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.
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...
Aloha Condos, Kanaloa at Kona, Condo 3703, Oceanfront, AC
1700 Square feet of breezy vaulted-ceiling living space, with new tile floor and paint throughout. Refinished koa wood cabinetry in all new kitchen. Ceiling fans in all major rooms and lanai (5). Powerful whole house ventilating system reduces demand for AC. High...
Waikiki Shore Beach Front Studio
Large beach front studio (460 sq, ft,) located at the Waikiki Shore, the only condo building in Waikiki that is directly on Waikiki Beach. This unit is located in a building that is within the designated Resort Zone, and therefore eligible for short term vacation...
Waikoloa Village Golf Course Fairway 2-bedroom condo with Central AC-WiFi, Views
Waikoloa Fairways -From the Summit of Mauna Kea to the Kohala Coast Line, Welcome to Paradise! Central Air Conditioning! Aloha! E Komo Mai! This gorgeous condominium offers everything you need for your Big Island getaway. Located in the highly sought after community of...
Renovated 03/23! Direct Oceanfront Condo with 2 Master Suites!
*Available for booking! Thankfully, our condo is not located in the wildfire affected area*Enjoy stunning views in this newly renovated oceanfront condo located on Kahana Beach! This spacious 1,040 sqft condo located at Valley Isle Resort has been completely renovated...
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...
Hale o ka Nene: Luxury 6BR Estate with Pool, Spa & Golf Views
Welcome to Hale O Ka Nene, a striking six bedroom, six and a half bathroom estate set within the exclusive enclave of Kukui‘ula on Kaua‘i’s sun drenched South Shore. Designed for refined island living, this 4,200 square foot holiday home accommodates up to fifteen...
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 provided, you...
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, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Experience the charm of this corner unit with lanai on the 29th floor of the Waikiki Banyan, ideally...
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...
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...
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!
NOW ALL BEDROOMS HAVE AIR CONDITIONING TO GO ALONG WITH AC IN THE LIVING ROOMStay cool everywhere in the home!Hale 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...
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. Check...
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....
New! Maui Banyan G105 – Heart of Kihei
Maui Banyan G105 – Ground-Level Comfort Near the Pool in South Kihei!Welcome to your perfect Maui retreat! Located in the desirable Maui Banyan Resort, this ground-floor 1-bedroom, 2-bath condo offers comfort, convenience, and a fantastic South Kihei location—just steps...
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 perfect...
Maui Kam J209: Your Tropical Oasis in Maui
Escape to this spacious 2-bedroom, 2-bathroom loft condo at Maui Kamaole J209. Featuring an open living area, large primary bedroom with King bed, and a guest room with a Queen and a Twin bed, this condo comfortably sleeps up to 6 guests. Enjoy the lush tropical gardens...
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 Villas O414, a beautifully positioned 4th-floor corner villa offering a refined blend of comfort, island elegance, and effortless resort living. Overlooking the Ko Olina Golf Course with framed mountain vistas and a peek of the ocean, this...
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 central...
New Modern Hawaiian 2-bedroom house in Kapaʻa with amazing ocean/mountain views
Modern Beachside Escape in Kapa‘a – Steps from the Ocean!Welcome to your island getaway! This beautiful, newly built 2-bedroom home in Kapa‘a is just steps from the beach. Designed with modern island style, it features open and airy living spaces, a fully equipped...
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 the short walk to the beaches, shopping, and restaurants. This hidden gem is centrally located to Island travel spots, including white-sand beaches, phenomenal hiking trails, and active volcanoes. This second-floor 2-bed, 2-bath unit has outstanding...
Quality & Views- Centrally Located - Golf & Disney!
IDEAL FOR ... Corporate & Long Stays ! Centrally Located - CLOSE TO ... Golf & Disney !Our home is located in an exclusive Quiet Private area of Kapolei, Honolulu County, Hawaii, away from the hustle and bustle of town and yet close enough to all the Beaches, Shopping...
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...
ANY Closer U'D BE WET, Oceanfront, Ground Floor! ~25 FT 2 Ocean, Steps to Beach
March pricing discounted to lowest in years!.. . . . . . . . . . . . . . . . . WELCOME TO SUNSET CENTRAL! . . . . . . . . . . . . . . . . . . At Sunset Central YOU ARE SO CLOSE YOU CAN FEEL THE OCEAN! As soon as you walk into SUNSET CENTRAL you take a deep breath and...
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 experience....
Seaside Escape Just steps to the Beach!
Breaking News! Iconic, cultural, and beautiful Maui is back in business. We are proud to be welcoming guests to our legal vacation rental which has a full kitchen and is far more affordable than the pricey hotels and resorts. Thank you in advance for showing your...
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...
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
LAST BLOCK of time for the year just discounted! December is heavily discounted, spend the holidays in paradise! 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...
09 FREE Parking/10 min beach/2br-Waikiki/Ala Moana
Legal Vacation Rental!! Newly renovated! Excellent location! Central to Ala Moana Shopping Center, Waikiki attractions, beaches, restaurants, bars, zoo, business district; on bus line, easy commute to Downtown,Chinatown,UH. Secured building: security guard, 24-hr...