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.
Ground-floor, oceanfront condo with pool, spacious, private lanai and free wifi
Hale Ono Loa 115Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your home base for exploring paradise with this recently renovated, ground-floor condo! Tucked into an...
Hawaii, Big Island - Mauna Lani, Golf Villas, Unit #O3
Welcome to Golf Villas, a luxurious, quiet, gated condo community in Mauna Lani, Hawaii. - 2-bedroom condo, fully equipped kitchen, and private lanai with golf course views- Master bedroom with king-sized bed and en-suite bathroom- Guest bedroom with two twin beds and...
Oceanfront - Dolphin Retreat - KAYAKS INCLUDED
On the shores of Kealakekua Bay, a Protected Marine Conservation area, is an enchanting, 4 bedroom/3 bath, water front house called the Dolphin Retreat. This open and airy private home has all the amenities one would desire for a tropical vacation. The property is...
Like Sleeping on the Beach! 2bd/1bth, Pool, Split AC
Currently and through October 31, 2025 we are running a 30% off special for guests who rent 7 or more nights!If you dream of sleeping on a tropical beach, a world apart from your everyday life, you will love staying here. Built before setbacks from the water were...
Ocean + mountain view home with WiFi, lanai, onsite pool, & hot tub
Pili Mai 12HOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Are you ready to experience a new Hawaii? Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and...
Lauloa 410 - Top Floor, Direct Ocean Front, Stunning Renovation, Wi-Fi, Split AC
Welcome to Lauloa 410, a stunning top-floor retreat offering unparalleled views of Maalaea Bay, the majestic Haleakala volcano, and the twinkling Kihei lights at night. From your private lanai, take in the soothing sounds of the ocean and the breathtaking scenery that...
Newly remodeled 2-bedroom! Palms at Wailea 2303
Experience paradise in this newly remodeled 2-bedroom, 2-bathroom condo at Palms at Wailea, 2303. Nestled in a private corner of the property, this tropical oasis offers stunning sunset views, lush surroundings, and one of the largest floor plans that Palms at Wailea...
Oceanfront Paradise!
Our condo is the perfect location for a romantic getaway or a family vacation. As soon as you walk through the door, you will know you are in paradise. The oceanfront breeze greets you as you walk through the entrance and into the living room. Not only does the living...
Pool, Jaccuzi, Central AC, Spacious, Steps to Beach, Shops, Restaurants.
This south side maui condo is in a perfect location. You could easily walk to everything. It's next to the beach, restaurants, grocery store, a live music forum, scuba rental, arts and craft shops too. Our beach across the street is great for snorkeling, paddle...
Islander #348, Oceanfront, Walk to Beach, AC, Top Floor, Free Wifi/Parking!
**There will be spalling work on the exterior of the building from June 23 through the end of July or early August.**Oceanfront 3rd (top) floor walk-up studio with beautiful oceanfront, sunrise and moon-rise views on Kauai's Coconut Coast. 375 square ft. of living...
❤️PiH❤️ Hapuna Beachfront Bliss ★ Steps to the beach ★ Amazing Sunsets ★ B29
Welcome to Hapuna Beachfront Bliss at Hapuna Beach Residences brought to you by Paradise in Hawaii Luxury HomesThe shimmery Pacific Ocean beckons you from the moment you wake. Enjoy vibrant sunsets over the ocean each evening. Steps away from your condo is the stunning...
🏖️Great Location | Ocean Front Island Home | Pool | Gated | vrKCV
vrKCV - Vista Oceania at Kona Bay Estates, Professionally Managed by Kona Coast VacationsOceanfront Luxury on Keiki Beach – A Tropical Paradise Awaits YouExperience the ultimate Hawaiian getaway in this luxurious oceanfront home located in the exclusive Kona Bay...
Emmalani Court 414: Fairway View Condo w/ Pool, Spa & Partial Ocean Views
Welcome to Emmalani Court 414, a newly remodeled 2 bedroom 2 bathroom haven that sleeps up to 5 people, where guests can unwind and bask in the beauty of Kauai’s North Shore. Situated just steps away from the open ocean, and with breathtaking views of the island’s...
Discount Rates thru June 30th! Ocean Front Gated Community. 801 Kanaloa
This vacation rental is professionally managed by ResorticaHawaiiPLEASE NOTE: Kanaloa 801 will listed for sale as of July 15, 2025. Guests will not be asked to accommodate showings or inspections during their stay. Please reach out with any questions.Kanaloa #801 at...
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...
Hawaiian Dream with Pool
The Umauma Experience Grand Melemele Home is Your Hawaiian Destination. It is located near Hilo, but far from The Real World. At 3300 sq. ft., 3 beds & 3 bath, it offers plenty of room for everyone to enjoy times together & to have their own space, if needed the...
Pali Ke Kua 104 ... magnificent views of Bali Hai & the blue Pacific
A fabulous ocean vista awaits you at this delightfully furnished condo. Magnificent views of Bali Hai and the blue Pacific are easily enjoyed from the living room as well as the dining area where the panoramic effect is especially dramatic. Located near the edge of a...
Magnificant Ocean Front Condo with New Air Conditioning and Panoramic Views
Kuhio Shores #315. Our light, bright, spacious, and comfortable two bedroom-two bath Poipu Beach oceanfront vacation rental condo sits 40 feet from the ocean's edge. Floor to ceiling glass windows provide unobstructed panoramic ocean views. You can see spectacular...
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...
Stunning Ocean Views, Beachfront Bliss, and Modern Comfort: Ma'alaea Kai 215
Maalaea Kai 215 welcomes you with stunning Pacific Ocean views as you enter! This perfectly located beachfront property boasts over 6 miles of sandy shoreline, ideal for long strolls on the beach. The Tradewinds Market is located down the street, where you can pick up...
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...
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
*Oceanfront*Walk to Waikiki and Ala Moana beaches & shops*Panoramic, unobstructed ocean views*Custom artisan-crafted decor*King bed*Luxurious, pristine linens*Tropical flowers & plants*New beach chairs, wagon, cooler, towels*Gourmet kitchen stocked with coffee, tea,...
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...
Cozy Cute Condo Kihei Maui Vista Complex
Located in sunny South Kihei at Maui Vista Complex enjoy what this 1-bedroom condo has to offer. With a comfy king bed, WiFi, AC, 2 smart TVs, washer & dryer our guests can relax and unwind after a day at the beach. The "Beach Closet" at the entrance has everything you...
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...
Wailea Serenity | 2 Bed, 2 Bath
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. South Maui, with the best weather in the world, is the ideal location for your Island vacation....
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 louver windows in every room that face the water to offer incredible...
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...
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....
Turtle Bay 1 bed with Lanai Renovated Corner Unit 101 - Kuilima Estates East
Panoramic Arnold Palmer golf course views and gorgeous mountains surrounding the Turtle Bay Resort welcome you at the Kuilima Collection | 101 East The set up:1 BEDROOM | Super cozy, plush, pillow-top Queen sized bed with A/C and smart TV. Ample closet space and...
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
Serene garden-view suite at Honua Kai with 2 bedrooms, private lanai, koi pond, and direct pool and beach access-perfect for families seeking space, privacy, and tropical island relaxation.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an...
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...