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.
Hale Nani: New Poipu Villa- Pool/Spa + Ocean Views
Breathtaking, sensational, divine. It’s impossible to overstate the appeal of this exceptional villa, with its spacious, elegantly appointed rooms and gorgeous grounds set against a dazzling backdrop of palm-fringed golf course, dramatic mountains, glittering ocean,...
Jewel Villa in Ko Olina Resort
This newly renovated, luxurious Villa is nestled in the quiet resort of Ko Olina. This Villa has 3 bedrooms and can sleep up to 6 guests. Choose to spend your days on the Ko Olina Championship golf course, one of the four lagoons on the beach, or eat at any of the...
Paradise Awaits in this Luxurious Villa in Ko Olina
Luxurious 3 bedroom Villa located in West Oahu. Enjoy all 4 of Ko Olina's ocean lagoons. Walking distance to Four Seasons, Disney Aulani, Marriott Beach Club, Ko Olina Center (shops and restaurants), Ko Olina Golf Club, Roy's Restaurant, and Monkey Pod Restaurant.State...
SPECTACULAR OCEANFRONT PENTHOUSE-Air Conditioned 3 Bedroom/3 Bathroom, Full Gym
Poipu Makai B3 is located on a bluff a couple of yards from the water with stunning, full uninhibited views of the ocean. Enhance your senses – the visual beauty of the waves crashing against the shoreline and the gentle sound of the living and breathing sea. Spend...
87-1 Escape to Paradise at Puamana's Hale Nalu
Welcome to Hale Nalu, a beautifully updated townhome in the tranquil Puamana community just south of Lahaina. This 30-acre private paradise offers a peaceful retreat away from high-rise hotels and crowded tourist areas, yet remains close to world-class beaches and golf,...
Fully Renovated Unit. 3 Bdrm, 3 Bath Sleeps 8. Perfect for Grandparents
Beautiful 3 bedroom 3 full bath in Keauhou's newest complex. Na Hale O Keauhou is the most sought after rental because you get resort style living right in the heart of Keauhou. H6 is located in the most private location with no pool or traffic noise from this unit. You...
Includes Beach Gear! Spacious lanai with resort views. #2 Shores at Waikoloa
This vacation rental is professionally managed by ResorticaHawaiiShores at Waikoloa Villa 2Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: 2 Queen BedsAmenities:Beach Equipment: All of our vacation rentals include...
Hilton Pool Pass thru 2025. Golf Discounts. Waikoloa Beach Villas L2
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas L2Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: One Queen BedLiving Room: Sleeper SofaHilton Pool Pass: Valid for stays now...
Molokai Shores Resort Condo w/ Pool & Views!
Set sail to Molokai and book an unforgettable stay at this Kaunakakai vacation rental. The 1-bedroom, 1-bathroom tropical condo, located in the Molokai Shores Resort community, boasts access to the year-round outdoor pool, shuffleboard, picnic areas, and 4 acres of...
LUXURY 2-Bed Condo, Kitchen, Wi-Fi, Parking, W/D, AC, LEGAL Monthly Rental!
Allure Waikiki #804 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! Max Stay 3 Months. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...
Monthly- Discovery Bay 2203 Ocean/Sunset/Marina/City Views - Q Bed/Twin Sofabed
Sweeping Ocean Views High Floor Corner Unit, PremTV HBO, Remodeled. 5 Min to Beach, Ctrl AC, Furnished, Prking Incl, Spacious Lanai, Pool, HotTub, Utilities, WiFi, BBQ, Gym, Washer/Dryer, Beach Chairs/Boogie Board. Non smoking. Queen bed/Queen Sofabd.Sweeping Ocean...
Cozy Oceanfront 2BR Condo with Pool and Epic Views
Summary:Embrace the ultimate Hawaiian escape in this stunning oceanfront condo, meticulously remodeled to capture the luxurious yet laid-back essence of Maui. Enjoy breathtaking views as sea turtles gracefully swim by while you sip your morning coffee on the private...
Aloha Condos, Kanaloa at Kona, Condo 2204, Oceanfront, AC
Kanaloa at Kona Condo 2204 is a dream! With breathtaking ocean views and luxurious amenities, this condo exceeds expectations. Guests love the well-appointed kitchen, comfy furnishings, and thoughtful extras like beach gear and toiletries. The lanai is perfect for...
ALA 12 Perfect Getaway Remodeled Private 4Bedroom Beach House Near Beach
Alaeloa 12 Beautifully Remodeled 4Bedroom Beach Home with Stunning Ocean Views and OceanFront Pool in Napili Bay. Idyllic Peaceful and Relaxing Winter Retreat Professionally managed by Maui Paradise PropertiesAlaeloa 12 is the perfect getaway for that extended stay. Ask...
Beautiful Kealakekua Home w/ Spectacular Ocean View
Located approximately 10 miles south of Kailua-Kona is your Hawaiian home while visiting visiting us here on the Big Island of Hawaii. Arise in the morning and enjoy a freshly brewed cup of Kona coffee while planning your adventures for the day. You are just minutes...
Alii Cove J-4 - Beautiful upgraded Townhome at the top of Alii Cove overlooking the ocean.
Alii Cove unit J-4 is located at the top of the complex in historic Kailua Village and offers the best Kona Coast ocean views you can get from Alii Cove. This 1815 square foot end unit has been fully upgraded and is well equipped with everything you need to get...
Oceanfront: Amazing Location, Steps to the Beach! Split AC, Pool, King Bed
Aloha from Sea Breeze at Menehune Shores! Our remodeled 2 bedroom and 2 bath oceanfront condo in South Kihei’s Hotel Zone offers breathtaking ocean views from the 4th floor. Enjoy direct beach access, a pool, and a kid-friendly lagoon perfect for swimming. The condo...
RK 301 Remodeled OceanFront 2BD w Pool and AC
Royal Kahana 301 Spacious & Beautifully Remodeled 2BR With Gorgeous Ocean View Look no further for the Maui vacation home of your dreams! Our newly renovated and spacious condo offers all you need to make lasting memories in comfort and style. The open floor plan has...
Kihei Surfside 214 - 2 Bedroom-2 Bath Luxury Oceanfront Property with AC
* Accommodates up to 6 people! * Air Conditioned.* Great condo in a great location. * This ocean front condo has been upgraded. * Unobstructed ocean view - 150 feet from the ocean - Watch the whales from your private Lanai. * 100 feet from one of the finest beaches in...
Modern 2BR/2BA w-A/C, Sleeps 6, Walk to Beach, Spacious, Prime B Bldg Location
Absolute Serenity awaits you in Maui, Hawaii. This air-conditioned, two-story, fully-equipped condo, sleeps six and has plenty of space for your family, plus hotel-style amenities that include access to two swimming pools, hot tubs, and tennis courts. Our recently...
Oceanfront with A/C Remodeled Amazing Views of Whales
Relaxing and Lovely Property on the Ocean, with Both Ocean & Garden ViewsThe condo provides a great ocean view and oceanfront location that keeps all the traditional Hawaiian Charm and feel in a low rise.. We have lush plantings and gardens, cool trade winds, and sounds...
KPL 58 Spacious 2BD Plantation Home Near Beach
Kaanapali Plantation 58 Spacious 2Bedroom Condo, a Minute Drive from Kahekili BeachFREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm...
Pikake ocean front 20 feet from ocean
First floor corner unit at The Pikake. Extra windows for extra breezes. Senior & kid friendly. Able to watch turtles, whales, and sunsets from the lanai. Steps from the beach. No extr Only 12 units in complex. 1 parking space for each unit.
Maui Resort Rentals: Honua Kai Hokulani 814 - Top Floor 1BR w/ Partial Ocean & Mountain Views!
This beautifully appointed top floor "penthouse" suite boasts one of the best one-bedroom locations available at Honua Kai. Enjoy generous partial ocean views from the balcony and primary bedroom in addition to great views of the verdant West Maui Mountains. This suite...
This exquisite three-bedroom oceanview residence boasts epic views of the Pacific Ocean from its premier 9th-floor vantage point, well above the tropical foliage of the Konea Tower interior courtyard. The views are abundant throughout, continuing into all three...
Hale Anuenue By Parrish Kauai - AC & walk to Poipu Beach!
Perched on the rim of Poipu Crater overlooking Poipu Beach to the west and Mount Haupu to the east, Hale Anuenue ("house of rainbows") offers the perfect spot to see rainbows when the skies offer liquid sunshine. Positioned for views of the morning sunrise glow over the...
🏖️Updated Townhome | Ocean View | vrKCV🏖️
vrKCV - Na Hale O Keauhou D3, Professionally Managed by Kona Coast VacationsWelcome to Your Perfect Home Base in Na Hale O Keauhou!Experience the charm of this beautifully updated townhome in the serene and highly sought-after Na Hale O Keauhou complex. This gated...
Maui Resort Rentals: Honua Kai Hokulani 738 - Luxurious 1BR w/ Partial Ocean & Mountain Views!
Hokulani 738 is a luxurious 7th-floor one-bedroom suite that offers views of the tranquil blue Pacific Ocean as well as views of the lush West Maui Mountains. You will have plenty of space to relax in the 700 sq ft interior. To fully enjoy the warm Hawaiian breeze, fold...
Ground floor villa - 1-minute to the beach
Kahana Villa E111 is a 2-bedroom, 2-bathroom ground-floor condo that offers an open-concept layout and partial ocean views depending on your location inside. Unit E111 can accommodate up to 6 guests. Walking into the upstairs master bedroom, you will find 2 queen-size...
Beautiful Luxury Garden View 2 Bedroom, 3 Bathroom Condo
Beautiful Luxury Garden View 2 Bedroom, 3 Bathroom Condo at #1 Rated 1st Class Waipouli Oceanfront and Beachfront Resort & Spa on the beautiful island of Kauai. This exceptionally, well decorated ground floor 2 Bedroom, 3 Bath Condo offers easy access to the pool and...
Konea 713 is among the most sought-after two-bedroom floor plans at Honua Kai. What distinguishes this column in the Konea interior is the direct ocean views from virtually every interior vantage point of the suite. This premier two-bedroom boasts a spacious 1325 sq ft...
Private Oceanfront Top Floor Condo - Kona Reef D34
NEW OWNERS! NEW UPDATES AND IMPROVEMENTS! Welcome to our private and comfortable ocean front condo in paradise - Kona Reef D-34. As soon as you arrive to our very private top floor ocean front condo located on the romantic coastline of the Island of Hawaii you will...
PoipuBeach-3rdFl-Partial Ocean- AC-Pool-Garden-313
Private top-floor corner unit in a peaceful building with AC and upgrades—tons of privacy! Enjoy access to the pool, stroll through lush Moir Gardens to reach Kiahuna Beach, and skip the resort fees. Beach gear is included for your convenience. This serene retreat is...
Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across...
Summary:This beautiful and stylish remodeled home is perfect for group or couples vacations! You will be very comfortable in this large and upscale 2 bedroom 3 full bath home that is completely renovated!We are located in the Kapalua Ridge Villa Community. Only a 6 min...
Romantic getaway directly on Napili Bay-Beachfront-5 Stars-Best Location
Fall head over heels for the enchanting Napili Bay at "The Aloha Bungalow," a newly renovated ground-floor beachfront studio condo overlooking the turquoise waters of one of Maui’s most beloved beaches. Nestled in the heart of Napili Bay with its soft, golden-sand beach...
Ground Floor Luxury, Perfect Family Spot, Quiet Lanai to Pool/Beach in 1 Minute!
Konea 106, Honau Kai Resort, is a fabulous ground floor unit (2 Bed/1 Bath) located at the center of the resort on the quiet side with a private lanai. Our lanai extends out to an open grass area which many of our guests use to relax, play games, or sit and enjoy the...
Fabulous Ocean & Diamond Head View with 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...
Luxury Condo in Wailea with sweeping views
2 large master ensuite bedrooms with Cal King beds. Sweeping views of Kaho'olawe, Molokini, and Lanai islands and spectacular sunsets. Beaches, restaurants, and Shops of Wailea all within walking distance. Fully equipped kitchen, with plenty of dining wear and cooking...
Ocean Front Condo with Endless Sunset Views
Welcome to Paradise! This bright, newly renovated condo will capture your heart and elevate your appreciation for the tropical heaven that Waikiki is known for. When walking into the unit, you’ll feel as if you’re on your own tropical island as you’re surrounded by...
UPGRADED-Oceanfront-3 BR-Sands of Kahana-Central AC.
Hotel Zoned!! Safe and Protected Stay! Book with Confidence. We offer Cancel for Any Reason Travel Insurance! Sands of Kahana unit 275 on the 7th floor in the ocean front building 2. Location, location, location! Located between Kaanapali and Kapalua you will the quaint...
Island Breeze Oasis - Newly Furnished
Welcome to our slice of paradise! Prepare for a vacation that feels like a dream – our villa is not just a place to stay; it's an experience waiting to unfold!Imagine waking up to the sun-kissed charm of four stunning lagoons right at your doorstep. These crystal-clear...
A Beautiful Ocean Front Resort Condo!
Waipouli Condo A101 is a large 1 bedroom, 2 bath condo with Central AC. Located in Kapaa Town, walk to shops, restaurants and beaches. Complimentary Wifi & on site parking, King bed and queen sofa sleeper, washer/dryer in the unit. Comfortably Sleeps 4.The space...
Kona Isle B34 - Ocean View, Top Floor with full AC. Peaceful Oceanfront Complex.
NEW: In an effort to provide you with outstanding accommodations, we have upgraded to a dual-air conditioning unit that allows for whole-unit AC. We've also upgraded to quartz countertops! Aloha from Hale Malina! We invite you to enjoy a little piece of paradise, which...
Ocean View Close to Airport & Beaches
Conveniently located just minutes from the airport & white sandy beaches and 10-15 minutes to the heart of Kona town, this vacation home has everything you need for a truly memorable stay in paradise! This rental is the upstairs unit of a two unit home with its own...
Spectacular Kaanapali Beach Front Vacation
Sweeping views of Lanai and Molokai from the top floor wraparound lanai. This treasured beachfront Villa is truly a home-away-from-home. We provide comfortable accommodations right on the beach. Gaze through the sliding glass doors or step out onto your oversized...
Newly Renovated Condo - Next to the beach!
This 1 bedroom unit is equipped with everything needed for an unforgettable vacation experience. Enjoy the ocean views and sunsets while relaxing and sipping on a glass of wine from the balcony/lanai. The condo is perfect for couples looking to take a break and enjoy...
Remodeled Oceanfront I Royal Mauian 509
Welcome to your perfect Maui getaway at Royal Mauian Unit 509! This beautifully designed, fully remodeled 1-bedroom, 1-bathroom oceanfront condo is located in the vibrant Kihei area, just steps from the stunning beaches and local attractions. Ideal for couples or solo...
Simply Stunning Condo, C202 is one of of the best!
A LITTLE ABOUT THIS CONDO... Lokelani C202 - Welcome to our coastal paradise on West Maui. This newly remodeled and updated oceanfront condo, just 45 feet from the Pacific, offers stunning views of Molokai, Lanai and Hawaiian sunsets from within and from its two...
Huge Home with Pool, Jacuzzi & Water Slide! Sleeps 18!
Affectionately named “The Pool House” by our 4 little ones, this house is above and beyond its typical name sake. This sprawling 3,000 sq.ft. home boasts 5 bedrooms and 5.5 bathrooms, with room to sleep at least 18 comfortably. A sleek modern kitchen, outdoor grill, 2...