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.
4BR I Kii Hale at Kukui ula Signature Retreat
Summary:Kii Hale at Kukuiula is a contemporary 4BR, 3BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites relaxation in every corner. All...
Wyndham Waikiki Marina | 2 Studio Suites
Summary:Live like a super star when you stay at this resort, which has hosted celebrities, presidents, and jetsetters. You get easy access to Waikiki Beach, the most famous stretch of sand in the Pacific. Surf’s up.Wyndham Waikiki Marina | 2 Studio SuitesEach suite...
Gorgeous Ocean View 3BR 2BA Home, Wailuku, 6 Mo. Min priced below vacation rates
This single family home is being rented out for six months while we travel. Inquiries for less than six months will not be accepted. A home of this size, quality, location, and ocean view would conservatively rent for $350 per night but we're discounting it to $289 per...
Cozy studio- 5 min away from shopping center
Come and stay in a cozy studio located in a quiet suburb of Oahu. You can walk a minute away from the community pool area where you can swim around or just lay down and relax while soaking in all of Hawaii’s sunshine. Drive for 5 minutes to one of Oahu’s popular...
Direct Oceanfront! Sugar Beach Resort, Penthouse in paradise, AC, TV, WIFI, POOL
Welcome to Sugar Beach - the longest white sand beach on Maui! This fully remodeled OCEANFRONT condominium is a Penthouse unit at Sugar Beach Resort (6 floors total) in Kihei, Maui. All new flooring, kitchen, bathroom and appliances!Our condo is one bedroom, one bath...
Maui Kaanapali Villas 110: This sprawling ground-floor condo awaits at the heart
Maui Kaanapali Villas 110: This sprawling ground-floor condo awaits at the heart of Maui Kaanapali Villas Resort. It boasts spacious rooms with high ceilings and tropical furnishings. This suite can accommodate up to six (6) people. There is a King bed in the primary...
Cozy studio in wonderful Waikiki with refreshing AC breeze
Consider this studio your home away from home while you visit Waikiki. This terrific space features one bathroom and keeps you comfortable with air conditioning. Guests will appreciate thoughtful touches like a hair dryer and iron, making packing light a breeze. Whether...
** 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...
Private Paradises, 4BR, Studio, 2 Kitchens
Welcome to Kona in a furnished main house, with an attached studio that elegantly decorated with crafted arts made by my wife, cater for large groups. An unmatched treasure, tropical vibes, 5 minutes from KOA airport:✔ Spacious Three Comfortable Bedrooms – 3 Beds + 2...
One of the absolute best values available at Honua Kai, Hokulani 634 is a full two-bedroom suite with an upgraded interior and panoramic views of the lush West Maui Mountains from its fantastic corner location.When nightfall comes, and it is time to rest and recharge...
🏖️Ocean Front | Fantastic Location - Walk To Kona Town
Ali'i Drive Oceanfront Escape – Apt 504Welcome to your Kona coastal retreat—a fifth-floor, front-row condo offering breathtaking panoramic ocean views from the heart of Kailua-Kona. Situated along iconic Ali'i Drive, this one-bedroom, two-bathroom condo invites you to...
Kapalua Bay Villa 19G2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- 1st floor villa accessible by 16 stairs from parking lot- Travertine tile floors throughout- Updated open kitchen with granite counters and stainless steel appliances – fridge with ice maker, stove/oven, microwave, dishwasher, cookware,...
** 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...
Charming studio w/ country views!
Beautifully located on half an acre with gated secure entrance. Enjoy a lanai, lots of orchids and peaceful surroundings. Situated on a hill above the street w/views to beautiful vistas, native vegetation and colorful birds. Suitable for 2-3 people.
Idyllic 90 Day North Shore Getaway!
Our hisorical Hale (ha-lei: Hawaiian word meaning home) is a plantation style paradise! Many of the homes in our neighborhood are the original houses for the Kahuku sugar plantation/mill workers. The area is rich in tradition and history. Many of the families have been...
Maui 3 Bedroom Kapalua Retreat Home
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Step through stunning custom wood-and-glass front doors and let your eyes travel straight through the home to the Pacific beyond. Inside, the open-concept living, dining, and primary...
Kuleana Club #615 Oceanfront - 1 bd&1 ba - Gated
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a 2nd floor oceanfront condo, only steps to the ocean, and surrounded by a plush Hawaiian garden. Enjoy...
Kauai Modern Luxury •Near Beach •A/C •Golf Views •WiFi •Huge Kitchen •Sleeps 12
• New Poipū luxury with central A/C• Sunrise/sunset golf views from relaxing lanai• Huge modern fully stocked kitchen + high-end appliances• High end furniture from Restoration hardware• Comfortable mattresses + extra linens if needed• Spacious dining + fast WiFi with...
Anini Vista Viila at Princeville Resort By Parrish Kauai
Perched above the turquoise waters of Anini Reef and the lush fairways of the Prince Golf Course, Anini Vista Villa is a contemporary luxury retreat in the prestigious Queen Emma’s Bluffs neighborhood of Princeville. This luxe four all bedroom suite home offers nearly...
Beach escape NorthShore 1BR Unit OceanView
NOTE: There's ongoing(as of November 2021) building construction that may cause noise and some areas closed during your stay. Working hours between 9am-2:30PM(Mon-Fri).This is a beautiful area of Oahu, which takes you away from the crowds of town yet you are close to...
Welcome to our cozy high-floor studio located on Niu Street in the heart of Waikiki.The studio features a comfortable queen-size bed, perfect for two guests. The kitchen is equipped with a burner, microwave, oven, and kettle. A small dining table with two chairs sits...
** 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...
Hawaiian King 212 Studio Suite, Full Kitchen, Pool, Sleeps 2
Welcome to Hawaiian King 212 Suite - Your Home in the Heart of Waikiki!Address: 417 Nohonani St #212, Honolulu, HI 96815Room Type: 1 bedroom Hawaiian King 212 Suite Overview: Discover your own slice of paradise in the heart of Waikiki with our Hawaiian King 212 Suite....
NEW! Tropical Hideaway by Keauhou Bay | Golf, Beaches & Views
Keauhou Palena – Kailua-Kona Vacation Rental CondoDiscover Your Perfect Hawaiian EscapeNestled between the scenic Keauhou Bay and the Kona Country Club Golf Course, Keauhou Palena is a peaceful, secluded condo village where you can park right at your own front door....
Waikoloa Hawaii 3 Bedroom House Sleeps 10
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Newer-built 3 bedroom home in the new Ainamalu development close to everything Waikoloa has to offer. Once you pass through the lava rock walls and head past the ohana (what we call a...
Makani A Kai B5 Ocean Front condo 10 yards from private beach access.
Oceanfront Escape at Makani A Kai B5 – Maalaea, MauiWelcome to your personal paradise on Maui’s southern coast! Nestled directly on the beach in Maalaea, this 2-bedroom, 2-bathroom oceanfront condo offers the ultimate island retreat. With sweeping views of the Pacific...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Amazing | 3 Units, 5 Bedrooms | HK ML-1784
** 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 2352 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Kaanapali Alii 235 is a luxurious ocean-view vacation rental located in the prestigious resort area of Kaanapali along Maui’s west coast. This spacious condominium...
Delightful, quiet, close to beach and convenience stores, 3-bed house in Keaau
Nestled in Keaau, this delightful house is a charming retreat for guests. With 3 bedrooms including a queen bed, bunk bed, and more, there's plenty of space for everyone. The 2 bathrooms are equipped with all the essentials, ensuring a comfortable stay. Plus, the...
Welcome to the serene and luxurious Mauna Lani Point B102, your perfect retreat nestled in the heart of Kamuela. This stunning 1-bedroom, 1-full bathroom, and 1-half bathroom condo offers an elegant blend of comfort and style, ideal for a romantic getaway or a peaceful...
Maui Kaanapali Villas #221: Studio garden view at a beach front resort in West M
Maui Ka’anapali Villas #221: Studio garden view condo at Beach Front Resort on N. Kaanapali BeachThe space: This condominium is located in the Aloha Tower, the central hub of the property. Situated on the second floor, this condo has views of the surrounding foliage....
Most Expensive Luxurious Oceanfront Estate on Makena Beach-6BR/7.5BA 8,030 Sq Ft
Step into island luxury at this breathtaking oceanfront estate on Makena Beach, one of Maui’s most exclusive and pristine stretches of coastline. With 8,030 square feet of elegantly designed living space, 6 spacious bedrooms, and 7.5 bathrooms, this private retreat...
Beachfront Paradise! Enjoy surf & sunsets on beautiful uncrowded beach. Relax!
"The Ultimate Hawaiian Retreat" Great monthly rental, contact owner for your dates, availability and discounts. Gorgeous gated oceanfront and beachfront home. Located on large double lot on the sunny side of Oahu. Two homes on a huge lot both with ocean views. Perfect...
Spacious Hillside Villas 1500-7 by Gather w/AC, Lanai, Pool Access & Golf Ne
Hillside Villas 1500-7 welcomes you to the relaxed elegance of Ko Olina in Kapolei. This spacious two-story villa offers three bedrooms, two and a half baths, and 1,553 square feet of thoughtfully designed living space. With peaceful garden and golf course views, it’s...
Kapalua Bay Villa 19B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- 1st floor villa with 16 stairs between parking and front door- Travertine tile floors throughout- Updated open kitchen with granite counters and all the expected appliances, including: fridge with ice maker, stove/oven, microwave,...
Luxury, Comfort and Aloha Spirit Await on the Big Island
Welcome to the ultimate Hawaiian escape at Na Hale O Keauhou, where the gentle ocean breezes, swaying palms, and stunning sunsets create the backdrop for an unforgettable vacation. This enticing two-story condo, available for vacation rental by owner (VRBO), offers the...
New Listing! Stunning Oceanfront Sunsets
Noelani #306 – Oceanfront Luxury with Unforgettable Views Experience Maui living at its finest in this beautifully remodeled 3-bedroom oceanfront condo, perfectly perched between Kāʻanapali and Kapalua. Noelani #306 offers two expansive lanais with panoramic views of...
Stunning Hawaiian Vacation: 2 Bedroom at WorldMark Kona
Spread out with the whole family in this spacious two-bedroom suite. Bed sizes may vary in bedrooms.Located in the area regarded by King Kamehameha as one of the most beautiful spots on the Big Island, this resort is an ideal destination for your island paradise...
Oceanfront Resort-Beach Access, Close to Oahu's Popular Sites
Set along Oʻahu’s tranquil western shoreline, this spacious two-bedroom ocean-view villa at Marriott’s Ko Olina Beach Club offers relaxed island living with beautiful views of the Pacific. Ideal for families or friends traveling together, the villa features a primary...
Kaanapali Alii 4442 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Welcome to Kaanapali Alii 444, your beachfront playground at Maui’s exclusive Kaanapali Alii Resort. With sweeping views of the Pacific Ocean, swaying palms, and...
New Listing! Charming Condo Steps to the Beach
Welcome to Maui Parkshore 209, a bright and inviting 2-bedroom, 2-bathroom condo that comfortably accommodates up to six guests. This South Maui retreat is thoughtfully designed for relaxation, convenience, and unforgettable island living. Located directly across the...
Royal Kahana 1103: Cozy studio in Lahaina with ocean views and premium amenities.
Royal Kahana 1103 Spectacular Ocean Views from this 11th floor West Maui Studio, Watch Whales from the private Lanai or Lounge at the Oceanfront Pool Welcome to Your Maui Retreat: Wake up to sweeping views of the Pacific and the vibrant reef below at this beautifully...
Escape the bustle of Waikiki and access some of the North Shore’s best beaches! You’ll be in proximity to Ahupuaʻa ʻO Kahana State Park, Turtle Bay, the Maʻakua Ridge Trail and World Famous Banzai Pipeline where you can catch a wave or watch pro surfers in action. The...
Honeyed Jade: 8 BD Ultra Luxury Oceanfront Diamond Head Estate with Pool & Hot Tub
Honeyed Jade is an enchanting Diamond Head vacation rental estate located on the exquisite island of Oahu. Oahu is an ideal island to visit if you envision yourself amid beautiful Pacific blue waters and within easy access to shopping and first-class restaurants....
Sea Glass: Luxurious 3BR in Princeville w/ Lanais, Pool Access & Mountain Views
Nestled in the exclusive gated community of Villas of Kamali‘i in Princeville, Kauai, Sea Glass by Gather is a serene, fully renovated three-bedroom, three-bath luxury townhome offering 1,825 square feet of modern comfort and mountain-view tranquility. Designed for six...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Studio Value Price | 3 Units, 5 Bedrooms | HK ML-1321
** 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 Shores 213 2BD North Kaanapali Resort Condo Overlooking Pool, Palms & Courtyard
Kaanapali Shores 213 Beautifully Updated 2nd Floor North Kaanapali Condo Overlooking Swaying Palm Trees and the PoolWelcome to your Maui Retreat: Kaanapali Shores 213 is a freshly remodeled 2-bedroom, 2-bath condo located in the vibrant beachfront community of North...
Royal Kahana Maui 519 Ocean View Studio
Step into this airy studio featuring sweeping ocean views and easy beach access. Perfect for couples or friends wanting a relaxing stay. Unit 519 Ocean View Studio• 5th floor studio with balcony • Studio kitchen includes microwave, stovetop/oven, coffee maker,...
** 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...
Newly Remodeled, Fully Furnished 1-BDRM with Ocean View - Discovery Bay, Waikiki
Discovery Bay Endeavor Tower1778 Ala Moana BlvdFreshly remodeled and fully furnished 1-bedroom condominium with ocean views and one covered parking space. Enjoy ocean vistas from the bedroom, living room and private balcony. This unit is located in Discovery Bay...