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.
Palms at Wailea 1203, offers the perfect location in Wailea!
Palms at Wailea 1203, offers the perfect location in Wailea. This 2-bedroom/2-bath ground-level unit surrounded by lush landscaping makes this a great Hawaiian retreat!Ideally situated just uphill from gorgeous Keawekapu Beach, The Palms at Wailea is an...
Rustic Cabin in Volcano Village
Rustic Cabin in the rain forest, located 5 miles to Hawaii Volcanos National Park.The quaint country cottage will draw the image just right.House is tailored to rejuvenate and enjoy seclusion in the forest.You can expect peaceful surroundings suited to relax and boost...
Exclusive Beachfront Cottage, Private, Ocean Views, AC, WiFi, Whale Watching!
On Maui's sunny south shore, is the romantic Honu’ea cottage, where quiet peaceful living is a way of life. Honu'ea (Hawksbill Turtle) is named after the endangered turtles that come and nest on the sandy shores in front of the property. Honu’ea is perfect for...
Anahola Beach Hale - Tropical Beachfront Home with AC
This quintessential tropical beachfront home with 4 bedrooms and 4 baths with air conditioning throughout is surrounded by lush tropical foliage and swaying palm trees is located on one of Kauai's most beautiful beaches. The expansive stretch of white sandy beach...
Hualalai Fairway Villa 104D - overlooking the 15th tee
Upper level 2-bedroom, 2-bath villa overlooking the 15th tee of the Hualalai Golf Course with stunning Mauna Kea, Island of Maui and horizon views of the ocean. Designed by Honolulu-based Architect Warren Sunnland, the Fairway Villas at Hualalai are located within a...
🏖️Peaceful and Private | Pool | Ocean Views | vrKCV
vrKCV - Nakukui Elua, Professionally Managed by Kona Coast VacationsNakukui Elua- Peaceful and Private with Pool and Ocean Views!Flowering hedges, rock walls and wooden fencing surround your island home. Located on 3/4 acre lot in the gated community of Kahakai Estates...
Only thing between you and the ocean is the Beach! Top Floor, unobstructed view
Newly renovated condo with 2 TV's, WIFI, Washer & Dryer, Dishwasher, Stove, Fridge, Keurig Coffee Machine, Nespresso Machine and Microwave. One bedroom has a king size bed and the other has a queen size bed. 55" Flat screen smart TV in Living Area and 40" Flat screen...
Papakea OceanFront Resort - Beautiful Two Bedroom Ocean View Suite
Papakea Resort Maui provides amenities like dry cleaning/laundry services and 2 hot tubs. Guests can connect to free in-room WiFi.Other perks include:• 2 outdoor pools• Free self parking• Barbecue grills and concierge servicesRoom featuresAll guestrooms are...
Ocean View Villa, Heart of Wailea, Ho'olei L1 23-1, Third Tier
This villa at Ho'olei was renovated in 2024. The renovations are extensive. New extra large kitchen island with ocean view seating: all new appliances in the kitchen: new stone counter tops throughout the home: new cabinets throughout the home: new tile in all the...
Wai'ula'ula: You Can't Beat This View
BEST LOCATION AND VIEWS! Wai'ula'ula A101 is located near the exclusive Amenity Center and offers panoramic and unobstructed views of the ocean, golf course and sunset.This unit is located on the ground floor and tastefully furnished & KID FRIENDLY.Please inquire for...
Executive Center Studio with Kitchenette, secure building pool, FREE PARKING
Updated downtown studio with (Free Parking a $50.00 Value per night can go in and out no charge/ dedicated parking stall few feet away from elevator ) located in the Aston Executive Centre. Enjoy hotel amenities including 24 hour security, pool, hot tub, on site laundry...
The Ridge House at Mauna Lani - Brand New Champion Ridge Estate
Enjoy the Big Island in style in this sprawling 5-bedroom luxury estate in the prestigious Champion Ridge at Mauna Lani community. Newly completed in 2024, this ultra-modern estate offers privacy, a spacious floor-plan and plenty of fantastic amenities to make your...
Luxury 1BR Beachfront Condo on Sugar Beach unit 505
This high end, remodeled Sugar Beach Resort condo offers unbeatable views of the sparkling ocean from North Kihei, Kahoolawe, Molokini and Makena.Take a dip in the heated pool, or enjoy long walks on Maui’s renowned Sugar Beach and a swim just steps from the condo....
New Listing: Breathtaking Oceanfront Corner Unit w/ Sweeping Views Central Ac
Only four units like this at Papakea Resort— and this one’s a stunner. Spot turtles and monk seals right from the balcony of a 3rd-floor corner unit — wraparound lanai and 180° views of the Pacific included. You're 30 feet from the water and 100 yards to the...
The Love Shack island getaway - minutes from Waikiki
The Love Shack Beach House - all the convenience of Waikiki without the hassle and noise. Walking distance to Waikiki, Diamond Head, beaches, the zoo, Kapiolani park, surf spots, snorkeling, swimming, great restaurants & bus stops. No need to rent a car if you don't...
Hawi Hideaway, quiet home in small country town
Welcome to Hawi Hideaway,2 bedroom, 1 bath home in Hawi. Sleeps 6, walking distance to main street, Saturday farmers market, coffee shop, boutique stores and galleries. Our home is tucked away off the street in a beautifully landscaped yard. There is a mango and orange...
Napili Oasis Hideaway, Amazing Oceanview in Maui
Welcome to my beautiful oceanview condo, in one of a kind boutique condominium. Wake up to ocean breeze and view from lanai, watch turtles and sunset on lava rocks, feel at home falling asleep to the sound of the ocean every nightLocated on the 2nd floor at Napili...
KaMilo Luxury Living - Hale Lani. Bikes and Beach Gear included.
KaMilo Luxury Living – Hale Lani Welcome to Hale Lani at KaMilo, a luxurious home for your Hawaiian holiday. This four bedroom three and a half bath townhome is perfect for large families or friends to gather for a Hawaiian vacation. Beautifully and comfortably...
Masterfully Renovated Ocean View Unit in Waikiki
One of our best listings! Bright and Light One Bedroom, One Bathroom and One Parking (Max 6ft) at the Waikiki Banyan. Full of natural light during day! This partial Ocean View unit in the heart of Waikiki will make your stay in paradise a memorable one.Total of 3...
Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops
Summary:Location and Quality! You will feel the relaxed beach vibes from the very first step walking into this tastefully updated & beach luxe unit. Directly sit across the famous Cove surf spot & in the middle of all, you will be memorized by the ocean waves along with...
Hale Wa'a | Luxury Kauai Vacation Home
Welcome to Hale Wa'a (House of the Canoe), a stunning 4-bedroom, 3.5-bathroom vacation rental nestled in the prestigious Kukui'ula community on Kauai's southern coast. This brand-new modern home, located in the Kaulu neighborhood, seamlessly blends contemporary design...
Maui Resort Rentals: Marriott't Maui Ocean Club 2BR Mountain/Garden View Villa - New Lahaina Tower
2 Bedroom Mountain/Garden View Villa at Marriott's Maui Ocean Club – New Lahaina Tower! With its premier location, luxurious accommodatiWith its premier location, luxurious accommodations, and sprawling tropical grounds, Marriott Maui Ocean Club is a perennial Maui...
Beachfront Villa and Guesthouse
Escape to a private Puako beachfront estate & guesthouse on Hawaii’s Big Island. Ocean views, steps from snorkeling, luxury amenities & sunset bliss await.Hale Ama is an Oceanfront home located in the magical Puako on the Big Island of Hawaii. Puako is one of the...
Quiet & Immaculate Molokai Condo, 2nd Floor End Unit, Ocean Views + Free Car
ALOHA! The Condo: This is a one-of-kind 2nd floor, 565 sq.ft. ocean view condo with to-die-for sunsets. Open floor plan with loft. hard wood floors, granite counter tops, 1 queen master bedroom and 1 double bed in loft. In condo washer and dryer. Fully supplied kitchen...
Hualalai Waiulu Villa 137D
This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet of living space and a 414...
NOTHING BUT OCEAN VIEWS! Remodeled, AC, direct ocean front, large 2bd/2bth
Our unit is the 'FIVE STAR' condo in this building complex located in N. Ka'anapali/West Maui. Premier unit, front & center ocean & island views all from the 3rd fl. The condo is specifically designed as an adult only unit, but we do allow babies w/cribs or packNPlay...
Shores at Waikoloa Beach Resort 315
Summary:This tropical top floor penthouse offers beautiful resort views and peek a boo ocean views that look towards the Hilton Waikoloa hotel. The Waikoloa Beach Resort features luscious greenery, koi ponds, a shared swimming pool, a fitness room, and BBQ stations to...
Wailea Luxury Resort Vista
Summary:Completely remodeled (Sept 2023). Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful...
Steps to the Beach! Ocean Front Condo! 5 Star Views! Centrally Located!
Steps To The Beach! Ocean Front Condo! 5 Star Views! Centrally Located!Aloha-We bet that because you’re reading this you’ve looked at the descriptions of many vacation rentals on Kauai. Likely all of them gave glowing descriptions of how wonderful they are –...
Private Paradise: Ocean-View Kukuiʻula Luxury Home With Pool and Spa
Welcome to Ke Kai Nui (“The Great Sea”), an extraordinary 4-bedroom, 4.5-bath island sanctuary in the exclusive community of Kukuiʻula, on Kauaʻi’s spectacular southern coast. With its soothing blue tones and coastal touches throughout, the home embodies...
❤️PiH❤️ Mauna Kea Sunsets ★Ocean and Golf Views★Optional Mauna Kea Hotel Privileges
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Mauna Kea Sunsets, a part of our Hawaiian Luxury Collection. Mauna Kea Sunsets at the Mauna Kea Resort Kumulani complex has stunning views of golf, ocean and mountains. This two bedroom upper-level unit is...
New! Upgraded Kiahuna 425 Plus Athletic Club
Rare Find with A/C at Kiahuna Plantation – Newly Upgraded & Steps from the BeachKiahuna Plantation #425 | 2nd Floor Corner Unit | Building 41Looking for cool comfort in paradise? This beautifully updated condo at Kiahuna Plantation now features brand-new A/C — a...
2 BR Luxury Oceanview Condo in Kukuiula
Kainani #1 is a 2-bedroom, 2-bathroom villa nestled in the heart of paradise, offering an unparalleled experience of comfort, convenience, and tranquility.As you step through the ground-level entry, you'll be greeted by the seamless fusion of indoor and outdoor living...
SALE! REDUCED 489nt 4/26/-5/2 2bd2bth condo HUGE 1680sf,50ft to ocean,AC,views
We are very saddened by the devastation and loss of life in Lahaina. Our condo is NOT IN Lahaina, we are 6 miles from it. Thankfully since we are not close to Lahaina, our condo, complex, and all surrounding areas are in the same pristine condition as it always has...
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
*Please note that per Maui county law, that two adults and two minors are allowed per bedroom. We are allowed to host up to 4 adults and 4 minors for a total of 8 guests. This is a private top floor unit of a 2 level home. Our favorite aspects of the home are:*Large...
Oceanfront Kailua-Kona Home, Walk to Kahaluu, Wifi & AC
Welcome to Hale Lula o' Nai'a – "House of the Dolphins" – your oceanfront retreat on scenic Alii Drive!Ideally situated just north of Kahalu'u Beach Park in Kailua-Kona, this prime location offers easy access to surfing, paddle boarding, and snorkeling.Designed for...
2 bed/2 bath luxury condo in sunny Poipu with AC
*** Welcome to our Regency Villa in Poipu *** NEW LISTING!We recently bought this luxurious 2 bedroom condo and fell in love with the garden views, chic decor and the prime location. The boutique resort is one of the newest in Poipu. You will love staying here with your...
Charming Oceanside 2-bedroom condo with A/C in fabulous Kapaʻa
Located in Kapaʻa, this 2-bedroom condo offers an enjoyable stay with 1 queen bed and 1 king bed. The property comes with essential amenities like WiFi, AC, and a washer/dryer. Guests can relax in this adorable and peaceful space, perfect for both short getaways or...
Luxurious High floor Waikiki Landmark Condo, Ocean & Diamond Head views!
Waikiki Landmark is Waikiki's premier condominium, located at the Gateway to Waikiki. The contemporary architecture reflects a pair of triangular towers, the Makai Tower (ocean) and Mauka Tower (mountain) this two bedroom unit is located on the Makai Tower and is...
Surfers & Sunsets-Kona Reef Ocean Front Unit
Watch the Surfers from Your Lanai - Kona Reef Ocean Front UnitLight and Airy with direct Ocean Views from the Lanai, Living and Kitchen areas. Large Ocean Front 611 square foot condo with a full 128 square foot Lanai. This fully equipped Ocean Front 3rd floor condo is...
Quiet Studio Vacation Rental on the Beautiful Puna Coast
This private studio and thoughtfully equipped with everything you need for a comfortable stay. You’ll have your own entrance, a comfortable (new) queen bed, and bathroom. The space also features an outdoor shower — perfect for tropical climate. The studio includes a...
Luxurious 4 Bedroom Retreat, Private Pool, Located in KuKui' Ula Community.
Situated on the upper tier of the Kainani neighborhood in the beautiful Kukui'ula Community, this exquisitely designed, newly constructed custom home, features custom imported teak flooring, cabinetry, vanities, trims, natural wood, stone, lava rock, and hand selected...
Maui Resort Rentals: Honua Kai Konea 932 – Upgraded 9th Floor 2BR w/ Mountain & Partial Ocean Views
Konea 932 is a remarkable 2BR/2BA suite boasting an impressive 9th-floor corner location. It offers the best of both worlds with views of the tranquil blue Pacific Ocean as well as the majestic West Maui Mountains. Oversized picture windows bring the ocean views into...
Boutique 1-bedroom condo in Waikiki! WiFi, AC, Pool, Hot Tub, BBQ Free Parking
Enjoy a pleasant stay at this newly rennovated 1-bedroom condo in Waikiki, Honolulu with Free Parking. This 11th floor home features 2 queen beds,a pullout sofa-bed, Japanese tolilet, magnetic arm and rainshower head,perfect for a small group of guests and families....
Oceanfront Maalaea Harbor Two Bedroom Condo within walking distance to beach
We are thrilled to announce the completion of our condo's remodel in January 2025—everything in the unit is brand new! The property offers one private parking spot, with additional off-street parking available. Located on the second floor, the unit features easy...
Modern and Cozy Ocean View Condo - 10% Discount on 7 days Booking
Sugar Beach Resort sits steps away from the Pacific Ocean in North Kihei and a 5-mile white sandy beach that fronts the property. Guest enjoy taking morning and sunset beach walks while enjoying the panoramic view of Pacific Ocean. Watch Humpback whales visit the...
Ko Olina Beach Villas - Beachfront (Beach Tower 709)
Our spacious 1,500 square foot suite is the only beach-front penthouse available for rent at the prestigious Beach Villas Resort in Ko Olina and the only privately rentable condo with panoramic ocean views from every room.Watch the video of our property -...
Huge Luxury Condo | partial Ocean View on Beach 1 BD
Condo, 1 Bedroom, 1 Bath, (Sleeps 1-4) Aloha! Welcome to Paradise! Important: Although this is a privately owned vacation rental home this complex is zoned "Hotel" so not part of any potential changes to vacation rental property use. Welcome to the Honua Kai Resort and...
Mauna Kea Villa 3037 - Architectural Island Estate
This dazzling, single-level, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living and Sonos system, a chefs' kitchen with Wolf and Sub-Zero appliances/wine refrigerator, a dining area with adjoining wet bar, a...
Beautiful Ground Floor Golf Villa @ Fairway Villas Waikoloa
Welcome to our spacious 2 bedroom/2 bathroom premium ground floor villa overlooking the fourth hole of the Robert Trent Jones II-designed Waikoloa Lakes Golf Course. The Fairway Villas complex is a part of the Waikoloa Beach Resort area, located just 20 minutes north of...