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.
Grand Champions 105 I Spacious Wailea 3bd
Hawaii Life Vacations proudly presents Grand Champions #105, a beautifully updated 3-bedroom condo located in a serene corner of Grand Champions Villas in Wailea. Nestled against the 8th hole of the Blue Course, this spacious retreat offers stunning mountain views from...
Beautiful Beaches ⛱ and Sunshine 🌞 Top Floor Ocean View 😎
Waikoloa boasts sunny days while the views from E304 never cease to amaze! As you enjoy your morning coffee or evening cocktail from your (381 square feet ) large lanai, you will have great views of the Anaeho'omalu Bay (A-Bay) and Hualalai Mountain (another currently...
Kauna‘oa 4BR Oceanview Villa with Pool, Spa & Mauna Kea Resort Access
Summary:Experience elevated island living in this luxurious 4-bedroom, 3.5-bath duplex home, located within the prestigious Kauna'oa at Mauna Kea Resort. Just a short walk to the pristine Kauna'oa Bay, this stunning residence offers an exquisite blend of indoor-outdoor...
The Perfect Relaxation & Beach Destination
Our lovely Nihilani Home is situated ideally in the center of the complex, far away from the noise of Ka Haku Road and just steps to the swimming pool and barbecues. And good news, there is now wireless at the pool! This 2,200 SF, 2 story home has undergone a...
Lanikai Ocean Front Duplex Bungalow Private ocean steps. Contact for rates/avail
Location Location Location! Our Lanikai ocean front location exactly in front of the twin Mokulua Islands provides endless hours of outstanding views from the ocean front yard, the living room, dining room, and side deck. A perfect place to work remotely, as you have an...
Peaceful Paradise
New modern studio located between the east and north shore of Kauai. Close to Anahola bay you may hear the calming sound of the ocean at night. Fronting the property is the heavenly Kalalea mountain. The Studio includes A/C, 75 inch flat screen TV, Internet , cable,...
Kailua Oceanfront Villa with Heated Pool & Spa - availability Sept, Oct & Nov
Relax in the beautiful three-bedroom seaside villa in Kailua, where soothing sea waves and soft breezes carry you off. Indulge in the outdoor pool, where you can soak up the sun and relax and end a day of hiking or golf with a massage in the oceanside hot tub. Stay...
Luxury Beachfront & Oceanfront Condo with Panoramic Views • Legal Rental
Looking for the Best Hawaii vacation rental in Maui? Enjoy amazing Maui beachfront views of the Pacific from this spacious, beautifully furnished 7th floor one-bedroom condo at the Mahana on Ka'anapali Beach, rated by TripAdvisor at #1 in the USA and #4 world in...
Hawaii Life Rental Presents Emmalani 423
***Please see construction disclosure at the bottom of the listing.Located within the beautiful Emmalani Court complex on Kauai’s North shore, here you will find yourself surrounded by lush tropical foliage, nearby to breathtaking ocean vistas, world-famous golf Makai...
Hale Manulele near Hanalei
Enjoy our private home in a family friendly, quiet neighborhood on the North Shore of Kaua'i, where the trade winds breeze across the lanai and through the family size house , where bird songs fill the air, and the cloud shows, mountain views with waterfalls, rainbows,...
OCEANFRONT TWO BEDROOM CONDO at SEA VILLAGE with A/C in ALL ROOMS!
Imagine - warm tropical climate, views and sounds of the ocean just out your door, panoramic views, and the perfect accommodations - is there anyway else to experience Hawaii? This two-bedroom, two-bath condominium gives you all of that and more! Comfortable set up with...
Fully Renovated Studio in the Heart of Waikiki – A/C, Wi-Fi, FREE Parking!
Marine Surf #2207 – 364 Seaside Ave.Beautifully furnished contemporary 22nd-floor studio in the heart of Waikiki, fully renovated in January 2025, complete with resort-style kitchenette, comfortable Queen size bed, A/C, free high-speed Wi-Fi, and 1 free onsite parking...
Luxury Nohea Home with Pool & 2 Adjoining Ohanas
Abita Luxury Rentals welcomes you to escape to paradise at this 3,000 sq ft, 4-bedroom luxury retreat in Nohea at Mauna Lani. Thoughtfully designed for comfort and style, this home features a private backyard with a pool and spa, surrounded by lush greenery for a...
Recently Remodeled, Modern, Nice Condo in a Great Location
One bedroom, one bath condo with a great walk in shower. Nice kitchen to save money and prepare your meals. Large tv, fast wireless internet, full size in unit washer and dryer, and a free parking stall. Nice lanai to enjoy your morning coffee, and ac in the unit....
Gorgeous Kapalua Home with Views
This gorgeous Maui home is a two story end unit with expansive ocean views from lanais on each level! Located in the renowned Kapalua resort area on the northern coast of Maui, you are not only close to the beach (less than a 5 minute walk, to be exact), but within...
Aloha Charm on Maui's North Shore - Right by Mama's Beach.
2 rows off the sandy beach in a quiet north shore neighborhood. This property is perfect for family and friends or a couple. 'A breezy and charming home, Maui Winds invites rest and relaxation and offers exciting activities for top-notch athletes ready to windsurf,...
Gorgeous Gated Retreat Near Ocean w Pool & Deck!
Enjoy a blissful vacation at the Heavenly Hawaiian Paradise Beach House. This 3BR/2BA retreat is perfect for groups up to 10, offering welcoming spaces both indoor and outdoor to dine and relax in the beautiful Hawaiian weather. Spacious outdoor deck with swimming pool,...
STUNNING FAIRWAY VIEWS, HOME "E"-CLEAN-NEW-GATED, NEAR JBPHH, CAGE # AVAILABLE.
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, air conditioned executive home located in central Honolulu. Perfect for leisure visitors, savvy business travelers or visiting construction crews with each...
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
Charming beachfront cottage right on Kailua Beach! licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage. This delightful 2 bedroom/1 bath vacation rental cottage puts you right in the middle of world renowned Kailua Beach. Enjoy ocean views from your living room....
Luxury 1BD in ONE ALA MOANA with Beautiful View and Room with Free Parking!!
One of the most luxury condominium in Hawaii. You can experience the best vacation ever in One Ala Moana!!The minute you go inside, you will be astonished the amount of light coming through huge ceiling to floor windows overviewing the city and the mountains. The fully...
Tropical Acreage + Fruit Trees + Beach ~5m drive!
Welcome to "Pua Pono House," on Oahu's captivating North Shore, where country living meets relaxation, away from the hustle and bustle of Honolulu and touristy hotels. Nestled on a lush one-acre estate, our retreat offers a serene and secluded oasis. Centrally located...
Ho'olei Villa 17-1: Luxury Retreat with Breathtaking Ocean Views
This property is hotel zoned, and not being affected by the recent proposed legislation.Luxury at its finest! Ho'olei Villa 17-1! Mesmerizing ocean views and bright open floor plan welcome you. Enjoy the beautiful Maui sunsets on your expansive private lanai.One of the...
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View
Waipouli Beach Resort E301 2 Bdm, 3 Bath - Beautiful Sleeping Giant Mtn View and Peek Oceanview!SLEEPS UP TO 7! This Luxury Condo Offers Guests a Gorgeous View of Sleeping Giant Mountain and peek ocean view from the lanai. This Condo is a 2 Bedroom, 3 Bathroom Condo at...
Hale Malulani - Luxury Oceanfront Puako Villa with Pool, Hot Tub & Pickleball!
Immerse yourself in the unparalleled luxury and breathtaking beauty of Hale Malulani, an exquisite oasis nestled in the serene shores of Puako, now gracing the rental market once again, following a meticulous and extensive renovation. This exquisite property proudly...
Penthouse Waipouli Beach Resort E404 - Beautiful Ocean & Pool View
Penthouse - Ocean & Pool View 1 bedroom "Jewel" - ACExperience your vacation in this Beautiful Ocean and Pool View, a 1 bedroom, 2 bath condo "Jewel" in this Oceanfront Resort & Spa. From the moment you walk into the living room and master bedroom you will know you made...
Golf Course Views | AC & Shared Pool |vrKCV
vrKCV - Holua Kai 6, Professionally Managed by Kona Coast VacationsHolua Kai 6: Luxury Home with Stunning Golf Course Views and Modern Comforts in a Gated CommunityWelcome to Holua Kai 6, your home away from home! Nestled within the private, gated community of Holua Kai...
nKaanapali, Ocean Front Condo, Free parking and NO Resort Fee’s, Cabana Access.
EXTRA AMENITY If you are arriving early or departing late, we have a Cabana for your convenience with a pool, spa, full kitchen, refrigerator, rest rooms, TV, WiFi, Bar B Que, books and games, for your use. Come for our winter season and see the Whales from our lanai....
***SPRING SPECIAL*** Charming Home, Just Minutes from Town and the Beach with Ocean View.
Kona Ocean View Vacation RentalWelcome to your Big Island retreat—a spacious two-story vacation home in a peaceful neighborhood just minutes from downtown Kona and some of the island’s best beaches. With two private entrances and separate living areas, this Hawaii...
Poipu Tropical Retreat with A/C & Pool/Gym Access
Discover beautiful Kauai from this spacious 1 bedroom vacation home (built in 2018) in the heart of sunny Poipu. Located in Poipu Beach Estates, the newest upscale neighborhood bordering the Kiahuna Golf Course, that is just minutes from the best beaches on Kauai,...
Fully Renovated 2BR/2BA Near Waikiki Beach+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...
Kuhio Shores 113 - Exquisite Ground Floor Unit Right Next To The Ocean
Located on the sunny South Shore at Poipu Beach, just 10 steps from the water's edge, this 1 bedroom condo offers the best oceanfront vacation rental that Kauai has to offer. At Kuhio Shores #113 nothing can beat the location and views. Perfect paint, perfect...
25% OFF for MAY 2025-Direct Ocean Views From Every Window - 3bd/3bth Honua Kai
THE MAUI LUXURY RESORT LIKE NO OTHERPicture the perfect Hawaii vacation: Of time spent with family and friends, of cares washed away by sand and sea—and the discovery that life can still hold magic, especially in a place called Maui.Now picture the perfect setting:...
NEW - Luxury 4BR, 3.5 BT, Hot Tub, Cold Plunge, Steps from Queens Bath
Discover the perfect balance of comfort, adventure, and relaxation at Honu House Kauai. Just renovated and brand new for guests to enjoy. Steps from the famous Queens Bath or walking/biking to Hideaways Beach, The One Hotel, and Makai Golf Club. Private hot tub and...
Papakea H201 - Vacation West Maui
Escape to Paradise in Maui's Premiere Oceanfront ResortNestled in the heart of Papakea Resort, unit H201 beckons you with breathtaking ocean and garden vistas. This corner unit on the second floor offers more than just a place to stay – it's your portal to the magic...
Country Club Villas#326 Top Fl Corner, Incredible Oceanview,Spacious Lanai,AC
Country Club Villas, Unit#326 is a phenomenal new addition to the Vacation Rental Market that Knutson & Associates Property Management is proud to represent. This top floor corner unit is completely remodeled, with soaring ceilings & lots of extra windows for natural...
NEW! Serene Tropical Oasis in Princeville, with Pool, Hot Tub, Lanai, AC & WiFi!
Welcome to your Princeville Tropical Oasis!My home has 60+ stellar reviews on other platforms and I'm getting started on VRBO! Optimally-located 1-bedroom in the heart of Princeville on Kauai’s stunning North Shore.Located just minutes from Hanalei Bay and Kauai’s...
Ko Olina Kai 1097C: 3BR Hawaii Haven with Golf, Lagoons, and Spa Access
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Step into the world of serene luxury at Ko...
Ocean-view condo with lanai, shared pool, hot tub, fitness center & bbq area
Na Hale O Keauhou H5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched in one of Kona's premier resort developments, Na Hale O Keauhou, this spacious 2-bedroom, 2-1/2 bath,...
Mauna Lani Treasure - Newly Decorated 3 Bed/2.5 Bath Townhome with Beach Club
Kick back and relax in Paradise in this 3 Bed/2.5 Bath Townhome decorated in Hawaiian style. Enjoy this spacious home with a custom kitchen, outdoor lanai with grilling area, and open concept living area. Sip a tropical drink off the lanai enjoying spectacular views of...
Experience the perfect blend of privacy, tranquility, and luxury at Na Hale O Keauhou
**New Property Listing**Welcome to Kai Nani Hale – Luxury Living in ParadiseDiscover Na Hale O Keauhou, a prestigious gated community nestled in the heart of the Keauhou Resort area. This meticulously maintained 13.36-acre complex features 14 pods, each comprising six...
Moloa'a Bay Villa - Impressive Home and Guest Cottage
Moloaa Bay Villa, on the northeast shore of Kauai, is steps away from a secluded white sand beach! Welcome to Moloa'a Bay on the northeast shore of Kaua'i. This is a large, secluded, pristine white sand beach that lends itself to coastal hiking, snorkeling, body...
Kaanapali Alii | 352
From the moment you enter Kaanapali Alii 352 you will notice the clean, modern, and colorful details that combine perfectly to make this a desired Maui vacation residence. The soft-colored (white/gray) flooring and minimalist white walls are complimented by refreshing...
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
"In order to comply with Oahu's 90 day minimum short term rental laws, we may not advertise to rent for a period shorter than 90 days."Come enjoy island life while staying in our newly built, 600 sq. ft. upstairs suite. Beautifully furnished with a modern meets the...
Villa Sea Renity Remodeled Family Friendly Tennis
Experience the relaxing setting of this 1BR 1.5Bath condo in the lavish gated community just a stone's throw away from beaches, shops, restaurants, and attractions of Hawaii's Big Island. Take in the area's scenic beauty and diverse selection of water activities. After...
Luxury Mahana Oceanfront Condo -1bd/2ba - Premium 10th Floor- Fully Upgraded
Welcome to Mahana 1015, a breathtaking oceanfront condo located on one of the top floors of the exclusive Aston Mahana at Ka’anapali Resort. Offering two full bathrooms and spacious accommodations, this one-bedroom suite is the perfect place to indulge in Maui’s...
Beautiful Oceanview Condo with Spectacular Sunsets! - Recently Renovated
Located on five miles of sandy beach on Maui’s southwest shore, the lovely Sugar Beach Resort will capture your heart. Take a leisurely stroll down the sparkling white-sands of Maalaea Bay’s Sugar Beach, one of Maui’s favorite places to swim, snorkel, kite-board,...
Cozy studio, split AC, kitchenette, steps to beach in best South Kihei location!
Aloha and welcome to the Tranquil Turtle Retreat at Maui Banyan Resort! Our recently updated studio is located right in the heart of South Kihei close to world-class beaches, shopping and amazing restaurants. Enjoy Maui at its finest!The Tranquil Turtle first floor...
Spectacular 3 Bedroom Oceanfront Marriott Maui Ocean Club
Welcome to Marriott's luxurious 5-star resort and its spectacular Lahaina and Napili Tower villas! Your sophisticated, bright, spacious oceanfront 3 bedroom/3 bath villa, with breathtaking panoramic Ka'anapali Beach and expansive Pacific Ocean views...as well as every...
Loft Style Completely Remodeled Condo
This stunning condo is located in the oceanfront building of the Kona Bali Kai, although not an oceanfront condo. There isn't an ocean view, but your proximity to the ocean is VERY close!! Just a walk through the under building parking garage, and you're there!The unit...
Kauai Exclusive - Pili Mai 7E - Three Bedroom Suite - AC, Pool & Fitness Center
Pili Mai 7E is a three-bedroom, two-level suite with plantation-style architecture. Newly furnished and decked with bamboo floors, Koa cabinets, a gourmet kitchen and central A/C, this villa is a fresh find. Revel in all the bells and whistles of a new tropical vacation...