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.
Family Retreat in Mākaha Valley | Sleeps 14 + Beach Gear
Come experience authentic Hawaiian hospitality at Makaha Valley Hale Kai, a property proudly owned and managed by a local resident. By staying with us, you are directly supporting the local community. This 4-bedroom, 3.5-bath retreat sleeps up to 14 and blends the ease...
Peaceful Hawaii Paradise three minutes from Beautiful Beach
Large Studio with roomy bathroom beside a quiet home. Enjoy your coffee on your own patio near the pool overlooking the canal where you can kayak or paddle board to beach. Quiet and clean. We supple you with a start of necessities. Walk to market and excellent...
Tropical Heaven! Spacious, Poolside & Views. Exclusive Hilton Pool Pass for '25
Escape to paradise at our luxurious 3-bedroom townhome in the private, gated complex of Waikoloa Beach Villas, located on the breathtaking Kohala Coast of the Big Island. Our poolside unit is among the largest in the complex and boasts 1,872 sq. ft. of indoor living...
Sugar Beach Resort Oceanfront Luxury Condo - Your new vacation home!
The condo is on the 5th floor of the Plant ation building #532. It is a roomy 700 square feet with full designer kitchen, living room, lanai, bathroom, and bedroom, with its king size Serta iComfort memory foam mattress. You will enjoy the incredible panoramic ocean...
MRR Presents Kaanapali Ali'i 271 - Interior Courtyard 7th Floor 2BR w/ Stunning Direct-Facing Ocean Views!
Boasting a premier 7th-floor location in what is considered one of the best interior stacks at the entire resort, suite 271 delivers gorgeous direct-facing views of the Pacific Ocean, as well as views of Maui's neighbor island Lanai and the lush Kaanapali Alii...
Royal Kahana 1010 May & June Specials at Remodeled Oceanfront Condo Getaway
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Royal Kahana 1010, a stunning tenth-floor corner residence where uninterrupted ocean views stretch from the golden coast of...
SUMMER Value 10% OFF 7nt+ stays, AC, 1st Fl, Remodeled, Oceanfront complex
Maui Sunset B103 - 1 bedroom, 2 bath, Ground floor condo.California King in bedroom and Queen Murphy bed in living area.Get-a-way, Reunions, Family friendly, Couples, Seniors, Honeymooners, Work-cation; all enjoy a welcoming experience.Escape to the stunning beachfront...
Sugar Beach Resort 301: 3rd Floor Ocean View Condo in North Kihei, sleeps 4
A special corner condo with Ocean Views. This condo is located at the end of the building, so it has an extra window in the living area, allowing more natural light to flood in. This bright and open condo is the perfect space to relax. This one-bedroom condo has many...
Unforgettable Luxury Awaits: Hokulani 310 - Modern Retreat with Ocean Views!
Special Offer for Extended Stays!Escape to the islands this fall and enjoy exclusive perks designed to make your stay even more relaxing:-No Resort Fees-No Parking Fees-Complimentary Mid-Stay Clean for stays of 14 nights or moreWhether you're planning a quick getaway or...
Quaint Lanikai Cottage! Such a gem!
This is a legally established property, please read below for more info...This cute quaint cottage is perfect for a vacation! It feels of beach house when you walk into it. With in walking distance to many beach access points along Lanikai beach. Luxury views and...
Paradise Captured ...Discount Weekly and Monthly
Bring your friends and family to a hidden Paradise. Live in the natural canopy of the wild of the Hawaiian terrain. While being only twenty minutes from the finest restaurants on the island. You are centrally located on the island, which gives you easy access to the...
Beautiful, Tropical Vacation Rental in Keauhou! STVR-19-366304.
This beautiful tropical vacation rental in the Keauhou Resort area of Kailua-Kona, HI is only a block away from stunning Keauhou Bay and across the street from the Kona Country Clubs wonderful ocean golf course. Walk to Keauhou Bay and jump on the Fairwind snorkel...
Incredible View in Hilo - Pool, A/C, Remodeled #708
This 1 bd, 1 bth condo is located right in the heart of Hilo with gorgeous views of treetops and sparkling blue waters. The condo was just painted and new laminate flooring was just installed.Brand new to the market! This condo overlooks Wailoa River State Park and you...
Maui Resort Rentals: Honua Kai Hokulani 748 - Upgraded Top-Floor 2BR w/ Partial Ocean AND West Maui Mountain Views!
Hokulani 748 is an upgraded top-floor, two-bedroom suite offering stunning Partial Ocean views as well as views of the lush West Maui Mountains. Located only one column back from oceanfront you will find that this suite is well situated to enjoy what Maui is known...
Beautiful Oceanfront #216 At Sugar Beach!
Our Maui home is a fully stocked non-smoking one bedroom condominium on the longest beach in the state of Hawaii. Listen to the gentle sound of the surf and watch the sun set from the chair on your private lanai. Walk the five miles of white sand beach and swim right...
Vista Waikoloa Penthouse With Privacy And Wonderful Views
Our CondominiumOur condo at Vista Waikoloa complex is surrounded by beautiful views of the ocean, lush gardens, palm trees, and fairways of the Beach Golf course in the famous Waikoloa Beach Resort. From the front door you can walk to the ocean, shops, restaurants,...
Direct Ocean Front, Incredible Views, Perfect Couples Getaway, Split AC
Enjoy panoramic oceanfront views from Maalaea Kai 311, just 50 feet from the shoreline. This updated 1-bedroom, 1-bath condo features tropical decor, split A/C in the living room and bedroom, high-speed Wi-Fi, and all the comforts of home. Relax to the sound of waves...
Condo in Kapalua!!
This villa is located in the prestige area of Maui between the Ritz Carlton and Montage! The two-level villa is located on the second floor overlooking the 9th Green of Kapalua's Bay Course, with views of the Ocean and Molokai, and the West Maui mountains. From the...
Kuhio Shores Oceanfront Corner Unit
Beautiful oceanfront Poipu condo in the closest complex to the water. This ground floor corner unit in Kuhio Shores offers stunning ocean views from every room, with the seawall and water just steps from your lanai. This condo features one bedroom with a king bed,...
New Listing! Marina-front Home Near the Ocean w/Private Pool & AC: Nani Wai
Nani Wai is a five-bedroom, four-bathroom private retreat tucked into the prestigious Hawai‘i Kai neighborhood of Honolulu, O‘ahu. With its enviable waterfront perch on a private marina and unobstructed views of Koko Crater, this gated home delivers a seamless blend...
Enjoy the Gorgeous Mountain, Canal and Golf Course Views #2120
* Please note: the shower temperature may fluctuate between warm and lukewarm even after setting it, but it’s still fully functional for showering. * Please be advised that there may be unplanned water outages without prior notice from the building...
302 - SPECTACULAR RENOVATION WITH A/C -BREATHTAKING VIEWS! 1 bed 1.5 bath unit
THIS STUNNING OCEAN FRONT CONDO WITH A/C has undergone a gorgeous renovation – a MUST SEE!!! Welcome to your “home away from home” as you relax with the cool colors and clean lines of this elegant, yet comfortable renovation. Unit 302 now includes the finest...
New Listing! 1 Bedroom, 2 full bathrooms in beautiful Puamana w/2 Paddleboards!
This home is located down an adorable street within the historic Puamana community. Its location is excellent being steps away from one of the 3 pools. Enjoy the relaxing lanai which includes a new outdoor sectional couch to relax on. Puamana is known for its private...
Call Diamond Head Hidden Paradise booking req.
Call/ sms direct 4152519696 other than 30-days interest for accurate rates and availability. Reservation from the platform is limited.Hidden Diamond Head Paradise located in the Diamond Head District, is nestled above world famous Waikiki Beach, in a secluded, tropical,...
Unique Home with Beautiful Ocean View
This unique home is nestled in quiet one block neighborhood with an ocean view from the back lanai (porch). Being just eight short miles north from Historic Hilo you get the convenience of being close to town and still having your privacy.Also not far away is Akaka...
Newly remodeled 3 bedroom, snorkel in private cove, walk to top rated beaches (Unit 217)
Honokeana Cove unit 217 is located in one of the most picturesque settings on Maui. Our unit is steps from Honokeana Cove, one of the best snorkeling areas on the island and home to many giant green sea turtles. We are located within walking distance to several beaches,...
A BEAUTIFUL OCEAN FRONT RESORT CONDO!
Waipouli Condo A101 is a large 1 bedroom, 2 bath condo with Central AC. Located in Kapaa Town, walk to shops, restaurants and beaches. Complimentary Wifi & on site parking, King bed and queen sofa sleeper, washer/dryer in the unit. Comfortably Sleeps 4.The space...
FULLY UPGRADED 2BED/2BATH BREATHTAKING VIEWS ACROSS FROM THE BEACH
Welcome to Paradise! This fully upgraded 2 bedroom, 2 bathroom condo has spectacular ocean views from the spacious lanai located in the highly sought after Maui Parkshore Condo Complex. We are unit 309 on the third floor. Our kitchen is fully equipped for your...
🏖️Spectacular Oceanfront Views | WIFI | Free Concierge | vrKCV🏖️
vrKCV - Sea Village 1103, Professionally Managed by Kona Coast VacationsOceanfront Ground-Floor Condo – Sea VillageWake up to the sound of gentle waves and enjoy concierge service that makes every moment of your stay effortless. This oceanfront ground-floor condo...
Great OCEAN VIEW... Walk to beach and GRAND HYATT....NEW RENOVATION FOR 2024
Newly RENOVATED baths and kitchen...stunning. Absolutely one of the BEST VIEWS, in Poipu Sands, from this second floor OCEAN VIEW condo. Poipu Sands is a low density condo development, featuring wide open green lawns leading down to the ocean. This unit has the largest...
City Lights, Mountain View! Ilikai Hotel, One-Bedroom, Renovated & updated!
This condo is located on the 17th floor of the Ilikai Hotel. Your piece of paradise awaits, in this modern remodel that will please any guest with it's quality & attention to detail. As soon as you walk into the condo, you'll be welcomed by a clean & spacious living...
Piece of heaven ! Enjoy the sounds of ocean and beautiful sunsets. Explore the nearby beach.
Ocean and Coastline ViewsWake up to the sounds of the ocean and the warm tropical breezes as you begin your vacation in paradise. This ocean side, spacious 3 bedroom/3 bath, 2-story condominium offers non stop views from sunrise to sunset.Hale Kai Okona 4 is beautifully...
Maui Resort Rentals: Honua Kai Hokulani 447 - Luxurious 4th Floor Interior Courtyard 2BR w/ Full Ocean Views!
Hokulani 447 boasts an incredible 4th-floor interior courtyard location with full ocean views above the palm trees. Gather, reconnect, and celebrate in this spacious 2 bedroom floor plan which offers an abundance of interior living space with an additional 235 sq ft of...
NP B37 Relax Recharge at Remodeled OceanFront 2BD w Ocean Views Pool
Napili Point B37 REMODELED 2Bedroom Ground Floor w/ Ocean Views, AC & Pool in Napili 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, Alpaca Farm...
Beautiful Ocean View Condo at Prince Kuhio in Paradise - Great Value
Location, Location, Location! This very well maintained, lovely one bedroom Prince -Kuhio condo #303, has a great view of the ocean less than 100 feet away. It is located on the third floor of the Prince Kuhio and there is no elevator in the complex. We also own #111 on...
The beach is waiting! Super cute unit,1 min walk to the beach across the street
This inviting condo provides you with a comfortable, easy and convenient way to enjoy your stay. This super cute unit is located in an excellent location between Kaanapali and Kahana/Napili. The unit is across the street from Honokowai Beach Park, only a 1 minute walk...
Kolea Villas 15M Luxury 2 BR, 2 BA, Direct Beach Access. Within Waikoloa Beach Resort.
Kolea Villas 15M Luxury 2 BR, 2 BA, Direct Beach Access. Within Waikoloa Beach Resort.Kolea Villas is unique in that has direct access to the beach, Anaeho'omalu Bay or better known as A'Bay. This quiet villa is a beautifully decorated and fully air conditioned. 15M is...
A Whale Crossing Vacation Rental North Shore, Big Island
A Whale Crossing Vacation Rental is tucked away in the serene North Kohala region, near Upolu Point on the northwest tip of the Big Island. This charming, secluded getaway offers a peaceful and intimate setting, perfect for those looking to experience the natural beauty...
Luxury Unit Pili Mai 7F With Horizon Ocean Views. Fully Air Conditioned!
Located in the Poipu Resort area, Pili Mai 7F is situated on 35 acres of landscaped lawns and gardens filled with tropical flowers. Enjoy an open air gathering place with barbecues, air conditioned work out facility, and a large swimming pool, spa, and kiddie spray...
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Conveniently located in S Kihei across from popular Charles Young and Kamaole 1 beach and park, this 2-bedroom unit is colorfully decorated and well appointed for vacation enjoyment. Includes central A/C in all rooms of the condo, remodeled master shower, full kitchen...
Makana Lei: Recently Upgraded Home w/ Private Pool, AC & Garden Views
This beautiful Princeville vacation rental home boasts a private pool, indoor and outdoor living spaces with tasteful new furnishings, ceiling fans in every room, and air conditioning in primary bedroom and the living area. Situated in a quiet location with convenient...
Beachfront Penthouse #25 at Sugar Beach Resort --Stunning Views, Fully Renovated
This fully remodeled 1bd/1ba penthouse (PH 25 on the 6th floor) in the Mill building at Sugar Beach Resort is beachfront with direct ocean views as soon as you walk in the door. You can whale watch from the lanai or take an easy elevator ride to the first floor where...
Island Surf Resort, breathtaking ocean view, in the heart of the action
This ocean view condo with a generous lanai at the Island Surf resort in Kihei is just steps away from amazing beaches and in the perfect location for enjoying all South Maui has to offer. Open the gigantic sliding glass door to soak in the sounds of the beach and the...
North Shore Condo With Sunset amazing Ocean Views!
Welcome to your ultimate oceanfront escape at The Cliffs at Princeville—a top-tier vacation destination perched above the Pacific on Kaua‘i’s lush North Shore. Conveniently located just minutes from world-renowned beaches, iconic surf breaks, scenic trails, and...
Watch Whales and Sunsets from your Oceanfront Lanai- Maui Kai 301
This condo is hotel zoned and complies with all current Maui County ordinances and regulationsOceanfront Corner Unit with Panoramic Views – Your Maui Paradise Awaits! E komo mai (welcome) to your perfect Hawaiian escape, where the soothing melody of waves greets you...
Alii Kai 7201: 2BR Paradise w/ Spectacular Ocean Views & Comfortable Living
Welcome to Alii Kai 7201 by Gather, a serene Princeville retreat for four, featuring breathtaking ocean views and lush amenities for an unparalleled island experience.Nestled on the bluffs of Princeville, Alii Kai 7201 opens its doors to a blend of comfort and island...
Walk to Beach: Paniolo Hale Townhome w/ Ocean View
Beachfront | Pool Access | Ocean-View LanaiAdopt an island lifestyle and say ‘Aloha’ to relaxation and beach days with a stay at this Maunaloa vacation rental. This 2-bed, 2-bath townhome sits right on Kepuhi Beach and offers beautiful ocean views from every room....
Maui Resort Rentals: Kaanapali Alii 1105 – Elegantly Remodeled 2BR 10th Floor Oceanfront Gem, Breathktaking Views from Black Rock to Lanai and Beyond!
Boasting a breathtaking 10th floor oceanfront vantage point, this stunning residence delivers awe-inspiring Pacific Ocean views that stretch from Molokai to Lanai and beyond. Enjoy one of West Maui's world-famous sunsets any time of the year right from the comfort of...
Waipouli Beach Resort Luxury Ocean View Condo
Oceanview! This Beautiful Oceanview 1 Bedroom, 2 Bathroom Condo A301 is located in A Building within steps to the Beachfront at the Top Rated 1st Class Waipouli Beachfront Resort & Spa on the beautiful island of Kauai.There is Central AC in this condo as well as a full...
Wailea Ekahi 1C - Wonderful 1bd/1ba / Close to the Beach / Sleeps 5
Oceanfront complex, one-bedroom, one-bath, single-level, ground-floor corner unit.Quiet location. No traffic noise (you are in paradise, there should be none). The condo is located in the 'Lower Village' just steps from one of the 3 quiet pools, close to the beach and...