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.
Available and legal for stays less than 30 days.
Hawaii Sheffield House has been a legal bed and breakfast for over 35 years. We are available and legal for stays of less than 30 days. We provide a unique neighborhood stay in Kailua Hawaii that is just down the street from Kailua Beach.The Hawaii Sheffield House...
Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach
Treat yourself to ultimate island luxury in this architecturally designed $5.5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK...
Paradise Found! Top Floor, Beachfront, Oceanfront, Ocean View
Welcome to Paradise Found! Memories are made here!Come, relax, unwind, and enjoy the unforgettable breathtaking, panoramic ocean views from EVERY room in our beautiful top floor direct oceanfront, beachfront Kealia Resort Condominium nestled RIGHT ON Sugar Beach, just...
Beachfront 6 Bedrooms with Pool
Legal Vacation Rental: Permit Number STKM2020/0002HOLIDAY SEASON: There is a 7 night minimum during the period Dec 18-27. There is a 10 night minimum during the period Dec 27-Jan 10.Chill Out with friends or family in this spacious two-story Maui beach house which...
Stunning Two bedroon Corner Oceanview condo in Kihei
D301 is a uniquely located corner unit 2 bedroom, 2 bath full ocean view condo with AC. This condo is on the third floor so you are walking up stairs.Watch surfers, windsurfers, and kite boarders as well as Humpback Whales during the Whale season. Wake up to stunning...
Partial Ocean View 2 Double Beds at Outrigger Kona Resort and Spa
Your adventure to the Kona Coast starts at this oceanfront Big Island property, just steps away from the sun, sand, and surf. Guests will enjoy spectacular dining options, including a waterfront restaurant and poolside bar. The on-site spa and fitness center offer a...
Maui Resort Rentals: Polo Beach Club 608 – Luxurious 6th-Floor Oceanfront 2BR w/ Stunning Ocean Views!
We are proud to present this luxurious 2BR/2BA oceanfront residence at Polo Beach Club–newly launched on 10/25/24 to start taking reservations for check-ins on 1/6/25!Boasting a stunning Wailea oceanfront location and a lavish interior, this 2BR/2BA residence delivers...
Luxury 800 ft" 1 bedroom Suite, Full Large Kitchen, King size bed, Free Laundry
Built in 2022!This large luxury1-bedroom suite, the main part of the 4 beds, 3 baths single family house with its own private entrance, is located on a one-acre land harboring the most unique feature of Hawaii Paradise Park in Keaau and offers a real retreat from the...
Hanalei Bay Villas #36 - Ocean and Mountain View Condo
Hanalei Bay Villas #36 is a spacious three bedroom, two and a half bath, two story stand-alone condominium. Beach access is available past the newly renovated 1 Hotel Hanalei Bay next door. Views include the Hanalei Mountains and the open ocean. You enter the villa on...
Oceanfront Sugar Beach 525 Tropical Condo, on the Beach,
SOUTHWEST SUNSETS-Sitting on the lanai, you are facing beautiful southwest sunsets, view is the website pictureWHALES January through April breaching in your view, all the comforts of home in a warm, tropical location with our building 20 feet from the ocean. BEACH is...
Beachfront Platinum Condo, updated. Gorgeous Ocean & Crater Views. Makena Surf.
Building B is the premier beachfront building at Makena Surf, set among lush tropical gardens. From our condo (B202), gaze endlessly at the ocean, watch the whales breach (seasonal), experience magical sun sets, step onto the beach to swim or snorkel with the turtles or...
ILIKAI NEWLY RENOVATED OCEAN VIEW ONE FREE PARKING
Newly renovated stunning condo unit at the Ilikai hotel is fully equipped with everything you will need for the perfect stay. All new appliances, furniture, flat screen TV's, leather pull out sofa, modern design, bidets, AC, Xbox, Wifi and more. 2 bedrooms, 2 full...
Kaanapali Alii | 246
Kaanapali Alii 246 was designed for entertaining! As a corner unit, most of the living room and dining room are highlighted with wrap-around windows which offer constant views of the beautiful Maui landscape. The open floor plan seamlessly combines the kitchen, dining...
Wailea Ekahi Village | 3E
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo offers elevated views over the tropical grounds lush with colorful island landscaping.The vaulted ceilings and oversized...
Top Floor 1 BR Ocean, Kaanapali Golf Front A206 Maui Eldorado
E Komo Mai “welcome” to Maui Eldorado A206! This modern condo is located in the heart of Kaanapali, one of the world's most well-known destination resorts with spectacular ocean, Molokai and western exposure towards the island of Lanai. When relaxing in the spacious...
Kahala Breeze: Modern Tropical Home with Pool & Private Yard
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.Experience the laidback luxury and authentic...
Ko Olina Beach Vacation Home
Luxurious three bedroom Ko Olina Resort villa located in west Oahu. Enjoy the calm ocean lagoons. In short walking distance to Four Seasons, Marriott Beach Club, Ko Olina Golf and Ko Olina center (restaurants & shops).State of Hawaii requires us to collect 17.75% tax on...
Stunning Oceanview 1 level 2B w Split AC at Kamaole Sands!
Welcome to our newly renovated beautiful seaside single-story 2 bd 2 ba condo at the highly rated Kamaole Sands, located yards away from the stunning Kamaole III beach, Maui's famed "postcard beach" that is fantastic for snorkeling, swimming and boogie boarding and more...
Free Parking 1BR Waikiki Banyan Partial DH Views with AC
Nice and Exclusive 1 Bedroom/ 1 Bathroom / 1 FREE PARKING (max 6') at the Waikiki Banyan with No better location to enjoy Waikiki’s entertainment, a quick stroll from the beautiful and sandy beach, and great partial views of the Diamond Head! Sleeps up to 4 guests...
Bright & Airy Princeville Home with High-Speed WiFi, Private W/D, & Gas Grill
Enjoy a relaxing Kauai vacation in this open and airy Princeville home. With sky-high ceilings, exposed beams, and plenty of natural light, you'll feel right at home. The kitchen features full-size appliances, perfect for preparing meals, and the wraparound lanai offers...
Alihi Lani 5 - Oceanfront - Sunset Views - A/C
ALIHI LANI. This small, 6 unit complex is a 'Real Gem', according to the Ultimate Kauai Guidebook. Enjoy endless views from our oceanfront pool. The front landscaped area also has two gas grills and comfy lawn furniture.OCEANFRONT. Our premium second floor location has...
Luxurious Oceanfront Escape Awaits – Stunning Views & Top-Floor Waikoloa Living!
Aloha and welcome to the idyllic gated community of Hali'i Kai! We're thrilled to introduce you to our exquisite, 180-degree oceanfront condo, where luxury meets affordability, and offers all the indulges, beauty, and relaxation that the Big Island has to offer....
Kona Acres Vacation Home
This vacation home is your destination if you desire privacy, have a family or want a laid-back vacation. This luxury home is ideal for large family gatherings. The house is located on a secluded one-acre, tropically landscaped lot in a quiet, quality Hawaii...
Private Kōloa Retreat | Pool + Golf Course Views | Near Poʻipū Beach
Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for a relaxing island retreat. With three full bathrooms including walk-in showers, a soaking tub in the master suite, and...
Modern & Polished Oceanfront Vistas
Summary:Bright, modern, and spacious. Complete remodel in December 2021! Thoughtfully designed to elevate your experience with us. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in the sunny and...
Makai Estate – Hualalai Luxury Villa with Saltwater Pool
WHY IT'S SPECIALPicturesque, bedroom island suites with outdoor garden showers, premiere resort location, impressive indoor and outdoor chef's kitchen, and oceanside views from the sprawling lanai.Completely relish in the elevated Big Island lifestyle in this...
REMODELED Tropical Paradise 1BR unit in Princeville with AC & assigned parking!
Beautiful TOTALLY REMODELED 1 br/1 ba unit with living room, full kitchen washer/dryer and spacious lanai in heart of Princeville. Kitchen and living room completed already, bedroom, and bathroom in process. More updated photos coming soon!ASSIGNED PARKING SPACE!Great...
Kamaole Sands 7-405 - Stunning Renovation, Large Lanai, Ocean Views, Split AC!
Welcome to Kamaole Sands 7-405, your luxurious tropical escape in the heart of South Kihei, Maui! This stunning top-floor 2-bedroom, 2-bathroom condo is the ultimate destination for an unforgettable island getaway. With breathtaking views of the lush tropical courtyard...
Amazing Views, Walking Distance to Beaches - Kapalua Bay Villa #14B1 - Quam Properties
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! Quam Properties 14B1 is a one-bedroom condo featuring amenities such as picturesque ocean views, vibrant tropical decor, and complimentary high-speed wireless internet. The condo can...
NEW! Beachfront, Amazing Views, AC, Hear the Ocean, Beautiful Spacious Remodel
**NEW - Captain Jack's Island Grill Restaurant just opened January 2025!!! So convenient to grab a bite to eat! Pool side and oceanfront!!!** Welcome to our oceanfront condo, Beachfront in Maui! Whether you are planning a romantic getaway for two or a family vacation,...
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!
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 the entire ocean-facing...
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
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 and bedroom. Golf Villa #25V1 has ocean views that await you from the spacious...
Bamboo Waikiki #210. Spacious studio located in a tropical oasis.
Bamboo Waikiki #210. Studio condo with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) King bed, (1) Queen sofa sleeper, (1) Twin sofa sleeper; Sleeps 5.Spacious studio located in a tropical oasis in the heart of Waikiki. Bright open space...
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...
Ko Olina Beach Villas B506 by Gather: Luxury 2BD 2BTH w/ Ocean Views
Discover the charm of island living at Ko Olina Beach Villas B506 by Gather, a magnificent beach villa in the heart of the renowned Ko Olina Resort. This exquisite two-bedroom, two-bathroom villa on the fifth floor, with space for up to six guests, offers a luxurious...
Comfortable Hawaiian Style Home
This cozy and comfortable Hawaiian style redwood home is just a short walk to miles of sandy beach. The house is surrounded by lush, tropical gardens. Two lanais let you enjoy paradise in comfort and privacy. A wonderful place to get away and relax in quiet and comfort....