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.
KKSR#3203 DIRECT OCEANFRONT, 2ND FLOOR, REMODELED, SPECTACULAR VIEWS!
Keauhou Kona Surf & Racquet Club#3-203 DIRECT OCEANFRONT, 2ND FLOOR OF BUILDING#3 in complex! #3-203 is extensively upgraded & remodeled.A truly beautiful oceanfront condo in a gated complex with unobstructed ocean and Kailua town views. Elegant furnishings in this...
Two-story, oceanfront condo with pool, water Views, & balcony
Mahina Surf 214Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Slip into Hawaiian time at this gorgeous, two-story, family-friendly condo. Brew up your Kona coffee and prepare all...
BACK IN THE RENTAL PROGRAM JUST IN TIME FOR WINTER, AMAZING OCEANFRONT VIEWS!
ABOUT THE CONDO...This beautifully decorated one bedroom direct oceanfront condo provides GREAT views of the pacific blue and is centrally located on the West side of Maui. From the Paki Maui Resort you are within walking distance of a grocery store, Farmer's Market,...
Keauhou Punahele Golf Course and Ocean View
Hawaii, Big Island, Kona, Keauhou Punahele, golf course with the ocean in the background. The condo is located close to Keauhou Bay, Keauhou shopping center (with cinema) and snorkel/surfing beaches.We have owned this top floor 3 bedroom/3 bath room unit overlooking the...
Oceanfront Oasis with Stunning Views 2BR 2 BR
Take advantage of this newly listed direct Oceanfront Condo with stunning views. My updated condo features unobstructed views of Maui's beautiful turquoise waters with Molokai and Lanai in the background. The striking panoramic views will immediately put you in your own...
Island getaway with heated pool - walk to dining
Alii Villas 201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Boasting a pool and an oceanfront location at the Alii Villas, a choice island getaway awaits at this updated condo....
Enjoy Beachside Living! Relax at the Popular Colony Surf #307
*Check-in Assistance Fee for Colony SurfFor check-in assistance outside of Aska Gateway's operating hours (9 am - 5 pm HST Monday through Friday) and on federal and state holidays, the check-in assistance fee is $200 (plus tax).**There is a water shut-off scheduled in...
Dlx Beachfront Maui 2-Bedroom Condo...Steps to the Sand!nWest Maui/Ocean Views!
Welcome to your own 2-Br Beachfront Maui Condo...Ideally located just 5 min north of Kaanapali, in beautiful West Maui. You'll love the Oceanfront Views...framed by the outer islands of Molokai & lanai, as you listen to the sound of the surf from the Spacious Lanai!...
Lava Lounge-Pool view/walkout access, 2 Queen Beds
Fully remodeled ground floor unit with direct pool access and waterfall views at the private beachfront resort, Outrigger Kauai Beach Resort & Spa.Ideally located between the North and South side of Kauai. Less than three miles from the airport and a short drive from...
Spectacular two-story ocean-view home on two acres with covered lanai
Big Island Getaway, Ocean View ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Offering breathtaking ocean views and a prime location in the Hamakua Heritage Corridor,...
Experience Maui Sunset A504: ocean views, spacious living, and resort amenities!
Maui Sunset A504, great location with peaks of the ocean! This 1bedroom/2bath condo offers the perfect getaway. Plenty of room for a small family or couples traveling together.Enjoy indoor/outdoor living with private lanai. Take in a peaceful Maui morning while sipping...
Beautiful Oceanfront! Huge Lanai! Summer Specials!
Hale Ono Loa #311Flat screen TV, Cal King bed, HUGE lanai, onsite laundry facilities. All tile flooring! Tastefully remodeled! Swim in the large in ground pool and snorkel with turtles right in front of property! Fully equipped condo is supplied with all basic amenities...
NEW | Brand NEW AC | Steps to Beach on Kiahuna Plantation
Come and relax at this 1-bedroom condo with lanai, located at the tranquil & lush Kiahuna Resort.The condo is centrally located in Poipu and is within a 5 min walk of the beautiful Poipu Beach and includes complimentary access to the Poipu Beach Athletic Club, includes...
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 & partial ocean views, gourmet kitchen, and access to pools, hot tubs, fitness center, & 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...
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...
@ Marbella Lane - Sunshine Seascape | Ocean View
Summary:Embark on a retreat to our contemporary haven boasting tranquil ocean views. This getaway offers all the essentials for a perfect stay. Marvel at the view through ample windows, unwind on the expansive terrace enveloped by lush foliage, and relish moments of...
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...
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...
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
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 Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
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...
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
FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W3)*One...
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...
KBV 36G5 Luxurious 1BD Condo w Unobstructed Ocean Views
FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W3)*One...
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...
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...