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.
Unobstructed Panoramic Ocean View, Completely remodeled, Split system A/C
This ground-floor unit is located in a 15-unit building less than 80 feet from the ocean. Sit on the spacious lanai and watch dolphins and whales followed by breathtaking sunsets and an occasional 'Green Flash' through the palms.This condominium permits you to enjoy...
Grand Oceanfront Gated Estate on the Hamakua Coast
Experience the magic of this breathtaking oceanfront gated estate. Watch dolphins, whales, and cruise ships sail by. Feel the cooling Tradewinds where they first reach the Hawaiian Islands on your skin.Located in the heart of the Hamakua Coast, this is more than a place...
4 bedroom/ 3 bath luxury home with A/C, steps to community pool, oceanview
* Same 5 Star Holua Kai #9 (now under new management)* Central A/C * 4 bedrooms (3 rooms with kings and a double twin room) * Loft with queen Murphy bed* 3 full bathrooms with granite countertops* Backs up to golf course* Walk to Keauhou Bay* Ocean views* Directly...
Absolutely Oceanfront/ SimpleRuralHome/ AC rooms/ 30 day rental
**This home is offered as a monthly rental, however full month occupancy is not required. Please "Contact Host" to see if your dates are available.For the traveller seeking a more authentic experience of Hawai`i is Hale Makani Kai, "home of the gentle ocean breeze."...
Wailea Ekolu 310 - Molokini to West Maui Ocean View, Modern Renovation, Split AC
Welcome to Wailea Ekolu 310, experience breathtaking, panoramic ocean views from main living area and over-sized lanai of this spacious single level luxury condo, in the heart of Wailea and convenient to world class golf, tennis, restaurants and shopping. Sweeping and...
Honua Kai Resort- Konea 329 3 Bed, 3 Bath, Ocean Views
Konea #329 is one of the best locations in the resort. The third floor view provides beautiful views of the property, looking out over the landscaped grounds to the pools and Kaanapali Beach across Auau and Kalohi Channels to the island of Lanai.This unit faces the...
Direct Oceanfront Studio With Private Lanai
Enjoy spectacular unobstructed 180-degree views from our direct oceanfront vacation rental studio condo at the Valley Isle Resort, located directly on the beach in beautiful West Maui. Swim, snorkel, relax by the heated swimming pool or just enjoy the breathtaking...
"Magical View" oceanfront condo Lae Nani #521
2-Bedroom, 2-Bathroom Oceanfront Vacation Rental on Kauai with a Magical View! AC in Bedrooms Just Installed!E komo mai i kēia Lae Nani! Welcome to this beautiful point, a peaceful and lovely haven on the shores of Wailua, Kauaʻi.This second-floor condo is located in an...
Newly furnished house with mountain & waterfall views, balcony & washer/dryer
Hale Carly & Lia LaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beautiful views of the mountains and multiple spaces to come together make this newly updated and furnished home...
OCEAN VIEW 2 BED - 2 BATH Amazing Sunsets & WELL Stocked WITH Essentials
Nothing but rave reviews from our guests after a stay at our ocean view condo. Come enjoy the amazing picturesque sunsets at Kona Makai. Your dream vacation begins the moment you arrive. You can start and end your day on the large lanai overlooking the beautiful view....
Lowest fees you'll find-Coastal design-Amazing Value-2 Bedroom 2 Bath-Cold AC
Kahana Sunset C3 Welcomes you with much ALOHA....This unique condo is a beachfront property on the world-famous West Coast of Maui between Kaanapali and Kapalua. Kahana Sunset fronts one of Maui's most romantic white sandy beaches, nestled on protected Keonenui Bay,...
Large Princeville home with pool and jacuzzi on the Makai Golf Course
Located on the Makai Golf Course, this Princeville home is a large groups paradise. It features a pool, spa, ample indoor and outdoor space, two expansive decks, and a vast modern kitchen. With six bedrooms, including a bunk room, it’s well-suited for families with...
Ocean & Golf Views in Wailea - Designer 2 Story Condo w/ AC system, Wifi
The Address to Wailea Ekolu #314: 10 Wailea Ekolu Pl. #314 Kihei HI 96753*Professionally Cleaned Condo, No-Contact Check-In/Check Out*Location & luxury combine to make this Wailea Ekolu condo a perfect home away from home. Only minutes from Maui’s best beaches, high-end...
Remodeled 1BR Condo: Ocean Views + 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...
Maui Resort Rentals: Hokulani 820 – Top Floor 2BR w/ Ocean & Mountain Views + X L Balcony!
Hokulani 820 is a luxurious two-bedroom penthouse ocean view corner suite and one of the few offerings at Honua Kai that affords views of both scenes that Maui is famous for... the relaxing blue Pacific Ocean and the majestic West Maui Mountains. Further adding to the...
Spacious and Renovated Waikiki Condo With Full Kitchen and Ocean Views
Renovated, clean and spacious studio in Waikiki. Unit is on 38th floor of the Hawaiian Monarch Hotel/Condo building and comes with queen bed, full kitchen, full bath and amazing ocean, canal, diamond head and mountain range views. Walk to Waikiki beach, Waikiki strip,...
Waikoloa Colony Villas 204 Golfers Retreat with Gold Golf Membership Discount
Come see our newly remodeled 2 bedroom, 2 1/2 bath Waikoloa Colony Villas townhouse located off the 9th hole of the Waikoloa Beach Nine. Explore our Island of Hawaii, from Mauna Kea snow-capped mountain to Hawaii Volcanoes National Park where you can see how active...
Kaha Lani #304: Coconut Coast • Pacific Sunrise View • 1BR/1½B • Top Level View
Penthouse, 3rd floor walkup condo with magnificent ocean vista from your living room and large private lanai. Enjoy the quiet privacy of this intimate condominium on beautiful Kauai's Royal Coconut Coast. The quaint town of Kapa'a is a few miles North of the...
Hale Hapuna - Poipu's Best Ocean and Mountain Views
Whether you’re traveling with a large family or group of friends, Hale Hapuna is the perfect choice. It offers the ideal setting with approximately 5,000 square feet to spread out. Extra spacious living areas offer plenty of room to relax and enjoy each other’s company....
Kai Nui - Great Location and Value! Stylish 3br Home with A/C close to beach
Kai Nui is a stylish 2,800 sq. ft., 3 bedroom, 3 bath home located within the Lanai Villas section of the beautiful Poipu Kai Resort Community that was just refreshed in 2022! Located perfectly for those looking to walk to the beach or all of the other Poipu Kai...
Casa De Emdeko 210- 1/1 DELUXE SIZED UNIT,REMODELED, AC, OCEAN VIEW, ELEVATOR
This immaculately remodeled Deluxe 1 bedroom at the Casa De Emdeko is truly a Breathtaking Property.Located in the heart of Kailua-Kona, The Casa De Emdeko complex is a spectacular development that offers owners and guests the perfect blend of Hawaiian ambiance with...
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
“Kaihalulu” – Unit 105 – is an ocean view studio unit located ground floor in the Mauka (upper) building. There is a queen-size bed, a spacious covered lanai with a small dining table and comfy chairs and a great view. The unit has ceramic and laminate floors, wood...
Hokulani 108 at Honua Kai ~ Upgraded Ground Floor with Lawn & Easy Beach Access
You'll love this updated ground floor, one bedroom one bathroom condo with full access to the Honua Kai Resort's amenities. A spacious syn-grass lawn gives the kids plenty of room to play while you relax and enjoy the fresh ocean air. A short stroll takes you to one of...
2025 Waikoloa Hilton pool pass included 6 guests daily, available through 2025!
Waikoloa Beach Resort on the Big Island of Hawaii has so much to offer from comfort to convenience. This beautiful villa sits inside Waikoloa Beach Villas on the third floor right across from The Waikoloa Queen shops and King shops. Shopping and dining are within...
Honu O Kai (Turtle of the Sea): Lush Oceanview Getaway w/ Heated Pool AC Views
Honu O Kai (Turtle of the Sea) – Kailua Kona, HIA serene coastal retreat designed for family gatherings and relaxing getaways, Honu O Kai offers 2,928 sq. ft. of indoor-outdoor living space with panoramic ocean views and upscale amenities—all just moments from the...
Luxury Remodeled Ocean View Studio PAPAKEA C207
Stunning Ocean and pool view - Papakea Studio2 beautiful swimming pools, 2 ocean side cabanas and jetted spaPool side BBQs3 tennis courts & 2 putting greensNew AC split units throughout! Walking distance to stores and restaurantsShuffle board Papakea C207 has...
BIG ISLAND PLUMERIA COTTAGE New AC! Ideal Couples Getaway in Magical Puako!
Plumeria Cottage offers a vacation of ease indoors and out. Compact yet perfectly proportioned in the vintage beach style, it is a delightful combination of convenience and charm. And, with a roomy, sunny lanai and large shaded grassy yard, it becomes quite spacious. An...
Kona Makai - Ocean View! Gorgeous Sunsets! Beautiful Spacious Condo 2 Lanai’s
The Kona Makai complex is a beautifully maintained & highly sought after Ocean Front Complex located on famous Ali'i Drive, just 1.3 miles from Kona town. This wonderful complex features include, beautifully manicured tropical grounds, Saltwater ocean front pool and...
Hawaii Life Rentals - Kahana Ocean Front
Experience unparalleled oceanfront living in this stunning penthouse at the Valley Isle Resort, Kahana. Residence #804, offered by Hawaii Life Real Esatate Services, boasts breathtaking, unobstructed views of the Pacific Ocean, Molokai, and Lanai islands from every...
Kona Vacay at Keauhou Akahi - on the 9th tee overlooking historic Keauhou Bay.
Floor-to-ceiling windows in every room are open to the gentle ocean and mountain breezes in this bright, airy and beautifully appointed 2nd floor unit on the 9th tee of the Kona Country Club golf course overlooking tranquil Keauhou Bay in the heart of the Keauhou...
Makaha on the Beach-Back in Time =Direct Oceanfront & Cove
Only 4 openings in 2026, June, August, September & October available 30 night minimum2027- sold out2028- 2 openings July 15th- August 23rd & October 2029-Located on a Golden Sandy Beach Cove, we are direct Ocean & Cove front. A rare find, one of the few where sea...
EXQUISITE REMODEL-SLEEPS 8-WELL EQUIPPED-AC-METICULOUS CLEANING
Book with confidence, this stunning, 2 bedroom, 2 bathroom spacious condo that has been completely remodeled from top to bottom. 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...
$149 a night Book Now. Pool and Ocean at Your Doorstep Unit #123
Welcome to Waiohuli Beach Hale D-123, a stunning 1-bedroom, 1-bath condo located on the ground floor, right next to the pool of this oceanfront paradise. Please contact us for seasonal discounts and special rates! This NON-SMOKING PROPERTY offers a perfect blend of...
Stunning retreat w/ a full kitchen, gas fireplace, furnished lanais, & free WiFi
Pele Noe - 3 Miles From Volcanoes National ParkOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled into a native Ohia Lehua forest, this Big Island vacation rental is...
Cool, Lo-Fi Styled Surf Shack - Ka Hale Nalu
Mid-century modern, Kauaian styled home provokes feelings of coziness, nostalgia and a spirit of adventure. Honoring the 60's Hawaii of craftsmanship, hand-made furniture, art and linens, this uniquely, beautifully curated home will embrace you with Aloha. Relax...
Aloha Condos, Kona Reef, Condo F-26, Ocean View, AC
Escape to tropical paradise at this 1-bedroom,1-bathroom Kailua-Kona vacation rental condo which is located in walking distance to Kailua town. ! Sleeping up to 2 guests, this fully furnished home boasts an ideal oceanfront location along with resort features including...
Hale Koolau Treehouse, Charming Getaway TVR #1018
Hale Ko'olau Treehouse, Haena Permitted Vacation Rental Property - Permit ID: TVNCU #1018Transient vacation rental is located in the tsunami evacuation zoneCanopied in tropical foliage is Hale Ko'olau Treehouse. Vacation like you’re living among the treetops in a...
Spacious and comfortable - Extended Stays Welcome
This airy top floor condo has been lovingly furnished to complement the unit's high vaulted ceilings and the big sky views of Mauna Kea. Not all 2 bedrooms at the Fairways are the same! Top floor units have high ceilings and the "Resort" floor plan offers an additional...
🏖️OCEAN FRONT | WIFI | Free Concerige | vrKCV🏖️
vrKCV - Sea Village 4312, Professionally Managed by Kona Coast VacationsCharming Oceanfront Condo with 180-Degree Views of Kailua Bay!Experience the ultimate oceanfront escape in this spectacular top-floor condo, offering breathtaking 180-degree views of the Pacific....
Cottage #2
Cottage #2 offers a luxurious two-bedroom retreat in the enchanting Haena area on Kauai's North Shore. Perfect for families or groups of friends, the cottage features two king-size bedrooms, a fully equipped kitchen, and a deck with breathtaking ocean views.Situated on...
Tropical garden bungalow - all the comforts
Honey House is a finely finished piece of craftsmanship. Easy access, no stairs. It is a stand-alone 480 square foot garden bungalow. Hardwoods accent the living area. The full bath features a tiled shower, granite counter, and access to a garden lanai. We feature whole...
OCEAN FRONT! STUNNING OCEAN VIEWS FROM EVERY ROOM IN THIS 2BR 2BA CONDO
Our 2 Bedroom 2 Bathroom Ali'i Kai 1 Condo offers one of the best ocean front views in Princeville from almost every window. It affords you a 180 degree ocean view so you can wake up to the sight and sound of the sea without even having to leave your bed! Almost feels...
Mana Kai 607 Great Ocean Views, Best Beach on Maui
Mana Kai Condo 607 has everything you are looking for! Best Beach... it's right on it! Unbelievable Ocean View... that's what you'll have at the Mana Kai.The Mana Kai Resort is located right on one of the nicest beaches on Maui, Keawakapu Beach. The sand is luxurious...
Beautiful Private Ocean Front Home on Lyman's Bay An enjoyable and peaceful stay
Beautiful Private Ocean Front Home On Lyman's Bay. This home is beautiful beyond description. Located on one of Kona's most beautiful bays and most popular surf spots. The views are spectacular and with the ocean only 20' away from your private Lanai's you need to be...
3 Story Ocean Luxury House - Sleeps 16+ Whole House - steps to the Beach-Shore!
Welcome to Hale Mauna & Moana! (House of Mountain & Ocean) This 3 Story house is steps to beach-shore access. Listen to the sounds of the ocean and enjoy ocean views from the second and third-floor rooms and lanais! Boasting over 4,000 finished square feet. Living in...
Kahana Villas: Oceanview 2BR Condo w/ AC & Pool
This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances.Oceanfront Oasis – Wraparound Lanai, Chef's Kitchen & Resort Pools Hoʻokipa (hospitality) welcomes you to a luxurious retreat on the serene shores of West Maui. Perched...
#105 Seaside Serenity with Comfort
A LITTLE ABOUT THIS CONDO....Polynesian Shores 105: Your Maui Retreat Welcome to Polynesian Shores 105—a cozy ground-level condo designed for comfort and tropical charm. Perfect for up to four guests, it features a king-sized bed, a queen sleeper sofa, and a handy desk...
RESORT LIVING AT IT'S BEST! GORGOUS DIRECT BEACHFRONT CONDO IN KA'ANAPALI!
MAUI KA'ANAPALI VILLAS (MKV) is known for having many repeat guests that come back year after year! This PRIME beachfront property, is situated between the famous " Black Rock" and Kahekili Beach Park which is also known as Airport Beach.ABOUT THE CONDO...This well...
Deluxe Room w/King Bd, Ocean/Pool views, New Furnishings!, No Resort Fee
Kauai Beach Resort is a 4 Star Hotel property located on the Ocean. My unit is a privately owned room with great views. The view is of the swimming pools and the Pacific Ocean beyond.The amenities at this Boutique Resort include multiple large swimming pools and...
Beautiful 2/2 Townhouse in Princeville, Free WiFi, Cable TV, BBQ, beach gear
1300 ft2, very spacious townhouse, two bedrooms with a king size bed in the open loft-style master bedroom and queen size in the downstairs bedroom. Immerse yourself in the magic of Kauai through this conveniently located townhouse in the heart of the Master Planned...