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.
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...
Family condo at Turtle Bay on Oahu's epic North Shore
Enjoy beautiful North Shore paradise at our lovely Hawaiian beach cottage in prime location at popular Turtle Bay! Full kitchen, spacious living room, and many amenities including swimming pools, BBQ areas, beach gear/toys, pristine beaches, epic surfing, breathtaking...
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...
Maui's Premier Vacation Home: New Pickleball Court and Unmatched Luxury for Family Reunions
UPDATE: Starting March 20th, guests will enjoy our newly built pickle ball court, available for your private and exclusive use, located on property. Upon entering this gated estate, you'll instantly feel a sense of calm as you'll sense you have arrived in paradise. No...
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...
Hale Laniakea ~ 4 BR Modern Island Escape w AC
Hale Laniakea ~Princeville at Hanalei 4 Bedroom Modern Retreat Our home - Hale Laniakea, (Immeasurable Heaven) is located a private cul-de-sac in the best part of the beautiful Princeville resort. You will love being able to walk to Queen's Bath, Hideaways Beach &...
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...
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...
Oceanfront Condo with A/C, 10 Steps to the Ocean, Ground Floor, Kuhio Shores 112
Kuhio Shores 112 is a quiet, private oceanfront air conditioned condo that is 10 steps from the water’s edge. No need to deal with stairs or elevators; simply walk out the sliding glass door, and enjoy the ocean’s majesty! The first-floor location allows easy access...
Garden Retreat w/Ground Floor Ease - Kiahuna #2115
Kiahuna Plantation #2115: Tropical décor delights in this 690sf rare deluxe ground-floor suite. You and your friends or family can easily access the grounds from your ground-floor balcony and walk to world-famous Poipu Beach which according to "Travel Channel" was once...
Hawaii Life Rentals Presents Puu Poa 309
Welcome to your dream retreat at Puu Poa 309! This impeccably renovated (completed - 3/1/24) two-bed, two-bath condo has AC throughout and two oversized lanais that have one of the greatest views on Kauai's north shore. The condo combines a harmonious blend of modern...
Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper Floor
Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to offer. Get ready to make long-lasting memories while relaxing at this recently updated two-bedroom condo at the beautiful Palms at Wailea. This second...
Luxury Bali Hai Large Villa 2 BR, 2 Ba in Princeville, Kauai; Sleeps 6
This luxury villa is located in the exclusive Kaua’i resort of Bali Hai, in Princeville. This large upper level villa is a 2 bedroom, 2 bath unit that sleeps 6 with a king-size bed in the master bedroom and a luxurious private bathroom with a Jacuzzi tub. The 2nd...
NEW Full Reno 4BD/3B PRINCEVILLE HOME, STEPS FROM QUEEN'S BATH w/ AC & Jacuzzi!
LUXURY PRIVATE 4 bed 3 bath 1760 sf home on a >10K lot w/mtn views in Princeville, a luxury high end community. AC/Jacuzzi/Bikes/Beach Gear included. ***MAJOR RENO NOW DONE!*** ***New photos now up! 5 min. walk to Queen's Bath trailhead (follow safety signs!), ≈15...
Wailea Ekahi 24B - Modern Garden Retreat w/ Lanai, Split AC & Stylish Renovation
Nestled on the ground floor, Wailea Ekahi 24B is a beautifully remodeled one-bedroom, two-bath condo featuring a sleek, modern design and effortless indoor-outdoor living. With elegant finishes throughout, including quartz countertops and stainless-steel appliances,...
Incredible Highrise Views! | Heart of Town
Enjoy breathtaking ocean views in this recently completely remodeled 1-bedroom hotel condo, perfectly located next to Ala Moana Mall and across from Ala Moana Beach Park. Ideal for up to 4 guests, the condo features two double beds, a functional kitchenette, and a...
Location Location! Ekahi 32C! Designer Remodel 2bdrm $400 Remaining SpringSummer
Wailea Ekahi Unit 32C is a beautiful vacation condominium in the prestigious area of Wailea, known as the 'sunny side' of Maui. It is located on the greenbelt, just across from one of Ekahi Village's four private pools and a very short stroll to the beach and pool...
ICC 22 Beautiful 2BD Cottage Perfect Tropical Vacation
International Colony Club 22 Beautifully Designed 2Bedroom Cottage For the Perfect Tropical Vacation. Private, Next to the Pool, and Close to the Beach FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*:...
The Best Ocean View Studio Condo at the Royal Kahana Oceanfront Resort
We finished a complete remodel of the kitchen and the living room in December 2021.Stop!! You found it!! The best studio condo at the Royal Kahana based on the view, condition and price. If you've stayed in other studio's at the Royal Kahana it's time you stayed in the...