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.
Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218
ALOHA AND WELCOME TO HALE KAI # 218 Located right on the ocean on the beautiful island of Maui, our condo can be your _home by the sea_. Comfortably decorated with tropical Hawaiian furniture and artwork, our unit will provide you with all the comforts of home,...
Kona Bali Kai 411, Oceanfront, Two bathroom
Welcome to Bali Kai 411, an oceanfront condo offering a peaceful retreat with panoramic views of the Pacific Ocean. Located on the beautiful Big Island of Hawaii, this spacious 2-bedroom, 2-bathroom unit is the ideal getaway for families, couples, or small groups...
Kahala 621 by Destination Kauai - 1BD, Walk To Beach, Portable A/C
E Komo Mai — Welcome to Kahala 621!Located in the premier Poipu Kai Resort on Kauai's sunny south shore, Kahala 621 offers distant ocean views and lush tropical landscaping. Just steps from a scenic greenbelt walking path and minutes from popular beaches like...
Hilton Pool Pass for 2025 and Golf Discounts. Waikoloa Beach Villas C4
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas C4Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: One Queen BedGuest Bedroom Downstairs: One Queen BedAdditional...
Kahana Village #28 Beach Front Deluxe
Located out on the point at the Kahana Village Resort, our 2 Bedroom 2 Bath condo is 1200 sq feet, completely remodeled and very well appointed. We are just steps from the waters edge and enjoy sunset views in between the island of Lanai & Molokai. Our fully equipped...
Pali Ke Kua 12, Upgraded Hawaiiana Princeville Condo with A/C
Welcome to Pali Ke Kua #12, PrincevillePali Ke Kua #12 is a 2 bedroom/2 bath condo, located in a park-like setting on the tropical grounds of the Pali Ke Kua complex in the residential and prestigious resort community of Princeville.Open the sliding glass doors in the...
Absolute Amazing View, One level, 2 Lanai’s,New bed types King,Queen,Twin Qsofa
Guests are sure to enjoy a memorable vacation in this fully furnished, 2 bedroom/2 bath condo. The master bedroom has a King size bed. The 2nd bedroom is furnished with a Queen size bed and a Twin size bed. There is a Queen pull out sofa sleeper bed in the living room....
Aloha Condos, Na Hale O Keauhou, Townhome J-2, Ocean View, AC
Enjoy expansive ocean and golf course views from both upper and lower lanais and famous Kona sunsets right in front the upper lanai. Designer furnishings, Pacific Rim antiques and tropical décor. Original local artist works. The fully equipped gourmet kitchen will...
Hale Makai at Diamond Head – Oceanfront Estate
Ideally positioned along Honolulu’s prestigious Gold Coast with Diamond Head Crater as its backdrop, Hale Makai at Diamond Head is a licensed nightly oceanfront rental (NUC 90/TVU-0390) offering luxury, privacy, and the rhythm of true island life—just three miles...
Peaceful & Elegant Treetop Hideaway in Volcano Village
Set on a quiet street in historic Volcano Village, Hiʻiaka Guesthouse is a private, romantic pied-à-terre on the second floor of a beautiful 2-story custom home. Surrounded by old-growth ʻōhiʻa forest, and overlooking a lush and peaceful garden, the guesthouse...
Kona Ocean View: Beautifully Furnished, Amazing View, White Sands Beach
Great location within the White Sands complex--front building, top floor. Partial ocean view. Steps away from Magic Sands Beach, close to the best snorkeling in the area, and convenient to downtown Kona and area attractions. White Sands complex has all you need with...
Palms 306 Ocean Views, 5 Star Reviews: Remodeled
AMAZING 2 BEDROOM 2 BATH CONDO IN POPULAR PALMS AT WAILEA. SLEEPS UP TO 6 PERSONS. Largest 2 bedroom in area.This two-bedroom villa boasts stunning ocean vistas and a tranquil setting within Wailea’s resort community. With a full kitchen, comfortable living space, and...
Beachy Boho Retreat in the Heart of Kihei – Steps to Beach!
Ready to get away from it all? Say aloha to this beautiful beach side retreat in easygoing Kihei, ready for you and your guests to enjoy the fun, sun and experience why ‘Maui no ka ?oi’! Just across the street from the beach, this 2 bedroom, 2 bath condo sleeps up...
Lymans Bay Hale: Ocean View Surfer's Paradise with Hot Tub & Game Room
Right off Ali’i Drive in Kailua-Kona, Lymans Bay Hale is a spacious three-story, 5-bedroom, 3.5-bath home designed for ocean lovers and family gatherings. With sweeping ocean, beach, and mountain views, a game room, and a hot tub framed by tropical gardens, this...
Ko Olina Beach Villas O822: Elegant Retreat, Lagoon Views, Spacious Lanai
Welcome to Ko Olina Beach Villas O822 by Gather where luxury meets the serene beauty of Hawaii. Situated in the Ocean Tower at Ko Olina Resort, this villa is a stone's throw away from a well-groomed lagoon, offering guests an intimate connection with nature's wonders,...
Maui Resort Rentals: Honua Kai Konea 149 – Deluxe 3BR Ground Floor Interior, Huge Lawn Area!
Konea 149 is an expansive three-bedroom deluxe ground floor residence offering the perfect opportunity to gather, reconnect, and celebrate. This exquisite three-bedroom suite offers an incredible location, the first unit back from the very front of the building. The...
BEAUTIFUL BREATH-TAKING Ocean and Sunset Views w/ AC, Upscale Furnishing, & Art.
Enjoy Breath-Taking Beautiful Ocean views w/ AC, Upscale Furnishing, & Art.Our spacious split level condo offers incredible and unobstructed ocean views. The private lanai is the perfect spot for true relaxation, listening to the sounds of the waves crashing against...
OCEANFRONT Condo. Steps from the water! KULEANA 622
Perfectly located between Kaanapali and Kapalua, this beautiful 1-bedroom, 1-bath oceanfront condo at the highly sought-after Kuleana Resort offers guests the ultimate Maui getaway. Situated on the 3rd floor, this unit delivers breathtaking panoramic ocean views,...
Luxury 2bd villa with stunning views
Kapalua Bay Villa 28B 1&2 is a stunning 2-bedroom, 3-bathroom retreat that offers breathtaking ocean views, newly remodeled interiors, and access to top-notch amenities. This condo features a lanai that's ideal for relaxing, feeling the ocean breeze, and listening to...
Haleiwa Beachfront Condo. Perfect Peaceful Paradise!
E komo mai!Hawaiian for "Welcome" to the North Shore of O‘ahu. Make this one bedroom/two bath beachfront front condo your home away from home. In June 2019 the interior was completely remodeled: A beautiful kitchen; waterproof flooring throughout; smoothed ceilings,...
Family Friendly, Fully Furnished Villa In Ko Olina Resort near the Golf Course
Welcome to paradise! This beautiful Villa is nestled in the quiet neighborhood of Hillside Villa. You will love having breakfast ein your private lanai surrounded by palm trees and blue skies. This Villa has 3 bedrooms and can sleep up to six guests. This villa has 3...
Stunning, Oceanfront Deluxe Penthouse with Island Views - Sands of Kahana 282
🌺 Oceanfront Penthouse Paradise – Sands of Kahana Resort 🌊2 Bedroom • 2 Bathroom • 8th Floor • Sleeps 8 • AC • 1645 Sq FtWelcome to your dream Maui escape at the Sands of Kahana Penthouse, where breathtaking oceanfront views, stylish upgrades, and...
🏖️Beautiful Ocean Views | Top Floor | Concierge Included | vrKCV
vrKCV - Alii Villas 309, Professionally Managed by Kona Coast VacationsWelcome to Alii Villas 309, a top-floor, one-bedroom, one-bath unit offering stunning ocean views from both the lanai and living room. Whether you're sipping your morning coffee or relaxing after a...
Includes Mauna Lani Beach Club Pass. Fairways at Mauna Lani 2001
This vacation rental is professionally managed by ResorticaHawaiiFairways at Mauna Lani 2001. Includes Mauna Lani Beach Club PassSteps away from the pool. Private end unitPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest...
Kona-Keauhou Sunsets+Style! Full Kitchen, Washer/Dryer, WiFi, Lanai, DVD, TV Kanaloa 2106
Castle Kanaloa at Kona Resort #2106 - Relaxing is easy when listening to the sound of the waves from this cozy two-bedroom, two-bathroom ocean view suite. You’ll love how spacious this corner unit feels, with lots of room to sprawl out with family and friends.Enjoy...
Beautifully Remodeled 3bedrooms/2bathrooms
Aloha and Welcome to our newly remodeled stand-alone Cottage!Nestled hillside across from the Maui's Kahekili Beach, which was voted one of the world's Top 10 Beaches, and is also the winter playground of the humpback whales. Enjoy the spectacular views from your...
Welcome to Hokulani 622, 2 bedroom 2bath Rainbow & Mountain Views great rates
Make wonderful memories in paradise with this beautiful 2 bedroom/2 bathroom suite located on the 6th floor of the Hokulani tower at Honua Kai, boasting gorgeous rainbow and west Maui Mountain views. Honua Kai remains one of the top 10 luxury resorts on Maui. The...
Amazing Oceanfront Penthouse 🌊 with Stunning Views From The Lanai! 🏝️ Kona Bali Kai 419
Absolute oceanfront top floor condo with a big lanai (balcony) boasting an even bigger view. Located on the top floor of a four-story building, this oceanfront condo boasts first class views as well as excellent proximity to Kona Town and all activities. Whales, surfers...
KONA MAKAI#2-201 CORNER REMODELED UNIT WITH ALL TILE. BREATHTAKING OCEAN VIEW
Kona Makai#2-201 is a fantastic option for your Hawaiian Vacation. The owners extensively updated the property with beautiful new furnishings, installed tile throughout the entire condo & have upgraded the property with everything any guest may need.This beautiful 2nd...
North Shore Oahu Beachfront Condo, 2BR / 2BA
This fully equipped, ocean front, condo unit is located in Waialua on the beautiful north shore of Oahu. The minimum stay is 30 days at a rate of $185 per day or $5,550.The mountain side master bedroom features a queen size, comfort foam pillow top bed, full on-suite...
Quiet privacy with sensational ocean and coastal vistas!
Property Highlights • Five minute walk from three world-class beaches, including Kapalua® Bay, rated the #1 beach in the world by Dr. Beach, and #1 beach in the US by Conde Nast • The very best in affordable luxury living • Sensational ocean and coastal views,...
Remodeled, ground-floor home w/ beach access, shared pool & hot tub, & A/C
Kolea Kai 16DOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This incredible ground-floor condo is the perfect place to call home for your Waikoloa vacation. You'll love grilling...
Breathtaking ocean views from beautifully renovated condo on secluded beach in Kahana
This fully renovated, two-story condo with spectacular ocean views can be the perfect base for your West Maui getaway! Located in Kahana Outrigger, unit 4B1 lives like a home. Enjoy sunsets from your lanai, living room, and kitchen. The small complex has a shared pool...
Sugar Beach Resort - Ocean View, (Off Season Special Rates)
Beach Front Sugar Beach Resort, Ground Floor, Ocean View Unit. We recently remodeled this unit and it now represents outstanding quality. Enjoy all of the amenities in a clean, well kept property. The entire complex sits ocean front, there are no roads to cross, you are...
404 - Gorgeous remodeled oceanfront 1 bed/1.5 bath unit spectacular view!
This fourth floor oceanfront condo at the Kihei Surfside Resort is located on the sought after proximate ocean side of the building, and has a spectacular ocean view from the living room, dining area, lanai and kitchen areas. It is one of the larger one bedroom units...
Kona Alii#401 Beautiful 4th Flr corner condo w/ Elevators,INCREDIBLE LOCATION
Welcome to the listing page of our gorgeous Kona Alii, Unit#401! You are as close to the heart of Kona as it gets. Enjoy Hawaiian Living just above the excitement of Alii Drive. This complex is directly across from the ocean & the unit is recently renovated. A beautiful...
Kapili 52 Oceanfront Condo
Welcome to Koolkondo.com where you will experience luxury vacation rentals at its finest. Our stylish boutique hotel style condos and homes have it all. You will absolutely enjoy your home away from home with VIP concierge style services in modern island luxury! Our...
Kahana Village #19 Beach Front Luxury
Enchanting, elegant and romantic, Unit 19 is one of the most highly requested 3 bedroom beach houses at Kahana Village. We just remodeled our entire Unit with a brand new kitchen, new bathrooms and remodeled wet bar. Enjoy our new high-end Teak furniture out on the...
Reduced Rate at Private Tropical End Unit Townhouse w AC & Outdoor Lanai!
Absolutely the best location in Kauai with rare AC! Nestled next to the famous Princeville Makai Golf Course on the picturesque north side of the island, this beautiful end unit townhouse is close to all the natural beauty Kauai has to offer. Minutes from Hanalei Bay,...
Breathtaking Ocean View! 20% off Feb - Apr
Keep your eye open for last minute discounts!Relax with the whole family at this peaceful place to stay! Maui Sands is a low density property, a great location for a family vacation or a couples retreat. This upgraded condo sits directly over the ocean in the heart of...
Kuhio Shores #211 - Best Value Oceanfront Condo in Poipu!
This air conditioned two bedroom two bath oceanfront unit is on the second floor of Kuhio Shores condominium located in sunny Poipu, Kauai. Fronting a sandy bay this complex has as an elevator and offers some of the best surfing, body-boarding, swimming and snorkeling...
Upscale escape with pool, hot tub & grill - near beaches & water sports
Maui Kamaole H110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
🏖️Top Floor | Nice Ocean View | Close to Town | vrKCV🏖️
vrKCV - Sea Village 3311, Professionally Managed by Kona Coast VacationsSpectacular Top-Floor Condo with Unbeatable Ocean and Coastline Views!Welcome to your perfect getaway at Sea Village! This top-floor condo, perched directly above the pool, offers unparalleled ocean...
🏖️Spacious | Lagoon View | AC | WIFI | vrKCV
vrKCV - The Shores at Waikoloa 115, Professionally Managed by Kona Coast VacationsWelcome to Tranquil Shores at Waikoloa #115Discover ultimate relaxation in this spacious 2-bedroom, 2-bath condo with picturesque lagoon views, nestled in The Shores at Waikoloa Beach...
Paradise is Here! Big Ocean Views in newly remodeled luxury condo
Please read full description and acknowledge house rules before booking: Condo 1504. This 2 bedroom 2 bath is perfect for your stay on Maui. Enjoy the sweeping ocean views from the lanai with some of the worlds best sunsets! This is one of the ONLY condos on property...
nNew open concept Garden Delux Kiahuna, Partial Ocean View Retreat!
Celebrate Aloha and the tradition of Hawaii with a stay at our slice of paradise. You'll take a step back in time to a simple more relaxing period when you arrive at Kiahuna Plantation on the sunny south shore of the beautiful island of Kauai, 'The Garden Island'....
New Furnishings! Panoramic Ocean and Mount Makana Views
Pali Ke Kua 103 boasts unparalleled panoramic Hanalei Bay, Pacific Ocean, and Bali Hai Mountain sunset views from its oceanfront perch. The world-class views are said to be the most spectacular on the extraordinarily beautiful North Shore of Kauai and, many say, the...
Corner penthouse, oceanfront prime views! Great kitchen+bath.
Alii Kai 5301 occupies a prime top floor corner because you enter the building at the second floor level, you've got just 13 steps to climb to reach your door! Inside this updated Princeville condo you'll find elegant appointments and comfortable tropical furniture. The...
Luxurious Seaside Retreat ~ Heated Pool & Jacuzzi
Wow... this condo is truly AMAZING. This Top-Floor End Unit is Quiet & Private. Geared specifically towards Travelers who enjoy the FINEST ACCOMMODATIONS while Vacationing in PARADISE. Picture Perfect & once inside, it's the Lap of LUXURY. Enjoy the Trade Winds from...
Laniakea Beach House – Oceanfront Bliss on Oahu’s Turtle Beach
- Laniakea Beach House - NUC 90-TVU/0373 or 1990/NUC-2113- NUC Registered. Recently remodeled to reflect a stylish Hawaiian beach videUltra High Speed Internet Spacious and sunny family home on stunning “Turtle Beach” – Amenities include large deck, hot tub,...