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.
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...
1000 steps from famous Lanikai beach
Welcome to your island sanctuary in one of Oahu’s most coveted gated communities—where privacy, luxury, and lifestyle come together in perfect harmony. This beautifully updated end-unit rental offers the ideal blend of tranquility and convenience, making it a dream...
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...
East Oahu Oceanfront Estate
Escape to this spacious 4-bed, 3-bath oceanfront retreat on Oʻahu’s peaceful east side, where golden sunrises and crystal-clear waters await just steps from your door. Sink your toes into the soft white sand right out back, take a morning stroll with coffee in hand, or...
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...
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
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 Watch 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...
Waikiki Grand 1005 - The Best location in Waikiki!
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...
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...
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...
Luxury 3BR Villa with Ocean Views – Marriott's Ko' Olina Beach Club
Step into paradise in this ocean-view three-bedroom villa at Marriott’s Ko Olina Beach Club, where comfort, space, and resort-style amenities come together for an unforgettable Hawaiian escape. Ideal for families or groups seeking relaxation and adventure, this villa...
Pesthouse 1 Bedroom Ala Moana Condominium, City / Partial Ocean from Lanai
Penthouse Unit on the 33rd Floor, with Beautiful City View & a Partial Ocean View from Lanai at Ala Moana Condominium.The unit has everything you might need for a convenient like home stay!It has a full kitchen to prepare your dinner, a big bathroom with a bathtub &...
Hip Hawaii Vibe w/AC, WiFi, Lanai, Modern Kitchenette – Waikīkī Grand #904
Castle at Waikīkī Grand #904 - Hawaiian décor defines this air-conditioned 204sf escape where the furnished lanai creates a perfect perch for morning coffee and evening mai tais. The upgraded kitchenette features granite countertops, mini-frig, microwave, and...
Relax & Explore: Spacious 2BR Suite at Maui Schooner Resort
Escape to the shores of Kihei with this two-bedroom suite at Maui Schooner, where Hawaiian ease meets roomy, well-appointed living. Designed to sleep up to six guests, the bedrooms are furnished with a king bed and a queen bed, and the living room includes a queen...
Royal Kahana Maui 205 Ocean View Studio
Experience island living at its best in this ocean-view studio, just minutes from Kaanapali Beach and Kapalua Bay. Great for couples or solo travelers. Unit 205 Ocean View Studio• 2nd floor studio with balcony overlooking lush gardens with views of the ocean and the...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms + Den w/ Stunning Ocean Views and Massive Wrap-Around Lanai!
This gorgeous 3 Bedroom/1 Den offering at The Honua Kai Resort on Kaanapali North Beach combines two best-in-class suites. The two-bedroom corner suite boasts deluxe ocean views from both the interior of the residence and the luxurious wrap-around balcony. The...
Kaanapali Alii | 285
Kaanapali Alii Unit 2851 Bedroom | 2 Bathrooms | Sleeps 2 | Ocean View________________________________________Welcome to Kanapali Alii 285, a stunning one-bedroom, ocean-view residence with a Platinum Rating. This bright and airy corner condo, situated on the 8th floor,...
Hale Ho’omaka by Gather: 2BR Condo w/ Lanai, Pool & Ocean Views
Hale Ho'omaka welcomes you to relaxed island comfort in Princeville. This two-bedroom, 1.5-bath home sleeps 6 guests, pairing bright coastal style with resort amenities and easy access to beaches and golf.What You’ll Love About Hale Ho'omaka • Two spacious bedrooms,...
The Lodge at Kukui‘ula - Cottage 11
Nestled along the breathtaking south shore of Kaua'i, Cottage 11 at the prestigious Lodge at Kukui'ula offers an unparalleled Hawaiian escape. This exquisite three-bedroom accommodation provides a perfect blend of luxury, comfort, and authentic island living.As a guest...
NEW Listing Oceanfront Home + Boards + Beach Gear
Directly across from Pokai Bay Beach, this stilted back unit duplex offers epic sunsets, ocean breezes, & sea/mountain views from two private lanais. The raised design allows for ample parking + ADDITIONAL bonus livingroom area. Enjoy snorkeling, paddling, surfing, &...
Kaanapali Alii 366
Welcome to Kaanapali Alii 366, a gorgeous condominium in Maui's exclusive Kaanapali Alii Resort. This lavish residence offers stunning unobstructed views of the sparkling Pacific Ocean and neighboring islands Lanai and Molokai. Vast windows and a private lanai mean you...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Modern Beachfront Studio At Honua Kai Resort | 2 Units, 4 Bedrooms | HK ML-1856
** 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...
Simple but modern. Tasteful yet elegant - Waikiki 1BR/1BA Condo
Aloha and welcome to your home away from home in beautiful Waikiki! We are thrilled to have you as our guest for your stay in our one-bedroom fully furnished unit. As you step into your cozy retreat, you'll find everything you need for a comfortable and unforgettable...
Maui Bay Villas by Hilton Grand Vacations Club - 1 Bedroom Plus
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol & Dettol, to...
Sleeps 16, 2 Homes | Ocean Views, Shared Pool + Gym, Near the Beach | AvantStay
Welcome to Mauna View & Ocean Escape by AvantStay! These two homes are just a few homes apart within the lush Makaha Valley, with a combined total of 6 bedrooms, sleeping up to 16 guests—an ideal option for groups looking to enjoy paradise together with a bit more...
Your Hawaii Vacation Awaits in Ko Olina (KoK-1029B)
Enjoy the Resort Lifestyle in this beautifully furnished, 3 bedroom 2 bath Ko Olina Kai rental. This is a perfect property for business travelers or long term vacation renters. The spacious master bedroom has a King size bed and master bath has dual sink and walk-in...
Maui Resort Rentals: Westin Ka'anapali Ocean Resort South 1BR Islandview Villa
Welcome home to The Westin Ka'anapali Ocean Resort Villas and enjoy the luxury you deserve on vacation! The Westin Villas property is legendary with amazing pools coupled with an incredible location on prestigious North Ka'anapali Beach. This spacious 800 sq ft 1...
The Cedar House - Private Yard and Entrance!
Welcome to The Cedar House! Just 5 minutes from world-class beaches and surf breaks. Enjoy country living with cool mountain breezes and the soothing sounds of nature, amidst coconut trees, bananas, and tropical plants. Local laws require a minimum 30-night booking, but...
🏖️30-Day Rental Ocean View Kona Home w/ Hot Tub
Aloha Vista – 30-Day Ocean View Retreat in Kailua-KonaWelcome to Aloha Vista, a newly built and beautifully designed 30-day vacation rental in Kailua-Kona where ocean views greet you the moment you step inside. Set at a comfortable elevation with refreshing trade winds,...
Luxury Ocean View Beachfront full-kitchen condo in Lahaina Maui
[New listing 6/11/22]A calm refreshing breeze came from the sea and ran through the living room. Half of it bolted out the front door and the other half through the bedroom, into the valleys of Maui.BEACH This is next to Kahana beach, part of Lahaina, a 10 minute drive...
Spacious 3 Bedroom / 2 Bath / Sleeps 8
Beautiful home located on the east side of Oahu in Hawaii Kai. Located near beaches such as the famous Hanauma Bay, eateries, shopping centers, hiking trails, scenic lookouts and water sports. The home offers 3 bedrooms (3 queen beds), 1 sofa bed and 2 bathrooms....
Oceanview Luxury Kaanapali Golf course 2BR Villa: Pool, Hot tub, Pickleball
Nestled in Lahaina, this upscale condo offers a terrific retreat for guests seeking comfort and convenience. With two spacious bedrooms featuring king beds, everyone can enjoy a restful night’s sleep. Travertine marble floors and an open floor plan give this condo a...
Poipu Kai Kahala 232 - One-bedroom Ocean View condo on the island of Kaua'i.
Poipu Kai Kahala 232 - One-bedroom Ocean View condo on the island of Kaua'i. Primary bedroom: King BedPrimary bathroom: full bath ensuite with single showerLoft: Queen bedSecond bathroom: full bath with single showerMax Occupancy: 4 peopleAC: NoneLaundry: in the...
Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View
Come explore Maui at this premium level Marriott property by the ocean. Surrounded by clear, blue waters of the Pacific, this dream getaway is the perfect place to enjoy your next tropical destination.This property has everything you need for a tropical vacation. There...
Kaanapali Alii 413
Kaanapali Alii 4132 Bedroom | 2 Bathrooms | Sleeps 4 | Garden View________________________________________Welcome to Kaanapali Alii 413, a beautifully appointed one-bedroom garden view condo with a fully enclosed den that comfortably serves as a second bedroom. Guest...
Paki Maui 222 Updated 2BD Oceanfront Retreat Steps from Pool & Hot Tub
Paki Maui 222 Freshly Updated Oceanfront 2 Bedroom Condo in the Heart of West Maui with Ocean Views Steps to the Pool and JacuzziWelcome to your Maui Retreat: This freshly updated oceanfront condo at Paki Maui offers a relaxed, comfortable place to settle in and enjoy...
Soooo close to the Beach! Premier Elua 2 Bdrm+2 Ba Condo #1702 - NEW LISTING
Treat yourself to a dreamy, beachfront 2 bedroom/2 bath Wailea Elua Village vacation home. The unit is located only steps to the pristine sands of Ulua Beach, and only a hop to the world famous Wailea Beachwalk. Upgraded and refreshed with lots of new personal touches,...
Pool Access: Ocean-View Molokai Shores Condo!
Scenic Outdoor Dining | Direct Beach Access | Community PerksImmerse yourself in the enchanting Hawaiian ambiance at this 1-bedroom, 1-bath vacation rental. Situated on the shores of Kaunakakai, this oceanfront condo boasts tranquil ocean views from the cozy interior...
Puunoa Beach Estates 201
Puunoa Beach Estates 2012 Bedrooms | 2 Bathrooms | Sleeps 4 | Oceanfront ________________________________________ Welcome to Puunoa Beach Estates 201, a luxurious two-bedroom oceanfront villa hugging the sandy shores of Lahaina’s Baby Beach. Dramatic ocean views,...
Aqua Aloha Surf Waikiki 806 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 806 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed+ (1) Queen Sofa sleeper, Sleeps 4, 360 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that...