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.
Princeville Kauai 2 bedroom 2 Bath Sleeps 5
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This premier complex, perched on a verdant bluff, provides a paved path to Hideaways Beach, where you can snorkel, swim and soak up the sun. On-site amenities include a restaurant,...
Hilton's Point at Poipu - Luxury 2 Bedroom Villa
Weeks are offered on a Friday, Saturday, and Sunday check-in & out in SEVEN NIGHT INCREMENTS.The REQUEST TO BOOK feature is a request for a reservation, not a confirmed stay. Please do not reserve your airfare until you have communicated with us and we have accepted the...
New Listing 1BD Oceanfront Condo in Lahaina
Lahaina Shores 601 – Oceanfront Elegance with Panoramic ViewsDiscover the magic of Maui from Lahaina Shores, a charming boutique resort set directly on the ocean in the heart of Lahaina. Unit 601 is a rare, highly coveted 1-bedroom, 1-bathroom corner retreat on the 6th...
Oceanfront Paradise Awaits at Kahana Reef 215
Your Oceanfront Escape Begins at Kahana Reef 215Step into paradise the moment you arrive. Kahana Reef 215 sits directly on the water’s edge—so close you’ll fall asleep to the lull of the waves and wake to stunning, unobstructed ocean views. Enjoy your morning coffee or...
Dlx 1-Br Waikiki Condo Rental...Lovely views. Waikiki Beach!nNear Diamond head.
Enjoy your own 1-BR Oahu condo rental getaway - just a short stroll to Famous Waikiki Beach & and ideally located near world-famous Diamond Head. We're On the 'quieter side' of Waikiki, near Kapiolani Park. Your 1-bedoom Waikiki Beach Condo vacation getaway is appointed...
Maui Resort Rentals: Honua Kai Konea 504 – Luxurious 2BR w/ Beautiful Partial Ocean & Mountain Views!
Konea 504 is a luxurious two-bedroom suite, offering guests the best of both worlds, beautiful partial ocean and mountain views right from the comfort of your spacious private lanai. Located in the very first two-bedroom stack from the oceanfront column, your group will...
Kona Bliss Hawaiian Oasis w/ Pool, 2 King Suites & Sunset Views!
Discover true Aloha at this stunning 3-bedroom oasis, where island charm meets luxury. Behind a gated front entry, this beautifully designed home features soaring vaulted ceilings, dramatic lava rock wall & 2 king suites and a chefs kitchen, offering a serene and...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, Premier 5th Floor Interior Courtyard Offering w/ Stunning Ocean Views!
This tandem 3BR/3BA pairing is comprised of two fantastic 5th-floor oceanview suites located directly next door to each other. Both suites overlook the lush resort grounds and pools of the Hokulani Tower interior courtyard and provide stunning full ocean views.Gather,...
Marriott Maui ocean club full kitchen, 2/22/26-3/1 on beautiful Kaanapali Beach
February 22/26 thru 3/1/26 only Escape to this fabulous condo in picturesque Lahaina. This wonderful property features 2 gorgeous bedrooms with king beds, 2 bathrooms with luxurious amenities like a full kitchen, jetted bathtub, and a cozy living room with a sofa bed...
Waikiki Shore Park View 1 Bedroom
Park views and beachfront living come together in this cozy one-bedroom condo, located in the only condo building on Waikiki Beach. Featuring a private bedroom, full bath, and all the essentials, it's the perfect island escape for couples or small families.Park View 1...
Fairways North 22 Four Bedroom
Located within the desirable North Fairways at the prestigious Mauna Kea Beach, this charming 4-bedroom residence will meet all of your Hawaii resort vacation wants. This beautiful vacation rental not only offers breathtaking panoramic ocean views it also provides views...
Honua Kai Hokulani | 3 Free Rental Cars | KBM Resorts | Large Floorplan | 3 Units, 6 Bedrooms | ML-1227
** 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...
*Hono Kai A14* New Listing! Maui condo steps to the sand!
Beautiful ground floor and newly remodeled! Hono Kai A14 is a garden-view unit, immersed in rich tropical foliage with a spacious private lanai only steps from the complex beach access! Decorated with a modern beachy decor, this unit features a master suite with a comfy...
1 Bedroom Partial Ocean View Condo - Kaanapali Shores 830
Settle into your Hawaiian vacation in this Oceanfront and ground-floor condo with beach and pool access in Kaanapali. Wake up to the ocean breeze and just steps away from one of the most popular beaches in Maui. Recent upgrades include: The kitchen has all-new stainless...
Allure Very Nice 2-bedroom condo 30 Day Rental Minimum
This beautiful 2 bedroom condominium at Allure Waikiki #2609, offers state of the art kitchen appliances, great for people that love to cook. It also has a washer and dryer in the unit. The Allure is located in a prominent Waikiki location, walking distance to lots of...
410 - Oceanfront 1 Bed/1.5 bath Unit fully Remodeled 8/2021 Awesome Ocean View!
FREE HI SPEED WIRELESS INTERNET CONNECTIONFREE LONG DISTANCE CALLING TO USA AND CANADAOcean front condo has been upgraded100 feet from one of the finest beaches in MauiWonderful snorkeling and water sports at your doorstepWatch the whales in season from your private...
"Windjammer" Studio w/FREE parking & Full Kitchen
Our Premium WINDJAMMER STUDIO is spacious, recently renovated, fully furnished and centrally located just steps away from famous Waikiki Beach where you can enjoy the sand and surf. We include FREE PARKING, full kitchen, free Wi-Fi and a private lanai. We provide 100%...
Ocean View Studio at Marriott’s Maui Ocean Club – Beachfront Paradise
Discover island comfort and breathtaking views in this Studio Ocean View Villa at Marriott’s Maui Ocean Club – Molokai, Maui & Lanai Towers, located along Kaʻanapali Beach. This well-appointed studio accommodates up to four guests and is ideal for couples or small...
Lodge at Kukuiula Cottage 10
Cottage 10 at The Lodge at Kukui'ula is a private sanctuary nestled on Kauai’s sun-drenched south shore. This charming three-bedroom cottage blends classic Hawaiian style with modern luxury, creating a warm and inviting retreat perfect for couples, families, or small...
Airy Coastal Dream Vistas
Summary:Completely remodeled 1 br, 1 bath modern condo with upscale Hawaiian style. Located directly across from the beach in warm & sunny Kihei. Nestled in the lovely and desirable Kihei BayResort, you will be embraced in the tranquil grounds and ocean views. We...
RELAX w/ Direct Beach Access High Flr. Sans Souci 2BD/2BA🌴Stunning Ocean Views
Nestled along the southeastern coast of Oahu, Hawaii, welcome to Sans Souci condominium 901/902, on the only beach in the heart of Diamond Head along the Gold Coast adjacent to Waikiki. The first thing you will notice is the incredible ocean view from this luxurious...
Tropical Comfort & Poolside Peace—2 Room Island Haven Awaits
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
4BR Kona Home with Ocean Views and AC!
Walua Hale – Oceanview Escape in Kailua-KonaWake to dazzling Pacific views and end your days dining al fresco on the lanai at this stylish 4-bedroom retreat. With space for up to 10 guests, Walua Hale blends coastal charm with comfort—think breezy open spaces, a hammock...
Ka Eo Kai Studio Resort w/ HOT TUB & POOL
Embodying the essence of the "Garden Island," this resort provides a perfect blend of tranquil surroundings and abundant nearby activities. Nestled within lush tropical gardens, it offers convenient access to a myriad of recreational opportunities such as family...
A11y Room with 2 Double Beds, Lanai and City Views
Designed with accessibility in mind, this 242 sq. ft. room features two double beds and a private lanai with city views. With accessible features, air conditioning, free Wi-Fi, and modern amenities, this room ensures a comfortable and convenient stay for all guests.Key...
Luxe Ke Iki Beach Villa by Gather: North Shore Getaway w/AC Near Waimea Bay
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.On Oahu’s North Shore, Ke Iki Beach Villa is a...
Kai Lani 3D Oceanfront ground floor with direct access to the beach
Don't miss this newly listed vacation home. Please send us an inquiry to accommodate your travel dates and requests, or book instantly—one of the more desirable ground-floor units with direct access to the grassy area and the beach. This oceanfront two-bedroom, two-bath...
Alii Villas#318 Beautiful Top Floor Condo with Garden & Ocean Views
Top-Floor Ocean Escape – Remodeled Beauty at Alii Villas #318Welcome to your slice of paradise on the top floor of the highly sought-after Alii Villas in stunning Kailua-Kona, Hawaii! Unit 318 is a fully remodeled, beautifully furnished condo that blends island charm...
Marvelous 3-bedroom house in welcoming Kailua-Kona neighborhood
This memorable house is the perfect home base for your trip to Kailua-Kona. With three comfortable bedrooms, including two queen beds and one twin bed, guests can easily relax and unwind. The two bathrooms provide convenience for families or groups traveling together....
STUNNING 1st Floor 🌴 Beachfront 2BD Sans Souci w/Parking 🐬
You'll find bicycles, golfing, and more on site at this beach condo. Waikiki Beach and Kaimana Beach are just a short walk away, so leave your car at the property, which offers covered onsite parking. After you return to this 1473-sq-ft condo, unwind on the deck or...
Kaanapali Shores | Steps To Ocean | KBM Resorts | Steps to Ocean | 3 Units, 6 Bedrooms | ML-2597
** 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...
Beach Inspired Family Suite w/ Kitchen, Washer/Dryer, Lanai–Waikīkī Shore 510
Welcome to your home-away in this fifth-floor, one-bedroom one-bathroom, ocean view unit. Upon entry, you will be greeted with a white back-drop that has been enhanced with many shades of blue throughout the space. Welcome to the 'beach house!'Guests can embrace the...
Spectacular Lanikai Ocean Front w/Pool - newly remodeled, sleeps up to 18!
Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-air conditioning throughout the home, updated landscaping, new...
Urban Chic Meets Island Serenity in Waikiki
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch building.Enjoy breathtaking Mountain & Canal views. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right...
MARRIOTT'S WAIOHAI BEACH CLUB WITH THE BEAUTY OF KAUAI AT OUR POIPU RESORT
MARRIOTT'S WAIOHAI BEACH CLUB WITH THE BEAUTY OF KAUAI AT OUR POIPU RESORT a premium vacation resort. Located on Poipu Beach, we offer a spacious villa accommodations, equipped with full kitchens, separate living/dining area, washer/dryer, furnished lanais with ocean...
OCEAN FRONT 9th Floor Corner unit nWatch the Whales jumping from the Balcony
In the heart of Maui's famous Kaanapali Beach, steps away from Whaler's Village, with beautiful shopping and restaurants. Beautifully remolded and decorated one bedroom with 2 FULL baths, sleeper sofa and roll-away bed. Wrap around balconies and magnificent views....
Beach Front Condo-Everything you can dream of for a Hawaiian getaway is here!
Enjoy a pleasant stay at this 1-bedroom condo in the quiet country of Hauula. Perfect for relaxing after a day of exploring Oahu. This quaint property offers a cozy living room with a sofa bed. In your temporary home you can take advantage of all the amenities your used...
Westin Kaanapali North Oceanview - Christmas & New Years Weeks - 1 bedroom
We own a 2-bedroom unit that can be rented as a studio, 1-bedroom, or 2-bedroom. This is the 1-bedroom listing.This 1-bedroom unit is in the middle property of the three Westin Kaanapali Ocean Resort properties on one of the highest rated beaches in the world, with...
Enjoy Pauoa Beach Club’s spa, gym, pool, and oceanfront privacy.
Welcome to Honu Pani – a rare oceanfront estate nestled in the exclusive Pauoa Beach enclave at Mauna Lani Resort. One of only seven oceanfront homes in this prestigious gated community, Honu Pani offers unmatched privacy, sweeping ocean views, and a truly unforgettable...
⛩Best location in Waikiki Open design penthouse Studio-Waikiki Grand Hotel® 1005
Elevate your stay in our charming flat, perched on the 10th floor of a unique boutique condotel. 🏛1005 at the Waikiki Grand Hotel® is perfect for couples or small families, our spacious retreat offers breathtaking views of the ocean and lush surroundings that will leave...
Palms at Wailea Villa 1805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- 473 square foot lanai- Master Bedroom with 1 king size bed and guest bedroom with a Queen size bed- Queen sofa bed in sunken living...
Kapalua Golf Villas Fairway View 2 Bedroom
Golf Villas Fairway View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed or 1 queen bed and bathroom- Guest bedroom...
Oceanfront home with wrap around lanai, private sauna, beach access & WIFI
Big Surf Villa (30+ night rental)Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your oceanfront paradise in Waianae, HI! This stunning house boasts a vaulted ceiling and...
Hanalei Oasis Steps from the Beach
Our home in Hanalei Bay (with a beautiful, recent interior makeover) is nestled in one of the most desirable locations on the North Shore, on a quiet cul-de-sac, 1 house away from the beach and some of the best surf in the world. Take an easy walk or bike into town or...
FREE Parking! Penthouse Unit at The Palms Waikiki
Amazing 12th floor Penthouse Unit. This popular unit at Aqua Palms Hotel comes with high ceiling, a spacious lanai with ocean view and larger interior living space than most condotel studio units in Waikiki. 2 queen beds can accommodate 4 guests. This is one of the most...
Diamond Head View Condo, Steps to 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...
Aqua Aloha Surf Waikiki 810 Superior Studio with Lanai and Partial City View
Aqua Aloha Surf Waikiki 810 Superior Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed + (1) Queen Futon, Sleeps 3, 335 Sq Ft.Aqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are...
Westin Ka'anapali - Beautiful Resort On The Beach! Family Friendly! Island View!
The Westin Kā‘anapali Ocean Resort Villas South, located on Maui’s renowned Kā‘anapali Beach, offers an upscale island escape. These spacious villa-style accommodations feature kitchens, private lanais, and luxurious touches. Enjoy multiple pools, a spa, fitness center,...
Wailea Ekahi Village 26D - 1 Bedroom Garden View Condo
Escape to paradise in this beautifully appointed one-bedroom vacation rental nestled in the lush tropical gardens of Wailea Ekahi Village. Located on Maui’s sunny south shore, 26D is a tranquil second-floor unit that offers the perfect blend of privacy, comfort, and...