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.
Keauhou Surf and Racquet 8202 | 2 Bed, 2 Bath
This peaceful condo offers a comfortable stay on the second floor of a quiet, gated complex with access to a shared pool and tennis court and just a short drive down scenic Ali‘i Drive from some of the area’s best beach spots. Magic Sands Beach (also known as...
The PERFECT Vacation Condo, close to beaches, shopping, discounted golf
We are located in the gated complex of Vista Waikoloa on the fourth green of the Waikoloa beach golf course. The course is a twenty seven hole layout, kings nine, lakes nine and beach nine. One of the advantages of renting this unit is the discount on golf. As a guest...
Your Perfect Hilo Homebase - Sleeps 9 with AC
ALOHA! Welcome to your Perfect Hilo Home Base! We have two sweet, spacious Plantation Style Homes on the same lot -- this listing is for the Larger House in the Back. This 3 Bedroom 2 Bath House with outdoor deck can sleep 9 guests and is all yours. Comes with A/C, W/D...
Superb location at Māla Nani at Kamaole Sands! Steps to Beach! Ground Floor. A/C
Aloha!Welcome to Kamaole Sands, one of Kihei's most sought-after resorts! Māla Nani at Kamaole Sands is our TOP ''A'' RATED, garden view home in the HIGHLY DESIRED BUILDING #7. Our inviting ground floor unit is ideal for couples and families, especially those with...
Luana Waikiki Premium Studio- Gym & Pool
Enjoy staying at our beautiful studio at Luana Waikiki! From the private lanai you can enjoy the ever-changing City views of Waikiki, Fort DeRussy Park, and through the palms trees even catch a glimpse of the ocean. Room features premium upgrades including upscale wood...
Villa Lava at Mauna Lani Resort w/ Keyless Entry and Private Beach Club Access!
ALOHA! Immerse yourself in an authentic Big Island vacation experience while staying at our beautiful Tommy Bahama inspired ‘Villa Lava’, located in the private gated luxury community of the Fairways at the Mauna Lani Resort on the majestic Kohala Coast. The Mauna...
Chic and Central Ocean Dream Vista
Summary:Upscale remodel with high-end furnishings 1br oasis situated directly across from Kameole Beach. Fantastic lanai with direct ocean views. Experience the resorts many amenities such as tennis courts, pool and jacuzzi and grills. We provide everything from beach...
Premium One bedroom Suite or Premium Studio on Beautiful Ka'anapali Beach
Beautiful Premium One Bedroom Suite is 750 sq. ft. with a king size bed in a separate bedroom, a sleeper sofa in the living area, a full size kitchen and dining table and a large bathroom with double sinks, walk in shower and jacuzzi tub .In room amenities include DVD...
Kona Reef Sand and Surf (beachfront/walk to town)
Awe inspiring views and once-in-a-lifetime experiences await you from our newly renovated, ocean/beachfront (direct ocean access) Kona Reef Condo. 2 BR/2BA (sleeps 4-6).Kona Reef is a highly desired resort for it's walking proximity to Kona town, location right on the...
Wailea Oasis: Relax in Your Spacious Villa w/ Lush Tropical Views, Private Lanai
Grand Champions is perfectly situated in Wailea, in spectacular South Maui. World-class beaches, golf, restaurants, and two swimming pools await your visit. Two master suites with king-size beds plus one queen-size sleeper sofa, air conditioning throughout, tastefully...
Dreamy condo near the ocean with pool, hot tub, lanai, fast WiFi & beach toys
Hali'i Kai 8EOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' When it comes to experiencing the Big Island in style, look no further than this fantastic condo perched in the highly...
COMPLETELY REMODELED-WELL EQUIPPED-NEW FURNITURE-INNER COURT-LARGE LANAI-AC
Book with confidence, this newly remodeled (October 2025) 2 bedroom, 2 bathroom (1188 sq. ft) condo. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7....
Pili Mai 06L By Parrish Kauai
Nestled among a championship golf course, Pili Mai is set in an ideal location on the island of Kauai’s south shore in Poipu Beach. This is Kauai's newest resort development and has a choice of two, three, and four bedroom luxury condominiums.This central Poipu...
Maui Parkshore 416: two bedroom condo with stunning view of the ocean.
Maui Parkshore 416: two bedroom condo with stunning view of the ocean.Stunning, unobstructed ocean views from this two bedroom corner condo. The bright and open living area opens to a large lanai, extending the living area. The primary bedroom has a king bed and the...
8 Person Minivan to Rent!, Hilton Pass, Family Friendly, 3bedroom, M4
This pristine 3 bedroom, 3 bathroom home has 1,725 square feet in 2 stories with expansive outdoor spaces and backs up to Hole 3 of the prestigious Waikoloa Beach Resort Golf Course. This unit is fully stocked- including toys for littles!Master Bedroom: enjoy serenity...
Royal Sea Cliff Family Resort, 2 OV Pools, Large Lanai, workspace, Ali'i Drive!
Enjoy the Big Island in a lush, oceanfront setting. The Wyndham Royal Sea Cliff is conveniently located a mile and a half from the charming town of Kailua-Kona. Enjoy nearby restaurant dining, or shop at the local farmer’s markets and make yourself at home in your...
3BD Ka'ulu Villa (129B) at Hualalai Resort
Important Resort Notices• September 15 – Mid-November, 2025: The Hualalai Spa will undergo enhancements to its outdoor aqua-thermal areas. Massage and body treatments will temporarily relocate to the Makaloa Villa. Guests will continue to have access to the infrared...
2.7 Acres of Exceptional, Secluded Retreat - Close to Beach & Shopping!
Nestled on the slopes of Hualalai, the Keauhou Hideaway is a private retreat on 2.7 acres of lush tropical vegetation. The 800' elevation affords a spectacular view of the Kona coastline and ensures warm, sunny days and cool nights. Renovated last in 2012, the Hideaway...
Maui Kamaole I217 2brm/2bath Executive Vacation Home
6th night free! discounts applied when booked. offer good until Dec 15th, 2025.Treat yourself to luxury on a Budget in a custom furnished Wailea-quality executive vacation home in a quiet complex across the street from Kamaole III beach in South Kihei/North Wailea,...
IMPECCABLY REMODELED GROUND FLOOR OCEANFRONT - 50' FROM THE SEA TURTLE SANCUARY!
“IMMACULATE"...."AMAZING"....."REFRESHING"...."SO CLOSE TO THE TURTLE SANCTUARY!".....are some of the descriptors from our Guest Reviews.... Located directly on beautiful Maalaea Bay, savor stunning sunrises over majestic Haleakala every morning in this newly...
Modern Waikiki Beach Oasis w/ free parking
Aloha! This 550 sq ft 11th floor 1 bedroom in Waikiki Banyan is a relaxed, contemporary space designed to create special memories in a stylish, comfortable environment. With a city and mountain view from the lanai, this fully updated, air conditioned property is just...
Rainforest Stay w/ Hot Tub < 3 Mi to Nat'l Park!
From exploring active volcanoes to strolling black sand beaches, this modern 1-bed, 1-bath Volcano home is your base for an unforgettable island adventure. The eco-conscious hosted vacation rental is tucked away in the tranquility of the rainforest, yet only 3 miles...
Wailea Ekahi Village 12C - 1 Bedroom Ocea View Condo
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers a perfect blend of comfort and tropical elegance, making it an ideal retreat for those looking to escape the hustle and...
Ocean, Marina, and Pool View 2BD Corner Unit w/ AC at the Ilikai Hotel
Experience the beauty of Waikiki with Happy Vacations, a short-term vacation rental company! Our team is excited to offer you a modern condo at the renowned Ilikai. Amazing views of the sunset with the sun gleaming over the ocean. During the day, you can embrace views...
Panoramic Ocean View Condo on Golf Course close to Beaches
Our townhouse in the Wailea Ekolu Place located on the Wailea Blue Golf Course. It has a spectacular view and large lanais to enjoy a panoramic views and Maui sunsets. It has 2 bedrooms, 2 full + 1 half bath townhouse. Our master bedroom has a king sized bed and ensuite...
Pineapple House: Ocean View Home in Keauhou Estates w/ Private Hot Tub, BBQ & AC
This elegant 3-bedroom, 2-bath home in the gated Keauhou Estates blends spacious island living with serene privacy. Set on the ground level with tropical gardens, city views, and a glimpse of the Pacific, it offers a refined retreat just minutes from downtown...
Studio condo #165 at the Kona Bali Kai in Kailua-Kona w/Ocean View
This phenomenal condo at the Kona Bali Kai in Kailua-Kona is a true gem for guests looking for a soothing retreat. With a cozy living room featuring a luxurious queen sized bed and a twin sofa sleeper, this amazing property offers a private oasis for relaxation. The...
Hale Kamaole #124 Ground floor condo, easy access to best beach on Maui!
Experience Maui from this ground floor one bedroom unit, steps away from two pools, the tennis court, and close to grills with easy parking! The furniture has been renewed for comfort. Bathroom cabinets updated with both tub & shower. Bedroom has king bed with an...
Great location for exploring Hawaii.
Unobstructed ocean and coastline views.3 bedroom and 2 bath plantation style home.2 cal king and twin set nova form mattresses.All new appliances,utensils,furniture,linens,washer,dryer,BBQ,50 inch TV. Direct TV, WiFi. Ceiling fans throughout. Deck railing bar-top...
2 Bedroom Oceanview - Steps to the Pool and Ocean
FABULOUS LOCATION - Just 50 steps to the pool, the hot tub and the BBQ’s and a few more steps to the ocean-front lounge chairs. Grab a cool drink and head out to watch the sun set between Molokai and Lanai. Bring your binoculars for excellent whale watching December...
Sea La Vie Secluded Oceanfront condo, Magical Sunrise romantic honeymoon Getaway
It is not just a dream! You really can have it all here “ 50 Shades of blue! Come relax and enjoy yourself in our UNIQUE, beautiful and extremely cozy ocean-front oasis, just steps away from the aqua blue ocean.Our contemporary, beautifully remodeled 975sf condo was...
Indoor-Outdoor living for three
Beautiful Indoor-Outdoor living for three at our peaceful stream side retreat with private gazebo. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place to recharge and rejuvenate. Hear the rush of our waterfall and enjoy our...
Dlx Oceanview Waikiki1Br Condo...Stunning Ocean/Marina Views!
Welcome to your own 1br Oceanview Condo in Waikiki...ideally located on the Marina side of Waikiki...near the famous Hilton Hawaiian Village.. Enjoy great ocean & marina views from the privacy of your own lanai from your Waikiki beach vacation condo rental ...just...
Ocean-view condo near beach & dining, beach chairs & gear provided
Kapa'a CaptivationOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Promotional rate of $169 a night until the end of 2025! Make the most out of your time in Hawaii at this Kapa'a...
Comfortable loft condo with private lanai, resort pool, hot tub, tennis courts!
Maui Kamaole K205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the beauty of Maui from this immaculate 2-bedroom, 2-bathroom condo at Maui Kamaole in Kihei, Hawaii....
Spectacular Wall of Glass!
Never have you stayed in a condo such as this. There is a wall of glass so you have a panoramic view of the ocean and beyond!Maui has been consistently ranked as the 'Best-Hawaiian Island' and '#1 Island Destination' by the readers of Travel & Leisure or Conde Nast for...
Gorgeous Oceanfront Condo in South Maui * Royal Mauian *
Fully remodeled and updated, our home is ideally suited for a romantic getaway, celebrating a special life milestone, those looking for a little laid-back downtime, and anyone wanting to enjoy Maui to its fullest potential. Our 1 bedroom 1 bath oceanfront condo is in...
Wai'ula'ula Condo at Mauna Kea - Luxury Vacation Rental
Welcome to Wai‘ula‘ula at Mauna Kea---a private, gated community on the Hapuna Golf Course. Relax in our 3-bedroom, 3-bathroom, 2,100 sqft. condominium and enjoy the many upgrades we’ve added to our home, including hardwood floors, new bedroom carpeting, an...
Hale Keani O-1203 stunning Views to relax
Welcome to Penthouse Hale Keani O-1203 at the Beach Villas at Ko Olina – Your Luxury Hawaiian EscapeIndulge in the splendor of our breathtaking two-bedroom, two-bath penthouse, located on the twelfth floor of the Ocean Tower at the prestigious Beach Villas at Ko...
Maui Westside Presents: Honua kai - Konea 312/314 3 bedroom/2 Bath sleeps 10
This is a unique listing for booking two individual condos under one booking. You'll be renting Konea 312 and Konea 314 side by side, creating a three-bedroom, two-bathroom combination that can sleep up to ten guests!Konea 314 is a luxuriously renovated one-bedroom...
Beach Front Ocean View Penthouse Kealia Resort Condo - Sugar Beach
Aloha and welcome to your oceanfront getaway at Kealia Resort!This beautifully updated, fully air-conditioned 1-bedroom condo offers stunning views of the ocean, West Maui mountains and tropical gardens, and is just steps from the beach and the oceanfront pool. Bright,...
Kaanapali Alii | 4106
Welcome to Kaanapali Alii 4106, a luxurious two-bedroom vacation rental that offers an unparalleled ocean view from its prime corner location. This stunning condo is designed for relaxation and enjoyment, with breathtaking vistas of the blue Pacific visible throughout...
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...
Watermark Waikiki Unit 901: Luxe Condo w/ Pool, Resort Amenities & Oceanviews
Step into refined island living at Watermark Waikiki Unit 901, a spacious two-bedroom, two-bathroom corner residence in Honolulu’s iconic resort district. From the ninth floor, your lanai frames sweeping views of the ocean, marina, city, mountains, and fiery...
Newly Renovated Condo - Next to the beach!
This 1 bedroom unit is equipped with everything needed for an unforgettable vacation experience. Enjoy the ocean views and sunsets while relaxing and sipping on a glass of wine from the balcony/lanai. The condo is perfect for couples looking to take a break and enjoy...
Manualoha 303 - Ground Floor with Free Poipu Beach Athletic Club Membership
MANUALOHA 303 AT KOLOA KAI VACATION RENTALSTropical Garden Retreat Near Poipu BeachEscape to paradise at Manualoha 303, a beautifully upgraded 1-bedroom, 1-bathroom garden-view condo that combines comfort, convenience, and the lush beauty of Kauai. Located just 0.2...
Maui Resort Rentals: Honua Kai Hokulani 413 - 4th Floor Interior Courtyard 1BR w/ Gorgeous Ocean Views!
Maui Resort Rentals is proud to bring you this premier one-bedroom villa at the Honua Kai Resort, newly launched on February 20, 2025, to start taking bookings on April 7, 2025!Located in the only 1BR column of interior courtyard facing suites at the entire Honua Kai...
Big Island Luxury - 3000+ SqFt. 4 Bed 4 Bath. Beach Close. Hawaiian Paradise.
Our Newly Renovated Estate Home in the quiet neighborhood of Hakalau invites our guest to relax and enjoy paradise in luxury. Spacious and open floor plan offers plenty of room to accommodate large groups and gatherings. Air conditioned living spaces and bedrooms. Free...
YOUR OWN LUXURY PRIVATE RESORT WITHIN A RESORT AT SEAGLASS 810 AT ANDAZ MAUI
Tucked within one of Wailea's most exclusive beachfront communities, SeaGlass Villa 810 at Andaz Maui Wailea Resort is a privately-owned and independently-managed 3 bedroom 4 bath pool-side ultra-luxury residence available for your next vacation dream. Experience "Your...
Plantation Style Studio & Courtyard Garden In Koloa
COUNTY APPROVED PERMIT # Z-IV-2015- 25TMK # 2-6-013-046-0000Come and Experience Kauai's Sunny South Shore & Beautiful Beaches. Towering Eucalyptus Trees Form the Famous Arch Known as the " Tunnel of Trees " as it Welcomes our Visitors and Marks the Official Entrance...