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.
KAS 8409 Ocean Views from this Freshly Updated 2BD Kihei Maui Condo
FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S1)*One ticket per...
Pool House Studio with King Bed – Poolside Retreat
Stay poolside in this spacious 484 sq. ft. studio featuring a king bed, a sofa bed, and a convenient wet bar. With modern amenities like air conditioning, free Wi-Fi, and a flat-screen TV, this studio is perfect for a laid-back and refreshing escape.Key Features: •...
Best 3 bed villa by the beach
Summary:Treat yourself to vacation of a lifetime in this tastefully remodeled villa that opens to beautiful sunsets every night. Located across the lake (short walk) from golf, shopping, coffee, beach. King bed on 1st floor with no steps. Oversized main with king bed,...
Walk to Beach from Lux Condo w/Hilton Pool Pass
When you stay at our 3/2 nestled between the Hilton and Marriot, you're steps to the beach and a 5-10 minute walk to shopping, groceries, beach-front dining, a luau, a movie theatre and ancient ruins. The location simply does not get better in this resort area!Located...
Ocean Front Suite: with Seating Area and Balcony, Outdoor Pool, Pets Are Welcome
Discover Moloka'i, a peaceful island nestled along Kamiloloa Beach and Hawaii’s only barrier reef, just minutes from Kaunakakai, the island’s main town. Immerse yourself in its rich culture as you explore the birthplace of Hula, wander through lush hiking trails,...
Breathtaking Location! 2 Modish Units, Near Hulihee Palace, Kona Snorkel Tours!
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
Paradise resort home in Ko Olina Coconut Plantation
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Lahaina Shores 533: Romantic Oceanfront Studio
Lahaina Shores 533 – Oceanfront Romance & Unforgettable ViewsPerched on the 5th floor of the beloved Lahaina Shores Beach Resort, this beautifully renovated studio offers an unbeatable combination of modern luxury and timeless island charm. With first-class décor,...
Serene Makaha Retreat
Discover serenity at our home. 3 beds, 2 baths, steps from world class Makaha beaches. Enjoy a spacious retreat with a fully equipped kitchen, outdoor BBQ, and scenic views. Nearby hiking, golf, and local attractions. Safe and convenient. Your Hawaiian escape awaits!
1BR Waikoloa Village Condo - 1 Bath, 2 Beds
Discover your Big Island paradise at Marriott's Waikoloa Ocean Club Resort, right on Waikoloa Beach's gorgeous sands.This dream location offers on site relaxation with:- a pool- beach access- spa- golfAdventure awaits nearby:- explore jungle trails by foot or horse-...
Cozy studio condo with AC and WiFi in charming Koloa/ Poipu
Nestled in Koloa, this delightful condo is a tranquil oasis for guests seeking a serene getaway. With a cozy bedroom and a well-equipped bathroom featuring a shower and hair dryer, this gorgeous property provides all the comforts of home. Enjoy modern amenities like...
Royal Kahana Maui 605 Ocean View Studio
- 6th floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry, kitchen, bathroom and...
Comfortable Studio for 2 | Full Kitchenette
Spend your next vacation discovering the beautiful beaches and stunning hikes in Oahu! Our comfortable Studio for 2 is conveniently located close to numerous shops and restaurants! Soak up the sun on Waikiki Beach, only 7 minutes away. We think you'll love:• Studio...
Serene Waikiki Studio Getaway - Peaceful Retreat Close to Beach and Hospitals
Welcome to the Serene Waikiki Studio Getaway, a thoughtfully designed, fully furnished studio in a quiet part of Waikiki near the Ala Wai Canal. This beautiful, newly renovated space is perfect for those seeking both tranquility and convenience, whether you’re here...
Charming oceanfront coastal getaway
Welcome to Kulakane 207, a wonderful oceanfront condo in West Maui. This charming 1-bedroom, 1-bathroom is on the 2nd floor and offers stunning unobstructed ocean views that accommodate up to 4 guests. Please note this resort does not have elevators. As you step into...
Kanaloa at Kona Partial Ocean View 2 Bedroom
- Condos located on 1st or 3rd floors- Private balcony with wet bar- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Master bedroom with 1 king bed or 1 queen bed and private bathroom with...
Oceanfront Suite with Private Balcony at OUTRIGGER Waikiki Beach Resort!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! With comfortable amenities and authentic Hawaiian hospitality, you'll have everything...
Tropical Tranquility and Sunset Views! Maui Vista 2223
Tropical Tranquility and Sunset ViewsWelcome to your perfect Maui getaway! Nestled in the heart of South Kihei in the desirable Maui Vista Resort, this beautifully renovated condo offers the ideal blend of comfort, convenience, and island charm. Whether you’re seeking...
New Listing! Ground floor oceanfront blue oasis
Nohonani 101 is a spacious two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. With a king-size bed in each bedroom and a queen sleeper sofa in the living area, there's plenty of room for families or small groups to relax and unwind. Although...
1 Bedroom Condo-Princeville, Kauai-Family Friendly!
Perched above the sparkling waters of Hanalei Bay, this resort offers families a front-row seat to some of Princeville’s most awe-inspiring natural beauty—from the dramatic Na Pali Cliffs and iconic Bali Hai Mountain to cascading waterfalls, golden beaches, and palm...
Moani Heights 9013 - Luxurious Island Retreat
Rest and recharge in this luxurious four-bedroom, four-bath island retreat, where indoor comfort meets stunning outdoor living. The open-concept kitchen and living area flow seamlessly onto a spacious, furnished lanai, perfect for enjoying the coastal breeze. Step...
Turtle Bay Studio
Experience the North like a local in this charming studio. The cozy space features 1 queen bed, a bathroom with a shower, and amenities like AC and even bikes to use. Enjoy the enchanting surroundings and relax in this amazing retreat. Whether you're here for a weekend...
Christmas Week Dec 19-26th at The Westin Nanea ocean resort on Kaanapali beach
Special week December 19th - 26th!!!!!Experience Nanea - a state of relaxation and repose - firsthand. Resort blends a top-notch vacation experience with the authentic history and culture of Hawaii. Amenities include a 10,000 square foot lagoon style pool with a upper...
Relaxing upcountry retreat on the slopes of Haleakalā. Ideal for families.
After a hot day at the beach, relax at Ke Kīhāpai Bed & Breakfast at the 2400 foot elevation with unobstructed views of our dormant volcano, Haleakalā. Breathe the fresh air with an upcountry view of town, the north shore of Maui and Kahālāwai (West Maui...
Golf Villas Ocean View 1 Bedroom at The Kapalua Villas Maui, Full Kitchen
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Escape to Paradise! 2 Serene Units, Pool, 3 Restaurants, Right on Beach!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Lahaina Shores 421 - Studio Oceanfront Condo
Lahaina Shores 421 - Studio Oceanfront CondoLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 421 is a Studio unit on the 4th floor, offering comfort and accommodations for up to 2 guests. Step...
The Westin Kāanapali Ocean Resort/ 2-Bedroom
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour...
Wyndham Royal Sea Cliff | 2BR/2BA King Balc Suite
Summary:Nearby Pu‘uhonua o Hōnaunau, an ancient sanctuary whose name means "the place of refuge," could easily describe this resort. Oceanfront, modern, and conveniently tucked outside Kailua-Kona, tranquility reigns. It’s the ideal home-base for all of your island...
Long term rental Marina Front rental in Hawaii Kai with pool
Beautiful house marina front in Hawaii Kai with pool is available for long term rentalThree bedrooms, two baths, fully furnished with internet and utilities included.30 day minimum rental, no exceptions$18,800/month
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
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.Find peace and tranquility in your very own...
Pool House with 2Queen Beds – Poolside Comfort
Enjoy a relaxing poolside retreat in this 484 sq. ft. studio featuring two queen beds and a wet bar. With air conditioning, free Wi-Fi, and modern comforts, this studio provides a perfect blend of convenience and luxury for your stay.Key Features: • Design-Centric...
Royal Sea Cliff Kona Garden View 2 Bedroom
Garden View 2 Bedroom 2 Bath- Condos located on 1st, 4th and 5th floors- Private balcony- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, cookware and tableware- Master bedroom with 1 king bed and private bathroom with...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
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.Stay at Kailua Beachside by Gather, a...
Newley remodeled and beautifully furnished downtown Kailua-Kona condo.
Located on the ground floor at Kona Plaza Condominiums, Unit 107 is newly remodeled & just steps away from downtown Kailua Historic Village & the Kailua Pier. Decorated with a taste of Hawaii that will set the mood to kick start your Hawaiian adventures. Fully furnished...
Island Surf 510 | Water Views, Across from the Beach + In the Heart of Kihei!
Escape to the serene paradise of Island Surf 510C, a cozy tropical condo nestled in the heart of Kihei, Hawaii. This charming vacation rental offers a tranquil retreat for up to 4 guests, boasting 2 spacious bedrooms and 2 bathrooms all conveniently situated on one...
Konishiki Beachhouse: Luxury 4BR Oceanfront Home w/ Private Pool, Beach 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.Welcome to Konishiki Beachhouse 4BD by Gather,...
Kapalua Golf Villas Ocean View 2 Bedroom
Golf Villas Ocean 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 and bathroom- Guest bedroom with 2 twin beds;...
Butterfly House: Beautiful Ali'i Drive Home with Ocean Views!
Incredible Modern Alii Drive Home with Ocean Views! A beautifully renovated home right across Kahalu'u Beach on the historic Ali’i Drive.Modern finishes throughout. 2 Master bedrooms with 2 full baths. Modern fixtures in all areas of the home.Stay cool with ceiling...
2/2 Modern & Elegant Penthouse Oceanfront Vistas
Summary:Spacious and elegant. Completely remodeled in December 2022, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is...
Puna Rainforest Retreat Hotspring - Purple Passion Cottage
The Purple Passion Cottage is located on a serene 20 acre estate with beautiful ocean and meadow views. The cottage is cozy and equipped kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed with an...
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,...
Lahaina Shores Oceanfront Corner Location ~ Unit 601
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...
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...
Marriott Ko Olina Beach Club - On The Beach- Family Friendly
Come experience Hawaii at this premium level Marriott Resort in Oahu. With luxurious amenities and great family entertainment, your family won't want to leave.This property has everything you need for a tropical vacation. There is a lagoon style family pool with...
Hawaiian Oasis w/ Private Pool, 2 King Suites & Sunset Views!
Discover true Aloha at this stunning private 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...
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,...
Relaxation Bungalow with Hot tub, Sauna, Lush Garden, and Pristine Island Living
Escape to Hale Kalani, a charming 3-bedroom surf bungalow nestled in the heart of Princeville on Kauai’s renowned North Shore. Thoughtfully designed for relaxation and island living, this single-level haven features a private cedar barrel sauna, a brand-new hot tub,...
Marriott Maui ocean club full kitchen, washer dryer 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.• Waikiki...