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.
Wailea Ekahi 24B - Modern Garden Retreat w/ Lanai, Split AC & Stylish Renovation
Nestled on the ground floor, Wailea Ekahi 24B is a beautifully remodeled one-bedroom, two-bath condo featuring a sleek, modern design and effortless indoor-outdoor living. With elegant finishes throughout, including quartz countertops and stainless-steel appliances,...
Incredible Highrise Views! | Heart of Town
Enjoy breathtaking ocean views in this recently completely remodeled hotel condo, perfectly located next to Ala Moana Mall and across from Ala Moana Beach Park. Ideal for up to 4 guests, the condo features two double beds, a functional kitchenette, and a private lanai....
Location Location! Ekahi 32C! Designer Remodel 2bdrm $400 Remaining SpringSummer
Wailea Ekahi Unit 32C is a beautiful vacation condominium in the prestigious area of Wailea, known as the 'sunny side' of Maui. It is located on the greenbelt, just across from one of Ekahi Village's four private pools and a very short stroll to the beach and pool...
ICC 22 Beautiful 2BD Cottage Perfect Tropical Vacation
International Colony Club 22 Beautifully Designed 2Bedroom Cottage For the Perfect Tropical Vacation. Private, Next to the Pool, and Close to the Beach FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*:...
The Best Ocean View Studio Condo at the Royal Kahana Oceanfront Resort
We finished a complete remodel of the kitchen and the living room in December 2021.Stop!! You found it!! The best studio condo at the Royal Kahana based on the view, condition and price. If you've stayed in other studio's at the Royal Kahana it's time you stayed in the...
❤️PiH❤️DOLPHIN HALE★Close to Pool and Fitness★Bikes Beach Gear★ Full 3 Bath
Brought to you by Paradise in Hawaii Luxury Homes. What makes a Paradise in Hawaii home stand above the rest? Our homes have adult and kid bikes, tons of beach gear, well equipped kitchens, smart TVs and comfy beds and Fast WiFi with great coverage included!! Welcome to...
50 steps away from Maui's best beach, furnished with luxury details
Welcome to your perfect getaway in Maui! This exquisite 2-bedroom, 2-bathroom apartment, nestled on the 2nd floor of Pacific Shores complex, elevator-accessible building, offers 745 sqft of living space. Furnished with high-end furnishings, this apartment comes with 3...
Beautiful 2-BR Villa at Four Seasons Hualalai
**Please note that the Chairman's Club Event takes place each year at Four Seasons Resort at Hualalai from approx December 2 - December 7th. . This event will result in limited access to resort amenities. Details at end of listing!. **Enjoy the quintessential Hawaiian...
Maui's Ultimate Luxury Estate – Ka'anapali Beachfront Paradise
Boasting an epic location on one of only 6 beachfront residential parcels in all of Kaanapali, this breathtaking 9BR/9.5BA estate represents the pinnacle of Maui vacationing. Guests will enjoy the space and solitude of this luxurious private home nestled steps from...
Kukuiula Cottage #27 By Parrish Kauai
This handsomely designed and decorated Kauai cottage offers the details of early plantation days yet with the modern conveniences of central air conditioning, as well as everything else one needs to indulge themselves on a luxury Kauai vacation. Enjoy the lush garden...
Ocean front 1 Bedroom condo in desired F building in Papakea Resort in Maui HI
No resort fees!! Papakea is an unique property. Instead of a high rise it is a set of buildings only 4 levels high. There are three sets of buildings that front the ocean and we are located in the middle section--the perfect location for reaching either of the two...
Luxury Poolside Villa | Stunning Ocean View, Lanai
Summary:D210 | TA-019-101-6960-01Enjoy tropical views and elevated comfort at Villa D210, part of the Poolside Villas at Poipu Kai. This spacious 3-bedroom retreat features an open layout, designer furnishings, central A/C, and a fully equipped gourmet kitchen. Dine...
Jaw Dropping Ocean Views from Second Story, 2 Bedroom Unit 2D
As you wake up in the morning, take in the beautiful view with the cool ocean breeze. Sit on the balcony with a refreshing drink as you appreciate the magical Maui sunsets. Vaulted ceilings. Granite countertops. Spacious bathrooms. Open concept. Large glass sliding...
NEW LISTING Kailua-Kona 3-bedroom, 2-bath single-family home Ocean & Sunset View
Immerse yourself in the enchanting allure of Kailua-Kona at our 3-bedroom, 2-bath single-family haven, offering you panoramic views of the endless ocean horizon. Every detail has been meticulously attended to, including newly installed split AC units in every room, new...
"Hale Opaka" | Beach Access, 6 BR, 2 Kitchens, A/C
Vrbo Premiere Host new rental: Experience the ultimate Hawaiian getaway in this spacious oceanfront estate just steps from the beach. This unique property combines upper and lower units connected by external stairs for maximum space, privacy, and breathtaking ocean...
Maui Sunset B102 - Aloha Tai 2, Beachfront Resort Condo, Ground floor, 1B/2BA, S
Summary:Condo in Beautiful Oceanfront Resort - ground floor tastefully-updated with all new furniture (April 2022) 1-Bedroom 2-bath with King Bed, Queen Sleeper & Twin Murphy bed in LR. Family Friendly, sleeps up to 5, Full Kitchen, AC, Washer/Dryer in-suite, Free...
Airy Oceanfront Kailua-Kona Gem w/ Community Pool
Your paradise dreams are now a reality in this Kailua-Kona condo, surrounded by acres of tropical landscaping, ocean views, and sitting steps to the beach! Gather the family or a small crew for an escape to the Big Island in this 2-bedroom, 2-bath vacation rental with...
Fabulous Oceanfront Two Bedroom w/Huge Lanai & Central A/C!
SPECTACULAR ABSOLUTE OCEANFRONT 2 Bedroom 2 Bathroom condo in Kailua-Kona!! The spacious lanai starts and ends your day in paradise. Enjoy your morning coffee and relax to the sound of the surf while watching whales (in season), spinner dolphins, outriggers, and the...
Beachfront Studio in North Shore - Upper Unit
Beachfront to Sunset Beach, this studio boasts breathtaking views of the Pacific Ocean and its world-famous sunsets. Sip your morning coffee or enjoy a glass of wine at dusk on the private balcony or the sandy beach.This second floor studio is a gem located in a rare...
Beautiful Beach Villa in Oceanfront Resort
Your ultimate paradise vacation awaits you at the Ko Olina Beach Villas Resort, Oahu's premier Oceanfront resort. Stay in this beautiful two bedroom/two bath luxury suite and enjoy sunset views from the expansive lanai. This spectacular beachfront resort features a huge...
PUAKO BEACH: an eclectic, TRANQUIL and HISTORIC oceanfront community.
We have a two story residential home, located across the street from the turquoise clear waters of the Pacific ocean. Our guest apartment is on the ground floor with its own private entrance through a garden atmosphere into a large screened in porch with plants, table...
Honua Kai Ground Floor # Luana 1B - 3 bed / 3 bath villa - front side location
This is ground floor unit Luana 1B at Honua Kai. After the devastating Lahaina fires, Maui has officially re-opened and is welcoming visitors back. Please book your stay and help support the Maui recovery. Currently, new bookings in my units through VRBO come with my...
SPECIAL DEALS! One of a Kind! THE Best Ocean Views with Bali Hai & Hanalei Bay
Welcome to Hanalei Bay Resort 4222 – a truly one-of-a-kind getaway with iconic panoramic views of Bali Hai and Hanalei Bay. From the moment you step inside, you’ll know you’ve arrived in paradise.This spacious one-bedroom retreat features a remodeled kitchen with...
Cozy 3bd/3b Beach Retreat, Sleeps 10, AC, WiFi, Fam-Friendly in fantastic Koloa
Escape to paradise in this relaxing 3 bed/3 bath retreat at the Pili Mai condos located on the Kiahuna golf course. This unit can sleep up to 10 guests, relax in its plush interiors with a king bed, 1 queen bed and a cozy bunk room (1 queen, 1 full, 2 twin beds),...
Modern, 29th Fl, View, Legal
Prepare to fall in love! The location of this privately owned, snug 212 sqft studio at the Hawaiian Monarch Hotel is simply perfect, with all the Waikiki attractions within easy walking distance. You'll be delighted to know that the beach is just a short 10-minute...
Across from BEACH! Remodeled in 2023! Split A/C!
1 Bedroom, 1 Bath, Sleeps 2 **This property is hotel zoned, and not being affected by the recent proposed legislation**Experience a tropical paradise with our recently remodeled convenient ground floor, remote work friendly, 1-bedroom, 1-bath Kihei Akahi condo in the...
Maui El Dorado Kaanapali Beach Studio- G204, Maui El Dorado Kaanapali Beach Resort
New Property!!Located within the Maui El Dorado, this condo is surrounded by palm trees with a peek-a-boo view of the ocean. This is a 10-minute walk from the Whalers Village and restaurants and 1 mile from Black Rock Beach. There's a 3-night minimum stay.The complex is...
5 Star Location! Downtown Hawaiian Paradise Condo w/ Hot Tub, Pool & Beach
You just found the best-priced condo in the absolute heart of Kailua-Kona. The prime downtown location and amenities are the highlight of this condo. Imagine waking up, walking across the street, and being on a beautiful sandy beach watching sea turtles or catching...
Holua Kai #27: Luxury Oceanfront Villa w/Private and Resort Pools & Spas
Holua Kai #27 by Gather is a single-story, plantation-style home specifically designed to seamlessly connect indoor and outdoor spaces thanks to its large open floor plan. Its 2,372 square foot layout features 3 bedrooms and 3.5 bathrooms with comfortable air...
Kona Townhome w/ Lanai & Resort Amenities!
Experience paradise from this 3-bedroom, 2.5-bathroom vacation rental townhome in Kailua Kona where you have the chance to create life-long memories with your loved ones. Sip coffee from the balcony each morning while taking in ocean views, spend your days using the...
Your Maui home-30 day minimum rental
Spacious 1Bedroom, 2Bath -- Rent from Super Hosts! Big View, Spacious Layout, Quality Furnishings, Two Private Lanais. New Air Conditioners, Remodeled throughout including updated kitchen and bathrooms, California King Bed.Perfect place for honeymooners!Enjoy an ocean...
Spectacular ocean and beach view 2 BR condo, steps from the ocean!
E Komo Mai! Welcome to 603 Kamaole Beach Royale, our home away from home.We enjoy a spectacular view of the beach, the ocean, and the neighbour islands from the sixth floor of Kamaole Beach Royale, a seven-story building situated right across the street from Kamaole...
Kaia Villa, at Turtle Bay - Modern North Shore Oahu Retreat w/Lanai & Golf Views
Debuting October 2025. Kaia Villa offers a newly renovated stay on Oahu's famous North Shore. Set within Turtle Bay Resort , This property has been thoughtfully transformed into a stylish island retreat designed for comfort and relaxation.Every detail has been curated...
Ocean View, Double Lanai and a Quick Walk to the Beach
Condo Details: **This is a NON-Smoking Unit AND a non-smoking property. All forms of smoking or vaping is prohibited in the units, lanais as well as common areas including the parking lot. ****This is a PET free unit. **Our beautiful ocean view unit is situated in upper...
VIP Maui - Amazing Ocean Views at the Royal Kahana
Vincson's Island Paradise (VIP) located at the Royal Kahana Resort by Outrigger in beautiful West Maui, is a newly remodeled studio that boasts all the amenities you need to make this your home away from home. Centrally located in quiet picturesque Kahana, we are 4...
Wailea Ekahi Village 23C - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you a relaxing, island-inspired retreat. Nestled within 34 acres of lush tropical landscaping, 23C is a ground-floor...
Wailea Elua Village 1604 - 2 Bedroom Oceanfront Condo
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty that Wailea Elua 1604 offers. Evenings offer gorgeous sunsets framed by swaying coconut palms, perfect for a relaxing...
Luxurious Kolea Villa, Private Lanai w/ Gorgeous Ocean Views, Beach Club
Summary:Hawaiian beachside luxury awaits at Kolea 9H, a stunning 2-bedroom villa at Kolea featuring a private lanai and partial ocean views. Located only a few steps from Waikoloa Beach, guests also have access to the Kolea Beach Club and a shared swimming pool....
Maui Resort Rentals: Luana Garden Villas 2D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious brand-new 3Bedroom/3Bath residence is conveniently set within Enclave One of the Luana Garden Villas. Villa 2D's north-facing orientation offers a Shady respite from West Maui's legendary endless sun and its designation withing our "Elevated" collection...
STEPS TO THE SAND !!! <br>TVNC # 5088
This beautiful beachfront Hanalei Bay home is located steps from the sand on Kauai's majestic North Shore. Enjoy the best views of the pier, surf, mountains, and sunsets over Mt. Makana the north shore has to offer. This modern updated cottage has 2 bedrooms and 1bath....
Lovely Remodeled 2BR, 2BA Condo, across from Kamaole beaches, Sleeps 4-6.
Welcome to our beautiful fully remodeled 2 bedroom, 2 bath luxury condo located in the stunning and lush Maui Kamaole complex located at the south end of Kihei, and close to Wailea. Maui Kamaole is located right across the street from the renowned Kamaole beaches and...
Breathtaking taking ocean views! Kapalua Bay Villa #34B4! Quam Properties
Nestled in the heart of Maui's prestigious Kapalua Resort, Kapalua Bay Villa 34B4 offers the perfect blend of tranquility, luxury, and convenience. Surrounded by lush tropical landscapes and perched above the sparkling Pacific, this one-bedroom, one-bathroom villa...
Luxe Beachfront Tropical Paradise
30+ 5 Star "Awesome" "Beautiful" "Bliss" Reviews and Counting! Please plan ahead as our calendar fills up quickly.THE AMBIENCEIf thoughts of azure oceans, romantic getaways and sunrise mornings are just some of the peaceful images that make you happy, then this is the...
Spectacular Ocean View At Kona-Isle. Ocean Front Complex-Close to Town & Dining
Vast ocean view from Lanai and Living Room. Imagine watching the waves, hearing the surf, palm trees swaying and songbirds singing while sipping freshly brewed Kona coffee on the Lanai. Ahhh, look over the pristine gardens and let the colorful island birds entertain as...
Best Views at Honua Kai - Penthouse Suite with Private Lanai & Grill-Honua Kai K1025
This condo is zoned hotel and is a legally compliant vacation rental in Maui CountyLuxurious Penthouse Escape with Sweeping Ocean Views, Private Lanai, and Resort-Style AmenitiesAloha e komo mai – Welcome to your luxurious Maui retreat, where the aloha spirit and the...
Poipu Modern Island House w/AC & Pool/Gym Access
DISCOUNT DUE TO CANCELLATION: LOW PRICE FOR Feb 25-Mar 25: $495/Night BOOK NOW!!!!!!!!!!!!!!Discover beautiful Kauai from this spacious 3 bedroom 3 bath 2000 sf vacation home in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood...
Newley remodeled and beautifully furnished downtown Kailua-Kona condo.
Located on the ground floor at Kona Plaza Condominiums, Unit 107 is newly remodeled & just steps away from downtown Kailua Historic Village & the Kailua Pier. Decorated with a taste of Hawaii that will set the mood to kick start your Hawaiian adventures. Fully furnished...
Ocean View - 2 Bedroom - Marriott's Waiohai Beach Club - 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...
WOW! WHALER's BEST!! EXQUISITE REMODEL!! 11th Floor VIEWS! - 3 BEDS -SLEEPS 5!!!
Whaler unit 1170 is a beautifully remodeled 1-bedroom, 2-bath condo at The Whaler condominium resort. Unit 1170 offers breathtaking panoramic views from the 11th floor of the Pacific Ocean, Molokai Island, Black Rock Cove, the Maui Mountains, and the golf course. This...
South Maui Beach Front Condo
Your family will be close to everything when you stay at this centrally-located place. Walking distance to shopping and restaurants. Only 20 minutes from the Airport, 15 minutes to Maalaea ocean center and easy access to Piilani highway for Haleakala crater.Registration...