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.
Relaxing haven, ocean view in the heart of sunny Poipu, Sunset Kahili 408
This spacious two bedroom Sunset Kahili condo with an expansive ocean view is decorated with tasteful island decor throughout. Bedrooms are comfortably furnished and condo includes a full kitchen complete with stove, oven, refrigerator, dishwasher, and microwave.The...
Ocean View KAN405 - Maui - Ma’alaea Condo Great Views and Value 2BR/2BA Sleep
Experience the ultimate beachfront getaway at Kanai A Nalu Resort 405, where this charming condo awaits to provide you with a truly memorable vacation. Nestled in a secluded spot, this hidden gem offers a serene escape with breathtaking ocean views and a range of...
KONA MAKAI#5-205 BEAUTIFUL 2ND FLOOR UNIT IN OCEANFRONT COMPLEX!
Kona Makai#5-205 is a fantastic option for your Hawaiian Vacation. Gorgeous Luxury Vinyl Plank Flooring Installed throughout Living Areas/Bedroom. No Carpet! This beautiful 2nd floor unit is located in a very accessible spot of Building#5 at the Kona Makai. Don't have...
Special for monthly rentals $2320/month- perfect for Dr/Nurses/prof.
Aloha & welcome to Honu Hale, your home away from home, where the Hawaiian sea turtles throughout the home will not only bring you good luck, but according to Hawaiian legends will serve as guardians throughout your stay. Our home sleeps 4, with one queen and one double...
BEST LOCATION in Kihei! 1BD/1BA by the BEACH! A/C, Clean, Cozy, Wifi, Beach Gear
Legally zoned vacation rental unit. We are completely hands on and have been in the business since 2008. Communications will be directly with us and we operate with a valid State of Hawaii license 091-649-8432-01.A new 55 inch Smart TV and split AC system just...
Ground Floor Corner Unit In Close Proximity To Beach And Downtown Kihei.
If location is everything, this condo is location GOLD! Our 2-bedroom Kalama Terrace condo is located on a quiet street just off the main strip. You feel secluded and at home - meanwhile, you are a short walk from downtown Kihei. Our entire condo was recently remodeled...
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...
Kuleana #303: Oceanfront Gem with King Bed and Pool plus Summer Rates!
Kuleana #303! Oceanfront Community! Prime location for island adventurers. This ground floor condo has all the comforts of home with a bright, beachy vibe. Cozy open living space features large tile floors that help keep your space nice and cool. Bamboo cabinets and...
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 and the beach. The lanai opens out to a beautiful tropical garden with large grassy areas and water...
Hanalei Colony Resort #G-1 - Ocean front condominium in Wainiha/Haena
Beautifully renovated from top to bottom in 2024, this condo is everything you could want with a view to match! Hanalei Colony Resort #G-1 has a semi open floor plan with one bedroom plus an additional sleeping nook. There is sleeping for 4 people and 2 full bathrooms....
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
Kalanikai 208 is situated in the heart of Kailua-Kona Village amongst lush tropical landscaping. This is one street above Alii Drive and walking distance to stores, restaurants, the ocean, beaches, Starbucks and the new Safeway located directly behind us. This one...
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...
Little Paradise in Waikiki with Lovely Ocean -15th FL
Your convenient cute little place with a beautiful ocean view! Our unit overlooks Fort DeRussy Beach Park, right across from Hilton Hawaiian Village. There are so many restaurants, and beaches around. 1 block from Waikiki Beach and also close to Ala Moana beach. Walk...
15% Off Stays thru 5/31/25! Perfect Family Getaway! Ground Floor, AC, Pool 2B/2B
Experience the ultimate Maui getaway at Kaanapali Royal L101, a spacious ground-floor condo offering nearly 1,900 square feet of comfort and style. Perfect for families or groups, this beautiful two-bedroom, two-bathroom retreat comfortably accommodates up to six...
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...
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...
Poipu Makai C-2 ... Breathtaking sunsets and Views of the Ocean
This beautiful, privately owned condominium is absolutely perfect for the Kauai-bound traveler. Here you can greet and close each day from your private lanai with spectacular ocean views. The Poipu coastline. Spouting Horn. The island of Niihau. Breathtaking sunsets....
🌴Kona Isle B8 This corner ground floor unit is private and quiet with a pleasing beach theme🌴
Kona Isle captures the very spirit that defines Hawaii with its beautiful tropical gardens, private beach,and ever-present tropical ocean breezes. Come lounge under the palm trees and watch the dolphinsand whales at play, enjoy swimming in the solar-heated pool and...
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...
BBQ Grill on the Lanai! Waikoloa Beach Villas I3
**Complimentary Late Check Out up to 7:00pm for stays of 5 nights or more between October 1-December 19, 2025 (stay must be complete by December 19th) based on availability at the time of booking. Valid for new bookings made September 24 or after. Please message us...
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,...
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...
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 at KaMilo is a wonderful 4 bedroom home, part of our Hawaiian Luxury Collection.We pride ourselves on providing some of the most sought after homes on the Kohala Coast and are thrilled to...
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...
Maui Resort Rentals: Ka'anapali Ali'i 151 - Luxurious 2BR w/ Partial Ocean Views!
Suite 151 is a luxurious 2BR suite offering partial Pacific Ocean views from the balcony, living room, dining room, and primary bedroom. As added highlights, your group will be treated to views of The West Maui Mountains and Kaanapali Beach views that extend all the way...
❤️PiH❤️Adventure Awaits Villa ★ Private Pool ★ Free Hilton Resort Passes ★ Beach Gear and Bikes
Brought to you by Paradise in Hawaii Luxury HomesWelcome to the new and elegant home, Adventure Awaits Villa, in our Hawaiian Luxury Collection. Adventure Awaits Villa is a beautiful single-level 4 bedroom, 3 bathroom home. This home has a private pool with spa and...
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...