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.
One of the Most Beautiful Ocean Views in West Maui at Kaleialoha
Gorgeously and recently renovated unit at Kaliealoha tucked in the corner to avail of the amazing ocean views West Maui has to offer. It’s arguably the best unit at Kaleialoha. Entire left wall has tinted widows for privacy, feels like your outside with nature. The unit...
Hualalai Hale: Four Seasons Modern Luxe Retreat on 1.5 Acres
Hualalai Hale: Your Luxe Private 4-Bedroom/4.5-Bath, Hualalai Resort Retreat, Tropical Landscape, expansive yard, Big Island HawaiiWelcome to Hualalai Hale—Your personal luxury resort home nestled within the exclusive and gated Four Seasons Resort Hualalai on Hawaii’s...
One Bedroom Ocean view Deluxe Luana Kai D105
D105 with AC is a gorgeous, 1 bedroom, 1 bathroom, ground floor, ocean view condo with a king size bed. It is located on the ground floor with a direct ocean view over the grassy park area and pickleball courts. The pickleball and tennis courts are located in front...
4Bed Beachfront home near Pipeline
Make yourself at home in this 4-bedroom 3.5-bathroom North Shore piece of paradise. This wonderful house boasts 1 king bed, 3 queen beds, and 1 twin bed, perfect for a tranquil getaway. With beachfront views from 3 out of the 4 bedrooms and all bedrooms with their own...
Modern Renovation with Ocean Views | Wailea Elua 905
Wailea Elua 905 is a vacation rental situated in the picturesque beach locale of Maui. This spacious three-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury, making it an ideal retreat for families or friends traveling together. This condo is...
Stunning Home w/Ocean-Mountain Views in East Oahu Serene Family Vacation
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out, professional...
Luxury 3 Bed, 3 Bath Beach Tower B-503 Great Ocean And Pool Views
Ko Olina Beach Villas.This property is one of the newest and most exclusive available for rent on the island of Oahu. But more importantly, this is our island home for much of the year. We love it here, and we know you will too.#503 in the Beach Tower has excellent...
Maui Resort Rentals: Westin Kaanapali Ocean Resort North Oceanfront Studio Villa
Luxury Oceanfront Studio Villa at The Westin Ka'anapali Ocean Resort Villas North. This luxury studio villa features outstanding oceanfront views of the Pacific Ocean and sleeps up to four with one king-size bed and one queen-size convertible sofa sleeper. The villa is...
2 - bedroom Waikoloa Townhouse 106, close to beaches and restaurants
New rental listing starting September 2023Welcome to our relaxing, freshly updated Villa at the Waikoloa Colony Villas. Unit 106.New furniture, and beds throughout the home! Waikoloa Colony Villas is a private gated community of luxury townhomes on the South Kohala...
🏖️Kolea Luxury | Walk to Beach, Restaurants, Shopping | Concierge Included | vrKCV
vrKCV - Kolea 16H, Professionally Managed by Kona Coast VacationsEscape to Kolea Villas – Your Hawaiian RetreatFeel your stress melt away as you step into this Hawaiian paradise, located on the edge of the Pacific Ocean. Nestled within the prestigious Kolea Villas in...
January Special 25% Discount - Hualalai 5-Bedroom House Close to Resort
"Ka Hale Ulu Le'a" means "House of Happiness" in Hawaiian, and this is the feeling you experience when entering this Hualalai property.This 5-bedroom, 5 Bathroom Family Oasis sleeps 10 for the ultimate family getaway, in a prime, close-in location at the exclusive Four...
Hanalei Bay View Retreat - An Artistic home overlooking Hanalei Bay
Welcome to Hanalei Bay View Retreat, overlooking Hanalei. Nestled at the edge ofPrinceville/Hanalei and centrally located to stores and restaurants as well as all the NorthShore’s best adventures. Adjacent to a forested greenbelt just beyond your windows, you’ll...
Hale La- Luxury Beach House with Central Air Conditioning!
Hale La in Kekaha, Kauai~ TVNC-4251 TA-000-602-1120-01Imagine spending your next vacation at one of the most beautiful properties on Kauai! Your days are filled with exploring miles of white sand beaches steps from your luxury vacation home, hiking the adjacent Waimea...
Villa de Aloha at Kolea Villa Big island Hawaii!
Luxury Kolea Villa at Big Island Waikoloa ResortWelcome to Big Island's most luxurious condo Kolea Villas Resort in front of A bay ( aka Waikoloa Beach )! We just fell in love with Kolea Villas here so beautiful and luxurious ! Plea come and say Hi to anyone here with...
2 BDRM w/ 4 Beds + 2 Bath + Parking + Partial Ocean View, 2 mins walk to Beach
Legal vacation rental at a fabulous location! This renovated 876 sq ft, 2 bedroom 2 bath with 2 balconies home is across from ‘Alohilani Resort, Steps away from the Waikiki Strip (Kalakaua Ave) and Waikiki beach! There are endless shopping, dining, and activities within...
MARCH CANCELLATION SPECIAL 349/NT 7nt min. Private, Romantic Cottage
Maui Permit #BBPH 2009/0002 , Hawaii Permit #SUP2 2002/0005Hawaii Tax I.D. TA035-442-8928-01 TMK (2)2-7-035-010-0000Maui's Ultimate Private, Romantic Cottage! ...a unique architectural Polynesian Pole home on Magical Maui. Secluded, romantic, beautiful island inspired...
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,...
UPGRADED-Oceanfront-3 BR-Sands of Kahana-Central AC.
Hotel Zoned!! Safe and Protected Stay! Book with Confidence. We offer Cancel for Any Reason Travel Insurance! Sands of Kahana unit 275 on the 7th floor in the ocean front building 2. Location, location, location! Located between Kaanapali and Kapalua you will the quaint...
Waikiki Tropical Getaway with Pool and Free Parking!
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Welcome to your cozy home away from home at the family-friendly Waikiki Banyan (Tower 2)! This 600 sq ft...
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 condo sleeps 2 people only.This is a legally permitted...
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...
This luxurious 3BR/3BA residence is conveniently set within Enclave One of the Luana Garden Villas. Villa 2C's north-facing orientation offers a shady respite from West Maui's legendary endless sun, and its designation within our "Elevated" collection at Luana Garden...
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...
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
Nestled on the sun-drenched Kohala Coast of Hawai‘i’s Big Island, Hali‘i Kai 12E offers a luxurious corner-villa retreat where sweeping views of the Pacific Ocean, lush fairways, and Mauna Kea’s volcanic peaks set the stage for an unforgettable island escape. This...
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....
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, Beach Cabana, Jacuzzi, 3 Pool
Maui Eldorado – Spacious Top-Floor Family Retreat with Ocean & Golf Course ViewsWelcome to this expansive two-bedroom, two-bath residence located in the heart of the Kaanapali Beach Resort area. Offering approximately 1,440 square feet of interior living space plus...
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...
Charming 1-bedroom condo in downtown Kailua-Kona just 2 blocks from the beach
Welcome to your perfect island getaway in Kailua-Kona! This beautifully updated condo is just 2 blocks from the beach and 1 block from the vibrant restaurants and shops along Ali'i Drive, putting you right in the heart of it all. Inside, you'll find brand new...
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...
Ocean Views | Close to Wailea Golf & Beaches
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
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....
Ocean Front Property adjacent to thousands of acres of undeveloped state land.
Kailea means "sea of dreams". It is a brand newly constructed property located in sunny Kaloli Point. It is a spacious ocean front lot with added sense of considerable privacy as it is adjacent to thousands of acres of undeveloped coastal state land, which you can...
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...
Wainani Waterfall House Poipu - Saltwater Pool & Spa, Golf, Beach Gear, Games
Relax… You’ve arrived in Poipu paradise!Welcome to our newly built home on Kauai’s sunny South Shore, designed for comfort and easy living. This is a place to slow down, spread out, and truly unwind.Inside, enjoy high ceilings and large glass doors that fill the home...
Kaanapali Alii 1712 Bedrooms | 2 Bathrooms | Sleeps 6 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 171, a beautifully renovated one-bedroom partial ocean view vacation rental with a fully enclosed den that comfortably serves as a...
Charming Keauhou Resort 139: Cozy 666 sq ft studio in Kailua-Kona, near ocean & adventure.
Welcome to your perfect vacation retreat at Keauhou Resort! This charming 1-bedroom condo offers a peaceful escape with no neighbors above or below, ensuring a serene and private stay. Ideal for a relaxing getaway, this unit combines modern amenities with resort-style...
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...