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.
Luana 15D: Upper-Floor 3 Bed Villa w/ Private Lanai, BBQ & Garage at Honua Kai
Welcome to Luana Garden Villa 15D, your personal slice of paradise located on the upper floor of building 15 in Enclave Three at the prestigious Honua Kai Resort & Spa in Kaanapali, Maui. This spacious 3-bedroom, 3-bathroom villa offers 2,047 square feet of luxurious...
Luxury Zen Polynesian Penthouse
Prepared to be Zenned, Aloha style!!! Penthouse accommodations starting at $260/night (with extended stay discounts available) and on Island coincerge available. State of Hawaii STVR ID #19-375711; and, GE/TA # 069-450-8032-01.Located just 20 minutes north from Kona...
Ohana Haven · Beach, Surf, Golf, Shop! Comfy beds &streaming TVs
Ohana Haven is situated in Waikoloa, just 1 mile from the beach! This villa has two beautiful pools with waterfalls and a jacuzzi to soak in after a day hiking in the gorgeous jungles or across the lava rock. There are gas BBQ's next to the pool for easy access while...
DISCOUNTED RATES! 202 Quaint 2nd floor with private lanai
You can enjoy your coffee on the private lanai while watching turtles (honu) and whales, during the winter season. Sunsets are amazing every single day. Every night at sunset, Kulakane tradition is to blow the conch shells at sunset. You will find a conch shell in your...
Stunning Oceanfront Sunset-Bali Hai Views with A/C + Hideaways Beach below
Welcome to Hale Honu Aloha ("Home of Turtle Love") at Puu Poa - An updated spacious two-bedroom, two-bath condo on the ocean bluff of Princeville that accommodates up to 4 people. Overlooking the Pacific Ocean and directly adjacent to 1-Hotel Hanalei Resort (formerly St...
Laule'a 5: Luxury Home w/ Infinity Pool, Spa & Stunning Views
Set within the prestigious Mauna Lani Resort on Hawai‘i Island’s Kohala Coast, Laule‘a at Mauna Lani Resort #5 is an extraordinary luxury residence offering modern elegance, expansive indoor–outdoor living, and breathtaking ocean and fairway views. With over 4,000...
Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508
Wailea Elua #1508 – Partial Ocean Views & Comfort Near PoolSet within the prestigious Wailea Elua Village, Wailea Elua #1508 offers an ideal balance of peaceful luxury and island convenience. This spacious 2-bedroom, 2-bathroom condo features partial ocean views, a...
Beach Paradise: 6 BR Kihei Beachfront Home with Pool
Legal Vacation Rental: Permit Number STKM2020/0002HOLIDAY SEASON: There is a 7 night minimum during the period Dec 18-27. There is a 10 night minimum during the period Dec 27-Jan 10.Chill Out with friends or family in this spacious two-story Maui beach house which...
This luxurious 3BR/3BA residence is conveniently set within Enclave Two of the Luana Garden Villas. Villa 9C's north-facing orientation offers a shady respite from West Maui's legendary sun, and its designation within our "Elevated" collection offers a level of privacy...
Paradise vibes awaits @ Hali"i Kai, ocean front resort in Waikoloa Beach
23H Island inspired décor to give you all the feels of Hawaii. This 1400 square foot 3 bedroom, 2 bath condo is located in the most desired resort on the Big Island, Hali'i Kai at Waikoloa. Situated in the coconut grove amongst the relaxing tropical garden, 3 outdoor...
Surreal ocean front view and breezes at Hali'i Kai at Waikoloa Beach Resort
11C is a prime location to enjoy those seamless Hawaiian sunsets. Situated right by the ocean, you will be able to smell the salt air as the winds of Waikoloa breeze on by. The condo is footsteps away from the Ocean Club, where you can enjoy the water front 4 tier lava...
Waiulaula Villa Mauna Kea -Previous Model - Ocean, golf & mountain views!
Welcome to Wai'ula'ula' at the Mauna Kea Resort!Professionally decorated former model home with mahogany trim and stone upgrades, and now current newer updates and furnishings, offers breathtaking ocean, Maui, and Kohala Mountains views! Located overlooking the Westin...
Ocean View. Central AC, Parking is available. Multiple cottages to choose.
~Beautiful ocean, beach view ️ ~Balcony has dining furniture ️ ~Quiet central AC, quiet building ~Larger size cottages’s bedroom has view.~2 minutes walk to Duke‘s statue and Waikiki Beach ~Provide all kinds of kitchen appliances and cooking utensils. ️ ~Grocery stores,...
KOA RESORT 3-F LOCALLY OWNED AND OPERATED Spacious beautiful ground floor condo
As owners who manage our own property, our commitment, to our guests, is to have a clean and comfortable experience.Our Ground floor unit is easy to access from the parking lot and all the amenities at Koa Resort. This One Bedroom/One Bath spacious condo is in a perfect...
Welcome to 3 Luana Garden Villas 1A,1C& 1D Oceanfront resort Partial ocean Views
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful Luana Garden Villas at the Honua Kai Resort.This listing is for “three” separate neighboring villas, which is perfect for a multi-family vacation. Luana Garden Villas is the final phase of Honua Kai Resort...
K L V R Welcomes you to 4 Luana Garden Villas Building 11 in Oceanfront Resort
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful Luana Garden Villas at the Honua Kai Resort.This listing is for “four” separate neighboring villas in one building, which is perfect for a multi-family vacation. Luana Garden Villas is the final phase of...
KLVR welcomes you to Honua Kai Luana 11A Oceanfront Resort Resort and POOL view
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful garden level Luana Villa at the Honua Kai Resort. This luxurious villa is located within a private garden enclave at the spectacular, beach front, Honua Kai resort. This villa boasts 2047 sq. ft. of...
Welcome to Luana Villa 9D Oceanfront Resort, Upstairs, Mountain/Pool view
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful upper level Luana Villa at the Honua Kai Resort.This luxurious villa is located within the 38 family-friendly acres of the Honua Kai Resort & Spa, designed with relaxation and memory-making in mind,...
Gorgeous Fairway View Home w/Shared Pool, AC & Relaxing Lanai: Kamilo #123
Mauna Lani KaMilo #123 – A brand-new designer home in the heart of Mauna Lani Resort, Kamuela, offering over 2,400 SF of luxury living space. Whether you’re here to relax or entertain, this 4-bedroom, 3.5-bathroom home accommodates up to 10 guests, with ample room for...
Royal Mauian 309 - Direct Ocean Front, Renovated, Seconds to the Beach, Split AC
A unit renovation will take place in unit 310, next door to this unit, beginning April 7th through September 15th. Please expect noise as well as the potential for dust and debris during work hours. ------------------------------------------Royal Mauian 309 is a newly...
Two Bedroom Ocean View Deluxe Luana Kai Resort A203
Luana Kai A203 is a two bedroom/ 2 bath oceanview. Enjoy the spectacular view while dining on the lanai. This condo has a King in the master with two twin beds in the guest bedroom, and a sofa bed in the living room. A203 does NOT have AC. Includes Wifi, cable Tv, and...
Luxury Upcountry retreat with breathtaking views!
PermitsBBMP2019/0006 & SUP2 2019/0003GE-081-730-0480-01 & TA-081-730-0480-01This is a BnB not a STRHOwners live on property.Aloha, sorry but at this time we are not hosting to families with children younger than 12 Mahalo.This is a NO SMOKING property. Mahalo. Our...
This luxurious, 3BR/3BA residence is conveniently set within Enclave Two of the Luana Garden Villas. Its southern orientation offers a bright, inviting setting, and its designation within our "Elevated" collection at Luana Garden Villas offers a level of privacy...
Maui Resort Rentals: Honua Kai Konea 239 - Upgraded Ocean View 2BR, Deluxe Corner Suite
Konea 239 is among the most sought-after two-bedroom floor plans at Honua Kai. What distinguishes this column in the Konea interior is the direct ocean views from virtually every interior vantage point of the suite. This premier two-bedroom boasts a spacious 1325 sq ft...
Beachfront Kihei! A True Beachfront Experience!
Unbelievable main floor beach front condo. Unit 5 of Kamaole One is a 2 bedroom, 2 bathroom, 1100 + sq ft corner unit condo perfect for 4 people. Located in an unforgettable location directly on family favorite Charley Young Beach. The beach features a sand bottom,...
Oceanfront Remodeled-30 Feet to Ocean-CENTRAL AC-Highly Sought After
One of only a dozen like it at Papakea, this oceanfront corner unit wraps you in 180° views of Moloka’i, Lana’i, and the deep blue Pacific. Sip coffee from the lanai, prep dinner in the gourmet kitchen, or catch whales mid-breach while stretched out on the designer...
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Whaler`s Inn -Nautical Magical
Whalecome and Aloha!You looking for an authentic Hawaiian Nautical experience? Let the Whaler`s Inn be your perfect spot to relax, set your sails with us and put down your anchor. We are located right in Downtown Hilo just Minutes away from Shops, Restaurants and just a...
Discount Week Rates! Elua Premier 2-Bedroom Front-Row... Oceanfront Unit!
Ulua Beach Premier 2-Bedroom Oceanfront Unit...Unobstructed Ocean Views!Welcome to Wailea Ulua #1002! This recently renovated luxury beachfront 2 bedroom/2 bath residence is located in the heart of Wailea on Maui Sunny South Shore. Within steps of the unit you are on...
We are welcoming guests back to Lahaina Roads, our property and apartment have been updated over the past two years and we are excited to greet our guests with heartfelt Aloha!We have worked very hard to provide you with a ‘home away from home’ atmosphere! After an...
Simply Beautiful Waikīkī Apartment
*MONTHLY RENTAL* Stay close to Waikīkī Beach, 5 minutes walk to the sand. Our stylish 2-bedroom space is in a secure building with free parking, pool, jacuzzi, sauna and rooftop BBQ area. Highlights include a big balcony, full kitchen, 3 air-conditioners, double shower,...
Kaua'i Island Paradise in Princeville Sleeps 6
Entire Townhouse 1,100 sq. ft. end unit with 3 bedrooms 2 baths for 6 guests:1 king, 1 queen, 1 queen with 2 Full baths. Relaxing atmosphere Townhome with beautiful foliage and mountain views from every window. A mile stroll to a secluded lush and green year round trail...
Poipu Prime Location near Hyatt - Well-Appointed Home with Hot Tub in Courtyard
Located in the Bayview Neighborhood of the upscale Poipu Kai Resort here on the sunny South Shore of Kauai, our guests have access to the Poipu Kai Resort pool and tennis courts. This 3,800 sqft two-story home is just a short stroll west along the tropical walkway to...
Waikoloa Colony Villas, 2 story townhouse on Golf Course!
Beautiful 2 bedroom private villa with tranquil golf course views is the perfect place for a relaxing vacation! Due to covid-19, the property is disinfected and cleaned in preparation for every stay.The Waikoloa Colony Villas is a gated condominium community on the...
The Villas at Poipu Kai #E210 By Parrish Kauai- Premier Villa with AC and walkab
The Villas at Poipu Kai are one of the newer luxury condominium resorts on the South side of Kauai in Poipu. These spacious and upscale condominiums are part of the Poipu Kai Resort that offers access to additional recreational amenities to all in the Poipu Kai...
Papakea Paradise, G102, 2 Bedroom & 2 Bathroom, Ground Level, Air Con, Specials!
The much coveted ground floor, one level, 2 bedroom - 2 bathroom floor plan at Papakea. No steps! Also, brand new ductless air conditioning system in both bedrooms and living room / kitchen area. An amenity not all of the condos have! AND PAPAKEA IS NOW A NO FEE...
LAST MINUTE AVAILABILITY IN APRIL $ 100/Night DISCOUNT! 2 BR Ma'alaea Surf B4
Located just steps from the shore on Sugar Beach in beautiful Ma'alaea Surf Resort, this remodelled two-bedroom, two bathroom ground floor condo is your perfect vacation hideaway. The unit was taken to studs and completely rebuilt in late 2022 and every element was...
Watch the whales and spectacular sunset views from your balcony!!
.This oceanfront resort in Poipu Beach Kauai, features amazing close views of the ocean, you are less than 100 yards from the ocean and less than a 5 minute walk from an amazing kid safe beach. Walk to stores and restaurants and many other cool shops at Kukuiula Village...
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
• Oceanfront• Split A/C units• King bed• Remolded Feb 2020• Beach access from condo complexFully remodeled in February 2020, this bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei unit 213 welcomes you! This second floor condo is...
Rare Deluxe Ocean View Gem with 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...
119 night April disc Alii Dr Fully Equipped, Pool, Jacuzzi, BBQ, High-Speed WiFi
Welcome to Kona Bali Kai Ocean and Surf location! Your dream vacation awaits at our beautiful condo located in a prime spot close to downtown, Magic Sands Beach, and Kahalu'u Bay. Picture yourself opening the slider and listening to the soothing waves at night. Our...
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...
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 minutes to the beach, and a short drive...
S. Kihei spacious garden condo, 2 lanais
Escape to our peaceful 850 sq ft ground-floor resort condo! This private, quiet end unit features 2 outdoor patios, a Cal King master, and 2 sofa beds. Enjoy a fully equipped kitchen, in-unit laundry, and beach gear, such as chairs, towels, snorkels and toys. Located...
Kauai Exclusive - Pili Mai 7B - Four Bedroom Suite - AC, Pool & Fitness Center
Summary:Spacious 4-bedroom, 3.5-bathroom condo features two master bedrooms with En Suite bathrooms, upgraded amenities such as A/C, Marbau flooring, granite countertops and Bosch appliances, a washer, dryer and much more!The sparkling new Pili Mai Resort is an...
❤️PiH❤️Secret Tropical Hideaway★ Bikes/Beach Toys ★ Nature and Private from Lanais
Presented by Paradise in Hawaii Luxury HomesWelcome to Secret Tropical Hideaway at the Fairways in Mauna Lani!Secret Tropical Hideaway offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious,...
Marriott Waiohai Beach Club: luxury 2 bedroom on Poipu Beach oceanfront resort
Please choose a Friday through Sunday check-in and enjoy a seven-night stay.Thank you for choosing Dash Realty Group of Windermere, Florida. We are a registered Fla. Seller of Travel Ref. No. ST42435.Our rates reflect garden/island views. Ocean view/oceanfront villas...
Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach
RELAXING GARDEN RESORT:Kihei Resort offers a wonderful zen like experience. As you walk through the grounds of Kihei Resort, it is difficult not to enjoy the serenity of the beautifully landscaped grounds, smell the plumerias and hibiscus, as well as listen to the...
Newly Remodeled Maui Eldorado J102 - Kaanapali Beach - Great Views
Be one of the first to enjoy the place after a complete remodel. Photos taken January 2021Maui Eldorado resort property on Kaanapali golf course. Beautiful paradise views from lanais & floor to ceiling glass windows.A short walk (less than 5 minutes) to the beach with...
Maui Tranquility II - Relax & Feel Welcomed!
Maui Tranquility II - Relax and Feel Welcomed! This is the second chapter in our Maui Tranquility story. Another amazing place to stay on Maui, completely remodeled with meticulous attention to the details so you'll feel comfortable and appreciate the aesthetics,...