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.
Ali'i Point #9: Lavish Oceanfront Home w/Pool & Spa- Relax & Watch the Waves
Experience the serene beauty of Hawaiian living in **Ali'i Point #9**, a spacious 3-bedroom, 3.5-bath vacation home located on Alii Drive in Kailua Kona, HI. Spanning 3,190 square feet, this inviting oasis is designed for comfort and relaxation, making it perfect for...
Stunning Oceanview * Oceanfront 2/ 2 Bath Prime Location
Step inside and be greeted by the newly refurnished and redecorated interior that exudes a sense of calm and relaxation. The condo features two spacious bedrooms, each equipped with a comfortable king-size bed for a restful night's sleep. The bathrooms are fitted with...
Escape To Maui! Beautiful 1 Bedroom With Amazing Ocean Views
This lovely one bedroom unit, located in the Royal Kahana Resort has beautiful sweeping views across the water including the islands of Lanai and Molokai. You can enjoy the water view and spectacular sunsets from the lania, living room and bedroom. The Royal Kahana is...
Marriott KoOlina Beach Club, TWO Bedroom, Oceanfront Resort
Please choose a Friday through Sunday check-in for a 7-night stay. Thank you for choosing Dash Realty Group of Windermere, Florida. We are a registered Fla. Seller of Travel Ref. No. ST42435.Traveling with 2-4 people? Take a look at our STUDIO ad on VRBO:VRBO #1012183...
Upgraded Condo in North Shore Hanalei/ Princeville Kauai
‘HANALEI BAY DREAMS' PLANTATION AT PRINCEVILLE #612 - Managed by The Parrish Collection Kauai- The best location and unit in the complex. Tasteful Hawaiian decor with air-conditioned comfort in a luxurious 2 bedroom condo steps from pool and jacuzzi. SPECIAL RATES...
Maui Resort Rentals: Honua Kai Hokulani 929 - 9th Floor, Sweeping Ocean Views from Every Room, Year-Round Sunsets!
Welcome home to what is unquestionably one of the finest residences on offer at Honua Kai. This expansive three-bedroom deluxe ocean view affords sweeping 9th-floor views of the Pacific Ocean and enjoys a commanding vantage point above the adjacent resort wings that...
"Serenity" at Islander on the Beach 326- Oceanfront Studio
Serenity – Oceanfront Bliss at Islander on the Beach 326Welcome to Serenity, a top-floor oceanfront studio at Islander on the Beach where tranquil rhythms and breathtaking views create your perfect Kauai retreat. With sweeping, unobstructed vistas of the Pacific and...
WBH C212 Ocean Views 2BD Beachfront Kihei Condo | Lounge by the Pool
NEW LISTING! Spectacular Ocean and Sunset Views from this 2 Bedroom South Maui Beachfront Condo!Follow the trade winds across the Pacific to find your private Hawaiian oasis! Welcome to Waiohuli Beach Hale C212, an exquisite oceanfront retreat tucked away in the heart...
Honu La'e - 4 Bedroom, 4 Bath Ocean Front Vacation Home in Poipu with A/C
Perfect for your custom Poipu vacation, Honu La`e has 4 bedroom 4 bathrooms. Located near Koloa Landing in the heart of Kauai’s scenic South Shore, Honu La`e is close to ocean activities including world class body surfing, several surf breaks, snorkeling and swimming....
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean View | 2-Bedroom Condo, Huge Lanai, Stunning View! HKH-229
Sophisticated 2-bedroom villa in Hokulani Tower with ocean views, expansive lanai, gourmet kitchen, and elegant island decor-perfect for relaxing or entertaining in tropical Maui luxury.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an...
Maui Resort Rentals: Honua Kai Hokulani 140 – Upgraded Large Ground Floor 1BR, Spacious Lawn Area + Easy Pools/Beach Access
Hokulani 140 is a luxurious ground floor suite with one of Honua Kai's largest one-bedroom floor plans and easy access to the pools, beach, and B.B.Qs. Your group will have plenty of space to spread out on the large adjacent lawn area. Take in the views of the majestic...
1BR Ocean View Condo with King Bed & Free Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
🌴Beautiful Condo Located on the Kona Country Club Golf Course🌴
Country Club Villas #216 is a spacious 2-bedroom, 2-bath condo set on the 18th fairway of the Kona Country Club with spectacular Golf Course and Ocean views. This beautiful condo offers a number of amenities including: - Resort Swimming Pools - all with ocean views -...
Heavenly Hawaii Retreat Home near Hilo, Ocean & Waterfalls
Welcome to the perfect Hawaii Homebase for you & your family-friends! Enjoy tons of space and privacy in this gorgeous, pet friendly, 4BR/2BA fully appointed home on a five acre fruit farm, designed for up to 13 guests. This retreat offers ocean views, various indoor &...
Hale I'a: 5 Bedroom Home with Oceanfront Pool at Sunset Beach
Minimum 30-day consecutive rental required. Beachfront Home with swimming pool at Sunset Beach, North Shore, OahuLocated on a privately owned road with only one-way access in and out, which provides privacy and exclusivity. There are over 6000 square feet of spacious...
Villas of Kamalii #27, Stylish Luxury Princeville Condo, Mountain Views, A/C
Welcome to your dream vacation home at Villas of Kamali'i #27, a luxurious tri-level townhome nestled within a private and gated community on the stunning island of Kauai. This newly updated and elegant air-conditioned villa is in an upscale gated community in...
"Surf's Up!" at Islander on the Beach 327 a Oceanfront Studio
Surf's Up! – Oceanfront Studio Retreat at Islander on the Beach 327Welcome to Surf's Up!, a newly refreshed top-floor oceanfront studio at Islander on the Beach. Here, the gentle sound of the waves and sweeping ocean views create the perfect backdrop for your island...
Located on Kauai's magnificent north shore.
Watson Home in Hanalei on Kauai's magnificent north shore. This two-level home offers partial ocean views from large picture windows in the spacious living area. The wrap-around lanai provides beautiful views of the large back yard and lush, tropical surroundings.Just...
Bright Corner unit with Stunning Views! AC, W/D, Wi-Fi, Washlet, parking!
Four Paddle #2302 – 2140 Kuhio Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You'll love the stunning views of this 23rd floor one-bedroom corner condo (577 sf plus partial ocean-view lanai with table and chairs)! With central AC, this...
Direct Ocean Front, Renovated1 Bdrm Condo with Sweeping Views of the East Shore
This charming ocean front condo is unit # 226 at the Kaha Lani Resort, which is located on Kauai 's beautiful east shore, the famous 'Royal Coconut Coast'. From the lanai of this island home, you can view the endless stretch of shoreline looking both northward and...
Beautiful 1bd, views of koi pond and ocean views
Papakea D207 is a 1-bedroom, 1-bathroom condo that sleeps 4 guests. This condo offers a fully equipped and beautifully remodeled kitchen, featuring custom cabinets, granite countertops, recessed lighting, and stainless-steel appliances. Stay cool with window A/C in the...
3 Bedroom Home - in Paia Town - Walk to it All
If you want to be in Paia, or minutes to Ho'okipa or Sprecklesville, you'll like this location. This is the relaxed, non-touristy Hawaiian experience. Plus, Paia is the north shore hub for all sports wind and wave. And, Paia is a walk-able town.The north shore has no...
Kona Plaza#409: Top Floor, Downtown, Rare 3 bedroom Penthouse with Ocean View
Kona Plaza#409: You've found one of the most rare features in Kona. A Downtown Kona 3 bedroom Top Floor Pent House with Air Conditioning, Elevators, and can sleep up to 8. Discover this truly one-of-a-kind penthouse condo nestled in the heart of vibrant downtown Kona....
Luxury Zen Retreat overlooking Hanalei
Indulge in a spectacular retreat at this spacious and stunning home overlooking the famous Hanalei Bay, Kauai. This elegant 4400 square foot property is ideal for families or couples looking for a private, yet handy location because of its peaceful atmosphere. Be...
272-2 Oceanfront Magic
Experience Oceanfront Bliss at Puamana, MauiWelcome to your perfect Maui getaway, a modern and beautifully updated oceanfront townhome in the serene Puamana community. Offering unobstructed views of the Pacific Ocean, this home invites you to immerse yourself in the...
Maui Resort Rentals: Honua Kai Hokulani 933 - Exceptional 9th Floor Ocean View Studio!
This incredible studio suite affords sweeping 9th-floor views of the Pacific Ocean and enjoys a commanding vantage point above the adjacent resort wings that compromise the views from floors 8 and below. Nestled in the Hokulani interior courtyard, the view plane is so...
OCEAN VIEWS-BUILDING 10-STUNNING REMODEL-AC-WELL EQUIPPED-METICULOUS CLEANING
Book with confidence, this stunning 1 bedroom, 2 bathroom condo at Kamaole Sands has been completely remodeled. Everything in the condo is new and finished with high end materials. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in...
Kahala 414 - Private Two-Bedroom Condo in Poipu Kai
KAHALA 414 AT KOLOA KAI VACATION RENTALSSpacious Two-Bedroom Ground-Floor Retreat in Poipu Kai ResortWelcome to Kahala 414, a relaxing and well-appointed two-bedroom, two-bathroom condo located in the heart of the beautiful Poipu Kai Resort. This ground-floor retreat...
Luxurious 3BR Retreat in Poipu Kai Resort with Pool, Elevator, & Beach Access
Kauai’s Luxury Tropical Retreat in the heart of Poipu Kai Resort!Located on the beautiful island of Kauai, this 3-bedroom, 3-bath unit offers the highest level of luxury in the Poipu Kai Resort area. These amazing accommodations feature 2 King primary suites and an...
Hotel Moloka’i 1 Bedroom Condo
Yea! Our WiFi has just been upgraded, September 2022, in our remodeled, privately owned unit. Our oceanside condo is located in the only hotel on the island, Hotel Moloka’i, and is within a 2 mile walking distance from Kaunakakai town.There is no keeping track of...
Top Floor Condo Close to Beaches
For those who want to escape and relax in one of the most luxurious, truly upscale accommodations on Kauai's incredibly beautiful north shore, Plantations at Princeville is the place.Everything in the professionally designed interior is upgraded - and absolutely...
NEW LISTING Private Home across from Keawakapu Beach Tennis Pickleball Court!
Keawakapu Retreat- " Alani" NEW LISTING ON VRBO, 4.9 Overall rating on other booking platforms!!! This recently remodeled home is nestled on over an acre property with four private homes. An estate from Old Hawaii-Days gone by. This three bedroom two bath home sits on a...
Wailea Ekahi 45B-Great Rates,Lovely New Kitchen, Large Lanai, Pool #3 w/BBQ
Unit 45B is located in Building 45 on the ground floor. This lovely one bedroom, two bathroom condo has a 400 square foot lanai with picturesque garden and ocean views and Quiet Pool 3 just steps away. Patio equipped with spacious patio seating & chaise lounge. This...
Spectacular Treetop Oceanfront View - Central A/C - Sleeps 6 - Turtles & Whales
Aloha, MAUI IS OPEN for tourists to visit!! The devastating wildfires in Lahaina are incredibly sad, but your condo is far away from them, and on the other side of the mountains. The Eastern side of Maui has hundreds of things to do, visit and see, without ever...
"Premier Oceanfront" at Lanikai 123 a Spacious 2 Bedroom | 2 Bathroom Condo
Lanikai 123 – Premier Oceanfront Living on Kauai's Coconut CoastEscape to Lanikai 123, a spacious second-floor oceanfront condo offering panoramic views of Wailua Bay, a beautifully updated kitchen, and inviting indoor-outdoor living. With two bedrooms and two...
❤️PiH❤️ Makai Living ★ Bright and Modern ★ Close to Beach
Brought to you by Paradise in Hawaii Luxury Homes.Fresh and modern, Makai Living has it all. Makai means towards the ocean in Hawaiian. Makai Living at Fairways is a fully renovated modern two bedroom home within walking distance to the beach and ocean. It is located in...
Peaceful Big Island Hawaii Retreat with Private Beach Club Access
Our home is a classic Hawaiian style bungalow (no shared walls) 3 BR / 3 Bath (2 master ensuite) with attached garage parking. It's a space to relax, recharge and enjoy "island time". We have beach cruiser bikes, beach towels, snorkel gear, and paddle boards for your...
Luxury Oceanview Waipouli Beach Resort & Spa
Your Sunrise Vacation Home™Enjoy your Kauai Vacation at the beautiful Oceanfront Waipouli Beach Resort & Spa. Located in one of the newest resorts on Kauai, H-402 is a 2 bedroom, 3 bathroom Oceanfront Penthouse Condo. You will enjoy relaxing sounds of waves hitting...
150K Reno-Ocean View* Across from Beach*PoolTennis
BRAND NEW 150K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Ocean views+Breeze from the Lanai located in BLDG 5- Best in Kamaole Sands+directly across from the golden sand+crystal waters at Kamaole III..Walking distance to everything South Kihei...
Mauna Lani Terrace J103
Sophisticated, contemporary three bedroom condominium located at the point where the ancient fish ponds meet the Pacific. Enjoy the wide, unobstructed view from your lanai with your morning coffee and your sunset cocktail.Recently renovated, Mauna Lani Terrace J103...
Bright, modern home w/ocean views from the huge wraparound deck & private pool
Saltwater HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This beautiful home is perfect for the family getaway to the Garden Isle you've been looking for. You'll love taking in...
Tropical Romantic S. Kona Cottage with Incredible Oceanview
Makalani (Heavenly View) Cottage is a delightfully romantic cottage surrounded by a tropical garden in South Kona's coffee-belt with a breathtaking panoramic view of the Pacific Ocean. For the adventurous traveler seeking authentic Hawaiian beauty and serenity, you can...
Kiahuna - Ocean View - Ground Floor on Great Lawn with AC!
Aloha and welcome to your dream vacation destination in Kauai! Let me introduce you to our cozy beach bungalow, located in the sunny south shore of the island. You'll be staying in Building 27 and entering unit #175, an oceanview condo on the Kiahuna "Great Lawn." This...
Kauai Exclusive - Poipu Makani Lani - Private Home w/ Pool, Spa & AC
Named "Heavenly Breezes" for a reason, Poipu Makani Lani is a 4-bedroom, 3.5-bathroom custom home that is perfectly perched on the Kiahuna Golf Course's first hole. This modern single-level home offers three luxury master suites and a guest suite creating ultimate...
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean SunsetsDiscounts for Extended Stays. Digital Nomads Welcome!Clean & Green Sleep Suite Beyond Luxury to Vibrance Thank you so much for considering A502 Maui Sunset for your Time, Energy and Money....
House of the Turtle (CR 18) at Champion Ridge: Pool, Spa, AC & Stunning Views
Tranquility and luxury await at House of the Turtle, a single-level residence offering spectacular Kohala Mountain views in the gated Champion Ridge community. Nestled in the heart of the Mauna Lani Resort, this 4,000-square-foot estate balances island elegance and...
Island Style Condo With Private Pathway To Hideaway Beach
This Pali Ke Kua townhouse condo is located in the town of Princeville on the lush North Shore of Kauai. The North Shore is known for its beautiful tranquil beaches and majestic mountain peaks. The world famous Na Pali Coast is located here on the North Shore. You will...
Pali Ke Kua #118: Ocean views from every room and gorgeous Bali Hai sunset!
1 bedroom, 1 bathroom corner unit offering a cozy bamboo motif that resonates with old Hawaii and when times were simple. The idyllic getaway from the fast-paced crowds, and ultra-modern world of hotel rooms. Ocean views from every room. Curl up on the lanai with a good...
KONA ISLE C38: TOP FLOOR CORNER REMODELED W/AC & INCREDIBLE OCEAN VIEWS.
Looking for the best of the best at Kona Isle? Kona Isle#C38 is arguably one of the best units in the entire development. Top Floor West Corner of Building C, you've got INCREDIBLE OCEAN VIEWS! This unit is fully remodeled from Top to Bottom, and has absolutely nearly...
Enjoy Paradise at Our Mauna Lani Villa
Our townhome is located in the exclusive Mauna Lani Resort that is anchored by the Mauna Lani Auberge and Fairmont Orchid hotels. Being our guest gives you parking and lounge chair access at the Mauna Lani Beach Club which is a short 2 mile drive away. The walk to the...