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.
Hale Mikana - Gorgeous Ocean Views, Pool and AC!
This gorgeous home has a large private pool and views of Kauai's serene ocean and mountains. Just steps from one of the worlds most beautiful golf courses, this homes location makes for the perfect tranquil vacation. Hale Mikana includes air conditioning in every...
Beautiful spacious 2 bedroom townhome at Mauna Lani! With A/C and WIFI!
Make memories and enjoy the perks of this quiet gated community at The Fairways at Mauna Lani. This spacious townhome has all the amenities and is located north of the Kona International Airport, on the sunny Kohala Coast. This townhome is nestled in the prestigious...
Waikiki Landmark Resort and Condos - Breathtaking 2Bed,2Bath, Free Parking
Treat yourself to a Honolulu getaway you won’t forget! Book a stay at this 1-bedroom, 1-bath vacation rental and enjoy resort amenities like rooftop pools, a hot tub, a worldclass fitness center, and more! The condo boasts floor-to-ceiling windows in both bedrooms...
🏖️4 Main Suites | | AC & Private Pool | Ocean View | vrKCV
vrKCV - Keauhou Estates Hale Ohana lea 8, Professionally Managed by Kona Coast VacationsWelcome to Halele'a, the House of Joy—a breathtaking Hawaiian retreat nestled within the private, gated community of Keauhou Estates. Designed to seamlessly blend luxury and...
Whaler 1273: Spectacular Penthouse Panoramic Ocean & Golf Course Views
Oceanfront 2 bedroom 2 bathroom for Whale WatchingThe ultimate in luxury, one of the few truly beachfront condominiums located right on Maui's famous Ka'anapali Beach. This spectacular oceanfront condo features two bedrooms, two bathrooms and breath taking views of...
Updated Condo in Oceanfront Resort w/ AC & Shared Pool, Water slide, Spas
Waipouli Beach Resort D207Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to this beautiful, second-floor condo in Waipouli Beach Resort - an oceanfront complex with heated...
AMAZING VIEWS-Kalapaki Cliffside Penthouse-Perched above, elevator to the sand!
Perched high on the Kalapaki cliffs overlooking gorgeous Kalapaki Bay this home serves as the perfect home base to explore the entire island on your unforgettable Kauai vacation. Fall asleep and awake to the relaxing ocean waves nightly at our home perched over the...
Private Lanai with the Best View in Town!
**Nohonani 405 – Your Oceanfront Sanctuary**Welcome to Nohonani 405, a stunning 2-bedroom, 1.5-bath unit on the fourth floor, featuring vaulted ceilings and breathtaking ocean views. Enjoy panoramic vistas from the kitchen, dining areas, living room, and master bedroom....
Pane Makai Poipu Beach House - Steps to the Beach!
Less than a minute's walk to the beach, Pane Makai is spacious, air conditioned, and can sleep up to 24 people! Located in sunny Poipu, Pane Makai and is the perfect gathering place for groups, large families, friends, and loved ones. This 6,000 square foot home is...
Maui Rainbows And Waves! ~Gorgeous Oceanfront! ~ 2 Bdrm ~Corner Unit with A/C
****TEMPORARILY CLOSED DUE TO THE DEVASTATING LAHAINA FIRE...WE HOPE TO BE BACK ****. APOLOGIES FOR THE CAPITAL LETTERS BUT IT'S VERY IMPORTANT THAT WE AS OWNERS ARE UP FRONT AND HONEST REGARDING THE CURRENT CONDITIONS OF LAHAINA TOWN...WE ARE A FEW BLESSED THAT OUR...
5 STAR CONDO, OCEANVIEW, FAMILY FRIENDLY
MAUI FIRE UPDATE: Papakea Resort services (electricity, water, cable, internet) are fully operational. All recreational areas are open and returned to regular operations. Maui is OPEN and welcomes respectful, caring, and compassionate tourism.PROPERTY DESCRIPTION:This 2...
"New" Luxury property. Walking distance to The One Hotel and Beach
This three-bedroom, three-bathroom condo is located in the heart of the Princeville resort community on Kauai. The spacious condo is air-conditioned and has great lighting, making it a comfortable and inviting space to relax in. The modern kitchen features granite...
Maui Sunset Vacation Rentals B510
From on the fifth watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. Large private condominium apartment at the resort condominium complex on the beach in sunny...
Oceanfront, newly renovated. As low as $220/night.
You will find yourself right on the ocean and far from the highway! Sit and relax on your private lanai while watching the waves roll into Wailua beach. The view is truly spectacular. Many guests have shared stories of watching whales breach on the ocean surface for...
Ground floor unit w/ golf and ocean views, three pools and tennis on site
Country Club Villas 102Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to this beautiful ground floor vacation rental which lets you drop your bags at the door, walk onto the...
Puamana 272-3 presents a unique opportunity to experience oceanfront.
Puamana 272-3 presents a unique opportunity to experience oceanfront living at its finest. Relax on your spacious lanai, just 50 feet from the water’s edge. Here, you can grill, dine, enjoy the ever-changing ocean views, watch surfers riding the waves, observe seasonal...
Oceanfront Condo with Absolutely Breathtaking Ocean/Sunset Views - B238
Incredible Oceanfront corner location with an unsurpassed view of the ocean and sunsets. Enjoy 700' of tropical outdoor living on your L-shaped lanai. The sound of the waves will lull you to sleep since you are only 30' from the ocean. Comfortable tropical decor is...
KS 404 Remodeled OceanFront 2Bedroom Condo w AC Pool
Kaanapali Shores 404 Recently Remodeled 2BD/2BA Ocean Front Condo at Kaanapali Shores KAANAPALI SHORES IS A HOTEL ZONED LEGAL VACATION RENTAL PROPERTY FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale...
🌺🌺 UNIQUE VILLA with Indonesian Flair! BEACHFRONT RESORT 🏖️🏖️
***December 2025 - New King mattress in Master bedroom***August 2025 - Villa refreshed with new smart TV in living room, linens, towels, cushions, rug, guest bedroom furniture, and new furniture set to relax in the lanai.Relax...Escape from the hustle and bustle of the...
Sugar Beach PH32 Ocean Front Views steps from 5 miles of Beach
Book with us and come to Maui to explore everything we have to offer!This beautiful just remodeled unit at Sugar Beach is located on the top floor overlooking the south Maui bay. With views for miles from the balcony, you'll be able to see sunsets, whales, and miles of...
Ocean Front Paradise at Magic Sands Beach With AC
The first thing you will notice when you enter the condo is the view of the ocean that fills the entire glass slider making you feel like you are on a ship out at sea. One guest said they dropped to their knees and wept because of the overwhelming view of the ocean....
Maui Resort Rentals: Marriott's Maui Ocean Club 1 Bedroom Oceanview Suite
Freshly Renovated One Bedroom Ocean View Suite at Marriott's Maui Ocean Club! Family time is limited, make the most of your vacation time with an out of this world Ocean front experience. Why pay for a small hotel room when you can get TWICE the size for about the same...
Sunny Fourth Floor Condo with Shared Pool, High-Speed WiFi, and Washer/Dryer
Maui Banyan Q408Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy the privacy and space of this charming beach condo, with a view of the shared tennis court and ocean to inspire...
Hana Ocean Palms Bungalows
The Hana Ocean Palms Bungalow is located across from one of Hana's most beautiful oceanfront pools - Waioka Pond (Venus Pool). The property is nestled in a coconut palm grove and surrounded by almost an acre of lush tropical flowers, fruit trees and bamboo. Pick...
Whaler #1074 Remodeled One-Bedroom Two-Bathroom Ocean View
The Whaler on Kaanapali Beach #1074 is a beautiful one bedroom, two bath ocean view unit located on the courtyard corner of Tower II. It's 10th floor location provides expansive views that stretch from the lush West Maui mountains across the courtyard and out to...
Absolute OCEAN FRONT unit on famous Banyans Surfing Beach!
This unique, ocean front unit has all the feel of Hawaii, from it's tropical decor & palm trees to the ocean below! Watch the surfers from your private lanai. Fall asleep and wake up to the sound of the ocean waves as they break not 50 feet away from you! Enjoy walking...
Hilton Waikoloa Pool Pass Included for stays thru June 2025! Waikoloa Fairway Vi
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Fairway Villas O4.Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: Two Twin BedsGuest Bedroom Downstairs: One Queen BedSleeper Sofa:...
Sugar Beach Resort Condo w/ Shared Pool/Hot tub, Free WiFi-Beaches Await
Sugar Beach Resort 140Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
Maui Sunset Resort A102 - Aloha Mai, Remodel, Ground floor, 1BR/2BA, Sleeps 5, A
Summary:Oceanfront Resort Condo Suite - ground floor tastefully-remodeled (2020) 1-Bedroom with King Bed, 2-bath w/ Queen Sleeper & Queen Murphy bed in LR. Family Friendly, sleeps up to 5, Full Kitchen, AC, Washer/Dryer in-suite, Free WIFI & Parking, Cable/Flat Screen...
❤️PiH❤️ KOHALA HAVEN ★ PLUS Hilton Resort Passes ★ 3 Full Bath ★ Closes to Pools ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Kohala Haven, a part of our Hawaiian Luxury Collection.Kohala Haven at KaMilo is a wonderful new single-level 3 bedroom home. We pride ourselves on providing some of the most sought after homes on the Kohala...
Nihilani 32C - House of the Golden Ocean
This North Shore Kauai private condo rental features 2 Master bedrooms, Plus extra sleeping space in a Trundle in the Family Room, two dining and living areas, a large kitchen, and access to the Nihilani at Princeville resort amenities.The spacious, furnished lanai...
Large Home w/ 2 covered Pickleball Courts near Volcano National Park sleeps 16
Hawaii Pickleball Addicts Lodge is a beautiful, large private home with 2 covered Pickleball Courts (35' x 60' x 22' each) on 2 acres in Mountain View, HI, close to Volcano National Park, Kea'au, Kalapana Black Sand Beach, Uncle Robert's Awa Bar and Farmer's Market, and...
KBM Resorts | FREE CAR | Honua Kai Konea | Garden view | 2-Bedroom Condo with Large Courtyard views! HKK-343
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Hale Kona Kai 404 - Find your Beach with Kona Beach Properties
Hale Kona Kai 404 is uniquely designed. The bedroom and living room are separated by sliding french doors instead of the traditional closed rooms. This allows the condo to open up into one large space. A great benefit to this layout is that the AC works much more...
Beautiful 3bd 3bth Condo SOUTH KIHEI Maui Hawaii CENTRAL AC Kamaole 1 Beach
Welcome to Paradise!5 Min walk across the street to the Beautiful & Sandy Beach Charley Young & Kamaole 1.Perfect for sunbathing, swimming, building castles and snorkeling! Enjoy all the comforts and amenities of our beautiful condo to make this your ultimate vacation...
NORTH SHORE OCEAN FRONT - 30 day rental TA 044773171201
Welcome to Hale Aloha. Please inquire about staying at our property! Our home was recently remodeled in 2016 with new everything including central AC and has a detached enclosed garage. This is the first time it has been available for rent and is in excellent condition...
Kona's Shangri La: Oceanfront Home with Pool & Spa
Perched directly above the blue curve of Lyman’s Bay, Kona’s Shangri La is a custom tri-level oceanfront retreat designed for families and groups seeking space, comfort, and effortless island living. Set along the iconic Ali‘i Drive coastline in Kailua-Kona, this...
STUNNING OCEAN VIEW CONDO! Fully Remodeled! Ground!Private!Bunks!Large Lanai!
EKAHI 51B Wailea Ekahi 51B is a luxury high end condo in the highly sought after ocean front complex Wailea Ekahi Village. We purchased this condo and have completely remodeled it . The results are stunning. This is the largest one bedroom two bath plan in Ekahi. We...
Maui Resort Rentals: Honua Kai Konea 337 - Large Luxurious Studio w/ Lush Courtyard and Peek-a-boo Ocean Views!
This luxurious corner studio condo sits directly above the beautiful courtyard of Honua Kai and offers peek-a-boo ocean views through the lush tropical foliage. When you walk out onto the lanai, you'll marvel at all the beautiful flowers, trees, and koi ponds all around...
New Listing! Recently updated spacious 1bd in Maui
Welcome to Kihei Ali'i Kai D204! Step into your Maui home-away-from-home in this bright and beautifully updated one-bedroom, one-bath condo. Perched on the second floor, it offers a lovely partial ocean view—perfect for morning coffee or sunset moments on your...
Whalers Cove Unit #113 - Spectacular and Secluded Oceanfront Condo with Pool!
Whaler's Cove 113 – Oceanfront Luxury Condo with Stunning Views of the PacificExperience the ultimate beachfront getaway at Whaler's Cove 113, a secluded 32-unit oceanfront hideaway on Kauai’s South Shore. This luxurious 2-bedroom, 2-bath condo offers breathtaking views...
Keauhou Racquet Club Condominium
Experience the ultimate retreat at our very private 2-bedroom, 2-bath condo in the serene Keauhou Racquet Club. Embrace the luxury of a gated community offering a large swimming pool, professional tennis courts with night lighting, and complimentary parking. The...
BEAUTIFUL POIPU OCEAN VIEW 2 BRD 2.5 BATH Condo with A/C nSpring 25' Dates Openn
The beautiful Makahuena resort is located on the southern most tip of the island of Kauai in Poipu Beach. Offering breathtaking views of the Pacific ocean from the bluffside townhome style deluxe condominiums.Split level air conditioning in both bedrooms makes for cool...
Ilikai Hotel Renovated Condo Steps Away From Beach w/Free WiFi & Full Kitchen
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.ILIKAI BUILDING NOTICE:Spalling repairs and full exterior painting of the building in effect. Please be advised: Balcony access for this...
Beautiful Ocean Facing Condo on Kaanapali Beach!
Nestled amidst the breathtaking vistas of Maui, this expansive one-bedroom condo presents an unparalleled ocean panorama, boasting captivating views of Molokai and Lanai. Set against the backdrop of one of Maui's most picturesque beaches, our retreat offers an array of...
Royal Mauian 607: Oceanfront Serenity Awaits in This Amazing Condo! - With A/C
Royal Mauian #607 – Penthouse Oceanfront Luxury in KiheiRoyal Mauian #607 offers the ultimate Maui getaway with its top-floor location, upgraded modern décor, and panoramic oceanfront views. This two-bedroom, two-bathroom condo combines contemporary style with the...
❤️PiH❤️ SAND CASTLE ★Ocean Views ★ Spacious and comfortable for larger families ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sand Castle Villa, a part of our Hawaiian Luxury Collection. Sand Castle Villa at KaMilo is a wonderful 4 bedroom home.We pride ourselves on provide some of the most sought after homes on the Kohala Coast and...
Wailea Grand Champions 168 - Complete Remodel - Amazing Golf Course/Ocean Views
Hawaii Tax ID: TA-144-497-4592-01COMPLETELY REMODELED - GOLF COURSE & OCEAN VIEWSGrand Champions #168 is a impeccably kept one-bedroom two-bath luxury villa with amazing golf course and limited ocean views. The unit is located on the 7th fairway of the the Wailea Blue...
NEWLY REMODELED-RARE GROUND FLOOR 2 BD-NICELY UPDATED-AC-METICULOUS CLEANING
Book with confidence, this newly remodeled 2 bedroom, 2 bathroom (1086 sq. ft) ground floor 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 to our guests....
EL K203 2BD Condo w AC Pool Beach Cabana
Eldorado K203 Incredibly Spacious Condo with Amazing Sunset Views-Perfect for Families Eldorado K203 is the ultimate Kaanapali Maui vacation spot! This bright and airy condo will easily fulfill all your needs for a fabulous stay, highlighted by breathtaking sunset and...