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.
6BR/6BA Luxury Villa w Pool, A/C, Walk to Beach!
Perfect for large families, wedding groups, or multigenerational getaways, this setup offers two side-by-side first-floor villas in Po‘ipu’s newest luxury complex—just a 5-minute walk to top-rated beaches and the Grand Hyatt. With 6 bedrooms, 6 full bathrooms, 2 fully...
Kaanapali Alii 3812 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Kaanapali Alii 381 is a beautifully appointed one-bedroom ocean-view residence with a fully enclosed den that serves as a second bedroom. From the living room,...
Kaanapali Alii 41062 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Welcome to Kaanapali Alii 4106, a stunning two-bedroom platinum-rated condo with an unparalleled ocean view from its corner location. This inviting space is...
Kaanapali Alii 41022 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Kaanapali Alii 4102 is a platinum-rated one-bedroom ocean-view condo with a fully enclosed den that comfortably serves as a second bedroom. Located on the 10th...
Kaanapali Alii 31122 Bedrooms | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Kaanapali Alii 3112 is a platinum-rated one-bedroom condo with a fully enclosed den that comfortably serves as a second bedroom. Unique furnishings and...
Kaanapali Alii 31022 Bedrooms | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 3102, an elegant one-bedroom ocean-view condo with a fully enclosed den that serves as a second bedroom. This spacious retreat...
Kaanapali Alii 21012 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Kaanapali Alii 2101 is a luxurious platinum-rated one-bedroom condo, with a fully enclosed den that comfortably serves as a second bedroom. Located within the...
Ka’anapali Alii 4932 Bedroom | 2 Bathrooms | Sleeps 6 | Mountain View________________________________________Escape to paradise in this stunning 1,513 square foot one-bedroom mountain view condo with a fully enclosed den that comfortably serves as a second bedroom....
Kaanapali Alii 4832 Bedrooms | 2 Bathrooms | Sleeps 6 | Mountain View________________________________________Kaanapali Alii 483 is a beautifully appointed one-bedroom mountain view condo with a fully enclosed den that comfortably serves as a second bedroom. Start your...
Kaanapali Alii 4332 Bedroom | 2 Bathrooms | Sleeps 6 | Garden View________________________________________Kaanapali Alii 433 is beautiful one-bedroom garden view condo with a fully enclosed den that comfortably serves as a second bedroom. Spanning an impressive 1,513...
Kaanapali Alii 3842 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________The phrase “modern elegance” perfectly describes platinum-rated Kaanapali Alii 384. Clean white walls, tiled floors, and cream-colored furnishings are paired with...
Kaanapali Alii 3832 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 383, a beautifully renovated two-bedroom ocean-view residence that serves as the perfect gathering place for your Hawaiian getaway. The...
Kaanapali Alii 3712 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Kaanapali Alii 371 is a premier one-bedroom ocean-view residence with a fully enclosed den that functions as a second bedroom. Located on the seventh floor, this...
Ka’anapali Alii 3643 Bedrooms | 2 Bathrooms | Sleeps 7 | Ocean View________________________________________Welcome to Kaanapali Alii 364, a stunning 2-bedroom, ocean-view residence, with a fully enclosed den that comfortably serves as a third bedroom. This sixth-floor...
Kaanapali Alii 3612 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________This beautiful platinum-rated sixth-floor Maui condo is a serene escape, featuring one-bedroom with a fully enclosed den that comfortably serves as a second...
Kaanapali Alii 3222 Bedrooms | 2 Bathrooms | Sleeps 4 | Garden View________________________________________Welcome to Kaanapali Alii 322, a one-bedroom mountain view condo with a fully enclosed den that comfortably serves as a second bedroom. This stunning residence...
Kaanapali Alii 2962 Bedrooms | 2 Bathrooms | Sleeps 6 | Mountain View________________________________________Discover the perfect Hawaiian escape at Kaanapali Alii 296, a stunning two-bedroom mountain view condo on the ninth floor that offers a blend of luxury and...
Kaanapali Alii 2842 Bedrooms | 2 Bathrooms | Sleeps 4 | Mountain View________________________________________Welcome to Kaanapali Alii 284, a stunning one-bedroom mountain view condo, with a fully enclosed den that comfortably serves as a second bedroom. This 8th-floor...
Kaanapali Alii 2462 Bedroom | 2 Bathrooms | Sleeps 6 | Garden View________________________________________Kaanapali Alii 246 was designed for entertaining! This two-bedroom garden view condo is positioned in the corner of the resort, with most of the living room and...
Ka’anapali Alii 1633 Bedrooms | 2 Bathrooms | Sleeps 9 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 163, an inviting 2-bedroom, partial ocean-view residence, with a fully enclosed den that comfortably serves as a third bedroom....
Ground floor just steps away from sandy beaches
Hono Kai A4 is a ground-floor, 1-bedroom, 1-bathroom condo that offers a portable A/C in the bedroom and ceiling fans throughout, which helps to keep you cool. Unit A4 can accommodate up to 4 guests. The bedroom presents a queen-size bed, while a queen-size sofa sleeper...
Updated oceanfront gem @ Sugar Beach Resort, Central AC, NO Booking fees!
Welcome to Sugar Beach 518. This updated oceanfront 1 bedroom, 1 bathroom condo can accommodate 4 people. Enjoy ocean views throughout this unit and from your private lanai. Feel right at home with everything from central AC to in unit washer/dryer, and essentials....
Elegant Poolside Penthouse with Private Elevator
Summary:F300 | TA-018-220-0320-02Experience elegance in our Poipu Penthouse Villa, boasting luxury designer furnishings and gourmet kitchens. Stay cool with central A/C and enjoy elevator access directly into F300. Relax amidst tropical views and exceptional luxury in...
3BR I Spacious Poolside Villa | Gourmet Kitchen, Lanai
Summary:D211 | TA-018-220-0320-02Welcome to your tropical retreat in sunny Poipu! Villa D211 is a luxurious 3-bedroom, 3-bathroom poolside villa offering 1,600 sq ft of thoughtfully designed indoor-outdoor living. Ideal for families or groups, this elegant space blends...
3BR I Poolside Ground-Floor Villa |Walk to Beach|Hot Tub
Summary:E110 | TA-120-625-1520-01Walk to the best beaches on Kauai! In a tranquil setting surrounded by lush tropical landscaping, unwind in the pool, soak in the hot tub, work up a sweat in the fitness center or on the tennis courts, walk to multiple beautiful beaches...
3BR I Poolside Lanai Villa l Parking, Sunset View
Summary:F211 | TA-018-220-0320-02Walk to Kauai’s top beaches from Villa F211, surrounded by lush tropical landscaping in the heart of Poipu. Relax in the resort-style pool or waterfall hot tub, stay active at the fitness center or tennis courts, and return to your...
3BR I Luxury in Paradise l Beaches, Golf, Shopping
Summary:B211 |TA-018-220-0320-02Experience luxury and comfort in Villa B211 – a beautifully designed 3-bedroom, 3-bathroom retreat with 1,600 sq ft of living space and a 400 sq ft private lanai – Relax in the master suite with a soaking tub and dual-head shower –...
3BR I Fabulous Villa | Walk to Poipu Beach, A/C
Summary:C211 | TA-018-220-0320-02Welcome to your luxurious Poipu Villa, tucked within the renowned Poipu Kai Resort. This spacious 1,600 sq ft retreat features a gourmet kitchen, upscale furnishings, and coveted air conditioning. Embrace the tranquility of island life...
3BR I Luxury Poolside Villa | Stunning Ocean View, Lanai
Summary:D210 | TA-019-101-6960-01Enjoy tropical views and elevated comfort at Villa D210, part of the Poolside Villas at Poipu Kai. This spacious 3-bedroom retreat features an open layout, designer furnishings, central A/C, and a fully equipped gourmet kitchen. Dine...
3BR I Luxury Villa l Designer Furnishings, Central A/C
Summary:E111 | TA-167-599-1040-01Experience refined island living at Villa E111, a luxurious Poolside Villa in the heart of Poipu. Outfitted with designer furnishings, a gourmet kitchen, central A/C, and in-unit laundry, this spacious retreat offers all the comforts of...
Blue Kauai Hale - Peaceful Multi-Level Home in Princeville
Relax with the whole family at this peaceful oasis. Blue Kauai Hale is the perfect base camp from which to explore and adventure on Kauai, then return home to soak in the hot tub and create more memories over a gourmet meal.Recently remodeled throughout with 4 bedrooms...
Mau Loa Hale: Perfect Location 5 Acres Walk to Bch! Open concept! Breeze & Views
Welcome to Mau Loa Hale, a private island-style retreat on five acres between the Koʻolau Mountains and the Pacific. Here, dramatic ridgelines meet ocean breezes, creating a peaceful escape where you can spread out, recharge, and experience Oʻahu at a slower rhythm....
Romantic cottage with stunning ocean and mountain views in Captain Cook, HI
Enjoy spectacular views of Kealakekua bay in the newly built Coffee Cottage in Captain Cook, Hawaii! Situated amongst the coffee trees at a pleasant 1350 ft. elevation, it’s a perfect temperature year round. Stretch out in the California king bed and check out that...
🏖️New Listing! | Beautiful Townhome | Great Location | Concierge Included!
vrKCV - Kulalani at Mauna Lani 205 - Professionally managed by Kona Coast VacationsSecluded Kulalani Villa in the Mauna Lani ResortYour perfect vacation in a tranquil tropical oasis! Kulalani at Mauna Lani is a private gated community of quiet luxury townhomes,...
Maui Resort Rentals: Honua Kai Hokulani 930 - Extra Large 1BR w/ 9th Floor Mountain Vistas!
Hokulani 930 is a luxurious 1BR/1BA mountain view suite that enjoys expansive vistas of the lush West Maui Mountains from its impressive 9th-floor vantage point. This oversized suite is ideally suited for small families and couples who will relish the spacious 765 sq ft...
Remodeled 1bd, stunning sunsets & views
Nestled on the 3rd floor, Valley Isle 305 is a charming 1-bedroom, 1-bathroom condo that offers direct ocean views and ceiling fans throughout. This resort has elevators for easy access. Unit 305 can accommodate up to 4 guests. The master bedroom features a king-size...
Ocean Front HOME on the Big Island! Lookout and view Heaven - Maka'Ala Lani!!
Located in a quiet neighborhood in beautiful Hawaiian Paradise Park on the pahoehoe lava rocks above the blue Pacific Ocean. Wake up to the most beautiful sunrises and fall asleep to the lull of the ocean waves. Sit back and enjoy the ocean while you BBQ. Later go for a...
Whales and great reviews! Royal Kahana 2 Bd/2Ba! Hotel zoned Safe to Book!
We welcome and need you to visit our beautiful island. We thank you for your support and welcome you! This property is hotel zoned which means that short term rentals will continue to be legal rentals at this property. The apartment zoned properties are proposed to be...
Tropical apartment with amazing water views & rooftop pool - prime location
Marina Views Studio - Ilikai, 941Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha is abundant at this immaculate Honolulu studio! Centrally located, you can shop, dine, and sit...
Hale Leilani: Kukui'ula Plantation Villa with Ocean View & Pool
Luxuriously appointed, supremely spacious, and overflowing with tropical charm, this stunning new plantation-inspired home in Kukui'ula is superlative in every way. The entire property—poetically christened Hale Leilani—embodies the most appealing aspects of a modern...
Malia Ohana Hale - Upscale Hawaiiana Townhome
Plantations at Princeville #1022, now offered through Makana Kauai Properties. Welcome to Malia Ohana Hale, this is paradise where you will find our luxurious plantation-style top floor 3 spacious bedrooms and 3 full bathroom condo welcoming and relaxing, with all the...
Ocean View Poipu Sands Condo in sunny Poipu
Beautifully appointed 1 bedroom, 1.5 bath ocean view condo offers the Kauai experience you've been looking for! Highly sought after ground floor unit provides abundant open space and direct access to the barbecue grill and pool. Plenty of free parking close to the condo...
Maui Resort Rentals: The Whaler 563 - Gorgeous 5th Floor Studio w/ Fantastic Pacific Ocean Views!
Enjoy gorgeous views of the Pacific Ocean and Maui's neighboring island Lanai from this luxurious 5th-floor studio suite at the Whaler in the heart of Kaanapali Beach.Beautifully upgraded, suite 563 offers a spacious 500+ sq. ft. living interior that can comfortably...
5 Minutes to the Beach! Oahu Ocean View + Family retreat
☆☆☆ Why guests LOVE our home? Why guests find it such a great VALUE?- Free parking for 5 cars (save $40–$100/car nightly)- Private SPA & BBQ in backyard, full kitchen to cut dining costs, - Spacious single-story for large family with senior and kids, 3 bedroom, 9 beds...
Take advantage of our introductory rates! Your Hawaii home is ready for your arrival
Take advantage of our introductory rates! Your Hawaii home is ready for your arrival.If you're looking for the perfect place to spend your next (or first!) Hawaiian vacation, then you need look no further than this light and airy two bedroom 2.5 bath townhome that can...
Upscale Oceanfront Penthouse Vistas
Summary:Full remodel and decorated ourfitted with all new furnishings. This elegant 2-bedroom, 2-bath condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei at Menehune Shores resort, all of Maui is within reach. Beach chairs,...
Maui Gov’t Approved Short Term Rental. We are the owners (Barry Travers and Rhonda Anderson) of Mahana 118 and we own several Maui properties with hundreds of 5 Star reviews for our properties as we provide the ultimate guest experience! Mahana 118 is an AMAZING...
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
• Oceanfront• Split A/C units• King bed• Remolded June 2023• Beach access from condo complexFully remodeled in June 2023, unit 218 is bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei welcomes you! This second floor condo is luxurious...
** 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...
Oceanview Kihei Akahi D210: Updated 1BR/1BA, Perfect for everyone!
Unit D-201 has been completely remodelled and refurnished with modern, beachy decor. Fully renovated kitchen is wide open and includes views from the large, stone island and is fully equipped for the home chef! Dining table for 4 inside is perfect for game night....