explanation and its pretty much equivalent to the best two weeks of the year in paradise.The listing is for a 1 Bed / 2 Bath Garden View Villa with one bedroom, living room, two...
Oceanfront Penthouse Condominium Spectacular Beachfront View
This Menehune Shores Condo is unit #620 and is an oceanfront/oceanview penthouse, which has 885 square feet with two bedrooms and two baths. The master bedroom is on the oceanside of the building and has a King-size bed. The second bedroom has a Queen bed plus a pull...
Modern Kaanapali Royal 2BR - Pool, Beach, Views, Golf Access
***Update as of January '26 - Please be aware that Kaanapali Royal has a solar installation project. While the majority has been completed, there may be some daytime noise. *** Kaanapali Royal - large modern two bedroom, two bathroom condo, surrounded by lush, tropical...
2 BDRM w/ 5 Beds + 2 Bath + Parking + Peekaboo Ocean View, 2 min from the beach
Legal vacation rental at a fabulous location! This renovated 1000 sq ft, 3 bedroom 2 bath with 2 balconies home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! This unit comes with 1 FREE dedicated parking stall...
Napili Shores A-201 - Get Your Spring/Summer 2025 Dates Booked Now!
Napili Shores A201 is an oceanfront studio unit within the Napili Shores Resort on the beautiful Island of Maui. The resort's A building directly faces and has an unobstructed view of beautiful Napili Bay, frequently called the Jewel of Maui. Swimming, snorkeling,...