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.
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...
100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with...
Papakea Penthouse - 3 Br ocean view 1 min walk to the beach! - No cleaning fee!
NO Cleaning fees!!! NO resort fees!!This condo has AMAZING views of the ocean, pool, spa, and beautiful resort grounds. Close enough to walk to several restaurants, grocery store, and food trucks.Three bedroom penthouse unit. The master bedroom has a king bed, the guest...
Fully Remodeled Ocean Front Comfort HKOK316
Hawaii Tax ID: TA-101-435-1360-01TMK: 390080030055Oceanfront Bliss in North Kihei CondoWelcome to your private slice of paradise in North Kihei, where breathtaking ocean views await you from the moment you step into Unit 316. Experience the magic of Maui's coastline...
KAANAPALI - FULLY RENOVATED WITH OCEAN VIEW
Welcome to B208! This is a stunning ocean view home at beautiful Papakea Resort. Our condo is conveniently located on the second floor with very close access to the ocean and the pool area in building B. This is a legally permitted vacation rental and hotel zone...
OCEANFRONT BEACH HOUSE WITH SUNSET VIEWS AND PRIVATE POOL
Kona Bay Estates is a gated and patrolled oceanfront community. The Sunset Beach House offers 2700 square feet of luxurious space. It is just 500 meters from the sea. Opening walls of glass offer indoor-outdoor living with spectacular views of the ocean and a private...
Paradise Awaits in this Luxurious Villa in Ko Olina
Luxurious 3 bedroom Villa located in West Oahu. Enjoy all 4 of Ko Olina's ocean lagoons. Walking distance to Four Seasons, Disney Aulani, Marriott Beach Club, Ko Olina Center (shops and restaurants), Ko Olina Golf Club, Roy's Restaurant, and Monkey Pod Restaurant.State...
Fresh 1 Bedroom with Parking at Waikiki Banyan !!
Freshly Furnished One Bedroom Unit at the Waikiki Banyan with Peakaboo Diamond Head Views! One Free PARKING already included (max 6'), Bedroom with 1 Queen + 1 Full Bed; Living room with 1 Full BedCoin and App Operated washer and dryer on the same floor.Waikiki Banyan...
❤️PiH❤️ Pualani Villa ★Elegance★Heated Pool & Spa★Private Cottage
Introducing Pualani Villa, by Paradise in Hawaii Luxury Homes.At Paradise In Hawaii, we pride ourselves on providing some of the most sought after homes on the Kohala Coast and are thrilled to add the exquisite Pualani Villa, a single level four bedroom home, with pool...
Waikiki Studio for Rent (30 day min)
* Best Views and the Best Value in Waikiki! This unit is completely and beautifully redone with quality and function, 'Pride of ownership for our Guests to Enjoy'. * This unit has a 30 day minimum requirement. * This Spacious studio in the Island Colony has Awesome...
Hali'i Kai 12E: Beautiful Oceanview Villa w/Resort Pool, Spa, BBQ, AC & Lanai
Experience the epitome of island luxury at Haliʻi Kai 12E, a stunning 3-bedroom, 2-bathroom corner villa nestled within the prestigious Haliʻi Kai Resort on the sun-drenched Kohala Coast of Hawaiʻi's Big Island. This ground-level retreat offers sweeping views of the...
Papakea Resort E305 is Open! Please Visit West Maui & Help Our Businesses.
ALOHA,As an owner at Papakea Resort and living on the west side of Maui, we lived thru the devastation of the wildfires that took our precious Lahaina town, on August 8, 2023. Many locals lost their homes and businesses, and many need your help by returning to paradise....
Best View in Town, A205 come check out the View
Lokelani A205. Enjoy breathtaking, unobstructed views of neighboring islands Molokai and Lanai. The surf is just 30 feet away from two private balconies – the perfect vantage point for whale and sea turtle watching, as well as our legendary Hawaiian sunsets. Enjoy the...
Kona Palms#201:Oceanfront with great views, AC, elevator and wraparound lanai
Gorgeous views from this spacious and updated 1041 square foot condo with 2 bedrooms, 2 bathrooms and Sleeps 5 to 6! Picture yourself relaxing in this absolutely beautiful condo, enjoying the ocean views, while watching surfers and the magically blue waters of the...
2 Bedroom Kona Coffee Farm with Ocean Views in Holualoa
The rental is the entire downstairs with it's own private entrance and large patio with BBQ. The downstairs has two separate bedrooms with a large family room in the middle. The kitchen has a refrigerator, sink, microwave, two burner hotplate, toaster over, and coffee...
South Kihei Condo; Steps to Beach!!
Aloha!Enjoy this awesome 2nd floor unit, steps to the beach, shopping and dining, with a partial ocean view from the living room and lanai.The property has 1 pool, barbecue grills located directly outside the unit just downstairs, and beautiful landscaping throughout....
Maui Resort Rentals: The Whaler 724 - Corner 1BR/2BA w/ Wrap-Around Balcony, Gorgeous Partial Ocean and West Maui Mountain Views!
From its desirable 7th-floor corner floor plan, Whaler 724 delivers gorgeous views of the turquoise-hued Pacific, Maui's neighbor island Molokai, and the lush West Maui Mountains. During the winter months, this spacious 1BR/2BA suite enjoys an excellent vantage point...
Wyndham Kona Hawaiian Resort
Please note, that some holiday weeks require a seven-night stay, please confirm with an agent. Prime weeks and holiday weeks have higher rates, your agent will send you an initial quote based on the dates you have chosen.Thank you for choosing Dash Realty Group of...
Pili Mai 5D - Luxury 3bed/3bath, Sunny side
Make yourself at home in this luxury three bedroom, three bathroom condo located on Kauai’s sunny south side! A generously open-floor plan allows for abundant natural lighting and air flow throughout the entire home.The spacious living room features comfortable...
Tropical & Elegant- Sleeps 8- Ocean/Waterfall Views
Ala Hale is a luxurious island retreat with stunning views of the ocean & majestic mountain views. Located on the Makai Golf Course at the 6th hole, within the prestigious resort community of Princeville, Ala Hale's large private pool and spacious lanai's let you...
Newest 2 BR at Maui Eldorado, prime Ocean View
Enjoy your next family getaway in centrally located Kaanapali beach resort area with spacious 1440 square feet plus double length lanais. Ideal for a family up to 6 person, this accommodation offers premium ocean and golf course views and amenities such as shared pool,...
Best 2 Bedroom Condo in Kihei - Paradise Awaits All Year
ALOHA and welcome to our home at Luana Kai. Our unit is set apart from any other by the love we've put into it and the care we've taken to maintain it. Our deluxe condo has tile floors throughout and stainless steel appliances for your use. Although we don't have air...
OCEANFRONT-HOME FULLY EQUIPPED-FOR FUN AND SLEEPS 10!
Centrally located fully equipped oceanfront beach home. This is Hawaii at its best!Our home is fully stocked for fun with board games, body/surf/paddle boards, beach toys. We also provide free beach towels, chairs, umbrella, cooler. FREE airport shuttle, fast wifi, A/C...
Pam and Glyn's Maui Banyan Retreat in Sunny Kihei. Check Out Our Reviews
PLEASE NOTE: YOU ARE RENTING FROM A PRIVATE OWNER. ALL ACCESS INFORMATION WILL BE SENT TO YOU DIRECTLY FROM THE OWNERS. OUR ONLY ASSOCIATION WITH THE MAUI BANYAN RESERVATION DESK IS FOR THEM TO ISSUE PARKING PASSES AND POOL CODES, THEY DO NOT HAVE ACCESS TO OUR CONDO....
Newly Remodeled, Beautiful Oceanfront Studio!
DISCOUNTED for September, October, November & December 2025Beautiful, newly renovated (Jan 2022) studio just 30' from the ocean. The shower was just renovated Dec 2023.Aloha and welcome to The Maui House 207! When you enter our tropical Hawaiian home you will be...
Wai'nani Waterfall House HEATED Salt Water Pool /Hot Tub BEACH GEAR Games VIEWS!
Welcome to the Wai'nani Waterfall house located in sunny Poipu on the south shore of Kauai. This home has all you and your Ohana are needing for the perfect island getaway. Set in the heart of Kiahuna Plantation Golf course, this new home was designed with families in...
Kaanapali Alii | 171
Welcome to Kaanapali Alii 171, a beautifully renovated vacation rental that offers a spacious and inviting atmosphere for families and friends. This stunning residence features a large open floor plan, perfect for entertaining and enjoying indoor-outdoor living. The...
Tranquil Keauhou Resort Condo with Ocean View & Resort Amenities
Escape to paradise at Keauhou Resort Condo 139, a charming 1-bedroom retreat in Kailua-Kona, Hawaii. This beautifully updated condo offers a peaceful getaway with no neighbors above or below, ensuring privacy and tranquility. The inviting living room features high open...
Hale Laki – Stunning Resort Condo, Walk to Beach!
Summary:Waikoloa is a picturesque resort area on the Big Island’s western coast, blending natural beauty with modern amenities and making it a sought-after destination for visitors and locals alike.The Space:Perhaps its most defining feature is the stunning coastline,...
Absolutely Stunning Oceanfront Condo!
It’s private and quiet. This is your perfect Hawaiian getaway! Wake up with this stunning view of the Pacific and fall asleep serenaded by the melody of the ocean. While you bask in the sun, enjoy the company of many sea creatures (turtles, dolphins, and whales). All...
2021 Toyota Tacoma with a Rooftop Tent and all the camping gear!
2021 Toyota Tacoma TRD Sport with a Pop up tent! Our camper truck comes with all the amenities! Travel around the lush island of Maui and stay in a different part of the island every night!! Book your adventure today!! We provide everything you need from bedding &...
Excellent for couples or families. Right on the Golf Course.
Our villa provides 2 Bedrooms and 2.5 Baths, totaling over 1400 square feet plus 2 Lanais. It is perfect for families or couples vacationing together. The well-appointed kitchen has beautiful maple cabinetry and granite countertops. Eighteen-foot vaulted ceilings in the...
RELAXING, Away-from-it-All home on the water with small Natural Pool
Hale Pali (Cliff House) is a spectacular (non-smoking) OCEANFRONT home overlooking the blue Pacific. We heartily agree with our guests who have enthusiastically stated: 'there is nothing that compares to actually being on the water' - what better way to enjoy the sound...
Kaanapali Alii | 296
Discover the perfect Hawaiian escape at Kaanapali Alii 296, a stunning two-bedroom condo that offers a blend of luxury and comfort. Spanning 1,807 square feet, this residence features an open floor plan adorned with elegant tile floors throughout, creating a warm and...
Kukui'ula Villa 8: Oceanview Condo w/AC/Private Lanai, Walk to Shops/Restaurants
Welcome to Kukui’ ula Villa #8 by Elite Pacific, offering a unique charm of Kauai in this luxury Poipu vacation rental condo with expansive ocean views and chic island contemporary décor. Ideally situated within walking distance of the Shops at Kukuiula, Kukui'ula...
Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
***Facility Fees will be waived at the Papakea Resort, beginning July 1st!***Note: The owners own a second unit on the same floor, L-205, so the two can be booked together for larger groups and families. Welcome to Papakea! Located between the Kaanapali and Kapalua...
Stunning Ocean Front Studio! Mahana 803!
STUNNING VIEWS OCEAN FRONT STUDIO MAHANA 803! NORTH KAANAPALI BEACH, A/CWelcome to Mahana 803! Located on the eighth-floor, this oceanfront studio sleeps 2 and features stunning panoramic views of the ocean, beach and outer islands. Living area highlights include tile...
Pili Mai Family Condo 6G, 2 Bedroom, 2 Bath, Plus Loft with Queen Murphy Bed
Two Bedrooms, 1 King bed, 1 queen bed, 1 queen murphy bed, and 1 queen sofa sleeper, 2 bathrooms, nicely upgraded, washer and dryer in unit, lanai, golf course view, great complex amenities.If Sunny Poipu is your vacation choice, 6G at Pili Mai is a great option with 2...
Cozy 1-bedroom with AC and WiFi in enjoyable Kailua-Kona
Welcome to Hale Kai Hideaways, Bungalow A. Vacation at this cute apartment centrally located in the heart of Kona. Alii Garden's open-air marketplace is a five-minute walk, where you will find Shaka's tacos, local coffee & tons of souvenirs. Turtles Beach, a local...
Ocean Front! Includes Waikoloa Golf Membership Benefits. Halii Kai 13A
This vacation rental is professionally managed by ResorticaHawaiiHalii Kai 13A. Includes Waikoloa Gold Golf Membership DiscountsPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King Bed and 1 Twin Fold Out Chair...
Wai'ula'ula M101 - Ground-Level Oceanview Residence
This corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with Sub-Zero, Fisher & Paykel and Wolf appliances/gas range, dual master suites with California king beds....
Steps Away From Poipu Beach * A/C * Newly Remodeled * Family Friendly
Remodeled bright, beautiful, breezy top floor, corner unit in Building 23 on Kiahuna Plantation. Located 100 yards from Top 5 Rated Poipu Beach. Fabulous expansive views of gardens, twin bridges and lagoon. A new cal king bed in the master and a new queen sleeper sofa...
Maui Retreat Ekahi 50F, All YOU Need! 5% off for stays over a week!
The rest of JUNE $299 per night!Waiting for you to come and unwind. Just bring yourself, everything else is HERE! Towels, beach chairs, umbrella, boogie board, whatever you need!!!This beautiful second floor unit has an open, beautiful garden/mountain view. The vaulted...
Mauna Lani Point | F206
Welcome to the exquisite Mauna Lani Point F206, located in the prestigious Mauna Lani Resort on the stunning Big Island of Hawaii. This beautifully renovated two-bedroom, two-and-a-half-bath residence promises an extraordinary stay.As you enter, you'll find a tastefully...
Lei Aloha - A Private Retreat, Pool + Fairway Views
Welcome to Lei Aloha, Princeville!This luxurious island home is a 4 bedroom, 4 bathroom home combination of elegance filled with an abundance of amenities. This hidden retreat located in the prestigious resort community of Princeville is one of its kind , and provides...
❤️PiH❤️ Hono Loa ★ Bikes/Beach Toys ★ Private Beach Club ★
Presented by Paradise in Hawaii Luxury HomesWelcome to Hono Loa at the Fairways in Mauna Lani!Hono Loa offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious, and serene retreat for both...
Oceanfront Home with Pool ‘The Cove at Milolii'
Front row views of Kona sunsets Our two-story oceanfront home has views from every room and tropical breeze flowing from roof top cupola through every window and door. The main living area is upstairs with 4 bedrooms and 3 bathrooms, including two master suites one with...
Kona Penthouse 2 Bedroom: Relax and Unwind Aloha Style
Top-floor Kona retreat with stunning ocean views!This 2,000 sq. ft. unit features one king-size and one queen-size bed, hosting up to 4 guests. Perfectly located near downtown Kona's restaurants, shops, and farmers market, tucked in a family-friendly neighborhood. Fully...
Steps to the beach, come share our Maui dream.
Kihei Bay Surf is a cozy 2 story complex of 80 studio condos across the street from the beach. The complex is well kept and clean, with a great pool and jacuzzi area, complete with lounge chairs, 2 barbecues and tables, tennis court, laundry room, and plenty of parking....
Hale Koolau Estate - Private Retreat in Haena with Hot Tub & AC
Hale Koolau Estate (Main House + Treehouse), Haena Permitted Vacation Rental Property - Permit ID: TVNCU #1017 and TVNC #1018Transient vacation rental is located in the tsunami evacuation zoneOn the north shore of Kauai, Hale Koolau Estate sits behind wooden gates and...