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.
Kapalua Golf Villas 15P3-4: Garden View Condo w/ Pool, BBQ at Resort
Kapalua Golf Villas 15P3-4 by Gather is a beautifully remodeled luxury retreat overlooking the 10th fairway of the world-renowned Kapalua Bay Golf Course. With breathtaking ocean and golf course views, elegant upgrades throughout, and access to multiple resort pools,...
Great Rates and A/C in every room. Near North Shore beaches. Pool & Hot Tub!
Three bedroom, three bath luxury Villa located in Princeville, Kauai with A/C! Just steps from the Makai Golf Course Country Club. Includes two master suites with king-size beds. First master suite has a walk-in shower and TV. The second master suite includes private...
KRV 1011 New Listing 1BD Condo w Spectacular Kapalua Ocean Views at the Ridge
Kapalua Ridge Villas 1011 NEW LISTING Spectacular Kapalua Ocean Views from this 1Bedroom, 2Bathroom, Condo at the Ridge!Aloha from Kapalua Ridge Villas 1011 on beautiful Maui, where breathtaking ocean views and classic Hawaiian charm await you. Nestled in one of Maui s...
Garden Island Oasis - Regency 424 at Poipu Kai. 3 bedrooms - Walk to the beach!
Welcome to our island home! Discover the ultimate getaway at the Garden Island Oasis at the Regency at Poipu Kai, nestled in the heart of the enchanting Poipu Beach area on the south shore of Kauai. This beautiful property is renowned for its lush landscapes and...
*Lauloa 204* Maui Prime Oceanfront Condo, A/C!
This updated 2nd-floor condo offers breathtaking views of Maalaea Bay, the grand volcano Haleakala, and the sparkling Kihei lights at night from the private lanai! The primary suite features a comfy king bed and ensuite bathroom with a walk-in shower and a guest room...
Panoramic Oceanfront View, Condo with Air Conditioning and Large Lanai
Kuhio Shores #314. Floor to ceiling wrap around windows provide unobstructed panoramic ocean views! Our light, bright, spacious, and comfortable two bedroom-two bath Poipu Beach oceanfront vacation rental condo sits 40 feet from the ocean's edge. Floor to ceiling glass...
KBM Resorts | FREE CAR | Maui Kaanapali Villas | Beachfront Resort, Upgraded Studio! MKV-C152
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kanaloa at Kona 1606: Beautiful Oceanview Condo w/ Shared Pool, Spa, AC & Lanai
Welcome to Kanaloa at Kona 1606, a stylish 3-bedroom, 2-bathroom penthouse villa perched above the Keauhou Golf Course with panoramic fairway and ocean views. Featuring vaulted wood-beam ceilings, upgraded interiors, and resort-style amenities across 16 tropical acres,...
Beautifully decorated Penthouse overlooking WAIKOLOA Beach golf course
The location is perfect if you want to be walking distance to all the best shops and restaurants In WAIKOLOA beach resort. Our condo at the Fairway Villas is right across the street from one of the Big Island’s best beaches, Anaeho'omalu (aka A-bay). After a long day of...
Waipouli Beach Resort D105. A Spacious Condo with Lazy River and Top Shelf Restaurant Onsite.
Summary:Waipouli Beach Resort D105- A Spacious, Clean and Comfortable Condo. A Giant Pool with a Lazy River and Top Shelf Restaurant are Onsite.The Space:This Oceanfront Resort is a Dream and located on the Beach. Just Steps to the Warm Turquoise Ocean. The Kids and...
**Fantastic, Best Maui Location * REMODELED Condo
Elevate your island retreat with the allure of this enchanting second-floor condo, a sanctuary of serenity boasting breathtaking full ocean views. Recently remodeled to epitomize modern comfort and style, this one-bedroom, one-bath haven spans a generous 592 square...
NEW LISTING: Newly furnished with lovely decor. Experience our tropical paradise
NEW LISTING: Welcome to Kealohilani, our heavenly home by the sea and your ground floor tropical escape. Nestled a few steps from lush gardens and pristine pools, and a stone's throw from the island's most famous beaches, this getaway is a dream come true for those...
Relaxation at Its Finest: Beachfront 1bd/1ba Condo - Menehune Shores #517
Menehune Shores #517 – One-Bedroom Oceanfront Escape with Incredible ViewsWelcome to Menehune Shores #517, a bright and inviting one-bedroom condo that offers stunning panoramic views of the Pacific Ocean and Maui’s vibrant sunsets. Located on the 5th floor, this...
Gorgeous! The Waterfall Retreat At Reed's Island
ALOHA!The breathtaking Waterfall Retreat at Reed’s Island is a spectacular 4 bedroom, 3 bath home in the exclusive area of Reed’s Island in Hilo. The home is only a few minutes from downtown Hilo but it feels like a private paradise retreat with a stunning river and...
New! Hale Mehana, Beautiful North Shore Home, Princeville, Kauai
A tastefully updated North Shore Kaua’i vacation home located in beautiful Princeville. Conveniently located with easy access to the famous Hanalei Bay, Kilauea Lighthouse, Haena Beach Park, the breathtaking Napali Coast, shopping, dining, and more!• Indoor/outdoor...
Majestic Tropical Ko'olau Mountain views! Washlet!
Waikiki Sunset #2807 – 229 Paoakalani Ave.Savor fabulous mountain views by day and sparkling city lights at night from this 28th floor, one-bedroom condo (546 sqft plus access to lanai from bedroom with small table and chairs). Central AC, free Wi-Fi, Washlet! 4-person...
Unit #204-1BR+Mezzanine BR/2 Bath: 2 BR, 2 BA Condominium in Lahaina, Sleeps 4
Beautiful 2nd Floor Unit. Mezzanine bedroom with Queen bed, downstairs bedroom with with 1 King bed (can be made into 2 Twin beds upon request). Nearly 180 degree view of the Cove. Whale watch from your Lanai (in season) and a guaranteed swim with the turtles! Always in...
NEW Charming Kapaa Cottage - 1 Block to the Beach!
Welcome to your home away from home in beautiful Kapa'a! This enchanting 2-bedroom cottage offers the perfect blend of Hawaiian charm and modern comfort, nestled in a tranquil garden setting just steps from local attractions. Experience the magic of Kauai from this...
Luxury Poipu Beach House Sleeps 8 with Central AC
This new custom home has 3 large bedrooms & 2.5 baths, perfect for larger parties or families to stay together on their vacation. The house has central AC, high-speed wifi, memory foam beds, and beach chairs and coolers you'll need to enjoy Kauai's beaches. The house is...
Remodeled Top Floor End Unit#49. Perfect location - Sunny & Close to Beach!
Fully updated condo with new open concept kitchen featuring stone counters, kitchen bar, stainless steel appliances, plantation style custom solid wood cabinetry and modern task lighting. Luxurious tiled bathroom also has new plantation cabinets and lighting, tiled...
Maui Resort Rentals: Marriott's Maui Ocean Club Oceanfront Studio Villa
Oceanfront Studio Villa at Marriott’s Maui Ocean Club - New Lahaina or Napili Towers! With its premier location, luxurious accommodations, and sprawling tropical grounds, Marriott's Maui Ocean Club is a perennial Maui favorite, delighting couples and families with...
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
***BEST OCEAN VIEWS IN RESORT*** Top floor, corner unit, with stunning ocean and mountain views, just steps from the beach. Stay cool with brand new central AC. Watch thousands of humpback whales, visible from the lanai. See huge green turtles beached or dip in the...
Hidden Paradise Found with Aloha Spirit and Great Summer Rates! Weekly discount
Cleaner is Covid 19 safety trained. Celebrate the best in indoor/outdoor living in this spacious and well-kept ground floor unit in Keauhou Akahi! Conveniently situated on south Ali’i drive, the condo is 1/3 mile from Keauhou bay and less than one mile from the Keauhou...
*Stroll To The Beach Til Toes In The Sand!*Beautiful Views*Ground Floor*4 Pools*
Wailea Ekahi Village Two bedroom, two-bath, 1505 sq ft. completely remodeled and upgraded, ground floor condo, sleeps six is situated in a low-rise condominium community. The ocean front village is located on Keawakapu Beach in sunny South Maui. The beach has been voted...
Maui Vista Resort. Aloha & Welcome to Maui. Time to kick back and have some fun!
Hello and Welcome to Maui. This is the closest Maui Vista unit to the beach across the street. This non-smoking 1 bedroom, 1 bath Maui Vista unit is located directly across the street from the world famous Charley Young Beach. High Speed Internet for Business. This unit...
Includes Mauna Lani Beach Club Pass. Golf Villa at Mauna Lani D3
This vacation rental is professionally managed by ResorticaHawaiiGolf Villas at Mauna Lani D3. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: Two Twin BedsGuest Bedroom...
Maui Resort Rentals: Honua Kai Konea 212 – 1BR+Den w/ Oversized Balcony & Lush Mountain Views
Konea 212 is a luxurious two bedroom mountain view suite with its defining feature being its incredible oversized lanai offering the perfect vantage point to enjoy breathtaking views of the awe-inspiring West Maui Mountains. This rare two bedroom, one bath suite offers...
Emmalani Hideaway #223
Emmalani Hideaway #223Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in expansive views of the adjacent fairway from this stunning, second-story condo in Princeville. This...
Resort condo with majestic mountain/bay view, lanai, W/D, pools & tennis courts
Hanalei Bay Resort 4205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the Palm Building of Hanalei Bay Resort, this is a condo features truly incredible views of Hanalei...
Oceanfront Waikiki/Ilikai Condo with stunning ocean views and free parking
Oceanfront Ilikai Condo — Free Covered Parking & Incredible Views!Experience one of the best views in Waikiki from this beautiful 15th-floor condo in the iconic Ilikai Hotel & Luxury Suites — with free covered parking (a $50/day value included!).Step onto your private...
Wailea Ekahi Village 15D - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 15D, a stunning one-bedroom, one-bathroom vacation rental nestled in the heart of Wailea. This second floor vacation condo features a covered lanai along the lush greenbelt that terraces between buildings and leads down to the ocean. Partial...
Elegant Oceanfront – Beautiful Remodel - Puamana 254-1.
Puamana 254-1 is a beautifully remodeled oceanfront 3-bedroom, 2.5-bath townhome with an exceptional corner location on the sunny south shore of Puamana that wasn’t harmed by the Lahaina fire. The coconut tree-filled lawn adds to the tropical charm of this magical...
SALE - Closest to the Beach - King Bed - Maui Banyan! -
As Maui residents, my wife and I can truly say there is no better place to live or vacation than Maui Banyan. We bought our condo with a long term goal in mind... retirement later but fun now. We shopped countless others all over Maui until finding the Banyan. Once we...
Oceanfront 1 BR Condo at Kaha Lani KL309
Kaha Lani 309Experience aloha Kauai-style in our fully-furnished, oceanfront condo in dreamy Wailua.Kaha Lani is a direct oceanfront, meticulously maintained property featuring 73 individually-owned condos on the coconut coast. Wake up to an award-winning sunrise...
Wailea Elua 1401 - Beautiful Ground Floor 1BR Oceanfront Unit on Ulua Beach
Welcome to Wailea Elua Village, a premier gated community nestled in the heart of Wailea. Our ground-floor beachfront condominium (#1401) offers the perfect blend of luxury, privacy, and island living—ideal for two (adults only) seeking a serene getaway.Set within 24...
3 Bedroom, 3 Bath Oceanfront Condo With Amazing Views of Molakai and Lanai
3 Bedroom, 3 Bathroom Oceanfront Condominium with Panoramic Views and Sunsets over the Islands of Lanai and Molokai. A hidden gem. Exclusive top floor corner-end Penthouse Suite. Completely private. Beautifully furnished. Split level with vaulted ceilings and...
Ocean View KUL418 - West Maui Beach Front, Fabulous Condo!
** Great 2025 rates Now - Book for future Whale Season November - March!!**This stunning third-floor condo has been tastefully decorated to offer the perfect blend of elegance and comfort. As you step inside, you'll immediately notice the breathtaking view of the west...
Largest ‘One of a Kind’ 2-bd 2-Bth Condo 🏄 New Air Conditioner throughout🌴
Aloha! Welcome to our Paradise Home! Located in building 3 on the 4th floor, away from the noise of So. Kihei Rd.. We hope to make you feel like an invited guest. Wake up to swaying palm trees, birds singing. Make your own coffee and breakfast or walk to a local...
Hanalei Bay Resort 7307+7308: Ocean Views, Pool/Spa, AC
Hanalei Bay Resort is located on the lush, unadulterated north shore of Kaua’i, overlooking the ocean and iconic Hanalei Bay. An ideal home base for couples to explore the garden isle, both units 7307 and 7308 boast one sizable bedroom and one full-size bathroom. With...
Maunaloa 2BR Condo with Ocean Views – Walk to Kepuhi Beach & Pool
Paradise awaits at this beautiful condo in Maunaloa! The 2-bedroom, 2-bathroom vacation rental has everything you need for the perfect Molokai getaway, including a full kitchen with new appliances, in-home laundry, and ocean views. For a relaxing start to the day, enjoy...
Kiahuna Plantation Condo - So Close to the Beach!
Beautiful Kiahuna Plantation is located on world-renown Poipu Beach. Enjoy strolling through 35 acres of tropical paradise with gardens of graceful orchids and unusual cactus. The buildings are plantation style with louver shutters on the windows and ceiling fans...
Spectacular Oceanfront Corner Condo with Expansive Top Floor Views at Wailua Bay View!
Spectacular Oceanfront View Top Floor Corner Condo at Wailua Bay ViewDazzling views of the Wailua Bay from this condo. Your gaze will get lost on the horizon of the Pacific Ocean. Comfy Oceanfront living is yours to enjoy from this top floor condo. The most amazing...
Luxury Oceanside/Beauty, FREE Parking/Wi-Fi, 2/2, AC, W/D, Washlet, Sleeps 6
Ilikai #744 – 1777 Ala Moana Blvd.Enjoy luxurious high-end ocean-view living in this beautiful 2014 remodeled condo at the ILIKAI, the iconic Hawaiian apartment/hotel made famous by the TV show Hawaii Five-O. This 7th floor corner unit boasts magnificent views of the...
Wailea Ekahi Village 17B - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 17B, a one-bedroom residence in beautiful Wailea! This vacation rental offers a spacious and comfortable living space, perfect for couples or small families looking for a relaxing getaway. Step onto the large lanai with spectacular garden views...
Relax in Style! Renovated Hotel Zoned Condo! Your Maui Banyan Getaway!
Experience the Best of Kihei in Our Beautifully Renovated 2BR/2BA Maui Banyan Condo!Welcome to your tropical retreat in sunny Kihei! This stunning fully renovated 2-bedroom, 2-bath condo comfortably accommodates up to 6 guests with a king bed, two full-sized beds, and a...
1 Block to Heart of Hilo: Fully Renovated Home
Family Friendly | At-Home Laundry | 1 Block to Shops, Eateries & OceanWelcome to this 2-bedroom, 1-bath townhome boasting a walkable location near Historic Hilo. The vacation rental is ideal for tourists or business travelers, allowing anyone to easily access popular...
Spacious 2 bedroom, 2 bath, 1 free parking with world famous ocean view!!
Spacious 2 bedroom, 2 bath, 1 FREE parking unit with world famous ocean view!!!Be on vacation every day!! Direct Ocean & Sunset views of Waikiki Beach!!! Swim and Surf directly across the street of just watch the Surfers go by from the lanai! Spacious 2 bedroom, 2 bath...
Best Sugar Beach Maui Direct Oceanfront Modern Luxury Condo #331
Quiet, peaceful getaway with amazing views. Enjoy walking on uncrowded miles of sandy beachfront along a nature preserve, sunbathing, snorkeling, swimming or boogie-boarding on your doorstep. Amazing picture-perfect views of ocean sunrise, sunset and rainbows greet you...
Gorgeous 2 bedroom with loft villa with Private Beach Access
The Big Island offers breathtaking views and lasting memories. Now would be a great time to consider E-22 at the Golf Villas for your upcoming Hawaiian vacation. Up one flight of stairs (16 steps), you will enter a beautiful open concept living space. The living area...
Kamaole One Heaven in Kihei - Unit #11
Our spacious, ocean front Kihei condo rentals, offer year round fun for you and your family. Whether it is a romantic stroll on one of the longest beach walks on Maui, or watching the winter antics of the humpback whales, there is nowhere like Kamaole One for a vacation...