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.
TRUE Oceanfront Renovated Kamaole #206
Beach beach beach front!! Access to both Kamaole 1 and 2 beaches!Fully equipped kitchen, master bedroom with king bed, 1 double bed and twin bed in second room, brand new furniture and appliances through out condo. Washer & Dryer, flat screen cable T.V's. wall safe &...
Kona Cliff House at Pebble Beach - a romantic getaway!
Kona Cliff House at Pebble Beach is a romantic getaway & perfect for all things ocean! Spectacular coastal views from every room in this fully remodeled penthouse. All full custom gourmet kitchen stocked with your chef needs. Location absolutely does make a difference!...
May 25- Jun 14 $140 KKN-Get Spoiled in DLX unit/Low total price/Best S. location
Our unit listing is in the Kihei Kai Nani Resort and is "Resort - Hotel" designated property and not apartment zoned. We have enjoyed hosting guests since 2011 in short term rental stays and are able to continue as is everyone in the Kihei Kai Nani Resort.Hawaii tax ID#...
Hale Nalani, Private Luxury with a Pool and A/C
Hale Nalani, Princeville Hale Nalani, “House of the Heavens,” can be found in the resort community of Princeville. A walled courtyard provides privacy to this single-level, 3-bedroom, 2.5 bath home, which also features a 40-foot (12 m) lap pool.Tropical hardwood...
Beautiful & Spacious - J202
The Maui Kamaole is a luxurious low-rise, townhouse-style complex on 23 tropical acres set on a hill overlooking the ocean. The property has two beautiful swimming pools. The pool closest to our unit is set in a tropical garden with a waterfall and has an adjacent sand...
Beautiful, Updated & Lush Settings 🐠 House with Privacy, Pool & Nearby beaches🐢 Kololia Living
Kololia Living is a beautiful and private 3 bedroom, 2 bath home set on 1/3 of an acre. It's neighborhood setting places it close to Kona's beaches, and a nearby walking trail. The grounds are studded with beautiful, lush plants, including many different fruit trees!...
Ocean & Ocean View-Fully Equipped Condo at the Fabulous Ilikai Aug/Sep Special
Aug 20 to end of Sep Special! we always have a one month minimum, at a great price. Just type in your dates and you will receive our special rate. The world famous Ilikai Hotel is a resort type property with hotel rooms and condos, 2 pools, shops and restaurants. Condos...
Awesome Ocean View Condo w/ FREE Wi-Fi and Parking!
Waikiki Banyan #3601-T1 – 201 Ohua Ave.It hardly gets better than the vantage point from this 36th floor end unit! Your panoramic view includes the Pacific Ocean views, Waikiki, Diamond Head, and Kahala to Koko Head! This modern air-conditioned contemporary has...
Puu Poa 308: 2 BR, 2 BA Condominium in Princeville, Sleeps 4
Step into paradise at your own Princeville oasis. This oceanfront two- bedroom, two-bathroom condo is in the coveted Pu'u Poa development. The thoughtful design and luxurious finishes truly rival the panoramic ocean views. From the custom craftsmanship, curated...
BEST Ocean View in the Resort...Stunning & Panoramic! Completely Renovated 2BR
There are ocean views ... then there are "OCEAN VIEWS"! This gorgeous condo is unit # 218 at the Kaha Lani Resort, which is located on Kauai 's beautiful east shore, the famous 'Royal Coconut Coast'. This building is the closest to the ocean, and this unit truly has the...
White Sands Village | Oceanfront
Summary:Say aloha to your home away from home on the Big Island! Maximum occupancy strictly enforced in accordance with local ordinances.The Space:White Sands Village is an oceanfront condo complex in the gorgeous town of Kailua-Kona. Guests will find themselves in the...
Top-floor getaway with lagoon pool, hot tub, tennis & beach access
Maui Kamaole D205Our 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...
Steps to the Beach, Beautiful, Clean 1 Bedroom Condo
Mary and I found we really enjoy Maui, and decided to purchase this condo in Kihei in March of 2017. Our condo was recently remodeled - new floors, cabinets and granite countertops. The bathroom was done as well, with a nice walk-in shower. Kihei Bay Vista is a...
Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves
This beautiful ground floor unit was completely remodeled in 2015 and every surface is brand new. If you prefer one of the shortest and most level walks to the beach in Ekahi Village, then condo 21-C is for you! (The complex is situated on a hillside.) Enjoy relaxing...
Modern & Private Condo in a PRIME Location!
Resort style living in a beautifully maintained property with a lush tropical setting. It's an 8 minute walk to dining, shopping and limitless activities in Kona town.Located across from Royal Kona Resorts and world famous Don The Beachcomber bar which is famous for...
Maui Resort Rentals: Honua Kai Konea 249, Spacious Interior Courtyard 3BR w/ Partial Ocean Views
This exquisite three-bedroom suite offers an incredible location, the first unit back from the very front of the building. You will be perfectly situated to enjoy partial views of the Pacific Ocean while soaking up the morning sun with your breakfast and listening to...
*** Beautiful Oceanfront Maui Condo Right on Sugar Beach ***
🌴☀️🌴 TOURISM WELCOME! We are a fully legal Short Term Rental (STR) condo and have been hosting for10+ years (Premier Hosts). While Lahaina town is closed, the rest of the island (including areas of West Maui) is open, and visitors are welcome. Respectful...
Villas By The Cove, Villa 2 · 1 Bedroom Beach Villa Steps to the Sand
Villa 2 at Villas By The Cove is a spacious garden view 1 bedroom Villa Suite located just steps from two of South Maui's most popular white sand beaches. Newly remodeled and conveniently located, this 600 sq. ft. single story 1 bedroom villa offers ocean views, privacy...
Adorable 1930's Gingerbread House....Permitted!
This renovated and adorable "Gingerbread House" is a studio cottage nestled amongst beautiful trees and tropical flowers and an organic farm growing Turmeric, Ginger, Papaya, Tangerines, Avocado, Oranges, Lemons, Grapefruit, Macadamia Nuts, Lychee, coffee and tropical...
Kahakai Estates Hale: Posh Gold Coast Home w/ Pool, Spa, AC & Sunset Views
Kahakai Estates Hale by Gather – Newly Renovated Luxury Vacation Rental in Kailua-Kona, Big IslandLocation: Kahakai Estates, Kailua-Kona | Sleeps: 6 | Bedrooms: 3 | Bathrooms: 2.5 | Central A/C | Private Pool & Hot TubEscape to paradise in this fully remodeled,...
Location, Location, Parking, Kitchen, Remodeled
W Hotel inspired design in this newly remodeled and fully upgraded designer condo at a value price. Everything is new. Traverine floors throughout. The kitchen includes granite counter tops Italian glass tile back splash, and dishwasher. The bath includes a vessel sink...
Experience Bliss: Beachfront Panoramic Ocean Views at Sugar Beach Resort PH27!
Sugar Beach Resort #PH27 – Penthouse Oceanfront EscapeWelcome to Sugar Beach Resort #PH27, a fully renovated one-bedroom, one-bathroom penthouse condo with panoramic oceanfront views. Located in North Kihei, this oceanfront retreat places you directly on Maui’s...
Haena Beach House – Luxury Oceanfront Kauai Retreat
TVNC 1258Haena Beach House offers a once-in-a-lifetime vacation experience, providing contemporary luxury in a private beachfront setting. Ideal for large groups, the home showcases breathtaking panoramic views of the Pacific from its living spaces and each of its...
The Dream View Vacation - OCEAN FRONT -
This is the Paradise you have Dreamed of.... Where the Tropical Bluff Ends and the Spectacular ~ Panoramic ~ White Water Ocean View Begins. You just discovered a NEWLY RENOVATED ~ Top Floor ~ End Unit ~ Private Penthouse Location. Perched atop the Ocean Bluff you will...
Luxurious villa with high-end finishes, AC, and a large private lanai.
Some of the features include: Travertine Tile, Granite, Marble, Top of the line Stainless Steel Appliances, Mahogany Cabinets, Luxury, Quality Furniture, Plush Carpeting, Air Conditioners in all rooms, and Mirrors throughout. This is truly a perfect getaway!This...
Aloha Condos, Keauhou Kona Surf and Racquet Club, Condo 2-302, Oceanfront, AC
Oceanfront Top Floor with sunsets over the clear blue Pacific waters every evening: Loft and Vaulted CeilingsDirect, Unobstructed Ocean ViewOceanfront Master Bedroom • Great Oceanfront Location• Pool, Cabana & BBQs• 3 Lighted Tennis Courts• Tropical Gardens &...
Ocean Front - Air conditioned Condo - Minutes From Downtown Kona, STVR-19-376325
Spectacular Ocean front condo in highly desirable location. This condo was completely remodeled in 2023. "100% teardown to studs". Cool Air Conditioning, noise dampening windows and walls. Top end features throughout, no expense was spared. Waterfall countertops, Bosch...
Luxurious remodeled townhouse with gorgeous ocean, island, golf course AND coastal views! 60% off Hotel Prices!
Property Highlights • Five minute walk to three world-class beaches, including Kapalua® Bay, rated the "Best Beach in the World" by Dr. Beach, and “Best Beach in the US,” by Conde Nast • Gorgeous remodeled townhouse with stunning ocean, island, coastal AND...
Spacious, mountain view home, across from beach path! Ka Wai Aloha TVNC-5137
Bright, fun and steps to the beach, this home is great for family gatherings and retreats. Ka Wai Aloha is located in Haena two blocks away from the pristine, aqua waters of Naue Bay and a 20 minute beach walk to Kauai's famous, Tunnels Beach. Haena has one main road...
2BR 2BA end unit Ke Nani Kai Molokai, HI Unit 151 - Ocean View, Remodeled
Beautifully renovated ground level 2 BR/2Bath end unit on Island of Molokai, HI with partial ocean views and wrap around Lanai. Unit 151. Tucked away in the back corner of the complex provides more privacy than most other units at KNK.Wi-Fi &cable TV, new flat screen...
R413-Pool-Spa-Beach-Turtles-Ocean Access-w/d-A/C, Spectacular Garden Oasis w/ W/D and AC, Pool
Escape to Pool-Spa-Beach-W/D in picturesque Poipu for an unforgettable retreat. This inviting home features 2 bedrooms, 2 baths, and modern amenities like a washing machine, Wi-Fi, and a fully equipped kitchen. Just steps from stunning beaches, it's the perfect spot for...
OCEANFRONT PROPERTY - MARCH OPENINGS! WHALES! Kihei Sands Beachfront Condo-A7
ALOHA! Are you ready to spend some time barefoot at the beach? Let us welcome you to Condo A7! All you'll need is a carry-on full of swimsuits & the slippahs on your feet when you arrive at Kihei Sands Beachfront Condos in sunny South Maui. See what it's like to have...
Casa Makara: Stunning Golf Course, Mountain & Waterfall Views w/ Central AC
Welcome to Casa Makara, a serene retreat nestled within the peaceful resort community of Princeville on Kaua‘i’s North Shore. Overlooking the lush fairways and tropical landscape, this 1,800-square-foot home blends island comfort with modern design—an ideal...
Big Island Vacation Rental (on The Island of Hawaii) at Punaluu Beach
This is a true one-bedroom unit, not a small studio unit that is (often) described as a one-bedroom unit.This unit at Colony One, Sea Mountain, is a full one bedroom unit with a king-size bed in the bedroom on the lower level, and the living room, dining and kitchen on...
Spacious ocean view condo, closest to sandy beach
Maui Kamaole G208 has central A/C, is a two story, 2-bedroom, 2-bath spacious condo situated on the 2nd floor, and can accommodate up to 6 guests. Please note that this low-rise complex does not have elevators. Please note that there is a flight of stairs to get up to...
Ocean & golf views , watch amazing sunsets over Lana'i- J301 2/2 Sleep up to 7
Aloha! Our condo complex was not damaged by the Lahaina fire. All the beach and golf services are open. Ka'anapali Whalers Village restaurants and stores are open. Areas north such as Kahana, Napili and Kapalua are also open for dining and golf and were not impacted....
Kihei Akahi C-411 - Modern Top to Bottom Remodel, Split-AC, across from Kam II
Enjoy the clean and open style of Kihei Akahi C-411, a meticulously renovated contemporary condo in South Kihei. This fully remodeled unit boasts a seamless blend of style and comfort, featuring brand-new flooring, paint, fixtures, and furnishings sourced from Maui's...
Ground-Floor Pili Mai Condo With Central AC, Shared Pool & Hot Tub, Golf Course
Pili Mai 7HOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience a new Hawaii? Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in...
$50 off Spring/Summer for Waikoloa Beach Villas, 2 Story End Unit!
Come share the enjoyment of our home away from home in Hawaii!Enjoy your stay at this Hawaiian plantation style villa adjacent to the King's Shops and a short walk to the scenic Anaeho'omalu Bay. The villa is located on the 3rd green of the world class Beach Course in...
Haleakala Shores A-301 - Golden Sand Beaches, Ocean Views, Sleeps 6, Split AC!
You cannot get closer to the beach in South Kihei for this rate. This corner, front row unit features expansive ocean views from the living room and lanai, and just across the street awaits one of the most beautiful beaches in all of the islands -- Kamaole III....
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.
Aloha & Welcome to Maui’s Oceanfront Family Vacation Dream Home, Puamana 31-1. This spectacular front-line four-bedroom + den, four-full-bath, two-story townhome is just 25 feet from the water’s edge. The spacious open floor plan offers a picture-perfect ocean...
Serene and Peaceful with Heated Pool
Enjoy your very own tropical paradise in one of West Maui’s newest, legally permitted rental properties. You’ll appreciate the magnificent ocean view along with a private, heated swimming pool at Aloha Spirt Maui.This luxury Balinese 2-bedroom, 2-bath house is...
Waikiki Banyan 1BR w/ Great Ocean Views, Steps to 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...
Ocean View Studio - Polu Hale - 2 min Walk from Beach
Enjoy your vacation in Hawaii in this beautiful and spacious studio with gorgeous turquoise ocean view. Indulge in luxurious amenities like a romantic king size canopy bed, a huge 47' LCD TV, a well equipped kitchenette with granite counter tops, a rock vessel sink in...
Breathtaking Newly Remodeled Oceanfront Condo 2BD/2BA - Remarkable Molokai Views
Mahina Surf is west Maui at its finest. Once you stay with us in #223, you won’t ever want to leave this breathtaking slice of paradise. Mahina Surf #223 is a luxury 2 bedroom/2 bath oceanfront condominium with spectacular ocean views, including a tremendous view of...
New Listing Perfect Ocean Front Location 2BR Kaha Lani 223.
The Location:Perfectly positioned to accommodate everyone's interests, the Coconut Coast is flanked by epic coastline threaded together by the Ke Ala Hele Makale coastal bike and walking path. Just a 7-minute walk along the path or the golden sand beach brings you to...
Kona Makai 6301: Delightful Oceanview Condo w/ AC, Shared Pool & Spa
Oceanfront Living Meets Island Adventure – Your Ideal Kailua-Kona RetreatExperience the beauty and comfort of Kona Makai 6301, a beautifully maintained oceanfront condominium just one mile from the heart of Kailua-Kona. Located only 30 feet from the water's edge, this...
Bright & spacious home near the ocean w/ gas grill and patio - newly remodeled
Ka Honu LaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This newly-remodeled home will immediately put you into a state of aloha the moment you open the double doors, welcomed by...
Ground-Floor Condo w/Free WiFi, Private W/D + Shared Hot Tub, Pool, & Gym
Pili Mai 1AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience a new Hawaii? Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in...
Kauai -Anahola Beach Front
NA PAINA is a spacious 2-story cedar house nestled in ironwood trees right on the sandy beach at Anahola Bay. This classic old-school beach house has two decks and spectacular ocean views. Anahola is a secluded bay, located in a small residential community and has a...