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.
Once you’re here - you wont want to leave! Exquisitely appointed. Views galore
Walls of glass sliders disapear creating indoor/outdoor living. Huge covered patio plus sunbathing deck around the 15' x 30' private pool just remodeled. Located in prestigious Bayview Estates gated community of fine homes 5 minutes to beach, shops, and restaurants....
Be at the center of action while enjoying a beautifully upgraded studio with top quality finishes
Be in the center of all the action while enjoying a beautifully remodeled studio with top quality appliances, and large bathroom with double-headed natural stone shower. The view of the ocean is impressive with two lanais. You also get FREE parking & high speed Wi-Fi....
Gorgeous Renovated Oceanfront Condo - AC & Free WIFI/Parking/Cable
Located on Kona's main strip, Alii drive, this unit gives you a million dollar view in a luxurious, well-appointed setting. Take in the magic of the island, all from your oceanfront lanai. Watch sea turtles sun bathe in the tidal pool below or look out for whales and...
Polo Beach 808! Unique opportunity one-bedroom, top floor home.
Unique opportunity to stay in a one-bedroom, top floor home at one of the most desired properties on Maui. Polo Beach #808 will be your favorite place to stay when visiting the island. Top floor, corner unit with EXQUISITE VIEWS of the Pacific Ocean, Molokini,...
Ali'i Point #12: Oceanfront Getaway w/ Hot Tub, AC, Lanai & Shared Pool
Set along the lava rock shoreline of Kailua-Kona’s Aliʻi Drive, Aliʻi Point #12 is a private oceanfront sanctuary within an exclusive gated enclave of just 16 homes. With 3,199 square feet of interior space and a sprawling 1,500-square-foot lanai overlooking tide...
🌴Luxurious Oceanfront Home on Golf Course – Paradise Awaits🌴
Set right on the golf course and ocean, this coastal style residence provides an idyllic setting for your ultimate Hawaii vacation. The 3 bed, 2.5 bath, 1,887 sq. ft. home rests along Kona Country Club's ocean course, where waves collide with the rugged coast and...
Sweet Rustic Cottage ~ Ocean View ~ Short walk to beach
A Classic Kauai Cottage on Acres of Beautiful Grounds. Away from developments and the public. More Island Artsy Than Corporate. Two ceiling fan's in living room and one ceiling fan in bedroom. One floor fan. Nice, natural breeze normally.Watch the sunrise off the ocean...
Wailea Grand Champions 84 - 3 Bedroom Golf Course & Partial Ocean View Condo
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. This spacious three-bedroom, two-bathroom condo offers views out over the Wailea Blue Golf Course as well as a partial ocean view. It\'s size and...
Stunning Ocean View at Kapalua Bay Villas
Kapalua translates to "arms embracing the sea" in Hawaiian. Enjoy one of the most special places on Maui at this 1-bedroom 1-bath Kapalua Bay Villa. Enjoy expansive views & the fresh island breeze from this second level unit with large bay windows & two patios. At the...
KONA CLOUD FOREST GUEST HOUSE~3 Bedrooms~
This two-story 3 bedroom home is nestled among the native forestry on the slopes of Hualalai with both mountain and ocean views. Just seven miles and a 15 minute drive to the heart of Kona town and and 14 minute drive from Kona International Airport. Nearby is Pa’ina...
Large 2 Floor Condo - Wifi/Central Air & Pool Across From Beach - Lots of Extras
The perfect place to enjoy your vacation in paradise! Centrally located and just 20 minutes from the airport, we are 1 of 54 condos in 5 buildings on 5.6 acres of beautifully manicured lawns and lush tropical gardens. This is a bright and airy, non-smoking, second...
Oceanview 1 bedroom Kihei gem, perfect location, walk to everything
Welcome to Island Surf 402. This ocean view centrally located 1 bedroom Kihei condo can accommodate 4 people & has everything needed to feel at home. Cross the street to get to Cove Park & Kalama Park, a favorite for surfing and walking around. This condo is steps away...
POIPU KAPILI 46 - FABULOUS OCEAN VIEWS - WHOLE UNIT AC - WALK TO BEACH/ SHOPPING
Poipu Kapili is a luxury, boutique oceanfront resort located in one of the most desirable locations on Kaua'i: Poipu. Walking in the door to Poipu Kapili 46, you will be drawn to the lanai overlooking the lush green grass, deep blue pool, and the spectacular Pacific...
Fully Remodeled Elegance in Wailea 2Bed 2Bath
Welcome to The Palms at Wailea, where we offer you exceptional experiences in a variety of realms that exceed your expectations. Nestled within the prestigious Wailea town, our villa complex exudes charm, luxury, and allure.Nestled within the exclusive town of Wailea,...
Waipouli Beach Resort Exquisite Oceanfront! Ground Level AC Pool
Oceanfront! Live the Dream! Ultra Luxury "Beachfront" Ground Floor Unit A104 at Waipouli Beach Resort & Spa offering stunning full oceanfront views from every room, with watercolor sunrises, whale watching and romantic dinners on the lanai with a 180 degree lush green...
Vacation Home in Ko Olina Resort by RedAwning
Ko Olina Kai is a peaceful gated community that offers all the tranquilprivacy you could desire! The interior is spacious and homey with 2 bedrooms,2 baths, a living room with an adjacent dining space, and a kitchen. Thisoutstanding villa offers sleeping accommodations...
ICC 20 Remodeled 2Bedroom Hawaiian Cottage w Pool AC
International Colony Club 20 Fully Remodeled Hawaiian Cottage- Walk to Beach & Steps to the Pool! 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 Sail,...
Exceptional Ocean Views - Renovated - Maui Kamaole #G-114, 1 Bd/2 Ba/ (Sleeps 2)
Welcome to your slice of paradise! Incredible ocean views, quiet, private and relaxing. The perfect place and location to call home during your stay in Maui. Note: Travelers to Hawaii will no longer be required to quarantine for 10 days provided they can provide a...
1 BR BEACHFRONT Luxury Condo at Kaanapali Beach: Escape the Crowds, Full A/C
The Mahana at Ka'anapali Beach Unit 818, Lahaina, MauiEscape the crowds of Maui resorts and enjoy private spectacular floor to ceiling views of the Pacific from this beautiful spacious 900 sq. ft. 8th 1 bedroom oceanfront luxury condo located on Kaanapali Beach, rated...
Direct Oceanfront View! Walk on Beaches - A/C
Watch the palm trees sway and whales breach from this beautifully renovated direct oceanfront unit just steps away from the white sand beach. Unobstructed panoramic views of the ocean and outer islands. Enjoy stunning year-round sunsets all from your living area and...
Lanai Building w/ AC! 100% Oceanfront -The Mahana 8th floor, 1BR/2BATHROOMS!
The Complete Maui Experience! The Mahana Resort - If you are familiar with West Maui, you will already know The Mahana is truly a premier property with spectacular oceanfront views. Just steps to the sandy Kaanapali beach, you will be led on a two and one half mile...
Tranquil Golf Course Townhome Ko Olina Kai Estates w/Great Amenities by Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to your luxurious retreat nestled within the exclusive Ko Olina Kai Golf Estates and Villas gated...
Fairway Villas Waikoloa G31-Top Floor Villa w/loft and 2025 Hilton Pool Pass!
Quite Top Floor End 2 BEDROOM 2 BATH Villa WITH A LOFT located in Fairway Villas Waikoloa in the Waikoloa Beach Resort on the Kohala coast of Hawaii island. NEW Luxury Vinyl Plank Flooring just installed, NEW living room furniture and new photos coming soon. This top...
Waiulaula Villa Mauna Kea -Previous Model - Ocean, golf & mountain views!
Welcome to Wai'ula'ula' at the Mauna Kea Resort!Professionally decorated former model home with mahogany trim and stone upgrades, and now current newer updates and furnishings, offers breathtaking ocean, Maui, and Kohala Mountains views! Located overlooking the Westin...
Tower Standard King at Royal Lahaina Resort
Your oceanfront tropical oasis awaits on beautiful Maui!This listing is for a room within a hotel.✦ Your room is 350 sq. ft, equipped with complimentary toiletries, TV.✦ Daily cleaning services included in the nightly price.There are a few additional details to know...
Charming apartment in delightful Koloa with fitness room, AC, WiFi
This amazing apartment in Koloa is a hidden gem waiting to be discovered by guests.Charming, newly updated condo with AC, just steps from the ocean. Blending historic Hawaiian plantation style with modern comforts, this serene retreat is perfect for families,...
True Beachfront Luxury! Downstairs unit oceanfront 20' to water! NO resort fees.
Luxury Beachfront Retreat at The Pikake in Maui - Ground Floor GemEscape to paradise with our newly remodeled ground floor condo at The Pikake in Maui! Experience true luxury with this one-bedroom, one-bathroom beachfront oasis located on the desirable West side of the...
Ocean View•1 BR Corner Condo•Mins to Waikiki Beach
Experience breathtaking, panoramic ocean views from this stunning top-floor 1-bedroom condo in the heart of Waikiki. This spacious retreat offers an open, airy layout with original hotel finishes, large windows, and a private outdoor dining space perfect for soaking in...
LUXURIOUSLY*OCEANFRONT Beach House with Sweeping 180°Views
Welcome to the Indo Lotus Beach House, where tranquility meets paradise on the "Charley Young" end of Kamaole One Beach in South Maui. Immerse yourself in the sacred and peaceful ambiance just steps away from the Pacific Ocean, offering breathtaking swimming, diving,...
Poipu Beach Top Floor Prime Ocean View Condo w/ Pool, Tennis, Exercise Room
Enjoy a relaxing vacation and a prime unobstructed view of the ocean from our non-smoking top floor, prime ocean view condo on the beautiful white sands of Poipu Beach on the sunny south shore of Kauai. All amenities are provided including your own private lanai with...
Gorgeous Ocean/Molokini View 2Bed/2Bath w/AC in EVERY room!!
Aloha and welcome to paradise! Recently renovated with split unit air conditioning with iWave-m ionizing air purifiers on each head!! Ocean view is absolutely amazing!! Watch the boats going to Molokini Crater year around, and see the whales in the winter, all from the...
I.P.M PRESENTS: VILLA C302 - SPECTACULAR NEW REMODEL + GREAT OCEAN VIEW!
SECURE YOUR RESERVATION WITHIN MINUTESSAFE AND SECURE ON LINE BOOKING AND PAYMENT PROCESS24 HOUR PROFESSIONAL PROPERTY MANAGEMENT SERVICES WAILEA BEACH VILLAS C302 NEW REMODEL COMPLETED NOVEMBER 2023 INCLUDES: New bedroom flooring and area rugs, new living room and...
New Listing! Beautiful ocean view 2bed/2ba Condo on Kaanapali Beach Resort-style
Welcome to our beautiful 2 bedrooms and 2 bathrooms ocean view condo at Kaanapali Shores! Sleep up to 8 guests. Perfect for your family or group traveling together to beautiful Maui.Kaanapali Shores's location in the heart of West Maui where you can find many 5-stars...
Maui Resort Rentals: Honua Kai Konea 726 – Luxurious 7th Floor 2BR w/ XL Balcony & Delightful West Maui Mountain Views!
Konea 726 offers nearly 1300 sq ft of spacious interior living area and an additional XL 350 sq ft balcony. Enjoy gorgeous vistas of the West Maui Mountains and the frequent afternoon rainbows from a 7th floor vantage point.The suite can accommodate up to six guests in...
Waipouli Beach Resort Gorgeous Ocean Front Condo! AC New Sofa Sleeper!
Oceanfront! Priceless and Tranquil Waipouli Beach Resort an Oceanfront 2 bedroom, 3 bath condo at the beautiful #1 Ranked Waipouli Beach Resort & Spa on the island of Kauai.There is Central AC in this condo as well as a full size washer and dryer for laundry!Enjoy Oasis...
Luxurious And Private 3-bedroom/3-Bath Townhome On The Mauna Lani South Course
3-Bedroom, 3-Bath Townhome overlooking the 10th fairway of the Championship South Course at the Mauna Lani Resort.Our condo is located in one of the two most desirable buildings in Golf Villas. It is an end unit overlooking the 10th fairway of the famous South Course....
Remodeled Kihei Condo Steps To The Beach! Kihei Akahi C107
Aloha Kakou!You're going to love staying at this comfortable, clean, and newly remodeled condo at the beautiful Kihei Akahi, Unit C107. This condo is directly across the street from Kamaole Beach 2 and is a short walk to multiple other amazing beaches. Enjoy walking to...
Viva Volcano Village!
Our 1933 Craftsman home is one of the 10 historic homes of Volcano Village. Purched in the canopy of the Ohia forest the songs of the ‘Apapane bird will serinade you from the tree tops around our balcony. Walking distance to stores and restaurants and less than 2...
Kaanapali Alii Unit 416
Aloha and Welcome!! You have arrived at the Kaanapali Alii, the Hawaiian word for 'royalty', and the Kaanapali Alii is one of the finest luxury condos to stay in West Maui. OUR CONDO UNIT HAS A MAXIMUM # OF GUESTS ( INCLUDES CHILDREN AND INFANTS) TOTAL ...
❤️PiH❤️ Sunshine Oasis ★Hilton Passes ★ Closest 4BR to KaMilo pools Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sunshine Oasis, a part of our Hawaiian Luxury Collection. Sunshine Oasis at KaMilo is a wonderful 4 bedroom home (Mahina Model)We pride ourselves on providing some of the most sought after homes on the Kohala...
Simply Beautiful Waikīkī Apartment
*MONTHLY RENTAL* Stay close to Waikīkī Beach, 5 minutes walk to the sand. Our stylish 2-bedroom space is in a secure building with free parking, pool, jacuzzi, sauna and rooftop BBQ area. Highlights include a big balcony, full kitchen, 3 air-conditioners, double...
Kapalua Golf Villas 11P7-8: 2 BR Luxury Condo with Lanai
This is a legally permitted vacation rental according to the County of Maui ordinances.Your Ocean-View Escape in Kapalua – Luxury Condo with Lanai, Golf Course Views & Resort Pools E komo mai (welcome) to your dream Hawaiian getaway, where every moment is infused with...
Montage Kapalua Bay - Grand 3BR Oceanview Villa 2206
** 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...
New Listing! 30% Off - Thru 4/30/25! Beachfront, Family Friendly, AC & Pool!
Welcome to Kahana Village Residence 37, a stunning 3-bedroom, 2-bath unit in West Maui. Offering breathtaking ocean views and an exceptional direct oceanfront location, this condominium provides the ultimate Hawaiian getaway. The lush green space in front of the unit...
Mele Nani Getaway in lovely Volcano, Hawaii
Mele Nani in Volcano, Hawaii is our sweet two bedroom, one full bathroom vacation home. Our favorite spot is the hanging lounger on the covered, front lanai. Gently rock to the bird song all around while sipping your morning coffee. We offer a small wood burning...
Recently Updated Beachfront Oceanfront Condo! Walk to Old Town Kapa'a
Location, location, location! Top level, Oceanfront, Beach within steps, 2 Minute walk into Old Town Kapaa, next to the Kauai's Coastline Bike Path (Ke Ala Hele Makalae ) and A/C! This privately owned Gem features a large waterfront Main bedroom w/ King size bed and...
Kaanapali Alii | 483
Welcome to Kaanapali Alii 483, your perfect luxury vacation rental in Maui. This stunning one-bedroom plus sleeping den condo offers a serene and stylish retreat, ideal for families and couples seeking a memorable island getaway. Begin your day on the private lanai,...
Princeville Luxury Townhouse, modern with A/C.
Welcome to Villas on the Prince #28 a modern Princeville 3 bedroom, 3 bathroom condo situated in a private gated community that has AIR CONDITIONING in all bedrooms and main living areas. Recently updated. Sleeps up to 6 guests comfortably and within walking distance of...
Wyndham Kauai Beachboy Resort | King Bed Studio
Summary:Wouldn’t it be fun if Jurassic Park were real? This resort is the next best thing (think luscious jungle without the ferocious dinosaurs). The island of Kauai provided the background for the iconic Hollywood film, but this resort is all sun, swimming, and spa...
North Shore Turtle Bay Hideoutn - Kuilima Estates East
BRAND NEW RENOVATION. This unit backs up to the world famous Fazio golf courses with a beautiful view of the 18th hole from the relaxing lanai. Just a five-minute walk from the beaches at Turtle Bay Resort and access to miles of walking and biking trails. Turtle Bay is...