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.
Paradise..Million Dollar View From Oceanfront Lanai!
This third floor piece of Paradise has the most fantastic oceanfront view you will ever see. Lauloa means 'long wave' and when you sit on the lanai you will understand how it was named. Look across the bay to Mt. Haleakela, Makenna Point Waialea and Kihei.Dusk from the...
Amazing Direct Ocean Front Condo - Beautiful Sunsets, watch dolphins and whales
Welcome to my Sea Village home on the ocean. This beautiful, 1 bedroom condo is waiting for you to enjoy your island stay. An amazing location with a ground floor entrance, no stairs to climb! Yet, on the other side, the ocean front lanai sits 25 feet above the sea...
BEAUTIFUL Condo with Ocean, Marina, & Sunset Views! Large Lanai!
Ilikai #1239 – 1777 Ala Moana Blvd.Imagine enjoying the amazing marina and ocean views from this beautiful condo at the Ilikai, the iconic destination made famous by Hawaii Five-O. The large lanai spans the length of the condo, so you have spectacular views from both...
Ocean View -KUL209 - West Maui Condo in Quiet Ocean Front Resort—1BR/1B
Unit #209 at Kuleana is truly a vacationer's delight. This condo is larger than most of the one-bedroom and one-bathroom condos on the property, making it comfortable and spacious. The location of the condo is super convenient, with easy access to the beach, a heated...
Oceanview Penthouse, sleeps up to 16 guests!
The Lele Penthouse is a spacious four bedroom two level condominium suite with an open floor plan featuring high vaulted ceilings and large windows throughout allowing an abundance of natural light in. Two additional loft areas equipped with two queen beds in one space...
Ocean View Luxury Vacation Home
This may be the Hawaiian vacation rental of your dreams. Discover Kauai and the North Shore of Kauai overlooking the outer portions of Hanalai Bay, the Bali Hai and the ocean view holes of the Makai golf course. This vacation rental has not only these water, mountain...
Sugar Beach Resort Condo w/ Ocean View, Shared Grill-Swim, Surf, and More
Sugar Beach Resort 231Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Luxury Ko Olina - Spacious 3BR - BT304 Beach Paradise Ocean Views
Luxurious 3-Bedroom Beach Tower Villa | Sleeps 6-8 | Steps from the Lagoon Ko Olina Beach Villas | Kapolei, HawaiiNewly Upgraded (Oct 2024): Washer, dryer, and dishwasher!Villa Features:Spacious 3-bedroom, 2.5-bath villa (1 King, 1 Queen, 2 Twin beds, + 1 sofa...
Kamaole Sands 9-102 - Relaxing Maui Resort
Book with us and come to Maui to explore everything we have to offer!Family friendly ground floor unit with 1 bedroom and 2 bathrooms. Full sized kitchen and large living room to relax in after your busy day under the Maui sun. Air conditioners in the living room and...
Ocean View Lanai and an Easy 5-10 min. walk to beach! Sleeps 4.
Waikiki Park Heights #1705 – 2440 Kuhio Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy the attention to detail in this renovated one-bedroom condo with ocean views and central A/C! With 488 sqft (plus 60 sqft balcony/lanai with table...
Sugar Beach Resort Condo w/ Free WiFi, Ocean View-Near Everything
Sugar Beach Resort 526Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Sunset Kahili 101; Two Bedroom & Two Bath Ocean View Condo on Kauai
Sunset Kahili 101 is a remarkable two bedroom condo located in the heart of Kauai's premier resort destination, the stunning south shore of Poipu. Nestled in close proximity to world-class beaches, this nearly oceanfront property offers an unforgettable vacation...
Beautiful 2Br 2Ba Puamana, Ocean and Mountain View, AC, Pool
Indulge in a vacation like no other at Puamana #14B, and let the enchanting beauty of Kauai be your backdrop for an unforgettable Hawaiian escape. This two-story, 2BR/2BA condo with mini split AC, WiFi and a chef's kitchen has tranquil ocean, mountain, and golf course...
Zen Oasis Waikiki - Oceanfront Penthouse
Wake up to endless ocean horizons! This Zen-inspired penthouse marries sleek design with soothing décor for a truly restorative stay.Private lanai overlooking Waikiki BeachKing-size bed & fast Wi-Fi for work-cationsSteps to surf, dining and nightlifeAs Superhosts we...
Poipu Palms 204, Ocean Front, One Step Up to the Front Door
POIPU PALMS 204 AT KOLOA KAI VACATION RENTALSOceanfront Bliss with Panoramic ViewsWelcome to Poipu Palms 204, where your Hawaiian dream vacation begins! Nestled on a stunning oceanfront bluff, this charming two-bedroom, two-bath condo offers breathtaking views of the...
Summer Reduced! Gorgeous Ocean and Pool View Villa O503!
Ocean Tower villa 503 has a gorgeous view over the pool to the ocean! This villa offers Hawaiian touches and high-end furnishings throughout. This villa is great for families or couples looking to get away! Photographs are of the actual villa.- 1,575 sq ft of living...
Pili Mai Condo 1C, Spacious, Great for Families, Mountain View
Pili Mai is one of Poipu's newest complexes with a great location and spacious living! You will not be disappointed as you step into this 3 bedroom condo and discover the great features such as travertine, granite, wood flooring, plantation shutters and extra touches...
❤️PiH❤️ SWEET ESCAPE★ Free Private Beach Club ★ Free Hilton Resort Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sweet Escape Villa, a part of our Hawaiian Luxury Collection. Sweet Escape Villa at KaMilo is a wonderful new single level 3 bedroom home. Sweet Escape Villa provides a perfect setting for your Hawaii getaway...
Oceanfront West Maui Condo w/Shared Pool, WiFi, Loft, Desk Workspace, and Lanai
Mahina Surf 228Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This home is just a few yards from the ocean with windows in every room that face the water to offer incredible views...
Maui's #1 KAANAPALI BEACH, TOP FLOOR, 3 BEDS L200
Maui Eldorado Resort L200, top floor ocean view spacious condo. Centrally located in the heart of Kaanapali, short walk to Whaler's Village shops, restaurant and walk to Kaanapali Beach. This spacious 1700 sq ft Maui Eldorado bright condo affords ocean view from this...
Front Row Seat in this Luxury Condo, Ocean, Yacht Harbor, Fireworks, Restaurants
Check out our calendar for all the fun-filled dates available! Choose the 'You Found Paradise' luxury condo for a stay that's not just a vacation – it's an adventure! Why settle for the ordinary when you can embrace the extraordinary in our newly revamped condo?Step...
Maui Kamaole H212: Ocean View 2 Bedroom loft condo within walking distance t
PROPERTY PROJECT:The upper pool will be closed from November 11th through November 21st 2025 to re-coat the upper pool deck. You will not get enough of this ocean-view second-floor condo. The extra window in the living room allows more sunlight to come in and creates a...
Best Ocean View 202 won't disappoint!
WELCOME TO PARADISE...Welcome to Polynesian Shores 202.Hosting couples, professionals, friends or families is our specialty. Newly updated, this condo comfortably sleeps six guest.The upstairs bedroom loft offers a master style suite with a king bed and full bathroom....
Cozy Condo Across the Street from the Ocean!
The locationOur condo is in the perfect location – stroll down the private tropical grounds and into Kam II – one of the best beaches in Kihei! Kam II is a 2-acre beach park that features a lifeguard station, picnic tables, grills & restrooms, and is one of the best...
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,...
Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East
Kuilima Collection | 101 EastPanoramic Golf Course Views | Renovated 1-Bedroom Corner UnitEscape to the lush North Shore of Oʻahu and experience the best of Turtle Bay living at Kuilima Collection | 101 East. Nestled along the 17th hole of the famed Arnold Palmer Golf...
Top Floor Cozy Condo Nestled Among Tropical Kailua Kona Treetops
[June 2020: Due to pandemic concerns, we shut down operations April 1 - June 9; the island has "opened up" again, and we are again comfortable hosting Kona guests! Our cleaning person Dianna, best on the big island, is there to make sure our unit is extra clean!]...
Romantic 1 BR Condo with King Tempurpedic
Relax, enjoy the gentle breeze, take a deep breath and enjoy the birds, flowers and scents of Maui that surround you.Our quiet location is surrounded by the Wailea Old Blue Golf Course & adjacent to the Wailea Tennis Club & Wailea Town Center; minutes away from the most...
Ocean Front Top Floor Condo/Free WiFi & Parking/Pool/Jacuzzi/Grill/Beach Equipmt
Did you ever dream of a vacation where there is nothing between you and the ocean but a few waving coconut palms? This is the place to be!Wake up to 180 degrees of unobstructed ocean front view from your own lanai, watch the surfers on the waves, migrating whales (in...
KBM Resorts | FREE CAR | Honua Kai Konea | Rare Ground Floor 2-Bedroom Condo with 14 ft Ceilings! HKK-112
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Oceanfront condo with shared pool and stunning views - near shopping and dining
Hololani B404Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself and your loved ones to a relaxing island getaway with this oceanview Maui condo at Hololani. You'll enjoy...
A beautiful Turtle Bay condo on the golf course - Kuilima Estates East
Welcome to paradise, enjoy this North Shore Turtle Bay condo. Brand new state of the art air conditioner in master bedroom, living room, and loft. Private master bedroom with A/C and king sized bed and bathroom. Upstairs find two queen size beds in a loft and fan. This...
Ideal Getaway Near the Beach & Town W/ Two Kitchens, Wraparound Deck & Views
Jubilee By The SeaOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take a break from it all and spoil the whole family with an unforgettable getaway to this home away from home mere...
🏖️Easy Walk to Town | Ocean Front | AC & WIFI | vrKCV
vrKCV - Kona Reef A6, Professionally Managed by Kona Coast VacationsRelax and Unwind in This Beautifully Renovated Oceanfront Condo!Welcome to this beautifully furnished 1-bedroom, 1-bathroom ground-floor unit at Kona Reef, where tropical décor, ocean views, and modern...
Close to the Beautiful Kailua Beach-A/C's-Full Kitchen-Covered Patio-Pet ok
For questions, to verify availability dates or to check the availability of other furnished rentals we manage, please contact the owner. This large 700 square foot rental unit called the 'Coconut Corner' is one of the nicest rentals you will find on the Windward side of...
Beautiful beaches for swimming and sunsets! Kamaole Sands 3-207
Condo, 1 Bedroom + Convertible bed(s), 2 Baths, (Sleeps 2-4)Custom remodel on second floor of desirable BUILDING 3, one bedroom, two full bathrooms condominium with beautiful view from the spacious lanai. Air conditioning in both living room and bedroom providing air...
Wailea Elua Village 2401 - 1 Bedroom Ocean View Condo
Completely renovated in 2019, Wailea Elua 2401 is a stunning vacation condo that features a large private wrap-around lanai with breathtaking ocean views. This beautifully designed rental offers a serene indoor/outdoor living space, perfect for enjoying Maui\'s...
Maui With a View - 13th Tee!!
6 GUESTS PER RENTAL MAXIMUMLOCATION, LOCATION, LOCATIONWelcome to the FRONT ROW of the Kaanapali Plantation! It's all about location, and this condo is located in the FRONT ROW of the Royal Kaanapali Golf course at the 13th tee, providing an unobstructed view of the...
Gorgeous Penthouse w/ AC, Steps from the Beach!
Newly updated unit w/ AC. Historic plantation-era Hawaiian style right by the ocean. Very romantic and relaxed place, great for your next Ohana getaway, for honeymooners, and anyone who wants to enjoy the Garden Island of Kauai. You will find just about everything that...
Enjoy ocean views at lovely 2bd condo
Step inside Papakea J202, a 2-bedroom, 2-bathroom condo that offers AC and flat-screen TVs in every room. This condo can accommodate 6 guests. The master bedroom features a comfortable king-size bed with wall-to-wall windows, flat screen TV, and an ensuite bathroom with...
Tropical garden view Wailea condo
Grand Champions 8 is a 2 bedroom, 2 bathroom condo featuring amenities such as a private lanai, air-conditioning and a washer/dryer. Located on the 3rd floor, this condo can comfortably accommodate up to 6 guests with a King-size bed in the master bedroom, a Queen-size...
Plantation Hale Suites H7, AC, Walk to town, Near Beaches, Comp Wifi
NOTE: Rates Automatically Discounted from September 15 through December 2025 due to construction repairs on various H-building decks during this time. We apologize for the inconvenience. Work Hours: Monday–Friday, 9:00 AM–5:00 PM.Welcome to Plantation Hale Suites...
❤️PiH❤️ OCEAN POINT ★ Walk to Beach Club ★ Steps From Ocean ★ Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Ocean Point is an elegant and newly remodeled upper-level condo with 2 bedrooms located in the prestigious Mauna Lani Point. The home overlooks world-renowned Mauna Lani South course, a large water feature and Hualalai...
BEAUTIFUL GARDEN & GOLF COURSE VIEW 2 BEDROOM CONDO
You've never seen such a relaxing and comfortable vacation rental as this Keauhou Surf & Racquet condo. Located with a golf course view on 16 ocean front acres, you'll never want to go home! Ground floor, no stairs with nearby reserved parking. Surf and Racquet is a...
Tropical Oasis
Enjoy Hawaiian living in this spacious 2 bedroom, 2 bathroom, 2nd floor condo with an ocean view. Large lanai overlooks the eighth fairway of the Kona Country Club. This unit does NOT have air conditioning. Each room has a ceiling fan and there are 4 floor fans. This...
Paradise is Calling...So is the Sun, Sand, Sea&Tropical Breezes-Kihei, Maui B406
THIS CONDO IS NOT ON THE MINATOYA/SHORT TERM RENTAL LIST.FEEL FREE TO BOOK LONG RANGE VACATION AS WE WILL BE HERE.We would like to share our spacious Paradise home with you. It is comfortable, fully furnished and it is fun!! Enjoy your breakfasts and dinners on the...
Princeville Condo w/ Private Sauna ~ 2 Mi to Beach
Experience the perfect blend of oceanfront adventure, outdoor exploration, and tranquil relaxation when you stay at this 2-bedroom, 2-bath vacation rental. With a fully stocked kitchen, welcoming interior, and a central location surrounded by the area's top attractions,...
The Perfect Spot for Your Dream Vacation!
**Nohonani 402 – Your Oceanfront Paradise**Welcome to Nohonani 402, a stunning 2-bedroom, 1.5-bath unit on the fourth floor, featuring vaulted ceilings and breathtaking ocean views. Enjoy the panoramic vistas from the kitchen, dining areas, living room, and master...
Paradise retreat! Plunge Pool, Hot Tub, AC & Water Gears!
Tropical Paradise in Princeville’s most desirable neighborhood tucked between golf course and the ocean, across the Queens Bath. Two-level house with 3 bedrooms, den and nook can accommodate 11 people. Bali style furniture and all memory form mattresses. equipped...
Spectacular Ocean Front location! Everything a Beach vacation should be! AC!!!
Newly installed Central Air-conditioning! Ocean views along with Mountain views right on the beach! In Kihei, you can not be any closer to the beach! This building is maintained like a resort! From the soft golf grass turf to the beautiful pool you feel like you are in...