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.
Idylliic beachfront private guest suite on the beautiful North Shore of Oahu
Beachfront property just walk onto the beach any time, located on a quiet cul-de-sac. The minimum length of stay is 14 days and I will block a 30 day period as the law regarding this property state that it may not be rented for fewer than 30 consecutive days; however...
Newly Remodeled Modern Condo + Free Parking Waikiki
Welcome to our spacious, modern one bedroom condo located on the 6th floor above the swimming pool/jacuzzi. Renovations on the condo were completed in January 2021. Along with 24 hr. security, amenities include free secured parking (hotels charge up to $50 a day), with...
3-bedroom lovely unit just across the street from beautiful beach.
Discover this fabulous 3-bedroom gem in Ewa Beach, Hawaii. This updated delightful apartment is fully furnished and in a convenient location for island fun. The cozy living room is the perfect for relaxing after a day of exploring. An open floor plan with plenty of...
Lae Nani 534 Fantastic view is what we have, none better on the island of Kauai
COMPLETELY REMODELED AND NEWLY INSTALLED SPLIT SYSTEM AC!! Come and enjoy this beautiful condo with unparalleled view of the Wailua Bay and Pacific. One our most requested condos. Very tastefully decorated and updated (just remodeled spring 2014), this condo offers...
This is the spa for your soul
Queen size bed, one bathroom with exquisite glass block enclosed walking shower with beautiful tile work depicting a swimming dolphin with tile floors and granite countertop.Living room features a queen sleeper sofa with a 52" flat screen TV. Cable is provided as well...
Remodeled 1BD/2BA in Best South Kihei Location, split A/C, 3 min from the beach!
Aloha and welcome to Tranquil Turtle Retreat at Maui Banyan! Our recently remodeled owner-managed condo is located right in the heart of South Kihei close to world-class beaches, shopping and amazing restaurants. We have thought through all the details to make your...
Townhome in Waikoloa Resort - Close to Pool & BBQ Area!
Enjoy resort living at Colony Villas 201, a spacious two-story townhome located at the renowned Waikoloa Beach Resort. This 2-bedroom home is perfect for families or friends, and is close to all the best beaches, restaurants and shopping on the Kohala Coast. The home...
Special ~ Kapalua Golf Villa 24T8 - 1BD Luxury
Indulge in the tranquil beauty of Maui at Kapalua Golf Villa 24T8, a beautifully appointed 1-bedroom, 2-bathroom villa that perfectly blends luxury, comfort, and panoramic ocean views. Step into 1,100 square feet of elegantly curated living space, where contemporary...
Puu Poa 211 Air Conditioned and Best View Too
Aloha Unit 211 is on the far right side of the complex and faces almost due west, thus having the best Bali Hai view. You can enjoy Bali Hai sunsets while dining, reclining in the living room, seated in the atrium, lying in the master bed, or of course, while relaxing...
Hoku Hale – Ainamalu at Waikoloa Beach Resort
***Luxury Golf Course Estate with Private Pool, Daily Hilton Waikoloa Pool Access, Concierge Services & Game Room | Sleeps 10+ in Waikoloa Beach Resort***Welcome to Hoku Hale at Ainamalu, your ultimate luxury retreat nestled in the heart of Waikoloa Beach Resort....
Home with mountain views, lanai, & near the ocean
Star of Waikoloa - Ainamalu House with Guest House - Special Rates for FallOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You'll be wowed by this newer-built home in the new...
Maui Resort Rentals: Kaanapali Alii 314 – Expansive 2BR+DEN Ground-Floor Residence, Luxuriously Remodeled, Steps to the Beach!
Luxuriously remodeled, this 2 bedroom den ground-floor gem delivers partial ocean views, an expansive 1850 sq ft of interior living area, and a sleeping capacity of up to 8 guests. The oversized outdoor living space and lawn area effectively doubles your lanai...
Views! Views!!!
Looking for that romantic getaway? Our little slice of paradise is ideal for Honeymoons, anniversaries, babymoons, or that special romantic escape. Looking for amazing sunsets and whale watching from you own private lanai? Check us out!!Experience oceanfront tranquility...
Wavecrest Resort Vacation Condo
Come share our little oceanfront slice of paradise on Molokai. When you visit the Wavecrest Resort, the A-building is where you want to be. Right on the water, the experience is totally different. You have a front-row seat for all the beauty of the ocean and all the...
Hali'i Kai 20G "WishWeWereHere" Newly renovated! Oceanfront resort, gears bikes.
PROPERTY DESCRIPTION: Ours is the most spacious floor plan at Hali’i Kai with 1677 square feet, 1930 square feet if include the two lanais. This is a two-story Townhome with the entrance on the second floor, no elevator.You will enjoy our newly remodeled condo with...
Place in Paradise - Kailua Beach Oceanfront Vacation Home
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1802 It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
Luxury Mauna Kea Rental Home
The Hawaiian word for family is ohana and we affectionately call our home, O2 or Ohana 2, as it is our family vacation home and we would love to share it with the you!Marvel at the shimmering Pacific Ocean and tropical Kohala Coast views from our inside living space as...
Pristine End Unit, Mauna Lani Golf Villas, Beach Club+Golf Pkg savings!
STVR-21-559570Seeking a flawless, worry-free spot for your next get away? Look no further….Come, relax and make yourself at home in our well-appointed, high-end furnished, corner villa inside the Mauna Lani Beach Resort. Take advantage of our Kings Club membership at...
Hale Okale By Parrish Kauai - Hanalei Value & Location
Located in the quaint and historic beach community of Hanalei Bay, this comfortable Kauai vacation home offers its guests a spacious and relaxing place to settle in and enjoy beach life. Hale O’Kale is walking distance to all of Hanalei town with its shops and...
Maui Resort Rentals: The Whaler 1020 - Luxurious 10th Floor 1BR w/ Gorgeous Ocean and West Maui Mountain Views!
Enjoy beautiful views of the Pacific Ocean and Maui's neighbor island Molokai, as well as views of the West Maui Mountains from this luxurious 10th-floor one-bedroom suite at the iconic Whaler in the heart of Kaanapali Beach.Tastefully remodeled, this suite is the...
Aloha Condos, Na Hale O Keauhou, Townhome E-2, Ocean View, AC
Located in the highly desirable Na Hale Community, this beautiful well-appointed 2-bedroom, 2.5-bathroomtownhome offers spectacular ocean views and breathtaking sunsets. Bothbedrooms feature private, ensuite bathrooms. Additional in-home conveniences includea washer and...
Mauna Kea Villa 3022 - Ultra-Luxe Hawaiian Villa for Rent
This single-level, sophisticated, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living, a chef’s kitchen with Wolf and Sub-Zero appliances, a dining area for 10 with adjoining wet bar as well as bar seating in...
🏖️Walk to Beach, Restaurants, Shopping | Concierge Included | vrKCV
vrKCV - Kolea 15L, Professionally Managed by Kona Coast VacationsWelcome to Kolea 15LA luxurious haven within the renowned Kolea community, located in the heart of Waikoloa Beach Resort on the stunning South Kohala coast. This exclusive residential gem offers direct...
Captivating Ocean Front Condo Living-Poipu Shores
Every evening, the sky transforms into a masterpiece of warm colors, reflecting off the endless ocean, creating an unforgettable view from this coastal retreat. This beautifully designed vacation rental offers breathtaking views of the Pacific, where you can watch sea...
Moana Makai & Moana Mauka – Kailua-Kona Oceanfront Estate
We are 2 luxury oceanfront vacation rentals on the Kona Coast. Voted "Best Private Estate in - Kailua Kona Hawaii" October 1, 2016 These two beautiful homes share the estate’s lava rock saltwater pool and jacuzzi, lushly landscaped yard overlooking the Pacific ocean,...
Privacy + Luxury • Oceanfront • Panoramic View
Summary:Hali’i Kai in Waikoloa Beach Resort • 69-1033 Nawahine Place #13D • 5★ RatedHali’i Kai 13D is a Kohala Coast oceanfront corner villa located in the highly desirable gated property situated in Waikoloa Beach Resort. This upgraded villa boasts 2...
❤️PiH❤️ Shades of Summer ★ Fully detached home ★ Hilton Pool & Waterslide Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Shades of Summer, part of our Hawaiian Luxury Collection. Shades of Summer is a beautiful 3 bedroom / 3 bathroom freestanding home that offers everything that you would ever desire on your Big Island vacation...
Historic Upcountry Ranch Home
PERMITS: SUP2 2019/0015 and STMP T2019/0002MAUI’S VRBOS ARE NOW OPEN TO TRAVELERS FROM THE MAINLAND AND ELSEWHERE. FOR LATEST INFORMATION PLEASE GO TO travel.hawaii.gov. WE PROVIDE: 1. ENHANCED CLEANING PROCEDURES BETWEEN GUESTS 2. HAND SANITIZER AND DISINFECTING...
Sweet Lava Retreat with Epic Ocean and Volcano Views
** Please note that the House is not a fit for children under 6 years old or the elderly, as there are lots of stairs and balconies, a steep ladder within the Main House, and there is uneven lava in the yard.Welcome to the Hakuma House, a cozy off-grid retreat with...
Steps from Waikiki Beach | Pool + Jacuzzi
Immerse yourself in island vibes at this cozy studio, just 1.5 blocks from Waikiki Beach. Perfect for up to 3 guests, the space features a queen bed, a sofa bed, a kitchenette, and a private balcony. Relax at the tiki-inspired pool and jacuzzi or explore vibrant nearby...
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,...
Ohia Lehua Hale-Hot Tub-Fireplace-Fire Table-3-Bed, 2-Bath Newly Renovated Home
Welcome to Ohia Lehua Hale, located just 6 minutes from Hawaii Volcanoes National Park. Escape to our recently renovated vacation home; we recently added many upgrades to enjoy a relaxing stay.*New Built-in Gas Fireplace *New Smart TV*New Outdoor Hot Tub *New Outdoor...
❤️PiH❤️ AQUA MARINE DREAM ★Big Golf Discounts★Free Hilton Passes★Tennis/Pickleball
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Aqua Marine Dream, a part of our Hawaiian Luxury Collection. It's is a wonderful 4 bedroom home and 4.5 Bath (Mahina Model) equipped for up to 10 people.The home has had recently been updated with lovely new...
Poipu Sands 214 - Ground-Floor Condo with Pool & Hot Tub Access, Steps from Stunning Beaches
POIPU SANDS 214 AT KOLOA KAI VACATION RENTALSA Tranquil Island Retreat on Poipu Kai GreenbeltWelcome to Poipu Sands 214, a beautifully appointed ground-floor condo just steps away from the lush Poipu Kai Greenbelt and the breathtaking Shipwreck Beach. Whether you're...
Coastal Remodeled ocean view Papakea Resort condo
Recently updated Papakea Resort 1 bed, 1 bath fully stocked condo is in a great location with beautiful Ocean Views. This bright and airy condo has coastal vibes throughout and can accommodate 4 people. It comes with all the household items and beach gear you'll need...
Whales and great reviews! Royal Kahana 2 Bd/2Ba ! Hotel zoned Safe to Book!
We welcome and need you to visit our beautiful island. We thank you for your support and welcome you! This property is hotel zoned which means that short term rentals will continue to be legal rentals at this property. The apartment zoned properties are proposed to be...
Luxury Villa l Designer Furnishings, Central A/C
Summary:E111 | TA-167-599-1040-01Experience refined island living at Villa E111, a luxurious Poolside Villa in the heart of Poipu. Outfitted with designer furnishings, a gourmet kitchen, central A/C, and in-unit laundry, this spacious retreat offers all the comforts of...
Luxury Villa Steps from Wailea Beach with Resort Amenities & Stunning Upgrades
This property is hotel zoned, and not being affected by the recent proposed legislation.Wailea Beach, voted one of the top beaches in the world, is a short walk from Ho'olei Villas. This amazing beach offers numerous activities such as paddle boarding, snorkeling, sea...
Kamaole Sands 10-307, Ocean View, Large Lanai, Twin Murphy Beds, Split-AC, Wi-Fi
Experience relaxed island living in Kamaole Sands 10-307, a beautifully renovated third-floor one-bedroom, two-bath corner condo in Building 10. Fully remodeled in 2016, this bright and airy unit offers stylish enhancements such as stainless-steel appliances, granite...
Recent remodel - Large 1BR w/ ocean view and walk to excellent beaches/eateries
Recently Remodeled (2021)!Large 1BR unit at highly desirable Shores of Maui. The Shores is a place that people return to year after year, so once you've stayed there you'll likely do the same and return for years to come. A small 50 unit condominium complex with a mix...
Oceanfront Luxury at Honua Kai Konea 250: Stunning Views & Gourmet Amenities!
This property is hotel zoned, and not being affected by the recent proposed legislation.Honua Kai Konea 250 offers luxury at its finest! As you enter you will be in-awe of the breathtaking direct ocean views from this luxurious villa located at one of the most exclusive...
❤️PiH❤️ DAYDREAM VILLA ★ Bikes and Beach Gear ★ New Home ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to one of the newest homes in our Hawaiian Luxury Collection. Daydream Villa at KaMilo is a wonderful newer 4 bedroom home.We pride ourselves on providing some of the most sought after homes on the Kohala Coast...
ALA 12 Perfect Getaway Remodeled Private 4Bedroom Beach House Near Beach
Alaeloa 12 Beautifully Remodeled 4Bedroom Beach Home with Stunning Ocean Views and OceanFront Pool in Napili Bay. Idyllic Peaceful and Relaxing Winter Retreat FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your...
Penthouse Luxury Oceanfront, Third Floor, 2 Bedroom | 2 Bathroom with Central Air
Lanikai 131 – Oceanfront Penthouse with Panoramic Views & Central A/CWelcome to Lanikai 131, a premier top-floor penthouse offering front-row views of Wailua Bay and Papaloa Cove. With 2 bedrooms, 2 bathrooms, and central air conditioning throughout, this elegant...
Spacious Ranch Cottage with private hot tub and VIEW!
Our Ranch House Cottage sits above the town of Kona with beautiful views of the Kona Coast. We are a 10-acre gated estate. This unit has a private Hot Tub/Jacuzzi with magnificent views. We a working farm with miniature goats, sheep and chickens. Fresh fruit and fresh...
NEWEST! California Coastal Inspired in Maui 2 BR
Located in the heart of Kaanapali, this spacious, newly remodeled, 1,440 square foot, ground floor, 2-bedroom condo is ideal for one or two couples, or a family of 6 looking for a relaxing getaway! This condo is ideally located in the heart of the Maui Eldorado, steps...
North Shore Beach House with AC, 30 day rental
LOCATION:**Message for special dates and availability not shown in the calendar**If you’re you looking for perfect white sand beaches with clear turquoise water & close proximity to everything in the North Shore, this is the place for you. Directly across the road is...
Hale 'Imi Ola: Ocean Views, Luxury, Balinese Charm
Hawaiian ease meets Balinese charm in this uniquely elegant, custom-designed South Shore villa, with luxuries galore & views for miles. Brand-new & wonderfully spacious, Hale 'Imi Ola offers the ultimate in stylish, relaxing indoor-outdoor living, complete with pool/spa...
Princeville Delight! COLD A/C, Sleeps 4, Pool & Jacuzzi, Private Lanai & Space
Aloha!This studio sleeps 4 with a Kingsize bed and a Queen pull out sofa. Located in Princeville on Kauai's North Shore across the street from the Makai golf course. The Princeville center is just a short few blocks away and you can walk there on the beautiful walking...
Coconut Plantation 1086-1: Upscale 3BR Condo in the Serene Ko Olina Resort
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.Welcome to Coconut Plantation 1086-1 by...