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.
Wai'ula'ula 328 - Luxe Oceanview Residence
This luxe, ‘upcountry’, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with Wolf and Sub-Zero appliances, including a double oven and wine refrigerator, dual master suites and a...
North Shore Sweet Spot w/ King Bed Overlooking Lush Valley
Welcome to Hale Moi, your tropical escape on Kauai's stunning North Shore! Our charming Princeville condo offers comfort, authentic island experience, and lush greenery. Enjoy breathtaking views from your private lanai, modern amenities, easy access to Hideaways Beach...
FREE Parking1BR Penthouse Condo @Palms +near Beach
【Basic Info】This is a private 1 Bedroom 1 bathroom condominium unit in Waikiki!!You can enjoy your stay by only yourself, friend or partner. The condominium is located in Waikiki.It's closed to many famous shopping centers like Royal Hawaiian Center, T Galleria!You...
Relaxing Ocean View Room - Steps to Waikiki Beach
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
Oceanfront Oasis at Ilikai Hotel | Private Lanai
One of Waikiki's few oceanfront vacation rentals, the iconic Ilikai Building in Waikiki, Honolulu offers incredible views of the ocean, bay and marina with floor-to-ceiling glass windows and a spacious private lanai. Incudes a full gourmet kitchen, three beds for ample...
Kaanapali Maui Eldorado A106 Partial Ocean 1 BD
- Full kitchen includes refrigerator, stove/oven, microwave, dishwasher, cookware, tableware- 2 KING beds- Queen sofa sleeper in living room- Partial ocean view- Lanai dining - Bathroom with walk-in tile shower- 1200 sqft / 111 sqm- Maximum 4 persons including children...
🏖️Beautiful Mountain View | Concierge Included | Spacious | vrKCV
vrKCV - Vista Waikoloa D204, Professionally Managed by Kona Coast VacationsWelcome to Waikoloa Vista D204, a comfortably appointed condo ideal for couples or families. This 2-bedroom, 2.5-bathroom second-floor unit is nestled in the heart of Waikoloa Beach Resort and...
![[New]Ocean + Sunset Views | Parking | Kitchen | WD](https://media.vrbo.com/lodging/111000000/110080000/110077900/110077886/55bd22a9.jpg?impolicy=ccrop&w=1000&h=666&q=medium)
[New]Ocean + Sunset Views | Parking | Kitchen | WD
Welcome to your Hawaiian escape! This 12th floor corner unit boasts peekaboo ocean views and stunning sunsets from your spacious lanai. Enjoy your morning coffee and relax in the open and bright living area. Unwind at the rooftop pool with panoramic views of the mtns,...
Discovery Bay Waikiki, 2BR 2BA, close to beach, free parking, washer/dryer, cable & streaming TV!
Enjoy comfort and convenience in this updated, fully furnished 2-bedroom, 2-bathroom condo with city views from the 9th floor of Discovery Bay. The full kitchen and spacious layout make it perfect for families, friends, business travelers, or anyone needing extra room...
Luxury Poipu Kai 3 Bedroom Villa with Pool and Tennis!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Enjoy tropical foliage and pool views with an exceptional level of luxury at this 1800 square foot villa. This stunning 3 bedroom, 3 bathroom condo offers all of the comforts of home...
3 HGVC Hawaiian Village Beachfront Resort and Spa!
Enjoy the glamour of this stylish, upscale place. Set among 22 acres of pristine Waikiki beachspace, Hilton Grand Vacations at Hilton Hawaiian Village provides visitors with spectacular amenities and an unrivaled position in the heart of paradise. Guests are treated to...
Marriott Ko Olina Beach Club 2BR Villa - July 4th or Thanksgiving on the Beach!
A beautiful Hawaiian Resort awaits your family and friends to celebrate 4th of July week or Thanksgiving Week. Your charming 2 bedroom villa invites relaxation and restoration with two lanais offering island, mountain, and/or partial ocean views replete with the...
Palms at Wailea Villa 805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- 2nd bedroom with 1 queen bed- Queen sofa bed in living area-...
Direct Ocean Front 1 BDRM 2Ba Whaler #601
Whaler 601 is a privately owned, beautiful, 1 bedroom, 2 bath, DIRECT ocean front, corner unit, with a wraparound lanai on the North tower on the 6th floor of the Whaler resort. Many listings say 'ocean front' but in reality, are common ocean views. The attached photos...
Kaanapali Alii | 183
Kaanapali Alii 183 is a luxurious oceanfront vacation rental nestled in the heart of Maui's renowned beach destination of Kaanapali. This spacious 1,800 square foot condo offers breathtaking views of the Pacific Ocean, the islands of Lanai and Molokai, and the pristine...
NEW LISTING: Open Condo with Warm Wood Accents
Welcome to Koa Resort 2I — a beautifully appointed 2-bedroom, 2-bathroom condo that comfortably accommodates up to 6 guests. The spacious living room features a queen sleeper sofa for additional sleeping space. Please note that the second bedroom is a loft, offering...
Lani One’ā: A Handcrafted Island Sanctuary with Seaside Community & Aloha Spirit
This charming, elevated home in Pahoa, Hawaii, blends modern comfort with island charm. Painted in soft green hues that complement the lush tropical surroundings, this rental is perfect for a relaxing escape.
Kanaloa at Kona Ocean View 2 Bedroom
- Condos located on 1st or 3rd floors- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Private balcony with wet bar- Master bedroom with 1 king bed or 1 queen bed and private bathroom with...
New Listing! Private Maui escape with Island charm
Welcome to Alaeloa 35 – Your Private Maui Getaway! Tucked within the peaceful, oceanfront enclave of Alaeloa in Napili, Alaeloa 35 is a charming 3-bedroom, 2-bath freestanding cottage that effortlessly blends island comfort with timeless Hawaiian charm. Surrounded by...
Waikiki Getaway! Pool, Near Honolulu Museum of Art, Parking!
You’ll feel right at home at this lovely boutique property in Waikiki! Enjoy grab-and-go breakfast in the comfort of your accommodations, take a dip in the heated outdoor pool, or make a little something in your own kitchenette and relax on your private lanai. An...
Christmas Week 2024 Westin Kaanapali Ocean Resort Villa - Full Resort Access!!
Christmas week: 12/20/2026- 12/27/2026Westin Kaanapali Ocean Resort Villas - stunning property.Garden/Island View 2 Bedroom Lock-off UnitWith views of the West Maui Mountains and the beautiful resort grounds, guests can enjoy Westin's unrivaled luxurious Two Bedroom...
Westin Ka'anapali Ocean Resort Villas 1 Bedroom Villa Ocean View
The Westin Ka'anapali Ocean Resort Villas - whale watching, snorkeling, sailing, windsurfing and scuba diving just steps away, there are plenty of activities at our Maui beachfront resort near Lahaina - comes with Westin touches keeping in harmony with the Hawaiian...
30 Day Rental in Waikiki with Parking!
Welcome to Fairway Villa, your ideal retreat in the heart of Waikiki! This studio, available for a minimum 30-day stay, is perfect for remote workers, traveling nurses, or anyone needing a longer-term stay in Waikiki. The studio features a comfortable Queen-sized bed, a...
Hilton Hawaiian Village Lagoon Tower 2BR 2BA sleeps 6--Ocean View
Consider this condo your home away from home while you visit Honolulu. Lagoon Tower offers 2 bedrooms and 2 bathrooms, ensuring a comfortable stay for guests. With amenities like a hair dryer, heating, WiFi, a washing machine, an iron, a fitness room, and AC, your needs...
Lahaina Condo Studio • 2 Beds • 1 Bathroom
Begin your Maui journey at The Westin Kāʻanapali Ocean Resort Villas. Our dedicated guest services team helps plan amazing island trips, such as volcano visits or waterfall treks. Your pre-arranged activity passes await you upon check-in. Unwind in your private villa...
Waikiki Beach Walk Resort 2BR/2BA
Located on nearly eight acres of new Waikiki pleasures. If you're looking for a resort that packs a ton of nearby fun, be among the first to reserve your spot at the new Club Wyndham at Waikiki Beach Walk®, part of Outrigger's huge Waikiki Beach Walk project. This...
Snowbird-friendly home near the beach with patio, grill, outdoor dining area
Hale Olena Ohana - 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located just 26 blocks from the ocean, this snowbird-friendly home offers the perfect...
Royal Kahana Maui 415 Ocean View 1 Bedroom
- 4th floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in pebble shower with grab bar- Queen sofa bed in living area- Central Air Conditioning-...
Oceanview Suite and Cottage
We are a 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.This rental is composed of 1 Suite and 1 Cottage.We have a brand new split system AC and heating in every room and...
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802n
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront...
Westin Nanea Ocean Villas Resort & Spa, Hot Tub!
A state of relaxation and repose - firsthand at The Westin Nanea Ocean Villas! Set on twenty-six acres of lush, tropical land and infused with a variety of Hawaiian design elements, The Westin Nanea Ocean Villas blends a top-notch vacation experience with the authentic...
Alii Park Place#N-202: Gorgeous Remodeled Top Floor 3 Bedroom unit with AC
Alii Park Place is one of the premier developments on Alii Drive. Tinguely Development group created this complex wanting to offer true quality living. It's clearly apparent this reigns supreme as you walk into the space. Unit#N-202 is beautifully furnished, and offers...
Oahu Dream! 3 Amazing Units, Pool, Minutes to Waikiki Aquarium, Waikiki Beach
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Private Napili Nest Near Beach
Tucked away, yet within minutes of Napili Bay, Kapalua resorts, golf, hiking and restaurants, Napili Nest is a private, remodeled and well-appointed end-unit studio with an A/C, a balcony, peek-a-boo ocean/garden view and thoughtful guest amenities. Located in a quiet,...
Wyndham Ka Eo Kai 2BR/2BA w/pool
Club Wyndham Ka Eo Kai perfectly captures the ambiance of the "Garden Island" while offering a variety of nearby recreational options including family fun adventures, horseback riding and golf. Set amidst a lush tropical garden, the resort offers easy access to top...
Newly remodeled 2bd condo with ocean breeze
Mahina Surf 205 is sure to impress! Stunning tropical hues greet you the moment you walk in. New and modern furnishings, Maui-inspired designs, and artwork throughout the condo transport you to the perfect beachy abode where you can instantly unwind and enjoy the beauty...
Island Paradise home 5 min from the beach
Your family will be close to everything when you stay at this centrally-located place. Our Island Paradise home is just a short 5-minute walk to the beach, offering the perfect blend of convenience and relaxation. This fully furnished midterm rental offers 4 bedrooms, 2...
Royal Sea Cliff Kona 303 Garden View 1BD 1BA
- Ground floor condo near pools and BBQ grills- Covered lanai is 154 square feet/14 square meters- Tile floor throughout unit- Updated kitchen featuring granite counters and stainless-steel appliances- Bedroom with 1 queen bed- Queen sofa bed in the living room-...
Queen Bed | Outrigger Waikiki | Shopping & Dining in Central Waikiki! Gym, Pool!
Make this comfortable and convenient property your next Waikiki adventure! Relax by the pool, enjoy dinner with family at one of three on-site restaurants, or grab a pastry and morning coffee at the coffeehouse. And best yet, the sun, sand, and surf of Waikiki Beach are...
Marriott Ko Olina Beach Club - On The Beach- Family Friendly - Mountain View
Come experience Hawaii at this premium level Marriott Resort in Oahu. With luxurious amenities and great family entertainment, your family won't want to leave.This property has everything you need for a tropical vacation. There is a lagoon style family pool with...
Fairways Villas at Waikoloa E4 Golf View 2 Bedroom
- Front office is located at the Kings' Shops, 69-250 Waikoloa Beach Dr., Suite B-13. Office is open daily 9 am - 5 pm. - Kitchen features cooktop and oven, refrigerator, microwave, dishwasher, coffeemaker, toaster, rice cooker, blender, cookware and tableware - Master...
KBM Resorts | FREE CAR | Hale Honu At Montage Kapalua Bay, Sleeps 10! 3-Bedroom Condo with Daily Housekeeping, Spa!
Luxurious ocean view 3-bedroom, 3.5-bath Grand Residence at Montage Kapalua Bay, gourmet kitchen, spacious lanais, and convenient beach and pool access.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and...
Discovery Bay 1 Bedroom Deluxe Ocean View, Near the Beach!
Experience island living with comfort and style in this 37th-floor ocean-view condo at Discovery Bay! This inviting 1-bedroom unit features a queen bed, sleek vinyl flooring, refreshed furnishings, and a modern design perfect for a relaxing getaway or extended...
Picturesque views of the ocean and Diamond Head
Mesmerizing panoramic views of Diamond Head, the blue Pacific Ocean, the moon and stars! This spacious corner condo is as close as you can get to the sand without being on the beach. Step back in time for this rare opportunity to stay for a while in the home of a...
New Listing! Charming studio with central A/C
Kaanapali Shores 736 is a charming Studio condo with central air conditioning, comfortably accommodating up to 4 guests. Perched on the seventh floor, this unit features an open-concept design, creating a peaceful island retreat. After a day of adventure, relax on the...
Maluhia at Wainani - New Poipu Home with Private Pool & AC
Maluhia at Wainani is a fresh and stylish modern villa with all the amenities one desires while on vacation. Tucked back away in the quiet part of Poipu, but still perfectly located near the beach, this home is the idea vacation spot. Centrally located in Poipu Beach...
Kaanapali Alii | 192
Kaanapali Alii 192 is a stunning vacation rental located in the prestigious resort town of Kaanapali on the western coastline of Maui. This luxurious one-bedroom (plus den), two-bathroom condominium spans approximately 1,500 square feet, offering ample space and comfort...
Westin Ka'anapali--Spacious Studio with full kitchen-- full resort access
On beach with outdoor pool, near Whalers VillageGuests of this beach resort will appreciate convenient onsite amenities such as a hot tub and a fitness center. Air-conditioned accommodations at this resort offer safes and coffee/tea makers. Rooms open to balconies....
Christmas in Hawaii!!! 2 BR & 2 BA Ocean View in Ko Olina on the island of Oahu
Marriott Ko Olina Beach Club is surrounded by clear blue waters and a picturesque lagoon. Just steps from the ocean on the island of Oahu. Soak up the sun by one of our three outdoor pools, work out in our state-o-the-art fitness center. During your stay enjoy...
A Luxury Vacation Home: KGV 12V3
Welcome to your dream vacation rental! Kapalua Golf Villa 12 V3, is nestled in the beautiful area of Kapalua, offering guests a truly stunning view of the lush green fairways of the golf course and the sparkling blue waters of the Hawaiian ocean beyond.This top floor...