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.
Renovated Condo in an Oceanfront Complex with AC, Lanai, and Pool/Hot Tub Access
Kauai Beach Villas D10Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Lounge by the pool, take long strolls on the beach and catch some of the most beautiful sunrises you've ever...
Island dream Getaway PK-E304
Pono Kai's pool and spa will be closed January 6-31, 2026 for the instillation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Island Dream Getaway is your perfect Kauai island escape! Nestled in the...
Bamboo Suite - Beachfront Ground Floor Condo - Lae Nani 316
Aloha! This great condo is ground-floor, oceanfront, two-bedroom, two-bath — overlooks beautiful Wailua Bay on the Garden Isle of Kauai. From the lanai you look across the broad green lawn with its palm trees and tropical plantings to a natural sandy swimming...
❤️PiH❤️ Seabreeze ★Amazing Family Home ★ Private Pool & Spa ★ Bikes ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Seabreeze, a part of our Hawaiian Luxury Collection. Seabreeze at Mauna Lani Villages is a wonderful 4 bedroom home that features a private pool and spa, with luxurious high end finishes in a premier resort...
LIGHT & BREEZY Unit #115. West Maui open, Reserve now Maui Strong!
LIGHT & BREEZY style studio! Oceanview and is just steps from the sand. Located at The Napili Bay in West Maui, it is walking distance to Kapalua. Enjoy the blissful sandy beach and serene tropical water, not to mention the wonderful West Maui breezes. Discover why...
Upgraded Quiet Garden Oasis, Split System AC
This beautifully upgraded condo is meticulously cared for by the owners and it’s the first time in years that they have made this condo available for rental. While this unit enjoys a garden view from the lanai, the resort itself is situated right on the ocean bluff...
Beautiful ground floor unit!
This spacious one bedroom condo sleeps four people comfortably. Step off your private lanai (patio) onto plush green grass for a short few steps to a beautiful heated swimming pool, surrounded by colorful tropical foliage. Then, take a few more steps through more...
Menehune Shores #623 – Top-Floor Penthouse with Stunning Ocean Views
Menehune Shores #623 – Top-Floor Penthouse with Stunning Ocean and Mountain ViewsWelcome to Menehune Shores #623, a beautifully remodeled penthouse that offers soaring ceilings and breathtaking views of both the ocean and mountains. This top-floor retreat blends...
Pali Ke Kua #241 - Top Floor Ocean View
Perched on an ocean bluff near Hanalei Bay, Pali Ke Kua Unit #241 is a one-bedroom + loft, two-bath, second-floor unit with sweeping ocean views. As of July 2021, there are 3 A/C portable units in the condo. Please note this condo does not have central AC. The family...
Time to go to Maui $125. per night! May and June only. Ocean view!
Aloha, Our spacious one bedroom condominium C309 at the popular Kihei Akahi complex in South Maui is located on the 3rd floor of the C bldg, C309, with a nice ocean view. We have a new King Size bed and new bedroom furniture. Overlooking the blue Pacific waters at...
Ocean Front Pool Club. Includes Beach Gear! Halii Kai 24H
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 24H. Stunning 3 bedrooms. Ocean Front Pool ClubPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin...
Traditional Hawai'i home near Hilo town - solar powered!
E komo mai (welcome!) to this 1940s plantation-era home in Hilo, the cultural center of Hawai’i. Here, you can hang loose and absorb the spirit of aloha while you explore the windward, tropical side of our island, including the Hamakua Coast and Volcano National Park....
❤️PiH❤️ Island Song Villa♥Dual Master★Amazing Views★Newly Decorated
Island Song Villa brought to you by Paradise in Hawaii Luxury Homes.Welcome to Island Song Villa, a part of our Hawaiian Luxury Collection. Island Song Villa at Islands is a wonderfully large, 2,189 square foot, two-bedroom home that can sleep 5. Located in the Islands...
Great Wailea studio Condo
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully this provides some clarity if you have been following this process and were concerned about booking in the next couple of...
Hilo SunShine Rental.2bds1ba,common swimming pool.
Two bedroom have window Air condition!The apartment is located in the center of Hilo, with an area of 575sf, located on the second floor, with two bedrooms, one living room, one bathroom and one balcony. Brand new decoration, brand new furniture! The community is...
Keauhou Palena - 2nd floor unit overlooking the golf course KP604
TMK: 780100320024TA: 008-300-1344-01Welcome to our beautiful unit at Keauhou Palena! The complex is right on the Kona Country Club and only a short walk to Keauhou Bay (1/4 mile). Keahou Shopping center nearby offers a movie theater, grocery shopping and plenty of local...
Malia Kai#5: Beautiful Townhome in Heart of Kona Town: Walk to everything!
Malia Kai#5 is a unique & special rental opportunity for your upcoming Hawaii Vacation! Enjoy Townhome Living with no one above or below you in the heart of Kona Town! You'll notice this intimate complex is extremely peaceful & the perfect oasis for one to enjoy the...
DISCOUNTED RATES! 113 Darling little ground floor 1 bed, 1 bath with A/C
Kulakane Resort is a West Maui vacation rental property, located just a few miles north of historic Lahaina Town. Each vacation rental property is professionally managed and superbly maintained to the highest standards. Your Maui vacation can be enjoyed in one of our...
Ocean view in Paradise
Our newly remodeled ocean view condo has a new Queen size bed and a full size kitchen that is fully stocked. It has a full size stove with oven, microwave and full size refrigerator.The Condo has everything you will need for your stay in paradise.It is a fully furnished...
#225 Your Slice of Paradise.
A LITTLE BIT ABOUT THIS CONDO... Polynesian Shores 225. Everything you need for your Maui dream vacation is here... just bring your suntan lotion and flip-flops and enjoy the Hawaiian sunshine. This condo has recently been refurbished to make your stay even more...
Air-conditioned, elegant and spacious, golf course view, walk to beach!
Emmalani Court is a small tranquil Princeville condos complex adjacent to the Makai golf course, offering scenic ocean and golf course views, large air-conditioned units, and convenient access to the many beaches and attractions that north shore Kauai has to offer. The...
Stunning Views, Walk to Beach! Spacious Ekahi 49F
This listing has views from your lanai will have you coming back year after year--and the beach is a short stroll across the condo property! A cozy one bedroom and one bath second floor, this unit supplies you with everything you need for a memorable vacation. Choose...
Escape to "Heavenly Haven", our beautiful, by the sea, comfortable Condo
This is a gorgeous one bedroom, completely handicap accessible, and completely remodeled condo. Our condo is one of the best in Kihei Garden Estates with granite countertops, tiled floors, large flat screen TV, marble shower, air conditioning, expanded digital cable ,...
Island View - Studio - Westin Kaanapali Ocean Resort Villas - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using...
ISLANDER AT THE BEACH OCEAN FRONT CONDO # 145
**** WE ARE UNDERGOING CONSTRUCTION , FOR THE MONTH OF JULY AND AUGUST AND ARE DISCOUNTING THE NIGHTLY RATE **** This ground floor ocean front condo next to pool and spa offer the perfect Kauai getaway. New Queen size bed, , studio offers comfortable accommodations and...
Hale Kamaole 117 first floor condo, easy access to best beach on Maui!
Hale Kamaole is just a short walk from the Kamaole Beach III, where milder tides, full facilities and a lifeguard post makes for a low stress family atmosphere. Kamaole III is one of Maui’s favorite beaches and is great for snorkeling, a morning swim and postcard...
KKSR2103 DIRECT OCEANFRONT, Ground Floor, REMODELED KITCHEN, AIR CONDITIONING
Welcome to Paradise! You found the perfect condo for your Hawaiian Vacation. 2-103 at the Surf & Racquet Club is a gorgeous, 2 bedroom, 2 bath DIRECT oceanfront ground floor property. This property has EVERYTHING you'll need. Wifi, Beach Gear, all available for your...
Whale watcher's delight! Spacious penthouse, views
This spacious top floor condo in the upscale Puu Poa complex on the north shore of beautiful Kauai is located directly next door to the Princeville St Regis Hotel. You'll love the newly renovated oceanfront pool! Also available onsite are tennis courts, pickleball...
ALOHA-WAIKIKI OCEAN VIEWS, POOL, FREE PARKING, SLEEP 4 and MORE!!! WB28
Large one bedroom Apartment has nice peeks of the Ocean & Diamond Head from balcony, bedroom & living room. FREE PARKING for one vehicle with this unit, Pool, BBQ and other perks on site makes this a great singles, couples and family destination within Waikiki AND only...
Panoramic Ocean Views, Pools & Hot Tubs
Welcome to your slice of paradise at Country Club Villas #325! This top-floor corner unit is one of only four exclusive residences in the complex, offering 1,271 square feet of extra living space and breathtaking views. Perfectly positioned with frontage on the golf...
Enjoy Vintage Hawaiiana! Napili Maui awaits!
5 MINUTE WALK TO NAPILI BAY BEACH. Our Napili condo is walking distance to Napili Beach, Kapalua Beach and Kapalua golf resort. You can enjoy the best of both worlds, amenities you would find at a local condo resort plus the quiet and privacy of a local resident.Free...
Hilltop Views! Backyard Pool, 3 Bedrooms/3 Baths. Gentle Breezes. Very Private.
House DescriptionCome stay in at our park-like property on a breezy hilltop with a wide view of the ocean less than a mile distant. The pool and adjoining covered cabana is secluded and private in the backyard. The neighborhood is a pleasant but ordinary residential...
☀️5br / 4ba ★Huge - 2500sf★Sleeps 11 ★Walk to Beach, 30 seconds to pool.★Hyatt
Spread out in this massive 2500sf of interior space spread across 5 bedrooms, 4 bathrooms, and spacious common living. It's great to vacation together, but it's a bonus to not be stepping on people's toes when relaxing after a long day at the nearby beach. ♔★This...
Oceanfront on Oahu's Gold Coast!
Colony Surf #604 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)The best of Hawaii awaits you in this large (1519 sf) oceanfront double-sized corner condo at renowned Colony Surf on...
Palms at Wailea - Fully Air Conditioned
Welcome to our Wailea Condo at the Palms of Wailea. Our condo is a large 1200 square foot newly renovated two bedroom, two bathroom condo that is walking distance to some of the best beaches in the world. For your convenience, we provide beach chairs, beach towels,...
Just finished complete renovation in March, 2025
Welcome to your Hawaiian Acacia tree oasis. Some call it the rain tree. Others call it the Monkeypod or Saman. You will call it home while you enjoy Kauai. Every detail of this remodel was meticulously crafted by hand using actual Monkeypod trees sustainably harvested...
Manualoha 901 - Minutes to Poipu and Brennecke`s Beach
MANUALOHA 901 AT KOLOA KAI VACATION RENTALSSpacious 3-Bedroom Condo in Sunny PoipuWelcome to Manualoha 901, a rare and generously-sized 3-bedroom, 3-bath condo located on the ground floor in the heart of sunny Poipu. Perfect for families or groups, this tropical retreat...
Two Bedroom Ocean View Deluxe Luana Kai A303
A303 is a deluxe, 2 bedroom, 2 bathroom ocean view condo with AC. A303 is on the third floor, there are NO elevators, so you are walking up stairs.A303 is on the third floor with great views of Molokini, Kahoolawe, Lanai, Maalaea Bay and the West Maui Mountains. It is...
Unit #209-3BR/2 Bath: 3 BR, 2 BA Condominium in Lahaina, Sleeps 6
Honokeana Cove 209 is a 3-bedroom 2-bath top floor unit just a quarter mile south of Napili Bay's sandy public beach. This lush, tropical 38-unit property sits on a secluded cove with breathtaking views of passing whales (in season), dolphins and the island of Molokai....
Special if booked 30 days+ $2864.40/month- 2 bed/2bath cozy- quiet
Aloha & welcome to Kohola Hale, (or Whale House), your home away from home. Whale and ocean decor await you throughout the home. Kohola Hale sleeps 4 comfortably with one King and one double bed. Both bedrooms have their own bathrooms. The Hawaiian style and comfortable...
Beautiful Beachfront Resort, Resort and Oceanview Unit, 4 pools, 2 Jacuzzis,
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.This is an amazing first floor studio in building 4 (building closest to the beach), with a patio facing the pool/resort area with ocean views. Step out your door, and short...
Aston Whaler at Kaanapali 770: Sweet 7th floor 1 Bedroom Ocean View Condo
Enjoy Maui in comfort in this sweet, home-like condo located on Kaanapali Beach. The tasteful interior design, wide-open layout, and seventh story views of the horizon on the Pacific Ocean truly transcend you into vacation mode.The bedroom has a California king bed and...
Vitamin Sea available on Maui Come Play at Kahana Reef 402
Close to sailing, scuba diving, and more, this smoke-free condo brings it all within reach. Kahana Beach is within an easy 10-minute walk and Ka'opala Beach is also a quick 13-minute walk away, so leave your car at the property, which offers onsite parking. After you...
Beachfront HK-B16 - Maui Gardenview Condo in Secluded Resort on Ma'alaea Bay
Experience the best of Maui at Honu Kai's centrally-located condo, B-16. This tranquil oasis offers a serene bedroom with A/C and a comfortable queen-sized bed on the second floor, while the living area provides privacy with a shoji door, a queen-sized sofa sleeper, and...
Luana Kai B201 | Luxurious Updated Condo, Oceanfront Property!
Welcome to this Zen garden paradise also known as Luana Kai B201. Surrounded by lush tropical foliage and stylishly decorated with colors and furnishings that provoke a feeling of calm, this condo will be your favorite place to escape to year after year.Remodeled,...
Maui Sunset Vacation Rentals A420
Best view, ocean front view on the fourth floor. Sweeping views of grounds and the Pacific Ocean. One of the best locations on the property. New flooring 2024Watch the life of Maui unfold from the morning till evening from your private 180 sq foot private view deck....
1Br 1Ba Kahala Tropical Dream, Pool, Garden View 513
Located in Koloa Hawaii, this beautiful 1 bed/1 bath condo awaits to immerse you in local history and tranquility. With proximity to the serene beaches, barbecues, and hiking nearby, you'll be sure to fall in love with the culture of Koloa. Right outside your door is...
Enjoy the Views and Tropical Breezes Condo at The Cliffs
Soaring ceilings and walls of windows make this spacious unit feel even larger. Located on the third and top floor of The Cliffs, you will be treated to breathtaking views of the lush Princeville tropical landscape and long ocean views. From the living room lanai, you...
Beautiful, Upscale Ground Floor Condo - Feels Just Like Home
Ali'i Kai 10A is a perfect blend of modern luxury and island charm located in the heart of all Kauai's North Shore has to offer! This beautifully updated, super inviting ground floor unit has two comfortable bedrooms with private ensuite bathrooms, and an open concept...
Remodeled oasis in the heart of Waikiki! Min. from beach, shops, & restaurants!
Whether you seek relaxation, remote work vibes, ocean waves, or stunning sunsets, my cozy 1 bedroom space awaits. Experience the charm of my recently renovated dwelling, featuring one complimentary parking space. Revel in ample light, air, and full amenities. The living...