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! 1 BR Beach Condo Steps Away from the Beach and Downtown
Enjoy the world's best sunsets and beaches.E Komo Mai to the Kona Billfisher, where true aloha spirit awaits your arrival! Situated on the southern edge of the village of Kailua Kona, on the island of Hawaii, the Kona Billfisher is walking distance to beaches, shops,...
Marriott Maui Ocean Club - Christmas Week - 1 bedroom, 2 bath
This studio unit is the middle property of the three Westin Kaanapali Ocean Resort properties on one of the highest rated beaches in the world, with snorkeling, kayaking and safe swimming right out your door. This property can only be reserved for a Sunday to Sunday...
Kaanapali Alii 244
Welcome to Kaanapali Alii Unit 244, a luxury vacation rental nestled in the heart of Maui's exclusive Kaanapali Alii Resort. This stunning 1,513 sq. ft. corner unit offers breathtaking views of Kaanapali Beach, the majestic West Maui Mountains, and lush tropical...
Poolside Peace Meets Island Play—Your Kona Getaway Starts Here l 4 Rooms
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
2-Bedroom Ocean View, Perfect Location in Waikiki!
Modern Luxury with Stunning Views - Flexible 2-Bedroom Layout!Renovated in June 2024, this upgraded condo seamlessly blends modern luxury with practicality, creating a stylish and comfortable retreat. Featuring new kitchen cabinets with quartz countertops, luxury vinyl...
Fun Family Private Retreat with lighted Sports Court and Pool
More than just a stay, it's an experience for the whole family, both young and old. Our family retreat has over 3000sq' under roof, overlooking incredible ocean and coastline views. Sitting on 6 private acres of old lava fields with a beautiful pool, lighted...
NEW!!! Island Sophistication, Beachfront Serenity w/ Hot Tub, Firepit and A/C
Wake up to the sound of waves crashing at this luxurious North Shore retreat, perfectly tucked away along a quiet stretch of sandy, swimmable beach. Just steps from the shoreline, this home offers the ideal balance of refined relaxation and island adventure. Mokuleia is...
KR 203 Stunning Direct Ocean View 1BD Amazing Kahana Maui Location
Kahana Reef 203 NEW LISTING Bright Blue Direct Ocean Views from this Kahana 1Bedroom Condo West Maui 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...
Greenery Mountain View Waikiki Seaside Monarch Paradise Hotel Room
Beachfront Location: Waikiki Seaside Monarch Paradise Hotel Room Greenery Mountain View in Honolulu offers a private beach area and beachfront access. Guests can relax by the rooftop swimming pool and enjoy stunning lake views.Comfortable Amenities: The apartment...
Oceanfront Bliss - Luxury on The Bluff
Experience this beautifully renovated suite. A perfect blend of tranquility, luxury, and natural island beauty. A rare offering of panoramic, unobstructed views of the Pacific. Wake up to breathtaking sunrises and enjoy nature’s finest moments—Humpback Whales...
Waikiki 2BR Condo, walk to Beach, free parking
Escape to your next Hawaii getaway at this large 2-bedroom,1-bathroom condo in Honolulu,Hawaii! The property is ideal for families or friends traveling together and accommodates up to 6 guests comfortably. Offering stunning ocean views throughout the condo and a lovely...
Kai Hale-Anini Beachfront Paradise
Oceanfront luxury meets Old Hawai‘i charm at Kai Hale, your private beachfront escape on magical Anini Beach, voted best snorkeling beach in Hawaii. Just steps from the sand, this peaceful retreat features panoramic ocean views, open-air living with floor-to-ceiling...
Magic Skies Ocean View Turtle Room
Turtle lovers, you will feel right at home with queen size bed with panoramic ocean views. It features an ensuite w granite counter tops, double sinks & marbled tile walk-in shower w rain shower head, regular head & hand-held. The room also has a mini frig, coffee &...
New listing - Sea Village 3304 Ocean Views
Welcome to Sea Village 3304 – Your Oceanfront Oasis on the Kona Coast!Experience the ultimate Hawaiian escape at Sea Village 3304, a beautifully appointed oceanfront property offering stunning views and unparalleled relaxation. This 1-bedroom, 1-bathroom condo is...
Wailea Point | 2301 - 2 Bedroom Ocean View Condo - 30+ Night Luxury Stays
Wailea Point is the ultimate in privacy and elegance for those seeking stays of 30 nights or longer. For shorter stays, please select from one of our other beautiful Wailea resort properties. The finest development in the finest neighborhood on the finest Hawaiian...
Golf Villas Gold Ocean View 1 Bedroom at The Kapalua Villas Maui, Outdoor Pool
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Newly renovated Hualalai Palm Villa -15th hole - 2 Golf Carts
This two-story Hualalai Palm Villa is newly renovated with every modern amenity. There are three bedrooms each with king size beds and 3 full baths. All bedrooms have flat screen TVs Direct TV, and Apple TV. Located on Waiulu Street at the world renowned Hualalai...
Lagoon View In the Ilikai Hotel, Perfect Location!
1 Bedroom Lagoon View on the 8th Floor of the Ilikai Hotel! Enjoy the Hawaiian sunshine from your lanai overlooking the peaceful lagoon and the Pacific Ocean. This piece of paradise featuring a full, open kitchen, two twin beds, and free long distance and wifi is the...
Maui Getaway: Spacious 2BR Ocean View Lockoff at Westin North
Bring the whole family or travel group together in this spacious 2-Bedroom Lockoff Ocean View Villa at The Westin Kāʻanapali Ocean Resort Villas North. With about 1,230 square feet of space, this flexible villa setup comfortably sleeps up to eight guests.The lockoff...
Aston Maui Kaanapali Villas #267 - Premium one bedroom loft, with two bathrooms,
Aston Maui Kaanapali Villas #267 - Premium one bedroom loft, with two bathrooms, and sleeps four guests.Stunning, Premier, one-bedroom condo at the Maui Ka'anapali Villas. This beautifully remodeled condo is the perfet spot to relax during your Maui getaway. The bedroom...
Hale Ola: 5BR Portlock Luxury Home with Saltwater Pool
In Honolulu’s exclusive Portlock neighborhood, Hale Ola welcomes you with sweeping ocean views, the gentle sound of cascading waterfalls flowing into koi ponds, and a backdrop of Diamond Head and the mountains. This single-level estate blends refined interiors with...
Papio House With Ocean Views and Beautiful Sunrises
Dreaming of a peaceful Hawai‘i escape with breathtaking ocean views?Welcome to your private island retreat in the lush Puna District. This home offers the perfect blend of comfort and adventure, perched near dramatic black lava cliffs, surrounded by swaying palms, and...
The Lodge at Kukui‘ula - Bungalow 12
This three-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i offer luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling...
Wailea Ekahi Village 12B - Studio Ocean View Condo
Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designers may want to take notes! This gorgeous ocean view studio is ideal for couples looking for a cozy retreat or solo travelers looking for the perfect...
Kailua Bay Resort#2-306: Top Floor Corner 2 bedroom condo with Ocean Views
Top-Floor Gem in the Heart of Kona – Kailua Bay Resort 2-306Welcome to your Hawaiian getaway at Kailua Bay Resort, Unit 2-306 — a stunning top-floor 2-bedroom, 2-bathroom condo that has been beautifully remodeled for modern island living. Located in the heart of...
Kukui Cabin with Private Bath
Welcome to Kukui Cabin, your cozy retreat nestled in a serene setting. Perfect for couples, friends, or solo travelers, our cabin features two twin beds that can be combined into one queen bed. The cabin is conveniently located near a Common House that boasts a...
Monthly- Chateau Waikiki 3513 2 Bedroom Ocean / Diamond Head
PANORAMIC OCEAN / Diamond Head VIEWS, 10 Minute Walk to Beach, 2 Bed Room, Furnished. No smoking condo. 2 Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 2 Month Minimum / contact Agent.Spectacular ocean, volcano, mountain and town views from...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, Top Floor Deluxe Ocean and West Maui Mountain Views + BBQ on Balcony!
This spectacular 10th-floor 4BR/5BA 'penthouse' offering combines a breathtaking Deluxe Oceanview Suite with a neighboring corner Mountain View Suite, to provide over 2,000 sq. ft. of elegant interior living space and unforgettable panoramic views.Unquestionably one of...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Extra Large Lanai | 3 Units, 5 Bedrooms | HK ML-1928
** 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...
2 Private Oceanfront Homes on Tropical 2 Acres!
Experience the magic of this breathtaking oceanfront estate. Watch dolphins, whales, and cruise ships sail by and feel the cooling TradewindsLocated on the Hamakua Coast, this is more than a place to stay, it's a lifetime experience not to be missed!Consisting of two...
Spacious Island Retreat • AC • WD • Parking • WiFi
Welcome to your large island getaway in sunny Kapolei! This 7-bedroom, 5-bathroom home offers two complete living levels, ocean views from the upstairs lanai, and all the amenities you need for a comfortable extended stay. With 2 kitchens, and plenty of indoor and...
Kapalua Ridge Villas Gold Partial Ocean 2 Bedroom
Ridge Villas Gold Partial Ocean View 2 Bedroom 2 Bath- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1...
City View Studio with Kitchenette - Waikīkī Grand #517
Castle at Waikīkī Grand #517 - Large glass windows invite the beautiful natural Hawaiian sunshine and showcase the surrounding city of Waikīkī. The living and sleeping area is furnished with comfortable chairs, a flat screen TV, and Wi-Fi to help you relax after a...
Aloha Condos, Napili Bay Resort, Condo 218, Beach View
Napili Bay Resort Condo 218 is a serene, well-equipped unit perfect for relaxation. Guests love the quiet, jungle-like lanai, comfy bed, and stocked kitchen. Proximity to the beach, beach chairs, boogie boards, and a welcome gift basket are highlights. The private,...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Premium Bay Villa | 2 Units, 3 Bedrooms | KBV ML-1604
** 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...
Sunset & Ocean View 2BR Condo in Waikoloa Village with pool and fitness room
A sanctuary with panoramic views in Waikoloa Village. The Lanai offers front row seat to the golf course, sunset over the Kohala Coast, Kohala Mountain and Haleakala on Maui! The condo has two ensuite bedrooms and baths, King beds, walk-in closets and a half bath. Roomy...
Kiahuna Plantation Resort 112 Royal Garden Vw 1B
Relax in this ground floor garden-view condo, where cottage-style warmth meets island tranquility. Located near Kauai’s most beloved beach, it’s a welcoming space to unwind after a day of exploring. Unit 112 Royal Garden View 1 Bedroom 1 Bath• Fully equipped...
MK404 - Sleep at the Ocean and Watch Sunsets 3-Bed Suite
Welcome to your dream escape at Maui Kai, an unforgettable oceanfront gem nestled on the golden shores of Ka‘anapali Beach in West Maui. This rare 1-bedroom suite is the perfect retreat for ocean lovers looking for comfort, charm, unbeatable views, and a strong...
New Listing! Direct Ocean Views, Private Lanai
Welcome to Maui Parkshore 310 – Your Oceanfront Paradise! Experience the best of Maui living at Maui Parkshore 310, a beautifully updated 2-bedroom, 2-bathroom oceanfront condo perfectly situated just steps from the golden sands of Kamaole Beach Park III. Located on...
HKI 110 Ocean Views from this 1BD West Maui Condo Oceanfront Pool Amazing Location
Hale Kai 110 NEW LISTING Convenient West Maui Location with Ocean Views from the Ground Floor Lanai, Oceanfront Pool and BBQ's! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal),...
Kamaole Sands 10-110: 1 Br Ocean View near Kamaole Beach Park III
This ground floor S. Maui Vacation condominium conveniently located across the street from Kamaole Beach Park III gives you all the indoor comfort of your condo with the added beauty right outside your lanai door. The fountain view right outside your porch is sure to...
Waterfront Kaunakakai Condo in Molokai Shores
Imagine being surrounded by palm trees, a lush yard, and a community pool, all while enjoying views of the ocean. All of this and more can be yours when you stay at this modern 1-bedroom, 1-bathroom vacation rental in Kaunakakai. With modern, coastal furnishings and a...
Modern 3BR w/ Ocean Views | Steps to Kamaole III
Summary:Completely reimagined in 2025, this modern 3-bedroom condo blends designer style with island comfort—just steps from Kamaole III Beach. Enjoy ocean views from your lanai, a fully equipped kitchen, and luxe touches throughout. Sleeps 8 with 2 king rooms, a bunk...
Cozy Studio at WorldMark Kihei – Maui Getaway for Two
Enjoy a simple and comfortable Maui escape in this studio suite at WorldMark Kihei. Perfect for couples or solo travelers, this suite offers everything you need for a relaxing stay in paradise.Inside the studio, you’ll find a queen Murphy bed that tucks away for extra...
Maui Sunset Vacation Rentals B305
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. Third floor middle of the building views of tropical gardens and the ocean beyond. Quiet location features large...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢’𝐬 Beachfront Fun at KoOlina Club Resort+Amenities.2BR
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝟐-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at one of...
Westin Princeville Villas
Essence of HawaiiThis refreshing resort lies along a lush cliff on the north shore of Kaua'i and blends into the inspiring beauty surrounding it. Resting two hundred feet above the Pacific Ocean, The Westin Princeville boasts plunge pools provide quiet relaxation while...
Royal Kahana Maui 904 Ocean View Studio
- 9th floor condo with balcony- Updated kitchen with granite counters, breakfast bar and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile floors in entry,...
Vacation at The Coconut Plantation in the renowned Ko Olina Resort | TCP-1174-2
Indulge in the epitome of Hawaiian luxury with our exquisite three-bedroom, three-bathroom, two-story townhome nestled within the prestigious Coconut Plantation in the renowned Ko Olina Resort. Impeccably maintained inside and out, this opulent retreat boasts newly...
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Boasting an extraordinary beachfront location,...