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.
Penthouse Oceanfront Renovated Condo - PH28. 180 Degree Direct Ocean Views!
Welcome to Sugar Beach Resort Penthouse 28. Our condo was completely remodeled in September, 2019 including a new kitchen and bathroom, new flooring, and newly smooth textured and painted walls throughout. We installed new cabinets, new quartz countertops, new stainless...
Completely remodeled! Walk to the beach! King bed!
This super clean property has an enviable upper floor location in a quiet building across from Kamaole Beach Park 1, one of the best swimming beaches in Hawaii! It features a bright floorplan and is completely equipped with new air-conditioning in the living room and...
Secluded ~ Centrally Located ~ Huge Lanai ~ Onsite Owner
A private studio cottage situated at the back of a one acre property. Surrounded by thick vegetation, you feel like you're in the jungle! Vaulted wood ceilings with exposed beams and optional dim mood lighting are two wonderful features.Garden views surround from the...
Kapalua Golf Villa #16 P1&2 - Upgraded - Fantastic Summer and Fall Deals
Kapalua Golf Villa #16 P 1 & 2 This pristine ground floor two bedroom, two bathroom air-conditioned Golf Villa is in a perfect location within the Kapalua Resort community. Great golf and ocean views are yours while you relax on the lanai over-looking the 10th fairway...
Spectacular! Full A/C Penthouse Level Ocean Front 1 Bedroom - # 608
Simply sublime!This fully air-conditioned penthouse level unit is sure to make your stay in Paradise a romantic and memorable one! Remodeled in 2016 and expertly finished by the best tradesmen, it boasts travertine marble flooring throughout, solid Oak wood kitchen...
Luxury by the Waves:Royal Mauian 218-Your Premium Oceanfront Sanctuary!-With A/C
Welcome to Royal Mauian #218, a beautifully remodeled condo offering exquisite details and modern amenities for your perfect Hawaiian getaway.Key Features: *Remodeled with Exquisite Detail: Enjoy a stylish and contemporary living space. *King Bed in Master Bedroom:...
Oceanfront, Second Floor, 2 Bedroom | 2 Bathroom with Incredible Oceanfront Views
Lanikai 122 – Luxury Oceanfront Living on Kauai's Coconut CoastWelcome to Lanikai 122, a serene second-floor oceanfront condo offering panoramic views of Wailua Bay and upscale island living. With two spacious bedrooms, each featuring king beds, ensuite baths, and air...
Kauhale Makai: 1 Bedroom with Ocean Views, Fully Remodeled and Redecorated
Aloha! Welcome to this beautifully renovated 1-bedroom condo, where you'll find all the comforts of home in the stunning paradise of Maui. Completely remodeled in 2021, this condo features a bathroom with a stylish tiled walk-in shower and all-new furnishings. Fresh...
2 BR/2 BA End Unit/all on 1 Level/2 Lanais/Prem Location/Awesome/Bld6-310
Maui is open and welcomes you with open arms. Welcome to our paradise home away from home. 6-310 Building 6 (3rd) Floor (10) Corner of bldg 😊🌺We have a gorgeous RARE 2 BEDRM 2 BATH all on one level, END UNIT in Building 6 on the 3rd floor overlooking the pool with...
Kahele Kai - Ocean views, steps to Poipu's best beaches, A/C throughout!
Kahele Kai, a three bedroom, three bath two story beach home close to Poipu Beach and Brennecke’s Beach. If you are looking for an outstanding vacation rental in Poipu Beach with newly installed, wall mounted Fujitsu A/C in both living areas and all bedrooms, Kahele...
Wailea Beach Villas | PH112
Awaken to the sweet sounds of palm trees swaying in the tropical breeze from Wailea Beach Villas PH112. Spanning 2,500 square feet, this main level, corner villa fuses a Hawaiian vibe with warm, earthy interior tones. The wraparound lanai offers peekaboo views of the...
Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry
Our open beamed 3 bedroom 2 bath home is surrounded by trees with windows full of light and airiness to let the trade winds blow. Conveniently near Haleakala highway, shopping, beaches, airport with a Maui country lifestyle. Sleeps six comfortably. Open kitchen, dining...
LAST MINUTE DEALS FOR MAY - PARTIAL OCEAN VIEW
Honua Kai is one of Maui's most luxurious five star resorts. Situated on North Kaanapali Beach, this oceanfront property is located just north of the Westin Kaanapali Villas and Nanea. If you are looking for quality accommodations on a beautiful sandy beach with a...
Oceanfront Private Home on Kahalu'u Bay with Pool
Private comfortable rustic bungalow home where your backyard is the ocean. Beautiful oceanfront setting where the waves splash against your lanai. The master bedroom located about 35 feet from the ocean. Relax in your own pool touched by ocean spray. Yellow tangs...
Spacious Koa Resort Condo, Across Street From Beach, Huge Pool
In this beautiful 1100SF 2nd floor 2BD/2BA condo all the amenities of a luxury home will be at your disposal. Extensively remodeled in 2015 with name brand appliances and new furniture this property features gorgeous native Hawaiian Koa wood vaulted ceilings, granite...
Hale Kamaole 326 Third floor condo, easy access to best beach on Maui!
Beautifully updated condo with partial Ocean View! Upstairs master bedroom has island style King bed and furniture. Remodeled master bath has walk-in tiled shower, new vanity and granite top. Downstairs bedroom has island style furniture with a Queen bed. Downstairs...
Kiahuna Lani at Poipu: Brand New Pool! Tropical Luxury on the Golf Course w/ A/C
Welcome to Kiahuna Lani at Poipu by Gather, a luxurious retreat nestled within the exclusive Wainani community on Kauai's sunny South Shore. This 3-bedroom, 3-bathroom home spans 1,942 square feet and boasts a new pool, creating a private oasis of comfort and elegance....
Relax In The Heart of Lana'i
The Jasmine House is a traditional Hawaiian style home built in 2000 by Castle and Cooke Ltd and upgraded in 2010. New Casper beds were purchased in 2018. Red mahogany floors run through the entire home. Both baths have tile flooring, granite counter tops, one has a tub...
Ohana House - a 3br/2ba home near the beach in Hanalei
TVNCU - 1336 TA#030-651-8528-01 - "The Family House"Ohana means family and this house is a great space to spend time with your family! Relax throughout this two bedrooms plus a loft, and two baths home. Recently updated with AC throughout the house, new furnishings and...
NEW LISTING: Stunning 3 Bedroom Sleeps 8! Incredible North Shore Views!
Welcome to Pretty Ville, Princeville’s Hidden GemNestled in one of Princeville’s most sought-after enclaves, the Liho Liho cul-de-sac, Pretty Ville is a timeless island home surrounded by lush, curated landscapes and sweeping views. This classic residence stands as...
One Bedroom Oceanfront Condo at Papakea Resort
This beautiful one bedroom oceanfront unit is located on the third floor of the 'A' Building at Papakea Resort and is approximately 50 feet from the ocean. Papakea is a beautifully landscaped, low rise complex (4-story) that includes 2 swimming pools, 12 gas operated...
Beach House on Spectacular North Shore Beach - Sunset/Ke Iki
LOCATION, LOCATION, LOCATION. This charming beachfront house is located on one of the largest and most beautiful beaches the North Shore of Oahu has to offer. Relax and enjoy the sun, surf and sand that is right under your toes. Whether you are ready to surf, snorkel,...
2 minute walk to beach/ AC / cul-de-sac
Welcome to Paradise! This lovely 3 bedroom 3 bath home is located directly between gorgeous Hanalei Bay (voted the best beach in America for 2009) and quaint Hanalei town, where you'll find a nice selection of shopping and dining. Hanalei is a quaint beach town with...
Modern Maui Condo perfect for your Island Getaway
Aloha & Welcome to Maui! Unwind at this stunning beachside condo located in the Kamaole Sands Resort. This ground floor unit is conveniently located close to all of the resort amenities including a large swimming pool and Jacuzzi, fitness center, tennis courts and more!...
Kamaole Beach Royale 506 - Stunning Ocean Views, Spectacular Renovation, AC
Experience effortless island living at Kamaole Beach Royale 506. This beautifully appointed one-bedroom, one-bathroom condo is perfectly designed for relaxation and comfort. Located on the 5th floor, this condo welcomes you with a serene atmosphere, highlighted by...
Kaanapali Shores 746 40%Off June Special for Summer Beach Fun w Pool & Hot Tub
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kaanapali Shores 746, a beautifully remodeled 1-bedroom, 1-bath retreat perched on the 7th floor of Kaanapali Shores Resort...
KJ’s Place, in the heart of the city.
KJ’s Place is a newly remodeled condo located in the heart of Kailua-Kona. The kitchen and living room open up to a covered lanai with view of the city and the ocean. Custom touches abound, from the granite countertops to the mahogany in the bathrooms to the grass...
Private Studio, 10 min walk to Hakalau Beach, Hamakau Coast. 15 min to Honoli'i
Private and separate from the main house, guest studio in lovely Hakalau village community. This is an adorable and private room at the back of our detached garage. Easy access and parking, comfortable queen bed, desk space, private bath, spacious shower, HD Smart TV,...
❤️PiH❤️ SWEET HEAVEN ★New Home★ We♥Big Families ★Pamper yourself in Luxury★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest home in our Hawaiian Luxury Collection. Sweet Heaven Villa at KaMilo is a wonderful 4 bedroom home.We pride ourselves on providing some of the most sought after homes on the Kohala Coast and are...
Robertson's Beach House
The four bedroom home is built in the classic Hawaiian mauka - makai (mountain - ocean) fashion. It is one room wide with 10 foot high ceilings designed to capture the sea breeze during the day and the mountain air at night. The shady indoor and outdoor lanais provide...
Poipu Ohana Hale! Beautifully Updated Single Family Home with Enough Space for the Entire Family.
Enjoy your weekend vacation in this large air-conditioned home located only a few blocks from beautiful Poipu Beach. Plenty of room for the whole family with 2 Bedrooms, 2 Bathrooms and a large bonus room that is used as the third bedroom. The main bedroom has a nice...
If You Deserve the Best...... This is it! Oceanfront Condominium For You!!
For those in the know, Lae Nani is the premier property on the coconut coast. Within Lae Nani, this unit offers the ultimate in vacation luxury. This one bedroom, bath and one half unit, features an unparalleled ocean view and a luxurious contemporary style. From your...
Makani Sands #202 1brm Beachfront condo with balcony on the ocean
Enjoy beautiful sunsets, magnificent views of the islands of Lanai and Molokai, turtles off the reef and whales in the winter season from the lanai of this 2nd floor one bedroom fully updated Maui Rental Condo. Unit 202 includes fully equipped kitchen, with granite...
🏖️Gorgeous Ocean Front | Gated Community | Walk to Town | vrKCV
vrKCV - Kona Bay Estates Hale Kai Olu, Professionally Managed by Kona Coast VacationsWelcome to Hale Kai Olu – Your Private Oceanfront RetreatHome away from home. Peace. Tranquility. Beauty. Photos won't do this home justice. Hale Kai Olu is everything you dream of...
HK K1024 Renovated Honua Kai Condo with Stunning Views Beach Pool AC
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...
Gorgeous Remodeled Ground Floor Unit w/ New Central Air Conditioning / 1 Bedroom
Aloha! Welcome to our Kamaole Sands condo, a 2 minute walk to Kamaole III Beach. Our condo, with large lanai, is a private and beautifully remodeled ground floor unit with a peekaboo ocean view from the lanai. Our on-island contact/concierge Darrel Smith will contact...
New Listing, Wailea Ekahi Village 5F, Close to Oceanfront Pool Pavilion on Keawakapu Beach
Prime Location & Ocean Vistas: Escape to Maui's paradise at Wailea Ekahi Village unit 5F. This charming 2-bedroom, 2-bathroom condo boasts a prime location near the beachfront pool, pavilion, and Wailea Beach Walk. Relax on the second-floor lanai and soak in the ocean...
Deluxe Ocean View Ground Floor.... Renovated ..Walk to the Hyatt and Beach...A/C
This is a RENOVATED deluxe GROUND FLOOR unit at Poipu Sands, in the Poipu Kai Resort. It has a wide white water OCEAN VIEW down to Shipwreck Beach, where the Grand Hyatt Kauai is located. This unit faces into the trade winds, providing a cooling breeze, even on the...
A"nuenue Lanai, "The Rainbow Lanai"!
Steps to the World famous "Makai Golf course!" This Plantation at Princeville 3 BR, 3 full bath condo includes new stainless steel appliances, A/C, large covered lanai with a large teak table and extra seating. Experience fantastic sunsets, rainbows, mountains views,...
KBM Resorts| Honua Kai Luana HKL-12A, Ground Floor Private Outdoor Kitchen, Includes Rental Car!
Luxurious 3-bedroom Luana Garden Villa with over 2,000 sq. ft. of indoor-outdoor living, private lanai, outdoor kitchen, gourmet appliances, spa-like bathrooms, and elegant island-inspired dcor.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
Waimea Point Oceanfront House - with Air Conditioning
Our beautifully remodeled ocean front house, located at Waimea Bay on the world famous North Shore of Oahu, has Hawaiian views you dream about. The cozy house sits perched on the ocean's edge, with the ocean literally just a stone's throw below. We have solar powered...
Perfect Island Getaway - Maui Vista 3307
This well maintained one-bedroom, one-bath condo offers peaceful privacy and gorgeous garden views from your private lanai. Located on the third floor of Building 3 with elevator access, it’s just a short 5-minute walk to the white sands of Charlie Young Beach and...
So Close To Ocean, fabulous views, extended stay up to 6 weeks starting Feb. 26
Free use of owners car for reservations ask for details. (Escalade) see car in picture section.Private Host.. Check in 3pm check out 11am, When you rent a room from a private condo owner, you get the room that you see in the photos, along with the location you choose ,...
Incredible & Spacious Oceanfront Condo 🏝️ Walking Distance to Beach and Town!🩴 Kona Reef D-8
Kona Reef D-8 is a large 2-bedroom panoramic floor to ceiling oceanfront ground floor condo with breathtaking year-round golden sunset views from the lanai! Hear the waves crashing day and night! This recently upgraded, spacious 1000+ sf condo has all the comforts of...
Sun-Soaked Waikoloa Retreat w/ Private Lanai!
Sandy beaches, amazing waves, and ocean views all await you when you book this amazing condo in Waikoloa! Head to the community's oceanfront club, complete with a private pool, restaurant, and bar, then go to one of the nearby beaches. Venture out and swim with dolphins...
New! 🩴 Your Dream Vacation Condo @ Holualoa Bay Villas 🐬 Corner Unit 2 BD/2BA
You just found Your Dream Vacation Condo @ Holualoa Bay Villas on the famous Ali'i Drive! Just listed with new Owner in mid May 2022. 2 Bedroom, 2 Bath Corner Unit with Fantastic Ocean Views of the Beach Right Across the Street! Welcoming Wrap-Around Lanai, Dining...
Kona Pacific Top Floor Retreat: Ocean View & Pool!
Say aloha to this exquisite 1-bedroom, 2-bathroom Kailua-Kona vacation rental condo nestled in the scenic Kona Pacific complex! Featuring A/C, updated amenities, and a fully-equipped kitchen with a Burr grinder for your Kona coffee, this inviting Hawaii residence has...
OCEAN VIEW STUNNER, SNORKEL w/ TURTLES, PRIVATE COVE
EPIC OCEAN VIEWS, close to restaurants and dining, family-friendly activities, public transport, and nightlife. You’ll love our place because of the neighborhood, comfy bed, coziness, views and the kitchen. Our home is good for couples or families.“Honokeana Cove...
REMODELED-WELL EQUIPPED-CLOSE TO THE BEACH-AC-METICULOUS CLEANING
Book with confidence this brand new remodeled, lockoff 2 bedroom condo, that provides a great vacation experience. This 2 bedroom unit offers tremendous value with it's beautiful modern, new finishes, proximity to the beach, and how well it is equipped. Kamaole Beach 2...
Pikake - West Maui Beachfront Condo! 20 Feet from the Ocean!
This West Maui beach condo is located on the ground floor of a 2 story building with only 12 units in the quiet area of Honokowai. At ground level a mere 20 feet from the sea shore with a wide ocean view presenting the islands of Lana'i and Molokai and spectacular...