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.
❤️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 brand new, high-end items in 2021, this apartment...
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...
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...
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
From the moment you walk into 4222 and see Bali Hai and Hanalei Bay directly in front of you, you will know you are in paradise. This large one bedroom condo, complete with full size kitchen with washer and dryer, dining room and spacious living room, is centrally...
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 isa 12-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...
LOCATION, LOCATION, LOCATION!!! Hawaiian Paradise Condo w/ Hot Tub, Pool & Beach
LOCATION, LOCATION, LOCATION!! Luxury Ocean Themed Garden Condo with Hot Tub and Pool right across the street from a nice sandy beach for watching the gorgeus Hawaiian sunsets!Experience a blend of modern decor & Hawaiian beach charm in this relaxing condo. Located in...
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...
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...
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...
Waikiki Park Heights 1208 Sun & Beach Fun only 3 minutes away
Waikiki Park Heights 1208 - Ocean-View Serenity Awaits – 30-day MinDiscover the true essence of aloha in Waikiki Park Heights 1208, a charming 1-bedroom condominium located in the heart of Waikiki, providing convenient access to the beaches, shopping, dining, and...
Beautiful home with incredible views, large deck & yard, pool, private hot tub
Waikoloa Luxe LookoutOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your slice of paradise in Waikoloa Village, HI, where breathtaking coastal views and the majestic...
Breathtaking taking ocean views! Kapalua Bay Villa #34B4! Quam Properties
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! 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...
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...
Ocean View Upgraded Top Fl HOKU711 Shaded Lanai see condo comparison chart
**COMPARE MY CONDO TO OTHERS**Hokulani 711-Upgraded 2022 (new beds, headboard, and mattresses, all furniture replaced including the sofa bed with a supreme mattress top, table with optional bench to seat 6, carpet removed and replaced with LVP for a cleaner environment,...
Largest 3BR Villa in Turtle Bay Hawaii, nearest beach access!
Indulge in North Shore Luxury – Closest 3BR Villa to the Beach at Turtle BayWelcome to your ultimate Oahu escape — the only single-story 3-bedroom villa at Turtle Bay Resort, and the closest villa to the beach on the property. This expansive 1,700 sq. ft....
Luxury Kapalua Ridge Villa Featuring Sparkling Ocean, Island and Coastal Views!
Enjoy the 5th Night Free for stays between now and December 15, 2025. *Applies to new reservations only. Property Highlights • Five minute walk from three world-class beaches, including Kapalua® Bay, rated the "Best Beach in the World" by Dr. Beach, and “Best...
Kalo Homes ~ Tropical Makaha Sanctuary
Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We`ve got you covered with all the beach amenities you`ll need to...
Hualalai Palm Villa 130A
One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite opens to a large lanai and...
Maui Parkshore #203 Ocean View, Great Location, Across from Kamaole Beach
Maui Parkshore #203 is a 2 bedroom, 2 bath unit on the second floor with a pool and ocean view, washer and dryer, fully-equipped kitchen, flat-screen TV, DVD player, and free wifi. The master bedroom has a queen bed, ceiling fan, flat-screen TV, alarm clock, and full...
One Hanalei, Luxury Home, walk to the bay! TVNC #1168
One HanaleiPermitted Vacation Rental Property - TVNC#1168Transient vacation rental is located in the tsunami evacuation zoneOne, meaning Sand in Hawaiian, is a family beach house, named after the owner’s mother Sandy and the beautiful sand beaches of Hanalei just...
Kalama Terrace Renovated Retreat, Centrally Located with AC!
Welcome to Kalama Terrace: Your Stylish, Centrally Located Kihei Retreat!Step into island living at Kalama Terrace, Unit P211—an inviting, fully renovated condo in the heart of Kihei. Perfectly situated just a short stroll from the sandy shores of Kamaole Beach and...