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.
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!
Enjoy the 5th Night Free for stays between now and December 15, 2025. Reservations must be made by August 31, 2025. *Applies to new reservations only. Property Highlights • Five minute walk to three world-class beaches, including Kapalua® Bay, rated the "Best Beach...
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...
R413-Pool-Spa-Beach-Turtles-Southside-Ocean Access-W/D, 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 by Gather, an inviting three-bedroom and a den in a two-floor vacation home nestled in the scenic community of Princeville, Kauai. Casa Makara offers stunning views of lush mountains and a pristine golf course, comfortably accommodating up to six...
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....
Marriott Ko Olina Beach Club 1BR Villa, Full Kitchen. Includes Tax, Parking
The Marriott Ko Olina Beach Club Resort offers daily and mid-week availability. ( 3- 5 Night Minimum ) Rates are based on weekly stays in USD and will vary by week, view and season / holiday. Daily rates will increase for 3 - 7 night stays. Marriott owner services is...
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...
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...
Gorgeously Updated - Kihei Surfside #113 - Groundlevel Oceanfront Condo
Kihei Surfside #113 – Fully Renovated Ground-Floor Ocean View Condo with A/CEnjoy comfort, convenience, and coastal beauty at Kihei Surfside #113—an ocean view, ground-floor condo that underwent a complete renovation in May 2022. Located steps from the water’s...
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...
Chic Condo Near Waikiki Beach - Free 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...
Charming condo with amazing ocean vistas, full kitchen, W/D & sunrise-view lanai
Sealodge at Princeville J3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'It’s all about the spectacular views at this cozy and relaxed single-level Princeville condo! Begin your...
Stunning Estate Property In Gated Community Steps From The Ocean
Welcome to our 5 star rated vacation home. We call our home Forever Sunsets because with just a short walk to the water in our gated community you can watch the sunset every night. You are also a short 600 yard walk to Magic Sands Beach, the most popular sandy beach in...
Beaches, Beaches, Beaches! West Molokai. Remote and Private. Hawaii's best.
Kepuhi Beach Resort Condo. Corner ground floor 1 BR. Living and Bedroom both face the awesome blue ocean view which is backdrop to the 11 acre green grounds full of mesmerizing swaying palm trees. 800' to water’s edge on Kepuhi Beach. Short 1/2 mi. walk to famed...
Wailea Beach Villas | PH301
Wailea Beach Villas Penthouse 301 offers an unparalleled vacation experience with its luxurious 2,500 square foot ocean view suite. Situated on the third floor and accessible via a private elevator, this penthouse ensures privacy and tranquility. The suite features...
SPECIAL DEALS Honua Kai 8th Flr Remodeled Suite in Paradise ONE-OF-A-KIND
Aloha! We welcome you and your family to our Beach House decorated Suite, Konea 830 at Honua Kai.~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~West Maui is reopened and we are happy to host you! ~~~~~~~~~~~~~~~~~~~~~~~~Updates:This unit uniquely stands out above the rest! Fresh Paint &...
Pipeline Beachfront House - Sleeps 12 Guests
Minimum 30-day consecutive rental required. Please contact the Host for availability. Located right on the beach where dreams are made for many professional surfers every winter. This three-story house has four bedrooms and four and a half baths. Enjoy amazing ocean...
Breathtaking 3rd-floor 3bd oceanfront condo
Stunning oceanfront views with Molokai and Lanai as your backdrop. Noelani 302 is a spacious 3-bedroom, 2.5 bath condo that is perfect for families and groups. It offers a fully equipped kitchen including dining space inside and outside on the private lanai. This unit...
Private ground floor villa with bbq and golf course view.
Waikoloa Beach Villas K2, is excited to be on the vacation rental market. Updated design with new appliances gives this first class home the edge and excitement to enjoy your vacation in paradise. 2 bedroom, 2 bathroom with full size kitchen to provide you with the...
Maui Sunset A307 Fabulous Oceanfront Complex Featuring Magnificent Sunset Views
Recently renovated in July of 2024, featuring new cabinets, vanities, countertops, appliances, fixtures, doors and painted throughout. Spend your vacation on the beach, at the beautiful Maui Sunset complex, where our lovely, one bedroom condo is located. Take a relaxing...
Paradise Retreat, POOL, Hot Tub and AC with ECO energy!
Paradise Retreat is your own private resort on Hawai'i’s Big Island. Relax and enjoy the swimming pool and hot tub in our private, fully enclosed back yard. Lounge poolside in the sun-soaked chaise chairs or stay cool on the covered lanai. In the evenings, enjoy...
Bamboo Valley Inn 2BR/1BA Permitted
Maui County Bed and Breakfast Permit #BBPH 20090014,TA-200-805-1712-02 Make sure you check as most rentals do not have permits from Maui County to operate and may be shut down. If you are looking for peaceful Hawaii away from the crowded resorts and neighborhoods, look...
Ocean Front with stunning views! Includes beach gear! Halii Kai 15H
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 15HPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: 2 Twin BedsLiving Room: Sleeper SofaAmenities:Beach...
Vacation In Paradise At Makaha Area in a Legal NUC
Come to Paradise on Earth at the Hawaiian Princess located in the dry, sunny Makaha Area in West Oahu. The condo is on a secluded 1/3 mile pristine white sand beach overlooking the gorgeous Turtle Cove. Celebrate a special occasion, romantic getaway or just come to...
The Best of Kamilo, Mauna Lani - Largest Model Home, Guest House, Pool, Spa!
Kamilo 331 is a resort home offering 4 luxurious bedrooms and a private solar heated pool and waterfall spa. Kamilo 331 is one of the few Hoku B floor plan models, the largest and highest-priced home available in the Kamilo community. This single-level family home...
Oceanfront stunning corner condo
You'll enjoy Papakea Resort A101-A102's amazing oceanfront location and the beauty of Maui from virtually every room! This lovely and unique 2-unit corner property was converted into one large 2-bedroom, 2-bathroom condo with over 1,300 square feet and a split air...
Wailea Ekolu 703 / Beautiful Ground Floor, Expansive Lanai, Ocean Views & Aircon
Indoor outdoor living with Fantastic Ocean views from this spacious 2 bed/ 2 bath ground floor private condo! Enjoy early morning walks or a relaxing dip in the pool. This unit has been completely remodeled from top to bottom, all new windows and double pane sliding...
Ocean-Marina and Fireworks Views at Ilikai Marina Short Stroll to the Beach
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.July 11, 2025ILIKAI MARINA NOTICE — Spalling Work UpdateSpalling repair on the Ocean/Marina-facing side is nearing completion, but...
Hard To Beat Oceanview 2Br/2Ba - Newly Renovated - Saltwater Pools & Pickleball!
CANCELLATION IS POSSIBLE!! See standard cancellation terms outlined in our Rental Agreement. We are also willing to work with our guests to make their vacation possible, especially with Covid issues and potential travel restrictions.You’re invited to stay in our Kihei...
TOP FLOOR CORNER PRIVATE STUDIO, AFFORDABLE WAILEA, WALK TO BEACH
Last minute DISCOUNTED RATES We appreciate your support as a small, self managed Maui family owned rental instead of renting from a large mainland management company. Enjoy sunny South Maui in our lovely studio top floor condo at the award-winning Grand Champions...
Two-Story Private Home at Kamilo - Grill Deck, Pool & Sunset Views!
Beautiful private home with a heated pool, spa and 2,400 square ft. of interior living space in a prime resort location. This 2-story dream home overlooks the famous Mauna Lani golf fairways and features vaulted ceilings, exotic hardwood floors, emerald granite counter...
🏖️Ocean Front | Central AC | Private Pool | Concierge Included | vrKCV
vrKCV - Holua Kai 21, Professionally Managed by Kona Coast VacationsThis stunning oceanfront home is situated in Kona on the Big Island, offering breathtaking, unobstructed 180-degree ocean views and the best of island living. Overlooking the second, third, and fourth...
*A/C* Elegant Single Story ~ Plantation Home
Absolutely Beautiful Inside & Out... Plus New Air Conditioning :) This Tropical Plantation Home offers 4 Bedrooms. It is Elegant & Richly Appointed with Rare Solid Hawaiian Koa Wood Flooring and a Spacious Floor Plan. The Sliding Glass Doors Surround the Living Room and...
Tropical Luxury Villa: Indoor-Outdoor Living, Gourmet Kitchen & Spa Bathrooms!
Stay longer, enjoy more! Book 10+ nights and receive a free mid-stay clean. Book 14+ nights and get one night free!This property is hotel zoned, and not being affected by the recent proposed legislation.Ho'olei 24-6! Gorgeous 3 Bedroom Garden View Villa! Luxury at its...
Spacious Wailea Townhouse + Ocean Views! Ekahi 48A
Welcome to Wailea Ekahi 48A, offering the largest floor plan with gorgeous ocean view! This beautiful 2 bedroom/2.5 bath is the perfect retreat for couples or families. The first level of this spacious condo features a sunken living room complete with convertible queen...
Maui Resort Rentals: Groundfloor Interior Honua Kai Konea 143, Huge Lawn Area, Steps to Pools/Beach/B.B.Q.s!
Enjoy one of the most convenient ground floor locations at Honua Kai in the highly sought interior courtyard of the Konea Tower. Konea 143 offers a spacious 1315 square feet of living space and convenient interior ground floor access to the pools, beach, and BBQs. The...