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.
Pool, hot tub, tennis courts! Short walk to beach, dining.
Walk to Brennecke's Beach, Poipu Beach Park, Kiahuna Beach, Shipwreck Beach, the Hyatt beach, and more. Restaurants in walking distance include Brennecke's Beach Broiler and Kalapaki Joe's, both Kauai classics you won't want to miss. Our Poipu rentals at Kahala at Poipu...
Sugar Beach Resort Condo w/ A/C, Shared Grill-Close to Beaches
Sugar Beach Resort 309Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Golf Course Front Condo Near the Beach W/ Shared Pool, Balcony & WiFi
Kapalua Golf Villas 16V3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'What better place than Maui to let all of life's worries simply slip away with the tide? Sitting in the heart...
A Luxury Dolphin Suite with Magnificent Oceanfront..The Ultimate Family Hideaway
As you enter the Dolphin Suite from your private elevator, you will be met with excellence in every way…The Dolphin Suite at Milowai Ma’alaea offers a luxurious and comfortable family hideaway. It stands out as an exceptional vacation condo for families seeking a...
Cozy Mountain View Haven with 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...
Ilikai Hotel's Deluxe One-Bedroom Unit with views of the Ala Wai Yacht Harbor and Ala Moana Beach!
Look no further, welcome to your dream vacation spot! This great condo is located within the OCEANFRONT Ilikai Hotel on the 12th floor and offers exquisite views of the ocean overlooking the Ala Wai Yacht harbor and Pacific Ocean. You'll be love waking up to the...
Magnificent ocean-view condo with golf, pool, balcony, & grilling area
Kauhale Makai Penthouse 607Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy spectacular views of daily sunrises and sunsets when you book a stay at Kauhale Makai Penthouse 607!...
Plantation Hale w/pool next to Coconut Marketplace in Kapaa (J15)
Welcome to our beautiful coconut coast condo! This is a one bedroom condo in Kapaa on the island of Kauai. It has a King size bed in the bedroom and a double sleeper sofa in the living room. That means it comfortably sleeps up to 4. The condo features a full kitchen,...
Maui Sunset Vacation Rentals B506
The island life from your top floor suite, relax on the large private covered lanai deck at the end of a long day of island living. Or see the ocean from the a/c living room, its time to unwind.Popular B side building on the 5th floor. Large private condominium...
Tropical mini resort home in paradise 1ac yard. Whole home beautifully upgraded
For a group of 8 or less, one story of this beautiful tropical themed home would be sufficient space. For more than 8 people we provide extra sleeping with beautiful pull out queen beds .And lower level for super amount of storage space. bathroom , dining and living...
Hale Kai O Kihei Condo w/ Shared Pool, Ocean View-Beaches and Beyond
Hale Kai O Kihei 206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This Hale Kai O’ Kihei condo offers a breathtaking ocean view from every room and includes a private lanai that...
Wailea Elua Village | 2008
Wailea Elua Village 2008 is a luxurious vacation rental situated along the southern coastline of Maui in the desirable Wailea region. This elegant condo offers a serene retreat for travelers seeking a blend of comfort and natural beauty. The interior of this one-bedroom...
Stunning! Diamond Head Oceanfront Lanai Condo - Sleeps 5
Legally permitted vacation rental - 2947 Kalakaua Ave #201A Spacious Condo with incredible Ocean views from our private oversized Lanai.Fitted with a new kitchen in March 2021 along with new living room furniture and 2 new comfortable Queen beds in the bedroom- We are...
Honu Harmony | Pools, Golf Privileges, & More
Summary:When choosing the perfect destination for your upcoming vacation, where you’ll stay is of the highest importance. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:You want a place that can accommodate the whole group not just...
Aloha Condos, Keauhou Kona Surf and Racquet Club, Townhome 187, Oceanfront, AC
Direct Oceanfront LocationFree Wireless High Speed InternetFully Equipped Kitchen & Washer/DryerPrivate Oceanfront LanaiOceanfront Master Bedroom• Great Oceanfront Location• Pool, Cabana & BBQs• 3 Lighted Tennis Courts• Tropical Gardens & Flowers• Golfing,...
Ilikai 734 - Beautiful Ocean & Lagoon View Suite
Relax on the balcony and enjoy the gorgeous lagoon and ocean views. This spacious 7th floor suite overlooks the famous Duke Kahanamoku Lagoon and Beach with ocean views of the famous surf spot Kaiser Bowls.The suite is nicely decorated with one Queen size bed and one...
Westin Nanea in Maui Available December 23-Dec 30, 2024
Come visit the lovely Westin Nanea Villa on the Kaanapali Coast of beautiful Maui. This property features a spacious 2 bedroom villa with full kitchen, living room, dining area, balcony or patio and washer/dryer. A Large Pool and Hot tub and Just Steps to the Beach,...
Spacious 1-Bedroom in Downtown Honolulu - Perfect for Families and Travelers!
Experience the best of urban living in this large, 850 sq. ft. condo, fully furnished and equipped with modern appliances. This condo is ideal for families, business travelers, or anyone seeking a comfortable and affordable stay in the heart of...
Makana Kai Hale: Oceanfront House on Famous Ali'i Drive
Located right on the water, Makana Kai, gift of the sea, has been family-owned for more than 40 years and retains the feeling of visiting a beloved and well-furnished home. The house has been renovated with a new kitchen, appliances, beds, fans, furnishings, and a...
Oceanview 2BR/2BA Condo: Steps from Beach, Pool & Tennis | Kihei Paradise
Experience the ultimate Maui getaway in this stunning 2-bedroom, 2-bathroom corner unit at Maui Vista Resort in sunny Kihei. Perfect for families, couples, or friends seeking a tropical escape. Condo Highlights:*Breathtaking ocean and sunset views from private...
Mai Tide: New N Shore Oceanfront Studio, AC, 30 Day
Mai Tide is a beautiful North Shore Hau'ula beach guest home with 30'+ of ocean frontage, spectacular sunrises & majestic mountain views. Dine on the lanai with turquoise ocean waters so close you can almost touch it. Our home overlooks the sea & mountains (a rare &...
Waikiki Banyan Ocean View Close to Beach + 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...
See Maui on a Budget. Stay at Honokowai Palms Across from the Ocean!
Close to scuba diving, surfing, and more, this smoke-free condo brings it all within reach. There's convenient onsite parking, so you can leave your vehicle behind and let your feet make short work of the 1-minute walk to Honokowai Beach Park or the 10-minute walk to...
Nani Kai Hale #301 on Sugar Beach
Welcome to Nani Kai Hale 301, a wonderful 1 bedroom 2 full bath condo right on the Pacific Ocean! Enjoy views of both Haleakala and Molokini from the comfort of the air conditioned living room. Relax and dine in the fully remodeled kitchen and living room area....
Kona Makai 6-305 GORGEOUS OCEANFRONT, TOP FLOOR, 2 BEDROOM
Absolutely stunning unit at Kona Makai! Unit#6-305 is a gorgeous fully remodeled top floor unit. It features a spacious 2 bedroom, 1 bathroom oceanfront space of 779 square feet & an 122 square foot lanai. This condo can sleep up to 6! Breathtaking ocean, mountain, and...
Kauai Exclusive - Pili Mai 11B - AC, Pool & Fitness Center in Sunny Poipu
Enjoy this brand-new, two-level suite with plantation-style architecture. Pili Mai 11B is a spacious 4-bedroom, 3.5-bathroom condo featuring two master bedrooms with ensuite bathrooms, upgraded amenities such as A/C, Marbau flooring, granite countertops, Bosch...
Oceanfront Maunaloa Condo, Steps to Pool & Beach!
No, that isn't a greenscreen — the oceanfront views at this condo are real, and are best enjoyed with a balmy breeze and a cool beverage on your next visit to the island of Moloka'i. Located in the Kepuhi Beach Resort, this vacation rental hosts a lofted bedroom, a...
50% drop in price 2 bedroom Westin Kaanapali Ocean ResortVilla's12/31/23-1/7/24
Imagine waking up to palm trees swaying and the ocean's sound, straight out of a dream! Paradise, Whales, Sea Turtles, and Rainbows.Indulge yourself in the ultimate getaway! Whether you prefer the beach, the pool, or shopping downtown. The Westin has almost everything...
Lovely Hawaiian Monarch Studio | Pool + Gym
This beautifully remodeled studio offers mountain, city and partial ocean views and sleeps 2. This unit is located on the 20th floor. Elevators are available. This unit features ac, smart tv, wifi and cable a short walk from Fort DeRussy Beach Park, Hilton Hawaiian...
Come To Maui, ⛰Hawaii 🌺<br>Hilton 🥰Beach Club Resort🏝<br>1Bdr sleep 4 Privately😍
Aloha 🌺Kaanapali Beach Club now owned by Hilton 🥰🏖🎉All One Bedrooms Sleep 4 with Privacy ;) priced here is a scenic view room upgrades to Oceanview are addntl based on season and Availability🌺🐝 This resort has one of the largest pools🏊🏼 on the...
Wailea Grand Champions | 27
Nestled in the heart of Wailea, this charming Grand Champions residence offers a tranquil retreat that feels like your own private Hawaiian sanctuary. As you step through the door, you're immediately embraced by the warmth of island living and the thoughtful design that...
Heavenly Hana Paradise, spacious studio apartment at the end of the Road to Hana
The Ho'okipa Surf Suite Studio at Heavenly Hana Paradise features a private lanai and entrance, surrounded by fresh ginger, gardenia, and tropical greenery. The en suite bathroom includes plush bath towels, hand towels, complementary toiletries, and beach towels.Air...
Mauna Kea Villa 3040 - Hawaiian Masterpiece
This grand, single-level, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living and Sonos sound system, a chefs' kitchen with Wolf and Sub-Zero appliances/wine refrigerator, a dining area with adjoining wet bar,...
Oceanfront - Kanaloa Resort #2202
****Central AC is optional, and available for an additional fee*****please notify management after bookingRelax and enjoy your vacation in a spacious oceanfront 2 bedroom, 2 bath condo in the famous Keauhou resort area. Located approximately 5 miles south of Kailua...
Ocean Front Napili Point C20 Amazing View A/C Freshly Remodeled for 2025!
If the calendar for C20 is not available for your dates, please look at the availability for C25 VRBO #641701.We recently made some major upgrades in late 2024 to the condo including all new tile flooring throughout the unit along with completely remodeled bathrooms...
Hawaiian Dream - 8th floor Ocean View w/ Full Kitchen
Legally permitted vacation rental - 2947 Kalakaua Ave #802** For your health and safety, we utilize additional Sterilization procedures between reservations.High Floor with Full Kitchen 'Residential' Suite - 1 Bedroom, Full KitchenHigh Floor with Full Kitchen...
Casa De Emdeko 204 - Air Conditioning! Elevators! REMODELED IN 2019!
Casa 204 is an excellent, affordable 2nd floor property that you will certainly love. Unit#204 was REMODELED IN APRIL 2019 with all new flooring, furniture, kitchen, bathrooms, paint, appliances! Central AC, WIFI, Elevators, Beach gear! Look no further!Unit#204 is a...
KS 546 Fun Maui Vacation BeachFront Resort w Pools
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 Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Volcano Escape Epic Tiny Home on Lava Field with Volcano Views
Experience a magical, memorable retreat at The Ohana House—a unique, off-grid tiny house on the Kalapana lava beds near the base of Kilauea Volcano. Enjoy epic views of the volcano & expansive black lava fields, double rainbows and epic stargazing while enjoying...
Oceanfront corner condo with cohesive design
Napili Puamala 128 is a remodeled Studio condo which features amenities such as an open-concept layout and a ground-floor lanai. This condo does not have A/C. Located on the ground floor, this condo can accommodate 4 guests with a Queen size bed and Queen size sofa...
Wailua Bay View Condo w/Private Washer/Dryer, Shared Pool, WiFi - Near Beaches
Wailua Bay View 206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wailua Bay View Kauai vacation condos are exactly what you have been looking for. Located on the Coconut Coast,...
Maui Resort Rentals: Honua Kai Hokulani 636 – Ocean & Mountain Views w/ King Size Balcony!
Hokulani 636 is a luxurious two-bedroom oceanview corner suite and one of the few offerings at Honua Kai that affords views of both scenes that Maui is famous for... the relaxing blue Pacific Ocean and the majestic West Maui Mountains.The generous 1240 sq. ft. interior...
Elegant Puamana Home with top quality finishes, AC, w pool in tropical oasis.
Discover paradise in this elegant Puamana 185-4, offering expansive ocean views from every room. The open-plan layout creates a seamless flow between living spaces, while the downstairs lanai beckons with its tropical ambiance and stunning greenbelt vistas. It is...
Delightful condo near beaches with pool & hot tub & private balcony
Kona Bali Kai #171Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Shrug off your concerns and slip into some beachy flip-flops, because this one-bedroom home is sure to put a smile...
Aloha Condos, Keauhou Kona Surf and Racquet Club, Condo 2-102, Oceanfront
Oceanfront Location Expansive Ocean Views Ground-Floor 2-BR /2-BA Condo with Kitchen Kitchen & Washer/Dryer Private Oceanfront Lanai Oceanfront Master Bedroom • Great Oceanfront Location• Pool, Cabana & BBQs• 3 Lighted Tennis Courts• Tropical Gardens &...
Pali Kai Cottage 16AB - Private Oceanfront Cottage
Newly renovated !!! New pictures to follow.The Oceanfront Pali Kai cottages are perched on a bluff over looking beautiful Kalapaki Bay. This cottage features 4 bedrooms/ 4 bathrooms , free wifi, AC/washer/dryer. Located on a private/gated street. Set in the heart of the...
Maui Banyan-Top Floor Unit, Right Across from the Beach!
Beautifully remodeled top floor unit in low-rise building, directly across the street from the world-famous Kamaole Beach Park II. Cherry cabinetry, quartz counters, brushed nickel fixtures, all tile, no carpet. 65' Smart TV in living room. Wireless internet available...
Perch - Oceanfront Tranquility: 1BR Condo w/ Views
Experience the ultimate in oceanfront living at this luxurious condo unit at the Aston Mahana at Kaanapali. Renowned for its breathtaking Pacific Ocean views, this resort offers a tranquil escape on Maui's stunning shores. This spacious one-bedroom suite on the 10th...
The Jungle House {AC/ Ocean View}
Welcome to our breathtaking Hawaiian retreat! Nestled on the shores of paradise, our house offers a stunning ocean view experience. Immerse yourself in island living with this beautifully appointed home, featuring modern amenities, spacious interiors, and a private...
Partial Ocean View from private lanai, Queen Bed.....fully furnished condo
This condo is equipped with everything you would want/need for your stay, from fully set up kitchen, full size washer/dryer, TV in living area, electronics, iron/iron board, beach gear, free internet, linens, etc. The large second floor lanai is the most wonderful place...