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.
Just Listed! Top Notch Rental Experience Awaits!
Experience breathtaking sunsets every evening from your private lanai and immerse yourself in the fresh ocean air at Kaleialoha 213. This West Maui vacation condo is perched right on the water's edge, offering unparalleled proximity to the ocean. The property boasts a...
Views on the Kaanapali Coast!
Prepare to be completely swept away by the breathtaking beauty and boundless excitement that awaits you on the island of Maui, your best vacation yet! At the beachfront retreat of Paki Maui, the azure waters of the Pacific Ocean gently caress the golden sands just steps...
Hale O Ka La – Luxury Villa at Mauna Kea Resort
MEET THE VILLAHale 'O Ka La on the Big Island defines Hawaiian luxury. Developed by Laurance S. Rockefeller in the 1960s, Mauna Kea Resort was the Kohala Coast's first luxury destination and remains an icon of island elegance.This stunning 5,358 sq. ft. estate features...
Kapalua Ridge Villa 124 Gold Ocean View 1 Bedroom
- Villa is closest to Oneloa Beach- Second floor unit with 15 stairs from parking to the villa- Tile flooring in kitchen, bathroom and carpeted in living room and bedroom- Fully equipped kitchen with stainless steel appliances includes stovetop/oven, microwave, and...
Golf Discount in Village, Gorgeous Views, 2 Pools
Welcome to your Waikoloa retreat - a peaceful condo surrounded by tropical beauty & golf course views, perfect for relaxation after beach days or island adventures:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Private lanai w/ sunset & fairway views- Shared pools, hot...
Gorgeous 5 br for 12 in Kapaa - Beachfront!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!The fabulous 5 bedroom, 4 bath oceanfront for 13, is made up of a 3 bedroom and 2 bedroom oceanfront townhome, just steps apart! Fabulous beachfront pool and sundeck onsite! Beautiful...
Wailea Ekolu 1608 | 1 Bedroom, 2 Bath | Prime Wailea Location with Golf Course V
Experience the beauty and convenience of Wailea from this tastefully appointed 1-bedroom, 2-bath condo at Wailea Ekolu 1608. Perfectly situated along the fairway of Wailea’s prestigious Blue Golf Course, this ground-level home offers comfort, privacy, and stunning...
Luxurious 2-bedroom/2-bathroom oceanfront condo with pool, jacuzzi and parking
Escape to this oceanfront condo on Oahu’s North Shore. This spacious end-unit features 2 bedrooms, 2 bathrooms, and comfortably sleeps 4+ with 3 beds. Enjoy breathtaking ocean views from large bay windows or relax with the soothing sound of waves. The condo includes...
Kona Studio + 2 Small Bonus Rooms, Big Covered Patio, Near Beaches /Airport
Newly renovated (June 2025)! Bright studio with Queen bed plus Full & Twin in bonus sleep rooms (76” ceilings). Perfect for families—kids get their own space at a fraction of hotel costs. Enjoy cool breezes at 1,070 ft elevation, a covered patio, and private...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanfront Gem, Over 3400 combined Sq. Ft. w/ Built-in Viking B.B.Q.
This 5-bedroom gem combines one of our very finest 3BR oceanfront "Ali'i" residences with a spacious partial ocean view 2BR suite located directly next door and is perfectly suited to larger groups or families.The generous 3400+ sq ft of the combined interior living...
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just a bike ride away from the world famous Kailua and Lanikai Beaches. With stunning views of the Ko'olau Mountains and the...
Kapalua Golf Villas Gold Fairway View 2 Bedroom
Golf Villas Gold Fairway View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and bathroom- Guest bedroom with 2...
Kaanapali Alii | 124
Kaanapali Alii 124 is an exquisite two-bedroom ocean-view rental that is perfect for families or groups seeking a luxurious getaway in Maui. This spacious residence features an open floor plan that seamlessly connects the living, dining, and kitchen areas, creating a...
New Listing! Save up to 25% Instantly on stays thru 5/31/25! 2B/2B, AC, Pool
Experience tranquil island living at Kaanapali Plantation 12, nestled on 10 acres of lush tropical gardens. This serene and spacious retreat is just minutes from the renowned Kaanapali Beach. This charming 2-bedroom, 2-bath condo is a haven for golf enthusiasts,...
Charming 2-bedroom apartment on beautiful farm in Honaunau with WiFi
Honaunau Farm Wellness Retreat is a 7-acre organic, regenerative farm with sweeping views of Kealakekua Bay & lush tropical surroundings.The Ohana house has a full kitchen, living room, & covered patio with access to our retreat area with infrared sauna, outdoor shower,...
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Kick back and relax in this calm, stylish beach getaway. This recently updated apartment features a living space with an ocean view from the balcony. Bright and airy, you’ll enjoy ocean breezes and fall asleep to the sound of waves. Have your pick from the gorgeous...
Ko Olina Kai 1083C: Contemporary 3BR, Private Lanai, Walk to Beach & Dining
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 Ko Olina Kai 1083C by Gather, a...
Serene Mountain Views from 6th Floor Studio at Lahaina Shores
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE! Lahaina Shores 610 – West Maui Mountain ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 610 is a 6th-floor...
Charming 4-bedroom cottage with WiFi and AC in serene Laie
Consider this cottage your home away from home while you visit Laie. This delightful property boasts 4 bedrooms including a king bed, 2 bunk beds, a queen bed, and a futon. With 4 bathrooms equipped with showers, your group will have plenty of space to freshen up. The...
Cozy studio in Ka Eo Kai, Kauai, HI
About this spaceOverlooking Anini Bay, this cozy studio suite is the perfect place to be while on the island of Kauai. Lots of amenities to enjoy. The resort offers easy access to top Kauai shopping, dining, entertainment, state parks, national wildlife refuges,...
Maui Resort Rentals: Honua Kai - 5 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought after two-bedroom "penthouse" suites with three neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
LS 215 Direct Beachfront Views Remodeled Studio
Lahaina Shores 215 NEW LISTING Amazing West Maui Sunsets Every Night from your Private Lanai! Steps to the Beach and Pool FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Oceanfront Kona By the Sea 2-Bedroom Retreat with Central A/C
45-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside...
Pineapple Paradise - Natural rock tidal pool
**30-day rental. Please inquire.Welcome to Pineapple Paradise! This 2 bedroom, 2 bath oceanfront home has breathtaking ocean views along with a natural rock tidal pool, a unique feature for enjoying the water as the tide comes in. This is a perfect getaway paradise for...
🌺 Support LOCAL: NEW! Mākaha Valley Home With Large Studio And Amazing Backyard
🌺 Mahalo (thank you) for choosing to support LOCAL! 🤙🏻We are brand NEW! We know you have many options available to you in this neighborhood from big corporations and companies but we promise that you will be pleased with your decision. 😊SUPER family friendly...
New Listing Specials! Walk to Beach. Sleeps 6. Fantastic Resort Amenities.
Centrally located in Kihei and a three minute walk to Kamaole Beach, where you'll have access to some of the area's best snorkeling, whale watching, and sunsets. Short drive to coveted Wailea beach!★ Ocean View★ Private bedroom and bathroom★ Two full bathrooms★...
Relaxing Kalakauan 1-Bedroom | Private Lanai
This family-friendly vacation home is tucked away at the beginning of the Waikiki strip and features secured entry. This 1-bedroom, 1-bathroom offers easy access to the Waikiki Strip, Hilton Hawaiian Village, Fort DeRussy Beach Park, world-famous Waikiki Beach, Hawaii...
1 Bedroom Oceanfront W/Lanai-Kahana Reef #216
Kahana Reef #216: Grab your phone for selfies on your private lanai that has a backdrop of spectacular ocean views! Enjoy captivating sunsets nightly and during the winter, watch whales play in the distance. Lounge at palm-tree-top levels on the lanai. Here you can...
Stunning Beachfront Condo, Sans Souci, Kitchen, WiFi, Smart TV & Free Parking
Unwind in Honolulu at this cool condo. This excellent property is on the beach & features a cozy living space with a Queen murphy bed plus sofa bed, perfect for relaxing after a day of exploring. The well lit bathroom includes a bathtub / Shower combo, hair dryer &...
4 Units Perfect for Groups! Outdoor Pool, Close to the Beach!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Tropical Garden Tranquility HNL
From kid-friendly splash pads and playgrounds to calming koi ponds, a private pool, meandering paths and shaded bbq and dining areas, this outdoor oasis offers endless outdoor spaces. This serene home-away-from-home offers two private bedrooms, full bath, full kitchen,...
Island Escape: 2BR Villa at Wyndham Kona Hawaiian Resort
Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort offers the perfect combination of relaxation, adventure, and Hawaiian...
Amazing Remodeled 2 Bdrm w/ AC! - Menehune Shores #509
Menehune Shores #509 – Ocean View Comfort in North KiheiEnjoy ocean views and the comfort of home at Menehune Shores #509, a two-bedroom, two-bathroom condo designed for relaxation and convenience. Perfect for couples or small families, this North Kihei retreat offers...
Hale Lu'u Kini Ea B-310 Stunning Ocean Front Villa
Hale Lu'u Kini Ea - Your Perfect Hawaiian RetreatWelcome to Hale Lu'u Kini Ea, a spacious 2-bedroom, 2-bathroom villa located in the tranquil Beach Villas at Ko Olina. This villa offers breathtaking ocean views from every bedroom, allowing you to wake up to the serene...
Escape to Paradise! Townhome in Coconut Plantation, just minutes from lagoons!
Welcome to the wonderful resort area of Ko Olina! Located within the gated community of Coconut Plantation, this gorgeous townhome offers guests the perfect blend of comfort and convenience, the ideal island getaway. Features of the townhome include: Prime Location:...
HGVC Hokulani Waikiki Luxury, 1 BR Suites, Rooftop Pool/Spa, Close to Ft Derussy
Anchoring the northernmost stretch of the celebrated Waikiki Beach Walk® entertainment district, Hokulani Waikiki, a Hilton Grand Vacations Club offers ideal access to Waikiki’s most vibrant showcase for dining, shopping and entertainment. Just a brief walk from the...
Maui Resort Rentals: Honua Kai Hokulani 1029 - 2BR Deluxe Oceanview Grand Penthouse, BBQ on Balcony + Jaw-Dropping Ocean Views!
We are proud to present this jaw-dropping 10th-floor deluxe oceanview grand penthouse at the Honua Kai Resort—newly launched on 3/4/25 to start taking bookings beginning May 7, 2025!Unquestionably one of the finest residences on offer at Honua Kai, this stunning...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
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.Discover the epitome of island elegance at Ko...
1 BR Suite City View, w/ AC, WiFi and Kitchen - Bamboo Waikīkī Hotel #504
Castle Bamboo Waikīkī Hotel #504 - The living area is furnished with a and a desk/workspace for all those business travelers. Enjoy watching the Flat screen TV while sitting on the new couch, which doubles as a fold-out sofa bed to accommodate additional travelers....
"BEAUTIFUL LUXURY CONDO WITH GORGEOUS VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA"
"MODERN LUXURY CONDO WITH BEAUTIFUL VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA""WELCOME TO SKY ALA MOANA" Luxury condominium built in 2023 conveniently located in Ala Moana. Enjoy beautiful views of city, mountain and sparking ocean. 1br/1ba /1assigned parking with Full...
Kihei 2 Bedroom Condo Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Located in South Maui, nestled within five acres of lush tropical landscaping. This low-density complex features amenities such as a large swimming pool, hot tub, tennis and pickleball...
NEW! Spacious 3BR Home in Old Wailuku Town | Central to All of Maui
*Reduced Introductory Rates and discount for stays 7 nights or more. Excludes Dec 20-Jan 5*Modern Comfort in Old Wailuku Town – 3BR Ground Floor of DuplexStay where Maui locals live, in the historic Wailuku Town—an authentic small town with coffee shops, galleries,...
Marriott Maui Ocean Club | Three 3BR/3BA Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ocean-MT Views From the Luxury Sky Ala Moana Condo with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to the luxurious building scene in Honolulu. Consisting of two...
Paradise Resort Home in Ko Olina - TCP-1220-3
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Manele Bay, Lanai Hawaii Ocean Facing Home
Spacious home on the island of Lanai. Footsteps from Four Seasons at Manele Bay Hotel and Hulopoe Beach. All the comforts of home in an island paradise. Two bedrooms, each with king-sized beds, and two and one half baths, including an outdoor shower. Ocean view and...
Steps Away from the Beach! 3 Premium Units, Private Lanai, Onsite Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
2 Bedroom Mountain Garden at Marriott's Maui Ocean Club - Lahaina & Napili Tower
Spread out with the whole family in this spacious two-bedroom suite. This is as classic as a Maui oceanfront resorts get. Tropical greenery, koi ponds, palm trees, and Pina Coladas around every corner. Really, this place is situated perfectly on Ka’anapali Beach,...
Oceanfront balcony, 40 ft to ocean, 2 bed, 2 bath, remodeled! 3/8-3/15/2025!
This is Hono Koa, a timeshare resort located in Honokowai, 1 mile to Ka'anapali Beach resorts, and 3 miles to Kapalua. It's an easy 1-mile walk to the Times Market grocery store. We own only the KOA oceanfront units. They are bigger and nicer than the other units. The...