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.
Kapalua Golf Villa 14T3 Standard Fairway 3 Bedroom
- Two story villa with 2 stairs from designated parking and front door- - Hardwood floors in living, dining rooms and carpet in bedrooms- - Open kitchen with granite counters includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware, tableware and...
Free Parking 1BR Waikiki Banyan Partial DH Views with AC
Nice and Exclusive 1 Bedroom/ 1 Bathroom / 1 FREE PARKING (max 6`) at the Waikiki Banyan with No better location to enjoy Waikiki’s entertainment, a quick stroll from the beautiful and sandy beach, and great partial views of the Diamond Head! Sleeps up to 4 guests...
Ground Floor 1-Bedroom with AC - 1-Block from Ocean, Restaurants and More!
Welcome to your island escape! This charming 1-bedroom condo at Kailua Village offers the perfect mix of comfort, convenience, and tropical charm. Ideally located in the heart of Kailua-Kona, you’re just steps from the ocean, shops, dining, and all the best local...
Aqua Aloha Surf Waikiki 1207 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1207 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed+ (1) Queen Sofa sleeper, Sleeps 4, 360 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that...
Inviting apartment with city views, WiFi, partial A/C, washer/dryer, & balcony
The Keoniana #111 - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Relax in style at this well-equipped aparthotel minutes away from Honolulu's picturesque beaches,...
Grand Champion Villa Getaway - Wailea Beaches
Summary:🌴 Prime Location – Walk to beach, dining & shops🌅 Tranquil Balcony – Enjoy morning coffee w/ lush views 💤 Luxury Beds & Linens – Ultimate comfort for deep rest 🏊 Resort-Style Amenities – Pool, hot tub & tennis courts 🚗 Free Parking (1 spot) – Secure &...
Kauhale Makai 331: 1 br condo @ Ocean Front Resort in S. Kihei Sleeps 4
Enjoy Ocean Views from this one bedroom Condo. The bedroom has a queen bed and the living room has a sofa bed, allowing the unit to accommodate up to four (4) people. The living room features a new flat-screen TV and has a mixture of rattan furnishings with tropical...
Haleakala Shores A309 | 2 Bed, 2 Bath
Summary:Comfy Sunny Kihei Condo @ Haleakala Shores, Across Street From BeachThe Space:Two couples can enjoy a perfect Maui getaway at Haleakala Shores A-309, with two bedrooms and bathrooms, there’s plenty of space. Want to play on the beach -- You’re only a block from...
Quiet Villa, Large Lanai, On the Golf Course
Welcome to your peaceful island retreat in Waikoloa Village - perfect for families or couples seeking sun, comfort & ocean views! Enjoy relaxed resort living surrounded by tropical beauty:- Sleeps 4 | 2 bedrooms | 3 beds | 2.5 baths- Pool, hot tub & gym access- Private...
Wailea Ekahi 52B | Resort Level Amenities!
With 34 acres of landscaped resort bordering one of Hawaii’s best beaches, Wailea Ekahi 52B is the ideal place to experience the very best of Hawaii. It’s affordable luxury that’s perfect for two couples wanting to share an island getaway. There’s a minimum stay...
Lush Palm View in Casual Maui Condo w/Full Kitchen, AC, WiFi–Kamaole Sands 8210
Captivating and recently remodeled, the kitchen and bathroom will have guests ready to move into their 'home away!' Upon entry, guests will feel the welcoming flow in the tile flooring, tropical accents, and consistent rattan theme. Begin the day with coffee or tea in...
Awesome 1 Bedroom at Waikiki Banyan #907 T-1
Aloha and welcome to your beautiful new home-away-from-home at the Waikiki Banyan, just a couple blocks from Waikiki Beach! This 9th floor unit of the Waikiki Banyan has been remodeled with tile and vinyl flooring, granite countertops, new cabinets, and bathroom.Fully...
Gorgeous Mountain Views, Includes Discount Golf Package, Near Ocean and Shops
Welcome to your peaceful Hawaiian retreat in beautiful Waikoloa Village - where island breezes, mountain views & comfort meet tropical charm:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Wraparound lanai w/ Mauna Kea & golf course views- Shared pool, hot tub, gym & BBQ...
Maui Resort Rentals: Kaanapali Ali'i – Oceanfront Ground Floor + Yard Area, 6 Total Bedrooms+DEN, Sleeps 20, Steps to Pools, Beach, BBQs!
This one-of-a-kind 6BR plus den ground-floor listing at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach brings together an oceanfront 2BR suite and two luxurious neighboring 2BR partial ocean view suites. This combination offers a massive 5,000+ sq ft of...
Beach condo with shared pool & hot tub/private lanai - near beaches/restaurants
Kona Bali Kai #331Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next Kona vacation is about to get a whole lot better when you book this fantastic condo conveniently located...
Makena Surf G105 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf G105 is a prime oceanfront vacation condo that spans 1,510 sq. ft. and is situated on the ground floor. This inviting unit features two spacious bedrooms and two bathrooms, accommodating up to six guests comfortably. The bedding arrangement includes a king...
Central Air, modern furniture well maintained grounds and close to the sea
You are responsible to follow Hawaii state rules and regulations regarding travel and COVID-19. See website hawaiicovid19 dot com for current requirements. Refer to website cdc dot gov for all federal guidelines. More details may be available at the state of Hawaii...
Perfect North Shore Getaway w/ Amenities & Views!
Discover the very best of beautiful North Shore of Kauai from the comfort and convenience of this upgraded private retreat! Perfectly situated in the heart of Princeville, enjoy outdoor amenities or experience all of the incredible beaches, trails and resorts...
Makena Surf G202 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf G202 is a charming oceanfront vacation residence located on the serene south side of this luxurious resort. Just a short stroll from the parking lot, this second-floor unit offers picturesque views of the secluded beach at the southern edge of the property....
Newly Updated Corner Unit w/ Ocean & Mountain Views from Huge Lanai
Alii Kai 2201 is a chic and cozy open concept escape in the heart of all the North Shore has to offer! The peaceful and private corner unit has two light-filled bedrooms, a master suite with king bed and guest bedroom with a queen, comfortably furnished living and...
Wailea Ekahi Village 8D - 1 Bedroom Garden View Condo
Wailea Ekahi 8D is an exquisite vacation rental located in the serene Wailea Ekahi Village. This spacious one-bedroom, two-bathroom condo is located on the second floor with vaulted ceilings and elevated views over the landscaped grounds below. Enjoy the large and open...
Corner studio with fast WiFi, expansive mountain views, pool, & grills
Paniolo #202AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to cooling trade winds and magnificent views of the Hanalei Mountains from this corner, loft style studio...
1 Bedroom Oceanfront in Kaanapali - Papakea A109
Welcome to Papakea #A109. This ground floor Maui vacation rental offers direct ocean front views from the A building at the beautiful Papakea Resort. The remodeled condo allows for up to 4 occupants with a queen size bed and a queen sofa sleeper. New stainless steel...
Secluded Paradise: Ocean view oasis with private lanai and island enchantment
Sealodge B6 is a charming little hideaway that blends Hawaiiana vintage charm with modern updates! This quiet and cozy condo has a comfortable master suite with a queen bed, as well as a punee (Hawaiian day-bed) in the living room that's great for laying and watching...
Maui Resort Rentals: Honua Kai – Incredible 7 Bedroom Oceanfront Offering, Over 4400 combined Sq. Ft. w/ Built-in Viking BBQ!
This incredible seven-bedroom pairing combines a stunning 3BR oceanfront residence with two neighboring 2BR partial oceanview suites to create the perfect gathering space for large groups and families to reconnect and celebrate. Your group will enjoy the space and...
King Bed & Futon - Waikiki - Quiet and central living
Legally permitted vacation rental: KUHIO VILLAGE 2463 Kuhio Ave #1103âš•âš•For your health and safetyâš•âš• We utilize additional Sterilization procedures between reservations.This is one of the larger floor plans in the Kuhio Village, with two balconies, and a kitchenette....
very last minute special ultimate luxury resort, romantic, fun and "zen"
Note: if the requested dates are not available, I also have three other rooms on the property, VRBO #579874, #666626, and #595354, vrbo#460973, #492665.The Kauai Beach Resort - a gorgeous boutique is located along three miles of secluded beach in Lihue, Hawaii. Lihue...
Kamaole Sands 5-311 | Across from the Sand!
Nestled within 15 acres of lush landscape filled with tropical flora, freshwater ponds and resplendent waterfalls, and right across from the sun-drenched sands of Kamaole Beach III, you’ll discover Kamaole Sands 5-311. Perfect for a romantic getaway or small family...
Oceanfront Living W/Lanai and Laundry–Poipu Shores
Castle Po'ipū Shores 203B - Cherish every moment in this two-bedroom, two-bathroom, oceanfront condo with breathtaking views of the Pacific. As guests take their first step inside the unit, they will notice the bright and minimalistic Hawaiian-themed open concept that...
Hale Lani:Direct Oceanfront Massive Pool, Gated, Remodeled Beauty
Truly beautiful, Oceanfront 3 bedroom, 3 bathroom home with a HUGE pool and amazing views! This gorgeous home has some recent renovations, and sits on a large lot size with stunning tropical landscaping. The main level has 2 bedrooms, 2 bathrooms, with an open concept...
Hale Kamaole 309 Third floor condo, easy access to best beach on Maui!
Beautiful Ocean Views from this two bedroom condo with loft from living room, kitchen and both bedrooms. Ocean, pool and mountain views from lanai. Light and bright condo offers all the updates you can think of. New living room furniture, including 3 piece sectional,...
Aloha Hawaii: Waikiki Condo with Great Mountain Views & Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Aloha Rejoice: Beautiful ocean-view lanai. Great location only 2 miles from Kona
This is a beautifully renovated 2nd floor (Townhouse). Spectacular view from the 600 sq. ft. lanai. Located just minutes to the beach and downtown Kona. Private entrance & ALL NEW furnishings. The lanai on this home is absolutely breathtaking! Both bedrooms have sliding...
Oceanfront condo with balcony, W/D, wet bar, & pool access - gorgeous views
Lanikai #133Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Make your escape for the Garden Island at this gorgeous, beachfront condo, boasting sweeping ocean views from the balcony....
Monthly Discovery Bay 2611 2 bedroom Ocean/Sunset/Marina - 2 Queen Beds
PANORAMIC OCEAN VIEWS, 5 Minute Walk to Beach, High Floor, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 1 Month Minimum / contact Agent.Sweeping Ocean Views from High Rise,...
1 Bedroom Condo :: Oceanfront Resort Kapaa Shore
Green and peaceful Kauai is beauty personified, and this resort is an ideal base for exploring Hawaii’s oldest and northernmost island. And Kapaa is ideal for finding souvenirs handcrafted from local materials to bring back to your relaxing accommodations.This spacious...
The Pacifica Inn The Gecko and Volcano Room
Welcome to The Pacifica Inn located in Volcano on the Big Island of Hawai’i. The Pacifica Inn is a special little place out in the middle of the Pacific Ocean where you can experience peacefulness and tranquility. Come and enjoy the beautiful Hapu’u trees that surround...
Maui Resort Rentals: Honua Kai - Premier 7th Floor Penthouse, 4BR w/ Stunning Ocean and Black Rock Views!
This luxurious penthouse offering combines two of the finest residences at Honua Kai to create a four-bedroom pairing perfect for any large group or family. Konea 749 showcases stunning views of the Pacific Ocean, well above the tropical foliage of the Konea Tower...
Pahoa Home w/ Fenced-In Yard: Near Hilo & Parks
Washer & Dryer | 18 Mi to University of Hawaii at Hilo | 26 Mi to Hawaii Volcanoes National ParkBoasting a well-equipped kitchen, a lanai, and a furnished office, this 3-bedroom, 2-bath vacation rental has everything you need for your next extended stay in Pahoa. This...
Japanese Style Pool House - 1 block from the ocean
Aloha!Welcome to your haven of amenities and tranquility. Our unique home offers an unforgettable experience that will exceed your expectations. Whether you seek a romantic retreat, a family adventure, or a rejuvenating escape from reality, our property is sure to...
Ocean Views from Two Balcony Queen Suite / 1/2 Block to Waikiki Beach,
Legally permitted rental - 134 Kapahulu Ave #412** For your health and safety, we utilize additional Sterilization procedures between reservations.Simple, Charming and affordable - Sleeps 2Only 1/2 block from Waikiki Beach, and with one of the largest floor plans in the...
Garden view just steps from Maui's Sugar Beach
No Resort or Parking Fees!Hono Kai C12 is a bright 1-bedroom, 1-bathroom condo offering tropical views from the 3rd floor and traditional Hawaiian decor throughout. There are no elevators at this property. Unit C12 can accommodate up to 4 guests. The master bedroom...
Aston Kaanapali Shores #744: 1 Br Ocean View at Beach Front Resort
This condo in Kaanapali Maui is perfect for a small family or couple seeking comfort and convenience as this condo is located right next to the elevator, in a central location on the property. Watch the sun rise and set on the horizon from your large lanai with a...
Block to Beach! Waikiki Banyan Ocean View Condo with Free parking
Waikiki Banyan Tower 1 Suite 2310Deluxe Waikiki Condo Pool View FREE Parking & Wi-FiThe pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck renovation project. This 23st...
Refined Oceanfront Vistas
Summary:Spaciest & completely renovated oceanfront 1 bedroom, 1 bathroom top floor penthouse condo. Located in the sunny and vibrant beach town of Kihei. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy your day at the beach! We strive...
Maui Vista 1322: 1 Br Garden View w/Remodeled Kitchen & Bathroom Sleeps 4
Remodeled kitchen, and bathroom plus new flooring. This one-bedroom, one-bathroom, garden-view condo offers the simplicity of home in a tropical paradise. The master bedroom has a queen bed and the living room has a sofa bed, allowing this unit to accommodate up to four...
4th floor Marine Surf Studio with 2 queen beds
Perfect Waikiki getaway with a free assigned parking spot! This is the closest condo to the pool which makes it super convenient to start your day off in the pool, end your day in the pool, or even spend all day at the pool! Once you venture off property you are...
Wailea Grand Champions 116 - 1 Bedroom Garden View Condo
Wailea Grand Champions 116 is a luxurious vacation rental located along the southern coast of Maui in the desirable tourist area of Wailea. This beautifully appointed one-bedroom, two-bathroom condo accommodates up to four guests, making it ideal for families or groups...
High-Style Studio w/Kitchenette, Tile Floor, Flat Screen+AC – Waikīkī Grand #503
Castle at Waikīkī Grand #503: This air-conditioned 253sf studio is a perfect fit for active travelers and couples for their Hawaii vacation. Relax and unwind with such conveniences as WiFi, flat screen, and kitchenette for “at home” meals. Sleeps 2.Conveniently located...
Ground Floor Condo with Shared Pool & Hot Tub, & WiFi- Great Location
Maui Kaanapali Villas 191Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'It’s all about the vintage Hawaiiana in this sweet, ground-floor condo in Kaanapali! You’ve got plenty of...