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.
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
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 Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
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...
Poipu Palms #102 Oceanfront, pool, near beach
Part of the intimate Poipu Palms condo community, this tropical property stuns with incredible ocean views. Out on the private lanai, gather with your ohana to sip on a cool drink and let the ocean breezes lull you into complete relaxation mode.Whip up meals in the...
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 Elegance: Prime Spot
Summary:--------------------------------------------------------- Experience tranquility in this shared Kailua Kona room, a mere stroll from the beach. Embrace the serene island vibe and cozy interiors. With convenient beach access, it's an ideal spot for a peaceful...
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...
Waimea Beach Cottage by Destination Kauai - Charming 2BD, A/C, Walk to Ocean/Pier
TVRNC-1316E Komo Mai, Welcome to Waimea Beach Cottage!This charming cottage and yard are privately yours to enjoy. Fully updated, there are two bedrooms each with a queen size bed and split unit AC for cooling off on Kaua'i's west side. The living area is cozy and...
Amazing! Beautiful Ocean and Bali Hai Views! Bright and Spacious Two Bedrooms
Pali Ke Kua 223 COMPLETELY REMODELED.Right on a bluff overlooking the the beautiful ocean and Bali Hai mountain views! The condo is split level with stairs down to the living area and first bedroom and stairs up to the second bedroom, each bedroom has an ensuite full...
Beautiful Ocean View, totally remodeled Condo! SEE OUR REVIEWS!!!
Papakea Resort is a beautiful complex located on 13 oceanfront acres of lush tropical landscaping. ***New Bathroom counter/cabinet remodel******We installed a beautiful new tiled shower with solid glass door! July 2014***Our beautiful studio offers all the luxuries of...
Hale Kamaole 172 Ground floor condo, easy access to best beach on Maui!
Beautiful ground floor unit with Ocean View from lanai, close to the pool & easy access to BBQ. New wooden flooring.The unit sleeps 2 people. Unit 172’s living room area, offers comfortable couch and 2 sitting chairs, also a large flat screen TV. Up to date kitchen...
Waipouli Beach Resort Exceptional Condo Pool View Condo
Gorgeous Pool View! The Experience: Exceptionally well decorated, featuring Tommy Bahama furnishings. 2 King Beds and a queen Sofa SleeperThere is Central AC in this condo as well as a full size washer and dryer for laundry! Come indulge your senses on the enchanting...
Stunning 3 BR Penthouse: Ocean Views, AC, Lanais, Steps to Beach
Escape to South Maui & feel the warm Aloha when you treat yourself to this slice of Hawaiian penthouse! This corner unit boasts huge 1145 sf fits 8 comfortably inviting guests to bask in sunny wide views and glorious sunsets from either of 2 unobstructed balconies:...
Unobstructed oceanfront: sunsets, whales, breezes
Maui Kai 204 is a newly remodeled 1-bedroom, 1-bathroom condo that features a new fully stocked kitchen, bathroom, floors, ceiling, furniture, and appliances. With a king-size bed and two twin couches (day bed), this condo can accommodate up to 4. guests Open the double...
Clean and Beautifully Remodeled at Maui Kaanapali Villas-Sleeps 4 **
Lofted Condo, 1 Bedroom + Convertible single bed(s), 2 Baths, (Sleeps 4)Kaanapali Beach was rated #1 beach in North America and the island of Maui is rated #1 island in the world!We also own the unit right below B133 if you have additional friends or family joining you....
Tropical Garden End Unit A/C with Ocean & sunset Views! Walk to Keawakapu Beach!
Attention: Beach Lovers! Our condo is in the best location in the sunny beach town of South Kihei, bordering Wailea and across the street from the most beautiful sandy beach on Maui...Keawakapu Beach. This unpretentious Maui complex has a wonderful Hawaiian feel with...
Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,
The fabulous Keawakapu Beach is just a short 10 min stroll. The Palms at Wailea is a gorgeous property with a large pool and hot tub. A magnificent view of the ocean from the pool area. Unit #1801 is a spacious 2 bd, 2 ba ground floor unit. It has a fully-equipped...
Beachfront, Peek-a-Boo Ocean Views, Washer/Dryer, A/C, Wi-Fi!
Waikiki Shore #308 – 2161 Kalia Rd.NEW TO OUR INVENTORY! You'll adore this beautiful one-bedroom condo (706 sqft) right on the beach in Waikiki! Just imagine stepping right from the building onto world famous Waikiki Beach! After a day shopping or relaxing on the...
Honu Hideaway, Maui Kaanapali Oceanfront Penthouse
Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every nightLocated on the top 10th floor with close touch to ocean...
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Situated on a well groomed acre, Luana Cottage offers privacy as well as easy access to hiking, swimming, and exploring the beautiful Eastern side of Maui. Reverse Osmosis drinking water and solar hot water (with electric backup), along with a complete kitchen and...
Elegant & Serene Wai'ulu Villa 115D w/AC, Resort Pool & Golf Course Views
A design lover's dream, this 3 bedroom, 3.5 bath home is among the top tier of luxury villas at Hualalai. The warm color palette and design features of this villa were inspired by a painting that hangs in the living area titled "The End of a Perfect Day". The design...
NEW RENTaL! Experience Aloha *Hawaiian Style Hale*
High quality rental with Hawaiian Style home feeling. Upgraded kitchen. Fresh and clean. Relax and enjoy.PLEASE NOTE: Our prices include TAT/GET tax - Perfect for 1-5 people. This is a fully furnished guest 2 bedroom/1 bath house w/ full kitchen and has nice tropical...
Hilo, Hawaii Getaway
Enjoy the quiet beauty that surrounds this property. From the deck, you will be captivated by the sight of Mauna Kea and the tropical vegetation that landscapes the grounds. There is even a lawn to do some serious putting practice. A quick five minute drive will take...
Kona Hawaii's Most Unique Ocean-View Vacation Home...Sweeping Ocean Views
Welcome to Villa LongBoard – Kona, Hawaii’s most unique and unforgettable vacation rental experience!Perched hillside on the gentle slopes of Mt. Hualalai, Villa LongBoard offers breathtaking panoramic ocean views, serene tropical breezes, and an atmosphere unlike...
Lovely Ocean View Second Floor End Unit, Great Views, Tennis Club Included
Unit 25 has certain attributes that make it especially desirable. It has recently been remodeled to improve the white water views while keeping the unique Kiahuna style redwood trim throughout. This is a second floor unit, which provides more privacy than the ground...
BEAUTIFUL OCEANFRONT MODERN West Maui Condo with Sunset Views!
Location! Location! Location! Ideally situated between famed Ka'anapali and Lahaina to the south and Kapalua to the north. At those locations you will find some of the best beaches, dining, shopping, golf, and water activities to be found in all of Hawaii. Our...
Ocean and Mountain Views - Spacious Cliffs 5-301 - 2 BR/2 BA
Perched on a bluff above the beautiful Pacific Ocean, Cliffs 5-301 is on the third floor (no elevator) with King bed in the Master bedroom and 2 Queen beds in the loft. You can enjoy wonderful views of the ocean and mountains as well as the lush foliage for which the...
Mauna Lani Palm Villas H4 Corner Two-story Villa with Floor to Ceiling Views
The Mauna Lani Resort is a world-famous, four-diamond resort with very nice restaurants, three pristine private beaches and miles of walking and jogging paths, two world-renowned golf courses, sunset cruises, fishing, whale watching, scuba, and the some of the best...
Hale Maluhia - 2 Minutes from the Big Island's Best Beaches
This darling and affordable two-bedroom, one bath house boasts an excellent view of the Kohala Coastline's blue water. Conveniently located in Kawaihae Village just minutes from luxury resorts and numerous white sandy beaches, this home is perfect for a small family....
Updated, Surf-Chic Condo w/ Amazing Mountain/Garden Views & Shared Pool/Hot Tub
Pali Ke Kua #3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'With a gorgeous lanai that opens to views of the mountains and the manicured gardens of Pali Ke Kua, this two-level...
**RENOVATED 07/20!** Corner Beachfront Penthouse in Kapa'a w/AC!!
As of April, 2023 our condo now has AC! Enjoy the Royal Coconut Coast in a 180 degree view oceanfront penthouse!Located on the trade wind side of the Garden Isle, you’ll relax your days away in tropical sun and gentle breezes. Soak in beautiful sunrises on the lanai...
Family friendly condo near beach
This 'Regency at Poipu Kai,' non-smoking, two bedroom, two bath, garden view condo is centrally located in the Poipu area. The lush green surroundings are accentuated with palm trees, ginger, and hibiscus. This secluded, very private condo is a ground-floor unit with...
WHALER1257 1BR2BA, King and Wall Bed, Kitchen, W/D, SLEEPS 4, Great Ocean Views
We do not advertise on Craig's List, so please don't respond to any Craig's List listing for this condo. We don't want a crook to swindle you!Ocean View #1257, located high up on the 12th floor of the Whaler, offers amazing vistas of the Pacific Ocean, Kaanapali Beach,...
Maui Beach Front Condo Walking Distance to Beaches and Restaurants, ocean views
Newly remodeled spacious 1180 sq feet 2 bedroom, 2 bathroom condo with vaulted ceilings. Located within easy walking distance to shops, restaurants, and the best beaches on Maui. This unit is perfect for singles, couples, or families!This is not just an investment...
Fabulous, Ocean & Golf Course Views! Air Conditioning in Both Bedrooms
This beautiful, spacious condo is in a quiet location next to the Makai Golf Course and close to two other golf courses, within walking distance from the 1 Hotel Hanalei Bay, beaches and snorkeling sites, and near the Princeville Golf Clubhouse. It is almost 1500 square...
STUNNING BRAND NEW REMODEL-OCEAN VIEWS-LARGE LANAI-AC-WELL EQUIPPED
Book with confidence, this stunning brand new remodeled 1 bedroom, 2 bathroom (818 sq ft.) condo at Kamaole Sands. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and...
Steps from the pool and across the beach! Maui Vista 1118
Soak in the sun and unwind at this stunning condo in the heart of South Kihei. Located on the bottom floor in the first building and only steps away from the pool. We are a short walking distance from the famous Charley Young Beach, and close to fantastic restaurants,...