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.
Luxury Villa l Designer Furnishings, Central A/C
Summary:E111 | TA-167-599-1040-01Experience refined island living at Villa E111, a luxurious Poolside Villa in the heart of Poipu. Outfitted with designer furnishings, a gourmet kitchen, central A/C, and in-unit laundry, this spacious retreat offers all the comforts of...
Luxury Villa Steps from Wailea Beach with Resort Amenities & Stunning Upgrades
This property is hotel zoned, and not being affected by the recent proposed legislation.Wailea Beach, voted one of the top beaches in the world, is a short walk from Ho'olei Villas. This amazing beach offers numerous activities such as paddle boarding, snorkeling, sea...
Spectacular Ocean View, Peace, Beauty, And Relaxation two to five guests
We invite you to explore Peaceful Hale, where abundant quiet and serenity, incredible views, sunsets and night skies with rolling hills and lots of open space await you at our end-of-the-road location. Nestled in the Kohala hills at 700' elevation, we enjoy bountiful...
Recent remodel - Large 1BR w/ ocean view and walk to excellent beaches/eateries
Recently Remodeled (2021)!Large 1BR unit at highly desirable Shores of Maui. The Shores is a place that people return to year after year, so once you've stayed there you'll likely do the same and return for years to come. A small 50 unit condominium complex with a mix...
Oceanfront Luxury at Honua Kai Konea 250: Stunning Views & Gourmet Amenities!
This property is hotel zoned, and not being affected by the recent proposed legislation.Honua Kai Konea 250 offers luxury at its finest! As you enter you will be in-awe of the breathtaking direct ocean views from this luxurious villa located at one of the most exclusive...
❤️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...
ALA 12 Perfect Getaway Remodeled Private 4Bedroom Beach House Near Beach
FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W3)*One...
Penthouse Luxury Oceanfront, Third Floor, 2 Bedroom | 2 Bathroom with Central Air
Lanikai 131 – Oceanfront Penthouse with Panoramic Views & Central A/CWelcome to Lanikai 131, a premier top-floor penthouse offering front-row views of Wailua Bay and Papaloa Cove. With 2 bedrooms, 2 bathrooms, and central air conditioning throughout, this elegant...
Spacious Ranch Cottage with private hot tub and VIEW!
Our Ranch House Cottage sits above the town of Kona with beautiful views of the Kona Coast. We are a 10-acre gated estate. This unit has a private Hot Tub/Jacuzzi with magnificent views. We a working farm with miniature goats, sheep and chickens. Fresh fruit and fresh...
NEWEST! California Coastal Inspired in Maui 2 BR
Located in the heart of Kaanapali, this spacious, newly remodeled, 1,440 square foot, ground floor, 2-bedroom condo is ideal for one or two couples, or a family of 6 looking for a relaxing getaway! This condo is ideally located in the heart of the Maui Eldorado, steps...
North Shore Beach House with AC, 30 day rental
LOCATION:**Message for special dates and availability not shown in the calendar**If you’re you looking for perfect white sand beaches with clear turquoise water & close proximity to everything in the North Shore, this is the place for you. Directly across the road is...
Hale 'Imi Ola: Ocean Views, Luxury, Balinese Charm
Hawaiian ease meets Balinese charm in this uniquely elegant, custom-designed South Shore villa, with luxuries galore & views for miles. Brand-new & wonderfully spacious, Hale 'Imi Ola offers the ultimate in stylish, relaxing indoor-outdoor living, complete with plunge...
Princeville Delight! COLD A/C, Sleeps 4, Pool & Jacuzzi, Private Lanai & Space
Aloha!This studio sleeps 4 with a Kingsize bed and a Queen pull out sofa. Located in Princeville on Kauai's North Shore across the street from the Makai golf course. The Princeville center is just a short few blocks away and you can walk there on the beautiful walking...
KKSR#5103 DIRECT OCEANFRONT, GROUND FLOOR, REMODELED, AIR CONDITIONING!
Keauhou Kona Surf & Racquet Club#5-103 DIRECT OCEANFRONT, ONE OF THE VERY BEST GROUND FLOOR UNITS! REMODELED WITH STUNNING VIEWS. Welcome to unit #5-103 at the Keauhou Kona Surf & Racquet Club! Knutson & Associates Property Management is so proud to be representing this...
Ocean Views, Walk to beach and town. AC, Huge lanai
Aloha!Great for longer stays! We supply reliable internet/wi-fi, a desk and comfortable office chair, and large monitor that makes our condo an ideal remote working location. Our spacious 2 bed 3 bath condo has ocean views, not only from our huge wrap around lanai, but...
U WANT 2 BE HERE!! Romantic 5* Reviews!!
Trust us- our property inspires you like no other!Looking for that special place to inspire you, and relax you and your family like no other?Our friendly and exceptional service sets us apart from others and you will enjoy your stay so much that you will want to return...
Ocean Views - Villa 1722 - 1 BR/2 BA Gold
Stay at your home away from home overlooking Kapalua Bay from your perch at Villa 1722. Start with breakfast in bed to take in the expansive water views. Plan you day with golf at one of the two Kapalua gold courses, tennis at the Kapalua Tennis Gardens, hiking on the...
Oceanfront condo in Poipu with balcony, W/D & partial AC - 10 steps to the beach
Kuhio Shores 410Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'E komo mai! Do you want on the water? This is it! You cannot get closer to the breaking surf than Kuhio Shores 410!...
A Cozy Cabin in the Country
Welcome to our haven of tranquility nestled in Hawi's breezy back country. At an elevation of 1800ft, our stylish retreat offers a refreshing escape from the ordinary. Start your day with a fresh cup of coffee and immerse yourself in the soothing symphony of wind...
Kaanapali Royal Q202 Modern 2BD Condo on Kaanapali Golf Near Beach w Pool AC
Please be advised that roof work is expected to take place 8/19-8/26 roughly. Since there are several floors above the unit, we anticipate minimal disruption from noise inside. Additionally, the parking lot closest to the building may have limited availability during...
Papakea G-205 - Ocean Views - Free Fun - NEW LISTING
Ocean views at Papakea Resort in North Kaanapali. This beautiful 2-bedroom, 2-bath condo in a 4-story concrete building has been updated.** NO RESORT FEES beginning July 1, 2025 **The master bedroom facing the ocean side features a king-size bed, TV and a safe to...
Gorgeous Elua 1 Bd+2Ba Executive Vacation Condominium - #2011
2011 Wailea Elua Village - 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 lanai...
Ground Floor Luxury, Perfect Family Spot, Quiet Lanai to Pool/Beach in 1 Minute!
Konea 106, Honau Kai Resort, is a fabulous ground floor unit (2 Bed/1 Bath) located at the center of the resort on the quiet side with a private lanai. Our lanai extends out to an open grass area which many of our guests use to relax, play games, or sit and enjoy the...
Wailea Grand Champions | 111
Wailea Grand Champions Villa 111 is a spacious two-bedroom, two-bath vacation rental condo that accommodates up to six guests, making it an ideal choice for families or friends traveling together. The first bedroom features a comfortable king-sized bed, while the second...
5-star and rave reviews. Amazing views. Newly furnished. Specials for April/May!
SPECIAL RATES for the 2025 Fall Season! Relax in what feels like your open-air home in paradise! Stunning views. Savor the outside air and breezes on your lanai. Superbly maintained. Consistent rave reviews (for years as we are original proud owners).Discounts for stays...
D35 Kona Reef - True Oceanfront & Top Floor! AC throughout!
Located just outside the heart of Kailua- Kona, this ocean front condo is your ticket to paradise! Just minutes from town, a short walk will take you to some of the finest dining and shopping destinations on the Big Island. Our modern, updated condo serves as the...
New "Beachy" 1BR, 2 Bth Kihei Condo w/Ocean/Mtn View-No Resort Fees!
It's cold and rainy outside...but not in Maui. We invite you to come and visit our condo and enjoy not only our 1 BR, 2 bath, full kitchen, LR, DR and no resort fees condo but also our private oasis. Palm trees are swaying, tropical breezes, island birds singing their...
Mauna Lani Terrace G102 Lagoon View Condo Beach - Restaurants, Bars Waterfront
⭕ UPSCALE LUXURY SUITE. LAGOONVIEW TERRACE #G102 ⭕ LARGE 1,150 SQ FT. WATER VIEWS OF LAGOON. COVERED LANAI ⭕ TWO MINUTE WALK TO OCEAN. 5 MINUTE WALK TO RESTAURANTS BARS ⭕ NO STAIRS! CENTRAL AIR CONDITIONING ⭕ FLOOR TO CEILING GLASS. LAGOON VIEW • Upscale...
Ohana Anini - Enchanted Beachfront Home on Kauai's North Shore
Mana Kauai Island Vacations Presents Ohana AniniReady to experience all of the beauty and adventure that the north shore of Kaua’i has to offer? Stay at our spectacular Ohana Anini beach house with breathtaking ocean views, gentle trade winds, and air conditioning in...
Hale Hui Kai 211 Large Lanai overlooking the beach
South Maui oceanviews from both bedrooms and the living room/kitchen. This private oceanfront condo is on the second floor of the south side of the building ...about 30 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on...
MAUI IS OPEN! Come visit!Westin Kaanapali Ocean Resort-beautiful 2 bedroom villa
Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sundays only. The Westin Ka'anapali Ocean Resort Villas is a gorgeous beachfront resort with luxury villas. Enjoy this villa and Maui's most spectacular...
Ocean & Diamond Head Exclusive Panoramic PH 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.The Waikiki Landmark high rise is located at 1888 Kalakaua Ave. on the main strip of Waikiki. Situated in...
BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!
If you are looking for luxurious, yet affordable, accommodations in a premier location, you have found it. The Grand Champions Villas are located in the heart of Wailea on Maui's sunny south shore - where the weather is just a little bit better than anywhere else on the...
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
Aloha and Welcome to Kolea LandingA short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom (king bed) with an en suite...
Truly Oceanfront - Rare 3BR - Amazing Sunsets & Awesome Views - SunsetShoresMaui
Truly DIRECT OCEANFRONT 3-bedroom END UNIT condo on the shoreline of Maui's beautiful west coast. SunsetShoresMaui offers unbeatable PANORAMIC OCEAN, ISLAND & SUNSET VIEWS from our nicely-upgraded, recently remodeled condo, located literally steps from the shoreline....
Affordable Rates, Upscale 2BR in Oceanside Complex!
This large upscale 2BR/2BA villa is at Hali'i Kai, the only OCEANFRONT condo community within the famous Waikoloa Beach Resort. Besides a great condo, you will get to enjoy Hali'i Kai's unique Ocean Club. Perched at the ocean's edge, it features a multi-tiered...
HIGH Floor w/Canal, Mtn and Partial Ocean Views! AC, W/D, WiFi, Pool,Parking!
Fairway Villa #2418 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! You'll love this corner property with its amazing Ala Wai Canal, mountain and partial ocean views and its proximity to shopping,...
RARE 2 BEDROOM, SINGLE LEVEL-2 LANAIS-WELL EQUIPPED-METICULOUS CLEANING-AC
Book with confidence, this nicely updated 2 bedroom, 2 bathroom (1086 sq. ft) single level condo. 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 24/7 to our...
Elegant 3BR Pili Mai 12A w/ Pool, Golf Course Views & Modern Amenities
Welcome to Pili Mai 12A by Gather, the perfect three-bedroom, three-bathroom condo in Koloa. This ground-floor condo, alongside the picturesque Kiahuna Golf Course, offers garden views and a newly designed layout with central air conditioning. Each of the three...
Hale Honu -Turtle House Oceanview Luxury Penthouse
Located in the beautiful area of Waikoloa Beach resort, just 5 minutes from the beach, Restaurants, shopping, and nightlife. Enjoy the Penthouse suite in Vista Waikoloa and ocean views from the wrap around Lanai. This unit has been completely renovated with a modern...
SPRING BREAK SPECIAL! Lau'eki Estate ~ Hualalai ~ Sweeping Views ~ Infinity pool
Step through a tropical courtyard into Elegant Lalani Lau’eki Estate, a 4-bedroom retreat with a separate Ohana guesthouse, ideal for couple getaways or family gatherings. A breathtaking hallway frames ocean views from the expansive lanai, where you’ll sip coffee as...
Snorkel at Kam Beach Steps From Chic Resort Condo!
Sink your toes into the sand of heavenly Kamaole Beach Park III found just a quick stroll from this tropical chic 1-bed, 2-bath condo! Featuring an ideal location on the lush acreage of Kamaole Sands, this Kihei vacation rental inspires pure relaxation coupled with a...
Reserve Your 5 STAR Big Island Get-a-way ⭐⭐⭐⭐⭐
Looking for just the right place to enjoy your Big Island Hawaiian Holiday? Treat yourself to a fresh approach. Your own private 1 bedroom 1 bath cottage. Newly renovated, this delightful guest cottage is tucked away behind gates at the end of a cul-de-saq. The perfect...
One of our best ON SALE & Wide Open (4/16- 5/8) ~ Must See OCEAN FRONT Villa ~
Welcome to Hale O Ho'okipa which translates in Hawaiian to 'House of Hospitality'.Truly one of the nicest ocean front villas in the Kapalua Bay Villa Resort! Some make this claim without conviction, but we have provided quality photos and a professionally produced video...
Spacious 5-bedroom villa in charming Kukuiula with AC, WiFi
Escape to this marvelous villa in picturesque Kukuiula in Poipu. This superb property boasts 5 bedrooms, including 4 king beds and 1 bunk bed, perfect for larger groups. With 5 bathrooms equipped with luxurious amenities like a bathtub and shower, guests will feel...
Waipouli Beach Resort Exquisite Ocean Front Condo in Oceanfront "H" Building
Oceanfront! Exquisite and Tranquil #1 Rated Oceanfront 2 bedroom, 3 bath condo at the beautiful #1 Ranked Waipouli Beach Resort & Spa on the island of Kauai.There is Central AC in this condo as well as a full size washer and dryer for laundry! Enjoy Oasis on the Beach...
Pili Pono: Elegant Honolulu Retreat with Pool & Private Oasis
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Pili Pono by GatherExperience the...
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...
Mountain & Waterfall Views - Pool & BBQ
Hawaiian jungle paradise awaits you at Villas of Kamali'i. Welcome to this fabulous split-level townhouse with wonderful mountain and waterfall views. The spacious design is beautifully furnished and is loaded with amenities to make your stay an extraordinary and...
Sans Souci Unit 1001 - One Bedroom
Nestled on Kaimana Beach, this charming, fully furnished one bedroom in Sans Souci is just steps away from the ocean. The unit boasts a complete kitchen and offers wifi & cable for your convenience. Enjoy the proximity to the renowned restaurant Hau Tree, located at the...