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.
Seaside Serenity in Hawaii
About this spaceDiscover our island oasis in Koloa!, Hawaii Nestled in a tranquil and tropical paradise, our upgraded unit at Kiahuna Plantation Resort (Unit 434) offers modern comforts like a new AC, plush mattress, and cozy couch. A short stroll through lush grounds...
Ocean View Villa in Kahana, Maui
Experience the ultimate comfort and relaxation in our beautifully adorned Maui haven, Kahana Villa F404. This exquisite condo boasts an array of personalized touches that will leave you feeling right at home. Indulge in the breathtaking vistas of the Pailolo channel and...
Contemporary cool with endless Ocean views
Nestled within the breathtaking Kapalua Bay this exquisite 1-bedroom, 1.5-bathroom villa that can accommodate up to 4 guests, effortlessly combines modern comfort, breathtaking ocean views, and practical amenities for a truly unforgettable vacation experience. Kapalua...
Kona Rose's Hideaway in Kona Plaza #318 at the center of Kailua-Kona Town
Welcome to Kona Rose's Hideaway in Kona Plaza #318, your ideal getaway nestled in the vibrant heart of Kailua-Kona! This charming 1-bedroom/1-bathroom suite is perfectly equipped for your comfort and enjoyment, featuring a plush King bed and a cozy Queen bed, along with...
Maui Sunset Oasis- Top Unit w/AC
A stunning oceanfront sunset condo in Kihei! This updated top unit 2-bdr, 2-bath with AC offers stunning sunsets from manicured grounds. Step onto the private lanai to unwind and enjoy panoramic ocean views! Take a dip in the pool or stroll to two beautiful beaches....
NEW! Luxury Plantation Home on Kiahuna Golf Course
About this spaceThis gorgeous Hawaiian Plantation Style home designed by a local architect, resides on the 8th fairway of Kiahuna Golf Course with views of Haupu Mountain.Spectacular Gourmet Kitchen , chefs will enjoy !Poipu features many beaches to indulge in surfing ,...
Tropical Oceanfront Piece of Paradise, Every Room with Ocean Views and A/C!
QUIET and PEACEFUL on the edge of a bluff overlooking the Pacific. Soak up the unspoiled ocean air and magnificent breathtaking blue water horizon, ultimate beauty and peace. And from each room observe the most magical colors of sunset over ocean every evening.Wake up...
South Kauai Tranquil Retreat w/ AC in Poipu
Waikomo Streams is a peaceful, tranquil, and beautiful property with immaculate gardens. Immerse yourself in a paradise garden view on the Garden Island! We have an updated, air conditioned unit that is quiet and comfortable. The property boasts tropical gardens, a...
Escape To Paradise at Waikoloa Fairways' 2 Bed 2.5 Bath Condo and Stunning View
Experience the ultimate in vacation comfort with our exclusive benefits. Enjoy complimentary late check-out (subject to availability) to maximize your stay. Book a 7-night stay and receive your 8th night completely free – perfect for an extended escape. Plus, as a thank...
Surfer's Paradise: Waialua Condo Steps to Beach!
Experience the beauty of Hawaii at this cozy 1-bedroom, 1-bath vacation rental in Waialua. Relax with a book on the patio or walk to ʻĀweoweo Beach Park for world-class big wave surfing. This cozy condo also includes a flat-screen TV, a community coin laundry area, and...
Tropical haven, close to beaches and shopping
Paki Maui 414 is a 1-bedroom, 1-bathroom condo located on the fourth floor with wonderful garden views from your lanai and floor-to-ceiling sliding glass doors, bringing natural light into the condo. The condo does have a split air conditioning in the bedroom and living...
Honu Hale on Turtle bay golf course & near beach
2 bed 2 bath condo with a loft. Sleeps 4 people. Explore Oahu and enjoy North Shore's beautiful ocean. Just a 8 minute walk to the relaxing beaches of Turtle Bay Resort. A short 5-15 min drive to many legendary beaches with soft sand, turquoise water, & amazing waves!...
Mauna Lani Fairways 603: Luxe 2BR Home w/ Modern Comforts, Jacuzzi & Lanai Views
Escape to comfort at Mauna Lani Fairways 603, an elegant retreat in Hawaii’s lush Mauna Lani Resort, where recent updates and thoughtful details create the ultimate island sanctuary. With two bedrooms, two and a half bathrooms, and space for up to six guests, this...
Serene Lanikai House Near the Beach w/Full Kitchen and Great Outdoor Space
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out, professional...
Contemporary furnishings in your cozy 1bd escape
Kauhale Makai 108, nestled along Maui's serene coastline, this inviting 1-bedroom, 1-bathroom ground-level unit offering central A/C, ceiling fans, and tropical views . Unit 108 can accommodation for up to 4 guests. The master bedroom boasts a queen-size bed adorned...
2 Mins to Private Beach, Dolphin Whale Watching, Hi6
🌺 Dolphin Bay Estate - 2-min walk to a private beach + epic ocean vibes 🌊🐬Tucked in scenic Captain Cook on Hawaiʻi Island, this peaceful retreat is made for unplugging and getting things done. Wake up to ocean views, spend your days snorkeling/whale watching nearby,...
Renovated Waikiki Studio, Full Kitchen, Free Parking, 4 Blocks to Beach!
Fairway Villa #1109 – 2345 Ala Wai Blvd.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You'll enjoy this newly remodeled (August 2023) 11th-floor studio in the quieter east end of Waikiki. With a full kitchen, free Wi-Fi, and free parking, this...
Hapuna Beach Paradise 2 Bed Penthouse Oceanfront View Resort
Important Notice for 2026 BookingsIf you're booking a stay with us for dates beginning on or after January 1, 2026, please be aware that a Hawaii tourism tax increase of 0.75% will be implemented to support climate relief efforts on the Hawaiian islands.Although this...
Remodeled 1BR/2BA at Kamaole Sands: Steps to Beach
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 + Privacy ✨ Near Putting Green ⛳ Beach Club Access 🏖️
Summary:Ka Milo in the Mauna Lani Resort • 5★ RatedKa Milo 228 is a luxurious 2-story townhome located in the highly desirable community of Ka Milo in the Mauna Lani Resort. With two master suites and two additional bedrooms, this townhome is perfect for a family or a...
Hapuna Beach Residences B22
This spectacular, oceanfront, newly-constructed studio offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a luxe chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine storage, plus a dining table...
Beach Front Condo w/ Beautiful Sunrises on Private Sandy Beach + Turtles + Perfect Snorkel Spot
Escape the hustle & bustle of Waikiki crowds & enjoy beautiful sunrises, private beach, calm waters & experience amazing turtles sunbathing on the beach. Relax & experience a memorable vacation in our modern beach front condo w/ an Elegant Coastal Décor and serene cozy...
🏖️New Vacation Rental! | Professionally Decorated | Concierge Included
vrKCV - Mauna Lani Fairways 801, Professionally Managed by Kona Coast Vacations🌺 Private Hawaiian Retreat — Beaches Golf & Aloha Living 🌺801 Fairways at Mauna Lani - Kohala Coast - Big IslandWake up to sweeping golf-course views, relax under soaring ceilings, and unwind...
Walk to Downtown Hilo: Condo w/ Pool Access!
Near Restaurants & Shops | Free WiFi | < 1 Mi to BeachesExperience the ultimate island getaway at this Hilo vacation rental! Featuring a prime location just down the road from stunning beaches, downtown markets, hiking spots, and more, this 2-bedroom, 1-bath condo is...
Brand New Luxury 5BDRM Home at Mauna Lani Resort
Brand new contemporary single-story luxury estate located in the exclusive One Ocean community at the Mauna Lani Resort. This expansive 5 bedroom, 5 bath home comfortably sleeps 10 guests and is ideal for a family vacation or as housing for a business group needing...
Puolani Iki-Sweet lil cottage near National Park
Snuggle into the beautiful Ohia forest. Make yourself at home in your own little rainforest retreat, and wake up to views of the beautiful hapuu ferns right outside your window. This little cutie has everything you need for an east Hawaii adventure!Our little Volcano...
Tropical Paradise Retreat in Princeville! Full Kitchen, Swimming Pool!
Set on the picturesque North Shore of Kauai, this resort offers stunning ocean and mountain views with easy access to Hanalei Bay’s beaches and hiking trails. Ideal for nature lovers, it provides a serene getaway close to local shops and dining options.This listing is...
Fully Loaded 1 Bedroom 2 Bathroom Condo in Kihei, Maui!
This stylish place to stay is perfect for your trip. Fully loaded with everything you need in the kitchen and out on the beach! You'll have a wonderful experience staying at this condo. Kick back and relax with the A/C or hangout outside on the lanai with a very...
Renovated 1BD/1BA Condo with A/C 3 min Walk to Beach
South Maui is open! Come unwind in this completely remodeled 1BD/1BA condo across from the Charley Young/ Kamaole I beaches. This soothing space will greet you with a gorgeous garden & partial ocean views. Bedroom has a queen size bed, TV, its own AC & a large closet....
Pinnacle at Poipu - 6 Bedroom Luxury Estate - Amazing Views & Salt Water Pool!
Introducing the Pinnacle of Poipu: A Magical and Exquisite Getaway on the Garden Isle. Elevate your vacation experience at this exclusive luxury vacation rental nestled in the heart of Poipu, Kaua'i. Perched high atop its picturesque surroundings. A true masterpiece...
North Shore Oceanfront Retreat Sunset Beach
Escape to the stunning shores of Haleiwa and experience the ultimate beachfront getaway at our charming vacation rental. Nestled along the pristine sands and turquoise waters, this slice of paradise offers an idyllic setting for relaxation, adventure, and unforgettable...
Elua 1603: Premier Views, Exquisite Updates!
Wailea Elua Village #1603 boasts some of the best Ocean Views and is located on one of the most prestigious properties on Maui. This condo has been lovingly maintained and updated to ensure it remains a luxury-level choice for those traveling to Maui.Featuring the...
2 - bedroom Waikoloa Townhouse 106, close to beaches and restaurants
New rental listing starting September 2023Welcome to our relaxing, freshly updated Villa at the Waikoloa Colony Villas. Unit 106.New furniture, and beds throughout the home! Waikoloa Colony Villas is a private gated community of luxury townhomes on the South Kohala...
Princeville Queens Bath House - 100 Steps to Trailhead
Our house was designed to be the ultimate family vacation house. It has a 29' pool and exotic tropical hot tub with waterfall ! You'll love the fully opening sliding glass lanai doors, bringing the island style open feeling from the great room to the outdoor lanai -...
Huge Patio 1BR WasherDryer Free Parking 5 min to beach
*** Newly renovated in August 2023Relax and unwind in this 1BR condo while being 5 min walking distance (one block) from the famous Waikiki beach. Resided in Waikiki Banyan condominium with 24-hour security, the condo offers the following characteristics that are...
Hale Lewa ~ Newer Home ~ Ocean Views ~ 30 Day Rent
Summary:Nicely Appointed Modern Home - Ocean ViewThe Space:Hale Lewa is a 30 day minimum rental.Serving as a 3 bedroom, 3 bathroom sanctuary atop a hill with beautiful ocean views, Hale Lewa is a great base to enjoy the Kohala Coast of the Big Island. The spacious open...
Luxury Mauna Lani Home - Views!
Welcome to Hale Kalea, the House of Joy and Happiness! After many years as a successful vacation rental, Hale Kalea has new owners and we can’t wait to welcome you back!Located in the Mauna Lani Resort’s exclusive gated community of Champion Ridge and perched above the...
Includes Beach Gear! Kanaloa 303
Kanaloa #303 at Keauhou on the Big IslandPLEASE NOTE: Although, Kanaloa 303 is listed for sale, guests will not be asked to accommodate showing or inspections. If it goes into contract, bookings are guaranteed for 60 days. Please reach out with any questions.Please...
Makahuena 2102 by Destination Kauai with A/C
E Komo Mai, Welcome to The Makahuena 2102!“The Makahuena” is located on the southernmost point of Kauai. This unique oceanside resort is situated on the edge of a bluff providing spectacular coastal views. This spacious 3BR/2BA ocean view condo has over 1,300 sqft of...
Keauhou Punahele | Condo in Kailua-Kona
Keauhou PunaheleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This dreamy island condo is waiting to welcome you to a true slice of paradise. Wake each morning to the sounds of...
KBM Resorts | FREE CAR | The Whaler | Ocean view | 1-Bedroom, Recently Updated and Gorgeous views! WH1-1211
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
Do you like an unobstructed panoramic view of the ocean and sunsets? Comfortable beds? Air conditioning in 4 zones? Quiet neighborhood? Excellent location in the heart of Kona? Free WiFi? This house has it all. Wake up in the morning and have a coffee on the very large...
KBM Resorts | FREE CAR | Napili Bay | Oceanfront | Stunning Studio Villa, Turtle views! NAB-107
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
🏖️Top Floor with Loft | Ocean and Golf Course Views | AC & Concierge Included
vrKCV - Country Club Villas 305, Professionally Managed by Kona Coast VacationsCome enjoy a slice of paradise in this colorful Kona getaway with spectacular ocean and golf course views from the lanai, living room, kitchen, and primary bedroom! Wake up to the sounds of...
Unmatched location Four Seasons Hualalai 5BR/5BA Ocean Estate 6500sqft 3/4 acre
Escape to your own private paradise at this stunning newly renovated expansive 5 bedroom, 5 bathroom 6500 square foot ocean adjacent estate, a beautiful custom home on 3/4 of an acre, nestled within the exclusive Four Seasons Resort Hualalai. Experience the height of...
Experience Tranquil Luxury at Pele's Last Resort, Holua Kai
The Hawaiian Islands are a true paradise on earth, with their stunning natural beauty and unique cultural heritage. Experience the tranquility of Hawaii's Big Island with a stay at "Pele's Last Resort". This three bedroom, two and a half bathroom vacation home is...
Spacious 1bd, ground floor, lanai, walk to beach
Welcome to Maui Kamaole M109, a tropical paradise nestled in the heart of Maui's beautiful South Kihei region. This delightful property offers the perfect combination of comfort, convenience, and island charm. Step into this enchanting ground floor 1-bedroom, 2-bathroom...
Oceanfront Bliss- Boutique Hideaway- Pohailani 212-Special Low Rates-Book Now
Escape to Paradise at Surf Hale – Luxury Maui Vacation Rental in Kahana. Partake in this stunning luxury oceanfront rental in Maui, perched just 10 feet from the water’s edge on the second floor. Freshly remodeled, this romantic getaway in Kahana offers breathtaking...
Waikiki Ocean View with AC, Full Kitchen, Washer/Dryer, FREE Parking & Wi-Fi!
Waikiki Skytower #2604 – 2410 Cleghorn St.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy magnificent Pacific Ocean views from this contemporary, updated high-floor, one-bedroom condo (585sf plus 90sf lanai with table & chairs)! With only 4...
BEACHFRONT/GROUND Floor B-103: Renovated, LARGER unit, & steps from the sand.
Pocket sliding doors from the large 2 living room areas to the large lanai to the white sandy beach! Open concept with amazing ocean views everywhere in the large room, which includes the dining room area plus well equipped kitchen with subzero fridge and marble counter...