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.
Relaxing Modern Oceanfront Suite–Sleeps 4 adults.
Enjoy this beautifully appointed oceanfront home in Kalapaki Bay. Take advantage of being centrally located with one of the best beaches and bays for SUP, beginner surfing, boogie boarding and more. The home is situated between 2 of the best resorts on the island. Enjoy...
** 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...
Always a Great Idea To Unwind! Partial Ocean View, Outdoor Swimming Pool!
The excitement of Waikiki Beach is at your doorstep at this Honolulu property!This listing is for a room within a hotel.✦ Your room is 453 sq. ft, equipped with complimentary toiletries, high definition 46-inch TV, available with Premium cable.✦ Cleaning services...
Kapalua Ridge Villas Fairway View 1 Bedroom
Ridge Villas Fairway View 1 Bedroom- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway - Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Bedroom with 1 king bed- Queen sofa bed in...
Ocean View 2BR at Marriott Maui Ocean Club – Ka’anapali Beachfront
Enjoy spacious island living in this two-bedroom ocean-view villa at Marriott’s Maui Ocean Club – Molokai, Maui & Lanai Towers, perfectly positioned on world-famous Ka’anapali Beach. Ideal for families or groups, this residence features a primary bedroom with a king bed...
Oceanfront Studio with Panoramic Views - Kapa'a Sands 07
Kapaa Sands 07 – Oceanfront Studio | Queen Bed | Pool AccessWake up to stunning ocean views at this second-floor beachfront studio on Kauai’s Royal Coconut Coast. Kapaa Sands 07 features 1 queen bed, a full kitchen, private lanai, and direct access to a peaceful beach...
Cozy Sunset Views w/ Lanai - Close to Beach by RedAwning
Escape the hustle and bustle of everyday life and immerse yourself in theserenity of our charming Kailua-Kona Ohana, a delightful 1-bedroom, 1-bathroomvacation rental. Located on the captivating Big Island of Hawaii, this coastalretreat offers a tranquil escape for...
Relax in this Modern vacation retreat located right across the street from Kailua beach park. Just steps from the white sand beaches of Lanikai/Kailua and minutes from local dining, shopping, and outdoor adventures. This thoughtfully designed home blends sleek...
Waikiki Studio with beautiful view and minutes to beach.
Fully furnished studio. Queen size bed sleeps 2. Complete kitchen, minutes from beach and shopping. Brand new air conditioner. Beautiful unobstructed view from 14th floor. Pool, BBQ lounge area and pay laundry on 5th floor. Near Bus routes to everywhere. This unit is...
** 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...
Making The Best Memories Along The Way! 2 Relaxing Units, Outdoor Pool!
When it comes to comfort, convenience, and an aloha spirit - you found the right place to stay. Relax by the pool, indulge in our buffet dinner, and enjoy views out over Kahului Bay. All this is yours within 10 minutes of the airport, and you'll be close to many of the...
Kaanapali Alii 4143 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Welcome to Kaanapali Alii 414 a beautiful 2-bedroom, ocean-view residence with with a fully enclosed den that comfortably serves as a third bedroom. Located in the...
Maui Resort Rentals: Hilton Maui Bay Villas - Luxurious 1BR Suite!
Nestled among 27 acres of lush tropical gardens, the Hilton Maui Bay Villas is a luxurious, secluded resort located on South Maui's sun-drenched coast. Situated minutes from several upscale resorts, pristine beaches, and championship golf courses, guests will enjoy...
Comfortable Studio at The Palms with Pool, WiFi & A/C - Sleeps up to 4 guests.
Unwind in Honolulu at this welcoming studio. This modern space offers a cozy living room with a queen bed and sofa bed, perfect for a peaceful retreat on the quiet side of the property. Enjoy the convenience of amenities like pool, WiFi, AC, and a hair dryer during your...
Kaanapali Alii Unit 2152 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Welcome to Kaanapali Alii 215, a gorgeous condominium in Maui’s exclusive Kaanapali Alii Resort. This deluxe ground-floor residence places Kaʻanapali Beach...
Historic Wailuku Inn: 10 Ensuite Bedrooms | Gourmet Chef Breakfast Included
Summary:Welcome to The Historic Wailuku Inn, a beautifully restored 1924 Maui estate with 10 private en-suite bedrooms, lush tropical gardens, and meandering plumeria-lined pathways. Featured by the Wall Street Journal (Apr 18, 2025) as an authentic alternative to...
New Listing 3 Bedroom on the Golf Course in sunny Poipu
Welcome to Pili Mai 7I, a stylish 3-bedroom condo in Kauai’s exclusive Pili Mai resort. Overlooking the lush landscape and Kiahuna Golf Course, this multi-level retreat is just minutes from Poipu Beach, shopping, and dining. Designed with classic plantation-style charm,...
🏖️Palm Villas at Mauna Lani | Private Beach Club | 2BR + Loft | Sleeps 6
Palm Villas at Mauna Lani F23 | Beach Club Access | Sleeps 6 | Mountain ViewsPalm Villas at Mauna Lani F23 is a spacious 2-bedroom + loft, 2-bath condo located within the prestigious Mauna Lani Resort on the Kohala Coast of the Big Island. Sleeping up to six guests,...
4th Fl Marine Surf Studio | Prime Location | Parking
Stay in comfort in the heart of Waikiki, only a short stroll to the International Market Place, restaurants, shops, and the island’s vibrant nightlife. This central location is unbeatable—and your unit includes one free parking stall, a rare bonus in Waikiki!🏠 The...
Island Surf 308 – Newly Updated with Ocean Views
Island Surf 308 – Newly Updated with Ocean ViewsExtend your escape with our special offer:Book 5 nights at any of these breathtaking properties and enjoy the 6th night free!Stay a Little Longer—On Us!Enjoy a complimentary late check-out and savor every last moment of...
Maui Resort Rentals: 6BR Retreat at Luana Garden Villas, Private Villas Only Steps from the Beach!
Nestled within the highly desirable Enclave Three of the Luana Garden Villas, this upscale 6BR haven combines two 3BR villas from two neighboring buildings to create over 4000 sq ft of interior living space, perfectly suited for larger groups or families. Located on 38...
At Ocean's Edge w/Lanai, WiFi, Cable TV-#202
Savor tropical fruits on the lanai with ocean views that define paradise. This casual 570 sq. ft. condo is a dream for active travelers who love relaxing at the day’s end with a sunset dinner at home. Comforts include cable TV, clock/radio, and ceiling fans. Sleeps 4 in...
Gorgeous private home with spectacular ocean views & private pool at Kohala Ranch
Gorgeous home with spectacular views and extra privacy on 6 acres in the Kohala Ranch community. This newly upgraded dream home is perfect for couples and families looking for a spacious three bedroom home where they can relax and enjoy panoramic ocean and mountain...
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
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.Ranch Beach Estate is a hidden Hawaiian gem,...
Cozy 1-bedroom + loft in Ocean Front Complex, 2 Lanai's and WiFi in Kailua-Kona.
Unwind in Kailua-Kona at this Ocean Front complex 3rd floor Kona Makai Condo 5-306 on Alii Drive. Bedroom with a king bed and loft with a queen bed, guests can enjoy a comfortable stay. The bathroom is supplied with body wash, shampoo and conditioner and a hair dryer...
Perfect for Romantic Retreat! Spacious Oceanfront Suite w/ Pool Access
Step into paradise: Explore Kanaha Beach Park & indulge at Queen Kaahumanu Center, right from our welcoming Kahului Bay doorstep.This listing is for a room within a hotel.✦ Your room is 588 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV,...
Walking Distance from Papaloa Beach, Outdoor Pool, Free Parking, Full Kitchen!
Welcome to your ultimate tropical retreat! Walk to Waipouli Beach & Coconut Marketplace, with Opaekaa Falls just a drive away. Perfect for island exploration!This listing is for a room within a hotel.✦ Your room is 725 sq. ft, equipped with complimentary toiletries,...
Spacious Kona Retreat | Sleeps 17 | Game Room
Gather everyone — without feeling crowdedThis expansive Kona retreat is designed for large families and multi-generational groups who want space, comfort, and effortless island living. Comfortably sleeping 17 with five king bedrooms, a dedicated bunk room for kids, a...
Waikoloa Hawaii 3 Bedroom Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This three-bedroom, three-bath condo sleeps 6 and boasts lanai views of the ocean and the 9th hole of The Village Course. The primary suite offers golf course views, a king bed, a TV, and...
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Welcome to Kailua Beachfront Estate, an exceptional 7-bedroom, 6.5-bath sanctuary that sleeps up to 14 guests on O'ahu’s most exclusive stretch of sand. Blending timeless coastal architecture with luxurious modern amenities, this 5,902-square-foot residence offers the...
Makaha Valley - Few Mins away to Beach
Relax at this cozy and luxurious 4 bedroom, 2.5 bath brand new house in a 24-hour gated community.Take in the fresh air and the lush mountain view from the tropical themed bedrooms and lounge on the Italian leather sofa after a whole day exploring in the sun; enjoy your...
Kiahuna Plantation Resort 161 Ocean View 1 Bedroom
Gaze out at the Pacific from this 2nd floor ocean view condo, just steps from Kauai’s most iconic beach. A perfect blend of comfort and scenery, ideal for couples or small groups. Unit 161 Ocean View 1 Bedroom 1 Bath• Fully equipped kitchen includes full size...
Terrific 2-bedroom condo in Kapaʻa
Aloha and welcome to Paradise. We feature a boutique resort with an old Hawaii feel right in the middle of all the action. We are a 2 bedrooms, 1 and 1/2 bath duplex townhome, sleeping 6. Featuring a King bed in the upstairs master with a balcony to see the ocean, a...
REDECORATED! Like-New Oceanview 4 Bedroom 3.5 Bath Lux Montage Kapalua Grand Residence Sleeps 8!
New Offering! 5201 recently joined Private Paradise Villas our newest "Your Own Private Paradise". An extensive redecoration was just completed as of late 2025. We are thrilled to welcome our first guests to this FULLY redecorated (all new!) villa boasting expansive...
Niu Beach Estate – Private Luxury Meets Island Sophistication
Welcome to Niu Beach Estate, a breathtaking 5-bedroom, 5.5-bath modern plantation retreat set along the peaceful southern shores of Oʻahu. Spanning an expansive 7,711 sq ft of indoor–outdoor living, this newly remodeled estate blends contemporary coastal luxury with...
Kihei Estates G105 Gorgeous Remodeled Condo Home
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean, restaurants, and shops of Maui all within a couple minutes walk from this 1 bedroom 1 bath island oasis unit in the heart of Kihei. Wander right out to the well maintained grounds and...
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that make...
Oceanfront Villa on Kona Coast with breathtaking views
Your home away from home in the Mauna Lani Beach Resort with 5 bedrooms, 7 beds and 9 bathrooms. This villa offers guests a relaxing retreat with an outdoor oasis with 2 pools, 2 spas, and modern amenities like WiFi, a fitness room, and AC. The 9 bathrooms ensure...
Luxury suite overlooking Waikiki skyline with Ocean View, FREE Parking!
Allure Waikiki #2702 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches throughout features...
Kolea 8E - 3 Bedroom Ocean View Vacation Rental
Kolea 8E is a three bedroom, three and a half bath villa with a sweeping view of Hualalai and an impeccable ocean view of Anaeho’omalu Bay. It is one of the few front row villas that also overlook the private Kolea Beach Club, where Kolea guests are invited to enjoy the...
Kapalua Ridge Villa 1222 Ocean View 1 Bedroom
Nestled on a gentle slope, this Ridge Villa boasts beautiful ocean views and a calm atmosphere. Located within Kapalua Resort, it’s perfect for those looking to unwind in style.Ridge Villas #1222 1 Bedroom Ocean View• The Ridge Villas are perched high above the ocean...
Spacious 5-bedroom house with WiFi, fitness room in enchanting Keaau
Discover the beauty of Keaau from this 5-bedroom house. With 1 king bed, 2 queen beds, 1 child bed, and 1 crib, this terrific property offers plenty of space for guests. Enjoy the convenience of a washing machine and dryer, WiFi, fitness room, heating, AC, and more....
Fairways South 23 Four Bedroom
Located within the desirable South Fairways at the prestigious Mauna Kea Resort, this charming 4-bedroom home is adorned with exquisite Asia-Pacific decor. This beautiful vacation rental not only offers breathtaking ocean views but also provides a serene oasis to unwind...
Unwind in Style: Newly Remodeled Pacific Monarch with Spectacular Ocean Views!
Welcome to your new home away from home!Step into paradise with our beautifully remodeled Honeymoon Luxury Suite on the 25th-floor studio, offering mesmerizing east-facing views of the ocean that defy description. Nestled in the heart of historic Waikiki within the...
Always a Great Idea To Unwind! 2 Comfortable Units, Outdoor Pool, Oceanfront!
When it comes to comfort, convenience, and an aloha spirit - you found the right place to stay. Relax by the pool, indulge in our buffet dinner, and enjoy views out over Kahului Bay. All this is yours within 10 minutes of the airport, and you'll be close to many of the...
Incredibly roomy, adjacent to the best beaches/Wailea
Extremely roomy, high-end 1-bedroom 2-bathroom, deluxe 1039 square feet condo at the gateway to Wailea. Remodled and features a king bed, high-end furnishings, and a sofa bed. The property has two pools, two hot tubs, two tennis courts and lush gardens. Home boasts...
2-bedroom, 2.5-bath Townhome Puamana Basecamp, Surf, Pools & Family Chill
Puamana Basecamp is your laid-back home for true West Maui living. Located inside the private, oceanfront community of Puamana, this 2-bedroom, 2.5-bath townhome offers beach access, a nearby beginner-friendly point break, and multiple community pools—including one set...
Ko'Olina Hawai'i - Oahu - Ocean Front Resort - by Marriott - 2 Bd. Mountain View
In the Luxury community of Ko'Olina, on Oahu's west side, sits Marriott's Ko'Olina Beach Club. This oceanfront resort has all the amenities you expect from a world-class, luxury Marriott Resort. On-site is a spa, a health club, restaurants, bars, a sundry shop, multiple...
The Ideal Property for a Digital Nomad in Hawaii. Enjoy Paradise.
Minimum Stay: 30 daysMaximum Occupancy: 1 guestWelcome to my beautiful Honolulu home, located in one of America’s premier destinations. Just a few miles from Waikiki, this residence sits atop a hill in a secure, gated community and offers sweeping ocean views, cooling...
Aqua Aloha Surf Waikiki 1505 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1505 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, 365 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...