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.
KKSR#176 DIRECT OCEANFRONT CORNER AIR CONDITIONED TOWNHOUSE, CLOSE TO POOL
**AC! NEW LUXURY VINYL PLANK FLOORING INSTALLED IN BEDROOMS AND STAIRS WITH FRESH PAINT**This is a gorgeous ocean front townhouse corner unit. Being an end unit with additional side windows allows for additional light in the unit, and because it is located at the end of...
Ilikai Hotel, One-bedroom Unit, Great view of the Hilton Lagoon and Waikiki Beach!
This condo is located on the 18th floor of the Ilikai Hotel.Most sought after view in a SPECTACULAR location with views of the Pacific Ocean overlooking the Duke Kahanamoku Lagoon! Imagine waking up to the beautiful and calming view of the ocean and...
Aston Kaanapali Shores #550: 1 Br Garden View at Ocean Front Resort
This unit is filled with sunlight and creates a welcoming environment for anyone looking to spend time in and out of their unit while on Maui. The condo is simple but thoughtfully furnished and provides you with everything necessary for a successful Maui vacation from...
Sugar Beach Resort Condo w/ A/C, Shared Pool/Hot tub-Surf, Bike, Golf, More
Sugar Beach Resort 511Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Large Penthouse 1 Bdr/2 Bath with Washlets, Wi-Fi, AC, FREE Parking
Marine Surf #PH4 – 364 Seaside Ave.This extra-large (1037 interior sqft plus 275 sqft lanai with table and chairs) centrally located and split air-conditioned one-bedroom, two-bath condo is perfect for a family of 6 or two couples! You'll have a great view of the...
Breezy Corner Studio with AC & Kitchenette. FREE Parking, Wi-Fi, near Beach!
Marine Surf #701 – 364 Seaside Ave.This air-conditioned corner studio features 2 lanais (balconies), great cross-breezes, and is right in the HEART of Waikiki, a short walk from Waikiki Beach, swimming and surfing, shopping, restaurants, and nightlife nearby! You'll...
Gianna’s Place~Sparkling Pool, Jacuzzi & BBQ’snn
This homey studio is in Princeville Kauai on the Makai Golf Course. Golfing, Hiking, Surfing, Snorkeling all close by. Sparkling Pool, Hot Tub and 2 nice BBQ's, cable & WiFi. Affordable, comfortable, complete.Short drive to amazing beaches as well as the wonderful town...
Hilton Waikoloa Pool Pass Included for stays thru June 2025. Halii Kai 22H.
This vacation rental is professionally managed by ResorticaHawaiiPLEASE NOTE: Halii Kai 22H had been listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice. Please reach out with any questions.Halii Kai 22H. Three Bedroom. ...
Ma'alaea Surf #G-1 – Ground Floor Gem with Modern Comfort
A Note from the Owner: Welcome to Ma'alaea Surf #G-1, a rare ground-floor gem offering unmatched convenience and comfort. This beautifully renovated two-bedroom unit creates a modern and inviting ambiance for your tropical retreat. The master bedroom features a...
Koa Resort 5H | Explore Paradise at Koa Resort!
Experience the allure of Kihei at Koa Resort 5H, where luxury meets leisure in the heart of this iconic Hawaiian destination. Situated amidst six miles of pristine beaches and breathtaking views, Kihei offers endless opportunities for adventure, from swimming and...
Spectacular Views! Gorgeous Home In Hilo With Pool
The Hilo Bay View Estate is a gorgeous European-style home located in the exclusive area of upper Wainaku in Hilo. This stunning home has spectacular panoramic views of the ocean and Hilo town. Watch the magnificent sunrises in the morning and star-filled skies at...
Maui Sunset Vacation Rentals B414
One of the best locations in the "B" building on the 4th floor near the pool. View of the ocean and West Maui Mountains. Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Private view deck and renovated...
Cottage-like Duplex in South Kona on the Big Island.<br>Sleeps two adult guests
This Wonderful Spacious house-like One Bedroom apt/flat is on a side-by-side duplex building has peaceful cottage setting on a working farm in South Kona farm belt rural area, Its elevation provides cool temperatures & amazing, lush foliage with ocean and mountain view...
Endless ocean views with cozy accommodations
Noelani 105 is a 1-bedroom,1-bathroom condo featuring amenities such as panoramic ocean views, a washer/dryer, and a ground-floor lanai. The condo can accommodate up to 4 guests with a King-size bed in the bedroom and a queen sleeper sofa in the living space. The...
Hidden Gemstone for One Dreamy Escape!
Congratulations and thanks will go to the decision makers taking the time to note the difference before selecting this hidden gemstone for accomodations while on Oahu. Once your travel companions catch their breath after initial first peek, don't be surprised at the...
Ocean and Diamond Head view suite w/balcony
Legally permitted rental - 134 Kapahulu Ave #408** For your health and safety, we utilize additional Sterilization procedures between reservations.Ocean and Diamond Head view suite at the Waikiki Grand - Kitchenette with electric cook top, microwave and regular size...
Tranquil condo with pools, hot tub, jetted tub, grill & board games - near beach
Poipu Mermaid 912Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'From the sands of Hawaii to the shores of Kauai, you'll be astounded by the beauty of this slice of paradise! You'll...
Free Parking! 6 Minute Walk to Waikiki Beach!
As of January 1, 2026, Hawaii will increase its Transient Accommodations Tax (TAT) rate by 0.75%. For reservations booked before January 1, 2026, an additional payment request will be sent for the 0.75% tax increase.This is a legal conforming vacation rental. Please see...
Newly Remodeled Whaler #1062 Ocean View Studio Suite
The Whaler on Kaanapali Beach #1062 is our brand new remodeled Studio condominium with stunning ocean views. Brand new furniture, carpet and smart TV. This beautiful vacation home is a 530 square foot studio located on the popular courtyard side of Tower II. Sitting on...
🏖️Great Location | Modern Island condo | AC Included | vrKCV
vrKCV - Casa de Emdeko 221, Professionally Managed by Kona Coast VacationsWelcome to Casa de Emdeko #B221, your serene island escape just 150 yards from the ocean. This spacious 780-square-foot second-floor condo is perfect for 2–4 guests seeking comfort, relaxation,...
Wai'ula'ula 308 - Upcountry Residence
This chic and sophisticated, ‘upcountry’ oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, an epicurean kitchen outfitted with Wolf appliances, including a gas range, double ovens and wine refrigerator, three...
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S3)*One...
Maui Parkshore 409: Have fun in this two bedroom, two bath Ocean View condo.
**Please note that the pool will be closed from Wednesday, September 4 through Thursday, September 12 due to pool deck maintenance**Have fun in this two-bedroom, two-bath Ocean View condo. Conveniently located in South Kihei, there are shops and restaurants just a block...
Oceanfront condo - ocean-view lanai - steps to beachside pool & hot tub
Islander on the Beach 250Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover the perfect ocean getaway at Islander on the Beach, a 6.5-acre oceanfront resort with stunning...
Perfect Location for your Maui Stay! Pacific Shores B118!
The best location on South Maui! Pacific Shores is all about convenience and location. Who needs a car when you are across the street from favorite Charley Young Beach, 1 block from popular surf spot ''The Cove'' and half a mile from many restaurants, shops, and...
Kona Mansions | Ocean Views & Amenities!
Summary:A complete Hawaiian experience can be found at Kona Mansions. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:This unit is a 1 bedroom, 1 bathroom ocean view condominium capable of accommodating up to 3 guests. Vacationers on...
Zen home with fast WiFi, washer/dryer, koi pond & large lanai
Seabreeze Hawaii Kai -A - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’re sure to find your zen at this slice of paradise. From a gorgeous lanai to a lush...
Hale Kamaole 202 Second floor condo, easy access to best beach on Maui!
Welcome to your beach getaway! This 2 story, 2 bedroom plus loft, beautiful beach front condo comes with all the comforts of home including WI-FI, three flat screen TV’s, everything you will need in the kitchen to cook delicious meals and more. The kitchen is...
Menehune Shores #423 – Stunning Ocean Views and Relaxation Awaits
Menehune Shores is an oceanfront property located in North Kihei, offering breathtaking views of the Pacific Ocean and easy access to the sandy beach. This comfortable and spacious condo is perfect for families or groups, with its proximity to a protected beach area and...
Second Floor Oceanview with Gorgeous Sunsets
Hawaii Tax ID: TA-055-659-1104-01TMK: 390080030048This Hale Kai O'Kihei 219 condo is located directly on the ocean edge and boasts a 180 degree panoramic view of the mighty Pacific. Newly remodeled in 2015 kitchen and bathroom in this beautiful...
Kauhale Makai Unit 122: Ground floor 1 Bedroom condo at Ocean Front Resort
Spacious and comfortable describe this ground floor condo with a beautiful garden view and partial ocean/mountain views. This unit, which sleeps 4, boasts a fully equipped kitchen, separate dining, central AC and a large bedroom with a comfortable queen bed. Perfect for...
Ocean and Golf Course Views 2 bed 2 bath - Grand Champions 112
Book with us and come to Maui to explore everything we have to offer!This spacious Wailea Grand Champions Villas 2 bedroom 2 bath second floor unit is tastefully decorated and has everything you need for a relaxing vacation. Great ocean, tennis courts and tropical...
Family-friendly condo w/shared hot tub, outdoor pool, mountain and garden views
Pali Ke Kua #4Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Transport yourself to a tropical and magical paradise when you book this condo plus loft! Ideal for four people, this...
Aloha Condos, Nohonani Condos and Resort, Condo 205, Beachfront, AC
WELCOME TO NOHONANI 205 and IMAGINE, you are on the lanai, you relax, sit back, enjoy the sounds of the rolling waves, and refresh yourself with the warm ocean breezes. 180 degree ocean views capturing breaching whales, pods of dolphins, turtles in the waves or...
New baths, king bed, open & tranquil pool hot tub
Summary:Tropical Elegance in Waikoloa Beach Resort. Immerse yourself in the essence of Hawaiian paradise. This two-bedroom, two-bathroom haven offers a spacious retreat within the original condominium community of Waikoloa Beach Resort. With a perfect blend of modern...
Open-Plan Lush Garden Home Near Kailua & Lanikai Beaches
Min 30 days requiredLush tropical gardens make this private home into a quiet, comfortable retreat. Large enough for six adults, plus a couple of keiki (children), this home was designed by the late Vladimir Ossipoff, award-winning Hawaii architect. Mr. Ossipoff's...
Ilikai Apt 1822 - 2BR/2BA Modern Unit with Ocean & Harbor Views No resort fees!
Oceanfront 2BR/2BA at Ilikai | Sleeps 6 | Prime Waikiki LocationProperty Overview:Welcome to your spacious ocean-view retreat in the iconic Ilikai Hotel, just steps from the Hilton Lagoon and Waikiki Beach. This fully equipped 2-bedroom, 2-bathroom condo offers...
Ocean View Lanai W/Full-Kitchen – Waikīkī Shore #506
Castle Waikīkī Shore #506: Island living meets modern convenience in this recently upgraded one-bedroom and one-bathroom ocean-view suite.The full-size kitchen with modern furnishings and stainless-steel appliances makes this unit ideal for small families or a group...
Ocean-view studio with lanai, pool & hot tub - steps to Banyans Beach & trolley
Kona Bali Kai #264Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beautiful Banyans Beach is mere steps across the street from this thoughtfully updated studio condo in Kailua-Kona....
Kahakai Place - AC, Gated, 1 Block from the Ocean
Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Oceanfront condo with loft, WiFi, shared pool & hot tub, balcony
Pali Ke Kua 213Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pali Ke Kua, situated in the planned community of Princeville on Kauai's magical North Shore, is often described as the...
#324-Oceanview Maui Condo - Sunsets and Whale Watching!
Welcome to Menehune Shores 324, your oceanfront oasis in South Maui featuring breathtaking sunset views and prime whale watching during winter months. This beautifully appointed 2-bedroom, 2-bathroom condo offers a spacious open floor plan with a fully equipped gourmet...
Stunning Ocean View Hawaiian Downtown Getaway
Welcome to our tranquil oasis in the heart of downtown Kailua Kona! Perched on a hill, our stylish condo boasts breathtaking ocean views and easy access to all that the vibrant town has to offer.Step onto the private lanai and immerse yourself in the beauty of the...
2 Free Parking!! Spacious 1 Bedroom Penthouse in Palms at Waikiki.
You cannot find a penthouse, 2 parking, 1 bedroom vacation rental in this price!Room rate will be less than a half of the small studio class hotel room. More space, less price and 2 parking. You may also enjoy the diamond head and ocean view from the room!!From the...
Hale Kai 115: Oceanfront Paradise with Stunning Views and Poolside Access!
Hale Kai 115 offers magnificent ocean views and just steps to the pool! This ground floor 1 bedroom/1 bath is a perfect getaway for couples or a small family!As you enter, you are immediately drawn to views of Molokai, Lanai', and the beautiful Maui waters. Catch a...
Kona by the Sea Oceanfront Condo KBTS407
TMK: 750200160027TA-053-340-5696-01Relaxing Ocean Front Condo! Stunning direct ocean views. This one bedroom - two bath condominium has been fully updated with quality materials. Custom solid cherry wood cabinets and interior doors. Gleaming granite counter-tops in...
One Bedroom Deluxe Garden View Luana Kai Resort B108
B108 with AC is a Ground floor, 2 bedroom, 2 bathroom garden view condo. It offers easy access to the putting green, pool, bbq's, tennis, pickleball and ocean. B108 was totally remodeled and features a wonderful kitchen complete with everything you need to enjoy your...
Villa on fifth Ave in Paradise
Experience easy living while staying at “Villa on 5th Ave in Paradise,” a newly built 3+ bedroom, 2.5 bathroom tropical retreat just 20 minutes from Hilo, Liliuokalani Park and Garden, Carlsmith Beach Park and Wailoa River State Park. Sleeping up to 8 guests, this...
Modern, New King Bed, Luxury, Spacious Waikiki Condo with Great View 100% Legal!
Relax in paradise in your luxury suite on the 29th floor of the Hawaiian Monarch Hotel in fabulous Waikiki Beach! This apartment is designed for the discriminating traveler who wants to stay in a clean, spacious, and modern studio with a full kitchen and new King size...
🏖️Ocean View | Close to Pool & BBQ Area | vrKCV
vrKCV - Sea Village 2102, Professionally Managed by Kona Coast VacationsWelcome to Your Tropical Paradise at Sea Village in Kailua-Kona, Hawaii!Escape to this delightful one-bedroom, one-bath condo, perfectly situated just a short distance from downtown Kailua-Kona on...