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.
Kamaole Sands 4-306 - Steps to Kamaole III Beach - Split AC + Pool + King Bed
Welcome to Kamaole Sands 4-306 - a beautifully remodeled, third-floor condo designed for comfort, luxury, and an authentic Maui experience. This bright and airy one-bedroom retreat accommodates up to four guests and features a fully upgraded interior, including a modern...
Remodeled unit 4 Star Beachfront Resort-Steps to Beach,Pools,Jacuzzi,Restaurants
Kauai Beach Resort is a magnificent 4-star oceanfront luxury resort on a secluded 3-mile stretch of Kauai's eastern coast. Just minutes from the Lihue Airport, the resort location is perfect for hiking the Na Pali Coast, exploring Waimea Canyon, or relaxing and...
Mauna Lani 4 BR Luxury! Golf & Beach Club
Summary:Located in the prestigious Mauna Lani resort on the Big Island of Hawaii! With 4 bedroom and 4 en-suite bathrooms, this home can accommodate up to 8 guests. All of your family and friends can be in one place and still have privacy. Our concierge can help plan...
Beachfront, Modern Home, Just Steps to the Sand
This sleek and modern, beautifully appointed 2 bedroom beachfront home is located on one of the most beautiful beaches in the world. Impeccable decor, combined with expansive panoramic ocean views make this home a sanctuary for enjoying Kauai's majestic North Shore. Now...
Oceanfront! Newly Remodeled, modern condo. Sealodge at Princeville. AC / WiFi
Ocean Front with breathtaking views from every room. Our one bedroom, one bath, well equipped condo sits on the bluff of Kauai's beautiful North Shore. Completely remodeled from floor to ceiling, including a new walk-in shower, new kitchen/bath cabinets and koa...
11th Floor Waikiki Ocean, Lagoon & Marina Views! Walk to Beach! Washlet!
Ilikai Marina #1184 – 1765 Ala Moana Blvd.Stunning panoramic views of the Pacific Ocean, Duke Kahanamoku Lagoon/Beach, and marina! Bring your binoculars!CONSTRUCTION NOTICE: Due to building exterior spalling repairs, please expect some construction noise during weekday...
Kailua Village #701: Top Floor, Corner Penthouse Remodeled in Downtown Kona.
Looking for the best of the best in Downtown Kona? Look no further, you've found the best property. Kailua Village#701 has the absolute perfect location. Located on the Top Floor (7th), on the very corner for this High Rise Development in Kona. Walking Distance to...
SUPER SPACIOUS! Privacy entrance. Comfortable and cozy. Quiet and peaceful!
Beautifully decorated spacious one room and one bathroom studio. Sleeps up to 4. Very quiet and peaceful. Wake up rested to the sounds of the doves cooing in the morning. Mini fridge, microwave, coffee maker provided and anything else you may need, just ask. Covered...
Unit 10-401, Hidden Treasure, Bldg 10, Top Floor, Ocean Corner, Nearest to Beach
Congratulations! You have found one of the 'Hidden Treasures' of the Kamaole Sands Condominiums! LOCATION: Our Unit 10-401, being 1,188 square feet of living space and lanai on the TOP-FLOOR OCEAN-CORNER of Building 10, is sunny and well-lit and well-ventilated, secure...
Hale Ohana - Beautiful 'House of the Family' - Poipu Beach - sleeps 6
Hale Ohana, meaning "family house," is nestled in a charming neighborhood, just a 10-minute walk from the stunning crystal blue waters and sandy beaches of the Poipu Beach Resort area. Enjoy activities like surfing, swimming, bodyboarding, sunbathing, snorkeling, and...
Pacific Shores Paradise. Central Air Condition.
Central Air Condition, 2 bedroom/2 bath, fully equipped kitchen, with a tropical theme, Queen beds, FREE WiFi, 55 inch HDTV. Across from BEAUTIFUL sandy Charley Young Beach. Short walk to restaurants, shops, watch surfers at nearby beaches. Twenty minutes from Kahului...
Pono Kai Resort- 1 Bedroom Garden View
Our 1 Bedroom Garden View condo has a fully equipped kitchen, 1 bedroom and 1 full bathroom. The bedroom has a Queen size bed. There is also a pull out queen sleeper sofa in the living room. Very spacious units fully stocked with linens, towels, starter soap and coffee...
Ocean & Island views from this 1 bedroom condo
Welcome to Royal Kahana 612. This oceanfront spacious 6th floor 1 bedroom, 1 bathroom condo offers stunning ocean & surrounding island view. This condo features a remodeled full stocked kitchen with stainless appliances, tastefully decorated, & can accommodate 4 guests....
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...
A Beautiful Condo at the Waters Edge with a Great View
This beautiful condo is at the waters edge in Poipu Beach situated on the third floor. It has a fantastic, unobstructed view of a beautiful bay and the ocean. Taking full advantage of cooling trade winds, this vacation rental is on the end of the complex, which provides...
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 the...
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
** 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...
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 BBQs. 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 -...
Waipouli Beach Resort Exquisite Luxury VIP Oceanfront Condo! AC Pool
Oceanfront! Exquisite Luxury VIP Oceanfront Condo in highly desirable "A" Building at the #1 Ranked Waipouli Beach Resort & Spa on Beautiful Kauai offering stunning Direct Oceanfront views from every room with delightful watercolor sunrises, whale watching (November to...
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...
Aqua Aloha Surf Waikiki Studio
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...
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 vacation...
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 eight and below. Nestled in the Hokulani interior courtyard, the view plane is...
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
Summary:Ground-floor two-bedroom retreat in Poipu Kai Resort, just a short walk to Poipu Beach, Brennecke’s, Shipwreck Beach, and nearby dining and shops. Features two king bedrooms, portable A/C in the primary suite, a private lanai, full kitchen, beach gear, and...
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 keys....
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...