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.
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
This property is professionally-managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1757. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
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...
Hale Nani at Kukui'ula - Luxe Family Hideaway with Poolside Living in Poipu
Summary:TA-101-738-2400-01Hale Nani at Kukuiʻula is a contemporary 5BR, 5.5BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites...
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...
Renovated 2 bd condo steps to Kihei beaches
Haleakala Shores A410 is a 2-bedroom, 2-bathroom with a split air conditioning system and 2 master ensuites and can accommodate up to 6 guests. This 4th-floor haven of unparalleled luxury and comfort has been meticulously crafted to enhance your Maui getaway. Recently...
Breathtaking Sunset Views and Perfect Backyard Pool and BBQ
House sits a right up the hill from downtown which makes for an amazing sunset. The property has a saltwater pool, patio and BBQ. Inside is fully furnished for a comfortable stay. The garage is remodeled and includes a ping pong table, corn hole, darts and full of beach...
Blue Hawaii - Top Floor Lae Nani 334 - Beachfront Condo with AC & WD
Enjoy the best that Kauai has to offer from the comfort of your own top floor Wailua Bay condo! Fall asleep and wake to the sound of the ocean in your king bed and enjoy the oceanfront view from your private 3rd floor deck. This is one of the few units at Lae Nani that...
Includes Beach Gear! 332 Shores at Waikoloa
Shores at Waikoloa 332Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie...
Superior 1 Bed Bright decor Part ocean view King Bed No risk of zoning change
The Kihei Akahi, opposite Kamaole II Beach Park is a fantastic property for both couples and families. Mere steps from the beach, the property features 2 pools, 2 barbeque and picnic areas, tennis courts, beautifully landscaped gardens, ample parking and onsite...
1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned
Retreat and relax in this comfortable, serene, light and airy, completely remodeled unit. This ground floor unit in the quiet, beachfront Wailea Ekahi Village won't ask you to carry your bags up a single step, while still providing a private and open environment....
Luxurious Two bedroom Unit with Panoramic Ocean View in ONE Ala Moana
This luxury corner unit has an epic panorama ocean view with floor-to-ceiling windows on 2 sides of the unit for a spacious feel. ONE Ala Moana is the pinnacle of world-class living. This unit has 2 bedrooms, 2 baths, and 2 parking stalls directly in front of the...
Kolea 8C: 3 BR, 3.5 BA Condominium in Waikoloa, Sleeps 6
Kolea 8C is a three bedroom, three and a half bath penthouse villa with an exquisite ocean and mountain view. It is perfectly situated overlooking the Kolea Beach Club, Anaeho’omalu Bay and Hualalai. The African Mahogany trimmed glass panels that form the lanai doors...
Wailea Grand Champions 43 - 2 Bedroom Garden View Condo
Wailea Grand Champions 43 is a stunning vacation rental nestled in the heart of Wailea, offering a luxurious escape with breathtaking views and unparalleled comfort. This elegantly designed property is ideal for those seeking both relaxation and adventure on the...
Valley Isle Resort #1110 - Vacation West Maui
Just minutes to Ka'anapali, Napili, and Kapalua, the Valley Isle Resort will give you and your family the fun and relaxation it needs.Great Restaurants and Shopping Within Walking Distance of the ResortDirect Beachfront Accommodations on Kahana BeachFive 18 Hole...
'Olu'olu by AvantStay | Single-Story Home by Ocean
Kick back in the heart of Makaha Valley at 'Olu'olu, a 3BR retreat that puts you 6 minutes from the beaches of Oahu. With a stunning view of tropical mountains from your backyard patio, this modern Hawaiian escape blends style, space, and a beautiful location to give...
Lokelani B102 – Premium Oceanfront Retreat Steps from the Sand
Experience the Elegance of Oceanfront Living at Lokelani B102 – Your Private Maui EscapeStep into your dream Maui getaway at Lokelani B102, a fully renovated beachfront sanctuary offering uninterrupted panoramic ocean views just steps from your private lanai. Nestled...
OCEANFRONT Cliff house ~ RELAX to the Sound of Waves ~ SPECTACULAR Views
Welcome to Hale Kailani, the 'Sea and Sky House'. Enjoy breathtaking views of the Pacific Ocean, amazing sunrises, occasional lightning storms, year round turtle and spinner dolphins and seasonal humpback whales right off the back lanai. Located just south of Hilo on...
Ko Olina Beach Villas 0401: 3BD Corner Luxe Villa w/ Pool & Garden Views
Welcome to Ko Olina Beach Villas O401, a corner retreat on the upper floor of the Ocean Tower at Ko Olina Resort. This elegant three-bedroom, two-and-a-half-bath villa offers a seamless blend of sophistication and island ease, surrounded by panoramic views of the...
🏖️Beautiful Resort | AC | Walk to Beach & Restaurants | vrKCV
vrKCV - Waikoloa Colony Villas 1906, Professionally Managed by Kona Coast VacationsWelcome to Hale Laule'a – Your Peaceful Retreat on the Kohala CoastLocated near the stunning Kohala Coast on the Big Island of Hawaii, Waikoloa Colony Villas 1906, offers the perfect...
❤️PiH❤️ LOTUS PAD ★ Amazing Views ★ Heated Pool ★ Bikes ★
Brought to you by Paradise in Hawaii Luxury Homes.Lotus Pad is a quiet oasis in the KaMilo community overlooking Mauna Lani North Course with views of the ocean and Maui in the distance.We pride ourselves on providing some of the most sought after homes on the Kohala...
Chameleon Suite Ocean Views Kitchen Volcano NP
About this spaceSee our 5 star reviews! Looking for a unique stay w Ocean Views, cool nights, beautiful sunsets, & Chameleons? We are centrally located between Hilo & Kona 50 minutes from the Volcano. Perfect for exploring the South End of the Island. Chameleon Suite is...
One-of-a-Kind Maui Getaway!
The Butterfly Home | Maui, HawaiiThis estate is more than a home—it is a vision brought to life by its architect-owner as a personal passion project. Designed with Maui’s natural beauty as the muse, every detail reflects an intention to blend art, architecture, and...
Trade Winds Plateau
Located on a private, gated road, experience fresh air that's travelled thousands of miles over the ocean. Explore 15 acres of the most beautiful property in the universe. Be prepared for 50,000 shades of verdant green to welcome you to a beautiful oasis of privacy....
Walk to Hanalei Bay&Town. Views of Waterfalls&Mountains. A/C. FREE Surf,Sup,Bike
Aloha, You will love our 3 bedroom, 3 bath HANALEI GETAWAY Vacation Rental home that is perfectly situated in the heart of Hanalei Bay, Kaua'i. At your vacation home you will experience the views of numerous breathtaking waterfalls and the majestic Hanalei mountain...
Heated Pool and includes beach gear! Waikoloa Fairway Villa L4
This vacation rental is professionally managed by ResorticaHawaiiPLEASE NOTE: Waikoloa Fairway Villas L4 is listed for sale. Please reach out with any questions. 11/18/25Waikoloa Fairway Villas L4.Please scroll down for detailed informationBedding Configuration:Master...
3 bedroom house with WIFI and free parking, close to beaches and hikes.
Make yourself at home in this 3-bedroom Makaha retreat. With 2 queen beds, a twin with trundle, and 2 full bathrooms (with shower, bidet, and hair dryer), this home is set up for a relaxing and easy stay. Enjoy WiFi, a washer/dryer, and other thoughtful touches...
Hawaiiana Hale – Ka'anapali Beachfront Home
Hawaiiana Hale is one of the most luxurious beachfront homes in Maui. With breathtaking panoramic views that sweep from the golden sands of world-class Ka'anapali Beach to the warm, calm waters and the islands of Lana'i and Moloka'i. You will experience true paradise at...
Kolea 14K ~ Immaculate, Luxurious, Special Rate+ Lava Lava Beach Cards!
Kolea 14K Current Special Rate $550/nt+tax plus $100 Lava Lava Beach Card for a Limited Time!The perfect vacation rental awaits you! This 3 bedroom, 2 bath condo is centrally located in the beautiful oceanfront neighborhood of Kolea. It is one of those versatile homes...
Luana 15D: Upper-Floor 3 Bed Villa w/ Private Lanai, BBQ & Garage at Honua Kai
Welcome to Luana Garden Villa 15D, your personal slice of paradise located on the upper floor of building 15 in Enclave Three at the prestigious Honua Kai Resort & Spa in Kaanapali, Maui. This spacious 3-bedroom, 3-bathroom villa offers 2,047 square feet of luxurious...
🌹Kona Rose's Hideaway at Kona Plaza at the heart of Kailua-Kona
Welcome to Kona Rose's Hideaway in Kona Plaza #318, your ideal getaway nestled in the vibrant heart of Kailua-Kona! This charming 1-bedroom/1-bathroom suite is perfectly equipped for your comfort and enjoyment, featuring a plush King bed and a cozy Queen bed, along with...
102 Hainoa: Ultra Luxe Oceanview Estate at Hualalai with Private Pool & Spa
Important Resort Notices* Hualālai Spa Enhancements (Sept 15 – Mid-Nov 2025): During this period, the resort’s outdoor aqua-thermal areas will be under renovation. Massage, body, and facial treatments will move to the Makaloa Villa. The infrared sauna, hot tub, and...
Beautiful One Bedroom AC Beach Cottage
Our one bedroom beach cottage is located on a quiet one lane road leading to the ocean. While in a quiet location it is still just a few minutes drive from downtown Hilo, supermarkets, restaurants, airport, medical centers, and scenic parks and beaches. There is a small...
Top Floor Beachfront 1 Bedroom Condo Honua Kai Resort & Spa - Peaceful & Quiet
The best rainbows and grand views are mountain facing. This 10th top floor, fully furnished (Washer/Dryer/Kitchen) 1 Bedroom, 1 Bath is located in the Hokulani Tower at Honua Kai Resort & Spa. New floors and sofa sleep remodeled in Summer 2025!Honua Kai resort offers...
Na Hale 1: Exclusive Beachfront Enclave, Access to 5 Star Private Club + Golf Cart
Decorated with mature palms and lush greenery, Na Hale 1 celebrates modern Hawaiian living at its finest. Enjoy beautiful sunsets over the ocean from your backyard, or from your private beach club. Na Hale 1 has a close proximity to the beach and club - just a few...
Direct oceanfront penthouse. Modern renovation. Exceptional views!
Expansive oceanfront views in paradise!This property is the exact definition of direct oceanfront living and has been newly renovated! You cannot get closer to the water unless you are on a boat. Whale watch from your expansive private lanai and allow the lapping waves...
Kaua'i Island Paradise in Princeville Sleeps 6
Entire Townhouse 1,100 sq. ft. end unit with 3 bedrooms 2 baths for 6 guests:1 king, 1 queen, 1 queen with 2 Full baths. Relaxing atmosphere Townhome with beautiful foliage and mountain views from every window. A mile stroll to a secluded lush and green year round trail...
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
This Kailua, beachside, pool (heated) home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!Each room has an individually controlled AC system. The...
Spacious unit located in Maui Hill Resort+Netflix&more
Welcome to an upscale neighborhood. Aston Maui Hill in the heart of Kihei right next to Wailea. We offer you an entire place. There's one bedroom with king bed the master bed has an attached bathroom and balcony and there will be another queen bed in the living room...
Renovated beachfront with gorgeous ocean views! Luxurious and family friendly!
(See Video Below) Upgraded, with ocean and garden views, direct beach access, patio and luxury amenities to make this your most memorable vacation! Minutes from Shops at Wailea! Family friendly and serene! Just bring your swimsuit and flip flops because we have you...
Condo 1 block from Waikiki Beach
This is my timeshare. Please do not try to book this directly. Send me a request for the dates you are looking for so I can check with the timeshare location for availability. This property is a 2 minute walk to the beach. Set moments from Waikiki Beach and offering...
❤️PiH❤️ Hapuna Surfside ★ Beachfront ★ Steps From Ocean ★ B26
Welcome to Hapuna Surfside at Hapuna Beach Residences brought to you by Paradise in Hawaii Luxury HomesNOTE: To use of the hotel privileges at the Hapuna Westin and Mauna Kea Beach hotel. The fee is $130/ day, plus tax in 2025, for the entire group (Not per person) and...
Designer oasis with waterfall & sunset views, hot tub, kayak, surfboard & bikes
Enchanting Mermaid ManorOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in mesmerizing waterfall and sunset views from both the living room and lanai at this tropical oasis....
Affordable oceanfront condo, amazing views, sunsets, beaches, pool in West Maui
Please support the Maui economy and the people here by continuing to visit this beautiful island. We are in Kahana, seven miles north of the town of Lahaina. Our property was not affected in any way by the Aug. 8, 2023, wildfires in Lahaina town. Mahalo.Kahana Reef is...
Fully renovated & customized condo with lanai, pool, hot tub, tennis, central AC
Shores at Waikoloa Bungalow 225Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Newly renovated and beautifully customized from top to bottom, this elegant, two-bedroom condo is full...
In the Action! Ground floor steps to ocean view pool
Located near the pool area, easy access to BBQ's, pool and beach. Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private patio. Condo has a dedicated free wi-fi internet router providing high speed internet for those who wish...
Top floor, Ocean view! Very quiet 1 bed/2 bath.
Welcome to The Coral Suite at Kona Pacific! Our beautiful, clean, ocean view unit is just the spot to come and relax while you are exploring all the wonders of the Big Island. Our condo is a top floor, spacious unit with a huge lanai. Just renovated the 2 bathrooms...
Stunning tropical retreat near the beach with pool, views & spacious lanai
Ho'oka'ana HaleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Live the luxe life at the top of Alii Heights! Surrounded by colorful blooms and palm trees, find yourself waking up...
Renovated Studio Steps from the Beach & Pool - A/C
Relax at our newly remodeled condo for an unforgettable Hawaiian vacation: ✓ Right across the street from Kamaole Beach II✓ King bed + blackout curtains✓ 2 pools + 2 hot tubs + BBQs + reservable tennis court✓ Beach chairs, umbrella, cooler, and beach towels✓...