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.
Penthouse Unit built 2007, Across from Kahaluu Beach, Fantastic Ocean Views!
Love to snorkel and want to see over 100 species of tropical fish & turtles? Then why not stay right across the street from Hawaii's best snorkeling beach?! Our modern beachfront unit offers gorgeous ocean/sunset views and the easiest access to the incredible snorkeling...
New Owners! 3-Bedroom Home with Sunset Views! Beach Club/Pool/Fitness Center
Luxurious and family friendly vacation home in The Villages at Mauna Lani! Enjoy captivating sunsets with partial ocean views from the main floor lanai. Flow effortlessly to the indoor living area with spacious living, dining, and chef's kitchen. Each bedroom features...
crater rim cabin garden view
Four room cabin. Full kitchen, living room, bedroom and bathroom. We pride ourselves on cleanliness and comfort. Our full kitchen is generously stocked with breakfast foods, fresh fruit and much more. The kitchen includes a smooth top stove, full sized refrigerator,...
Golfer’s Lava Cove - Waikoloa, HI
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Condo, Huge Wraparound Lanai! HKH-515
** 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...
Oceanside Luxury on the beautiful island of Kauai
Oceanside Luxury is an Oceanfront and Lavish two-bedroom, 2nd floor unit in the extremely desirable "A" building at Waipouli Beach Resort. This 1,158 square feet condo unit offers astonishing direct oceanfront view with gratifying sunrises. Enjoy whale watching in the...
PK K207 Relaxing Maui 1BD Condo w Pool & Beach
Papakea K207 NEW LISTING Relax on Maui at this 1Bedroom, 1Bathroom, Just Steps from the Pool and Beach! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel...
Relaxing 4-Bedroom Farmhouse Retreat on Working Farm
Situated on a 20-acre farm, Hale Makana Kamalei is an expansive 4-bedroom house with an open floor plan. Explore the island as locals know it.Discover the back orchard and enjoy fruits from more than 50 fruit trees, vegetables from our organic garden, and fresh eggs...
Skippers—Fully air conditioned, Private Location, Near Gorgeous Beach--TVNC4190
ONLY A DREAM AWAY...OLD HAWAII'S GIFT OF ALOHA! With all the vacation rentals to choose from, why should you choose Skipper’s Beach Cabana? The answer is simple: if you want to experience your Kauai vacation in a town setting, choose Princeville. But if you want to be...
Kihei Akahi C310-Owner Managed-Complete Renovation-Modern Luxury-A/C throughout
Kihei Akahi C310 is a fantastic 1 bedroom, 1 bath condo. It has an ocean and Haleakala view from the lanai (balcony). It was completely renovated in 2022, with new furniture, new appliances - new everything! It has been modernized with Mitsubishi split A/C units in both...
Wailea Elua Village 1102 - 1 Bedroom Ocean View Condo
This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to the white-sand Ulua Beach that fronts this property. Be one of the first in the ocean in the morning to snorkel the...
Pacific Monarch Hotel Corner Unit
Visits to Hawaii have always been expensive, but each year prices seem to go higher. However, I think if you compare my condo with other options, you will realize it is a good deal. I try to keep the nightly rate about $100 less than what the hotel charges. I want...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
We do not Rent on Craigs list if you find this on any other site it is a scam be careful there are lots of scams ,NEVER wire money ..Please READ the whole Description below about the pool below,Mahalo Hale Manu Mele B&B permit #BBKM2013/0001.Tat # TA-031-786-3936-01 The...
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, Split AC!
Welcome to Wailea Ekahi 39E, a beautifully appointed one-bedroom, two-bath condo offering breathtaking ocean views and the perfect blend of comfort, style, and convenience. Whether you're planning a romantic retreat, a peaceful solo vacation, or a productive remote work...
Stunning OCEAN-VIEW Condo #C108 – Across the BEACH from Kamaole One Beach!
Escape to paradise in this gorgeous, newly remodeled condo at Kamaole Beach Club (#C108)! Located right across from the beach, this luxurious ground-floor unit offers breathtaking ocean views, upscale finishes, and an unbeatable location in the heart of South...
Hurry 7/24-8/20 available! Ocean & Beachfront Maui Sands of Kahana with A/C
Escape to Oceanfront Luxury at Sands of Kahana – Where Maui Dreams BeginWelcome to your beachfront Maui vacation — a spacious, fully air-conditioned 2-bedroom, 2-bath oceanfront condo located in the heart of West Maui’s Kahana community. Perched on the 8th floor,...
May in Maui at lower price! 11TH FLOOR Luxury Condo on Ka'anapali Beach!
E Komo Mai! You will begin your Mahana tropical experience when you open the front door! From our ocean front condo on the 11th of 12 floors, you will see windows that go from the floor to the ceiling, & wall to wall in the living room. The Pacific Ocean is right there!...
North Shore Beachfront Bliss! Perfect family-sized home on a sandy beach
Come and enjoy the best the North Shore has to offer in this right-sized sandy beachfront home, perfect for families and small groups. This property is located on a gorgeous bay in Haleiwa so you not only have a beautiful long sandy beach to enjoy, but you are a stones...
KLVR welcomes you to Honua Kai Luana 11A Oceanfront Resort Resort and POOL view
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful garden level Luana Villa at the Honua Kai Resort. This luxurious villa is located within a private garden enclave at the spectacular, beach front, Honua Kai resort. This villa boasts 2047 sq. ft. of...
Aloha Condos, Na Hale O Keauhou, Townhome C-4, Ocean View, AC
Best ocean view townhome in rhe resort: Sunset Views Year Round180 Degree Ocean ViewsWalk to Kahalu'u Beach Park- the best snorkling beach in KonaAdjacent to Restaurants, Cinema, Grocery Store• Beautiful Ocean-View Gated Complex• Large & Luxurious 2 & 3-Bedroom...
Large beautiful home with air conditioning! Walk to Beaches, Resort Pool
Aloha and E Komo Mai - Welcome to the Sunny Poipu Hale!The moment you walk through the tropical private atrium you'll feel right at home. This newly remodeled 4 bedroom/3-bath, 2-story house is nestled in a relaxing, family friendly resort neighborhood in walking...
Leilani Villa: Gardenview Condo on Kauai's North Shore w/ Pool, Spa & AC
Set within the coveted Nihilani at Princeville community on Kauai’s lush north shore, Leilani Villa offers an inviting blend of island comfort and resort convenience. With 1,874 square feet of airy living space, three private lanais, and thoughtful touches for both...
🏝️SUMMER Special - Your Maui Getaway-Walk to the Beach, Pool, Hot Tub🏝️
Our beautiful home away from home is 'Your Perfect Maui Getaway,' a charming one-bedroom, one-bathroom condo nestled in North Kihei. Located in Kihei Resort, a small boutique condo complex with free parking and no resort fee. It is just a short stroll to Kalepolepo...
KKSR#1202 DIRECT OCEANFRONT, 2ND FLOOR, REMODELED!, AMAZING VIEWS
Knutson & Associates is proud to be offering an incredible direct oceanfront unit in Building 1 at Keauhou Kona Surf & Racquet Club! A spectacular second story condominium that is oceanfront living at its finest. Enjoy Relaxation time on your incredible large lanai just...
Maui Resort Rentals: Honua Kai Hokulani 415 - Upgraded 2BR Ocean View Suite w/ Deluxe Corner Floor Plan!
Widely regarded as the premier two-bedroom floor plan at Honua Kai, this oversized two-bedroom boasts a 1325 sq. ft. interior with direct ocean views from the kitchen, dining room, and living area, as well as the 315 sq. ft. wraparound lanai (balcony). The Hokulani...
On the Beach! Kihei Sands Beachfront Resort, Unit A1
Kihei Sands is a Direct Beachfront complex, Popular Unit A1 - An Amazing Location!Aloha & E Komo Mai to our beautiful Condo, Unit A1~We purchased and completely renovated A1, we love spending time here as a family! Since we are new to the condo rental experience, we do...
Tiki Hut Cottage - Lush Tropical Garden, ;Walk to Tunnels Beach TVNCU#5161
Capture the magic of this romantic cottage. Large picture windows, open beam ceilings and sky lights bring views of lush tropical gardens with towering Cook pines. Two covered lanais for pupus, mai-tais and outside dining. After an adventurous day on the Kalalau Trail,...
Kuleana Club #513-Oceanview -1 bd & 1 ba-3rd Floor
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a 3rd floor ocean view condo, only steps to the ocean, surrounded by a plush Hawaiian garden. Enjoy...
Lanikai Hale - Elegant Kauai Villa + Guest House | Stunning Ocean Views | Private Pool + Hot Tub
Summary:Discover Lanikai Hale, a luxurious, family-friendly retreat on the south short of Kauai. This peaceful villa includes access to a detached ohana (guest house) and comfortably accommodates up to 10 guests. Enjoy a private pool, hot tub, fire pit, outdoor kitchen...
Whale Watching Season is Now! Poipu Luxe with Oceanview! Walk to Beaches, Hiking
Experience the best of Kauai’s natural beauty at this serene ocean-view getaway, just 15 minutes from the golden sands of Poipu Beach. Ideal for whale-watching enthusiasts, this spacious retreat lets you witness these majestic creatures right from the lanai during...
Kaanapali Shores #933, Stunning Top Floor Full Ocean View Condo
Welcome to your ultimate getaway in paradise at the Aston Kaanapali Shores Unit 933. Be on top of it all in this top-floor penthouse suite offering stunning 180 degree ocean and pool views. From your personal lanai you will enjoy the sparkling blue of the ocean,...
Oceanfront Luxury Condo Closest to Beach
OCEANFRONT LUXURY CONDO CLOSEST TO BEACH 2br/2ba sleeps (4-6) White Sands Village, Kailua-Kona, Kona Coast, Big Island, Hawaii, USA (20 minutes south of airport overlooking White Sands Beach on Alii Drive 3 1/2 miles south of Historic Kona)This luxury oceanfront condo...
🏖️Fully Air-Conditioned | Ocean View | Beautifully Renovated | vrKCV
vrKCV - Kona Isle B38, Professionally Managed by Kona Coast Vacations.Welcome to your oceanfront retreat in scenic Kailua-Kona! This renovated one-bedroom condo offers stunning ocean views and is located right at the water's edge, providing you with the perfect base for...
Hawaiian home with incredible ocean views, orchids, and gorgeous sunsets
Our home is in a rural area of the Big Island, on one acre of landscaped property with orchids, palms, banana plants, a koi pond and more. This is our personal residence, available the months when we are not there. The kitchen is totally equipped with everything but a...
Bright, modern decor with ocean views
Maui Kai 504 1 Bedroom, Oceanfront Condo with AC. Panoramic Ocean Views Private & QuietReservation protected. This property resides in a district unaffected by any currently proposed Maui transient Vacation rental restrictions. Enjoy panoramic ocean views from this...
Granma's Cabin Kona coast
Official website. When Granma was 95, we had to move her in with us to take care of her. This left her little panabode cabin (900 square feet with a 500 square-foot wrap-around lanai) vacant. Lucky you . . . you can spend your Hawaiian vacation in this beautiful, quiet,...
Maui Resort Rentals: Honua Kai Hokulani 930 - Extra Large 1BR w/ 9th Floor Mountain Vistas!
Hokulani 930 is a luxurious 1BR/1BA mountain view suite that enjoys expansive vistas of the lush West Maui Mountains from its impressive 9th-floor vantage point. This oversized suite is ideally suited for small families and couples who will relish the spacious 765 sq ft...
G204 | Tropical Paradise | Beachy Kihei Surf Bungalow
Welcome to your perfect Maui getaway at this beautifully updated 2-bedroom, 2-bathroom condo in Kihei Garden Estates. The contemporary "surf shack" design creates an authentic Hawaiian atmosphere, featuring a spacious loft primary bedroom with a plush king bed and...
*Newly Renovated Oceanfront Waikiki- Ilikai Marina
*Exciting Updates in Progress!We’re currently renovating to make your stay even better. In the meantime, please take a look at our beautifully updated Ilikai Marina listing to see the stunning upgrades you can expect soon!We’re excited to share our top picks for...
Makapu’u Hale, Literally oceanfront! VIEWS! A/C, 2 bedroom/2 bath
We are literally oceanfront! E Komo Mai (Welcome) to Paradise!30 Day minimum stay required by Oahu OrdinanceOur homes are fully furnished with everything you need for an ideal Hawaiian vacation!Makapu'u Hale is 2 bedrooms, 2 baths, newly decorated with comfortable &...
Beach Front, Pool, Amazing Sunrise! Welcome to Oceanside Retreat At Kapaa, Kauai
ALOHA! This 1st floor, updated unit has a private lanai to enjoy spectacular ocean views, stunning sunrises or perhaps an evening moonrise, if the time is right! This place has it all! The pool is just 20-feet from the lanai, and world-famous Waipouli Beach is only...
Spacious OCEAN FRONT 2Bd/2Ba Condo with AC - Sands Of Kahana 315
Oceanfront Sands of Kahana Resort- beautiful, remodeled 2 bedroom, 2 bathroom condoOceanfront Pool and second poolRestaurant and BBQ areasFitness CenterTennisACWalking distance to restaurants, stores and shoppingThis exquisite 1880 square foot condo is beautifully...
New Listing! Northshore Gem - 2 bd/2ba Plantations @ Princeville!
New! North Shore Gem: Organic Bedding, Luxe Island Amenities, AC, Pool, Hot Tub, Gym, Smart Home LUNALANIA unique boutique stay experience for those who tend to gravitate toward spaces that offer a bit more than the ordinary, this 2-bedroom, 2-bathroom Garden Island gem...
Marriott's Ko Olina Beach Club - Luxury 2 Bedroom Villa
Marriott’s Ko Olina Beach Club is situated on the beautiful Western shore of Oahu, where waterfalls and fountains welcome you as you drive under the port- cochere. Just 30 minutes from Honolulu, this beach front oasis is secluded and peaceful. Surrounded by seven...
Hilton Pool Pass included - Lux Penthouse w/ Views
Experience the ultimate Hawaii getaway in our beautiful condo, meticulously designed to provide unparalleled comfort and luxury. Step into the welcoming open-concept living area that blends modern amenities with gorgeous furnishings, bathed in natural light that...
Marriott's Ko' Olina Beach Club (mountainview). Inquire first before booking.
Cross posted on Airbnb_platform as well. Cheaper there as it does not charge Hawaii state taxes. This is a Marriott Vacation Club property. Multiple rooms can be booked for same dates. If your dates aren’t available in same room layout and view for entire stay it may...
Private Tropical Paradise in the Heart of the North Shore - beachfront community
[Oahu requires a minimum 30 day rental stay. All quotes will be returned for 30 days to ensure a valid stay duration]Aloha, we want to extend our home to your family to build great Hawaiian holiday memories on the beautiful island of Oahu.Located in the heart of North...
Newly renovated beachfront paradise steps away from the tranquil shores of Anini Beach!
Just steps from the sand on Anini Beach, this spacious 3 bedroom home was JUST remodeled! With luxury furnishings and a gorgeous kitchen that will make even chef's mouths drop, this home is a true oasis on Anini Beach. Located near the end of Anini road, this home's...
Molokai HideAway Hut: Snooze by seals + Wake to songbirds ~200 yds to the Ocean!
If you're looking for a secluded spot surrounded by lush, tropical foliage and only steps to untouched beaches, Molokai HideAway Hut is the place to be!LOCATION: Inside of the top resort on Molokai's West-End, called: Paniolo Hale, which means "Cowboy House" in...
Oceanfront 2 BD Villa with Endless Ocean Views
We welcome you to stay in our nicely upgraded condo just a short walk from the beautiful beaches located in Kapalua. Relax and enjoy your Maui vacation at Kapalua Bay Villa 35G4. A gorgeous 2 bedroom, 3 bath villa offering 1,450 square feet that can accommodate 4...