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.
Wai'ula'ula 312 by Gather w/ Pool/Spa, Ocean Views & Mauna Kea Resort Access
Nestled within the gated Wai'ula'ula enclave of the Mauna Kea Resort, this three-bedroom, three-and-a-half-bath luxury villa seamlessly blends island ease with refined design. After several years of private ownership, this beloved villa has been lovingly refreshed,...
Fairway Villas-2 Bed/2 Bath Lots of updates! Close to golf, shopping, and ocean
Welcome to our family’s piece of paradise. We’ve been travelling to Hawaii for twenty years, and our condo is the fulfillment of a dream to call the Big Island our second home. Our goal is to provide you with that same sense of aloha.Our 2BR/2 BA condo has a king in the...
Maui Resort Rentals: Luana Garden Villas 15C – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3BR/3BA residence is conveniently set within Enclave Three of the Luana Garden Villas. As a premier elevated offering, Villa 15C is defined by its west-facing orientation. Its designation within our "Elevated" collection at Luana Garden Villas offers a...
Nihi Kai 802 Sunset Spectacular, Ocean Views, w/AC
Summary:Enjoy spectacular sunsets and sweeping ocean views at Nihi Kai 802, a beautifully remodeled 2BR/2BA condo with full A/C. Located just a short walk to Poipu Beach and Brennecke’s Beach, this spacious retreat features an upgraded kitchen, modern bathrooms,...
Stunning Oceanview Villa w/Spacious Lanai, AC, Shared Pool & Spa: Kumulani (I-4)
2BD Kumulani (I-4) at Mauna Kea Resort is an upper-level corner retreat overlooking the Pacific, rolling fairways, and the Kohala Mountain range. Set within the gated Kumulani community above the world-famous Mauna Kea and Hapuna beaches, this bright and airy vacation...
Pure comfort in Paradise!
Location is everything with this property. Not only is the beach right across the street, you are also a short walking distance from restaurants and shops of every kind. This unit is away from the street completely remodeled from top to bottom in 2020 and on the second...
Exceptional Ocean Views - Renovated - Maui Kamaole #G-114, 1 Bd/2 Ba/ (Sleeps 2)
Welcome to your slice of paradise! Incredible ocean views, quiet, private and relaxing. The perfect place and location to call home during your stay in Maui. Note: Travelers to Hawaii will no longer be required to quarantine for 10 days provided they can provide a...
Spectacular Panoramic Ocean Views - Private Ohana - Wailea Custom Pole Home
Live like a local at the Ocean Blue Ohana. You'll have the entire private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500...
Bright, modern decor with ocean views
Maui Kai 504 1 Bedroom, Oceanfront Condo with AC. Panoramic Ocean Views Private & QuietReservation protected. This property resides in a district unaffected by any currently proposed Maui transient Vacation rental restrictions. Enjoy panoramic ocean views from this...
Westin Nanea Ocean Villas, Kaanapali Beach, Gorgeous, 2BdRm Ocean view
Large inviting living room, Gorgeous dining room, breathtaking large Master Bd Rm and ensuite bath with a large modern tub, an attractive second bed room with ensuite bathroom. Gourmet kitchen. One large lanai and a second lanai - great for a meal or drinks anytime!...
2BPF-1 Aston Waikiki Beach Tower: Ocean Front Premium 2 br with Kitchen
Waikiki Beach Tower: Premium Two-bedroom suite with Ocean Front Views and Full Kitchen right across from Waikiki Beach.Aston Waikiki Beach Tower provides the perfect combination of exclusive condominium living and attentive resort-quality service. Modern and lively,...
2BPF-1 Aston Waikiki Beach Tower: Ocean Front Premium 2 br with Kitchen
Waikiki Beach Tower: Premium Two-bedroom suite with Ocean Front Views and Full Kitchen right across from Waikiki Beach.Aston Waikiki Beach Tower provides the perfect combination of exclusive condominium living and attentive resort-quality service. Modern and lively,...
2BOV-4 Aston Waikiki Beach Tower: 2 Br with Ocean Views and Full Kitchen
Aston Waikiki Beach Tower: Two-bedroom suite with Ocean Views and Full Kitchen right across from Waikiki Beach.Aston Waikiki Beach Tower provides the perfect combination of exclusive condominium living and attentive resort-quality service. Modern and lively, this...
2BOV-2 Aston Waikiki Beach Tower: 2 Br with Ocean Views and Full Kitchen
Waikiki Beach Tower: Two-bedroom suite with Ocean Views and Full Kitchen right across from Waikiki Beach.Aston Waikiki Beach Tower provides the perfect combination of exclusive condominium living and attentive resort-quality service. Modern and lively, this condominium...
2BOF3 Aston Waikiki Beach Tower: 2 Br with Ocean Front Views & Full Kitchen
Waikiki Beach Tower: Two-bedroom suite with Ocean Front Views and Full Kitchen right across from Waikiki Beach.Aston Waikiki Beach Tower provides the perfect combination of exclusive condominium living and attentive resort-quality service. Modern and lively, this...
2BOF1 Aston Waikiki Beach Tower: 2 Br with Ocean Front Views & Full Kitchen
Waikiki Beach Tower: Two-bedroom suite with Ocean Front Views and Full Kitchen right across from Waikiki Beach.Aston Waikiki Beach Tower provides the perfect combination of exclusive condominium living and attentive resort-quality service. Modern and lively, this...
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...
Kai Hale: 3 BR Oceanfront Lanikai Beach Estate
AlohaRelax and unwind at Kai Hale. This beautiful Lanikai ocean front home is directly in front of the Mokulua Islands.This location is suited for year round living and is ideal for stand-up paddling, kayaking, boogie boarding, snorkeling, and children's activities. A...
Townhome in Waikoloa Resort - Close to Pool & BBQ Area!
Enjoy resort living at Colony Villas 201, a spacious two-story townhome located at the renowned Waikoloa Beach Resort. This 2-bedroom home is perfect for families or friends, and is close to all the best beaches, restaurants and shopping on the Kohala Coast. The home...
Luxurious, Spacious, High-end Beachfront Vacation Villa Free Parking
Dreaming of a memorable yet affordable Hawaiian vacation? Our Villa is calling you! It is located on the sunny Western shore of Oahu, and was built as a paradise for family-oriented beach lovers. It is landscaped with beautiful palm trees, koi ponds, a sandy-bottom...
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with...
Kulanakauhale 3558: Lavish Oceanview Estate, Private Pool & Spa at Hualalai
Important Resort Notices * Each December, Hualalai Resort holds its annual Chairman’s Club event. This event will result in temporary modifications to guest access at select resort amenities. Access is managed entirely by Hualalai Resort and may change at their...
Serene home with enclosed nature walk, meditation spot, & gardens
E Komo Mai Retreat Ohana | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Channel your yogi self and experience the serenity and spirituality of the EKomoMai Retreat....
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
The best location in Wailea! Quick 2-minute walk to Wailea beach, shops, restaurants & the stunningly scenic Wailea Beach Path. BOOKING CALENDAR/MINIMUM NIGHT STAY:Our calendar opens 1 year in advance. Please reach out if you want to inquire about specific dates prior...
Mauna Lani - Luxury 4 Bedroom Home - Sleeps 10
★ LUXURY KA MILO HOME – MAUNA LANI RESORT – SLEEPS 10Welcome to your Big Island getaway! This spacious 4-BEDROOM, 3.5-BATH HOME (2,100 sq. ft.) is located in the exclusive KA MILO COMMUNITY within the world-class MAUNA LANI RESORT on the beautiful Kohala Coast....
❤️PiH❤️BEACH CLUB BLISS ★ Bikes and Beach Gear ★ Close to Pool ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Beach Club Bliss, a part of our Hawaiian Luxury Collection. Beach Club Bliss at KaMilo is a wonderful single-level 3 bedroom home. We pride ourselves on providing some of the most sought after homes on the...
OCEAN FRONT Luxury Villa - Stunning Ocean Views - Steps To the Beach -Central AC
Summary:Be sure to watch our video from the link below:https://www.youtube.com/watch?v=JqTc_KOQqFwThis is when QUALITY meets LOCATION!!! Implacably maintained, built with only the best of the line in luxury, this Ocean Villa is located in arguably the best location on...
On the Beach! Kihei Sands Beachfront Resort, Unit A1
Kihei Sands is a Direct Beachfront complex, Popular Unit A1 - An Amazing Location!Aloha & E Komo Mai to our beautiful Condo, Unit A1~We purchased and completely renovated A1, we love spending time here as a family! Since we are new to the condo rental experience, we do...
Kainani Villa 5: Luxurious Indoor-Outdoor Living
This dazzling resort-style, garden-level condominium home is, quite simply, perfect—and what better way to enjoy your South Shore stay than in a comfortably luxurious, exquisitely appointed hideaway with spectacular views. Savor sun-splashed mornings on the capacious...
Lanikai Seashore by Gather: Oceanfront Home w/ Mokulua Views, AC & Lush Yard
Lanikai Seashore at 1270 Mokulua Drive is a stunning beachfront sanctuary in Kailua, HI, where you can experience the vivid beauty of Lanikai Beach just beyond your backyard. This luxurious 2,100 square-foot retreat artfully blends comfort and style, featuring exquisite...
3 bedroom amazing location ACN4
Welcome to our beautiful Alii Cove Townhome! This Gated Community is located on Alii Drive across the street from Hon'ls Beach and a five minute walk to the Village of Kailua-Kona, where you will find numerous restaurants, shopping, entertainment and other activities....
Newly Renovated Condo with SUP Paddle Boards and Golf Clubs Included
Newly renovated luxury short term vacation rental for up to 29 nights 2 bedroom, 2 bathroom en suit condo inthe greater Keauhou Resort area. Quiet Concrete Building! No Paper-Thin Walls Here, Folks!Located on the 8th fairway, our beautiful condo is situated in the...
Kuilima Estates West - 3 Bedroom Vacation Home
NEW LISTING! This newly renovated 2-story 3 bedroom condo is located at Turtle Bay in the gated community. This is the ONLY condo with split AC downstairs and central AC upstairs. This beautiful island condo sleeps 8 guests.This condo is just steps away to two...
Laid back Molokai beach-hideaway
One of the few Paniolo Hale units within steps to the beach! 2 Bedroom, 2 Bathroom, & Wrap Around Lanai with Ocean ViewsOur spacious, ocean-view townhouse is only steps from Kepuhi Beach. This 2000 sq ft townhouse feels more like a beach home with its generous living...
Monthly Discovery Bay 3717 Mountain/City Views 2 Bd 1Ba 2 Queen Beds
PANORAMIC MOUNTAIN VIEWS, 5 Minute Walk to Beach, High Floor, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Sauna, Security, Washer/Dryer Included. Monthly.Sweeping Views from High Rise, Tasteful and Clean. Monthly...
Remodeled "Seas The Day" Golf Villas Mauna Lani, Private Beach Club Access!
The kitchen and main floor have recently been renovated with fresh paint, new floors, designer furnishings, quartz counters, and stainless appliances.This well appointed condo is located in the gated Golf Villas community of Mauna Lani and features two bedrooms on the...
Updated 22nd Floor Waikiki Condo - Free parking & WiFi - Ideal for large family! by Koko Resort Vacation Rentals
Deluxe Updated Waikiki Condo - 22nd floor, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Great value. Ideal for groups...
Lokelani B102 – Premium Oceanfront Retreat Steps from the Sand
Experience the Elegance of Oceanfront Living at Lokelani B102 – Your Private Maui EscapeStep into your dream Maui getaway at Lokelani B102, a fully renovated beachfront sanctuary offering uninterrupted panoramic ocean views just steps from your private lanai. Nestled in...
Beautiful Maui Kamaole 2 Br, 2 Bath condo with Ocean view! New Summer/Fall rates
Beautiful VRBO Premier Partner Designation and 5 Star Property is in the B building, across from main pool and a 5 min walk across from Kihei's favorite beach. 2 bedrooms, 2 bath, over- sized unit with many high quality, unique upgrades rarely found in a vacation...
Oceanfront Art Gallery, Views-O-Plenty!
Welcome to the Oceanfront Art Gallery, where stunning sea views and artistic charm create a retreat like no other. Imagine waking up to the soothing sounds of waves and spending your days exploring the beauty of Kauai's North Shore. With stylish comforts and unique...
Steps to Beach. Stunning View. Lovely 2BR Condo near Wailea
Enjoy paradise at one of Maui's premier beaches. Our air-conditioned retreat features a clean and bright interior, offering stunning views from the main living area. Enjoy cooking in a well-equipped kitchen and relax with beach chairs, umbrellas, and boogie boards...
❤️PiH❤️ DAYDREAM VILLA ★ Bikes and Beach Gear ★ New Home ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to one of the newest homes in our Hawaiian Luxury Collection. Daydream Villa at KaMilo is a wonderful newer 4 bedroom home.We pride ourselves on providing some of the most sought after homes on the Kohala Coast...
Beautiful ocean front, ground level condo with A/C.
Welcome to beautiful unit E105! From the minute you arrive at Papakea, you will begin to feel the aloha spirit. This unit has been recently remodeled with granite counter tops, cabinets, bamboo floors in living room, new tile shower, new tile floors and new washer/dryer...
Direct Oceanfront on Maui's Finest Sugar Beach!
Boasting unbeatable ocean views and an oceanfront large pool, there is no better spot for your Maui vacation. This unique complex offers a library and lobby and is centrally located on Sugar Beach, the longest stretch of white sandy beach on this side of the island. You...
Luxury Condo Waikoloa Beach Resort, Gold Member Golf Package included.
This beautiful luxury 2 bedroom, 2 bath condo comes with amazing golf & pool benefits and is located in the Waikoloa Beach Villas at the Waikoloa Beach Resort. The space: Our beautiful newly remodeled luxury 2 bedroom, 2 bath condo comes with amazing golf & pool...
Kamaole Sands 4-213 - Beautiful Modern Renovation - Bright & Open - Split AC
Freshly remodeled throughout including a gourmet kitchen, Kamaole Sands 4-213 has been thoroughly updated to “second home” standards by its owners. Every guest convenience has been anticipated and addressed in this bright, open corner unit (more windows, more light,...
Kauai Beach Resort~Beautiful Mountain View
**Please read 'Other Things to Note' in listing** Capture the tranquility and beauty of the Garden Isle from this charming, centrally located condotel unit at the Kauai Beach Resort. From your private lanai, take in Kauai's lush landscape and majestic mountain views,...
Pili Mai Family Condo 5C, 3 Bedroom 3 Bath, Mountain View, Cool Lanai,
Pili Mai is the south shore's newest development and adjacent to Poipu's ocean view Kiahuna Champion Golf Course. Your dream vacation is waiting at this second story, 3 bedroom, 3 bath spacious condo. The lanai gives plenty of outdoor space to enjoy outdoor living for...
Nihilani Family Condo 11C, Impeccably Decorated, Close to Pool
Three bedrooms with 1 King bed, 2 Queen beds, 3 full bathrooms, 2 lanai spaces, washer and dryer in unit, 2 car garage, upgrades throughout, beautifully decorated, close to resort amenities.Wow! You will not be disappointed in this great Nihilani condo! Decorated...
Hale Konani, ground flr end unit with AC, golf & ocean views, 9M Pili Mai, Poipu
A stay at Hale Konani in the Pili Mai resort community has everything you need for the perfect Hawaiian vacation. This exceptional well-appointed three-bedroom, three-bath 1,500 sq. ft. condominium with central air conditioning is located on the Robert Trent Jones II...