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.
Sugar Beach Resort - #131 - Sanitized - Oceanfront - Ground Floor - Walk Out
Sanitized with Quaternary Ammonium for COVID-19Hawaii Tax # TA/GE: 096 120 6272-01Lawn, sand, and ocean only 15 yards away at your fingertips at Sugar Beach Resort. Ground floor, oceanfront walk-out, unit #131, newly renovated. Convenient covered parking in the MILL...
Luxury + Privacy • Sleeps 8 • Beach Club Access
Summary:Kulalani in the Mauna Lani Resort • 68-1118 North Kaniku Drive #503 • NEW to the Rental Market!Kulalani 503 is a luxurious townhome located in the highly desirable Mauna Lani Resort. Boasting a lavish master suite featuring a spacious tile shower and...
*Maalaea Kai 104* NEW LISTING Maui Stunning Prime Ocean Front !
Enjoy this ground floor unit featuring gorgeous views throughout the unit of Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. The unit is tastefully decorated with the spirit of Aloha and has a portable a/c unit in the living room and...
Hale Ka Pua Ola – Private Luxury Retreat in Kukui'ula
Welcome to Hale Ka Pua Ola at Kukui'ulaHale Ka Pua Ola is a luxurious 4-bedroom, 4.5-bathroom retreat nestled within the prestigious Kukui'ula community in Koloa, Hawaii. Surrounded by lush tropical landscaping and breathtaking views of the Pacific Ocean, this elegant...
Stunning Ocean View Beach Front Villa at Kahaluu
Enjoy this resort quality 2 bed 2 bath Penthouse condo with exceptional ocean views across the street from Kona's famous Kahalu'u Beach. Relax in the sand, learn to surf, snorkel with the turtles and tropical fish. All this is just steps away from your door.- Beautiful...
Gorgeous remodeled condo Oceanfront! SUNSET! <br>
Elegance on a budget! This quiet third floor end unit has spectacular ocean views from throughout the condo. Our air-conditioned condo overlooks the beautifully manicured grounds with unobstructed ocean views. The kitchen has concrete countertops and top-end appliances....
KAANAPALI COTTAGEn 2 bedroom cottage within walking distance of Kaanapali Beach
International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10...
Ola'a House by Volcano Heritage Cottages in Village center-1 mile to Nat'l Park
Ola'a (meaning "lively" in Hawaiian) House is a 1,700 square foot home in the heart of Volcano Village featuring authentic Hawaiian furnishings and original art by local artists. The house is owned by the co-founder of Kilauea Lodge and former Magnum PI make-up artist...
Pristine 3br Ocean and Mountain View Home in Kukuiula
Tropical elegance with a modern touch and ocean and mountain views are what make Kukuiula Vacation Rental #39 a prime vacation rental. Located in the exclusive Kukuiula community in Poipu, this two-story vacation rental sleeps up to eight people with three bedrooms and...
Stunning Oceanfront 1 bedroom 2 bath condominium, Kaanapali Beach, Maui
Contact us at 206 484 3766Amazing oceanfront 1 bedroom, 2 full bath condo. Located in tower 1, 4th floor, unit #407, at The Whaler Resort on a beach often voted "one of the worlds most beautiful".We are on the south "sunny" side of tower #1. Our home is one unit back...
Makaha Ocean Lullaby... The famous Makaha surf beach!
Remodeled fourth floor unit in Makaha's ONLY Beachfront Condo! The other condos you will find are located about 2 miles to the South. Our studio has been completely remodeled, and is located on the cool side of the building, with Ocean and Sandy beach views. We look...
The Crown Jewel of Kawela Bay! 30 day stay
Hale Keo Keo – Historic Beachfront Home on Kawela Bay, Oahu’s North ShoreWelcome to Hale Keo Keo, the only home built directly on the sand in Kawela Bay — a calm, crescent-shaped cove on Oahu’s iconic North Shore. With room for up to 17 guests, this rare...
ROMANTIC AMBIANCE OF 'OLD HAWAII'. GROUND FLOOR, CLEAN, BEACH GEAR INCLUDED
Aloha, and Welcome to Maui Kaanapali Villas. Our villa is located on the best beach on Maui! Snorkeling right out front, restaurant on premises and a day spa. 2 pools and jacuzzi's. One pool located only steps from the condo lanai, it is the smaller of the two and more...
Newly remodeled 1bd with contemporary finishes
Discover the ultimate island retreat at Kamaole Beach Royale #208—a 1-bedroom, 1-bathroom oasis perfectly situated within walking distance to both the beach and Kihei's vibrant shopping centers. This unit comfortably sleeps up to 4 guests. Renovated in 2022, this...
Cottage #1
Hale Makai Cottage 1 offers a stylish, modern retreat in the enchanting Haena area on Kauai's North Shore. This cottage features a comfortable king-size bed, a fully equipped kitchen, and a private deck where you can relax and enjoy the sunshine and ocean views. As part...
Ocean front Beach Resort Hale Nalu ~ ~
Aloha ~Step inside and experience the sophisticated charm of a newly renovated space, featuring a state-of-the-art kitchen equipped with modern appliances and sleek finishes, perfect for crafting island-inspired meals. The studio boasts a sumptuous king bed for a...
Spacious lanai-Maui Vista Relax/Work/Play in this lush tropical getaway!
Perfect location! Newly remodeled 1 bedroom/1 bathroom corner unit that sleeps 4. Ideally located with ocean and mountain views. Stay in style with everything you need for work and play. Start your day with a walk on Charley Young beach-literally across the street,...
Posh, beachfront gingerbread home with 3 lanais- walk to parks, dining, tennis
Oceanfront Kalakaua Surf & SunsetsOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located directly on spectacular Tonggs Beach, this posh 3BR/2.5BA home looks fresh from the pages of...
Rare, three bedroom Platinum Level remodeled townhouse, featuring the most premier ocean, island and coastal views!
*Please note that the Kapalua Resort and this property were not affected by the Lahaina fires, nor were our surrounding areas or Napili, Kahana and Kā‘anapali. West Maui communities of Kā‘anapali, Nāpili, Honokōwai, and Kapalua are fully open to visitors....
Breathtaking Ocean Views from Quiet Beachfront Condo! Free Parking!
Colony Surf #1005 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)Stunning ocean and Diamond Head views! This spacious (853 sq. ft.) open floor plan suite is the perfect spot to enjoy...
Lani Oasis - Princeville Vacation Home with Saltwater Pool
On Kaua’i’s picturesque north shore, a popular destination due to its lush green cliffs and stunning sunsets, sits beautiful Lani Oasis. This four bedroom, three bath home has family-friendly features including a fenced-in salt-water pool, bunk bed room, and plenty...
Your oasis by the sea, stay at B103!
Step off your lanai, & enjoy the pristine ocean, pool, or hot tub. Snorkel with sea turtles & colorful fish. Walk to Kaanapali Beach & boardwalk for casual dining or groceries. Additional shops & restaurants minutes away at Whaler's Village & downtown Lahaina. Papakea...
Kauai Dreams - Hanalei Bay Resort 1305/1306
Hanalei Bay Resort 1305 & 6: This beautiful spacious studio with an adjoining hotel room is located on the top floor with high open-beam ceilings. It is surrounded by tropical foliage and spectacular views of Hanalei Bay and Bali Hai. On your very own private lanais,...
❤️PiH❤️OHANA Time ★Closer to KaMilo Pools ★Hilton Resort Passes
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Ohana Time, part of our Hawaiian Luxury Collection.Ohana Time at KaMilo is a wonderful 4-bedroom home in the exclusive Mauna Lani Resort.We take great pride in offering some of the most coveted homes on the...
Regency at Poipu Kai 323: Beautifully Updated Poipu Resort Condo With A/C
** Fall 2025 Special Pricing**Welcome to Regency at Poipu Kai #323, your peaceful Hawaiian home away from home. This south shore Kauai vacation rental condo boasts an ideal location in the heart of sun-drenched Poipu, with easy access to the Garden Island’s best...
REMODELED-OCEAN VIEWS FROM EVERY WINDOW-GREAT BEACH ACCESS-AC-WELL EQUIPPED
Book with confidence, this stunning, 2 bedroom, 2 bathroom (1033 sq. ft) condo that has been completely remodeled with beautiful modern finishes. The condo has ocean views from every window and great beach access as it is right across the street from Kamaole Beach 1....
Golf and Beach Paradise!
Beautiful space to relax!Mauna Lani Beach Club pass included! Beach towels, beach chairs, and toys for you!Enjoy a peaceful setting at this Mauna Lani Fairways 2 bedroom/2-bathroom, 1300 square foot townhome! The primary bedroom En-suite is located upstairs with a small...
KM 131 OceanFront Ground Floor Condo w Pool AC Beach
FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S1)*One ticket per...
Summer Special! 10% Discount With 7 Day Stay
Nestled in the heart of Waikoloa Villas, this top-floor 2 bedroom/2 bath condo offers serene views overlooking the Waikoloa Village golf course. Just a short drive away, you'll find the island's best beaches at Waikoloa Beach Resort, along with a variety of excellent...
Ocean views with Hawaiian-inspired decor
E komo mai! Come on in! Papakea J201 offers the best Papakea has to offer with its quiet shady-side location and broad ocean views. J201 is a 1-bed, 1-bath condo that accommodates 2 guests. The large windows on two sides of the living area offer sweeping views of the...
Island Living: Beachfront Penthouse Retreat at Sugar Beach PH#23
Welcome to Sugar Beach Resort #PH23– Island Living!Experience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with elevators, provide easy...
Hapuna Beach Residence B21 at Mauna Kea Resort
This magnificent, oceanfront, newly-constructed, island masterpiece offers floor-to-ceiling window walls that create indoor/outdoor living space, a sleek, gourmet kitchen with Wolf and Sub-Zero appliances, double ovens, a cappuccino machine, wine storage and...
Kona Makai 6303: Tropical Retreat 1BR w/ Ocean Views, Pool & Gym
Bask in the beauty of Kona Makai 6303, a remodeled, one-bedroom, one-bathroom oceanfront condominium. This stunning top-floor unit also features ocean views from the main spaces, free Wifi and a wonderful loft with two twin beds (trundle style). Located less just one...
Oceanview Maui Condo - Steps from Kamaole Beach!
Escape to paradise at this charming 2-bedroom, 2-bathroom condo in the highly sought-after Maui Kamaole complex in South Kihei. Located just across the street from the beautiful Kamaole Beach III, this second-floor unit offers stunning ocean views, perfect for catching...
Kauai Paradise: oceanview 2-bedroom condo with AC and private lanai
Aloha! Welcome to paradise on the amazing North Shore of Kauai.Our 2 BR/2 BA oceanview condo in Emmalani Court - Princeville, offers a comfortable haven to relax after exploring the Garden Isle. It has wonderful ocean and mountain views and a private lanai, cooled by...
Delightful condo 2-bd condo close to the beach
Island Sands 105 is a 2-bedroom, 2-bathroom ground-floor condo that offers easy access, 1 window A/C in the living room, and a private washer and dryer. This property has elevators for easy access. Unit 105 can accommodate up to 6 guests. The master bedroom offers a...
Fab Ocean View, largest 1 Bedroom Premium Villa!
Ignite your senses with warm, sunny beach days and dazzling sunsets! Ocean View, Beautiful 1 Bedroom, 1 Bath Premium largest size villa at 900 sq ft, sleeps 4. Parking included, no fees.Full Resort Access. On one of the world's most beautiful beaches!The Westin...
Makena Surf G205 - Exceptional Oceanview!
E Komo Mai to our completely renovated two bedroom ocean-view unit artfully designed with you in mind! This luxurious unit, tucked away in the coveted South Maui oceanfront property of the Makena Surf, is only steps away from the beach. So let the beauty of what makes...
Koa Resort 5i-updated 3BR, Pool, Tennis, Hot Tub, Zoned AC, Sleeps 9, pool view
Welcome to Koa Resort 5i, located across the street from the beautiful beaches of South Maui. With plenty of room for your entire family, Koa Resort 5i is a great spot to kick back and experience the Maui lifestyle. This is a 3-bedroom 2-bathroom second-story condo,...
Private Pool. Fully Air-conditioned .
This home is new on the rental market. Previously, it was reserved for our family use only. It has been completely refurbished this year. It is the perfect getaway for those that would like their private pool and is located in a peaceful subdivision close to all the...
Fairway Villas Waikoloa A21 Includes Waikoloa Gold King Golf Club Membership
Enjoy our 2 bedroom, 2 bath villa for you and your family quietly tucked away along the Big Island's sunny Kohala Coast, Fairway Villas Waikoloa offers the crisp style, gracious elegance, and modern sophistication. Villa has FREE WIFI and PARKING.VILLA UPDATE - brand...
Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops
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.Welcome to Kahala Cottage by Gather, your...
An Endless Summer 132- Poipu Beach, Kauai
Located on the most popular beach in Kauai for a reason! Sandy beach and warm ocean water with a large grassy area for lounge chairs for the best sunrise and sunset views! Be as busy or not as you wish..."An Endless Summer" unit 132 is a ground floor end unit taking...
Permitted Luxury Home, Stunning Views, Heated Pool, Perfect Location!
Luxury Home with the Best Views on the Kona Coast (Big Island of Hawaii). We have a STVR (short term vacation rental) permit issued by the County of Hawaii. You'll love our large, heated pool with travertine decking around the pool for the ultimate luxury. Cooks dream...
Maui Resort Rentals: Honua Kai Hokulani 542 - Extra Large One Bedroom w/ Den, Partial Ocean and West Maui Mountain Views!
Hokulani 542 is an expansive two-bedroom, one-bathroom suite boasting views of what West Maui is most famous for, the blue Pacific Ocean and lush West Maui Mountains. With its den converted to a second bedroom, this rare offering provides the space and privacy of an...
Maui Resort Rentals: Luana Garden Villas 16D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3 Bedroom/3 Bath residence is conveniently set within Enclave Three of the Luana Garden Villas. This premiere elevated offering is defined by its southwest-facing orientation with gorgeous views of sunrise skies and the West Maui Mountains. Its...
Gorgeous North Shore Kauai Estate with Saltwater Pool
Bright, cheerful and tastefully designed, this 5 bedroom home sleeps 10 comfortably. Each room has its own unique personality, while the estate is coordinated with aquamarine color schemes, hardwood accents and inspiring details. Cooking for many is an easy task with a...
Aloha Condos, Kanaloa at Kona, Condo 2602, Oceanfront, AC
Hawaii STVR Registration Number: STVR-19-355146 ************* Aloha and welcome to our luxury, oceanfront, island home!! This is not your “ordinary vacation rental”, but rather a completely renovated, highly upgraded home, in an amazing oceanfront location...
PAW 1706 Remodeled Wailea Condo w Pool AC Near Beach
FREE daily activities included with your stay value up to $956! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S3)*One...
STUNNING OCEANFRONT PENTHOUSE 2Bd/2Ba *Fully Renovated, Pool * Poipu Palms Koloa
This magnificent end unit Penthouse was completely remodeled with everything new just a couple years ago! The Pacific Ocean stretches out as far as you can see in front of you. You often see turtles, spinner dolphins and even whales when they are in season! Enjoy the...