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.
Maui Kamaole B207 Two bedroom condo with Garden Views
Spacious Maui retreat at the popular Maui Kamaole in South Kihei. This two-bedroom condo features high ceilings and lots of room to entertain. The fully equipped kitchen is great for preparing meals to enjoy on the go or to be enjoyed in the condo. The primary bedroom...
Luxury Kailua-Kona: Kona Mansion 120-B Ocean/Timeless Sunset Views Awaits You
Experience the timeless magical views of Hawaii Big Island Ocean views in this spacious charming condo with 1-bedroom, 1-bathroom, fully furnished vacation rental in the heart of Kailua-Kona. Centrally located just moments away from top attractions/restaurants like Kona...
Anahola Palms - Beachfront Home on Anahola Bay
Located northeastern side of the Kauai on Anahola Bay, this is the perfect beach spot for a gathering of family and friends. Mornings start with oceanfront sunrises and your day continues with beach activities right outside your door. Evenings are backyard barbeques and...
Menehune 127 Partial Ocean Views in Well Maintained Condo Home
Book with us and come to Maui to explore everything we have to offer!This beautifully kept 2-bedroom, 2-bath, air-conditioned Menehune Shores resort condominium offers everything you need for a relaxing stay in Maui. The granite and stainless-steel kitchen is perfect...
Secluded Ocean front getaway
Summary:Relax with the whole family at this peaceful home. Our newly renovated oceanfront property is the perfect island getaway. With ocean and mountain views from your doorstep yet just minutes from the best local food and famous attractions you will enjoy the perfect...
Waikoloa Hills,Two-Bedroom/Two-bathroom BBQ & more
Welcome to Waikoloa Hills Unit 606, a beautifully appointed two-bedroom, two-bathroom vacation rental offering comfort, convenience, and mountain views. Nestled in the heart of Waikoloa Village, this two-story retreat is perfect for families, couples, or friends looking...
Two-story condo with Mauna Kea view, saltwater pool, hot tub - near beaches/golf
Waikoloa Hills #105 - Pineapple ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up each morning to a view of Mauna Kea from your bedroom at this two-story condo in...
Beautiful Condo located at Makaha Valley Towers
Recently remodeled guard gated condominium on the 6th floor of Makaha Valley Towers. Brand new furnishings and beautifully decorated, along with fantastic views from expansive windows. Very convenient to parking and elevators. Includes a spectacular community pool and...
Upgraded Condo Near Beach - Kamaole Sands 4108
Recently remodeled and with an open layout, this air-conditioned condo located in the quiet part of the Kamaole Sands resorts, is your perfect home-away-from-home. Great for preparing a full meal or warming up leftovers from one of Kihei’s trendy eateries, the fully...
New! Kailua-Kona Stunning House w/ Ocean Views & Infinity Pool
Welcome to Hale Luana, your dream vacation rental with extraordinary ocean views in a reimagined and refreshed Kona home. Located at the pinnacle of the highly regarded Iolani subdivision, this oasis offers the perfect island getaway with convenient access to Kailua...
Oceanfront Kailua-Kona Islander Studio w/ Lanai!
Switch into island time the second you land on the Big Island of Hawaii and get settled into your tropical home-away-from-home in the Kona Islander Inn. This Kailua-Kona vacation rental studio features 1 bathroom, a well-equipped kitchenette, a private lanai, and a...
Centrally Located 2 BDRM 2 bath Condo w/City, Diamond Head & Ocean Views
Aloha and Mahalo from Waikiki! This property is a 30 day minimum rental at The Windsor. Centrally Located near the main Waikiki strip and in one of the most convenient areas of Oahu. Featuring a fully equipped kitchen ready for you to cook, and great views from your...
Koana's Ocean Hale | Onsite Pool
Summary:Fall in love with the Big Island and all its splendors when you stay at Koana’s Ocean Hale, a charming 1-bedroom condo on Hawaii’s west coast. Nestled among the lush island landscape, you’ll be located alongside the beautiful Kona Country Club where the...
Cozy studio with a shared pool, hot tub and grill area, steps from the beach
Kona Bali Kai 263Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the beautiful area of Kailua-Kona, Hawaii, this charming condo at Kona Bali Kai offers a serene retreat...
KBM Resorts | FREE CAR | Mahana | Oceanfront | 2-Bedroom Condo with Stunning views! MAH-719
Oceanfront 2-bedroom, 2-bath condo at Mahana Resort with panoramic ocean views, private lanai, modern kitchen, and serene bedrooms-ideal for whale watching, relaxing, and island adventures.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an...
Newly Remodeled & Updated - One Block To Beach
Legally permitted rental -134 Kapahulu Ave #411** For your health and safety, we utilize additional Sterilization procedures between reservations.Great View & Balcony.Recently remodeled, painted and upgraded as of November 2018 - park, zoo and ocean views from this...
Kauai, HI: 1BDRM with Free WIFI, Pool Near Beaches, State Parks, Shopping & More
A spacious escape that is both stylish and inviting, the One-Bedroom Suite offers 1,050 square feet and accommodations for 4 adults with a King bed, a master bedroom and a queen-size sleeper sofa in the living room. Beautifully designed for modern living, the suite...
Amazing Ocean and Diamond Head Views
Breathtaking ocean view while also being able to see Diamon Head! This beautiful condo in Waikiki Sunset boasts the comfort of central AC while bringing you right to the beach.. With close proximity to the beach shopping and restaurants it is a perfect place for your...
Remodeled 2 bedroom oceanfront gem on 6 mile Sugar Beachn
Welcome to Kihei Beach Resort 501. This remodeled 5th floor 2 bedroom 2 bathroom condo is ready to be your Maui home away from home. Beautifully updated & perfectly located on the sandy six mile stretch known as Sugar Beach. This condo accommodates 6 people and features...
Exquisite oceanfront condo with beach access
Welcome to Hale Mahina A104, an exquisite oceanfront retreat nestled on the picturesque shores of Maui. Thoughtfully designed to provide the utmost comfort and relaxation, this one-bedroom, one-bathroom unit can accommodate up to four guests. Upon entering the...
Ilikai Apt 2127 - Spacious Studio with Spectacular Ocean & Harbor Views
Breathtaking Ocean & Yacht Harbor Views | Ilikai Studio, Sleeps 4 | Waikiki Paradise! Step into your dream Waikiki vacation rental—a bright and breezy studio suite located in the legendary Ilikai Hotel. Perfectly situated on the 21st floor with stunning views of the...
Kihei Surfside #512: Luxe Oceanfront Escape with Gorgeous Views!nnn
Kihei Surfside #512 – Oceanfront Comfort with Bedroom Split-Duct AC and Expansive ViewsWelcome to Kihei Surfside #512, a spacious 1-bedroom, 1.5-bathroom oceanfront condo offering wide-open views of Maui’s southwest coastline and the neighboring islands beyond....
Coconut Plantation 1080-1: Spacious 3BR Ko Olina Retreat w/ Wrap-Around Lanais
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Coconut Plantation 1080-1 by...
Kihei Akahi C-410 | Ocean Views, Near Area Fun!
Welcome to Paradise! Live out your Maui vacation dreams at Kihei Akahi C410, a fourth-floor upgraded condo in Kihei, HI. This gorgeous condo offers rest and relaxation for up to two guests with one bedroom and one full bathroom.The moment you step inside Kihei Akahi...
Spacious Entire Home w/ Heated Pool, 180-Degree Ocean View & 7 mins to Beaches!
Welcome to Phil's Kupuna home! * Escape to paradise in this spacious, coastal retreat, where relaxation meets productivity. Featuring a swimming pool, 180-degree ocean views, and an office room perfect for remote work, this home offers the ideal blend of comfort and...
Exceptional Condo offering Peace and Serenity
Nicely decorated ground floor condominium across from Kamaole Beach Park III. This 1 bedroom, 2 bath unit has not one but two garden view lanais. A private lanai off of the bedroom perfect for reading or meditation and another one off of the living room with a table set...
Shores at Waikoloa Unit 111: 1 Br condo in the Tamarind Tower, sleeps 2
A Repair and re-tile project on the 2nd-floor walkway (catwalk) in the Tamarind Tower will start the week of April 21st, 2025, with plans to be completed late-June. While the walkway will remain accessible when under construction, there will be considerations for all...
Island Style W/Ocean View, Lanai and Fans–Kiahuna
Kiahuna Planation and Beach Bungalows #2072: Settle-in under tall ceilings, stunning ocean views, and a spacious open-concept design in this vacation suite. This space features warm and cool gray tones highlighted by tropical scenes and sets the standard for peaceful...
Kihei Akahi Condo w/ Free WiFi, A/C-Swim, Surf, and More
Kihei Akahi D601Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step across the street and enjoy Kamaole Beach Park II, one of Maui’s best swimming and stunning beaches. Revel in...
Gorgeous Ocean Views & Interior - Menehune Shores #209
Menehune Shores is an oceanfront property located in North Kihei, offering breathtaking views of the Pacific Ocean and easy access to a sandy beach. This family-friendly condo features spacious interiors and is perfect for groups, with its proximity to a protected beach...
Mauna Lani Point | J103
Welcome to Mauna Lani Point J103, a newly renovated two-bedroom, two-and-a-half-bath vacation rental on the breathtaking Big Island of Hawaii. Nestled in a serene location with captivating golf course views, this property offers the perfect retreat for those seeking...
Rare 2 Bedroom + Loft Townhouse on the North Shore
Affordable 2-Bedroom, 2-Bath + Loft at Kuilima Estates (next to The Ritz-Carlton O'ahu, Turtle Bay)Enjoy more space without the luxury price tag! This comfortable and spacious 2-bedroom, 2-bath loft is the largest floor plan in Kuilima East, giving you room to spread...
Royal Kuhio 1309 with King Bed, FREE Parking/WiFi, mins to BEACH!
Discover Waikiki Bliss at HOME Honolulu - Royal Kuhio 1309Embark on an unforgettable Hawaiian escape at our meticulously designed vacation rental, situated at the heart of vibrant Waikiki. Located at 2240 Kuhio Ave #1309, this King Studio promises an immersive 30-day...
Lovely Hawaiian decor with oceanfront views
Welcome to Paki Maui 310, a charming 1-bedroom, 1-bathroom unit that offers ocean views from your private lanai and ceiling fans throughout. This property does not have elevators. Unit 310 can accommodate up to 4 guests. The bedroom features a queen-size bed and natural...
Ocean View Studio with Kitchenette - Waikīkī Grand #910
Castle at Waikīkī Grand #910 - Make coffee in the morning in your coffee pot, warm up leftovers in the microwave, or cook a small meal on the hot plate all from your own kitchenette! Whatever your fancy, you'll have everything you need to warm up leftovers or to cook...
Kihei Akahi D-104 | Lush Garden Views & Steps to Beach + Fun Amenities!
Lush garden views from your private lanai await you at Kihei Akahi D-104. Discover island-inspired comfort right across from the sun-drenched shores of Kamaole Beach Park II. Perfect for a romantic retreat or small family getaway this Maui, Hawaii vacation condo offers...
Lae Nani 313 Drastically Reduced Rates!
Rates have been drastically reduced to entice last minute travelers! This condo is very close to the beach. It is locatedon the ground floor so you can just walk to your beach without a staircase to obstruct you.You can relax on the lanai, amongst our beautiful...
Updated 2nd-floor condo in heart of Kona with lanai, pool, grills
Kalanikai 218Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This nicely updated, second-floor condo (no elevator) is in the heart of Kailua-Kona and is perfect for a romantic...
Ocean Views & ac W763! Sullivan Properties
Enjoy all that Kaanapali has to offer within walking distance. The 3 mile beach walk stretches from Sheraton’s Black Rock to the Canoe Beach just pass the Hyatt Regency Maui and your condominium at The Whaler is right in the middle. The location on Kaanapali Beach is...
Hawaiian King Retro Oasis 1-Bedroom | Lanai | Pool
This one bedroom apartment at the Hawaiian King building will take you back in time to retro Waikiki. Located in the heart of modern day Waikiki, right off popular Kuhio Ave, enjoy easy access to world-renowned shopping, dining, and entertainment! Our unit features one...
Wailea Grand Champions | 116
Wailea Grand Champions 116 is a luxurious vacation rental located along the southern coast of Maui in the desirable tourist area of Wailea. This beautifully appointed one-bedroom, two-bathroom condo accommodates up to four guests, making it ideal for families or groups...
New Listing! Ground floor oceanfront blue oasis
Nohonani 101 is a spacious two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. With a king-size bed in each bedroom and a queen sleeper sofa in the living area, there's plenty of room for families or small groups to relax and unwind. Although...
Kalia Suites, a Hilton Grand Vacations Club - Studio
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Kona Mansions#225 Top Floor, 2 story Unit w/Ocean views & Air Conditioning
Knutson & Associates is proud to be newly representing a spectacular new addition to our Vacation Rental Inventory. Kona Mansions#225 is a wonderfully appointed property that has a phenomenal location. Stunning ocean views, just steps from lively nightlife and the best...
Kailua Studio w/ Pool Access & Garden Views!
Indulge in paradise when you stay at this vacation rental studio in Kailua! Located at Kona Islander Inn, the home has a queen Murphy bed and 1 bathroom. Take advantage of great community amenities including a hot tub, or stroll across the street to sunbathe at the...
Island Surf 510B | Close to Beach & On-Site Pool!
Escape to the serene paradise of Island Surf 510B, a cozy tropical condo nestled in the heart of Kihei, Hawaii. This charming vacation rental offers a tranquil retreat for up to 2 guests, boasting 1 spacious bedroom and 1 bathroom all conveniently situated on one floor...
Coastal condo w/ breathtaking ocean views, shared pools, WiFi
Country Club Villas 234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the ultimate Hawaiian getaway at this stunning ocean-view condo nestled along the iconic Ali'i Drive...
Island Surf 209 One Bedroom One Bath with Ocean View
If you want to be within walking distance to all the best food and fun to be found in South Maui, this is the property for you! This stunning ocean view condo offers an unparalleled blend of comfort and luxury. As you step into the spacious, sunlit living area, you’ll...
OceanView Studio Waikiki Legal
About this spaceIndulge in a breathtaking ocean panorama from your recently renovated lavish studio situated on the 25th floor of the magnificent Waikiki Beach. This condominium is designed for discerning travelers seeking a roomy,and contemporary space measuring a snug...
NEW LISTING, The Queens Bluff 3 bedroom, AC, Ocean View!
Experience the ultimate Hawaiian getaway at Queens Bluff, a luxurious vacation rental located in the heart of Princeville, just steps away from the renowned Queen's Bath. This exquisite home offers the perfect blend of comfort, elegance, and breathtaking natural beauty,...