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.
Maui Resort Rentals: Honua Kai - 5 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought after two-bedroom "penthouse" suites with three neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
LS 215 Direct Beachfront Views Remodeled Studio
Lahaina Shores 215 NEW LISTING Amazing West Maui Sunsets Every Night from your Private Lanai! Steps to the Beach and Pool FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Oceanfront Kona By the Sea 2-Bedroom Retreat with Central A/C
45-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside...
Pineapple Paradise - Natural rock tidal pool
**30-day rental. Please inquire.Welcome to Pineapple Paradise! This 2 bedroom, 2 bath oceanfront home has breathtaking ocean views along with a natural rock tidal pool, a unique feature for enjoying the water as the tide comes in. This is a perfect getaway paradise for...
🌺 Support LOCAL: NEW! Mākaha Valley Home With Large Studio And Amazing Backyard
🌺 Mahalo (thank you) for choosing to support LOCAL! 🤙🏻We are brand NEW! We know you have many options available to you in this neighborhood from big corporations and companies but we promise that you will be pleased with your decision. 😊SUPER family friendly...
New Listing Specials! Walk to Beach. Sleeps 6. Fantastic Resort Amenities.
Centrally located in Kihei and a three minute walk to Kamaole Beach, where you'll have access to some of the area's best snorkeling, whale watching, and sunsets. Short drive to coveted Wailea beach!★ Ocean View★ Private bedroom and bathroom★ Two full bathrooms★...
Relaxing Kalakauan 1-Bedroom | Private Lanai
This family-friendly vacation home is tucked away at the beginning of the Waikiki strip and features secured entry. This 1-bedroom, 1-bathroom offers easy access to the Waikiki Strip, Hilton Hawaiian Village, Fort DeRussy Beach Park, world-famous Waikiki Beach, Hawaii...
1 Bedroom Oceanfront W/Lanai-Kahana Reef #216
Kahana Reef #216: Grab your phone for selfies on your private lanai that has a backdrop of spectacular ocean views! Enjoy captivating sunsets nightly and during the winter, watch whales play in the distance. Lounge at palm-tree-top levels on the lanai. Here you can...
Stunning Beachfront Condo, Sans Souci, Kitchen, WiFi, Smart TV & Free Parking
Unwind in Honolulu at this cool condo. This excellent property is on the beach & features a cozy living space with a Queen murphy bed plus sofa bed, perfect for relaxing after a day of exploring. The well lit bathroom includes a bathtub / Shower combo, hair dryer &...
4 Units Perfect for Groups! Outdoor Pool, Close to the Beach!
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...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Tropical Garden Tranquility HNL
From kid-friendly splash pads and playgrounds to calming koi ponds, a private pool, meandering paths and shaded bbq and dining areas, this outdoor oasis offers endless outdoor spaces. This serene home-away-from-home offers two private bedrooms, full bath, full kitchen,...
Island Escape: 2BR Villa at Wyndham Kona Hawaiian Resort
Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort offers the perfect combination of relaxation, adventure, and Hawaiian...
Escape to Paradise! Townhome in Coconut Plantation, just minutes from lagoons!
Welcome to the wonderful resort area of Ko Olina! Located within the gated community of Coconut Plantation, this gorgeous townhome offers guests the perfect blend of comfort and convenience, the ideal island getaway. Features of the townhome include: Prime Location:...
HGVC Hokulani Waikiki Luxury, 1 BR Suites, Rooftop Pool/Spa, Close to Ft Derussy
Anchoring the northernmost stretch of the celebrated Waikiki Beach Walk® entertainment district, Hokulani Waikiki, a Hilton Grand Vacations Club offers ideal access to Waikiki’s most vibrant showcase for dining, shopping and entertainment. Just a brief walk from the...
Maui Resort Rentals: Honua Kai Hokulani 1029 - 2BR Deluxe Oceanview Grand Penthouse, BBQ on Balcony + Jaw-Dropping Ocean Views!
We are proud to present this jaw-dropping 10th-floor deluxe oceanview grand penthouse at the Honua Kai Resort—newly launched on 3/4/25 to start taking bookings beginning May 7, 2025!Unquestionably one of the finest residences on offer at Honua Kai, this stunning...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Discover the epitome of island elegance at Ko...
1 BR Suite City View, w/ AC, WiFi and Kitchen - Bamboo Waikīkī Hotel #504
Castle Bamboo Waikīkī Hotel #504 - The living area is furnished with a and a desk/workspace for all those business travelers. Enjoy watching the Flat screen TV while sitting on the new couch, which doubles as a fold-out sofa bed to accommodate additional travelers....
Ground Floor Private Corner Unit Waipouli Condo
Waipouli Beach Resort – Ground-Floor Island RetreatAbout the PropertyWelcome to your Kaua‘i escape at Waipouli Beach Resort F101 — where comfort, convenience, and coastal beauty come together. This one-bedroom, two-bath condo offers ground-floor access with a...
"BEAUTIFUL LUXURY CONDO WITH GORGEOUS VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA"
"MODERN LUXURY CONDO WITH BEAUTIFUL VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA""WELCOME TO SKY ALA MOANA" Luxury condominium built in 2023 conveniently located in Ala Moana. Enjoy beautiful views of city, mountain and sparking ocean. 1br/1ba /1assigned parking with Full...
Kihei 2 Bedroom Condo Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Located in South Maui, nestled within five acres of lush tropical landscaping. This low-density complex features amenities such as a large swimming pool, hot tub, tennis and pickleball...
NEW! Spacious 3BR Home in Old Wailuku Town | Central to All of Maui
*Reduced Introductory Rates and discount for stays 7 nights or more. Excludes Dec 20-Jan 5*Modern Comfort in Old Wailuku Town – 3BR Ground Floor of DuplexStay where Maui locals live, in the historic Wailuku Town—an authentic small town with coffee shops, galleries,...
Marriott Maui Ocean Club | Three 3BR/3BA Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ocean-MT Views From the Luxury Sky Ala Moana Condo with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to the luxurious building scene in Honolulu. Consisting of two...
Paradise Resort Home in Ko Olina | TCP-1220-3
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Manele Bay, Lanai Hawaii Ocean Facing Home
Spacious home on the island of Lanai. Footsteps from Four Seasons at Manele Bay Hotel and Hulopoe Beach. All the comforts of home in an island paradise. Two bedrooms, each with king-sized beds, and two and one half baths, including an outdoor shower. Ocean view and...
Steps Away from the Beach! 3 Premium Units, Private Lanai, Onsite 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...
Cozy Waikiki Apt with FREE parking sleeps 4
Cozy studio apartment loaded with amenities to make you feel at home while on vacation. The space can best be described as a hotel room with a small kitchen. This apartment is located in the heart of Waikiki. -parking is included (if paid separately would be at between...
2 Bedroom Mountain Garden at Marriott's Maui Ocean Club - Lahaina & Napili Tower
Spread out with the whole family in this spacious two-bedroom suite. This is as classic as a Maui oceanfront resorts get. Tropical greenery, koi ponds, palm trees, and Pina Coladas around every corner. Really, this place is situated perfectly on Ka’anapali Beach,...
Oceanfront balcony, 40 ft to ocean, 2 bed, 2 bath, remodeled! 3/8-3/15/2025!
This is Hono Koa, a timeshare resort located in Honokowai, 1 mile to Ka'anapali Beach resorts, and 3 miles to Kapalua. It's an easy 1-mile walk to the Times Market grocery store. We own only the KOA oceanfront units. They are bigger and nicer than the other units. The...
Kahala Lani: Balinese-Inspired Home with Private Pool
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Ideal for multi-generational families and golf...
Kaanapali Alii | 341
Kaanapali Alii 341 is a luxurious oceanfront vacation rental located about a 35 minute drive from Kahului airport along Maui's beautiful western shoreline. This spacious condo offers breathtaking views of the Pacific Ocean, the islands of Lanai and Molokai, and the...
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Ocean-View Lanai (800 Sq Ft) | 4 Mi to Ho'okipa Beach Park | Newly Renovated Kitchen Experience the serenity and adventure of island living when you stay at this stylish Haiku vacation rental! Located just 4 miles from the coast, this 3-bedroom, 2-bath home makes it...
Located In The Historical District And Near The Beach! Pet-friendly, Bar, Pool
Come for the beaches, stay for the adventure! With comfortable amenities and convenience to local attractions, you’ll have everything you need for a relaxing getaway or exciting family vacation. Take a dip in the rooftop pool with views of Waikiki. Enjoy a meal at the...
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...
*NEW 3BD Luxe Beach Estate |Pool, PickleB, Gym| AC
Welcome to our stunning 5 bedroom, 4 bathroom estate, perfectly designed for large groups or families. Centrally located in the serene Poipu Beach Estates, this property is just a half mile from the beach, offering a blend of luxury, comfort, and convenience. Our...
The Marbled Suite - Waikiki - Ala Moana - McCullynn
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...
Tremendous 5-bedroom homein Kailua-Kona
Modern Kona retreat just 3.5 miles from the airport! 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, enjoy cool breezes year-round....
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...
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
Garden View 2 Bedroom 2 Bath- Full kitchen includes refrigerator, stove/oven, microwave, dishwasher, cookware, tableware- Master bedroom with 1 king bed- Guest bedroom with 2 double beds- Sofa bed in living area- 1700 square feet / 158 square meters- Bathroom with...
Dreamy Beachfront Home - Car & Parking Available
*** Aloha! Welcome to our happy place! ***** Newly Remodeled Coastal Retreat, with Floor-to-Ceiling Ocean View **Welcome to our beach house, where every detail has been thoughtfully designed by a professional interior designer to create a serene, luxurious...
Panoramic Oceanfront Retreat in Lahaina Shores 509
*Seasonal Special: Stay 5 nights from now until December 15, 2025, and get 1 FREE!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...
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 $10.95/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
Welcome to Hale Kamaole! Nestled in South Maui, you’re just steps away from the beautiful Kamaole Beach Park III & a short drive to the Shops at Wailea. Enjoy breathtaking sunsets from your private lanai or the beach.The property features two pools, tennis courts &...
Oceanfront Center, Westin Ka'anapali, 2 bedroom, 2 bathrooms, 3/8-3/15/2025!
This 2-bedroom unit in Lahaina is perfect for your escape to paradise. This is a timeshare but is also a hotel that is managed by Marriott. Check prices with the hotel to see what a bargain this price is for our oceanfront center units. Oceanfront studios run $900+ per...
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...