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.
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Come relax and enjoy your stay at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui.Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean views...
Ocean Views W/Lanai, WiFi, Cable, Fans–KIA #2179
Recently remodeled and redecorated, this bright and breezy 'home away from home' will make you want to return each year. This 880 square foot space is accentuated with a variety of darker woodish tones featured in the modern rattan furniture to the reddish flooring...
1+ Acre PRIVATE RESORT,4 bed, 3 bath, cinema, spa
Summary:Rated in top 10 Airbnb's on the coast. Treat yourself to a vacation surrounded by unmatched landscaping, ocean view, 2000 sq/ft single level, fully stocked home with 4 bedroom, 3 bathrooms, Movie Theater; a/c in each room, waterfall, grotto, tiki torches, fruit...
Spectacular Oceanfront 3 BR Home - Privacy & Space with Incredible Views!
Kealia Landing sits on a bluff overlooking wide, sandy Kealia Beach with panoramic, unforgettable views of Kauai's east coast extending ten miles to the Hoary Head Mountain range. From this wonderful cul-de-sac in an historic mill community, recreational possibilities...
Exquisite Luxury: Oceanview Penthouse Villa
Beautiful second home of kama'aina family right next to Mauna Lani's white sand beaches with access to a pool, spa, and grill area that face the ocean. This one bedroom penthouse villa, K302, provides utmost privacy and beauty with spectacular pond, ocean, and sunset...
Hale Kalea – Renovated 4BR Luxury Home at Mauna Lani with Pool, Views & Golf Cart
Welcome to Hale Kalea, the House of Joy and Happiness! After many years as a successful vacation rental, Hale Kalea has new owners and we can’t wait to welcome you back!Located in the Mauna Lani Resort’s exclusive gated community of Champion Ridge and perched above...
NEWLY REMODELED! Partial Ocean View condo along the golf course
This newly remodeled 3 bedroom 2 bath condo located in the heart of Wailea is the perfect vacation oasis for your island getaway. This condo comfortably sleeps 6 and has amenities such as 2 outdoor pools each with a hot tub, a full kitchen, wireless internet, air...
Lae Nani 531-Oceanfront View Top Floor with AC
Welcome to Lae Nani Oceanfront Penthouse Unit 531, where paradise awaits! This exquisite two-bedroom, two-bathroom condo promises an unforgettable vacation experience in the heart of Kauai's Coconut Coast. As you step into this Royal Hawaiian-inspired penthouse, you'll...
WHALE'S TAIL -Beachfront in Magical Puako! Ocean playground outside the door!
**SPECIAL FALL RATES**Combine the sandy beach next to your back yard with the thoughtfully placed windows that give you excellent views from nearly every spot in the house—upstairs and down—and you’ll love the Whale’s Tail for your Hawaii vacation. Not only is...
Nihi Kai 802 Sunset Spectacular, Ocean Views, w/AC
NIHI KAI 802 AT KOLOA KAI VACATION RENTALSOcean View Comfort and Convenience in PoipuWelcome to Nihi Kai 802, a beautifully remodeled 2-bedroom, 2-bathroom condo offering breathtaking ocean views and a peaceful setting in Poipu. Perched high on the hill leading to Poipu...
The Catbird Seat -Closest Vacation Home To Poipu Beach - 100 Ft Away!!! Pool!!
The Catbird Seat private paradise home is the closest location to Poipu Beach and Brennecke Beach of ANY vacation rental. 2 Bedrooms sleep 4. Your choice of twin beds or a King in the 2nd bedroom.This ideal spot is just across from the world famous Brennecke Beach and...
Beautiful Newly Remodeled Condo in Kahana, Maui
Beautiful, newly remodeled one bedroom condo that sleeps four in Kahana, Maui. Situated in Keoni Nui bay with magnificent views of Lanai, just steps from a beautiful pool and beach just for the condominium complex. The condo (#C3C) features a large kitchen, California...
Hale Ka Mahina, walk to Hanalei Bay & town. TVNC-1115
Upgraded in 2019, Hale Ka Mahina isn't your average vacation rental, Hale Ka Mahina is tucked away on a side street between Hanalei Bay and Hanalei town. Easily walk or ride bikes to the beach and town when you want to check the surf or grab a coffee at the Hanalei...
Colorful & open condo w/free WiFi, furnished deck, & shared pool - near golf
Mauna Kai 6BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a taste of the tropics inside this open, colorful, and very inviting condo located near golf courses, beaches, and...
Penthouse Sweeping Ocean Views!
Welcome to Maui and the Hono Hideaway home located in the stunning Ka'anapali Shores Resort!See the ocean from every room of this beautiful, top-floor FOUR-story condo in the oceanfront wing of the Ka'anapali Shores resort! You'll feel like you're walking on water as...
4 Pools, A/C, near 3 snorkeling beaches! Gorgeous Kapalua Golf Villa! 25V1 - Quam Properties Hawaii
*Seasonal Special: Stay 5 nights from now until December 15, 2025, and get 1 FREE!Kapalua Golf Villa #25V1 has ocean views on the Kapalua golf course from this 1Br/1.5Ba condo. Updated furniture with a kitchen remodel. There are flat-screen TV's in both the living room...
Luxury Penthouse at Beach Villas at Ko Olina
This penthouse villa has 3 bedrooms and 3 baths and is located on the top/4th floor in the Ocean Tower (O426). The villa has an unobstructed full front ocean view and the private lanai overlooks the peaceful and tranquil koi pond area of the resort. Open the large glass...
Just a couple houses away from the nicest beach on the island.
This rental is across the street from one of the nicest beaches on the island. Don't take our word for it check out the pictures of Waimanalo Beach and Bellows Beach. Kitchen has everything you need and opens up to a dinning table to enjoy your meals or you can take...
Ko Olina Beach Villas B506 by Gather: Luxury 2BD 2BTH w/ Ocean Views
Welcome to Ko Olina Beach Villas B506 by Gather, an elegant two-bedroom, two-bathroom villa located on the fifth floor of the renowned Ko Olina Resort. With space for up to six guests, this stunning vacation retreat offers a blend of luxury and island charm, making it...
New Listing- Spacious, Remodeled Direct Beachfront with A/C & on Sandy Beach
Our condo is zoned "Hotel/Resort" so no need to worry about our zoning.Hear the Waves....Lay in bed and listen to the waves! Spacious condo with direct beach & ocean view. A Sandy Swimmable beach is right outside your door. *** Book with confidence! You will be offered...
Maui Resort Rentals: Honua Kai Konea 406 - Extra Large One Bedroom Den, Partial Ocean and West Maui Mountain Views!
Konea 406 is an expansive one-bedroom suite boasting views of what West Maui is most famous for, the blue Pacific Ocean and the lush West Maui Mountains.An additional den area offers fantastic value unique to this class of suites at Honua Kai.When it's time to rest, the...
Wai Lani: Ocean View Home, AC & Lanais
Welcome to Wai Lani by Gather, your serene retreat at the end of Albert Road in Princeville, Hawaii. Overlooking the vast Pacific Ocean, this stunning home offers breathtaking ocean views from every room and lanai, immersing guests in the tranquility of lush tropical...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | 1-Bedroom Condo, Recently Remodeled! KGV-20T8
Kapalua Golf Villa offering ocean views, gourmet kitchen, spacious bedroom, and peaceful resort amenities-ideal luxury retreat.*Special Offer - Book any KBM rental home in Hawaii for 6 nights or more with an arrival date between Jan 1 - Dec 31, 2025 & receive a...
Location, Location, Beautiful AC Beach Studio In Hilo; Few Steps from Beach Cove
WHY STAY ANYWHERE IN HILO BUT CLOSE TO BEACHES AND OCEAN WHERE THE WEATHER IS BEST!!! Lovely beach studio located a minute walking distance to ocean with small swimming cove and tide pools. The studio is AC comfortable which ensures cool and comfortable days and...
Mesmerizing Oceanfront 2 Bedroom | 2 Bathroom with Central Air
Lanikai 134 – Mesmerizing Oceanfront Top-Floor Retreat with Central A/CWelcome to Lanikai 134, a spacious third-floor oceanfront condo offering breathtaking views of Wailua Bay and cool comfort with central A/C throughout. With two bedrooms, two bathrooms, and a...
🏖 ❤️ LARGE LUXURY GROUND FLOOR LUANA VILLA,POOL VIEWS, GRT LOCATION & Reviews❤️
🌺 You are renting directly from the owners. We would love to have you stay in our villa. Enjoy all the amenities that Honua Kai has to offer. 🌺 One of the closest Luana Villas to the ocean. 🌺 Over 40 great reviews! Please read what others are saying about our...
Menehune Shores #119 – Stylish Oceanfront Retreat with Luxe Modern Finishes
Menehune Shores #119Experience effortless oceanfront living at Menehune Shores #119, a welcoming ground-floor condo with beautiful views and direct access to the grassy lawn and beach. This two-bedroom, two-bathroom retreat is thoughtfully designed to offer comfort,...
Walk to Pipeline Rocky Point and Waimea
Beachfront property on Northshore Oahu. Beautiful home on the beach with close access to numerous activities. Gated property with lots of privacy, beachside lanai and memorable sunsets. House has 3 Bedrooms and 2 full Bathrooms with ac in all rooms included. Covered...
Aloha Condos, Kanaloa at Kona, Condo 2204, Oceanfront, AC
Kanaloa at Kona Condo 2204 is a dream! With breathtaking ocean views and luxurious amenities, this condo exceeds expectations. Guests love the well-appointed kitchen, comfy furnishings, and thoughtful extras like beach gear and toiletries. The lanai is perfect for...
Lae Nani 512 Gorgeous Ocean Front Ground Floor in Building Five With AC
Lae Nani is a premier property on the Coconut Coast centrally located near grocery stores, galleries, restaurants, small boutique shops, etc.Our condo is on the ground floor in Building Five and here are some of the features:-Location Location Location-Air Conditioning...
Hale Kahawai & Ohana By Parrish Kauai - great family space with AC and private p
Enjoy a relaxing and fun filled vacation in one of the newest homes in the centrally located Poipu Beach Estates neighborhood. This five bedroom residence consists of a three bedroom main home and a private two bedroom Ohana located above the detached...
Majestic Mahakea – Oceanfront Oasis on Oahu's North Shore
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 Majestic Mahakea: Oceanfront Oasis...
⭐️ NEW KITCHEN - Large lanai with best views of sunsets, pool & grounds ⭐️
Spectacular, nicely decorated, across the street from Kamaole Beach III in Kihei!Feast your eyes on this fabulous condo with a lanai to die for.Enjoy this spacious and tastefully furnished 818 sq. ft. condo with views of the pool, tropical gardens and sunsets. The unit...
KBV 15B2 2BD Kapalua Breathtaking Panoramic Ocean views
Kapalua Bay Villas 15B2 NEW LISTING! Breathtaking 2 Bedroom, 3 Bathroom with Panoramic Ocean views in the heart of Kapalua FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watch...
2Bed/1Bath Upstairs Home, 1mile to Beach, Next to State Forest, Custom Finishes
There is a black sand beach nearby to explore (Kehena), and a lava tube hidden in a kipuka surrounded by a lava field, and geothermally heated ponds, forest trails, farmers’ markets, yoga classes, chocolate and mushroom farms, dances, waterfalls, drum circles and...
Oahu North Shore 2 BR Oceanfront Retreat at Sunset Beach
Escape to the stunning shores of Haleiwa and experience the ultimate beachfront getaway at our charming vacation rental. Nestled along the pristine sands and turquoise waters, this slice of paradise offers an idyllic setting for relaxation, adventure, and unforgettable...
Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
Aloha. Have you noticed how we're constantly towards the top of Kihei and Kihei Kai Nani searches. Well, vrbo has a system of metrics they use that ranks all listings, basically putting the best units available in front of guests...and we're crushing those metrics and...
Maui Resort Rentals: Honua Kai Konea 705 - Upgraded 7th Floor Interior 2BR Suite w/ Unobstructed Ocean Views!
Konea 705 is a luxurious 7th-floor "penthouse" interior courtyard two-bedroom suite boasting unobstructed views of the stunning blue Pacific from its prime vantage point high above the palm canopy. In addition, this suite has one of the rare Honua Kai two-bedroom...
AC Ocean Views- Steps to beach
Experience beachside living in this top-floor 1-bedroom condo at Kiahuna Plantation, Poipu Beach, Kauai. Enjoy ocean views and cooling trade winds through oversized louvers. The lanai features chaise lounges, and the living room includes a queen sleeper sofa and TV. The...
Ho'okipa Villa: Historic Home + Guest Cottage in Kahala
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.Kahala Luxury Living Welcome to Ho'okipa...
Romantic getaway directly on Napili Bay-Beachfront-5 Stars-Best Location
Fall head over heels for the enchanting Napili Bay at "The Aloha Bungalow," a newly renovated ground-floor beachfront studio condo overlooking the turquoise waters of one of Maui’s most beloved beaches. Nestled in the heart of Napili Bay with its soft, golden-sand...
🏖️Newly Renovated | Gorgeous area and condo | Concierge Included | vrKCV
vrKCV - The Shores at Waikoloa 231, Professionally Managed by Kona Coast VacationsAloha and welcome to Shores at Waikoloa Beach Resort Unit 231! This beautifully updated 1-bedroom, 1-bathroom condo offers a relaxing getaway in the heart of Waikoloa Beach Resort. Enjoy...
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
• Oceanfront• Split A/C units• King bed• Remolded Feb 2020• Beach access from condo complexFully remodeled in February 2020, this bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei unit 213 welcomes you! This second floor condo...
Lovely garden cottage, Hamakua waterfall district, 100% solar
Secluded Ohana (1/1 Cottage) with Superb Ocean Views on Gorgeous Hamakua Coast Estate – The Garden House HideawayConstructed of Indonesian hardwoods, this fully furnished Studio Ohana sits on the beautifully landscaped grounds of an estate overlooking the beautiful...
NEW HOME in Private Community with Ocean/Mountain Views. 5 Min. Drive to Beach
BRAND NEW HOME located in a gated community in Mākaha Valley, with beautiful ocean and mountain views. Just a 5 minute drive to Mākaha Beach for swimming, surfing, boogie boarding or just relaxing. Home is equipped with all you need for a day at the beach. This 4...
Amazing Ocean View, In Kihei, Top Floor, AC, Across St from beach
Aloha! We are the owners of a gorgeous, remodeled penthouse, 1 bd 1 ba (sleeps 3) condo with amazing ocean views inside and out. I to 2 minute walk from beach. It is decorated with a feel of the island throughout. New sound resistant glass balcony doors, windows and...
Nihilani 16C - 3 bedrooms with AC
This gorgeous 3 bedroom, 3 bath townhouse located in the Nihilani complex in Princeville is the perfect spot for your family vacation. Spacious and inviting, the home has air conditioning throughout, a fully loaded kitchen, a large living area to enjoy and just about...
G110 - Ground floor, close to ocean and all amenities, great view
G110 is a very popular and frequently requested unit. It’s a completely renovated studio and an extremely beautifully appointed unit. There’s a fully equipped kitchen and bar area, granite countertops and top of the line stainless steel appliances including a fridge...
Puamana 177-3 – Elegant Garden Retreat in South Puamana
Escape to the tranquil beauty of Puamana in this tastefully remodeled 2-bedroom, 2.5-bathroom townhome, ideally located in the lush, tropical oasis of South Puamana—untouched by the 2023 Lahaina fire. This peaceful location offers quick access to the nearby beach,...
Beautiful 2 Bedroom, 1 bath, full kitchen, secluded acre of gardens
Aloha and welcome to my Hawai’i Island cottage! I am delighted to share my 1 acre of rainforest and hope you will choose to stay at Hawaiian Paradise Cottage.Enter the property through a private electric gate and down a tree-lined drive to a secluded garden oasis set...