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.
KAS 8409 Ocean Views from this Freshly Updated 2BD Kihei Maui Condo
Kamaole Sands 8409 NEW LISTING Enjoy Ocean Views from this 2Bedroom, 2Bathroom Condo, Conveniently Located Within Walking Distance to the Beach! FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale...
Penthouse Condo with Ocean & Diamond Head Views at The Windsor
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.*This property is new to our inventory, so reviews are on the way! Rest assured, it has been carefully...
Pool House Studio with King Bed – Poolside Retreat
Stay poolside in this spacious 484 sq. ft. studio featuring a king bed, a sofa bed, and a convenient wet bar. With modern amenities like air conditioning, free Wi-Fi, and a flat-screen TV, this studio is perfect for a laid-back and refreshing escape.Key Features: •...
Coconut Plantation 1100-2: Elegant 3BR Condo Near Beach & Golf
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Coconut Plantation 1100-2 by...
Best 3 bed villa by the beach
Summary:Treat yourself to vacation of a lifetime in this tastefully remodeled villa that opens to beautiful sunsets every night. Located across the lake (short walk) from golf, shopping, coffee, beach. King bed on 1st floor with no steps. Oversized main with king bed,...
Experience Unparalleled Luxury in a Mountain View Studio at Marriott’s Ko Olina!
Indulge in a serene escape at Marriott’s Ko Olina Beach Club, where your villa is surrounded by crystal-clear waters and a breathtaking lagoon. Nestled within a lush, gated community on the stunning island of Oahu, our premium vacation ownership resort offers the...
Walk to Beach from Lux Condo w/Hilton Pool Pass
When you stay at our 3/2 nestled between the Hilton and Marriot, you're steps to the beach and a 5-10 minute walk to shopping, groceries, beach-front dining, a luau, a movie theatre and ancient ruins. The location simply does not get better in this resort area!Located...
Breathtaking Location! 2 Modish Units, Near Hulihee Palace, Kona Snorkel Tours!
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
The Westin Nanea Ocean Villas, Ka'anapali
Spread out with the whole family in this spacious two-bedroom suite. Zipline across jungle, snorkel with the dolphins, and rediscover your best self in year-round-gorgeous Maui. Jeweled with spectacular beaches and adorned with gnarled volcanic rock, Maui is famed for...
Paradise resort home in Ko Olina Coconut Plantation
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Lahaina Shores 533: Oceanfront Bliss & Whale Watching Views
* NEW PROMO: Stay 5 or more nights Sep 27- Oct 31, get 1 FREE! Lahaina Shores 533 – Oceanfront Romance & Unforgettable ViewsPerched on the 5th floor of the beloved Lahaina Shores Beach Resort, this beautifully renovated studio offers an unbeatable combination of...
Serene Makaha Retreat
Discover serenity at our home. 3 beds, 2 baths, steps from world class Makaha beaches. Enjoy a spacious retreat with a fully equipped kitchen, outdoor BBQ, and scenic views. Nearby hiking, golf, and local attractions. Safe and convenient. Your Hawaiian escape awaits!
Marriott's Waikoloa Village Condo 1 Bedroom, 2 Bathroom
Marriott's Waikoloa Ocean Club is a paradise in paradise, where the ancient love story between the goddess Pele and Kamapuaʻa comes to life and inspires every detail. From the island's lush green flora and pristine waterfalls to its fiery red volcanos and black lava...
Cozy studio condo with AC and WiFi in charming Koloa/ Poipu
Nestled in Koloa, this delightful condo is a tranquil oasis for guests seeking a serene getaway. With a cozy bedroom and a well-equipped bathroom featuring a shower and hair dryer, this gorgeous property provides all the comforts of home. Enjoy modern amenities like...
Makani A Kai A4 - Oceanfront Walkout - 15 feet from beach
Oceanfront Escape at Makani A Kai A4 – Maalaea, Maui. Welcome to your own slice of paradise on Maui's southern shore! This 1B/1B walkout sits on the beach in Maalaea, offering breathtaking ocean views, and private access to 3 miles of the secluded sandy Sugar beach....
Royal Kahana Maui 605 Ocean View Studio
- 6th floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry, kitchen, bathroom and...
Comfortable Studio for 2 | Full Kitchenette
Spend your next vacation discovering the beautiful beaches and stunning hikes in Oahu! Our comfortable Studio for 2 is conveniently located close to numerous shops and restaurants! Soak up the sun on Waikiki Beach, only 7 minutes away. We think you'll love:• Studio...
Kanaloa at Kona Partial Ocean View 2 Bedroom
- Condos located on 1st or 3rd floors- Private balcony with wet bar- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Master bedroom with 1 king bed or 1 queen bed and private bathroom with...
Oceanfront Suite with Private Balcony at OUTRIGGER Waikiki Beach Resort!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! With comfortable amenities and authentic Hawaiian hospitality, you'll have everything...
Tropical Tranquility and Sunset Views! Maui Vista 2223
Tropical Tranquility and Sunset ViewsWelcome to your perfect Maui getaway! Nestled in the heart of South Kihei in the desirable Maui Vista Resort, this beautifully renovated condo offers the ideal blend of comfort, convenience, and island charm. Whether you’re seeking...
1 Bedroom Condo-Princeville, Kauai-Family Friendly!
Perched above the sparkling waters of Hanalei Bay, this resort offers families a front-row seat to some of Princeville’s most awe-inspiring natural beauty—from the dramatic Na Pali Cliffs and iconic Bali Hai Mountain to cascading waterfalls, golden beaches, and palm...
Moani Heights 13 Four Bedroom
Rest and recharge in this luxurious four-bedroom, four-bath island retreat, where indoor comfort meets stunning outdoor living. The open-concept kitchen and living area flow seamlessly onto a spacious, furnished lanai, perfect for enjoying the coastal breeze. Step...
Christmas Week Dec 19-26th at The Westin Nanea ocean resort on Kaanapali beach
Special week December 19th - 26th!!!!!Experience Nanea - a state of relaxation and repose - firsthand. Resort blends a top-notch vacation experience with the authentic history and culture of Hawaii. Amenities include a 10,000 square foot lagoon style pool with a upper...
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
After a hot day at the beach, relax at Ke Kīhāpai Bed & Breakfast at the 2400 foot elevation with unobstructed views of our dormant volcano, Haleakalā. Breathe the fresh air with an upcountry view of town, the north shore of Maui and Kahālāwai (West Maui...
Golf Villas Ocean View 1 Bedroom at The Kapalua Villas Maui, Full Kitchen
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...
Escape to Paradise! 2 Serene Units, Pool, 3 Restaurants, Right on Beach!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Oceanfront Serenity – 4th Floor Dream at Lahaina Shores
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE!NEW LISTING: Lahaina Shores 421 - Many upgrades!Lahaina Shores is a charming boutique resort located directly on the ocean with a beautiful view of the neighboring island of Lanai. Unit 421...
The Westin Kāanapali Ocean Resort/ 2-Bedroom
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour...
Wyndham Royal Sea Cliff | 2BR/2BA King Balc Suite
Summary:Nearby Pu‘uhonua o Hōnaunau, an ancient sanctuary whose name means "the place of refuge," could easily describe this resort. Oceanfront, modern, and conveniently tucked outside Kailua-Kona, tranquility reigns. It’s the ideal home-base for all of your island...
Kaia Villa, at Turtle Bay - Modern North Shore Oahu Retreat w/Lanai & Golf Views
Special Launch offer-First 3 guest receive 20% off their stayDebuting October 2025. Kaia Villa offers a newly renovated stay on Oahu's famous North Shore. Set within Turtle Bay Resort , This property has been thoughtfully transformed into a stylish island retreat...
Aston at the Whaler on Kaanapali Beach #623
The expansive floor plan creates a very spacious two-bedroom, two-bath condo. This well-appointed condo has been completely remodeled with top-of-the-line finishes and furnishings. The lanai wraps around from the mountainside to the center courtyard and offers sweeping...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Find peace and tranquility in your very own...
Pool House with 2Queen Beds – Poolside Comfort
Enjoy a relaxing poolside retreat in this 484 sq. ft. studio featuring two queen beds and a wet bar. With air conditioning, free Wi-Fi, and modern comforts, this studio provides a perfect blend of convenience and luxury for your stay.Key Features: • Design-Centric...
Royal Sea Cliff Kona Garden View 2 Bedroom
Garden View 2 Bedroom 2 Bath- Condos located on 1st, 4th and 5th floors- Private balcony- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, cookware and tableware- Master bedroom with 1 king bed and private bathroom with...
The Heights Hideaway
About this spaceCute & cozy two-bedroom apartment on the ground level of a single-family home. Private entrance. Includes a full kitchen with appliances and a private bathroom with a shower.The spaceYour space is located on the ground level with a private entrance.You...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Stay at Kailua Beachside by Gather, a...
Ocean View Magic Sands Beach Condo in Kailua Kona Hawaii
Aloha and E Komo Mai!Our Oceanside Magic Sands Getaway is located in the Heart of Kailua Kona in the White Sands Village of Alií Drive on the Big Island of Hawaii. Just steps away from the World Famous La'aloa Beach Park also known as Magic Sand Beach. We offer a...
Island Surf 510 | Water Views, Across from the Beach + In the Heart of Kihei!
Escape to the serene paradise of Island Surf 510C, a cozy tropical condo nestled in the heart of Kihei, Hawaii. This charming vacation rental offers a tranquil retreat for up to 4 guests, boasting 2 spacious bedrooms and 2 bathrooms all conveniently situated on one...
Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-207
Makena Surf B-208Welcome to Makena Surf B-208, a luxurious oceanfront condo that combines the serenity of beachfront living with upscale finishes and exceptional comfort. Located in the prestigious Makena Surf Resort, this second-floor unit boasts panoramic views of the...
Konishiki Beachhouse: Luxury 4BR Oceanfront Home w/ Private Pool, Beach Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Konishiki Beachhouse 4BD by Gather,...
Kapalua Golf Villas Ocean View 2 Bedroom
Golf Villas Ocean View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and bathroom- Guest bedroom with 2 twin beds;...
Butterfly House: Beautiful Ali'i Drive Home with Ocean Views!
Incredible Modern Alii Drive Home with Ocean Views! A beautifully renovated home right across Kahalu'u Beach on the historic Ali’i Drive.Modern finishes throughout. 2 Master bedrooms with 2 full baths. Modern fixtures in all areas of the home.Stay cool with ceiling...
2/2 Modern & Elegant Penthouse Oceanfront Vistas
Summary:Spacious and elegant. Completely remodeled in December 2022, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is...
Princeville Kauai 2 bedroom 2 Bath Sleeps 5
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This premier complex, perched on a verdant bluff, provides a paved path to Hideaways Beach, where you can snorkel, swim and soak up the sun. On-site amenities include a restaurant,...
Rare Lahaina Shores Oceanfront Corner Unit - Stunning Island Views
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE! Lahaina Shores 601 – Oceanfront Elegance with Panoramic ViewsDiscover the magic of Maui from Lahaina Shores, a charming boutique resort set directly on the ocean in the heart of Lahaina....
Beautiful Apartment in Hawaii
Newly refurbished apartment, attached to our family house. Separate entrance. The apartment is located in the historic and very authentic neighborhood of Captain Cook, 2 minutes drive to the beginning of the famous Captain Cook monument trail, and 15 minutes drive to...
Dlx 1 br Waikiki Condo Rental...Sleeps 5/Lovely views. Waikiki Beach!
Enjoy your own 1-BR Oahu condo rental - just a short stroll to Famous Waikiki Beach & and ideally located near world-famous Diamond Head. On the 'quiet side' of Waikiki. Your 1-bedoom Waikiki Beach Condo vacation getaway is appointed in a cool Hawaiian-tropical decor,...
Maui Resort Rentals: Honua Kai Konea 504 – Luxurious 2BR w/ Beautiful Partial Ocean & Mountain Views!
Konea 504 is a luxurious two-bedroom suite, offering guests the best of both worlds, beautiful partial ocean and mountain views right from the comfort of your spacious private lanai. Located in the very first two-bedroom stack from the oceanfront column, your group will...
Hawaiian Oasis w/ Private Pool, 2 King Suites & Sunset Views!
Discover true Aloha at this stunning private 3-bedroom oasis, where island charm meets luxury. Behind a gated front entry, this beautifully designed home features soaring vaulted ceilings, dramatic lava rock wall & 2 king suites and a chefs kitchen, offering a serene...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, Premier 5th Floor Interior Courtyard Offering w/ Stunning Ocean Views!
This tandem 3BR/3BA pairing is comprised of two fantastic 5th-floor oceanview suites located directly next door to each other. Both suites overlook the lush resort grounds and pools of the Hokulani Tower interior courtyard and provide stunning full ocean views.Gather,...