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.
Kahana Manor #603 - Vacation West Maui - Oceanview Near Beaches and Restaurants
Rest peacefully on our incredibly comfortable beds and wake up refreshed, ready to embark on another incredible day in Maui!This charming condo features:2 bedrooms and 2 bathrooms, accommodating up to 6 guestsSituated in an amazing location in Northwest Maui, with close...
Pili Mai 15F - 2 bedroom/2 bath, ground floor
PILI MAI 15F AT KOLOA KAI VACATION RENTALSModern Luxury in the Heart of PoipuDiscover the perfect blend of island charm and contemporary comfort at Pili Mai 15F, a spacious two-bedroom, two-and-a-half-bathroom condo overlooking the lush Kiahuna Golf Course. With central...
WORLD CLASS Special May Disc 13-18 & 25 to 6-1. Full AC, 2 Suites 550
Spectacular views from high on top of the cliffs of Princeville. This top-level condominium is terraced at the edge of the bluff, commanding unobstructed blue Pacific Ocean views, including Hanalei Bay. Easterly trade winds caress the property with refreshing tropical...
Violet Sunset 2802: Newly Renovated Oceanfront Suite
Violet Sunset 2802 is an absolutely lovely, newly-renovated two-bedroom oceanfront suite is a breath of fresh air nestled up against the magnificent Kona coast! Its laid-back island charm combined with all the comforts and conveniences of home provide the perfect...
Newly Renovated High-end 1 bedroom, 2 bathroom Wailea Condo close to beach
The Palms at Wailea #1804 has been completely renovated, be among the first to enjoy this brand-new high-end renovation in Wailea in which every room has been updated. This bright, spacious condo has a refreshing beach personality, 1000+ sq. ft., and 2 large lanais for...
The Islands at Mauna Lani | D2
The Islands at Mauna Lani D2 is newly renovated in tasteful, modern decor, and has a regal feel from the moment you enter the double-wide frosted glass front doors. This two-bedroom two and a half bathroom vacation rental comfortably sleeps six guests and offers plenty...
House close to beach, North Shore, Oahu
Located on the countryside of Oahu between the ocean & the mountains, you will be in the perfect spot to experience what Oahu has to offer.Close to world famous North Shore, Turtle Bay Resort, popular surf breaks, snorkeling spots, sea turtles, & much more!Only 2 min....
Maui Dream Place at Maui Kamaole G-209, Direct Ocean View, 2 Story Modern Condo
Maui Dream Place is our vacation home rental property in Maui, Hawaii. This two story condo has plenty of space for your family, plus hotel-style amenities which include access to two swimming pools, hot tubs and tennis courts. In our opinion, our condo has the best...
Kuilima Condo on the 18th Hole - 5 Minutes to Beach
Aloha! Come enjoy your Tropical Hawaiian Vacation in our beautiful, clean, and relaxing one bedroom and two bath condo with all the conveniences of home. Our spacious condo is the perfect blend of tropical seclusion amidst all the amenities offered by a world-class...
Kalia'i Marriott, Beach Club weeks are available in 2025
This listing is for a studio or hotel type room suite. A studio comes with a Murphy wall bed with a real mattress and a kitchenette. A hotel room comes with a king bed and a seating area that turns into an additional single bed. Marriotts owners calendar does not sync...
Ocean Front Renovated 2 BR/BA Luxury Condo w/ A/C . 2nd Floor Unobstructed View
Royal Mauian #212 LUXURY OCEANFRONT condominium on the SECOND floor (Unit #212) is 30 feet from the ocean at the CENTER of Royal Mauian Resort allowing you to enjoy the 180 degree panoramic UNOBSTRUCTED CENTRE ocean view of the Pacific Ocean. A few steps from the Royal...
Waterman’s Paradise Beach Toys Kayak/SUP & A/C! TVR 4238
Mana Kauai Island Vacations Presents the Kalihiwai Beach House.Kayaks, boogie boards, surfboards, and stand-up paddleboards are yours to be enjoyed every day of your vacation. No need to pay the high rental fees.Kalihiwai Beach is one of the secret gems on the north...
BEAUTIFULLY REMODELED OCEANFRONT ONE BEDROOM 2 BATH CONDOMINIUM
Oceanfront Paradise in Kona Alii – Beautifully Remodeled 1-Bedroom CondoEnjoy breathtaking, unobstructed ocean views from this fully remodeled 1-bedroom, 2-bathroom condo in the heart of Kailua-Kona. Located in the sought-after Kona Alii Condominiums, this upscale...
Ka'anapali Vista: 4BR Home with Pool, AC, BBQ & Outdoor Shower
This is a legally permitted vacation rental according to the County of Maui ordinances.Heavenly Ocean Views with Your Private Saltwater Pool & Lanai at KAANAPALI VISTAAloha e komo mai—welcome to your Maui paradise, where the spirit of aloha embraces you in every...
NEW Luxury OCEAN & SUNSET View with Huge Wrap Around Lanai and GOLF DISCOUNTS
Newly Listed Luxurious XL Ground Floor Hawaiian Condo with Stunning Sunset Views, overlooking the 3rd hole of the Waikoloa Beach Nine at Kings Golf Course. Enjoy huge golf discounts as Guests of Gold Members. Escape to your dream vacation at our beautifully appointed...
2 Bed/2 Bath Hawaiian Vacation - Walking Distance to Beaches, Shopping & Golf
Welcome to Island Therapy! Located just 20 minutes north of the Kona (KOA) airport, this 2 bedroom, 2 bathroom villa offers all the amenities for a wonderful Hawaiian vacation. Stop at Costco on the way from the airport and pick up everything that you need and prepare...
Very Private location. Amazing View. The Cliffs 6302
The Cliffs Resort charges a $15 parking fee per vehicle per night. We have included the charge for one vehicle in our nightly rate, so you don’t have to pay it at check-in.From the moment you enter Cliffs 6302 and see the breathtaking ocean front view, you will feel...
Fully Renovated Oceanfront with Air Cond. Ground Floor Unit with Spacious Lanai!
Come enjoy our fully renovated condo - we've meticulously renovated the kitchen, bedroom, bathroom, and the tile floors! And, we have AIR CONDITIONING! We are one of a few units in Kuhio Shores (and in Poipu) that has installed A/C! This makes our condo perfect...
Amazing OceanView, Best, Front Row, Retractable Awning for Lanai! Relax, Enjoy!
NEW:Why Rent this condo at Maui Kamaole, Kihei, HI, USA?You are ready for an escape to a beautiful location and relax at a home base that allows you access to ask Maui had to offer.CONSIDER THE FANTASTIC LOCATION in Maui, HI, USA, THE SPECTACULAR VIEW, OWNERS'...
Oceanfront Penthouse Villa - walk to the beach and gorgeous sunset views!
Aloha! E Komo Mai (Welcome) to our beautiful luxury Beach Villa in Ko Olina on the island of Oahu and conveniently located just 25 minutes from Honolulu! We would love to have you come stay with us!!Our fully equipped luxury 15th-floor penthouse is located in the Ocean...
Wavecrest’s Only Ground Floor, 2 Bedroom
Rare find - Wavecrest’s only ground floor, 2 bedroom 2 unobstructed ocean view lanais unit on the unique island of Molokai. Private washer and dryer in the unit are an added bonus. Wavecrest is on the East end of Molokai which is the most tropical on the island. All...
Hale Ohana Hau'oli - Charming Kukui'ula Villa with Geometric Pool + Spa!
From the striking stone-pillared entry to the enchanting backyard banyan tree, this delightful Kukui'ula villa radiates an irresistible island-style ambience. Indoors and out, Hale Ohana Hau'oli teems with beautifully curated details: tasteful contemporary furnishings...
The Grand Islander, a Hilton Grand Vacations Club
Discover the beauty of Honolulu from this adorable 1-bedroom resort. The rooms feature 1 king beds, perfect for a serene night's sleep. Enjoy the convenience of a full bathroom with showers and a cozy living room with a sofa bed. With amenities like WiFi, AC, and a...
OCEANFRONT BR/1BA with BREATHTAKING VIEWS! nParadise Found!
WATCH WHALES JUMP OUT OF THE WATER FROM OUR PRIVATE LANAI. Whale Season Dec-Apr. Located on beautiful Kahana Beach, our remarkable property offers captivating views of Molokai and Lanai. Immerse yourself in the perfect harmony of tranquility and convenience, with...
Center of Waikiki - 1 Bedroom 3 Queen Size Beds
THOUGHTFULLY CURATED BY OWNER/ARCHITECT TO CREATE A STRONG SENSE OF BELONGING.YOUR ULTIMATE HAWAIIAN RETREAT IN THE HEART OF WAIKIKI31st-floor corner unit in the Island Colony Aqua hotel building. You are in the CENTER of Waikiki, surrounded by shops and shopping...
4 Bedroom/ 3 Bathroom Private Home
This home includes ocean views, a rooftop deck, and a heated pool. Enjoy breathtaking views of the majestic lava-formed Ko'olau mountain range and only steps to the # 1 rated beach In the world (2015), Waimanalo Beach, famous for the filming of Magnum PI, Baywatch,...
Mauna Lani Fairways 603: Luxe 2BR Home w/ Modern Comforts, Jacuzzi & Lanai Views
Escape to comfort at Mauna Lani Fairways 603 by Gather, an elegant retreat in Hawaii’s lush Mauna Lani Resort, where each detail enhances relaxation and luxury. With recent updates, including fresh paint, modern furnishings, new appliances, and captivating artwork,...
Come & stay with us at the beautiful & peaceful Bird's Nest
The Bird's Nest is located in a peaceful neighborhood that is surrounded by lush greenery and bird songs can be heard throughout the day & tree frogs at night. The house sits high above the ground which makes it feel as if you are staying in a tree house. The road in...
Recently Fully Renovated-Oceanfront, Top floor, Million Dollar View, Sleeps - 2
Our newly renovated condo #310, is on the top floor. Enjoy the 3rd floor with NO noise above you, directly over beautiful Wailua beach. "Fall asleep to the sounds of the crashing waves" The condo is located on the quieter end of the building, away from Main Street. From...
Spectacular View, Direct Oceanfront Kona, Top Floor
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGEOur lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the...
DIRECT OCEAN FRONT 2Bd/2Bath Whaler on Kaanapali Beach
Discover our beautifully spacious 2 bedroom, 2 bath Direct Ocean Front condo at The Whaler #1102. This particular home is a rare and sought after condominium, located on the north corner of Tower I. It’s 11th floor location offers an unobstructed northern view from...
Pipeline Beach*Studio Large*AC*wifi*Free Pk*Steps To White Sand Beach*30nite min
The studio has a TV with cable, internet connection, air conditioner, a full kitchen with an oven and stove, a refrigerator, microwave, toaster, blender, coffee maker, plates, pans, and other eating utensils. The studio is very clean, very comfortable with soft sheets....
Beautiful Condo Across the Street from Beach w/ Ocean View and Great Snorkeling!
Kahalu'u Beach Park is a prime spot for snorkeling, surfing and relaxing on the sandy beach. The beach is literally right walk across the street. Enjoy amazing ocean views from your private lanai, a spectacular infinity pool, hot tub and bbq area. This meticulous 2...
2BR 2BA end unit Ke Nani Kai Molokai, HI Unit 151 - Ocean View, Remodeled
Beautifully renovated ground level 2 BR/2Bath end unit on Island of Molokai, HI with partial ocean views and wrap around Lanai. Unit 151. Tucked away in the back corner of the complex provides more privacy than most other units at KNK.Wi-Fi &cable TV, new flat screen...
LUXURY F205 - VIEWS INCLUDES GOLF DISCOUNTn 2 Bdrm 2.5 Bath 5 MIN walk to BEACH
This luxurious and completely remodeled 2nd Floor unit offers GOLFERS STAYING IN THIS UNIT GREAT DISCOUNTS FOR GOLFING with our Gold Membership @ WAIKOLOA BEACH, KINGS & LAKES COURSES. ALMOST ½ OFF!!Our complex has a large HEATED, SALINE outdoor lap POOL and 2 Hot...
3BR/3BA Villa: Central A/C! Short Walk To Beach!
Welcome to BlueTideVillas! This unit not only boasts among the BEST reviews in all of Kauai but is also newly upgraded to enhance your stay from April, 2024, onwards.Nestled in the heart of Poipu, this VERY spacious (1830+ square feet) villa is a newly remodeled and...
OCEAN FRONT 2bd/rm Townhome New Remodel Ocean and Sunset Views AC Pickleball!
Aloha, we would love to have you as our guests! It is a pleasure to know you are interested in our Ocean front 2 bedroom/ 2 bath townhouse. We have had a tremendous amount of positive reviews, but decided to update the property to provide an even better guest...
Kumulani B4 Best Ocean Views in Complex, Amenity Pkg Optional.
Surround yourself with the luxury, elegance, and all the amenities of two of the world's finest resorts - The Mauna Kea and The Westin Hapuna Beach Resorts.This 2 BR 2 bath second floor luxury condominium is located in The Uplands of the Mauna Kea Resort and is accessed...
Polo Beach Club | 407
Polo Beach Club 407 is a premier oceanfront vacation rental located in the upscale resort area of Wailea. This two-bedroom, two-bathroom condo offers guests a luxurious and comfortable stay with sweeping ocean views and direct beach access out front. If looking for the...
Updated End-Unit Oasis, 3 Bd + Loft & 2 Ba, Pool, Walk to Beach, AC Coming Soon
Welcome to our private tropical oasis! This newly updated 1,478 sq. ft. end-unit offers the perfect retreat. Surrounded by lush tropical plants, you’ll enjoy privacy and tranquility, with no neighbors above or below you. The home features massive wood beams and large...
Ocean, Sunset, Mountain & Celestial Views
Enjoy ocean, mountain, sunset and star scape views from nearly every room in this family friendly, three bedroom and two bathroom house in Waikoloa Village, Hawaii. The house includes everything you'll need on your paradise escape including a fully equipped kitchen,...
Gorgeous Kapalua Oceanfront with Stunning Views
Spectacular OCEANFRONT Kapalua Bay Villa, impeccably maintained and beautifully furnished. As you enter, you are welcomed by panoramic views of the glistening Pacific and Molokai. This lovely 1600+ sq. ft., ground floor unit has 2 spacious bedrooms, 3 baths, an inviting...
Escape to Paradise at Beautiful Maui Kam In South Maui!
Our Hearts go out to the people, families, friends and loved ones of West Maui. Maui Travelers, please consider giving extra patronage to the small businesses, restaurants and services that are open throughout Maui that employ so many who are affected with personal...
5 Bed 3 Bath Home in Poipu Kai
Hale Aouli is a beautiful newly renovated five-bedroom and three-bathroom custom home located in beautiful Lanai Villas in the Poipu Kai Resort. From the home, you will find walking paths to Poipu's finest beaches, restaurants, tennis courts, pool,...
Swim with the turtles and watch the whales! S-l-o-w down and R E L A X.
Directly overlooking the ocean, a newly remodelled, bright condo in a heritage building, set amidst lush green foliage. Enjoy the large lanai with panoramic views. Safe swimming all year round, your choice of nearby beaches, close to everything that you'll need in Hilo....
"Sea Gem" a Oceanfront Condo at Lae Nani 515
"Sea Gem" A Oceanfront Ground Floor 2 Bedroom | 2 Bathroom at Lae NaniPanoramic views at Lae Nani of Wailua Bay await in this sunny condo located along the island's east shore. Situated just steps from the shoreline, the sights and sounds of the waves are palpable from...
Seaview Maui – Family Vacation Home in Upcountry Maui
Maui County Rental permit - STPH 2014/0004TA-097-868-8000-01 / GE-097-868-8000-01TMK-270031100000Welcome to Seaview! This is a unique family style vacation home, offering space for up to ten family members or friends to vacation together, with considerable privacy....
Waterfront condo with shared pools, private beach, balcony, W/D, and AC
Casa De Emdeko A317Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched on the top floor, this stunning 2-bedroom, 2-bathroom condo in Kailua-Kona offers sweeping ocean and...
Stunning ocean view! 2/2 in the heart of Wailea
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning...
Wai'ula'ula 330 - Upcountry Oceanview Residence
This discerning, upcountry, oceanview residence offers a great room with sliding glass pocket doors that invite indoor/outdoor island living; a chefs' kitchen outfitted with slab granite countertops and premium stainless steel appliances (including a wine refrigerator);...