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.
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...
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
Location: Beachfront, situated between two beautiful beaches with a protected beach directly in front, offering miles of warm, calm, shallow ocean suitable for all swimming levels, snorkeling, paddle boarding, and kayaking.Views & Outdoor Space: Amazing 180-degree ocean...
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...
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...
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 now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6...
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...
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,...
Waikiki Sunset Mountain View 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...
Westside Magic Garden 3bed 2 bath house
Welcome to our charming vacation house located on the beautiful west side of Oahu, Hawaii! Our cozy rental is the perfect spot for travelers seeking a mix of adventure and relaxation, as we are conveniently located near some of the island's most stunning beaches, hiking...
Sept.-Nov. Special $350 nt! BEAUTIFUL NEWLY RENOVATED OCEANFRONT
CONDO had A FULL RENOVATION,WITH BEAUTIFUL UPGRADES AND ALL NEW FURNISHINGS. The condo is a 1700 sq ft. ocean front, fifth floor, two bedroom, two bathroom condominium with AC that offers stunning views of Hawaiian sunsets, whales, sea turtles, and the islands of...
1 Bedroom Corner Oceanfront #701
Our One Bedroom Corner 701 unit is spacious and well-appointed with a King Bed in the bedroom and a Queen sofa bed in the living room. There is seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The...
Hale `Ohana ~ Family Home - Kuilima Estates East
Welcome to Hale 'Ohana ~ The Family Home, your idyllic retreat nestled in the heart of Kahuku on Oahu's East Side. This cozy, thoughtfully designed 1-bedroom, 1-bathroom vacation rental offers a perfect blend of comfort and convenience, ideal for families or small...
Serene 5-acre tropical hideaway with lanai and circular wood-burning fireplace
Hale Hapu'uOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Nestled on five acres of rainforest, Hale Hapu'u is a serene two-bedroom, three-bath hideaway home in Volcano Village. This...
Charming 1br Top Floor Condo in Poipu, AC, Athletic Club, Beach Access
Welcome to Sunny Poipu Beach! This charming top floor Kiahuna Plantation condo was freshly remodeled with you in mind! Relax on your private lanai overlooking the garden while being steps to the sand. Surf spots, long walks and lifeguarded beach are at your fingertips....
Akahai at Poipu Beach By Parrish Kauai - elite home private pool & central AC!
Tucked back in one of Poipu Beach’s newest vacation rental neighborhoods, Akahai offers an exquisite and distinguished private luxury Kauai vacation rental unmatched by many. This exquisite three bedroom home offers a modern and open floorplan with designer touches,...
Ocean Front Pool, Private and Newly Renovated Top Corner Unit
Welcome to our condo in Hawaii, we like to give everyone a well deserved and affordable vacation. This is a very private and newly renovated, top floor corner unit centrally located in Kailua-Kona, Big Island Hawaii. 350 days of sunny weather in a year with some of the...
KBVC3 · Tropical 1 Bedroom with 2 Full Bath at Resort
Welcome to `Wahi Maluhia`! Peace to replenish your soul at this beautiful, simple Tropical Condo. Walk to the beach, enjoy the pools and spas, play some tennis and take advantage of grounds of adjacent Resort and picturesque oceanfront setting. Free parking affords you...
New! Lae Nani 536, Oceanfront, Tropical Oasis, Steps to Beach and Town
Lae Nani Resort Kauai #536, Beautiful Oceanfront Unit on a Tropical Beachfront Oasis. This Kauai Vacation Rental is conveniently located in Kapaa Town within walking distance to shops, restaurants, and just steps to beautiful white sandy beaches. Accommodates up to 4...