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.
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...
Upgraded Makaha remote work and surf oceanfront condo
Your own paradise living right on the beach with remote work friendly set up! This newly upgraded beautiful oceanfront condo offers mesmerizing view of the sunset in the balcony, breathtaking colors of the deep ocean and peaceful sound of waves in a serene and quiet...
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...
Modern Kihei Beachside Studio Vistas
Summary:Upscale remodel with high-end furnishings studio oasis situated directly across from Kameole Beach. Fantastic lanai with direct ocean views. Experience the resort's many amenities such as tennis courts, pool and jacuzzi and grills. We provide everything from...
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 breaching...
Stylish Waikiki Escape with Pool Access! 2 Relaxing Units, Pets Allowed
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.✦ Each room is 878 sq. ft, equipped with complimentary toiletries, TV.✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival...
Kaneohe Bay views with AC in Kahaluu
Enjoy a tropical yard with ocean and mountain views. The large attached and furnished back one bedroom one bathroom apartment has its own separate entrance, high ceilings, skylights, Air Conditioning, ceiling fans and a view of the tropical backyard. Views of Kaneohe...
Kai Hale-Anini Beachfront Paradise
Oceanfront luxury meets Old Hawai‘i charm at Kai Hale, your private beachfront escape on magical Anini Beach. Just steps from the sand, this peaceful retreat features panoramic ocean views, open-air living with floor-to-ceiling glass doors, private lanais, and a gourmet...
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 &...
Charming Sea Village 3304: 1-bedroom ocean-view retreat in Kailua-Kona.
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...
Romantic Kona Hideaway-Modern
Tucked away in a peaceful native Hawaiian forest, this modern hideaway offers the perfect romantic escape just 10 miles from Kona’s beaches, airport, and town. Thoughtfully designed for couples, honeymooners, and those craving serenity, this stand-alone retreat blends...
Hale Hoʻomalie – Private Pool & Golf Views
Summary:Single-level Poipu retreat with private pool, jetted tub, golf course frontage, and mountain views. Located in the peaceful Kiahuna Golf Village, this spacious 3-bedroom home features open-concept living, a fully equipped kitchen, two lanais, and beach gear for...
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...
2/2 Kihei Beachside Resort Resort Vistas
Summary:Upscale remodel with high-end furnishings 2br oasis situated directly across from Kameole Beach. Fantastic lanai with direct ocean views. Experience the resorts many amenities such as tennis courts, pool and jacuzzi and grills. We provide everything from beach...
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 KÄÊ»anapali Ocean Resort Villas North. With about 1,230 square feet of space, this flexible villa setup comfortably sleeps up to eight guests.The lockoff...
Serene Sandy Beach Golf Course Home
***Location and Getting Around***Welcome to the heart of Hawaii Kai—your gateway to adventure and relaxation! Just a 5-minute stroll brings you to the golden sands of Sandy Beach, perfect for sunrise walks or catching waves. Hungry or need supplies? You're only a few...
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
Nestled in Honolulu’s prestigious Portlock neighborhood, Hale Ola is a refined coastal retreat where luxury, comfort, and panoramic ocean views come together seamlessly. This single-level estate spans 3,744 square feet and accommodates up to twelve guests across five...
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...
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...
Aqua Aloha Surf Waikiki 600 Superior Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 600 Superior Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 261 Sq Ft.Aqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for...
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...
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 kitchen...
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 central...
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 the...
@ Marbella Lane – Oceanview Horizon Escape Studio
Summary:Escape to Ocean Serenity, a beautifully designed studio ideally located for your Hawaiian getaway in Honolulu. Known as Horizon Escape, this inviting retreat offers stunning beach views and is just steps from the sand. Enjoy modern comforts including air...
Kaanapali Shores 702 Beachfront 2BR condo w stunning ocean views
Kaanapali Shores 702 Spectacular Panoramic Direct Oceanfront Views from this Exquisite Remodeled West Maui CondoWelcome to your Maui Retreat: A show-stopping direct-oceanfront residence perched on the 7th floor of the acclaimed Kaanapali Shores Resort in Kaanapali, West...
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...
Elegant Oceanfront w/ Pool & Hot Tub in Maui Sunset
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Maui Sunset offers a bright and breezy, fully renovated 5th-floor ocean-view 2BR/2BA retreat perfectly...
Spacious Design Studio 3 mins from the beach
This spacious studio is located in the heart of Waikiki, within 5 minutes walk to Waikiki Beach. The space is completely remodelled with high end furnishings.Features:- a fully equipped kitchen- two double beds - perfect for families and groups!- a luxurious bathroom...
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...
Elegant Oceanfront 2BR Home with Vast Panoramic Views, Steps from Kehena Beach
The Jewel Box is your private oceanfront retreat perched above Kehena’s ancient lava cliffs. From the lanai, sweeping ocean views unfold—sunrise, sea spray, and the pulse of island life. Dolphins and whales pass by too. This fully stocked home is a short walk to Kehena...
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 Oʻahu’s most sought-after 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭𝐬 — 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐊𝐨 𝐎𝐥𝐢𝐧𝐚 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 ($500–$1000 𝐎𝐅𝐅...
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...