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.
Custom cottage feels bright & airy yet cozy and private in this country setting.
Cottage Cottage feels open and airy with high open beam ceilings in the living room and kitchen. Lots of windows let the trade winds in. Chill upstairs on the catwalk in a comfy recliner or outside on one of the 2 decks or on the relaxing dbl hammock outside. Short Walk...
Honu Kai Villas 2 by Destination Kauai - A/C, Ocean Views, Stunning Sunsets
E Komo Mai, Welcome to Honu Kai Villas IIJust steps from the Pacific coastline, this multi-level updated villa boasts beautiful ocean views and stunning sunsets on Kauai's south shore. Morning strolls to watch the sea turtles and spinner dolphins are a must! Snorkel at...
Amazing Ocean View 4 bedroom/4.5 baths with AC!
The newly renovated, air-conditioned four-bedroom private house offers all the best of Princeville in Kauai.Sit on the lanai and breath in the fresh Kauai air and take in the beautiful Ocean view. Whale watching in season. If you look closely, you may see dolphins going...
Gorgeous Kiahuna unit - fully remodeled Fall 2022!!
Open, airy and perfect location. You will feel like you're in the jungle with the floor to ceiling cathedral windows in the open living and dining room/kitchen. End unit with no one above or below you! Two floors with living and eating space upstairs and bedrooms on...
Westin Kaanapali Ocean Resort - Luxury 2 Bedroom Villas
Perched on twenty-six lush acres with breathtaking views of the Pacific Ocean and the islands of Lana'i and Moloka'i, Westin Kaanapali Ocean Resort Villas (commonly referred to as WKORV) provides the ultimate in pampering and relaxation. Enjoy an afternoon unwinding...
Kolea 6E ~ Oceanview Three Bedroom Kolea Villa
Along with ample living space, Kolea 6E offers a nice ocean view of A'Bay over one of the few vacant lots remaining at Kolea. This villa is great for families as well as those just looking for a peaceful getaway in Hawaii.As you enter the villa you will be astonished at...
Stunning NEW Remodel-Sunsets-Luxury-Quiet Location-Ac-Large Lanai
Book with confidence, this stunning, 1 bedroom, 2 bathroom (1022 sq. ft) condo that has been completely remodeled from top to bottom with modern finishes, where even the lanai sliding doors were replaced. This condo is managed by PMI Maui, a local Real Estate Brokerage...
Paradise at Bay View Farms w/ Private Infinity Pool, Hot Tub & Incredible Views
Bay View Farms Estate HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Retreat to a gentler, slower-paced era in this beautifully decorated “Estate Home”, offering 6400 sq. ft....
Wailea Elua 1101 - Beachfront Section - Ocean View -1 Bedroom &NewQualitySofaBed
We are a 1 minute walk from the amazing Ulua Beach. You can see and hear the ocean from our condo. Relax viewing the ocean on a private, quiet lanai surrounded by tropical gardens. Earth-friendly furnishings and complete “green” remodel. Gourmet kitchen, spacious...
Romance on top of the ocean-Amazing View-Large Lanai comfy daybed-Cold AC
Book Honu Hideaway today and fall in LOVE with this piece of PARADISE! You won't be sorry when you step into this one-of-a-kind, unique vacation rental sitting only 10 feet from the water's edge! 210 Welcomes you with so much ALOHA....Some of the many owner-supplied...
Romantic & Breathtaking Oceanfront Kauai Condo
240+ 5 Star ***** "Wonderful" "Amazing" "Stunning" Reviews and Counting! Please plan ahead as our instant booking calendar fills up quickly.THE AMBIENCEIf thoughts of azure oceans, romantic getaways and sunrise mornings are just some of the peaceful images that makes...
Lae Nani 433. New renovation. Fabulous Ocean View from this Top Floor Condo. A/C in Bedroom!
Summary:Fabulous ocean view from this top floor condo and plenty of space for everyone. Bedroom has air conditioning!The Space:This top floor (3rd) condo has one of the best views on the island. From your living/dining area and lanai you can view Wailua Bay and even...
Anahola Beach Hale - Tropical Beachfront Home with AC
This quintessential tropical beachfront home with 4 bedrooms and 4 baths with air conditioning throughout is surrounded by lush tropical foliage and swaying palm trees is located on one of Kauai's most beautiful beaches. The expansive stretch of white sandy beach...
Villages at the Mauna Lani Resort 🌺 Walk to Mauna Lani Restaurants & Shops
Welcome to the Villages at the Mauna Lani Resort!"Originally the ancestral beach front home of Hawaiian royalty, the 3,200-acre Mauna Lani Resort now offers an exquisite blend of sophisticated luxury and Hawaiian-style hospitality. Mauna Lani Resort is just 25 minutes...
Stunning Ocean View! Kapalua Bay Villa 12G4! Quam Properties Hawaii
Kapalua Bay Villa 12G4 is a beautifully remodeled and spacious 1-bedroom, 1-bathroom ocean view condo, just a short walk to the beautiful beaches located in Kapalua. This condo features amenities such as a large private lanai, free high-speed wireless internet, and...
The Pool House: 6 BR Kailua Home with Pool, Walking Distance to Kailua and Lanikai
The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's Steakhouse. The home offers a...
Spacious 2BR Poipu Retreat w/ AC, Lanais & Resort Amenities
E Komo Mai — Welcome to Mala Pua Regency 610!Discover your perfect island retreat in this beautifully appointed 2-bedroom, 2-bath ground-floor condo located in the heart of sunny Poipu. Designed for comfort and relaxation, the open-concept living space features two...
Maui Resort Rentals: Luana Garden Villas 10A – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3BR/3BA residence is conveniently set within Enclave Two of the Luana Garden Villas. Villa 10A's west-facing orientation offers an open view between the Hokulani and Konea Towers, and its designation within our "Grounded" collection at the Luana Garden...
🏖️Top Floor | Mountain, Lake & Golf Course Views! | Concierge Included
vrKCV - Waikoloa Beach Villas N32, Professionally Managed by Kona Coast VacationsWelcome to Your Waikoloa Paradise!Location, location, location! Nestled in the heart of Waikoloa Beach Resort, this top-floor villa offers unparalleled access to some of the best spots in...
'The Aloha Green House' Retreat w/ Ocean Views!
The ultimate Hawaii getaway awaits at this 2-bedroom, 1-bathroom vacation rental apartment with sweeping views of the Pacific. Ideally located between Kona and Hilo, this home-away-from-home provides easy access to popular areas such as Hawai'i Volcanoes National Park...
Hale Kupa'a: Charming Island Villa w/ Beach Nearby
Hale Kupa'a—this delightfully situated house on Poipu Kai’s scenic, super-convenient Green Belt walkway—was completely remodeled in summer 2021, and the exquisite attention to detail is evident in every light, bright, charming room. Leafy green views fill the windows,...
2 Private Homes for 1! Pool & Waterslide - Cove Hale
Extend your escape with our special offer: Book 5 nights and enjoy the 6th night free! Use promo code: 6THFREEBlackout dates: November 22–30, 2025 and December 20, 2025 – April 20, 2026Cannot be combined with other promotions or discounts. Located just 0.2 miles from...
Surf Cove - Ocean - Jeep
Welcome to Maui! Stay in this stylishly updated, fully furnished vacation condo in the heart of Kihei. The ground-level unit lanai/patio is conveniently located steps away from the resort-style pool and outdoor barbecue area. The interior consists of top-of-the-line...
Wailea Ekahi 10C - Close to Main Pool & Beach! Spacious condo -Sleeps Up to Four
Our home is in the 1st (and closest) phase of Ekahi and is just steps away from the main pool pavilion, the beach, and a second pool even closer. Ekahi is a huge complex, so check the complex maps we included before booking. Some units are in another zip code!You have...
Absolute Oceanfront on Ancient Lava Cliffs! Whales, dolphins, turtles!
Swap the daily grind for luxurious absolute oceanfront tranquility with an escape to Paradise Breeze Retreat in Keaau, Hawaii. Only a 25 minute drive from Hilo Airport but a world away from stress. Stunning panoramic oceanfront views from every room and the audible...
NP B28 March price drop! 1BR gorgeous, private spot, full AC, well stocked
Whether your idea of the perfect Hawaii vacation includes snorkeling, surfing, golfing, paddle boarding, hiking, or just relaxing on the covered lanai, by the ocean or by the pool with a good book, Napili Point condo B-28 is your perfect home base. Our luxurious and...
Secluded Ocean View Sleeps 14 EASTER PRICING Book 10 nights for the price of 7
Looking for the perfect tropical retreat? MAUI TURTLE COVE is your ideal vacation home! Enjoy Maui in a beautiful 5 bedroom home with mature tropical landscaping and beautiful ocean views, including breathtaking Molokai Island! Just a short 3-minute walk down a private...
Ocean View Condo | Pono Kai Resort | PF-G102
Pono Kai's pool and spa will be closed January 6-31, 2026 for the installation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Experience the beauty of Kauai in this charming 1 bedroom, 1 bathroom...
RENOVATED 10/21! Corner Oceanview Condo w/ AC!!
Our recently remodeled 1 bed, 1 bath home is located on the second floor, so you’ll enjoy more privacy in your home-away-from-home. Being in the corner also gives us breath-taking views of the Pacific Ocean. During whale season, you’ll also see whales breaching from the...
OCEAN VIEW STUNNER, SNORKEL w/ TURTLES, PRIVATE COVE
EPIC OCEAN VIEWS, close to restaurants and dining, family-friendly activities, public transport, and nightlife. You’ll love our place because of the neighborhood, comfy bed, coziness, views and the kitchen. Our home is good for couples or families.“Honokeana Cove has a...
❤️PiH❤️ Pineapple Hale ★ Elegant Private ★ Bikes ★Free Hilton Pool & Waterslide Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Pineapple Hale at KaMilo is a wonderful 4 bedroom home, part of our Hawaiian Luxury Collection.Pineapple Hale at KaMilo, with updated furnishings (2024) and decor provides a perfect setting for your Hawaii...
Villa Olina Charming 3-Bedroom Villa On the Golf Course Steps Away from Lagoons
Beautiful & spacious yet cozy and comfy Ko Olina Kai Welcome to your tropical haven in the coveted Ko Olina Kai community. This delightful 3-bedroom, 3-bathroom house rental offers a prime location just a 10-minute walk from the stunning Ko Olina Lagoons. Tailored for...
Kuhio Shores designer 2br oceanfront condo w/ AC
This beautiful 2 bedroom and 2 bathroom condo has been fully updated and sits directly on the ocean. You will not find a better view and location in Kauai.All beach amenities such as towels, chairs, and boogie boards are provided.3 AC UnitsFully remodeled bathroomsTV’s...
5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.
LOCATION LOCATION LOCATION!!! 3bed/3bath This tropical retreat home in the heart of Kona sits on a half acre lot surrounded by palm trees, lush green lawns and tropical flowers with gorgeous ocean and sunset views. This parcel has unobstructed ocean views and sits in...
Third floor condo with ocean views, pool and hot tub access, and golf nearby
Shores at Waikoloa 333Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find yourself living the best life at this stunning, ocean, mountain, and fairway view condo in the heart of the...
Kona By The Sea 323 - Exceptional Kona Sunsets
Unit 323 is the perfect vacation rental for those seeking a longer stay. With its super-fast Wi-Fi, it's an ideal choice for remote workers, providing a stunning backdrop of the Kona Coast for their work-from-home endeavors. Recently upgraded, Unit 323 boasts brand-new...
Kiahuna Plantation #198 - The Best Beachfront Condominium on Kauai
There is not a Four Seasons Resort on Kauai, so we decided to make our own. Kiahuna Plantation #198 is one of the very few beachfront condominiums available on the island and is the ideal vacation destination for a couple or a family looking for an ultra-rare, relaxing...
Luxurious, Free Parking & WiFi, Ocean View, Remodeled, 1 BR Condo, No Resort Fee
Be ready to elevate your senses to a higher ground. This sustainable space is designed to harmonize your inner energies with modern yet soothing style to bring you heightened sense of relaxation and joy. Professionally designed and remodeled in October 2021, our condo...
Pili Mai 5D - Luxury 3bed/3bath, Sunny side
Make yourself at home in this luxury three bedroom, three bathroom condo located on Kauai’s sunny south side! A generously open-floor plan allows for abundant natural lighting and air flow throughout the entire home.The spacious living room features comfortable...
One Bedroom Ocean view Deluxe Luana Kai D105
D105 with AC is a gorgeous, 1 bedroom, 1 bathroom, ground floor, ocean view condo with a king size bed. It is located on the ground floor with a direct ocean view over the grassy park area and pickleball courts. The pickleball and tennis courts are located in front...
One Bedroom Oceanview Deluxe Luana Kai A202
Aloha!Welcome to Luana Kai Resort Unit A202. As you walk into the unit you are drawn to the direct unobstructed panoramic views of the ocean where the beach is just a very short walk away, across from the greenbelt of the Waipuilani Park without having to cross any...
Serene Luxury Golf & Tennis Villa - outdoor pools, hot tub, bbq
Wailea Grand Champions Villas are the perfect place for vacation. Set amid Wailea’s Blue Golf Course and adjoining Wailea Tennis Club, this property is ideal to rest from everything Maui has to offer for your discovery. Within minutes of both driving and walking,...
The Makai Manor - Beautiful Newly Built Spacious Home
This newly constructed home made it's grand debut August 2021. We are pleased to invite you to this stunning property. The home is located next to a beach park and has gorgeous ocean views. The neighborhood is quiet and extremely family friendly. Everything you will...
2Bed/1Bath Upstairs Home, 1mile to Beach, Next to State Forest, Custom Finishes
There is a black sand beach nearby to explore (Kehena), and a lava tube hidden in a kipuka surrounded by a lava field, and geothermally heated ponds, forest trails, farmers’ markets, yoga classes, chocolate and mushroom farms, dances, waterfalls, drum circles and maybe...
130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of...
Aqua Aloha Surf Waikiki 402 Superior Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 402 Superior Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) King bed, Sleeps 2, 335 Sq Ft.Aqua Aloha Surf Waikiki offers a range of accommodations that are perfect for couples and solo travelers. On-site...
Beach Chic Condo with Huge Ocean Views, Walkable to Beach, Shops & Dining
Address for this Condo: 2385 S. Kihei Rd #403, Kihei HI 96753 Condo Name: Kamaole Beach Royale***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to Kamaole Beach Royale #403, located in the heart of Kihei, Maui!. Enjoy a spectacular views of the...
Aloha Chic Penthouse Vistas
Summary:Bright, modern, and spacious. Completely remodeled in September 2021. Thoughtfully designed to elevate your Maui experience. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in sunny Kihei, all...
2 Bed Sleep 6 with Pool, A/C close to Poipu Beach with Discounted Golf Included!
***Discounted golf included with your stay!*** The sparkling new Pili Mai Resort is an open-skied sanctuary within the popular town of Poipu. Rolling hills of golf course greens surround the estate, while the entrancing Ha’upu Mountains sail into the distant sky. With...
122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai
Important Resort Notices* Each December, Hualalai Resort holds its annual Chairman’s Club event. This event will result in temporary modifications to guest access at select resort amenities. Access is managed entirely by Hualalai Resort and may change at their...