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.
Oceanfront 2 BD Villa with Endless Ocean Views
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! We welcome you to stay in our nicely upgraded condo just a short walk from the beautiful beaches located in Kapalua. Relax and enjoy your Maui vacation at Kapalua Bay Villa 35G4. A gorgeous 2...
Sunset Beach House in paradise! Inquire for special 30 day rates!
Unit B1 is Ocean Front at Sunset Hale. Newly updated 2-bedroom 2.5-bath ground floor oceanfront unit. The Kitchen, living room and dining area are all facing out to beautiful ocean and sunset views! Enjoy these views from inside or hang out on the porch. Bedroom (1) has...
100% Renovated Luxury Condo with Ocean/Jungle/Mountain/Waterfall Views
Welcome to our ocean, jungle, mountain/waterfall view Princeville condo on Kauai's spectacular North Shore, one of the most beautiful and peaceful locations on earth. The Princeville Resort area is known for its gorgeous beaches, world-class golf, top-notch surfing,...
Papakea RESORT! - RENOVATED unit, GROUND FLOOR & steps to BEACH, POOL & BBQn
PROFESSIONALLY RENOVATED AND DESIGNED FROM TOP TO BOTTOM and BRAND new FURNISHINGS FALL 2021This functional "C2 Studio" plan has a beautiful kitchen with cherry maple "soft close" cabinets, cream quartz countertops, glass backsplash, under mount cabinet lighting, LED...
Tropical Garden View at a Beach Front Property-Kihei Kai Unit 21
Condo #21 is a garden view unit located on the upper level. Enjoy the surrounding tropical foliage as you relax on the lanai. The kitchen has been beautifully remodeled and fully equipped with modern appliances, dishes and cookware. This condo will sleep 4 comfortably...
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...
Sea of Glass - Beachfront Luxury Property on Oahu's North Shore
30 day rentals availableSea of Glass is an architecturally stunning beachfront home on the North Shore of Oahu. The A-frame design is accentuated by windows that face Mount Ka’ala, the tallest mountain peak on the island to the south, and wall-to-wall sliding doors...
Professionally Decorated, Beachfront, Double Unit on the 18th floor.
Famed COLONY SURF condo on Oahu's 'Gold Coast' on the Diamond Head end of Waikiki. This romantic get-a-way is perfect for an unforgettable Hawaiian vacation. An extra large DIRECT OCEANFRONT 1,440 sq' condo with a 25' long panel of windows in the living room and 12' of...
Kihei Beach Retreat: Ocean Views and Sandy Feet!
Experience Maui's charm in our 2-bed, 2-bath condo, directly managed by us for a personal touch. Just steps from top beaches and snorkeling, with stunning ocean and West Maui Mountain views. Enjoy our resort-style amenities including a pool, hot tubs, game room, and...
Top floor condo with ocean & mountain views. Ask about last min discounts! <br>
Breathtaking ocean and majestic Haleakala mountain views. This is a highly sought after, beautifully updated two bedroom, two bathroom condo. The Maui Banyan is prime location - across the street from the soft sand of Kamaole Beach 2. This white sandy beach is perfect...
KBM Resorts | FREE CAR | Papakea | Oceanfront | 1-Bedroom Corner Unit with Unobstructed views! PKA-201
Oceanfront 1BR corner condo at Papakea with wraparound views, updated interiors, full kitchen, and private lanai. Enjoy pools, tennis, beach gear, and top snorkeling right outside your door.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with...
Marriott Waiohai Beach Club: luxury 2 bedroom on Poipu Beach oceanfront resort
Please choose a Friday through Sunday check-in and enjoy a seven-night stay.Thank you for choosing Dash Realty Group of Windermere, Florida. We are a registered Fla. Seller of Travel Ref. No. ST42435.Our rates reflect garden/island views. Ocean view/oceanfront villas...
Laule'a 5: Luxury Home w/ Infinity Pool, Spa & Stunning Views
Experience the luxury and natural beauty of Hawaii Island from the Residences of Laule’a #5, the newest development in the Mauna Lani Resort bringing a contemporary evolution to luxury resort living on the Kohala Coast. This stunning property is now accepting 30 day...
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
This very spacious ocean and pool view cottage has everything you need to truly relax andenjoy the serenity of Maui. Designed in a vintage Hawaiian theme with a modern twist, thisroom offers a unique tribute to the great Hawaiian Surfer, Duke Kahanamoku. The cottage...
Relax near Port of Hilo, charming Hakalau apartment
In this quaint Hawaiian village, our cozy home provides a peaceful escape during your upcoming trip. Imagine waking up to stunning water views and spending your days exploring the nearby attractions, such as the Port of Hilo, Coconut Island Park, and the breathtaking...
Kitchen and Bath Remodel! - Ocean Front - Central Air - Featured on Today Show
Major kitchen and two bathroom remodel Includes new appliances, granite countertops, custom stone and ceramic tile work. New leather sofa and loveseat. Owner-operated and continually updated! Excellent rental history and outstanding guest reviews.Unwind at this...
Maui Resort Rentals: Honua Kai Konea 713 - Stunning 7th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan
Konea 713 is among a class of the most sought after two bedroom floor plans at Honua Kai. What distinguishes this column in the Konea interior are the direct ocean views from virtually every interior vantage point of the suite. This premier two bedroom boasts a spacious...
Ocean View Kona Hideaway - Pool - Sleeps up to 8
The Kona Hideaway is a beautiful private one acre home... It has a 180 degree ocean view and lots of privacy. Pool , fruit orchard with mango , papaya ,orange grape fruit and much more .Also, ping pong , weight equipment and lots of beach chairs pool and beach toys and...
Kapalua Bay Villa 26G2 Gold Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- One level condo with 17 stairs between parking and front door- Travertine tile floors in living room, dining room, kitchen and bathroom and carpet in bedroom- Contemporary galley kitchen with granite counters and stainless steel...
Ehukai Beach Hale: Newly Remodeled Ocean View Home With A/C, Steps From Pipeline
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.This updated Haleiwa vacation rental home is...
Punahele Penthouse Luxury Condo
Punahele Penthouse Condo will fast become your favorite place to stay in Kailua-Kona! Punahele Penthouse is on the 7th (top) floor of the Kona Ali'i Condo Complex which is located in the heart of Kailua-Kona. You're within walking distance to many attractions,...
Sweeping ocean views from this beautiful top floor oceanfront unit!.
Recently remodeled, unit 602 has everything you need to enjoy your stay on Maui. When you stop gazing at the ocean you will notice the comfortable furnishings, colorful decor, well equipped kitchen with skylight and other amenities that guarantee our guests a wonderful...
Sealodge J7 - 2BR/2BA, 2nd Floor Prime End Unit, Spectacular Oceanfront Views
This idyllic getaway has the absolute best view of any other condo in the complex! It's a perfect place for family vacations, weddings and honeymoons. Spend your evenings lounging on the Lanai, watching the sunset along the Anini reef or relax inside on the punee...
Ocean Front Remodel I Menehune Shores 612
Enjoy expansive ocean views from the lanai at this bright and beautifully remodeled oceanfront one bedroom in the heart of Kihei town.Take a dip in the heated pool, or enjoy long walks and a swim at the protected beach just steps from the condo. The lanai is perfect for...
Nihi Kai 422 Summer & Fall Specials-Ocean Views, Five Star Ratings!
OFFERING DISCOUNTS FOR FALL 2025 !!This large 1400 square-foot, two-bedroom, single level, beautifully furnished condo has spectacular ocean views from the front lanai, living room, master bedroom, and kitchen. This third-floor unit has both ocean and mountain views and...
Nalu Hanalei - Stunning Hanalei Home Right by the Beach!
Nalu Hanalei – your ultimate Hawaiian getaway! Located just steps away from the world-renowned Hanalei Bay, this luxurious 4-bedroom, 3-bathroom property offers the perfect combination of comfort, convenience, and breathtaking ocean views.As soon as you step into this...
Sugar Beach #131: Front-row views, salty air & instant beach access—pure Maui!
Welcome to Sugar Beach Resort #131 – Your Ultimate Oceanfront Getaway in Maui! *Step into a world of relaxation and serenity at Sugar Beach Resort #131, a beautifully updated ground-floor condo with stunning ocean views and direct access to one of Maui’s most...
Maui Resort Rentals: Honua Kai Hokulani 526 - 1BR Suite w/ Lush West Maui Mountain Views
Hokulani 526 is a luxurious 5th-floor one-bedroom suite that offers beautiful vistas of The West Maui Mountains with their frequent afternoon rainbows. The suite is ideally suited for small families and couples who are looking for luxurious and spacious accommodations...
Family-friendly Waikoloa Beach Villa C2 next to pool; walk to beach!
Welcome to our island home-away-from-home! The Big Island is a truly special place with something for everyone – from beaches to walks and hikes to water activities, golf, shopping, and sight-seeing.Waikoloa Beach Villas is adjacent to the Queens and Kings Shops for...
We will block the property for 30 days but you can leave whenever you like
Designer steel, glass and titanium single family with Million Dollar Views, located few minutes from Waikiki, downtown, and walking distance to tropical forest trails.Has the feel of a tree house as you relax among centennial monkey pods.5 bedrooms, 5 + 2 half baths,...
Hale Ohia: Secluded Home w/ Private Pool, Ocean & Mountain Views, BBQ
Welcome to Hale Ohia, where you will feel right at home here in the paradise of Hawaii along Kauai’s stunning North Shore. Located just above the Queen’s Bath tidepool, this 6 bedroom, 3 bathroom 3-story home hosts up to 12 people in a nuanced design that combines...
Uncle Richard's Waikiki Beach Studio w/Parking
Soak up the island vibes from this bright, breezy studio just a short stroll from Waikiki Beach. Nestled among vibrant shops, local eateries, and island nightlife, this modern retreat features a private lanai, fully equipped kitchen, fast Wi-Fi, and free assigned garage...
Beachfront Mana Kai Maui Unit #502
Summary:Premium ocean front condo with the best location (2nd unit from the ocean end of building), on the best beach, and the best part of Maui - the Mana Kai. Located at the north end of Keawakapu Beach, you've got a mile long beach and some of the safest swimming and...
180° Ocean views • Luxe condo • Steps to Beach
Enjoy panoramic ocean & sunset views year round from, Kihei Lani, a 5th floor luxury condo that artfully blends contemporary design, modern amenities and island style. Full, whisper quiet AC in all rooms! Ideally located in Kihei, the condo is right across the street...
Oceanfront condo with lanai, pool, grill, beach gear, smart TV, W/D, partial AC
Lauloa Resort 110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Overlooking Maalaea Bay, this Lauloa Resort condo is surrounded by swaying palms and the sunshine's rays! When you...
Poipu Sands 434, 2BD Ocean View, AC in Bdrms, High End Vacation Rental
Aloha from paradise! Take in the breathtaking ocean views while having breakfast on the large lanai (balcony), or listen to waves crash as you drift off to sleep! You'll enjoy a spacious 1353 sq. ft, full kitchen, A/C in bedrooms, and many recent updates! Right on the...
Mahana 1119 Early Summer Deal at Luxurious Condo with Panoramic Ocean Views
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Mahana 1119, an eleventh-floor 2-bedroom, 2-bath corner penthouse that sleeps up to 6 guests and occupies Mahana’s most...
Serene Ocean Vw, Pool, 1Bd/1Bth 20% off Feb - Apr
Keep your eye open for last minute discounts!Currently and through October 31, 2025 we are running a 30% off special for guests who rent 7 or more nights!Kai Moana Hale is a one bedroom one bathroom unit on the second story of a two story building. This is a well...
Wailea Ekahi Village | 35C
Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one-bedroom, one-bathroom condo offers an ideal blend of comfort and luxury. Make use of the ground floor location to really live an indoor/outdoor...
Orchid Hale, A/C, Elegant, Extraordinary Home!
Whether you are traveling with your family, extended family, other couples, best friends or your sweetheart, Orchid Hale is an excellent choice of accommodation. You will always remember the special time you spend here; the spacious elegance, the extravagant feeling of...
HALII KAI 15B is booked until May 2025! Discounted rates May thru October!!
OCEANFRONT VILLA Handicapped accessible No carpet Open the door Hali'i Kai15B and feel the Aloha greeting of the crashing blue waves! Relax in the serenity of your luxury retreat-the private lanai is on the water's edge-perfect for alfresco dining and the most perfect...
🏖️Beautifully Furnished | Waikoloa Colony Villas 1503 | AC & WIFI | vrKCV🏖️
vrKCV - Waikoloa Colony Villas 1503, Professionally Managed by Kona Coast VacationsWelcome to Waikoloa Colony Villas, where tropical luxury meets modern convenience. This beautifully furnished 2-bedroom, 2.5-bath townhome is nestled within the gated Waikoloa Colony...
Serene Hawaiian Eco Village 15 minutes from Hilo
Welcome to the Hawaiian Wildlife Habitat Eco Village, which is part of the responsible tourism effort to take care of the Aina (Mother Nature in Hawaiian). We offer an individual detached self contained bedroom (hexagon) with full bathroom and a kitchenette. To start...
Four Bedroom Oceanfront Estate at Naupaka Place at Waikoloa Beach!
Welcome to Pacific Sunset Villa, home of expansive ocean views and ultimate luxury. This award winning home with 4 bedroom with ensuite bathrooms and 3 half bathrooms sits on an oceanfront setting and offers easy access to all the amenities at Waikoloa Beach Resort.The...
Spring Special! Live Inspired! Live Kapalua Beautiful Villa! – No Resort Fees
Step into luxury island living at this beautifully upgraded one-level, two-bedroom Golf Villa in the heart of Kapalua Resort. From the moment you walk through the door, pride of ownership is evident in every detail. This corner location villa offers privacy,...
Exquisite Condo with an Awesome Ocean View Emerald 289
Maui Kaanapali Villas is located on 11 acres of beautifully landscaped tropical gardens. The beach in front of the property is rated number one on Maui. There are many activities just steps away including snorkeling, swimming and scuba. Check out Castaways restaurant...
Walker's Lanikai Beach House – Historic Oceanfront Retreat
Welcome to Walker's Lanikai Beach House. John Walker, was a Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). Mr....
OCEAN VIEWS* LUXURY AND LOCATION AT HUALALAI RESORT ** TWO GOLF CARTS**
Located in the Award Winning Resort Community of Hualalai Four Seasons.Enjoy the sounds of the ocean serenade, the magic of sunsets, and whale watching during the winter months, from this recently updated garden level Hillside Villa. Appreciate the close proximity to...
Maui Resort Rentals: The Whaler 562 - Fully Renovated 5th Floor Studio, Fantastic Pacific Ocean and Black Rock Views!
Enjoy spectacular views of the Pacific Ocean, Kaanapali's famous Black Rock, Maui's neighbor island Molokai, and the lush West Maui Mountains from this upgraded interior courtyard 5th-floor studio suite at the Whaler in the heart of Kaanapali Beach.Its fully renovated...
Five bedroom log cabin near Waipi'o Valley
The Log Cabin, a licensed 'inn', is located in lush and peaceful Ahualoa, just an 8 minute drive up the mountain from historic Honokaa town. The Log Cabin is a great setting for families, groups, weddings or other special events.You can enjoy a stroll around the yard or...