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.
MODERN MAUI I404! - MODERN LUXURY AND PANORAMIC OCEAN VIEWS
Private Paradise Villas personally manages 19 exceptional villas within this award-winning location, offering a curated and exclusive collection of 2.5 to 4 bedroom villas, most with panoramic ocean views. Private Paradise Villas is in part responsible for the recent...
Kolohala in Haena is a tranquil place to enjoy your tropical vacation!
Kolohala in Haena is a peaceful place to enjoy your tropical vacation. Great for honeymooners! It faces a beautiful meadow with horses and cows. You can walk to a string of white sand beaches in 5 mins. Close to Ke'e beach, Tunnels beach, Kalalau hiking trails, Napali...
Oceanfront Boutique Condo. 5% Discount for Most Stays of 7 or More Nights
Enjoy stunning ocean views from all the bedrooms and living area of the condo. Greet every morning on your bed enjoying the views and sounds from the ocean!*** OCEANFRONT overlooking greenbelt, quiet and private, no noise from pool or parking lot ***Uncork a bottle of...
Two Bedroom Upgraded Waikoloa Fairway Villa
Perfect for a postcard worthy family vacation, girls’ getaway, solo trip, or whatever your heart desires, Fairway Villa C21 is located in the Fairway Villas gated community of Waikoloa Beach Resort and is the perfect destination for rest, relaxation, reconnection, fun...
Luxurious 2-Bdrm, 2.5-Bath Condo with Parking & Fitness Center in Prime Waikiki!
Experience luxury living in this 2 bdrm/2.5 baths/1 parking, corner-end unit at Waikiki Landmark! Located in the Makai Tower, this unit offers breathtaking city and partial ocean views. No detail was overlooked in the thoughtfully designed kitchen renovation, featuring...
Luxury 6BR Hale o ka Nene Estate w/ Pool/Spa & Golf Views, Near Beach
Welcome to Hale o ka Nene by Gather, a luxurious six-bedroom, six-and-a-half-bathroom estate on the sunny South Shore of Kaua'i. Perfect for families or group getaways, this private retreat accommodates up to 15 guests and features panoramic golf course views, a private...
Hawaiian Bungalow ~ A/C~ Near Beaches & Shops
Experience the aloha spirit in this bright, airy Hawaiian-style home, where vaulted ceilings and tropical garden views create the perfect island retreat. Designed with family fun in mind, the game room offers ping pong and foosball, and the garage is stocked with...
Lei Hali'a - Steps Away from Poipu Beach with A/C!
Located just steps away from the world famous Poipu Beach and Brennecke’s Beach on Kauai’s sunny South Shore, Lei Hali’a is ready to help you create lasting vacation memories from this island paradise. From the spacious and comfortable outdoor living space...
Pu'uwai Place in the heart of Volcano Village
Pu'uwai Place is centrally located in the heart of Volcano Village, just outside Hawaii Volcanoes National Park. Cooper Center, convenience stores, and restaurants are all within walking distance. You'll feel right at home in this newly updated home with full private...
Beautiful Mountain Views & Steps to Waikiki Beach
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Oceanfront Paradise! Sea Turtle Cove Napili Point
WOW! Spectacular Ocean and outer island views. Your oceanfront patio is just steps away from the beautiful Honokeana Cove (commonly called turtle cove), which lends to excellent and safe snorkeling on most days. Sip on your Mai Tai, take a deep breath, and enjoy the...
STEPS FROM STUNNING MOLOAA BAY
Formerly "Hale Houston" Moloaa Beach Hideaway is a 2 bedroom, 2 bath home situated just steps away from beautiful Moloaa Bay on the northeast shore of Kauai. Walk up a flight of stairs to enter this 1200 sq.ft. spacious, air conditioned well appointed home with an open...
Ocean View Paradise: Spacious 2-Bedroom Condo at Kaanapali Shores
Experience the ultimate Maui getaway at Kaanapali Shores 416, a beautifully maintained 2-bedroom, 2-bathroom condo that promises breathtaking ocean views. The open-concept living space seamlessly blends indoor and outdoor dining, making it easy to savor meals while...
Gratitude Bed and Breakfast BBWK2022/0001
This is a Bed and BREAKFAST, I provide you with Local food for breakfast!We are within walking distance to Wailuku town which has coffee shops, restaurants, boutiques, antique shops and Local Acting Theater. You’ll love my place because of the coziness, the vaulted...
Wailea Ekolu #405 Ocean Views on Wailea Golf Course, Wifi, A/C
Introducing the newest unit in our portfolio! Please visit and be our first review with an introductory Special Rate till August 31th! Wailea Ekolu #405 is an ocean view 2 bedroom, 2 bath ground floor unit with air conditioning throughout, a fully equipped kitchen,...
Mauna Kea Luxury - 180º Ocean, Maui & Sunset Views, Heated Private Pool & Spa
This stunning home offers the best of both worlds: the comfort of a spacious, private home and access to all of the facilities of the Mauna Kea and Hapuna resorts. All four bedrooms have en-suite bathrooms. We have not furnished and equipped this as a "rental property",...
Hale Pohaku Kai: Poipu Seaside Stunner
Hale Pohaku Kai is a paradise of paradoxes: elegantly furnished, yet casually comfortable; spacious & airy yet cozy, too; wonderfully private, but with Poipu’s world-class sandy beaches, parks, restaurants, shopping & lively local events only a few minutes away. The...
CozyTiki cottage w/ 2 private rooms, outdoor kit/bathn
Nestled in the jungle, our cozy tiki hut offers 2 adjacent comfortable rooms, each with its private entry from a shared lanai/outdoor living space. A covered outdoor walkway leads to a small but practical kitchen and shared bath among cottage guests only. Queen beds and...
Actual Owner! - Marriott Beautiful Ocean Front Villas- 2bdr/2bath sleeps 8+1
Special cancellation policy for Pandemic quarantine restrictions; please inquire for details.Marriott continues to closely monitor and comply (exceed) the Centers for Disease Control and Prevention (CDC), World Health Organization (WHO) guidance.We will be happy to...
BIG ISLAND HALE MELE MELE, Lovely Cottage in Magical Puako!
SUMMER SPECIAL:JUNE 1ST THROUGH OCTOBER 31ST: STAY 7+ NIGHTS GET 1 NIGHT FREEHale Mele Mele is one of Puako’s original beach cottages lovingly restored, refreshed and redecorated to feel like home-away-from-home. The fully-equipped kitchen, while compact, has all you...
Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
The Maui Meadows Guesthouse Property is 3/4 mile from (8) premier beaches and features: (4) Bedroom, (5) Bath one story 2700 sq ft house, Proximity to beaches, activities, golf, shopping, restaurants and bars, Air conditioning, 65" TV screen with Streaming TV with NFL...
Kuilima Condo with Split Air
Welcome to our little piece of paradise. A perfect place to stay during your visit to Oahu. Our CLEAN and beautifully UPDATED condo can sleep 6 comfortably. With TWO king beds and a one queen sofa bed. It also includes a brand new full-size kitchen with a dishwasher,...
Private pool and jacuzzi oasis; walk to the beach, golf, restaurants, shopping
Your own private tropical pool and jacuzzi! Hale Ohana is open concept home with an expansive living room, dining room, and kitchen with breakfast bar that are to be enjoyed. Ceiling fans and Hawaiian louvered windows in every room allow you to enjoy the cool trade...
Top Floor Ocean Front Molokai 1 Bedroom Condo
Our condo is located in east end of island of Molokai. It is “NOT” on Maui. Recently totally renovated.Has spectacular views of the ocean and of west Maui coast. Watch whales from lanai during mid Dec-early April Book now don’t miss out everything is filling fast....
New Listing! A/C ~ Ocean & Golf Course Views ~BBQ
Relax & recharge in this calm, stylish space. The A/C or tropical breezes await you after a day of island adventure. Nestled near the ocean bluff along the Makai Golf Course. The kitchen is fully equipped. New furniture throughout. Private gas BBQ. Private washer/dryer....
Maui North Shore Villa: Private Pool, Courtyard & Steps to Baby Beach
Your North Shore Beach Retreat in Maui’s Premier Neighborhood:Nestled in the heart of Spreckelsville, this is more than a beach house—it’s a place to slow down and savor what makes Maui special. Just a 3-minute walk from Baby Beach, with its calm lagoon waters...
Ocean-Waikiki Skyline Panoramic PH in Luxury Condo w/Parking & Near the Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.*This penthouse is new to our inventory. Reviews are coming soon. Please rest assured this house is...
Stunning Ko Olina 2BR Beach Villa O414 w/ Golf Course, Mountain & Ocean Views
Welcome to Ko Olina Beach Villa O414 by Gather, an exquisite 2-bedroom, 2-bathroom haven in Kapolei, HI, perfect for up to six guests seeking a blend of luxury and comfort. Located on a serene corner of the 4th floor, this villa presents stunning views of the golf...
NEW LISTING SPECTACULAR OCEAN FRONT VIEW FROM EVERY ROOM - PRINCEVILLE/HANALEI
A beautiful, unobstructed view of the deep blue Pacific Ocean and coral reef from every room! Our condo is located on an ocean bluff having the luxury of a 180 degree view of blue water from every room. Along with magical waves, you will see outrigger paddlers and sea...
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
Indulge in an Unforgettable Stay at Our BRAND-NEW Luxury Beach House at Kailua BeachEscape to our newly built, luxurious rental home, perfectly nestled in the heart of the most sought-after location by the world-renowned Kailua Beach. This contemporary haven is designed...
Charming Ocean View Home with Central A/C - walk to Downtown Paia and Beaches
Experience the beauty of Maui’s North Shore from this private, ocean-view home just minutes from downtown Paia and some of Maui’s best beaches. This spacious 3-bedroom, 2-bath vacation rental offers the perfect balance of tranquility and convenience, featuring...
Mauna Lani Point | B107
Welcome to your dream Big Island getaway! This stunning one-bedroom residence offers breathtaking ocean views that will captivate you from the moment you enter. The tranquil ambiance envelops you as you relax in the spacious living area, adorned with tasteful decor and...
Wainani "Heated Pool, Hot Tub, Game Room & A/C"
5 night minimum stay required.Beautiful Wainani home overlooking the 4th Fairway of the Kiahuna Golf Course. Located in a cul-de-sac in the Wainani neighborhood in sunny Poipu. Close to shopping, dining and several beaches (Poipu Beach Park, Shipwrecks, Brennecke's to...
OCEANVIEWS, FRESH UPGRADES AT THE LUXURIOUS GRAND SEASCAPE K407!!
Situated in the centrally located "Penthouse" building on the 4th floor in a west-facing ocean view corner location with breathtakingly beautiful panoramic ocean and sunset views, this 2.5 bedroom (king bed in each bedroom plus 2 twin beds the enclose-able den that can...
Spectacular Beach Resort Condo - Summer Special - Amazing Views
You will love how close we are to the beaches, shopping, restaurants and central to travel and hiking spots and hidden gems. This second floor 2 bed 2 bath unit has phenomenal mountain views with peak a bay ocean view and located on the Kings golf course. With over...
Includes Beach Gear. Waikoloa Fairway Villas G4
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Fairway Villas G4Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom : Two Full Size BedsLiving Room: Sleeper SofaNew in 2022!Newly...
Last Minute Spacial! Oceanview's on 31st Flr
**Notice:There is a one time check-in fee of $50.00 and $30.00/daily resort service fee for unlimited access to the building resort facilities. This fee is mandatory and must be paid during check-in at the hotel front desk.The daily parking rate is $39.00. Tax(17.962%)...
Spectacular Ocean Views, Luxury Resort-style Home, Waterfront Privacy
NOTE: NO BACK-TO-BACK BOOKING! There needs to be 24 hours between bookings to ensure proper cleaning. Please make sure your check-in or check-out date does not coincide with an existing check-out or check-in date from another booking. When you walk through the front...
Maui Resort Rentals: Honua Kai Hokulani 511 - Upgraded 5th Floor Interior Courtyard 2BR w/ Full Ocean Views!
Hokulani 511 boasts an incredible 5th-floor interior courtyard location with full ocean views above the palm trees. Gather, reconnect, and celebrate in this spacious 2 bedroom floor plan which offers an abundance of interior living space with an additional 235 sq ft of...
Stunning 2 Bedroom Luxury Cottage 300 feet from Poipu Beach Park
TMK: 4-2-8-018-005-0001-000This custom designed Hawaiian plantation style cottage is located just off the Brennecke's beach side of Poipu Beach Park, 100 steps to the beach!This spacious house was designed and built in 2013 to be the perfect vacation retreat - its...
SPRING SPECIAL! See Our Location!..Read Our Reviews!..So Many Extras!
Our 'home away from home' townhome is the perfect place to enjoy your vacation! It is luxuriously decorated with top of the line furnishings and orginal art work, yet extremely comfortable and welcoming. Since our townhome is NOT a full-time rental, you can relax in...
Oceanfront at Sugar Beach
•EAST/SOUTH MAUI IS OPEN FOR BUSINESS AND WELCOMING TOURISM•Life is sweet on Sugar Beach. Our oceanfront condo is fewer than 100 steps to a world-class beach that stretches for 5 miles. The smooth sand, gentle waves, and warm water create the ideal swimming...
Relax by the Sea, in this awesome 2 bedroom Condo
Halii kai is an Ocean front Resort in the beautiful Waikoloa Beach Resort. What sets 16B apart from the rest? Location, amenities and service. I live on Island and can assist with any issues or questions. Halii Kai Unit 16B is right across from the clubhouse. Enjoy the...
Colorful condo by the beach with a washer/dryer, lanai, & on-site pool
Paniolo Hale S3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked away on the beautiful west end of Moloka'i, this sunlit and colorful condo is sure to delight you and your...
Lily's Kona Hideaway-Oceanfront & AC on Demand
Welcome to your Hawaiian paradise! This renovated second-floor condo at Kona Isle blends modern luxury with island serenity. Bright, open spaces and upscale comforts await. Enjoy a solar-heated pool, oceanfront BBQ, and lounge with spectacular sunset views. Soak in the...
Best and Newest Beachfront Listing in Honolulu
THE HOMELAST MINUTE DISCOUNT AVAILABLE FOR AUGUST AND FIRST HALF OF SEPTEMBER. INQUIRE FOR DETAILS. This is a completely modern, sandy beachfront villa in a private and secluded location in Honolulu that is the perfect home and location to get away from it all. This...
NEW Ocean Front Condo w Amazing Views
Coconut Breeze is a studio beachfront condo, it is the epitome of luxury & relaxation. Located on one of the most beautiful islands Maui, our condo offers the perfect blend of comfort and convenience. Imagine waking up to the sounds of crashing waves and stepping out...
Charming & Updated Maui Banyan 2 Bath
Discover Maui at Maui Banyan H109 apartment, a charming 1-bedroom, 2-bath condo steps from Kamaole Beach Park II. Conveniently on the first floor, it hosts up to 4 guests. Relax on the lanai amidst lush greenery, stroll to the nearby beach for breathtaking views. Stay...
Aloha Living! E Komo Mai
This bright and sunny unit boasts wonderful city and mountain views. If you're looking for a clean, updated, secure, fully furnished, warm and inviting place to call home away from home on your Aloha vacation… look no further!*RARE - Garage Parking...
DIRECT OCEAN FRONT/GROUND FLR, PANORAMIC DRS, 2 BED/2 BATH EN SUITES, DISCOUNTS
Hali'i Kai is a gated community located in the Waikoloa Beach Resort area, approximately 18 miles from the Kona Airport. Weekly and monthly discounts are available.Our Hale, unit 13, includes fold-a-way Panoramic doors, replacing a traditional sliding glass door that...