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.
Experience Your Perfect Maui Getaway at Condo #3-408: Ocean Views & Amenities!
#3-408 has everything you will need for the best Maui stay! This updated condo feels like your home away from home with all cooking gadgets and service needs supplied along with crisp, clean linens and towels and even beach chairs to take across the street to Charlie...
Hawaiian Getaway at this lovely 2 bedroom - 2 bath condo!
Located in Waikoloa Village, enjoy what this 2-bedroom condo has to offer. Guests can unwind in the superb living room with a cozy sofa bed, take advantage of the fitness room, and stay connected with WiFi. The soothing atmosphere of this condo, complete with AC and a...
Cozy ground-floor condo with heated outdoor pool, private lanai, close to shops
Keauhou Akahi 103Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your tropical oasis in Kailua-Kona, HI! This stunning ground floor condo at the Keauhou Akahi property...
Maui Ka’anapali Villas #202: One-bedroom garden view condo at Beach Front Resort
Maui Ka’anapali Villas #202: One-bedroom garden view condo at Beach Front Resort on N. Kaanapali BeachThis condominium is located in the Aloha Tower, the central hub of the property. Situated on the second floor, this condo has views of the surrounding foliage. This...
Kailua Luxury Beachfront House
Prices start at $36,000/month and will not be pro-rated based on the length of stay. Please inquire for an accurate quote.Welcome to Kailua Beach Villa. This luxury beachfront home is perfect for your next Hawaiian vacation. This spacious 2 level home has 5 bedrooms (1...
Kona by the Sea Charming 1-Bedroom Condo with Ocean View
Escape to paradise in this inviting 1-bedroom, 2-bath condo featuring breathtaking ocean views. Perfectly situated at Kona by the Sea condominiums, allowing you to fully immerse yourself in the beauty of the Hawaiian lifestyle.Step inside to discover a cozy living area...
The Grand Islander, a Hilton Grand Vacations Club - 1 Bedroom Premier Luxury - Ocean View
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Discover Kamaole Sands 3-101 - Premium Ground Floor Renovation, Split AC, Wi-Fi
Step into the spirit of Maui at Kamaole Sands 3-101, a beautifully remodeled, ground-floor 1-bedroom, 2-bath retreat in sought-after Building 3. Surrounded by the resort's lush tropical gardens, this condo offers the perfect blend of privacy, tranquility, and...
Kaimana Beach Getaway | Park View King | Direct Beach Access
Set between the Pacific Ocean and Kapiolani Park, Kaimana Beach Hotel offers a peaceful escape on Oahu’s Gold Coast. This Park View King room features generous space and calming views of lush greenery. Ideal for nature lovers who enjoy tranquil mornings and quiet...
Relax, Unwind, Play Luxuriously
Enjoy your Maui vacation in a luxurious 2-bedroom resort view villa at the Westin Nanea Ocean Villas in Lahaina. Built in 2017, the units are managed and maintained by the Westin resort, and you will check-in at the hotel's front desk. Includes full resort access. Each...
Kihei Akahi D213 Ocean View
Aloha and Welcome to Your Maui Escape at Kihei Akahi D213!We're new owners and offering great prices. Discover your perfect island getaway at our beautifully updated one-bedroom, one-bathroom condo in the heart of South Kihei. Just steps from Kamaole Beach Park II and...
Maui Resort Rentals: Honua Kai Hokulani 301/2 – Incredible 6BR Oceanfront Gem, Over 4400 combined Sq. Ft. w/ Built-in Viking B.B.Q.!
Situated in the closest columns to the ocean at the entire Honua Kai Resort, this phenomenal 6BR offering combines two of the absolute finest 3BR/3BA oceanfront residences on offer to create a true masterpiece, perfectly suited to larger groups or families. Each...
Whaler Resort 1BR/2BA, Premium Ocean View - Newly Remodeled - Unit 457
Newly remodeled luxury unit, Ocean view. ONE bedroom TWO full bathrooms, completely remodeled May 2023.All top-of-line stainless steel appliances, furnished kitchen with everything new. Hawaiian top-of-the-line furniture, living room, bedroom, and new TV.Quartz...
Luxury Oceanfront Living in Kona!
Discover this newly remodeled (in 2024) Oceanfront 1-bedroom gem in Kailua-Kona. This sought after condo offers discrete luxury living right on the Pacific Ocean. Watch the sunset with uninterrupted views directly from your lanai, watch the whales breaching without even...
The Westin Nanea Ocean Villas Resort & Spa Hot Tub
Experience - a state of relaxation and repose - firsthand at The Westin Nanea Ocean Villas! Set on twenty-six acres of lush, tropical land and infused with a variety of Hawaiian design elements, The Westin Nanea Ocean Villas blends a top-notch vacation experience with...
nCondo in beautiful Waikiki Marina - Ocean / Sunset / Marina Views
This beautiful condo resort near Ala Moana CenterLocated close to Ala Wai Yacht Harbor and Fort DeRussy, Waikiki Marina Resort at the Ilikai provides a grocery/convenience store, a terrace, and shopping on site. The onsite American cuisine coffee shop, Aroma Caffe,...
Kiahuna Plantation Resort 82 Royal Garden 1 BD
- 2nd floor condo with lanai- Walk-up, no elevators- Kitchen includes granite countertops, full stove top and oven, microwave, full size refrigerator, dishwasher, coffee maker, blender, toaster, cookware and tableware- Bedroom with 1 king bed- Queen sofa bed in living...
Kona Magic Sands#313:Top Floor,Direct Beachfront, Rarely Available Lanai unit
Kona Magic Sands #313 – Top Floor Beachfront ParadisePerched on the top floor of the coveted Kona Magic Sands complex, Unit 313 is a rare gem—one of the few with its own private ocean-view lanai. Fully newly remodeled from top to bottom, this bright and stylish...
Mid-Century Modern Manoa Home with a Mountain View
Discover the magic of Manoa!Welcome to Hale Wailele, our beautiful 2025 renovated mid-century modern home in lush Manoa Valley. With breathtaking views, abundant natural light, and custom design details, it's a serene retreat just minutes from Manoa Falls. Enjoy two...
Regency Waikiki 72 City View 1 Bedroom
Experience Waikiki from this stylishly renovated one-bedroom condo, perfect for up to four guests. Featuring all-new furnishings, it offers a fresh and modern retreat just moments from the beach. • Newly renovated with all new furnishings• Newly renovated kitchen...
Find Paradise at Marriott Maui Ocean Club Towers-Three Bedroom Villa
OM Villlas is proud to present luxury villas at Marriott's Maui Ocean Club Lahaina.Reservations are available in weekly (7 night) increments with arrivals and departures on Saturdays only.Beginning Aug. 23, 2025, to Dec.16, 2025, Marriott’s Maui Ocean Club - Lahaina &...
Lodge at Kukui'ula Villa 10 w/Private Plunge Pool
Welcome to Lodge at Kukuiʻula Villa 10, your private island retreat on the sunny south shore of Kauaʻi. Blending laid back elegance with modern comfort, this four-bedroom villa offers a serene escape surrounded by the beauty of Hawaiʻi’s lush landscape, sparkling...
Kapalua Bay Villas – Spacious Double Retreat in Maui’s Premier Resort
This listing is a combination of 2 separate units close to one another.The ResidencesExperience the best of Maui with this unique two-villa combination in the prestigious Kapalua Resort. Perfect for families or couples traveling together, these villas offer the...
Disney Aulani Two Bedroom Oceanview Villa!
Boasting over 1100 sq ft of luxurious living area, this luxurious two bedroom ocanview villa is located at the magnificent Disney Aulani Resort and Spa amidst Oahu's upscale Koolina Resort Area and offers an impressive poolside location.Elegantly designed, the two...
Hale Malu - a peaceful refuge above Hilo, A peaceful retreat above Hilo
Welina mai to Hale Malu, a light-filled home of peaceful refuge, with three bedrooms and two baths, wood-burning fireplace (wood provided), spacious fully-stocked kitchen with modern amenities, free WiFi, and free off-street parking. Enjoy the views of Mauna Kea and the...
Royal Kahana Maui 1119 Ocean View Studio
- 11th floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Vinyl plank flooring in entry,...
Hillside Villa 2102 – Ocean View & Cozy | Onsite Staff & Daily Housekeeping
This ideally-located, 2-bedroom, 2-bath ocean view villa is the perfect size and features beautiful ocean, golf course, and sunset views and sleeps up to 4. Beach access and all of the resort’s amenities including golf, spa and sports club are less than 2 minutes away...
Near Golf & Beaches, 2 Pools, Quiet Location, Gated Community
Welcome to your Waikoloa retreat - a bright villa designed for relaxation & connection:- Sleeps 6 | 2 bedrooms | 3 beds | 2 baths- Shared pools & hot tub- Private lanai w/ golf course views- Fully stocked kitchen & hardwood dining- Beach essentials included- Free...
Cozy Hotel Room w/ Partial Ocean Views and AC - Bamboo Waikīkī Hotel #1206
Castle Bamboo Waikīkī Hotel #1206 - This studio boasts a rustic island décor with tropic earth tones, and handsome hardwood flooring throughout. The large sliding glass doors allow for natural sunlight and lead to a private outdoor lanai where you can relax in...
Dlx Oceanview Maui Studio...Steps to Ocean! Updated. AC.
Aloha: welcome to your own Deluxe Oceanview West Maui Studio condo rental,..Ideally located just minutes from famous Kaanapali resort, and steps to Beaches! Your Maui Condo rentals features an updated Hawaiian-tropical decor, in a beautiful setting... with separate...
Serene Sky Blue Lounge: Unwind in Comfort & Style
Welcome to this charming 3-bedroom, 2-bath home, the perfect blend of modern comfort and serene ambiance for your next getaway. Featuring a spacious, open-concept kitchen and a cozy, inviting layout, every corner is designed with relaxation and convenience in mind. This...
2024 Christmas Week! Westin Kaanapali Ocean Resort Villas , 2 Bedrooms, Sleep 8n
Available Dec.20, 2024 --Dec.27, 2024.We are the owners of this week at the Westin, so when you rent from us, we transfer the reservation to your name. Upon arrival, you will check-in at the resort’s front desk using confirmation # just as if you had booked directly...
Oceanfront Penthouse at Kona Reef King Bed fast WiFi AC Free parking
Oceanfront Kona Reef Penthouse – Stunning Kailua Bay Views & Prime Location! Watch Sunsets and surfers from the lanai. This air-conditioned 1BR/1BA top-floor condo is just steps from Honl’s Beach and a short walk to Kona’s lively downtown. Enjoy a spacious living...
Kahala Oasis: 6BR Retreat with Pool, Spa & Near Beach
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 Kahala Oasis by Gather, an...
Wailea Ekahi Village | 51D
Wailea Ekahi Village tropical vacation condos are situated above Maui's beautiful Keawakapu Beach and close to all the top Wailea resort hotels. Enjoy easy access from your vacation condo at Wailea Ekahi Village to the restaurants and spas of the Grand Wailea,...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beachfront Fun at KoOlina Club Resort+Amenities.STUDIO
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢! Reserve your Luxury Beachfront Escape at KoOlina Beach Resort's Nai'a Lagoon.𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 𝐰𝐢𝐭𝐡 𝐅𝐢𝐧𝐝𝐢𝐧𝐠...
Island Getaway: Room w/ Access to Beachfront
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
Lovely 2 Bedroom Condo in Makaha Valleyn
If you are looking for gorgeous less crowded beaches, unique hikes, and perfect surf this is your kind of place. 2 bedroom, one bath unit in Makaha Valley, West Side of Oahu. Just 1.5 miles from beautiful beaches, only sand, ocean, surf and majestic mountains! 12 miles...
Luxury 2BR/2BA at One Ala Moana
Enjoy the many luxurious perks of this upgraded 2BR/2BA unit at One Ala Moana. This fully furnished and well appointed unit features fabulous ocean and mountain views, high end finishes and top of the line appliances, walk-in closet, full size washer/dryer in unit....
Ocean Facing View - 3 Bedroom - Westin Nanea Ocean Villas - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing rates to direct resort bookings. Units are managed and maintained by the resort. Upon arrival, guests will check in at the resort’s front desk using their resort...
Fairway Villas Waikoloa Golf View 2 Bedroom + Loft
Golf View 2 Bedroom 2 Bath + Loft- Condo located on 3rd floor- Kitchen features granite countertops, ceramic cooktop and oven, refrigerator, microwave, dishwasher, coffeemaker, toaster, rice cooker, blender, cookware and tableware- Balcony with Golf course views- Master...
Wailea Beach Villas | PH404
Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho'olawe and...
Volcano Village Bungalow, 1 mile to Park
Poliahu is a newly built, modern bungalow designed for a refined and luxurious experience that is comparable to an upscale hotel stay. Featuring a king-sized bed, radiant heated floors, and contemporary lighting, this bungalow offers expansive forest views and a touch...
-NEW- Luxurious well appointed Hawai'i home with spectacular Mauna Kea Views
THIS PROPERTY CANNOT BE RENTED FOR LESS THAN 31 DAYSMonthly rent includes utilities (water, electric, wifi, landscaping) for rental periods of 1-3. Monthly rentals of 3 months or more are utilities included with a cap on electric. Rents under 6 months are subject to a...
NH 105 Breathtaking 2BD Direct Oceanfront West Maui Condo, Oceanfront Pool and Secluded Beach
Nohonani 105 NEW LISTING! Explore the Beauty of Hawaii on the Ocean at this Convenient Central West Maui Location! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset...
Marine Surf 13th Renovated with Small Parking Space
Newly renovated studio in Marine Surf Waikiki, perfect for 4 with a cozy sofa bed. Enjoy window AC + tower fan for comfort. Located in the heart of Waikiki, close to everything! Free small parking included. Please note: Oct 27–Dec 2025, the building will undergo...
Family House by the Waterfall - Private, Countryside, Waipio, Stream, WiFi, Laundry
You get the whole house! A super comfy family getaway, very private on the beautiful and peaceful Hamakua Coast - away from the tourist crowds of Kona and Hilo. We are a short walk to the Waipio valley overlook! Our house is great for adults and children. Come enjoy,...
Full duplex w/fast WiFi, expansive mountain views, 2 balconies, pool & grills
Paniolo #202 A & BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Picture-perfect views abound at this tropical retreat! This full duplex boasts stunning views of lush foliage and...
Perfect Hawai’i ocean view condo with AC, WiFi, Sleeps 4, in heart of Waikiki
Welcome to our beautifully renovated studio condo at The Palms Waikiki, located in the heart of vibrant Waikiki. This tastefully furnished space offers a perfect blend of comfort and style, ensuring a memorable stay for our guests. Enjoy ocean and Diamond Head views...
Aqua Aloha Surf Waikiki 205 Moderate Studio with Partial City Views, Sleeps 2
Aqua Aloha Surf Waikiki 205 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, Sleeps 2, 175 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and...