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.
Oceanfront Condo with A/C, 10 Steps to the Ocean, Ground Floor, Kuhio Shores 112
Kuhio Shores 112 is a quiet, private oceanfront air conditioned condo that is 10 steps from the water’s edge. No need to deal with stairs or elevators; simply walk out the sliding glass door, and enjoy the ocean’s majesty! The first-floor location allows easy access...
Private, Comfortable and Cozy with Distant Ocean and Mountain Views
Boulay Inn is nestled on Kauai’s south side in rural Omao. It is your own secluded home away from home with all the amenities to ensure your comfort. There is a spacious airy living area, a queen sized bed, tiled shower and a verdant yard outside your windows. Your...
Garden Retreat w/Ground Floor Ease - Kiahuna #2115
Kiahuna Plantation #2115: Tropical décor delights in this 690sf rare deluxe ground-floor suite. You and your friends or family can easily access the grounds from your ground-floor balcony and walk to world-famous Poipu Beach which according to "Travel Channel" was once...
Hawaii Life Rentals Presents Puu Poa 309
Welcome to your dream retreat at Puu Poa 309! This impeccably renovated (completed - 3/1/24) two-bed, two-bath condo has AC throughout and two oversized lanais that have one of the greatest views on Kauai's north shore. The condo combines a harmonious blend of modern...
Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper Floor
Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to offer. Get ready to make long-lasting memories while relaxing at this recently updated two-bedroom condo at the beautiful Palms at Wailea. This second...
Luxury Bali Hai Large Villa 2 BR, 2 Ba in Princeville, Kauai; Sleeps 6
This luxury villa is located in the exclusive Kaua’i resort of Bali Hai, in Princeville. This large upper level villa is a 2 bedroom, 2 bath unit that sleeps 6 with a king-size bed in the master bedroom and a luxurious private bathroom with a Jacuzzi tub. The 2nd...
NEW Full Reno 4BD/3B PRINCEVILLE HOME, STEPS FROM QUEEN'S BATH w/ AC & Jacuzzi!
LUXURY PRIVATE 4 bed 3 bath 1760 sf home on a >10K lot w/mtn views in Princeville, a luxury high end community. AC/Jacuzzi/Bikes/Beach Gear included. ***MAJOR RENO NOW DONE!*** ***New photos now up! 5 min. walk to Queen's Bath trailhead (follow safety signs!), ≈15...
❤️PiH❤️ BLUE SUNSET ★ Steps to A-Bay Beach ★ Resort Pool & Waterslide Pass
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Blue Sunset, part of our Hawaiian Luxury Collection. Blue Sunset is in the front row of the Kolea community at the Waikoloa Beach Resort. This gated community is situated on more than 30 acres and boasts...
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
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
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 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...
Kekela Nui Beachfront - Steps to beach + AC!!
*30-night rental*Are you looking for an affordable beachfront property that will fit the whole family and not break the bank? It is a private beachfront property that your family will enjoy and love. The ocean is just steps away. There are no crowds to fight, no public...
New Year's Eve at Hilton Grand Vacation Resort - Kings' Land 12/30/23 - 1/6/24
Hilton Grand Vacation Club - Kings' Land - 2 Bedroom Plus Unit (2KP) - 1269 Sq Ft, Sleeps 6 (second level) - RESERVATION IS FROM SATURDAY to SATURDAYLocated on the Kohala Coast, Kings’ Land is a Hilton Grand Vacations Club resort on 112 ares with world-class amenities...
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...
SUMMER DISCOUNTS! IMMACULATE 1st floor, sleeps 4-5, GORGEOUS, across from beach!
**SUMMER 2024 DISCOUNTS!!! *** 5-star CONDO FOR LESS!!Look no further! Your search for the perfect resort condo for your dream Maui vacation is over! * Military and Kama'aina get a 10% discount! Email owners before booking for a discount *THE UNIT: Perfect for an...
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...
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...
1 Bedroom 2 full baths third floor unit w/wrap around lanai, MOUNTAIN view
In the heart of Maui's famous Kaanapali Beach, steps away from Whaler's Village, with beautiful shopping and restaurants. Beautifully remolded and decorated one bedroom with 2 FULL baths, sleeper sofa and roll-away bed. Wrap around balconies and magnificent views....
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...
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...
Direct Ocean Front Property Wailea Ekahi 42A Remodeled 2024 - 1 Bed 2 Full Bath
Imagine waking to the gentle lull of the trade winds, sunlight streaming through your lanai, and the promise of a perfect day in paradise. Welcome to Unit 42A at Wailea Ekahi Villas, a meticulously remodeled one-bedroom, two-full-bathroom haven where luxury meets...
Spectacular Ocean View At Kona-Isle. Ocean Front Complex-Close to Town & Dining
OCEANFRONT COMPLEX WITH OCEAN VIEW from the lanai and living room at Kona Isle.10% Discount last minute booking summer months.Watch the waves; hear the surf and enjoy the palm trees swaying while sipping your favorite beverage on the lanai or at the waters' edge....
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...