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.
Family Vacation Home w/Ocean View at Makaha Valley in Secure Gated Community
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.May 2025 the Community Pool, Jacuzzi, and Gym are now OPEN!!This locally owned, green, garden home with breathtaking Ocean and ; Mountain...
Fairway Villas Waikoloa F6 - Large Luxury Corner Villa with Golf Fairway View
Waikoloa Fairway Villa F6 is the ultimate getaway with merged indoor/outdoor living spaces and our 3 bedroom, and 3 bath townhome is perfect for up to six guests. Our well-maintained end unit has lots of light and breezes. We have high-end furniture, amazing gallery...
KBM Resorts | FREE CAR | Honua Kai Konea | 1-Bedroom Beautiful Ocean & Mountain views! HKK-922
9th-floor villa in Konea Tower with Maui Mountain and partial ocean views, gourmet kitchen, and access to pools, hot tubs, fitness center, and beach. A perfect island escape!** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date...
Kahana Sunset A8 - Direct Oceanfront - Two Lanais - Free Fun
Treat yourself to this direct oceanfront tropical getaway at Kahana Sunset Resort. When you enter this beautifully remodeled 2 bedroom/2.5 bath condominium, you will be immediately captivated by the breathtaking views of the Pacific ocean. With two oceanfront lanais, it...
Upscale 2BR/2BA Ocean View in Waikiki + 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...
Best Maui Location * REMODELED Condo*BRAND NEW AC!!
*As of December 2024 the owner has upgraded the property and now there are split AC's throughout the property to ensure all guests are comfortable and cool at any time of the day* You will wake up each morning surrounded by freshwater ponds and the sounds of waterfalls...
Quaint 1bd garden view in great location
Paki Maui 120 is a 1-bedroom, 1-bathroom condo located on the first floor with wonderful garden views from your lanai and floor-to-ceiling sliding glass doors, bringing natural light into the condo. The condo does not have air conditioning. Enjoy preparing meals at home...
Malia Makai - D - Dolphin - Air Conditioning, Special Remodel
MALIA MAKAI D AT KOLOA KAI VACATION RENTALSDOLPHINYour Tropical Getaway in the Heart of PoipuWelcome to Malia Makai D – Dolphin, a charming 2-bedroom, 1-bathroom cottage in the heart of Poipu. This stylishly updated rental combines modern comforts with the beauty of...
Gorgeous Lagoon View At The Ilikai Hotel! Firework view on Fridays!
Beautiful Lagoon View on the 16th Floor!Looking for a place with breathtaking views, this condo is for you! Step out to relax on the your lanai & enjoy the views of the Duke Kahanamoku Lagoon & Pacific Ocean. End your week with the Friday night fireworks, off the...
DIRECT SANDY BEACHFRONT just steps away fr the patio.Ground Fl.condo 1bed2ba2pkg
Situated in the destination spot on the north shore of Oahu in Haleiwa Town. As soon as you step into the condo, the beautiful blue ocean view takes your breath away. Listen to the ocean waves while relaxing on the patio or step onto the sandy beach perfect for...
Kaha Lani Resort #326, Oceanfront, Steps to Beach, Free WiFi & Parking
Kaha Lani Unit #326 - Oceanfront Kauai Vacation RentalWelcome to Kaha Lani Unit #326, your perfect oceanfront retreat in Wailua, Kauai. Nestled on the top (3rd) floor, this charming 739 square ft. 1-bedroom, 1.5-bath condo offers breathtaking views and direct access to...
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom (corner unit)
“Kama” – Unit 107 – is a 1-bedroom, partial ocean view condo located in Hana Kai’s Mauka (upper) building. This is a ground floor, corner unit with a King-size bed in the bedroom and a full size futon couch in the living room. There is a pass-thru window from...
Hunter Hales KALA cottage is the Perfect Getaway!
Hunter Hales “KALA” is one of two identical 810 sqft cottages on one half acre lot privately located just behind the Haiku Town center. This listing is for “KALA”cottage. Conveniently located at the start of the Road to Hana. Enjoy the quiet laid back life style...
Reduced May 2025 Rates. Remodeled unit with Air Conditioning and Stunning Views
This ground floor, tropical oasis is only steps from the ocean and lies between two beautiful beaches with another protected beach in front. The sunsets and 180 degree ocean views from your lanai are amazing!. We just completely remodeled our kitchen, painted...
Aloha Awesome Views! Oceanfront Condominium, Maui Sunset A219
BREATH TAKING VIEWS!! Our beautiful 1200sq ft, 2 bedroom, 2bath condo, has ocean and mountain views from the Lanai and Haleakala Mountain views from the bedrooms. Master has a King-size bed with private bath, second bedroom two twin beds with bath. The condo has a...
Aston Maui Kaanapali Villas C259: Studio garden view condo on Kaanapali Beach
Maui Ka’anapali Villas #C259: Studio garden view condo at Beach Front Resort on N. Kaanapali Beach*There is currently NO Air Conditioning. The Air conditioning system is undergoing emergency maintenance through June 2024. Experience the verdant garden views at this...
Cozy Ground Floor Condo at Kihei Akahi C-108
My condo at Kihei Akahi C-108 is not just a vacation rental, it is my second home. I personally visit several times a year to make sure it is properly prepared for your enjoyment. Tropical style louvered windows let in 100% of the breeze from the Trade winds and offer a...
Best Studio Ocean Views at Honua Kai - Soak In Maui Sunsets on This Expansive Lanai -Hokulani 719
Experience the Best Studio Ocean Views at Honua Kai - Soak In Maui Sunsets on This Expansive Lanai -Hokulani 719E komo mai (welcome) to Kai Maluhia (“The Calm Ocean”), your new Maui retreat where the serene beauty of Kaanapali Beach meets the luxurious comforts of...
Great Ocean View, One Bedroom at the Ilikai Hotel
1 Bedroom Deluxe Lagoon View on the 13th Floor!Look no further, you've found PARADISE! This 1-bedroom is over 500 sq ft of space, making is spacious for a single traveler, family, or friends traveling together. Situated in the 40 stack of the Ilikai Hotel, this location...
Walkable condo with two pools, hot tub, tennis, grill & beach access
Maui Kamaole D105Our 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...
Breathtaking Sunsets World-Class Snorkeling & Surf | Relax in A/C Comfort KVR
Welcome to Hale Makolea 23 – Your Ideal Kona Coast RetreatDiscover the charm of island living at Hale Makolea 23, a serene and inviting two-bedroom, two-bath condo nestled within the tranquil Makolea complex. Surrounded by lush tropical landscaping, this thoughtfully...
PERFECT FOR A COUPLE GETAWAY! OCEANVIEW, CLOSE TO BEACHES, SHOPS & RESTAURANTS!
WELCOME TO VALLEY ISLE, LOCATED IN THE HEART OF KAHANA!Valley Isle Resort is a low density oceanfront property located on Kahana Bay in West Maui. Your within walking distance to restaurants and stores. Centrally located between Kaanapali and Kapalua and just a short...
KA 401 Spacious Studio w Mountain Views Pool AC
Kaleialoha 401 Gorgeous Mountain View Studio - In Oceanfront Resort FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple...
Puumoi ocean view hideaway
Puumoi ocean view hideaway is a colorful and comfy one bedroom accommodation that boasts some of the best sunrise views on the Hamakua coast.The property is on a 20 acre horse ranch with a sprawling grass lawn right outside the door. In the valley below the barn is a...
Kolea 14F | Heated Pool, Gym & More!
Summary:This vacation home has 2 bedrooms and 2 bathrooms spacious enough to house up to 5 guests. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Kolea 14F is nestled along tranquil blue waters and soft sand beaches of Anaeho'omalu Bay...
Kapaa Shore Resort B118, Ocean View, Walk to Town, Bike Path, Comp Wifi & Pkg
Kapaa Shore Resort B118, Ocean-View, Ground Floor, End Unit. Kauai Vacation Rental on the Coconut Coast. Accommodates up to 4 guests, including children and infants.Ground floor, One bedroom, One bathroom, ocean-view unit with heated pool, hot tub, and BBQ grills.612...
Amazing 2 Bdrm Penthouse with Sea, Diamond Head and Ala Wai Views with Parking.
This magnificent 2 bedroom penthouse apartment has sweeping ocean and Diamond Head views that will enchant you. From the garden feature at the apartment entrance to the granite bench tops, top quality kitchen appliances, leather lounge suite and stone work in the...
Oceanfront 3BR/3BA at Kona Reef: Spectacular Views, Ideal Location!
Relax on the Kona Coast in scenic Kailua-Kona, this vacation home features oceanfront views and is perfect for a family or group of friends. Kona Reef is next to Honles Beach and is blissfully tranquil. Enjoy being close to the iconic Alii Drive and downtown Kailua...
Hale Kamaole 220 Second floor condo, easy access to best beach on Maui!
This one bedroom condo has a Ocean & Garden View. Artistically decorated with beautiful tiles used in kitchen and bathroom, walk-in tile shower. Updated completely in Hawaiian style. King bed in bedroom with queen hide-a-bed in living room. Cabinetry in kitchen area...
Hilton Waikoloa Pool Pass thru June 2025. Golf Discounts. Kolea 16B
This vacation rental is professionally managed by ResorticaHawaiiKolea 16BPlease scroll down for detailed informationHilton Pool Pass: Valid for stays through December 31, 2025. Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6 person...
Aston Maui Kaanapali Villas E295 Oceanfront 1 Br on N. Kaanapali Beach
Maui Ka’anapali Villas #E295: One bedroom oceanfront on N. Kaanapali Beach with Pool and Beach AccessThe glorious Pacific awaits, feast your eyes on the unfiltered splendor that is oceanfront in the highly coveted Emerald building at the Maui Ka’anapali Villas. This...
KBV 23B1 Kapalua Bay Upgraded OceanFront Villa
Kapalua Bay Villas 23B1 Sensational OceanFront 1Bedroom Kapalua Bay Villas with Designer Upgrades, Ocean Views, Central AC, Pools, Tennis Courts, and Close to Famous Golf Courses FREE daily activities included with your stay value up to $1035! Complimentary admission,...
Maui Dream - Remodeled Ocean View Penthouse, Steps to World Class Beach
Come stay at our remodeled Maui dream home!Amazing location right across from Charley Young Beach (next to Kama'ole 1), wonderful Maui swimming and snorkeling beach. The condo has an ocean view from lanai. Charley Young Beach is directly across the street.Our condo is...
MAUI is PARADISE at Kihei Alii Kai C307 - Quiet side of complex.
Welcome to Maui and our beautifully tropical décor 1 bedroom, 3rd floor condo – C307 in Kihei Alii Kai. We are in the upper building on the "quiet side of the complex", close to the parking lot and elevator access. The grounds are beautiful tropical fauna.We boast a...
Outstanding Oceanfront 🌅 Deluxe Condo! ✨ Kona Reef D-14
Just one of the wonderful experiences you came to Hawaii for.... an outstanding oceanfront condo to make your stay complete.Our fresh one bedroom unit is on the second floor of the D building of the wonderful Kona Reef Resort, really only six steps up! (Unit D14), From...
Maui Banyan Q-109 Unit B | Steps to the Pool!
Perfect for kids and grandparents! Most convenient unit in Maui Banyan!We are so happy to be offering Maui Banyan Q109B. This unit is our home away from home in Maui. We chose this condo specifically because it is exactly what our family wants. It is on the ground floor...
White Sands Village #227
This lovely and quiet 2 bedroom, 2 bath condo is located on the second floor, there is an elevator to assist as well as open stairs. There is 2 queen sized beds with a large open kitchen, living room area that leads to the spacious lanai that has an ocean view and...
Amazing Beachfront Townhouse - Hale Mahina #B405 - Unforgettable Views!
Welcome to Hale Mahina #B-405, a stunning oceanfront condo located in the highly sought-after Hale Mahina Beach Resort on West Maui. This top-floor unit offers breathtaking views of the Pailolo Channel and the neighboring islands, perfect for whale watching from the...
Luxurious 2bd penthouse with Sunset Views
Kahana Manor 701 is a luxurious 2-bedroom, 2-bathroom penthouse that can accommodate up to 4 guests and features central air conditioning. Please note that while this complex does include elevator access, you must climb one flight of stairs to access this penthouse...
Hilo Home w/ Private Deck + Stunning Ocean Views!
Get the most out of your next trip to the Big Island with this stunning Hilo vacation rental! With 2 private decks overlooking the water and picture windows throughout, this cliffside, 2-bedroom, 2-bath home ensures plenty of breathtaking views for the entirety of your...
Hale Kauwela | Ko Olina | Resort Villa w/ Views
Summary:Welcome to Hale Kauwela in Ko Olina. Kick your feet up at this gorgeous villa perfect for your paradise vacation. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Professionally and locally designed, this condo captivates...
Unobstructed View of the Big Blue Pacific and A /C Throughout
Enjoy awesome ocean views from almost every room in this ocean front, three bedroom, 1126 square feet, fabulous unit! Living room, dining room, kitchen, Master bedroom and second Master offer 'front row' spectacular views of the Blue Pacific, West Maui mountains,...
Aloha Vibes w/ Ocean Views, Near Beach + 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 Kamaole Kihei Resort I Beaches, Pools, Tennis
Prime South Kihei location across the road from Kamaole Beach lll and a 15 minute walk or 5 minute drive to Keawakapu Beach. Set on a 23 acres, Maui Kamaole is a lush, tropical resort with two swimming pools + spas, and two tennis courts.J201 is a large, upgraded condo...
Ma'alaea Surf Unit E5-2BD Beachfront Condo, AC, Wifi, Pool, TV, Kitchen
Ma'alaea Surf, Unit E5, the most glorious and romantic sunset views at is why the architect who designed Ma'alaea Surf chose this unit for his home. Steps away from the wonderful walking beach and pool. This fully equipped unit features flat screen tv, cable, Wi-Fi,...
Oceanfront Resort steps to pool/beach via your lanai, 4 Beautiful Pools
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful first floor unit with excellent views of the resort and pools. Comfortable king bed with chaise lounge. Walk right out your lanai and you will be at the pools and...
Gorgeous Diamond Head Penthouse Studio Stunning views, Private Balcony.
Legally permitted vacation rental - 2947 Kalakaua Ave, Penthouse 5Stunning style with incredible Ocean & Diamond Head views.The care and attention to detail our owners put in, bringing their pride and joy on Hawaii's Gold Coast to fruition shows in every corner of this...
Tropical-view escape with pools, hot tub, tennis, AC, W/D - beaches await
Maui Kamaole D209Our 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...
Beachfront/View MAK-B1 -Quality Remodeled Condo in Ma’alaea Great Value
Are you looking for a luxurious and comfortable vacation rental that feels like home? Look no further than Makani A Kai # B-1, a deluxe condo located in a beachfront resort. With a minimum stay requirement of just five nights, this unit is perfect for a short or long...
Maui Banyan #Q-104: 2 Br in S Kihei, Walk to Beach, Shops and Dining
Located in building Q at the Maui Banyan, this two-bedroom condo has many upgrades and remodels. The Master bedroom has a queen bed and a full bathroom ensuite. The second bedroom has two full beds. There is a full bathroom just outside the second bedroom. The living...