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.
Waikiki Shore 1016 Ocean View 1 Bedroom
Take in breathtaking ocean views from this one bedroom, one bath condo — located in the only condominium building directly on Waikiki Beach. Ideal for couples or small families, this relaxing retreat offers all the comforts of home just steps from the sand.Unit 1016...
Characterful and bohemian, this fully furnished studio has a large screened lanai and outdoor kitchen. The 550 square foot space sits on a private half acre of beautiful land with abundant fruit trees including starfruit, coconut, breadfruit, citrus, and lychees. The...
Enjoy the island breeze & afternoon sunsets in your island condo, Ground Floor
Located in Lihue, this charming condo offers a peaceful retreat for guests. With two comfortable bedrooms featuring queen beds and a cozy living room that includes a twin bed, there’s plenty of space to relax. The two bathrooms make getting ready easy and convenient....
Lani One’ā: A Handcrafted Island Sanctuary with Seaside Community & Aloha Spirit
This charming, elevated home in Pahoa, Hawaii, blends modern comfort with island charm. Painted in soft green hues that complement the lush tropical surroundings, this rental is perfect for a relaxing escape.
Kanaloa at Kona Ocean View 2 Bedroom
Beautiful condominium situated on 16 acres of a secluded oceanfront lava flow overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscapes. Golfers, families and outdoor enthusiasts will enjoy snorkeling, golf and deep-sea fishing...
New Listing! Private Maui escape with Island charm
Welcome to Alaeloa 35 – Your Private Maui Getaway! Tucked within the peaceful, oceanfront enclave of Alaeloa in Napili, Alaeloa 35 is a charming 3-bedroom, 2-bath freestanding cottage that effortlessly blends island comfort with timeless Hawaiian charm. Surrounded by...
Gorgeous, Newly Built, Cabin- Off the Grid & 10 Minutes from Black Sand Beaches!
Unwind in Pahoa at this tranquil cabin. Nestled in trees and nature, but only 10 minutes from the warm black sand beaches, the turtles love too, make this the perfect spot! The Best of both worlds only 10 minutes apart and down a convenient paved road, on the upper side...
Puna Rainforest Retreat Hot Spring-Ocean views on 20 acre Estate
Enjoy the solitude of Hawaii's rainforest on a lovely 20 acre estate. This ocean view home is super clean and spacious, on gated private property and very comfortable for up to 10 guests. Appreciate the rainforest sounds, rainbows, starry skies and sunshine, far from...
Waikiki Getaway! Pool, Near Honolulu Museum of Art, Parking!
Sandy beaches or exciting adventures--look no further than this Oahu property!This listing is for a room within a hotel.✦ Your room is 300 sq. ft, equipped with complimentary toiletries, high definition 40-inch TV, available with Premium cable.✦ Cleaning services...
Christmas Week 2024 Westin Kaanapali Ocean Resort Villa - Full Resort Access!!
Christmas week: 12/20/2026- 12/27/2026Westin Kaanapali Ocean Resort Villas - stunning property.Garden/Island View 2 Bedroom Lock-off UnitWith views of the West Maui Mountains and the beautiful resort grounds, guests can enjoy Westin's unrivaled luxurious Two Bedroom...
Westin Ka'anapali Ocean Resort Villas 1 Bedroom Villa Ocean View
The Westin Ka'anapali Ocean Resort Villas - whale watching, snorkeling, sailing, windsurfing and scuba diving just steps away, there are plenty of activities at our Maui beachfront resort near Lahaina - comes with Westin touches keeping in harmony with the Hawaiian...
30 Day Rental in Waikiki with Parking!
Welcome to Fairway Villa, your ideal retreat in the heart of Waikiki! This studio, available for a minimum 30-day stay, is perfect for remote workers, traveling nurses, or anyone needing a longer-term stay in Waikiki. The studio features a comfortable Queen-sized bed, a...
Peaceful Peacock Palace in Makaha
Nestled in the lush landscapes of Makaha Valley, backed by the beautiful Mountains with a 24 hour Oceanview, our enchanting retreat offers guests a unique blend of serene natural beauty and luxurious comfort. As you enter the gates, you are welcomed by the sweet...
Hilton Hawaiian Village Lagoon Tower 2BR 2BA sleeps 6--Ocean View
Consider this condo your home away from home while you visit Honolulu. Lagoon Tower offers 2 bedrooms and 2 bathrooms, ensuring a comfortable stay for guests. With amenities like a hair dryer, heating, WiFi, a washing machine, an iron, a fitness room, and AC, your needs...
Brand New_Tropical Modern Style
Looking for a quiet, peaceful, and relaxing place to stay while visiting the Big Island? Well, Look no further. We offer you a beautiful & Newly built ohana unit that eludes a modern-tropical aesthetic feel; just minutes away from the Ellison Onizuka Kona International...
Aqua Aloha Surf Waikiki 1405 Studio w/Lanai & Partial City Views
Aqua Aloha Surf Waikiki 1405 Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach. A surfer’s lifestyle is all about being inspired by the ocean, hitting the beach for sun therapy, and laid-back living with aloha,(1) Full/double bed, (1) Twin...
New Listing! Waikoloa Colony Villas, Sleeps 6, AC by Coldwell Banker
Colony Villas 2004 – Spacious Luxury Townhome in Waikoloa Beach ResortWelcome to Colony Villas 2004, your perfect tropical escape on the stunning Kohala Coast of the Big Island. Nestled within the private, gated community of Waikoloa Colony Villas, this beautifully...
Kaimana Beach Hotel | Classic Queen | Beachfront Getaway
Tucked at the serene end of Waikiki, Kaimana Beach Hotel offers direct beachfront access, steps from Kapiolani Park and beneath Diamond Head. The Classic Queen is a cozy retreat with a plush bed and breezy island-inspired design. It's perfect for solo travelers or...
** 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...
Chic Coastal Living in the Heart of Wailea
A brand-new split air-conditioning system has been installed throughout the property, ensuring year-round comfort with contemporary efficiency and quiet operation.This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to...
Kai Lani 21C: Spectacular Ocean Views, Upgraded 2BR Condo
Welcome to Kai Lani 21C by Gather, an elegantly upgraded upstairs condo located in the pristine Ko Olina Resort. Offered as a monthly rental, this home provides a luxurious escape framed by unobstructed Pacific Ocean views, sophisticated interiors, and direct access to...
** 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...
Snowbird-friendly home near the beach with patio, grill, outdoor dining area
Hale Olena Ohana - 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located just 26 blocks from the ocean, this snowbird-friendly home offers the perfect...
Direct Oceanfront unit that will take your breath away. Sugar Beach 528
Book with us and come to Maui to explore everything we have to offer!Incredible views in a well maintained oceanfront unit right over the beach. Take time to relax with your morning coffee as the whales swim by. Amazing unit at amazing resort. Enjoy your Lanai...
Royal Kahana Maui 415 Ocean View 1 Bedroom
Enjoy the perfect blend of comfort and stunning ocean scenery in this charming one-bedroom near white sand beaches. Great for couples, honeymooners, or nature lovers. Unit 415 Ocean View 1 Bedroom 1 Bath• 4th floor condo with nice views of ocean and the island of Lanai...
Kihei Kai Nani 134 - 100 Yards From Beach
About this spaceBEST PRICE for the best vacation across street from Kamaole 2 beach on Maui. The condo is on the ground floor and the third one from the right end of building 12 across the driveway from the pool. The condo complex is not pet-friendly and smoking is...
We are a 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.This rental is composed of 1 Suite and 1 Cottage.We have a brand new split system AC and heating in every room and...
36FL Newly Renovated Condo with Gorgeous Ocean View
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Escape to this newly renovated 600 sqft ocean-view condo on the 36th floor of Waikiki Banyan, perfect for...
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront communities....
Westin Nanea Ocean Villas Resort & Spa, Hot Tub!
A state of relaxation and repose - firsthand at The Westin Nanea Ocean Villas! Set on twenty-six acres of lush, tropical land and infused with a variety of Hawaiian design elements, The Westin Nanea Ocean Villas blends a top-notch vacation experience with the authentic...
Alii Park Place#N-202: Gorgeous Remodeled Top Floor 3 Bedroom unit with AC
Alii Park Place is one of the premier developments on Alii Drive. Tinguely Development group created this complex wanting to offer true quality living. It's clearly apparent this reigns supreme as you walk into the space. Unit#N-202 is beautifully furnished, and offers...
Private Napili Nest Near Beach
Tucked away, yet within minutes of Napili Bay, Kapalua resorts, golf, hiking and restaurants, Napili Nest is a private, remodeled and well-appointed end-unit studio with an A/C, a balcony, peek-a-boo ocean/garden view and thoughtful guest amenities. Located in a quiet,...
*Free Parking!* Palms at Waikīkī Hotel
This elegantly remodeled unit is located in the heart of Waikiki. Just steps away from world-famous Waikiki Beach, this condotel is across from the Hilton Hawaiian Village, Fort DeRussy Parkl and short walk to the Ala Moana Shopping Center. Restaurants, grocery stores,...
Elegant Island-Inspired 2-Bedroom with Ocean Views
Mahina Surf 205 is sure to impress! Stunning tropical hues greet you the moment you walk in. New and modern furnishings, Maui-inspired designs, and artwork throughout the condo transport you to the perfect beachy abode where you can instantly unwind and enjoy the beauty...
Waikiki Serenity – Modern Luxury & Views
🏨🌺🏖️Escape to our prime Waikiki retreat! Steps from the vibrant International Market, our cozy condo is a beach-lover`s paradise. Unwind with 180° views from your spacious lanai, just a stroll to the ocean`s embrace. Relish the buzz of the city and the comforts of home...
Colony Surf Hideaway: 2BR Beachfront Condo w/ Views & Tub
Welcome to Colony Surf Hideaway, an upscale beachfront retreat perched along Honolulu’s prestigious Waikiki Gold Coast with uninterrupted views of Diamond Head and the shimmering Pacific. This newly updated 2-bedroom, 2-bathroom sanctuary blends refined island style,...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Close To Beach | 2 Units, 5 Bedrooms | HK ML-1643
** 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...
Wailea Ekahi Village 52D - 1 Bedroom Garden View Condo
Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...
Wailea Elua Village 706 - 2 Bedroom Ocean View Condo
Welcome to your dream vacation retreat in Wailea! As you step inside the newly renovated Wailea Elua 706, you\'ll immediately be captivated by the spacious and thoughtfully designed interior. The open concept living area is flooded with natural light, creating a warm...
Makaha Valley Oasis 1-Bedroom | By The Ocean
Indulge in a peaceful island escape with panoramic views of Makaha's lush and quiet valley and ocean views minutes from the nearest beach park. From frequent rainbows to wild peacocks roaming the grounds to dolphins, whales and turtles dotting Oahu's west side beaches,...
Aqua Aloha Surf Waikiki 1201 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki #1201 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen sofa sleeper, sleeps 4, 360 Sq ft.Aqua Aloha Surf Waikiki offers a range of accommodations that are...
Luxury family villa 5bd - Ocean Views - Center of North Shore
Luxury North Shore Villa – 3 Bedroom with 5 bed | 5 Bath | Ocean Views | Sauna | Welcome to your dream getaway on the iconic North Shore! This brand-new luxury villa offers the perfect blend of indoor-outdoor island living with stunning panoramic ocean views and just...
Royal Sea Cliff Kona 303 Garden View 1BD 1BA
Surrounded by tropical greenery, this charming one-bedroom condo offers a peaceful island retreat. Perfect for couples or solo travelers, it features all the comforts of home on the beautiful Kona coast. Unit 303 Garden View 1 Bedroom 1 Bath• Ground floor condo...
Queen Bed | Outrigger Waikiki | Shopping & Dining in Central Waikiki! Gym, Pool!
Aloha, and welcome to your tropical playground on Waikiki Beach!This listing is for a room within a hotel.✦ Your room is 234 sq. ft, equipped with complimentary toiletries, high definition 55-inch TV, available with Standard cable, and Premium cable.✦ Cleaning services...
Making The Best Memories Along The Way! Outdoor Pool, Oceanfront Property!
This listing is for a room within a hotel.✦ Your room is 270 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.✦ Cleaning services availability and frequency vary by stayThere are a few additional details to know...
Fairways Villas at Waikoloa E4 Golf View 2 Bedroom
This spacious condo overlooking the fairways offers a peaceful island escape. Perfect for families or couples traveling together, it combines comfort, space, and easy access to beaches and golf. Unit E4 Golf View 2 Bedroom 2 BathFairway Villas is located at 69-200...
** 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...
Discovery Bay 1 Bedroom Deluxe Ocean View, Near the Beach!
Experience island living with comfort and style in this 37th-floor ocean-view condo at Discovery Bay! This inviting 1-bedroom unit features a queen bed, sleek vinyl flooring, refreshed furnishings, and a modern design perfect for a relaxing getaway or extended...
Picturesque views of the ocean and Diamond Head
Mesmerizing panoramic views of Diamond Head, the blue Pacific Ocean, the moon and stars! This spacious corner condo is as close as you can get to the sand without being on the beach. Step back in time for this rare opportunity to stay for a while in the home of a...
** 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...