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.
Hale Mana: Luxury 5 BR Kilauea Estate with Pool & Hot Tub
Welcome to Hale Mana, one of Kauai's most beautiful island treasures. This stunning three-acre private estate will bathe you in every luxury with its beautifully appointed amenities, secluded beach, and tremendous ocean views.If you are looking for Hawaii's best...
A Piece of Paradise at The Beach Villas in Ko Olina 2 Bedroom 2 Bath
Aloha and welcome to the Beach Villas at Ko Olina!The Beach Villas at Ko Olina are in the World-Famous Ko Olina Resort and Marina on the second of the four spectacular lagoons. You’ll enjoy the mile-and-a-half walkway along the lagoons, passing the Four Seasons...
Three Bedroom Villa at The Beach Villas at Ko' Olina
* Book with confidence! This vacation rental is a LEGAL Oahu vacation Rental Operating in a Resort Zoned District and is not affected by passage of Bill 89. This Luxury Condo is a spacious and beautiful 3 bedroom, 3 bath, professionally decorated Villa with a beautiful...
Beautiful home in Kailua-Kona with easy access to all the Island.
Our 3 bedroom 2 bath vacation house is conveniently located just 5 minutes from Kailua-Kona town and its many shops, restaurants and grocery stores. You are just 10-15 minutes from many of Kona's most popular beaches, snorkel spots and activities. Only 15 minutes from...
Stunning KoOlina Kai 2BR/2BA Condo sleeps 4
This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. This property has a mandatory 30 day minimum. This property may not be rented for less than 30 consecutive days. Rental prices will...
Oceanfront condo with resort amenities, stunning views, and top-notch comfort
Ali'i Cove Y1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience luxury living in this stunning condo located in the exclusive Ali'i Cove Condominium complex in Kailua-Kona,...
Puna Rainforest Retreat Hotspring - Blue Ginger Cottage
Puna Rainforest Retreat Blue Ginger Cottage has a complete kitchen with all the amenities, a full bathroom and cozy queen size bed. Perfect for couples. This colorful cottage is clean, comfortable and affordable! Enjoy the rainforest trail, steam vents, plunge pool,...
Oceanfront, Split A/C, incredible sunsets, king bed, remodeled October 2023
• Oceanfront• Split A/C units• King bed• Remolded Oct 2023• Beach access from condo complexFully remodeled in October 2023, this custom built, detailed, upscale condo 209 welcomes you. You will find this bright, beautiful one bedroom, one bathroom oceanfront...
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unobstructed ocean view corridors, privacy, convenient access to the Wailea Beach Path, and one of the world’s best beaches as the front yard....
Ka Hale Kealoha A215
Welcome to Molokai Shores luxury condo Ka Hale Kealoha A215! This beautifully updated (and freshly painted Sept 2021!!) 526 sq ft condo boasts high end appliances as well as a fully equipped kitchen with everything you would ever need. Sleeps 4 in a brand new (9-2021)...
Prince Kuhio 110 - Ground Floor Portable AC
PRINCE KUHIO 110 AT KOLOA KAI VACATION RENTALSA Romantic Escape on Kauai’s Sunny South ShoreDiscover the charm of Prince Kuhio 110, a recently remodeled one-bedroom condo offering a cozy and modern retreat for couples. Located on the ground floor with easy access to...
Fully Remodeled Hanalei Bay Villa #34 w/ Amazing Views!
Hanalei Bay Villas are located on a bluff with incredible mountain and ocean views and just a short walk away from the new 1 Hanalei Bay Hotel. Villa #34 has been completely remodeled and designed in cool neutral tones with a clean modern vibe. All new, high end...
Aolani House+ Cottage | #1 AirBnb on Big Island | Condé Nast
Aolani House & Coffee Cottage – Your Private Hawaiian SanctuaryNestled in the serene coffee farms of Holualoa, Aolani House & Coffee Cottage offers an exclusive retreat for relaxation and rejuvenation. Perched on 5 private acres of Kona Coffee and Macadamia Nut farms,...
Open-concept and modern decor with ocean views
Nestled within the breathtaking Kapalua Bay this exquisite 1-bedroom, 1.5-bathroom villa that can accommodate up to 4 guests, effortlessly combines modern comfort, breathtaking ocean views, and practical amenities for a truly unforgettable vacation experience. Kapalua...
Island Sunset Villa: Upcountry Maui Home in Kula
Welcome to Island Sunset Villa, where modern luxury meets nature’s finest. This tranquil eco-friendly home is nestled on 2 acres of lush, organic orchard, offering the perfect blend of seclusion and convenience. Step inside this architectural gem, where walls of...
Steps to Maui's Charley Young Beach, Condo Apt #8
Make yourself at home in this lovely 1-bedroom Kihei retreat. This cozy condo offers a beautiful living room with a private lanai to enjoy the sunrise or sunset, free use of washers and dryers onsite, and AC to keep you cool. Stay connected with WiFi and enjoy the...
Maui Resort Rentals: Kaanapali Ali'i – 6 Total Bedrooms, Luxuriously Remodeled, Premiere Ocean AND West Maui Mountain Views!
This phenomenal six-bedroom offering brings together a 2BR suite with a premier ocean view in one of the best interior stacks at the entire resort and two luxurious neighboring 2BR partial ocean view suites. Together the three 7th-floor suites offer a combined 4600+ sq...
Ke Aloha Estate - North Shore Kauai Retreat with Pool, Spa, Gym, Pool Table & Pickleball
TVNC - 4267 - TA-105-498-4192-0124/7 On Island Contact - Kimmy, House of Dreams KauaiRates are based on 10 guests. There is an additional fee of $75 per night per person up to 14 guests. All reservations will require main guest to review and sign a rental agreement for...
Newly Renovated Second Floor North Shore Princeville CondonMaster Bedroom & Loft
This Air Conditioned, newly renovated, spacious 1 BdRm condo with Primary Bedroom and Full Bathroom plus Loft with half Bath is located in the Resort Community of Princeville. New Novaform Comfortgrande King Size Bed in the Primary Bedroom and Queen Size Bed with half...
Waterfalls, Palm Trees, and Hanalei Bay, Short walk to beaches and resorts
Awaken to views of waterfalls, palm trees and Hanalei Bay while the scent of jasmine wafts through your window on an island breeze. 3 king bedrooms all with en-suite dual vanity master baths. 1200 sqft lanai with private access from each bedroom. Relax to the sound of...
NEW !!! DIRECT OCEANFRONT nSUNSETS and crashing waves!Newly remodeled! GORGEOUS
**Boutique Beachfront Condo in Kona - Top Floor Studio**Welcome to the only beachfront condo complex in Kona! Renovated 11/2023 This top-floor studio (3rd floor-no elevator) offers the perfect Hawaiian retreat, just steps from the iconic Magic Sands Beach. Enjoy...
Charming 1-bedroom condo in awesome Kuilima, Kahuku, Oahu
Beautiful, gated Hawaiian-style condo. Steps to tennis courts and pools! Walk to the beach to surf, snorkel, sun bathe or people watch.Need more space for a wedding party ? Family Reunion?Neighbor units also available! This Kahuku condo boasts 1 inviting bedroom with a...
Beachfront Paradise on Sugar Beach - Kihei Beach Resort #408
Look no further, beautifull custom upgrades throughout, oceanfront condo directly on Sugar Beach, the longest stretch of sand Maui has to offer and just steps from your door. Start your morning off relaxing on the lanai listening to the waves while embracing the...
Aloha Condos, Kanaloa at Kona, Condo 1901, Oceanfront, AC
Unit 1901 in Kanaloa at Kona is a beautiful two-bedroom, two bathroom, groundfloor oceanfront condo with a fully equipped kitchen, TV in three rooms, ceiling fans throughout and air conditioning. • Oceanfront Location• Sunset Views Year Round• Quiet, Residential...
Beachside Penthouse ❀ Royal Mauian 604
Experience No. 604 at Royal Mauian, a comfy top-floor, air-conditioned beachfront sanctuary with breathtaking views. Nestled between two white sand beaches, enjoy the best of both worlds: dive into vibrant beach life or relax watching the ocean theater from your private...
2 Bedroom Condo-Princeville, Kauai-Family Friendly!
Perched above the sparkling waters of Hanalei Bay, this resort offers families a front-row seat to some of Princeville’s most awe-inspiring natural beauty—from the dramatic Na Pali Cliffs and iconic Bali Hai Mountain to cascading waterfalls, golden beaches, and palm...
Kamaole Sands 10-403 - Stunning Renovation - Penthouse Level - Split AC - Look!
Ocean and mountain views from this penthouse level two-bedroom, two-bath 1188 square foot condo in the highly desired building 10. Kamaole Sands 10-403 sits across the street from Kamaole III Beach Park in South Kihei, Maui. Enjoy the view from your large 166 SF lanai;...
2 Mi to Hawaii Volcanoes Nat'l Park: Tranquil Home
Furnished Gazebo | BBQ Ready | Near Hiking & GolfingDiscover breathtaking natural beauty with this Volcano vacation rental as your launching pad! Boasting peaceful surroundings and convenient proximity to Hawaii Volcanoes National Park, this 3-bedroom, 2-bath home makes...
Whaler at Kaanapali Beach Studio #164
Upgraded and Renovated Studio Garden View condo at the Whaler on Ka'anapali Beach. This spacious studio can sleep up to three people. There is a King bed and a Queen-size sofa bed. Located on the ground floor and a short walk to the beach. There is a 48-inch TV in the...
Ocean View Hanalei Bluff House With Pool
Discover Hanalei Bluff House located in Princeville overlooking the beautiful Hanalei Bay. This stunning newly constructed 3 bedroom 3.5 bath open concept house offers a salt water pool and the best of cool style and modern tropical living. Hanalei Bay, ocean, mountain,...
Wailea Beach Villas G302 - 3 Bedroom Ocean View Villa
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking...
AVAIL Thanksgiving 2025: BEACHFRONT Luxe. Swim with turtles! 4 bed/3 bath AC
This property is offered as a monthly rental, although full-month occupancy is not required, "Contact Host" to see if your dates are available.TURTLE POINT BEACH HOUSEWelcome to your secluded paradise! Our backyard has a sea wall in which you can step down onto the sand...
🏖️Ocean & Mountain Views | 2BR with Loft, 4 Beds | Relax in Luxury | vrKCV
vrKCV - Golf Villas at Mauna Lani H22, Professionally Managed by Kona Coast VacationsWelcome to your tranquil retreat at Mauna Lani's Golf Villas, perfectly situated along the ocean-facing side of the prestigious South championship golf course. This immaculate condo...
Breathtaking views of Kaanapali Beach, Black Rock and the island of Molokai.
Beautiful views of the world famous Kaanapali Beach and Black Rock from this 1 bedroom, 2 bath condominium. Sleeps 4. Seasonal watching of humpback whales, spectacular sunsets or enjoy your morning coffee or breakfast on your large lanai while the beach and blue ocean...
Hyatt Residence Club Ka'anapali Beach Resort - 2bd/2ba Ocean View
Available from Saturday, Jul. 5, 2025 (4pm check-in) to Saturday, Jul. 12, 2025 (10am checkout).Minimum 6 nights from Jul. 5, 2025Luxury fully-furnished, 2 bedroom 2 bathroom oceanfront unit in top tier Hyatt Residence Club located inside world class Hyatt Maui...
Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
PROPERTY SUMMARY:Serene and modern, this spacious 2 bedroom - 2 bath fully remodeled condo is conveniently located steps from an amazing selection of casual restaurants, fine dining, shopping and beach rentals, and all this directly across the street from both Kamaole...
Lio Ka Hale (The Horse House) - Kamuela, Hawaii - spectaular views of Mauna Kea
This destination home is in the seat of horse country in the beautiful town of Kamuela/Waimea. This A-frame challet home has spectacular views of Mauna Kea and the verdant green, rolling hills of paniolo (hawaiian cowboy) country. Cozy up to the wood burning stove on...
Kona Bali Kai 232 - Studio Condo with Beach Access
This studio condo offers the perfect getaway for two (or for solo travelers!) The space is equipped with everything you need for a comfy vacation, including a king bed, fully-stocked kitchen, and a dining space. You’ll also be right across the street from the ocean...
Keauhou Punahele | Condo in Kailua-Kona
Keauhou PunaheleOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This dreamy island condo is waiting to welcome you to a true slice of paradise. Wake each morning to the sounds of...
Book your Beach vacation, and stay at beautiful oceanview Kamaole Sands 2-206
Kamaole Sands 2-206 is set back from the road, making it quiet and private with a spacious open feel. It comfortably sleeps up to four guests. This spacious condo is 818 square feet, with beautiful tile plank flooring throughout. Unlike most owners at the Kamaole Sands,...
Kolea 1E - 3 Bedroom Oceanview Vacation Rental
Kolea 1E is located in the luxurious community of Kolea in Waikoloa Beach Resort. Its location within the complex gives you the easiest access to the Hilton Waikoloa, which guests of Waikoloa Vacation Rentals have access to. As you enter into the villa off of your...
1206 The Palms-Wailea. Owner Direct. Car available. The reviews say it all
Hyundai Santa Fe with room for five is made available to guests through Turo for $40-$60 a day. If you are interested, let us know.DIRECT TO ROOM CHECK-IN: At 1206 The Palms, you go directly to your private condo without ever needing to check in. The same is true upon...
❤️PiH❤️ MAUNA KEA BEACH ESCAPE ★ Ohana Suite ★ Pool & Spa
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Mauna Kea Beach Escape, a brand new exquisite 4 bedroom, 4 1/2 bath home located in Hapuna Estates within the Mauna Kea Resort. Prepare to embark on a truly remarkable escape where luxury, comfort, and natural...
Exceeding Expectations at Hale Aloha Kaloli~Air Conditioning Throughout the Home
Modern furnishings and recently updated with Air Conditioners in every room!! New Kitchen appliances makes meal prep a breeze. Private home is conveniently located 30 minutes from Hilo, 40 minutes from the newest beach in the world, and less than 50 minutes away from...
Romantic, Private Cottage Nestled Away in Volcano
This is a private cottage located in one of the prettiest parts of Volcano Village. This one bedroom cottage is perfect for honeymooners, a special anniversary, or as a writer or artist's retreat.Enjoy natural beauty and incredible privacy. Step out the front door and...
Luxury Gem at Kauai Beach Resort and Spa KBR 3122 - TWO QUEEN BEDS!
Enjoy a delightful beach vacation at Kauai Beach Resort and Spa, a full-service oceanfront resort situated on 25 lush acres along Kauai’s longest strolling beach. This is a privately owned, immaculate ground floor unit steps from the ocean and 4 salt water pools. The...
Maui Banyan F-103 Stunning 2 Bedroom Condo With AC
**Please note: This is a ground floor unit, although there are stairs down from the parking lot and another set of stairs down to the ground floor hallway. Everything in the unit has been upgraded! Floors, newly built walk-in showers in both bathrooms, new bathroom...
Honu Kai Villas 2 by Destination Kauai - A/C, Ocean Views, Stunning Sunsets
E Komo Mai, Welcome to Honu Kai Villas IIJust steps from the Pacific coastline, this multi-level updated villa boasts beautiful ocean views and stunning sunsets on Kauai's south shore. Morning strolls to watch the sea turtles and spinner dolphins are a must! Snorkel at...
Renee's Poipu Paradise! Oceanfront Views & A/C!
SPECTACULAR Oceanfront Views and A/C! Enjoy the sunrise, turtles and whales in season directly off your private lanai! Kauai's best snorkeling? A 5 minute walk to Lawai Beach. Kid-friendly beach? "Baby Beach" a 5 minute walk the other way. Surfing? 30 feet to the water...
Modern 2BR Condo | Pool & Sauna | Ala Moana
Stay in style at this brand-new 2BR/2BA condo in upscale SKY Ala Moana. Perfectly situated in Honolulu, this modern unit accommodates six guests with two queen beds and a pull-out sofa. Enjoy luxury amenities, including a year-round outdoor pool, sauna, and free garage...