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.
Kauai Kailani - Steps to Beach Oceanfront Pool - Fully Renovated 2 Bdm Condo
Kauai Kailani a Beautiful Garden View! A 2 Bedroom Condo located along the famous Coconut Coast on Beautiful Kauai East Shore!The Experience: Peaceful in this nicely decorated condo just steps to the beach!And, there is AC in this condo! Sleeps up to 6! King bed, 2 Twin...
Oceanfront IS310 - Charming One Bedroom Maalaea Bay is an Incredible Value
Experience the breathtaking views and serene atmosphere of Island Sands #310. This oceanfront condo offers a stunning panorama of the Kihei coastline and the majestic Haleakala. From December to mid-April, witness the spectacle of Humpback whales birthing their calves...
Kona Coastal Getaway – A Short 5 min Walk from Beach, Shops & Vibrant Ali‘i Dr!
Experience the best of Kona in this bright and inviting retreat! Located within 5 min walk to grocery stores, Historic Ali‘i Drive, downtown, and the pier, this cozy getaway offers the perfect blend of convenience and island charm. Enjoy the airy living space, modern...
Stylish Ocean View Condo Near Waikiki Beach with Free 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...
Beautiful Hali'i Kai Villa in Waikoloa Beach - Recently remodeled!
Welcome to our beautiful two bedroom, two bathroom villa in gorgeous Hali’i Kai. Located in the world-famous Waikoloa Beach Resort, our fully furnished villa will pamper and refresh you with breathtaking views and freshly updated modern conveniences. Fresh paint,...
Waterfront Condo with Resort Pool & Hot Tub - Short Drive to Lahaina
Paki Maui 423Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to paradise! Kick back on the classic Hawaiian rattan love seat in this two-bedroom, two-bathroom condo and soak...
Let our 2nd home be your 2nd home! Vacation in the beautiful islands of Hawaii! Our quiet little complex consists of only 48 units on over 4 acres of tropical paradise! From our ground floor unit you can sit back and enjoy the breathtaking views of the sun setting over...
Beachside Bungalow Remdld 2 BD/2BATHBATH GR FL Walkout Suite -5 MIN from Beach!
Aloha! . Maui Banyan is an ideal and popular vacation getaway, conveniently located in South Kihei, just a short walk away from the beautiful Kamaole Beach Park II (lifeguard-attended) and the nearby shops and restaurants. The grounds are beautifully landscaped &...
Completely updated room as of April 2025!! 3rd floor ocean & pool view. Our condo hotel room offers one of the best views on the property! If a gorgeous well kept resort is what you're looking for, look no further. Enjoy a cup of coffee in your room or lanai admiring...
Considered the Best Location Oceanfront on Maui
The Maui Sunset is located on over 5 acres of ocean front in Kihei, which is considered one of the best locations on the Valley Isle. Kihei is noted for its year round sunshine, balmy trade winds and soothing evening air. It is one of the driest and sunniest areas on...
Hawaiian condo with WiFi, shared pool & hot tub - close to golf, beach
Plantations at Princeville #1312Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This fabulous, ground-floor condominium offers two large bedroom suites and access to a shared hot tub...
Spectacular Views & Ammenities
PACK LIGHT! Welcome to our cozy Lil Piece of Paradise inside Kauai Beach Resort, your home base for an unforgettable Kauai getaway.Premium top-floor comfort with the resort’s best view, our updated suite hosts up to 4 guests in two queen loft beds - perfect for a...
🌴Hotel Room w/in beautiful Oceanfront Condo.🌸
You will enjoy easy access to everything from this centrally located place. This 3rd floor room is a part of Kauai Kailani Condo's with an ocean view from your room. Enjoy the coastal breeze or use the air conditioner. The room is equipped with a microwave, mini-fridge,...
#02 Kawela Kai 495:North Shore Beach Front---Relax & Unwind
LEGAL SHORT-TERM RENTAL! CERTIFICATE:1990/NUC-2056 LICENSE# 90/TVU-0003 TAX MAP KEY: 1-5-7-005:006This home is not affected by the new Honolulu County ban on vacation homes. Make sure when booking your vacation home the property that you are reserving has a Short-Term...
Experience Oceanfront Luxury at Kanai A Nalu 209, a Spacious 2-Bd/2Ba Condo, AC!
Kanai A Nalu 209 is a newly renovated 2-bedroom, 2-bath ocean view condo located in the Kanai A Nalu resort in Maalaea, Maui. This second-floor unit offers stunning south-facing views overlooking the tropical courtyard, pool, and the Pacific Ocean .The condo features...
Peaceful Island Escape Condo with four pools near all the best things in Maui!
1 Bedroom + 1 Sofa bed, 1 Bath Maui Condo that Sleeps 4 - That could be your comfortable & fun home-away-from-home while in Maui!Welcome to the description of our condo at Wailea Ekahi, a privately owned, beautifully landscaped, condominium community located on...
Luxury Oceanfront Condo at Sugar Beach Resort in Maui sleeps 4.
Greeting Sugar Beach Resort Lovers!Amazing ocean view beach front condo that captures the magic of Maui with contemporary elegant style situated on popular Sugar Beach! Take walks on the sandy beach for miles or swim in the warm ocean waters in front of the condo. Enjoy...
KKSR#3 DIRECT OCEANFRONT TOWNHOME! Walk to the Beach! Superb Location! AC!
Welcome to this incredible oceanfront townhome in the heart of historic Keauhou! This 2-bed, 2-bath townhome offers the perfect blend of privacy and convenience sleeping a maximum of 4 guests.Air Conditioning now fully installed throughout the condo!With some incredible...
Oceanfront 1-BR Condo in Waianae w/ Sunset Views
Escape to this oceanfront 1-bedroom condo at Hawaiian Princess Makaha in Waianae. Ideal for couples seeking a romantic Hawaiian getaway, the unit features breathtaking views of the Pacific, modern amenities, and direct beach access. Relax on your private lanai or...
Country Club Villas - Golf, Air Conditioning & Oceanview
Summary:Country Club Villas are located in an exquisite setting with panoramic ocean views on the 17th and 18th fairways of the Kona Country Club. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:The tropically landscaped property is...
Wailea Serenity | 2 Bed, 2 Bath
Summary:Wailea Serenity - 2BD - Private, Quiet; the tropical paradise you dreamed about!The Space:This Grand Champions condo (#15 in building #2) is located in the heart of beautiful Wailea, a short walk to the beach, and in the middle of the renowned Blue Golf Course....
KAUAI Poipu Beach Escape to Tropical Paradise!...Beautiful Mountain views!
Beautiful sunny Poipu on the sunny south side of Kauai!This new home is one of the best south shore Kauai locations!For inquiring couples celebrating their honeymoon or anniversary, we are offering a free gift for your special trip by using the code "LOVE”.Also, enjoy...
🏖️Lagoon View | Ground Floor | WIFI | Nicely Upgraded | vrKCV
vrKCV - The Shores at Waikoloa 114, Professionally Managed by Kona Coast VacationsWelcome to Your Hawaiian Oasis!If modern comfort is what you're looking for, look no further. Relax and unwind in your Hawaiian home away from home. As you step inside, a beautiful view of...
Oceanfront condo with ocean view, private washer/dryer, and access to pool
Hololani B504Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Limited time summer discount. Holy whale watching, Batman! Watch spectacular sunsets from the comfort of your lanai at...
🏖️AC | Top Floor Corner Unit | Ocean View | vrKCV
vrKCV - Kona Isle C31, Professionally Managed by Kona Coast Vacations.Welcome to Your Kona Paradise!E Komo Mai! We invite you to enjoy our little piece of paradise. Start your day with a cup of freshly ground Kona coffee on the lanai as you soak in the breathtaking...
East Hawaii - Ocean, Mountains & Waterfalls
It’s your time to visit the magnificent Big Island of Hawaii with its ocean, mountains, waterfalls, beaches, and endless activities. The Umauma Experience Makani Ea Home is your own piece of paradise waiting for you and your family! It’s a cute 2 bedroom with an office...
Steps from the beach! Pool, Grill, & Hot Tub! Beautiful sunset views!!!
Welcome to My Hawaiian Beach View, your perfect getaway nestled in the heart of historic downtown Kailua-Kona. This newly remodeled condo offers an unparalleled Hawaiian experience, combining breathtaking ocean vistas with the authentic, vibrant energy of Alii Drive,...
Renovated and clean studio in Waikiki for two with amazing views
Walk to Waikiki beach, convention center, Ala Moana mall, restaurants, shops and many other Waikiki attractions in this newly renovated unit with a queen bed, full bath and kitchenette. The building offers a pool, Jacuzzi, large sun deck, barbecue grills, gym (one time...
Updated Ground-Floor Condo on Golf Course with a Shared Pool, Gym, & Fast WiFi
Waikoloa Fairway Villas D3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this beautifully-renovated, ground-floor condo located right on the fairway! Sip your Kona...
Waikiki Beach center! Oceanview, Lanai, Free WIFI and Phone. Full Kitchen.
Our recently upgraded vacation rental with great beach and ocean views from your private lanai (balcony) is now available! It is literally a 1-minute walk to the beach!!!It is a nicely furnished studio with new cabinets and granite counters, a full kitchen, and a large...
2-Bedroom Condo Just 8 Minutes Walk to Waikiki Beach
Find yourself right in vibrant Waikiki, enjoying your dreamy Hawaiian vacation in this fabulous two-bedroom condo. Nestled just a 12-minute walk from the renowned Waikiki Beach Walk, 14-minute walk from the Ala Moana Center, and 15-minute walk from the vibrant Royal...
VI 401 Remodeled OceanFront Condo w Ocean Views Pool
Valley Isle 401 Beautifully Remodeled OceanFront 1Bedroom, 1Bathroom with Amazing Sunset and Ocean Views. Ideal for Whale Watching and Located Minutes From Famous Maui Beaches Make Valley Isle 401 your oceanfront home away from home for your next Maui vacation. With new...
"Picture Perfect: Oceanfront Gem on the Top Floor at Wailua Bay View!"
"Picture Perfect" Oceanfront Beauty Top Floor at Wailua Bay View!View of the Sea from this cozy condo! Sun, Surf, and white sand beaches are calling you to come and relax. Let the view take your breath away and the sound of the waves your soul. Stylish decorated condo...
Oceanfront 1bd private lanai & endless ocean view
Welcome to Mahana 804, a beautiful 1-bedroom, 1-bathroom getaway that offers direct ocean views, a washer/dryer, and central A/C located on the 8th floor and can accommodate up to 4 guests. The bedroom features a king-size premium mattress, strategically designed to...
Big Island "Whole House 5BR/2BA" Retreat For Work & Play! Sleeps 16
The Mele Vacations property is a lovely property nestled in the heart of Hawaiian Paradise Park neighborhood. There are large fruit trees that bear a harvest for your picking pleasure along with comfortable furniture, large lanai, free open wireless Internet and long...
Hale Kamaole 156 Ground floor condo, easy access to best beach on Maui!
Cozy One Bedroom unit with both Ocean and Garden View, overlooking tennis court, close to pool and BBQ. Well appointed living room, with couch and two lazy boys providing comfortable viewing of the very large flat screen TV - especially after a long day in the sun!...
Mana Kai Maui Resort condo with WiFi & W/D access - near everything
Mana Kai Maui Resort 201COur 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...
Excellent value - OCEAN VIEW - D112
This freshly 754 square foot condo is just steps from the beach, renovated and a corner-unit offering stunning ocean views! Pack up the cooler and head to the beach or lounge by the pool and soak up the serenity that is Kihei Bay Vista.Relaxing, airy and open, this...
Spacious 4th-floor 2bd condo with new furnishings
Papakea D401 is a 2-bedroom, 1-bathroom condo featuring amenities such as a washer/dryer, vaulted ceilings, and air-conditioning. Located on the fourth floor, this condo can comfortably accommodate up to 7 guests with a King bed in the master bedroom bedroom, a Queen...
🏖️Close to A-Bay | Concierge Included | vrKCV
vrKCV - Waikoloa Colony Villas 303, Professionally Managed by Kona Coast VacationsWelcome to Hale A Ka La (House of the Sun), a serene and private town-home located on the 9th hole of the Waikoloa Beach Golf Course. Enjoy the luxury of home comforts and the convenience...
❤️PiH❤️ Ocean Gem Villa ★ Ocean Front ★ Walk to Private Beach Club ★ Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Ocean Gem is a single-level condo with 2 bedrooms located in the prestigious Mauna Lani Point. The home overlooks stunning ocean coastline, the world-renowned Mauna Lani South course and 49 Black Sand Beach. Ocean Gem...
Kaanapali Alii Unit 1662 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean Front________________________________________Welcome to Kaanapali Alii 166, a luxurious two-bedroom oceanfront sixth-floor retreat at Kaanapali Alii! Get ready to experience a vacation like no other as...
9th floor Studio, Sleeps 2, Just 2 mins Walk to Waikiki Beach
Legal Vacation Rental is located at theWaikiki Grand Hotel®134 Kapahulu 922Absolutely awesome unit located just a block from the beach. in fact, you can see the ocean and the beach from the front door! Large Studio apartment with full kitchen and bathroom.Within our...
Top Floor Oceanfront location with great swimming and snorkeling MKM809
Hawaii Tax ID:TA-190-792-2432-01TMK: 390040230093Top floor amazing views in desirable South Kihei! Enjoy long beach walks and the convenience of a coin operated washer and dryer on every floor. Rest and relax in your home away from home. Step out onto your large private...
Enjoy one of the most convenient ground-floor locations at Honua Kai in the highly sought-after interior courtyard of the Konea Tower. Konea 109 offers a spacious 1315 square feet of living space and convenient interior ground floor access to the pools, beach, and BBQs....
Kona Pacific B311 - Quiet, comfortable & walking distance to Town and the beach
Join our friends and family who return year after year to enjoy the Big Island at its finest. We invite you to our home away from home at Kona Pacific Condominiums to enjoy our 829-square-foot, beautifully renovated unit. We are conveniently within walking distance to...
Lokelani C-201 - Oceanfront - 2 lanais! - Complimentary Activities!
Lokelani C-201 in Honokowai is an upgraded direct oceanfront air-conditioned two bedroom / two bath condominium. With spectacular views of the Pacific from both the living room and master bedroom lanai, you will have a front row seat watching breath-taking sunsets and...
Kaanapali Shores: Unit 943 ~ Top Floor & Upgraded with Stunning Ocean Views
Ocean View Penthouse Condo with Upgraded Interior ~ Hosted By Maui Westside● Stunning ocean views from the top-floor penthouse level● No neighbors above you● Spacious 104 sq ft lanai perfect for enjoying coffee or cocktails● Thoughtfully remodeled with granite counters...
(4323/24) 2 Br Hanalei Bay Resort with Amazing Ocean View
Welcome to Hanalei Bay Resort unit 4323/4324. A top floor unit with sweeping views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 2 bedrooms, each with a King size bed along with a loft space with another King size bed and two large...
Ocean Front KUL617 - Upgraded, Top-Floor Unit in Quiet West Maui Location
**2025 Discounted Rates - Book Now! **Imagine waking up in a beautiful, condo on Maui with a stunning ocean view that stretches as far as the eye can see. From unit 617 on the third floor, you can catch a glimpse of the outer islands of Molokai and Lana’i from the...