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.
Premier Ocean View! King Luxury Bed, A/C, Clean, Cozy, Updated, Wifi, Beach Gear
Legally zoned vacation rental unit. We are hands on owners. All communications will be with us directly. We have been in the business since 2008 and operate with a valid State of Hawaii license 091-649-8432-01.Welcome to Kauhale Makai (Village By the Sea) and your home...
Remodeled, Premier Panoramic Ocean Views, 2 Lanai, 2BD/2BA, W/D
** OCT '25 dates: $250/night! (5 night minimum).This beautifully remodeled and spacious second-floor condominium on the Coconut Coast is one of the few units at Kaha Lani with two lanais and is also one of the closest units in the resort to the ocean. While staying at...
Kai Malie Calm Seas Beside still waters Psalm 23:2-3.
Welcome to Kai Malie, a wonderful vacation home! This comfortable home is located on the East side of the Big Island. Wake up grab your coffee and walk 10 minutes to 2 ocean front parks to watch the sunrise, and watch for whales! * NOTE If you are viewing this listing...
~Waikiki~ LOWEST RATES IN AREA ~ 3 Bedroom ~ Fully Furn ~ Blocks to Beach ~
We offer our Hale to you to enjoy the benefits of staying in one of the largest Apts. in our surrounding location, right in the Heart of Waikiki.Our large open floor plan is fabulous featuring a living/dining room combo. All 3 Bedroom apts. have a private lanai for your...
Charming Private Island Style Home w/Large Lanai, King Bed + Ocean View
If you're planning a vacation to East Hawaii, I'd like to welcome you to stay at the Koholā Hale "Whale House". This two bedroom, two full bath vacation home offers a South East Asian decor with furnishings sure to please.Located on a street that fronts the ocean, this...
Oceanfront oasis! VI809 - Sullivan Properties
Remodeled and ocean front on Kahana Bay. Fresh paint, carpet, restyled & updated decor make this 8th floor1 bedroom a treat for discerning vacationer. Watch movies on the 32" flat screen TV in the ocean front living room. The bedroom has a 26" flat screen. The tiled &...
Stylish Waikiki Gem with Ocean View and Free Parking!
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...
AKH C302 Whale Watching at 2BD Kihei Condo w AC Pool
Kihei Akahi C302 Spacious and Clean 2Bedroom Condo to Experience South Maui Breezes From Private Lanai with AC and Pool for Next Family Tropical Vacation FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*:...
Breathtaking Oceanfront Resort, 4 pools, 2 Jacuzzis and Restaurants on Site
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Studio unit with a king size bed, chaise lounge (suitable for a child ages 5-10) and air conditioning. Access to Kauai Beach Resort amenities. Views of beautiful green park and...
Maui Resort Rentals: Luana Garden Villas 8A – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
A premier offering within Enclave Two, Luana 8A is a highly sought-after and luxurious 3BR/3BA villa featuring private access and exceptional comfort. This prime ground-floor residence enjoys a quiet, secluded setting, while its north-facing orientation provides a cool,...
Luxury Oceanfront - NEW AC THROUGHOUT - Top Floor Remodeled- Island Sands #608
With the ocean just a stones throw away, you will be amazed by the spectacular breathtaking panoramic views! Immaculate and upgraded this spacious 989 sf 2 bedroom, 2 bath, oceanfront condo is your oasis in paradise. Master bedroom and living room offer direct...
Beautiful Condo, Private Lanai, Near Wailea Beaches
Address for this Condo: Grand Champions, 155 Wailea Ike Pl #5, Kihei HI 96753***Professionally Cleaned Condo, No-contact Check-In/Check Out*** Welcome to your beautiful island getaway at the luxurious Grand Champions Unit #5. This spacious condo has an open great room...
Grand Champions Villas 156 - Ocean & Golf Course View, King Size Bed
We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next...
Kailua-Kona Oceanview - Golf Course - Keauhou Bay
Keauhou Akahi is a small complex near the village of Kailua-Kona on the Big Island of Hawaii. This one bedroom suite, third floor condo has a beautiful ocean view and overlooks the ninth tee of the Kona Country Club. Keauhou Bay, which is home to evening manta ray...
Ocean View Remodel I Kauhale Makai 312
Enter this fully and beautifully remodeled 2 bedroom condo to see the sparkling ocean below from the living room sliding doors. The light and bright space has a modern coastal aesthetic with wood flooring throughout, brand new stainless steel appliances, walk in stone...
Poipu Shores 101A: So Close to the Ocean you can almost touch it!
Summary:True oceanfront living—so close you’ll hear the waves all day. Ground-floor condo with panoramic ocean views, private lanai, split-system A/C, and direct access to the oceanfront pool. Walk to Poipu Beach and Brennecke’s Beach, watch turtles and whales in...
Happy Place Bungalow, 2-Minutes to the Beach! TVNC #4339
Hanalei Happy Place Bungalow Permitted Vacation Rental Property - TVNC#4339Transient vacation rental is located in the tsunami evacuation zoneCharming bungalow studio with jungle views close to the beach!Nestled between the verdant mountains and golden beaches of...
A/C Luxury Poipu Beach Condo 506
Luxury & Lush surroundings await you at our Poipu Beach Condo! Nihi Kai#506Lani Kai Condo Rentals 1870 Hoone Road, Koloa, HI 96756 This newly-remodeled, 2-story, garden view, non-smoking condominium, has over 1200 interior sq. ft. as well as 4 private lanais. It's...
Kihei Maui Studio Condo king bed now available bottom floor *1
Tax ID: TA/GE 075-576-7296-01 Complete Remodel in 2023. Our rental is spacious Studio condo. One of the nicest and best locations at the Kihei Bay Surf. Central bottom unit with tennis court garden view, quiet first floor location away from the street, and fully...
Oceanfront Kihei
Adjacent to the Pacific Whale Sanctuary, this newly renovated 2-bed, 2-bath oceanfront rental is a modern oasis. Located on the 2nd floor, overlooking a heated pool with sweeping ocean, sunset, island, and mountain views. Just steps away to a protected ancient Hawaiian...
Napili Oceanview Luxury Home – Elevated Maui Living with Panoramic Views
UPDATE: The house, the views from the house, and the surrounding area (Napili) have not been damaged by the wildfires in Lahaina Town that occurred in Aug. 2023. The house is far enough (6.4 miles) from the nearest wildfire. Utilities in Napili are fine. The house is...
Awesome Ocean/Sunset Views
Escape to the peaceful shores of North Kohala, at the edge of Upolu Point, where the beauty of the Big Island meets the vast Pacific Ocean. Awhalecrossing Cabin is a hidden gem, offering a private oceanview getaway on a secluded coastline. This cozy, charming cabin...
Walkable to pier, restaurants and shops! A/C, W/D, pool views and parking!
Enjoy living downtown Kona, within walking distance to swimming at the pier or sipping an ice cold latte at a local cafe. There are yoga studios, bars, places to dance and churches for worship. You will feel at home with a fully stocked kitchen including a stove, oven,...
GORGEOUS REMODEL-CLOSE TO THE BEACH-WELL EQUIPPED-OCEAN VIEWS-AC
Book with confidence, this stunning newly remodeled, 3 bedroom, 2 bathroom spacious condo. Located in a premier location within Kamaole Sands, this condo has a rare, large floor plan (the largest condo at Kamaole Sands, 1625 sq ft) with ocean views, and is very close to...
KAN 211 Remodeled OceanFront 2BD for Whale Watching w Pool
Kanai A Nalu 211 Spectacular Remodeled OceanFront 2Bedroom with Ocean Views of Maalaea Bay. Idyllic Front Row Sunsets and Whale Watching. Year Round Pool REE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*:...
May Special! 4 Bed/4 Bath Kama'aina-Style Home across the street from Napili Bay
Locally owned and operated property, in business since 2013. County of Maui Vacation Rental Permit Number: STWM 2017/0006, TMK: 2430020770001 (TA) Registration Number: TA-155-824-1280-01. Napili Hale: Kama'aina GemPositioned in the heart of Napili, fronting Lower...
Maui Resort Rentals: The Whaler 701 - Oceanfront 7th Floor 1BR/2A, Sweeping Ocean Views from Lanai to Black Rock and Beyond!
Boasting an epic 7th-floor oceanfront location in the heart of Kaanapali Beach, Suite 701 delivers jaw-dropping ocean views stretching from Lanai to Molokai to Black Rock and beyond!The expansive 940+ sq ft interior of the suite features one primary bedroom and two full...
Spec Summer rates! Completely Remodeled with Upscale touches!
Kaleialoha #207Maui is open and ready for tourists! West Maui Welcomes You Back!. Our communities of Kaanapali, Honokowai, Kahana, Napili, and Kapalua; we all welcome you. Please have compassion and malama (care for) the island during your visit. Completely remodeled...
❤️PiH❤️ Starry Nights ★ Resort Pool & Waterslide Pass ★ Bikes ★ Beach Gear
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest elegant home, Starry Nights, in our Hawaiian Luxury Collection. Starry Nights is a wonderful new large single level 4 bedroom, 3 bathroom home. This home is an amazing family retreat in the...
Oceanfront Unit in a Gorgeous Tropical Complex with Beachfront Pool
The Address to Waiohuli Beach Hale #D218: 49 W Lipoa St. #D218, Kihei HI 96753.*Professionally Cleaned Condo, No-Contact Check-In/Check Out* Welcome To Waiohuli Beach Hale #D218! This is a beautiful 1 Bedroom unit in a stunning tropical complex fronting the Pacific...
Beautiful Waikiki Ocean/Sunset View! Pool, Kitchen
Ilikai #1629 – 1777 Ala Moana Blvd.The beautiful marina and ocean views from this contemporary 16th floor studio at The Ilikai, made famous in the opening credits of the original Hawaii Five-O, will remind you that you're on vacation in one of the most beautiful places...
Upgraded lush garden ground floor condo
Kamaole Sands 2-106 is a 1-bedroom, 2-bathroom condo featuring a window air-conditioner, a private washer/dryer, and a ground-floor lanai. Located on the ground floor, this unit can accommodate up to 4 guests with a King-size bed in the bedroom and a Queen sleeper sofa...
Banyan Harbor #F71, Walk to Beach, Wifi, AC, Pool, Parking, Laundry
Banyan Harbor #F71 – Kauai Vacation Rental, Lihue, Hawaii. Centrally Located on Kauai. Accommodates up to 5 guests, including children and infantsExperience the beauty of Kauai from this newly furnished, top-floor 2-bedroom, 1.5-bath condo at Banyan Harbor. Located just...
Oceanfront/Beach Condo KR101-South Maui With Dramatic Views - Steps to Pool
Experience the ultimate tropical getaway at Beachfront Kealia #101. This charming garden-level condo offers more than just stunning ocean views - it provides a comfortable and tranquil oasis for your Maui vacation. The fully equipped kitchen boasts unique features and...
Quaint Tropical Cottage w/Pool, Lanai & AC, Walk to Beach: Lanikai Ohana Hale
Discover your private island retreat at Charming Cottage in Lanikai by Gather, a beautifully renovated 1-bedroom, 1-bath home surrounded by lush tropical gardens. Fully remodeled in 2021, this peaceful hideaway blends modern comfort with the timeless charm of Lanikai’s...
Hualalai Fairway Villa 110C ~ garden level ~ w/signature outdoor shower
This garden level 2 bedroom, 2 bath Fairway Villa overlooks the 15th Fairway of the Hualalai Golf Course with views of the ocean beyond. Located within the master-planned resort community of Hualalai, guests have the option of amenity use privileges at the Four Seasons...
FULLY REMODELED-GROUND FLOOR-2 BEDROOM-AC THROUGHOUT-METICULOUS CLEANING
Book with confidence, this completely remodeled 2 bedroom, 2 bathroom (1086 sq. ft) ground floor 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...
Ocean Front 3 BR, 1 level Condo. Pool, SPA, huge Lanai. Pickle Ball
This is a spacious (1300 square feet) ground level, three bedroom, two bathroom, ocean view condominium, in the very popular, upscale Makahuena Resort located in the center of Poipu. It's size and internal layout provides spacious comfort for as many as 8 but works...
(4324) Studio at Hanalei Bay Resort, Ocean view, Pool
Welcome to Hanalei Bay Resort unit 4324, a bright and beautiful top floor unit with sweeping views of Hanalei Bay and the surrounding Bali Hai Mountains. This lovely studio unit has 1 King size bed and bathroom with a shower to come home to after a day of exploring!...
NO 17.96% TAXES. Relax & Enjoy 3-3 Unobstructed Mountain Views. Pool Gym.
Welcome to this Kauai north shore 3 bed/3 bath SECOND floor condo. Beautifully furnished next to the golf course and walking path, with a five minute drive to Hanalei and beaches. 2 miles away at Princeville Ranch offering zipline tours, off-road adventures, horseback...
Upscale, ground-floor at Halii Kai w/AC, shared pools/hot tub, private W/D, gym
Halii Kai 18E - WaikoloaOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The best of island living awaits at this upscale three-bedroom, two-bath Halii Kai condo. Perks of your...
#220 Beautiful, Blissful, and Ready for You!
A LITTLE ABOUT THIS CONDO....Polynesian Shores 220 is more than a place to stay — it’s your front row seat to paradise. Imagine waking up to the golden glow of the Hawaiian sun, Molokai shimmering in the distance, and the soothing rhythm of waves welcoming you into the...
The Cliffs at Princeville #7302, Pristine Ocean-Bluff Views, Private Lanai
Cliffs Resort at Princeville Unit 7302, North Shore of Kauai Vacation Rentals. Ocean bluff, 2 Bedroom, 2 Bath Kauai vacation condo. Accommodates up to 6 guests, including children and infantsThe Cliffs at Princeville sits on 22 lush acres of ocean-bluff, tropical...
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanfront Gem, Over 3600 combined Sq. Ft. w/ Built-in Viking BBQ!.
Perfectly suited to larger groups or families, this 5 bedroom gem combines one of our very finest 3BR oceanfront "Ali'i" residences with one of our very finest 2BR oceanview suites located directly next door.The generous combined 3300 sq ft square foot of interior...
DISCOUNTED RATES! 204 Beautiful oceanfront 1 bed/bath, 2nd floor condo
I learned about the Kulakane 25 years ago and decided to stay here with my brother. Also, my wife and I had visited the Kulakane and fell in love with it so much that we bought a condo the following year. Some of the same traditions that were enjoyed 25 years ago still...
MRR Presents Kaanapali Ali'i 286 - Expansive 2BR Corner Remodel w/ Gorgeous Mountain Views!
Boasting gorgeous views of the majestic West Maui Mountains and the Kaanapali Royal Golf Course from its 8th-floor vantage point, suite 286 offers a highly sought-after corner location with a luxuriously remodeled interior. Enjoy gorgeous panoramic views of the tropical...
KKSR#58 INCREDIBLE REMODELED TOWNHOME, OCEANVIEW, AIR CONDITIONING
Keauhou Kona Surf & Racquet Club, Townhome#58 is an incredible 2 bedroom, 2 bathroom Townhome that Knutson & Associates is extremely proud to be representing. This absolutely stunning townhome is immaculate, remodeled and a Guest Favorite! Upon walking in on the main...
Quiet Complex Two Bedroom Condo, Ocean views, King Bed, Private, Ocean Front.
Welcome to your dream vacation destination on beautiful Maui! This stunning rental property offers breathtaking unobstructed ocean views, modern amenities, and the ultimate in relaxation and comfort.Property Highlights: • Location: Nestled on the pristine shores of...
OCEANFRONT CONDO - Last Minute Availability! Kihei Sands Beachfront Condos-A8
Whether you're seeking a serene retreat or an island adventure, this is the season to indulge in Maui's unmatched beauty - made even more accessible with our special NEW WINTER OFFERS!Condo A8 is a highly desirable OCEANFRONT 1-bedroom, (sleeps 2) ground floor home at...
Amazing views w/ private pool and hot tub. Walk to 1 Hotel Hanalei Bay
A tropical paradise with stunning sea, mountain and valley views, of rainbows and flowers, gorgeous gardens , pool and brand new hot tub - all from the opulent luxury of a spectacularly designed and decorated contemporary 3500 square foot home less than 1/4 mile to the...