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.
Island dwelling near the beach with pool, grills, & high-speed WiFi
Mahina Surf 210Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Live like an island local and kick back in style in this oceanfront condo just waiting to assist in making the best...
Hawaiian-inspired oceanfront Kaanapali penthouse
Papakea L401 is a 2-bedroom, 2-bathroom oceanfront penthouse corner unit that can accommodate up to 5 guests. The resort has an elevator to bring you to the 4th floor. The stunning unobstructed views of the Pacific can be seen from nearly every room. Inside you'll find...
Kapaa Shore Resort A106, Oceanfront, King Bed, Ground Floor, Comp Wifi
Kapaa Shore Resort Unit A106 – Oceanfront Paradise on Kauai's Coconut Coast Accommodates up to 4 guests, including children and infants.Overview: Experience the ultimate Hawaiian getaway at Kapaa Shore Resort Unit A106. This ground-floor, oceanfront retreat on Kauai’s...
Royal Gardens Waikiki - Sleeps 3 Full Kitchen
Legally permitted Rental440 ʻOlohana St, #1905A Five Star property under Brand New ownership May 2022A beautiful condo at the Royal Garden resort in Waikiki, a private large studio with renaissance flair the suite offers a full kitchen to assist in saving money whilst...
🏖️Great Ocean and Golf Course Views| No Stairs | vrKCV
vrKCV - Country Club Villas 241, Professionally Managed by Kona Coast VacationsExperience Stunning Pacific Ocean Views & ComfortWake up to breathtaking views of the Pacific Ocean and the 17th hole of the prestigious Kona Country Club Golf Course. This spacious and...
Kamaole Sands in Building 7 - Ground-floor unit in Kihei
You'll love our air-conditioned ground floor 1BR/2BA condo, centrally located in the inner circle of Kamaole Sands in Building 7, just steps away from the swimming pool, hot tub and the beach. The lanai opens out to a beautiful tropical garden with large grassy areas...
ICC 28 Remodeled 2BD Cottage in Kaanapali Walk to Beach and Pool
International Colony Club 28 NEW LISTING Experience Kaanapali from this Spacious Freshly Remodeled 2Bedroom, 2Bathroom, West Maui Cottage, Walk to the Beach and Pool! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of...
Garden view home with lanai, AC in every room, pool & tennis - walk to beaches
Hale Poipu NaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find a true getaway experience at Hale Poipu Nani, a beautiful, private home located in the Poipu Kai - Lanai Villas in...
Now This Truly is Maui!! Oceanfront & Pool views from lanai
An ocean front 1 bedroom ground floor paradise! This renovated maui condo rental is only minutes away from premier golf courses, spectacular beaches, the finest restaurants, and plenty of shopping. There is a great pool to relax around and a large sun deck with endless...
Gorgeous Greenbelt! Home with beautiful mountain views & 5 min walk from beach!
This four bedroom, three-bath home located in the Kauai Visitor Destination Area (VDA) is the perfect base for your next family vacation on Kauai. The house features two private master bedrooms and two additional twin bedrooms for children or guests. Bedding...
Ilikai-**New Listing*- Beautiful Ocean and Lagoon Views on high floor
The condo is a 1Bedroom 1bath newly renovated; made up of all stainless appliances, tile floors, California king bed, pull out sofa sleeper, 60" HDTV/DVD player, and air conditioning. There is a full kitchen equipped with a microwave, coffee maker, range/oven, double...
Great in town location for this 1 bedroom condo with ocean view
elcome to Kalanikai 208, a bright and comfortable 1-bedroom condo centrally located in Kailua-Kona Village. Positioned just one street above famous Ali‘i Drive, this condo offers the perfect balance of convenience, comfort, and island charm. Walk to beaches,...
Ilikai 1243 Best Views 2 Bed Room Best Ocean / Lagoon Views
FINEST OCEAN / LAGOON ! AT Ilikai WAIKIKI BEACH. 2 bedroom, 2 full bathrooms, 2 120 sq. ft lanais, 1,000 interior sq. ft. Walking distance to parks, shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life.This condo is in the "43" column which...
Discover Coastal Comfort: Oceanview Retreat at Kamaole Nalu #304
Kamaole Nalu #304 – Modern Ocean View Retreat in KiheiKamaole Nalu #304 is a beautifully remodeled two-bedroom, two-bathroom condo offering ocean views and modern island comfort. Located on the third floor of this oceanfront property, the condo provides an inviting...
Ultimate Oceanfront Townhome Located on Kona Coast
Wake each morning to the serene sounds of the ocean kissing the shoreline when you stay at this 2-bedroom, 2-bathroom Kailua-Kona vacation rental townhome. From this oceanside space, world-class snorkeling, parasailing, and whale watching are all at arm's length. If you...
KRL D302 Beautifully Updated Kaanapali 2BD on Golf Course wLarge Furnished Lanai
Kaanapali Royal D302 Beautifully Updated Kaanapali 2Bedroom on Golf Course with Large Furnished Private Lanai for Year-Round Indoor-Outdoor Living. Central AC, Pool, and More! FREE daily activities included with your stay value up to $570! Complimentary admission, every...
Extended Stay Panoramic Ocean & Diamond Head Views
Our unique quality listing features panoramic ocean and Diamond Head views overlooking Fort DeRussey park. Great location. Furnished as high end luxury recluse. Parking, wifi, cable, etc. You'll love it! We're looking for guest who would like to stay for 4-6 weeks or...
Fabulous condo, great ocean views, steps from a great snorkeling beach.
Prince Kuhio 302 is a fabulous condo with great ocean views just a few steps from a great snorkeling beach and an oceanfront restaurant that's perfect for a romantic evening including a colorful sunset. The Prince Kuhio complex features beautifully manicured tropical...
VI 204 Updated Coastal Chic OceanFront 1BD Ocean Views
Valley Isle 204 Updated Beach Chic OceanFront 1Bedroom at Perfect Location for Breathtaking Sunsets and Whale Watching. Relax and Recharge. Close to Famous Beaches and Dining FREE daily activities included with your stay value up to $570! Complimentary admission, every...
Dream ~ Exclusive Ocean Front Luxury Home on Wailea Bay, Beach 69 ~ Aina Malia
Summary:Aina Malia, a unique property, is situated above beautiful Wailea Bay on the Kohala Coast of the Big Island of Hawaii, one of the few white sand beaches on the island of Hawaii. Beautiful tropical landscaping abounds with privacy and romance. Custom designed...
Only 10 Feet from the Ocean! Fresh and Updated Pohailani 102 Studio - Sleeps 2
A short distance from sailing, scuba diving, and more, this smoke-free condo lets you experience it all. Thanks to the convenient onsite parking, you can either leave your vehicle behind and let your feet make short work of the 13-minute walk to Kahana Beach, or easily...
A Gem of a Studio at The Diamond Head Beach Hotel
Legally permitted vacation rental - 2947 Kalakaua Ave HI 96815A delightful well loved studio on Honolulu's Gold Coast nestled under Diamond Head.A comfortable Queen bed and a separate sleeper sofa in case it's needed await in this beautiful Diamond Head Beach Hotel...
Updated 2BR Paradise: A/C, Modern Luxury & Resort Amenities at Regency Poipu Kai
Escape to paradise in this newly updated, air conditioned, 2-bedroom vacation haven nestled within the prestigious Regency at Poipu Kai. This tropical retreat promises a perfect blend of modern luxury and Hawaiian charm, providing an unforgettable backdrop for your...
BBQ Grill on the Lanai! Waikoloa Beach Villas I3
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas I3Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Two Twin BedsAdditional Bedding: Sleeper Sofa in the Living...
OCEANFRONT - BREATHTAKING! PONO KAI Condo!! 2bd2bth! Washer/Dryer/AC
WAKE UP TO BREATH TAKING KAUAI SUNRISES AND OCEANFRONT VIEWS from the MASTER BEDROOM, LIVING/DINING ROOMS and KITCHEN!! This Beautiful 1200 sq/ft. Pono Kai Condo directly in front of the ocean and the beach...and furnished in traditional Island decor for a true Aloha...
Villas By The Cove, Villa 5 · Exquisite Ocean View Villa with Pool across from the Beach
Villa 5 at Villas By The Cove is a spacious 1 bedroom Villa Suite that boasts 180 degree ocean views from the living room and covered lanai. Newly remodeled, and conveniently located, this 700 sq. ft. 1 bedroom villa offers privacy and comfort set back in a tropical...
Heart of Waikiki studio with kitchenette, AC, FREE parking & Wi-Fi!
Marine Surf #1204 – 364 Seaside Ave.This cute studio (392 sqft plus lanai) with AC and kitchenette, will comfortably accommodate the needs of vacationers or a corporate traveler. It's just a short walk to the best swimming and surfing beaches! Shopping, restaurants, and...
Upgraded 3BR Corner Unit with Golf Discount: Quiet building, Open Lanai.
Welcome to Hali'i Kai at Waikoloa Resort, discover the captivating allure and serenity of the sunny Kohala Coast on the magnificent Big Island. Embrace the renowned Waikoloa Resort as you embark on a journey to Hale Pikake at Hali’i Kai 2H.Enjoy the serene Coconut Grove...
Comfortable Poipu lodging with a lanai overlooking the ocean.
Comfortable Poipu lodging with a lanai overlooking the ocean - so close you can hear the surf! Grab your swimwear, sun glasses, surfboard, sandals, and snorkel and get ready for Poipu on Kauai, the Garden Island. Kauai will make your vacation a tropical Hawaii dream....
Sunny Ground Level On Courtyard~ Great View & Right Out To The Beach! Unit #111
Enjoy the ocean view and listen to the gentle surf from our attractive ground floor unit that has landscaping and privacy from lanai.. Our spacious one bedroom/ two full baths is located on beautiful Kaanapali Beach and considered to be 'the signature beach of West...
Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates.
This charming property has been kept the same since the original build to keep the "sugar plantation" style of the old Hawaii days. No major upgrades have been made to keep an old Hawaii days feel. The RATES REFLECT the style accordingly. This home is perfect for...
❤️PiH❤️ HAWAIIAN BLISS ★ Beach Gear, Bikes and family fun!
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hawaiian Bliss Villa, part of our Hawaiian Luxury Collection. We pride ourselves on offering some of the most sought-after homes on the Kohala Coast, and we're delighted to include this spacious, beautifully...
Affordable Kailua Kona Vacation Condo! Summer Special!!
Welcome to Kona Pacific E735 – Your Island Escape in the Heart of Kailua-KonaPerched on the top floor of the Kona Pacific complex, this spacious 2-bedroom, 3-bathroom condo offers the perfect blend of island charm, comfort, and convenience — all at a fantastic value....
Pono Kai Unit C101 - Oceanfront, Ground Floor Unit, Steps to the Ocean, AC
Pool Area Closure: January 6 to January 31, 2026. The Kapaa Pool is less than a mile from the resort and Lydgate Beach ponds for swimming and snorkeling is 3.4 miles South of the resort. Discounts are automatically applied for these dates.Pono Kai Resort C101,...
WaikikiLux 507 Waikiki
Right in the heart and excitement of Waikiki Our side by side suites are perfect for family, friends or business associates traveling together with everything you need just outside your doorstep. As always at the Lux, all amenities are included: First Class Fully...
Discover Ma'alaea Banyans: Ocean Views, Beach Access, and Perfect Maui Getaway!
Don't miss your amazing opportunity to soak in Panoramic ocean views mere steps to the beach! Ma'alaea is a hidden gem on Maui waiting to be discovered for your perfect Maui Vacation!Welcome to Ma'alaea Banyans, home to panoramic views of the majestic Pacific Ocean,...
Kamaole Sands across from beach/entertainment
Great location! Near beaches, shopping, entertainment and restaurants. About 20 minutes from the airport. 15 minutes to Maui Ocean Center. 40 minutes to Lahaina. Take the Piilani Highway and you'll be on your way to Road to Hana and Haleakala. So pack your suitcase and...
Legal Short Term on Golf Course, Upper Floor - Have a relaxing vacation in Oahu
What news you have read or heard - There are Legal Short Term Rentals in Hawaii.We are on the short list on the North Shore at Turtle Bay.This a Family Owned and managed Home. It's is hard to get a more perfect view of the golf course from the lanai of this two bedroom...
Last Min rates direct!Spectacular Oceanfront Corner Groundfloor,Steps To Ocean!
If breathtaking oceanfront views are what you are looking for in an oceanfront resort, then look no further! This is exactly where you need to be to make your lifelong memories.Condo is secluded and quiet, just steps from the Pacific Ocean and is an ideal location that...
Beautiful Ocean view of Sunny South Shore at Poipu Beach in Kauai
1 bedroom 1 bath vacation rental located in the beautiful town of Koloa, Hawaii. This cozy and comfortable unit is fully furnished and equipped with all the amenities you need for a relaxing and memorable stay.The bedroom features a comfortable queen-size bed,...
RENOVATED! Ocean View, FREE PARKING, Central AC, Pool, Quick Walk to Beach!
Waikiki Park Heights #1707 – 2440 Kuhio Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy the comforts of home and gorgeous ocean views from this beautifully renovated 1-bedroom condo (488 sq. ft.). FREE Parking on site for 1 vehicle, which...
Maui Sunset Vacation Rentals B212
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. New Flooring throughout 2023. Second floor means easy access to tropical gardens and the ocean beyond. Quiet...
Gorgeous Waikiki Ocean View! Full Kitchen, Free Parking, Close to Beach!
Waikiki Sunset #3704 – 229 Paoakalani Ave.Fabulous views of the Pacific Ocean, Diamond Head and Kapiolani Park from this 37th floor, one-bedroom condo (564 sqft plus 67-sqft lanai with table and chairs) with central AC. 4-person max.Just a 10-minute walk to the best...
Partial Ocean View! Toto Washlet, FREE Parking, Washer/Dryer, Wi-Fi! Sleeps 4
Four Paddle #1703 – 2140 Kuhio Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)This 17th floor studio (460 sf plus lanai) with central A/C and ocean view makes this condo a favorite with our guests! 4-person max.Gourmet marketplace Dean & DeLuca...
Highly desirable, Ilikai Hotel, Yacht Harbor & Ocean view, Reserve Today, Will not last Long!!
This condo is located on the 14th floor of the Ilikai Hotel. Enjoy stunning sunsets from your private lanai. This beautiful condo has fresh paint, new drapery, split AC & it desirable by many travelers as it has a full, direct and unobstructed ocean views, overlooking...
Ocean View Oasis with Free Parking: A Waikiki Gem!
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...
Views, romantic and private with king bed, ground floor convenience
Sealodge G4 is the perfect Sealodge Kauai condo for honeymoons, anniversaries, or other romantic occasions. With its expansive views of the sea, waves breaking, and lush green coastline visible from the large bedroom picture window, you won't even need to get out of the...
New 1 Bedroom with Great Views, Kitchen & Den
Beautifully Remodeled and updated October 2022 with great touches! This 8th floor suite at The Diamond Head Beach Hotel already offered great views and perfect location for a relaxing getaway. New owners added the rest to ensure the condo is the perfect place to call...
Cozy Hawaiian studio just minutes to the beach and town. No minimum stay
Want to be close to a beautiful beach and the little fishing village of Kailua Kona? If so this place is for you. Magic sand is just 1.2 miles away where you can body surf/body board, sunbath, eat at the beach grill or grab a shave ice. Center of Kailua kona is only 2...
Stylish Condo w/ Mountain Views in Waikiki Banyan!
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...