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.
Volcano Places Laukapu Forest Cottage
Laukapu Forest Cottage (LFC) is a spacious studio, vacation-rental cottage handcrafted as a "Work of Heart".LFC has a well-equipped kitchen, with refrigerator/freezer, electric range/oven, microhood, toaster, coffee and tea making supplies. LFC has a private bathroom,...
Privately-owned 1 bdrm/2 bath suite in Imperial Resort Waikiki. Enjoy amenities & beach.
Experience resort living in privately-owned suite at Imperial Resort, in Waikiki core on Beach Walk. We are steps to beach, shopping and dining.This 1 bdrm, 2 bath suite is well equipped for comfort, with the essentials of home and luxuries of a resort.Enjoy roof top...
Kuuipo Hale - Plantation-Style Beach House on Weke Road in Hanalei - Short Walk to the Beach & A/C!
Kuuipo Hale is the Sweetheart of Hanalei! This 3 bedroom/2 bath plantation style home is a super cute, beach house located right in Hanalei - a super short walk to the beach and just a few blocks to town. Bedding configuration is: 1 King, 1 Queen + 2 Twins so can...
Spring Special! Live Inspired! Live Kapalua Beautiful Villa! – No Resort Fees
Step into luxury island living at this beautifully upgraded one-level, two-bedroom Golf Villa in the heart of Kapalua Resort. From the moment you walk through the door, pride of ownership is evident in every detail. This corner location villa offers privacy,...
Kapalua Bay Villas With Stunning Elevated Views 1 BD/2BA
MAUI IS CALLING AND YOU MUST GO Your Tropical Paradise Found Kapalua Bay Villa 31-B2 Inhale the delightful island air and feel the relaxation begin KAPALUA - “ARMS EMBRACING THE SEA” Maui - The ‘Valley isle” Voted #1 vacation destination *A Vacationer’s Dream *Pristine...
Trev's Surfside Hideaway- Kihei Maui
Our Kihei Maui condo offers all the comforts of home in a peaceful garden style setting. Located just steps from the beautiful Kamaole 1 beach park and close to all amenities including some of Hawaii’s finest golf and shopping. Whether walking or driving everything you...
MAKAI SUNSETS, Waikoloa Vista A202, LUXURY CONDO ⭐️⭐️⭐️⭐️⭐️ 58+ 5 STAR REVIEWS
MAKAI SUNSETS-A LUXURIOUS OCEAN VIEW CONDO CLOSE TO THE BEACH AT VISTA WAIKOLOA - THE ENTIRE CONDO HAS BEEN COMPLETELY RENOVATED AND UP TO DATE! THIS 2ND FLOOR CONDO IS IN ONE OF THE BEST LOCATIONS ON THE ISLAND! WALK 8 MINUTES TO A BEAUTIFUL WHITE SAND BEACH! OVER 1400...
A 5-Star Estate, Large Groups, Luxury Living
This luxury condo is situated a short walk from the beauty of the beach! A 3,700 square foot, 3 bedroom, 3.5 bath gem, it is the ideal place for a quiet retreat. Features a Master Suite with private lanai and two additional bedrooms with en suite baths, sleeping up to a...
Only Steps to Ulua Beach and the main Wailea Ekahi Pool/Pavilion -1 Bd+2Ba
If this vacation home is available, you'll want to reserve it. Wailea Rentals presents: Wailea Ekahi Village 8E - Ekahi means #1 in Hawaiian and that is exactly what Ekahi Village is - 1 of Wailea's top luxury beachfront condominium resorts. Treat yourself to new! New...
Marriott Maui Ocean Club 1BR 2 bath Available week of 12/22-29
Please push ask owner a question with your dates before using the book it now button. Web site calendar does not match what Marriott shows as available or take into account that Marriott timeshares have to be booked as full weeks and check in can only start on Friday,...
Ocean Front/Beach Front Condo in Beautiful Makaha
Discover the breathtaking oceanfront condo with one bedroom in Makaha. Let the mesmerizing vistas and soothing waves of the Pacific Ocean enchant you. Imagine waking up to the gentle lapping of waves and the warm Hawaiian sun, then stepping out onto your private balcony...
Enjoy the splendor of this Luxury 2 story townhome, at the exclusive Residences of Laule'a located within the world class Mauna Lani Resort.This Luxury residence is designed for comfort and serenity. The main level of this property offers a spacious Great Room that...
Luxury Beachfront Condo with Amazing 180° Ocean Views!! Corner Unit.
Kana'i A Nalu 317 by KNOWLES MAUI• Recent full-condo remodel, new everything• Third-floor corner unit with unobstructed ocean and outer island views• Freshwater beachside swimming pool • On Sugar Beach – the longest beach in Maui, great for swimming, snorkeling,...
Waikiki Banyan 1BR Corner Unit, Gorgeous Mountain/DiamondHead view, free parking
Aloha and welcome to "Waikiki Banyan Rental", our vacation rental condo at the Waikiki Banyan.The Waikiki Banyan is one of Waikiki's most popular resort condominiums for vacation rentals, located one block from the beach in the heart of Waikiki.View our video tour at...
Outstanding Direct Oceanfront Suite #301 at The Whaler Maui
(NOTICE: WE DO NOT ADVERTISE ON CRAIGSLIST DUE TO THE HIGH NUMBER OF SCAMS)The Whaler is a premier oceanfront resort situated in the heart of world famous Kaanapali Beach, adjacent to Whaler's Village, for convenient upscale shopping and dining.Suite #301 is an...
🏖️AC | Captivating Sunsets | Magnificent Ocean View | Private Pool |vrKCV
vrKCV - Keauhou Estates Hale Ohana lea 11, Professionally Managed by Kona Coast VacationsStart Your Hawaiian Adventure at Hale Ohana Le'aImmerse yourself in the beauty and tranquility of Hale Ohana Le'a (House of Family Joy), a custom-designed Hawaiian retreat located...
Gorgeous Wailea Elua 1 Bd+2Ba Executive Vacation Condominium - #2011
2011 Wailea Elua Village - One of the very best in accommodations that the Wailea Elua Village has to offer. Immaculate, contemporary and beautiful - a state-of-the-art 1 Bedroom + 2 Bathroom vacation condominium that can accommodate up to 4 guests with an expansive...
99 Steps to the Sand - Ground Floor 3 Bedroom - Hokulani 104
This condo is zoned hotel and is in legal compliance with all Maui County ordinancesGround-Floor Oceanfront Suite and Wraparound Lanai at Honua KaiE komo mai (welcome) to Kai Hele Ku ("The Quickest Way to the Ocean"), where the warm embrace of Maui's kai (sea) and the...
Ohana Kamalani: Lavish Fairwayfront Home w/Pool, AC & Stunning Sunsets!
Ohana Kamalani is a spacious and inviting North Shore retreat set along the Makai Golf Course in Princeville. With 2,534 square feet of interior space, Bali Hai and partial ocean views, a private courtyard pool, and three king suites with ensuite bathrooms, this...
The Bluffs 22 – The Beach House Opulent Oceanview Luxe Estate
Nestled on over an acre within the prestigious Bluffs enclave on the Kohala Coast, Mauna Kea Resort Bluffs 22 – The Beach House is an oceanview estate where curated design, effortless luxury, and authentic island living flow together in perfect balance. With 8,141...
Lanikai Cottage: Charming Tropical Oasis with Private Pool
Just steps from the turquoise shoreline of Lanikai Beach, Lanikai Cottage by Gather is a beach-chic 3-bedroom, 2-bath retreat with two separate dwellings on one property and a brand-new private pool. Ideal for families or couples traveling together, this island holiday...
Walk to Ocean from house- close to BYU-H & Polynesian Cultural Cntr 3 bed 2 bath
Enjoy a slower pace in our family-friendly home, conveniently located only eight houses from the ocean in a local neighborhood close to Laie. We invite you to relax in our comfortable beds and huge cozy couch, or recline on the lanai chaise while reading a classic. When...
JUST REMODELED Spacious & Exceptional Value! Tropical Garden & Ocean View!
We invite you to enjoy days of fun & discovery on Maui in our bright, spacious, attractively decorated, comfortable, fully-equipped condo. Easy tropical living for all.Enjoy exceptional value with affordable rates, ocean view in the distance, a larger floor plan &...
Rare Single Level 2 Bedroom-Spectacular Ocean Views-Ac-Meticulous Cleaning
Book with confidence, this beautiful over sized, 2 bedroom, 2 bathroom condo that has stunning ocean views. 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...
Stunning Ocean Views! Plan your Summertime getaway today!
If you're looking for the perfect place to spend your next (or first!) Hawaiian vacation, then you need look no further!Considered to be one of the best locations in the ONLY oceanfront condominium community in Mauna Lani, you quickly appreciate the view before you; as...
Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year
Aloha and welcome to our home at The Palms at Wailea. The ocean view will take your breath away the minute you step inside. But it's the condo renovation and our commitment to our guests that will keep you coming back.Our remodeled unit has beautiful floors, plenty of...
Hanalei Bay Villas #17 - a 3br/2.5 ba ocean view condominium in Princeville
Hanalei Bay Villas #17 is a beautifully remodeled stand-alone condominium. This luxurious bungalow already had panoramic views of Hanalei Bay and the Hanalei Mountains and the interior reflects the beauty of its surroundings. Beautiful travertine tile floors, smooth...
Breathtaking View on Beautiful Sandy Beach Oceanfront
This Oceanfront Condo has an amazing view. It has a gorgeous Great Room and a beautiful fully equipped kitchen. With the roar of the ocean just a few yards away, you will not want to leave the Lanai after relaxing on the Tropitone furniture.This Condo has a beautiful...
Modern Luxury 2bed 2bath with Ocean Views and Easy Parking
Great care was taken in creating this comfortable, practical, and modern luxury home with ocean views from every room. Materials, colors and features uncommon in a rental were thoughtfully combined to create a unique, calm environment for relaxing. This is living well...
Last minute special 180 from 7/1/24-7/31/24! Come and enjoy Aloooooohaa!!
Yes you can afford this great vacation in our wonderful condo, located near Wailea . We are in the Hale Kamaole resort and are on the ground floor.Features include:Nice quiet split system air conditioner throughout the condo.1. Walking distance to Kamaole Beach 3 (it's...
Ekahi 38-A Luxury and Grace Located in Sunny South Maui
The Quiet Luxury and Attention to Detail Will Give You the Sense That You Have Arrived Home. Our Unit is Air-conditioned With a Master Bedroom / Bath Suite That Includes a New Serta King Mattresss With 1000 Count Prima Linens, Fluffy Bath Towls for the Bath and a...
Gorgeous Oceanfront H101 Condo-Best Location at Resort!
If you are looking for the absolute best location at Waipouli Beach Resort in Kauai...look no further. This one-of-a-kind ground level beachfront/oceanfront vacation condo is the most sought after property at Waipouli Beach resort! Step off the private lanai of Unit...
Beautiful Princeville Plantation Condo 3bd/3ba, AC,pool
RAINBOWS & TROPICAL BREEZESAloha! Welcome to our condo at the Plantation in Princeville, on the beautiful Garden Island of Kauai. Come and enjoy Rainbows, Sunsets and Tropical Breezes. Our Hale faces East which allows for the wonderful tradewinds to blow through, and...
Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
This is an absolute Oceanfront Villa. Watch the dolphins while you have breakfast.This wonderful Villa offers oceanfront amenities including the fragrance of the ocean spray and warm tropical breezes truly distinctive to Hawaii!Welcome to this two bedroom, two and...
OCEANFRONT BR/1BA with BREATHTAKING VIEWS! Paradise Found!
WATCH WHALES JUMP OUT OF THE WATER FROM OUR PRIVATE LANAI. Whale Season Dec-Apr. Located on beautiful Kahana Beach, our remarkable property offers captivating views of Molokai and Lanai. Immerse yourself in the perfect harmony of tranquility and convenience, with...
Spectacular Ocean View, Privacy, Sunsets & Whales from Lanai, Konea Tower #544
Spectacular OCEAN VIEW from our 5TH FLOOR KONEA extra large one bedroom one bath home #544 on the much preferred quiet and shady north side of the KONEA tower. Wake each morning to stunning ocean views from your king-size bed and spacious lanai. Floor to ceiling 'nana'...
Modern Luxury 2nd-Floor 2Bd/2Ba Retreat with Ultra-Quiet A/C, & 6'x5' Shower
About Grand Champions Villas 128 (Hawaii Tax ID: 104-909-0048-01):This roomy 2-bedroom 2-bath second floor unit is situated in the serene Wailea Grand Champions Villas. It offers luxury amenities, such as super quiet central air conditioning, a private lanai, in-unit...
Ocean View, Very Clean, Updated 1 BR Condo Steps from Beach, Shops, Restaurants
If you are looking for a well kept island-feel condominium at an affordable price, our unit, located 100 yards from the ocean, will not disappoint. Our beautiful second story condo is located in building 1 at the Kihei Kai Nani Resort. It has great ocean and beach views...
Beachside Penthouse ❀ Royal Mauian 604
Experience No. 604 at Royal Mauian, a comfy top-floor, air-conditioned beachfront sanctuary with breathtaking views. Nestled between two white sand beaches, enjoy the best of both worlds: dive into vibrant beach life or relax watching the ocean theater from your private...
OCEANFRONT Platinum Five Star remodeled villa! FRONT ROW!! Water views!! 27G1-2
This fabulous meticulously remodeled (recently) extra large one bedroom TWO bath villa (1300 square feet) is located within the Kapalua Bay Villa premier oceanfront complex. This villa, (significantly larger than ALL one bedroom level villas in the resort), is situated...
Newly Renovated 3 BR, 3.5 Bath Oceanfront Estate with Pool, Spa, A/C and Turtles
Our home was updated in 2021 and 2022 with new cabinets, countertops, appliances, sinks, faucets and dimmable recessed lighting in kitchen, baths, wet-bar and laundry; all new showers and a free-standing tub in the baths; all new walnut hardwood flooring throughout with...
Well Equipped Kitchen: 3Br Resort Luxury Condo-Private Beach Club, The Villages
COVID-Conscious Cleaning and Management Practices - Free long distance calls to US mainland, Canada and Puerto Rico. Free wireless internet and HBO and Showtime movies. You can Check Out on any date marked in Red on availability calendar.Enjoy a $1 million Luxury,...
Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BA
Wailea Beach Villas voted as one of the top 100 USA Hotels by the Conde Nast Traveler Readers Choice Awards!Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. Our Aloha Kai Suite is elegant...
Another Day in Paradise with Spectacular Oceanfront View of Kailua Bay
Probably one of the finest direct ocean views in all of Kailua-Kona. This 3rd floor unit looks straight over the ocean and Kailua Bay. Watch the whales breeching and the Spinner dolphins spin. Enjoy your favorite beverage on the lanai while watching spectacular sunsets....
Luxurious And Private 3-bedroom/3-Bath Townhome On The Mauna Lani South Course
3-Bedroom, 3-Bath Townhome overlooking the 10th fairway of the Championship South Course at the Mauna Lani Resort.Our condo is located in one of the two most desirable buildings in Golf Villas. It is an end unit overlooking the 10th fairway of the famous South Course....
OCEANFRONT TWO BEDROOM CONDO with A/C! Cal King Beds in Both Bedrooms!
Imagine - Warm tropical climate, sounds of waves washing ashore, palm trees swaying in the breeze, panoramic views, and the perfect accommodations - is there any other way to experience Hawaii?? This two bedroom, two-bath condo gives you all of that and more! The very...
Valley Isle Resort #1110 - Vacation West Maui
Just minutes to Ka'anapali, Napili, and Kapalua, the Valley Isle Resort will give you and your family the fun and relaxation it needs.Great Restaurants and Shopping Within Walking Distance of the ResortDirect Beachfront Accommodations on Kahana BeachFive 18 Hole...
Hualalai Hale: Four Seasons Modern Luxe Retreat on 1.5 Acres
Hualalai Hale: Your Luxe Private 4-Bedroom/4.5-Bath, Hualalai Resort Retreat, Tropical Landscape, expansive yard, Big Island HawaiiWelcome to Hualalai Hale—Your personal luxury resort home nestled within the exclusive and gated Four Seasons Resort Hualalai on Hawaii’s...
Kailua Beach "The Pink House" 100 Yards from Ocean
The Pink House is a perfect beach house set 100 yards from beautiful Kailua Beach. This Hawaiian Style Home has an open floor plan that includes a combination living/dining area with a galley kitchen with stainless steel appliances. Recently added Air Conditioning (we...
Luxury Villa at Mauna Kea w/Private Pool, Stunning Coastal Views & AC: Villa 21
This newly renovated ground-level villa in Kamuela offers the best of Big Island living. With panoramic views of the Pacific, Maui in the distance, and the lush greens of Mauna Kea’s championship course, this four-bedroom retreat is designed for families, couples, and...