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.
Rolling surf, gentle trade winds, and unparalleled ocean views await you!
Seabreeze #7 – 3065 Kalakaua Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy 180-degree unobstructed panoramic views of the Pacific from this oceanfront property on Diamond Head's coveted Gold Coast.You'll have the entire 7th floor to...
Ocean & Diamond Head Views! Full Kitchen, Lanai, 1 Free Parking! Sleeps 6
Waikiki Sunset #2514 – 229 Paoakalani Ave.Popular 2-bedroom, 1-bath condo (604 sf plus 56-sf lanai, sleeps 6) positioned on the 25th floor in the preferred corner end suite stack with central A/C and spectacular views of Diamond Head, Kapiolani Park, and the Pacific...
Incredible Kekaha Beachfront Estate for 10!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Main Home: This custom home is on a ocean front estate. It has three bedrooms and three bathrooms. The home has large sliding doors that disappear into the walls so you won't know where...
Captivating Ocean Views at Spectacularly Located Makena Surf Resort #C-205
Makena Surf C205Makena Surf Resort, located in the exclusive Makena area, offers a secluded beachfront retreat surrounded by lush tropical landscaping. This gated property features six two- and three-story buildings, each designed to maximize stunning views of the...
Aston Kaanapali Shores - 2BR Garden View - NO Resort or Cleaning Fees
All of our guests have complimentary access to our Maui specialist and support team during their stay.*This condo is in the Aston rental program and is subject to a $11.95/day parking fee to be paid to the front desk on property. {A valid credit card is required to...
8th floor 1bd with great oceanfront views
Enjoy panoramic ocean views from this gorgeous oceanfront condo, Maui Kai 801! It doesn't get more oceanfront than this! Here you will enjoy spectacular sunsets year round, whale watching during winter months, and spotting turtles swimming below while drinking your...
Located in the Heart of Waikiki! Free parking & W/D in the unit!
The Marine Surf Condominium is located right in the middle of Waikiki. This is a breezy and cozy corner unit at Marine surf. The unit was renovated in May 2011. This unit has a unique layout of 1 full bath and 1 half bath for guest convenience. Enjoy the mountain view...
Largest Private Patio on the Ocean and Air-Conditioning
Newly remodeled unit just made available for rentals. This was our home in the 70's and now our vacation home. We want you to enjoy old Hawaii the way we did when we were first married. This is a quiet get away from the hustle of Waikiki but can be reached in under an...
The Drifter - North Shore Loft - Relaxed Luxury
Welcome to The Drifter!! Part of the Kuilima Estates East community, the unit was designed with the goal of offering a “Relaxed Luxury” experience. Meaning, to provide guests with an elevated design aesthetic with a feel-good comfortability. The unit is a loft-style...
Luxurious Waterfront Retreat w/ Views, Soaking Tub, Pools, Hot Tubs at Honua Kai
Honua Kai - Konea 738Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'If you’re considering a luxurious Maui retreat, this beautifully updated one-bedroom condo offers both location...
Kamaole Beach Royale Unit 305:1 Br/2 Ba Across from Kamaole Beach Park I
Enjoy 180 views from the 3rd-floor living room and a private lanai with table and chairs where you can relax and listen to the waves crash on the shore. In the winter months, you can see the whales playing in the ocean and throughout the year you can watch the boats...
Wyndham Bali Hai | 1BR Suite with Resort Access
Summary:Nestled amidst the stunning scenery of Princeville on Kauai, Pahio neighborhood and Hanalei town beckon with a delightful array of restaurants, beaches, galleries, boutiques, and world-class golf courses, all within easy reach. Unwind by one of the two pools or...
Beachfront Gem; Steps from the Glistening Shore
Indulge in the unparalleled beauty of Hawaiian sunsets as you retreat to your own private haven on the ground floor of this conveniently located condo. Revel in the breathtaking ocean and garden views from your expansive lanai (terrace), where you can start your day...
Maui Kamaole i210 - Ocean View and Whales!
Unwind on one of two private lanais while taking in the stunning ocean views. The interior is fully equipped with all the comforts of home, including a fully stocked kitchen, comfortable furnishings, and a spacious living area. After a day of exploring Maui, relax in...
Partial Ocean View! King Bed! A/C, Wi-Fi, Pool, Parking, Close to Beach!
Waikiki Sunset #1812 – 229 Paoakalani Ave.You'll enjoy partial ocean views and great sunsets and city lights at night from this 18th floor, one-bedroom condo (534 sqft plus balcony/lanai), with central AC and free Wi-Fi! 4-person max.Just a 10-minute walk to the best...
Charming 2-bedroom condo. Under new management. 10% off last min booking for Jan
Imagine waking up to the gentle sound of waves and stepping onto your lanai to take in the vast, sparkling ocean stretching out before you. With a fresh cup of coffee or tea in hand, the morning breeze carries a sense of tranquility as you watch the sun rise over the...
FREE AC & PARKING! Exceptional condo w/peek-a-boo OV - res. guaranteed into 2027
Res. into 2027 GUARANTEED. Peek-a-boo OV from the large lanai. FREE DUAL AC! FREE PARKING! CA King w/purple mattress + queen sofabed in LR (4pp max.). Well stocked kitchen with all the appliances you will need. 55" smart TV in both LR &BR. Laundry in unit. Dual pane...
Village Manor A21, 2nd Floor, End Unit, Coconut Grove, Ocean Views!
Coconut Grove Apartment, Village Manor #A21. Just steps from the coastal bike path, walk to the beach, shops and grocery stores. Ocean, Mountain and Royal Coconut Grove views from the lanai. Accommodates up to 4 guests, including children and infants.Waipouli, Kapa'a,...
Oceanview 2 Bdrm/2 Bath - KAN114 -1st floor Gorgeous / Upgraded Condo
Kanai A Nalu ocean view condo #114 is a stunning vacation rental that has been remodeled with exquisite attention to detail. From high-end materials, finishes, and furniture to beautiful doors and light fixtures, every detail has been meticulously thought through to...
Diamondhead & Ocean View ISLAND COLONY, Central location Walk to the beach, AC
Waikiki Central Location, Studio on 33rd Floor with stunning Diamondhead and Ocean view. A queen bed and single-sized sofa bed accommodating up to three persons. There also is an air mattress for you to use when needed. With AC, Wifi and quite spacious lanai. Blackout...
KM 114 2BD Oceanfront Condo w Ocean Views AC Pool
Kauhale Makai 114 Ground Floor 2Bedroom, 2Bathroom Condo with Ocean Views, Pool, and Hot Tub. Just Steps to the Ocean for a Fun Family Winter Vacation FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale...
Oceanfront, walk to shops and restaurants
Hawaii Tax ID: TA-091-878-1952-01TMK: 390080030022Stay in this 2 bedroom Hale Kai O'Kihei 305 unit and enjoy amazing ocean views and the convenience of being close to shops and restaurants. This property is perfect for a few couples or a family with 2 bedrooms and 2...
The Perfect Location in Waikiki 2 mins walk to Waikiki Beach
Legally permitted rental -134 Kapahulu Ave 719Honolulu, HI 96815A Great Studio kitchen unit at theWaikiki Grand Hotel®Just a couple of minutes' walk to theWaikiki Beach and close to all shops andawesome restaurants in town.The brand new comfortable 14"Queen memory foam...
Waikiki Marina & Ocean Views! Easy Walk to Beach! Washlet, Kitchen, AC, Wi-Fi
Ilikai Marina #590 – 1765 Ala Moana Blvd.Relax in this newly furnished "beachy contemporary" 1-bedroom and take in beautiful views of the ocean and yacht harbor.CONSTRUCTION NOTICE: Due to emergency building exterior spalling repairs, unit lanai will be closed from...
Kihei Bay Vista B 203- One bedroom One Bathroom quiet garden view
Kihei Bay Vista is a low rise island style complex across from a long sandy stretch of beach. The beach is perfect for walks, sunset watching or just relaxing. At certain times it is a popular spot to watch the kite surfers ride the waves and sail through the air! The...
Golf course adjacent condo with furnished balcony, pool & fast WiFi
Waikoloa Villas H203Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in ocean and golf course views from the covered and furnished balcony of this two-story condo in Waikoloa...
Ground Floor Ease+Tropical View! Full Kitchen, Lanai, Flat Screens+WiFi–Kiahuna 2051
Merging a tropical vibe with ground floor ease, this 690sf suite features floor-to-ceiling sliders that bring the beauty of fruit trees and flowers into the casual living area. Homey touches include a full kitchen and furnished lanai for “at home” dining and relaxing,...
Hawaiian inspired 4th floor condo in Kaanapali
Maui Kaanapali Villas A420 is a 4th-floor studio that offers central A/C, high-speed Wi-Fi, and a private lanai. This resort has elevators. This condo can accommodate up to 5 guests. The main area features 2 queen-size beds. The spacious bathroom includes an updated,...
🌴Lovely cooler elevation condo with ocean views. Well equipped.🌴
Set in the heart of Kona coffee country (Holualoa) and surrounded by coffee farms and plantations is Kona Coffee Villas. This 2-bedroom, 2-bath condo offers ocean views and resort amenities including:Heated Swimming PoolTennis CourtFull-size Basketball CourtGuest...
Banyan Tree 404:Top Floor DIRECT oceanfront condo
Knutson & Associates is very proud to represent Banyan Tree 404, a top floor condo in a secure and private building with an elevator, pool, spa and barbecue!Full length views of the ocean from both the living room and bedroom of this stunning unit. The bedroom includes...
Tropical haven with pool, hot tub, grills & window AC - walk to beach
Maui Kamaole I112Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Walk just minutes to shimmering beaches from this condo, ideally in the Maui Kamaole complex. Enjoy views of the...
Ilikai 1418 2 Bed Room Luxury Remodel Ocean / Lagoon Views
OCEAN / LAGOON VIEWS! STEPS TO WAIKIKI BEACH. 2 bedroom, 2 bathrooms, two 120 sq. ft lanais, 1,000 interior sq. ft. Kg bed, 2 double beds, Qn sofa bed. Walking distance to parks, shopping mall, restaurants, shops, buses, rental cars, parks.The Ilikai Suites are located...
Pili Mai 10F - Vacation Rental in Poipu
Pili Mai 10FOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for a family beach vacation, this sunny and inviting, golf course-adjacent condo offers everything you need for the...
Family Condo!!! Close to BLACK ROCK 2BR/1BA Ocean View - K 112 ground floor
The perfect family friendly Maui beach condo. Come as couple, or bring the family, even the extended family!!Primary bedroom sleeps two, while the back bedroom has two twin-over-full bunkbeds that can sleep all the kids.Large banquette dining area can accommodate 8 so...
Spacious, stylish oceanfront studio
Noelani 118 is a Studio condo located on the ground-floor featuring amenities such as panoramic ocean views, an oceanfront lanai, and air conditioning. The condo can accommodate up to 3 guests with a queen-size bed and a queen sleeper sofa in the living room. The...
Wailua Bay View 215 Oceanfront condo
Welcome to this delightful condo in Kapaʻa. This cozy space features 1 bedroom with a comfortable king bed and air conditioning in the bedroom, perfect for a relaxing stay. Enjoy the convenience of WiFi, a hair dryer, and a washing machine during your visit. The...
🌺 Immaculate 3-BEDROOM 2-BATH Unit in KO Olina KAI! 🏖️
IMMACULATE CONDO IN KO OLINA KAI! 🌺 🏡 This beautiful property features 3 bedrooms and 2 bathrooms, a full kitchen, Spacious living and dining areas and, of course, a nice lanai (balcony) so you can enjoy your morning coffee or watch a beautiful Hawaiian Sunset! 🌅...
29th Corner 1 BR Great Panoramic Ocean View!! Pacific Monarch
Enjoy the lovely Hawaiian breeze in this high-floor 1-bedroom unit. Within walking distance to Waikiki's finest destinations." The Pacific Monarch building is centrally located in Waikiki, with a great variety of entertainment and dining options nearly at its doorsteps....
Maui Kamaole F-204 | Large Private Balcony!
Welcome to Maui Kamaole F-204, your well-equipped and well-located address on the western shore of the beautiful island of Maui. This two-bedroom, two-bath spacious second floor condo is located in the first-class Maui Kamaole resort, which is situated on 23 acres of...
Maui Kamaole J214: Remodeled 2 bedroom condo with Ocean views, sleeps 6
Stunning remodel completed at the end of 2018 in this two-bedroom ocean-view condo at Maui Kamaole. This beautiful remodel can be most enjoyed in the kitchen and two full bathrooms. The furnishings in this condo are a mixture of tropical and modern and create a feeling...
Fully modernized 11th floor studio at The Palms
Situated just below the penthouse, this fully furnished, newly renovated studio features a preferred layout with 2 queen sized beds and open lanai.Fully modernized 10th floor studio at The Palms Hotel on the West side of Waikiki - Close to Fort DeRussey, Ala Moana...
Superior, remodeled, Oceanfront two bedroom 2.5 bath low rise, AC, pool.
Aloha, and welcome to this picture-perfect Puamana home. #43-2 is an ideal oceanfront location inside the beautiful protected Puamana grounds, unharmed by the Lahaina fire. This home has just recently been updated and features numerous improvements. Brand new, cool &...
Whaler 714 Studio Close To It All
Welcome to Whaler 714, your ideal Kaanapali Maui vacation retreat. Perfect for the solo traveler, couple, friends, or small family, this beautifully upgraded ocean view studio on the 7th floor offers stunning views of Kaanapali Beach and unforgettable sunset beach...
Updated home with pool, patio, deck, WiFi, washer/dryer, & gas grill
Keauhou Surf & Racquet 3-201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled in the resort-style gated Keauhou-Kona Surf & Racquet Club community, this condo has been...
Stargazing Mountainside Cottage by Pristine Beaches
This beautiful, breezy, and quiet cottage in the stunning Makaha Valley offers a wonderful opportunity for you to immerse in Hawaii's peaceful nature. Surrounded by gorgeous ridges and valley, you will enjoy amazing views all around. The backyard patio is perfect for...
Tropical Gem Near Waikiki Beach 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...
Kahana Manor 502 Remodeled 2 bedroom 2 bath Oceanview
Book with us and come to Maui to explore everything we have to offer!Portable ACs installed in both bedrooms (not pictured).This remodeled 2-bedroom 2 bath Kahana Manor condominium has everything you need to relax in Maui. The granite and stainless-steel kitchen is...
Ocean View Room, Spectacular Beachfront Resort, 4 pools, Restaurants on site
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful fifth floor unit with amazing views of the ocean and pools. Comfortable King bed and Chaise Lounge.The Outrigger Kauai Beach Resort and Spa is a beautiful Hawaiian...
🏖️Concierge Included | Ground Floor with Ocean Views | vrKCV
vrKCV - Sea Village 2106, Professionally Managed by Kona Coast VacationsRelaxed Ocean-View Escape Near Downtown Kailua-KonaPerfect for couples and families, this bright and breezy two-bedroom, two-bath condo offers a comfortable home base on the beautiful Big Island....
KR506-Ocean View - Beachfront Resort - Great Winter Whale Watching!
Located on the fifth floor, Kealia unit 506 offers a spacious and relaxing retreat. The master bedroom boasts a king-size bed as well as a lofted day bed in the alcove, providing ample sleeping space. Step out onto the private lanai to take in stunning ocean views and...