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.
Waikiki Shore 205 Park View 1 Bedroom
Enjoy tranquil park views from this spacious one-bedroom retreat, set in the only condo on iconic Waikiki Beach. With lots of space and all the comforts of home, it’s a perfect place to unwind after a day in the sun.Unit 205 Park View 1 Bedroom 1 Bathroom• Waikiki Shore...
Charming 1-bedroom condo at Luana Kai in Kihei with WiFi B204
B204 is a charming one-bedroom, one-bathroom unit, situated on the 2nd floor (NO elevators so you are walking up stairs) is a wonderful tropical oasis for your dream vacation. Step into a spacious living area that comfortably accommodates up to four guests, making it...
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Welcome to our luxury 3BR/3BA estate in Poipu Beach Estates, just ½ mile from the beach. Perfect for families or groups, the property offers a beautiful common area with 2 large outdoor Lanais. Enjoy AC in each of the bedrooms, premium kitchen with quartz, and modern...
Island Charm Retreat at Inn on The Park | Walk to the Beach
*Important to note: if you're looking to book for longer than 30 days and the dates aren't showing as avaialble, please still reach out as the unit is likely available and we can assist in getting you booked for longer. Mahalo!*Incredibly located and uniquely designed,...
The Marbled Suite - Waikiki - Ala Moana - McCully
With all the convenience of Waikiki, but with free parking for your rental car. Located between Waikiki, Ala Moana, and the highway (without highway noise). For those looking to also explore outside of the tourist bubble called Waikiki, this location is golden. Minutes...
5-star Four Seasons style renovated gem with A/C and Ocean View
Located in Kailua-Kona, this superb 1st floor condo located in an oceanfront community offers a cozy retreat for guests. With 1 bedroom featuring a comfortable king bed and a well-equipped kitchen with Kitchen Aid appliances,granite counter tops and travertine floors...
Ocean View w/AC - Wailea Elua 306
Book with us and come to Maui to explore everything we have to offer!Wailea Elua is a premier resort located on Ulua Beach in the heart of Wailea. Maui's sunny south shore has some of the best beaches on the island. Ulua Beach is a top snorkeling and dive location in...
Kailua Kona Hawaii 3 Bedroom Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Nestled within one of Kona’s most exclusive gated communities, this 3-bedroom, 3.5-bathroom single-level luxury home offers the perfect blend of resort-style comfort and relaxed island...
Renovated 5BR w/ AC, Vaulted Ceilings & Lanai Ocean View Near Airport
Modern Kona retreat just 3.5 miles from the airport! New AC are installed on Jan. 2026. This spacious home features vaulted ceilings, a lanai with partial ocean view, and two fully equipped kitchen — perfect for families or group getaways. Located at 1,070 ft elevation,...
** 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...
Kapalua Bay Villa 18B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- Split level villa with no stairs between parking and front door- Tile floors throughout- Updated kitchen with granite counters includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware, tableware and unique chef’s...
C202 is a real favorite with great views of everything. 1 bedroom, 1 bathroom, remodeled partial ocean view with AC. C202 has a king size bed. Located on the 2nd floor, it has a an ocean view, views of the West Maui Mountains, pool and garden in the inner courtyard....
3rd Fl Ilikai | King | AC | Pool
The Space:Enjoy the perfect blend of harbor and ocean views from this beautiful suite, complete with a large lanai ideal for relaxing or watching the sunset. A sliding partition separates the bedroom from the living space for added privacy.Bedroom: King bed with sliding...
Tranquil Marina Front Pool House Resort
Marina Front Property in peaceful Cal-De-Sac with large tranquil salt water pool and marina access.Spacious outdoor patio lounge with BBQ grill and prep station and patio furniture and large TV.Parking for two cars! Close to Hanauma Bay, Kona Brewery, Costco, Koko Head,...
Kaanapali Maui Eldorado Garden View 2 Bedroom
Surrounded by tropical greenery, this two-bedroom garden-view condo is ideal for relaxing after a day at the beach. Located on Kaanapali golf course, it includes a full kitchen, comfortable living space, and plenty of room to unwind with loved ones. Garden View 2...
Marriott’s Kaua’i Beach Club Resort
1 bedroom, 2 bathroom Oceanfront Villa with lanai. Master bedroom, separate living room/kitchenette with Murphy bed, refrigerator, microwave, dishwasher and all kitchen utensils. Overlooking Kalapaki Bay.
Peaceful Oceanfront Haven | Lahaina Shores 509
Lahaina Shores 509 – Pacific Ocean ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 509 is a 5th-floor oceanfront studio offering privacy and comfort for 2 guests. Step onto the private...
Aston Kaanapali Shores - Studio Resort View - No cleaning or Resort fees
All of our guests have complimentary access to our Maui specialist and support team during their stay.*This condo is in the Aston rental program and is subject to a $11.95/day parking fee to be paid to the front desk on property. {A valid credit card is required to...
Hapuna Beach Residence B13 at Mauna Kea Resort
This impeccable, oceanfront, newly-constructed, ground level island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a true chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances, wine...
New Listing, Vistas Waikoloa B203 2/2. Ocean Views
Tropical Retreat at Vistas Waikoloa B203- AC, WIFI and ocean viewsAloha and welcome to your serene escape on the Big Island! Nestled in the heart of Waikoloa Beach Resort, Vistas Waikoloa B203 is a spacious 2-bedroom, 2-bath condo offering comfort, privacy, and ocean...
One Bedroom Condo Across Kamaole Beach Park III
Our one-bedroom condo is conveniently located just a few minutes away from the world-class shops at Wailea which offer fine dining, shopping, a shopping market and nearby Kihei boat ramp for easy access to snorkel, diving, and fishing boat adventures! Enjoy the gorgeous...
Ocean View, Central AC, Pool, Spa, & Hot Tub
Welcome to Ka'anapali Shores, the perfect spot for your island escape! Relax while gazing out at the sparkling Pacific, with endless options for Maui activities, dining and adventures just a short walk or drive away!Highlights:-Two large sparkling pools with cabanas and...
4 Suites with Balcony and Living Area | Outdoor Pool & Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Charming apartment with AC and WiFi in serene Kailua.
New charming studio rental located on the owner's property in beautiful Kailua, Hawaii. Perfectly situated just moments away from stunning beaches, lush landscapes, and quaint town. This cozy retreat offers a unique blend of comfort, convenience, and island charm. The...
Hale Mahie Nene By Parrish Kauai - Great family home with AC & Pool
Hale Mahie Nene is a refined retreat designed for those seeking tranquility, indulgence, and island elegance. Tucked away at the end of a quiet cul-de-sac and surrounded by the lush fairways of Kiahuna Plantation Golf Course, this private sanctuary offers peaceful...
** 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...
A Marbled Suite near Waikiki, Ala Moana, McCully
Fully A/Ced apartment, marble floors, granite counter tops, queen size bed in each room, TV in living room, and a in-unit washer/dryer.Located in between Waikiki, Ala Moana, and UH Manoa, this is the ideal starting and ending point for every day.Less than 15 minutes...
** 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...
Honua Kai | 3 FREE CARS | KBM Resorts | Extra Large Corner Suite! | 3 Units, 7 Bedrooms | HK ML-3577
** 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...
** 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...
2 Spacious Units with Private Lanais, Outdoor Swimming Pool!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Modern 3-bedroom Condo - Ocean View!
Amazing ocean views!3rd floor (no elevator). WiFi. 2 workstations w/computer monitors. Cable TV and free streaming apps. AC in kitchen/living room and main bedroom. Fans in all living spaces. Assigned parking . 1 mile from Makaha Beach. Close to other spectacular...
Royal Kuhio 1708 - Spacious Corner Unit w/ Ocean City Views in Heart of Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1708, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Queen-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiView: Partial ocean and mountain viewsKitchen: Fully equipped with oven,...
Honua Kai | 3 FREE Rental Cars | KBM Resorts | Ocean Front | 3 Units, 6 Bedrooms | HK ML-2561
** 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...
7 Nights in a 1-bedroom OCEANFRONT villa April 10-27, 2026
Stroll the white sand Ka’anapali Beach, sharing the sunsets with the isles of Lana’i and Moloka’i in view. Dine in the finest restaurants or grill your own fresh fish and steaks near the pool. Take a short walk along the boardwalk to Dukes, ride to the top of massive...
Lovely 5-bedroom house in Sunset beach vland for your dream vacation
Your Haleiwa adventure begins at this delightful 5-bedroom house. With 4 queen beds and 1 full bed, this charming property is perfect for a group getaway. Enjoy the iron and hair dryer amenities provided for your convenience. We're happy to assist with any questions...
2BR Villa at The Bay Club by Hilton- Full Kitchen, Lanai & Kohala Coast Paradise
Step into island comfort and spacious living with this two-bedroom villa at The Bay Club, a Hilton Grand Vacations Club, located along the stunning Kohala Coast within the Waikoloa Beach Resort. Ideal for families or groups of up to six, the villa offers two separate...
Everything You Need For The Perfect Vacation! Outdoor Pool, Oceanfront!
Step into paradise: Explore Kanaha Beach Park & indulge at Queen Kaahumanu Center, right from our welcoming Kahului Bay doorstep.This listing is for a room within a hotel.✦ Your room is 588 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV,...
Kaanapali Alii 3422 Bedrooms | 2 Bathrooms | Sleeps 5 | Partial Ocean View________________________________________Kaanapali Alii 342 is a luxurious one-bedroom partial ocean-view condo with a fully enclosed den that comfortably serves as a second bedroom.This...
Partial oceanview, AC, 1bedroom, across from beach
Welcome to Kihei Akahi C418. This 4th floor condo has partial ocean view from your private lanai. Enjoy a fully equipped condo ready to host your Maui memories. The condo can accommodate 4 people & has in unit washer/dryer. Kihei Akahi is located in the heart of S....
Tucked away on 3 acres of native rainforest the Honu Studio at Volcano Village Retreat is the perfect spot to rest and relax after a day of exploring Volcanoes National Park located just 2 miles away!We can`t wait to make the cottages the most perfect vacation spot for...
** 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...
Kolea 15C is a two bedroom penthouse with a nice open ocean view!
Enjoy unparalleled living in this spacious two-master bedroom penthouse condo, featuring stunning ocean views and panoramic mountain vistas, along with an extended floor plan that provides ample space and privacy for two couples or families.Once inside, you will be...
Peaceful Hideaway with Pool, Bikes & Perks
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
Kapalua Bay Villas | Oceanfront | KBM Resorts | 2 Units, 3 Bedrooms | ML-3491
** 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...
** 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...
Tropical Elegance: Tropical Elegance, Acacia Bar, Jetted Tub & Majestic Views
Welcome to Tropical Elegance by Gather, a beautifully remodeled 1,738-square-foot townhome in Princeville, Kauaʻi. Nestled in the serene Ka’iulani enclave, this refined retreat blends organic mid-century design with contemporary Hawaiian luxury. Surrounded by lush...
Villa In Paradise 2-bedroom with AC in peaceful Princeville
Westin Princeville Ocean Resort - Luxurious 2-Bedroom Villa - Family Friendly Resort!The Westin Princeville Ocean Resort Villas, perched on Kauai’s stunning north shore, offers a serene island escape. Overlooking the Pacific, this resort features spacious villa-style...
2 Westin Nanea Villas Beachfront Resort/Spa, Pool!
Experience "Nanea" - the Hawaiian state of profound relaxation - at The Westin Nanea Ocean Villas Maui. Set on twenty-six oceanfront acres of tropical paradise and thoughtfully infused with Hawaiian cultural elements, this luxury Kaanapali Beach resort delivers premium...
Hilton Hawaiian Village Breathtaking two bedroom! Incredible Beach and Lagoon!
Concierge Realty is proud to present luxury villas at Hilton Hawaii Village!We are able to offer reservations in weekly increments with arrivals and departures on Saturdays only.This amazing resort has it all. Set on 22 acres of lushly landscaped beach front property,...