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.
Marriott Vacation Club, Waikiki 1BR sleeps 6
Summary:Escape to Marriott Vacation Club, Waikiki, a vacation ownership property in the heart of Honolulu. Centrally located in a premier shopping and dining district near Waikiki Beach. Each offers a kitchenette, dining area, and premium amenities including a rooftop...
NEW! KBM Resorts | FREE CAR | Oceanview Luxury Villa | Hale Moana At Montage Kapalua Bay, Sleeps 10! 3-Bedroom Condo with Daily Housekeeping, Spa! MON
** 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...
3 Partial Ocean View Units, Pool, 3 Restaurants, Minutes to Waikiki Beach Walk
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...
Napili Point | 2 Free Rental Cars | KBM Resorts | Water Front | 2 Units, 4 Bedrooms | NAP ML-2096
** 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...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Ocean Front | 2 Units, 6 Bedrooms | HK ML-1101
** 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...
Kaanapali Alii 194
Welcome to Kaanapali Alii 194, your perfect luxury vacation rental nestled in the heart of Lahaina. This stunning two-bedroom, two-bathroom condominium offers breathtaking views of the Pacific Ocean and is a short walk to the pristine Kaanapali Beach. Ideal for families...
Hale Alapi'i Lanikai Getaway: Newly Renovated Near Beach & Hiking
Just a short stroll from turquoise water and powder-soft sand, Hale Alapi‘i Lanikai Getaway by Gather is a serene 4-bedroom, 3-bath retreat set in Kailua’s coveted Lanikai neighborhood. Recently renovated interiors meet breezy outdoor living, surrounded by tropical...
Peaceful 1-Bedroom in a Quiet Community
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...
New Listing! Colorful 1bd on the 3rd floor
Welcome to Valley Isle 301, a beautiful 1-bedroom, 1-bath condo with stunning ocean views, located just steps from the beach between Kaanapali and Kapalua. This spacious third-floor unit comfortably sleeps up to four guests and offers the perfect blend of island charm...
KHV 34 Direct Ocean Front Views 2BD Kahana Condo
Kahana Village 34 NEW LISTING Amazing 2 Bedroom, 2 Bathroom, West Maui Beachfront Getaway Steps to the Beach, Pool, and Hot Tub! Wake up to the sound of waves and breathtaking views at this beautifully remodeled two-bedroom, two-bathroom, two-story condo at Kahana...
Royal Sea Cliff Kona 306 Garden View 2 Bedroom
- 3rd floor condo with lanai on the south side of the building- Maximum 6 persons including children and infants- Master bedroom with 1 king bed and bathroom with walk-in shower and double sinks- 2nd bedroom with 1 king- Queen sofa sleeper with premium mattress in...
Kiahuna Plantation Resort 195 Oceanfront 1 Bedroom
- Second floor oceanfront condo with unobstructed ocean views- Walk-up, no elevators- Tropical beach décor and original artwork by Coco in the living area- Custom tiled floors throughout- Custom kitchen with upgraded stainless steel appliances, microwave, full size...
Tropical Oceanside Oasis - A bright and spacious studio on the beach!
Bask in the sunshine & aloha while relaxing in our bright, spacious & serene studio. The property boasts lush, tropical surroundings filled with swaying coconut trees, birds of paradise, orchids & koi ponds. This comfortable, airy top-floor unit is a stone's throw from...
Hualalai Golf Villa - Exquisite Views & Fully Remodeled
Welcome to your dream vacation at our spectacular Hualalai Resort Golf Villa, perfectly situated overlooking the 18th fairway of the world-renowned Hualalai Resort Jack Nicklaus Signature Course, with captivating ocean views beyond. This second story front-row Villa...
2 Bedroom Lockoff Villa at Westin Ka'anapali Ocean Resort Villas
Spread out with the whole family in this spacious two-bedroom suite.If the majesty of Maui’s beaches and mountains weren’t enough to sell you on a trip to Hawaii, perhaps the allure of this world-class wellness resort will tip the scale. Situated on Ka’anaplai...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Extra Large Lanai | 3 Units, 5 Bedrooms | HK ML-1233
** 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...
KHV 26 2BD Direct Ocean Front with Amazing Sunsets
Kahana Village 26 NEW LISTING Enjoy West Maui Like Never Before from this Relaxing Island Oasis, with Sunsets from the Beach Front Pool, Hot Tub, and BBQ's! This two-story retreat offers the perfect combination of space, comfort, and breathtaking views of the Pacific...
Beachfront Retreat: Elegant Views w/ Full Kitchen. Onsite Parking and Pool!
Step into your spacious and beautifully designed suite, where modern comfort meets tropical charm. Each unit features a fully equipped gourmet kitchen, furnished lanai, in-room washer and dryer, and luxurious bedrooms and living areas.Why Stay Here?Whether you’re...
Waikiki Beach 1-BR Oceanview Condo...Steps to the Sand!nBeachviews.
Welcome to your ownWaikiki Beach 1-Bedroom Oceanview Vacation Condo Rental...just steps to the sand,Famous Waikiki Locale. One of the few beachfront condo properties in Waikiki, Relax on our Spacious Lanai framed by coconut palms, in a beautiful tropical setting. Steps...
Ridge Villas Gold Ocean View 2 Bedroom at The Kapalua Villas Maui
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...
Royal Garden at Waikiki | Two Studio Suites
Summary:This listing is for 2 Studio Suites at Club Wyndham Royal Garden at WaikikiEach Studio Suite Features:• Size: 311 - 381• Kitchen: Partial• Baths: 1• Accommodates: 2 Guests• Beds: King Bed - 1Room Amenities• Hairdryer• In Room Safe• Broadband...
4 Bedroom Ocean View Home w/Private Pool
*Please note that this private home requires a minimum stay of 30 nights for bookings online. If you are interested in a shorter stay, please call our reservations team to discuss options.Feel a sense of serenity wash over you the moment you step inside your Hale Malie...
Keauhou Palena#1403 Top floor, Exquisite Stunning Remodel on Golf Course!
"WOW!" A Truly Stunning Keauhou Palena condo, nestled in the historic Keauhou Bay area—just a short distance from the bay.This upstairs unit was thoughtfully and completely renovated in 2023, showcasing exceptional attention to detail. Enjoy peekaboo ocean views from...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | 180 Degree Views | 2 Units, 3 Bedrooms | KBV ML-1999
** 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...
Kaanapali Alii | 462
Welcome to Kaanapali Alii 462, your luxury vacation rental nestled in the heart of Lahaina, Maui. This stunning one-bedroom ocean view condo offers a perfect blend of comfort and elegance, making it an ideal short-term rental for your Hawaiian escape. Step into a...
Royal Kahili 401A by Gather: Oceanfront Suite & Resort Pool
Experience oceanfront elegance at Royal Kahili 401A, a top-floor corner suite in Kailua-Kona, Hawai‘i. This stunning two-bedroom, two-bath retreat spans 1,029 square feet and offers panoramic views of the Pacific Ocean, blending modern comfort with island serenity....
8th Fl Waikiki Sunset | Parking | Pool | AC
Stay just one block from world-famous Waikiki Beach in this 8th-floor condo, complete with free parking and WiFi. Perfect for families, couples, or friends, this comfortable retreat offers a convenient location close to the beach, Honolulu Zoo, Kapiolani Park, shopping,...
Oasis Retreat: Beautiful 4BR 2BA
Welcome to our Serenity Retreat in the heart of Mililani, Hi. Our retreat is nestled in a peaceful neighborhood and offers a perfect blend of comfort and serenity, making it an ideal getaway for those seeking a rejuvenating escape.This particular unit is located at the...
Oceanfront Paradise | Maui Sunset 2BR/2BA Condo
Welcome to your Maui getaway at the beautiful Maui Sunset Resort in Kihei. This spacious 2-bedroom, 2-bathroom vacation rental offers the perfect combination of comfort, convenience, and breathtaking oceanfront views. Whether you’re traveling with family, friends, or...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Extra Large Lanai | 2 Units, 4 Bedrooms | HK ML-1239
** 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...
Kaanapali Alii Unit 181v
Welcome to Kaanapali Alii Unit 181, a luxury vacation rental nestled in Maui's exclusive Kaanapali Alii Resort. This deluxe condominium offers a stunning view of the Pacific Ocean, framed by swaying palm trees and the pristine grounds of Kaanapali. Immerse yourself in...
Sunset Shores - Waialua Oceanfront Retreat - 30 Day Rental
**This property may not be rented for less than 90 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied**Welcome to Sunset Shores! Located in Waialua on the North Shore of Oahu, this...
37FL-Upgrade 1BR-Ocean View Full Kitchen w/Parking
A perfect ocean view from the 37th floor! This beautifully renovated, bright, and breezy condo is ideally located just steps away from Waikiki Beach and Kapiolani Park — the perfect getaway for couples or small families. Enjoy from the large windows, you’ll be...
Walk to Charley Young Beach - 2BR/2BA Kihei Condo w/ Pool, AC & Haleakalā View
Our 2BR/2BA condo is perfect for families and groups. With split AC in every room, memory foam toppers on both queen beds, and plenty of space to relax, it’s a true Maui home base. • Primary Suite: Queen bed, walk-in closet, private bathroom • Second Bedroom:...
Luxury 1-bedroom villa in welcoming Princeville, Kauaʻi with WiFi, AC
Your home away from home in Princeville, Kauaʻi with 1 bedroom. This marvelous villa features a cozy living room with a sofa bed, perfect for relaxing after a day of exploring. The bedroom boasts a comfortable king bed for a restful night's sleep. Enjoy modern...
Aloha Living at Waikiki Lanais | Pool + Gym
Enjoy views of the palm tree dotted Ala Wai and lush mountains from our 1 bedroom / 1 bathroom apartment at the Waikiki Lanais building. This property features a full kitchen, breakfast bar, dishwasher, dining area, and private lanai. Building amenities include a...
LUXURY 2-Bed Condo, Kitchen, Wi-Fi, Parking, W/D, AC, LEGAL Monthly Rental!
Allure Waikiki Penthouse #3504 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki penthouse living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...
Wyndham Paniolo Greens | Five 2BR/2BA Suites
Summary:This resort is a lush, tropical retreat in the heart of Hawaii's Big Island featuring spacious suites with private lanais. Explore all the island has to offer with golf and beautiful beaches located just minutes away, or stay on-site and enjoy the many amenities...
Maui Resort Rentals: Honua Kai - 6 Total Bedrooms with Over 3800 Combined Sq Ft and Stunning Premier Ocean Views!
This exceptional pairing combines a stunning 3BR Premier Oceanview suite overlooking the resort's lush interior courtyard and pools with a neighboring 3BR Oceanview suite offering not only stunning views of the blue Pacific but also vistas of the majestic West Maui...
Sugar Beach PH17 - Direct Oceanfront 1 bedroom
Aloha! When you think about Hawaii, do the following images come into your mind? The blue Pacific ocean? Long sandy beaches? Palm trees swaying in the gentle breeze? Warm sunshine? Tropical islands on the horizon? Stunning romantic sunsets? And also, in one word;...
Brand New Rental Direct Ocean Front Ko Olina Beach Villas
First time in rental pool! Owner previously used it as a vacation home only, barely occupied during the year.This ocean front 4th floor Beach Villa is located on Ko Olina Resort's pristine 2nd Lagoon in the Beach Tower which is closest to the beach. One of 14 true...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Amazing | 3 Units, 5 Bedrooms | HK ML-1772
** 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...
Maile Hale-Serenity Home
Experience resort-style living in this 5BR/4BA luxury retreat in Mauna Lani. Designed for relaxation and entertaining, the home features a private pool and spa with waterfall, lush tropical landscaping, spacious lanais, a gourmet chef’s kitchen, media room, and a...
Valley Isle Resort #1102 - Vacation West Maui
★Free Parking, Free Wifi, No Resort Fees★New Split Air Conditioner System in Bedroom and Living Room! New Vinyl Floors!!Escape to a haven of tranquility and breathtaking ocean vistas at Valley Isle Resort 1102, your beachfront condo on Maui's sun-kissed west coast....
🏖️Across from Magic Sands | Pool, AC, Tennis & BBQs
White Sands Village #224 | Across from Iconic Magic Sands Beach | 2-Bedroom, 2-Bath Condo with Central ACWelcome to White Sands Village #224 — a beautifully updated 2-bedroom, 2-bath condo, perfect for families or couples looking for comfort, convenience, and a prime...
Waikiki Skyline 28th Floor Hawaiian Monarch
Located in Honolulu, this hotel suites is a dream. With a cozy bedroom featuring a queen bed, a bathroom equipped with a hair dryer and bathtub, and convenient amenities like an iron and AC, guests will feel right at home. Experience a fabulous stay in the heart of the...
Relaxing oceanfront getaway with views from the lanai, shared pool and hot tub
Kona Bali Kai #404Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Kona Bali Kai, your oceanfront paradise in Kailua-Kona, Hawaii! Nestled along the stunning Aliʻi Drive,...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Exceptional Value | 2 Units, 3 Bedrooms | HK ML-1297
** 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...
Honua Kai Konea 307 Ocean View 2 Bedroom 2 Bath
Konea Unit 307 Konea 2 Bedroom Ocean View- Exclusive on-site provider with the only homes meeting the prestigious AAA 4-Diamond designation- Beautiful views of the Pacific Ocean and Kaanapali Beach from private spacious lanai with dining table, chairs and glass railings...