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.
Napili Shores G258 Oceanview-King Studio-Currently being renovated
Gorgeous Ocean View Second Floor Studio at Napili Shores!Right on popular Napili Bay Beach!Two immaculate swimming pools - one ocean front and the other a garden viewBrand new furnishings!Famous Gazebo restaurant on property!Newly Remodeled!! Air-conditioned , Second...
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
Welcome to our home, Sugar Beach 311. This is a non-smoking, professionally cleaned, recently renovated and updated one bedroom condo. It is an immaculately maintained and spacious one bedroom, third floor corner unit, with front and side views of the ocean and beach...
Enchanting Rainforest Hideaway, on 2 Private Acres to yourself. Pahoa/Keaau
The Enchanting Rainforest Hideaway is a custom vacation home which stands alone on 2 private acres surrounded by a lush rainforest which gives you the experience of old Hawaiian style simple elegance. Beautiful custom vacation home on 2 private acres in a rainforest...
New Listing! Beautifully remodeled!
The Kona Makai complex is right on the beautiful Kona coast! Kona Makai provides an ocean-side swimming pool, hot tub, minimal fitness center, ping-pong table, cabana, gas bbq areas, tennis courts, and complimentary parking. Kona Makai also has direct access to the...
Cozy jungle boat hideaway with stunning ocean view TA-154-746-2656-01
The Jungle Queen is a perfect getaway for 2 or a rejuvenating hideaway for the independent traveler. You’re staying on a landlocked boat in the middle of a jungle with coqui frogs singing you to sleep each night. Relax on the deck and treat yourself to ocean views just...
14 Beds / 9 Bath / Central AC / Luxuriously Spacious / Accommodates 28!
NEW LISTING! 3 Separate Condos in the same building - On the 2nd & 3rd floor of a 3 story building. 1-5 Bedroom (3 Kings, 3 Queens) 3 Bath Sleeps 12 Adults2-4 King Bedrooms 3 Bath each sleep 8 Adults. BEST VILLAS AT THE REGENCY! A cut above the rest. Finest furnishings...
Hilo's most secluded luxurious ocean front estate
Hale Hokulea - Private Oceanfront Estate on 16 Acres Welcome to one of Hawaii’s most secluded luxurious ocean front estates!Our family vacation home is situated on a 16-acre heart of palm plantation along the Scenic Route. As you enter the gated estate, you will feel...
Pililani - Upcountry Maui Private Resort on 4 Acres with Fruit Trees, Pool, Tennis, Hot Tub & Sauna
Maui County Rental permit - STPH 2013/0016TA-112-940-0320-01 / GE-112-940-0320-01TMK-270121170000Pililani means "close to heaven", which is an appropriate expression for this property. The magic of this land clearly speaks for itself, let alone the fabulous house and...
Charming, Romantic Beach Cottage at Anini Beach! TVNC 1361
Tucked beneath swaying palms and just steps from the gentle turquoise waters of Anini Beach, this enchanting one-bedroom cottage is pure island charm. With its vintage flair and dreamy, movie-set vibes, it’s the perfect hideaway for romantic retreats, solo escapes, or...
Very Best Deluxe Ocean View...Panoramic View....First Class!!
My wife and I are proud to offer the very best Deluxe Ocean View villa in all of Ho'olei for your vacation. Only the top row buildings (A-F) are classified by the Grand Wailea as Deluxe Ocean View. Our Unit is in the 'A' Building. Building 'A' sits the highest of all...
Laule‘a #14 by Gather – Mauna Lani Villa w/ Golf & Mountain Views & Private Pool
Welcome to Laule‘a at the Mauna Lani Resort #14, a 4-bedroom, 4.5-bath luxury villa on Hawaii’s Kohala Coast where golf course views and Mauna Kea’s sweeping silhouette frame your private escape. With a pool and spa surrounded by tropical landscaping, spacious...
New Modern Studio in Waikoloa Beach Resort- Close to White sand Beaches!
Perfectly located in Waikoloa Beach Resort - Big Island! Close to all the best beaches on the Kohala Coast! Away from crowds...very serene and quiet.This new and spacious 1 bedroom studio (sleeps 2) is located within a new luxury home subdivision called "Ainamalu" in...
🏖️Sophisticated Oceanfront Retreat | Air-Conditioned | Walk to Beach | vrKCV
vrKCV - The Kona Hideaway at Kona Onenalo No. 11, Professionally Managed by Kona Coast VacationsThe Kona HideawayDiscover the essence of Hawaiian living at The Kona Hideaway, a private oceanfront villa nestled in the exclusive gated community of Kona Onenalo. Adjacent...
Island Glow Kailua Village, AC and ocean views in the heart of Kailua Kona
See whales, dolphins, Ironman Village and Ali’i drive from your very own lanai! Island Glow in Kailua Village is a beautifully remodeled 1 bed 1 bath condo with a brand new king bed and queen pullout sofa bed in the heart of historic Kailua Village. You will enjoy ocean...
Kaimana Surf Luxe by Gather: Beachfront 1BR w/ A/C, Views & Dining
Welcome to Kaimana Surf Luxe by Gather, a modern oceanfront one-bedroom condo perched above the golden sands of Kaimana Beach in Honolulu. Designed for up to five guests, this sophisticated retreat combines sleek design, panoramic ocean views, and direct beach access...
Kaanapali Alii | 234
Kaanapali Alii 2342 Bedrooms | 2 Bathrooms | Sleeps 6 | Garden View________________________________________Welcome to Kaanapali Alii 234, a beautifully renovated one-bedroom garden view condo with a fully enclosed den that comfortably serves as a second bedroom. Relax...
Ocean Front Sunset & Whale-Watching Views at Hyatt Vacation Club
The Hyatt Vacation Club is a new luxury ocean front resort on the south end of Kaanapali Beach, combining the best features of a luxury hotel and a deluxe condominium. This ocean front villa features floor-to-ceiling sliding glass doors opening from the living area and...
180 Oceanfront View! A/C, Remodeled, 2 Oceanside Pools, Great Location, Clean!
We are a LEGAL Short Term Rental. If STRs are banned, we will refund your reservation money.We are 6 miles north of the fire. Our beaches, sunsets & ocean are still amazing. Remodeled Large Studio with New AC. Sleep 30 feet from the ocean to the sound of waves!...
The ‘IMI OLA at Kiahuna Beach - Great Location on Kauai's South Shore -A/C
Aloha! E komo mai to our little slice of paradise. Located in the community of Kiahuna Plantation Resort in Poipu, Kauai in Unit 127. Our first-story walk out unit sits on a 35-acre beachfront resort with large rolling lawns, well maintained gardens, and a path that...
Maui Condo Steps from the Beach--Mountain Views and Partial Ocean View
Lodging is an important part of the perfect Maui vacation. Being in a great location, not only on the island, but also on the property itself, is key. It should be updated, clean, well-equipped, and the beds have to be comfortable. Just steps from the sand, this condo...
Stunning Ocean View Penthouse Unit! Quam Properties Hawaii
Kaanapali Shores 905 one-bedroom penthouse featuring amenities such as a magnificent ocean view, comfortable seating area, and a private lanai. The condo can accommodate up to 4 guests with a king-size bed in the bedroom a queen sleeper sofa and a twin sleeper sofa in...
Perfect South Maui Ocean View Condo
Just posted new lower summer rate for my wonderful Kihei Akahi, 1 bedroom / 1 bath, ocean view condo. It is clean and quiet with an ocean view from the lanai. Remodeled and professionally decorated in a Hawaiian style with artwork from local artists, you'll find...
Kona Beach Estate: Oceanfront Home with Pool & Private Beach
This luxury oceanfront vacation rental in Kailua Kona promises an unforgettable experience, blending unparalleled comfort with the natural beauty and vibrant culture of the islands. It's a place where every moment is infused with the spirit of aloha, creating memories...
Kolea 10B ~ The Heart of Kolea with Unforgettable Ocean Views
Welcome to Kolea 10B – $100 Lava Lava Beach Gift Card Emailed to you on Arrival!Location, View, Perfection… Stay at one of the most desirable vacation rentals in Waikoloa Beach Resort with breathtaking ocean views on the Kohala Coast. Kolea 10B offers one of the best...
Upgraded ground floor condo with beach access
E Komo Mai “welcome” to Hale Mahina B105! Hale Mahina B105 is a ground floor, one bedroom, one-bathroom condo that sleeps 4 guests. Although this unit does not offer air conditioning, stay cool inside with ceiling fans throughout! The entire unit boasts new, beautiful...
Spectacular Oceanfront View at Hanalei Bay Resort 9101,2,3 - 6 min walk to beach
One of two full oceanfront views of Hanalei Bay with private lanais and grass lawn looking over the breathtaking views of Hanalei Bay and Bali Hai. Enjoy an amazing sunrise breakfast and cup of coffee as you overlook the bay as the sun wakes up the sparkling Pacific...
Luxurious 2.5 Bedroom Unit with Panoramic Ocean View in ONE Ala Moana
This luxury unit has an epic panorama ocean view with floor-to-ceiling windows. ONE Ala Moana is the pinnacle of world-class living. This unit has 2 bedrooms plus a den, 2.5 baths, and 1 parking. One Ala Moana has a long list of luxury amenities and a great service team...
Nihilani 34C - Beautiful Hawaiian Townhouse
Introducing Nihilani at Princeville 34C, now available through Makana Kauai Properties. Nihilani offers luxurious accommodations on the north shore of Kauai. These Princeville condos showcase a plantation-style architecture with multiple lanais, enclosed garages,...
"Pacific Paradise" - Lae Nani 425 - Upgraded Second Floor 2 Bedroom | 2 Bathroom-with A/C
NEW OWNER- Newly Renovated with Central AIR Oceanview, Second Floor, 2 Bedroom | 2 BathroomA beautiful newly remodeled two bedroom, two bathroom unit on the second floor of building four at Lae Nani, the premier condo property on Kauai's Coconut Coast (East side). This...
OHANA means FAMILY! Stay at the beautiful Ohana Beach Retreat in Keauhou!
Please read listing description for full details on this lovely property! We also have another listing at the Keauhou Surf and Racquet Club if this property isn't available: Vrbo 1620967. We are an approved Short Term Vacation Rental through the state of Hawaii. Ohana...
Kailani Estate: 5BR Luxury Home at Mauna Lani Resort
Brand new contemporary single-story luxury estate located in the exclusive One Ocean community at the Mauna Lani Resort. This expansive 5 bedroom, 5 bath home comfortably sleeps 10 guests and is ideal for a family vacation or as housing for a business group needing...
Unforgetable Sunsets and Panoramic Views From Your Private 10th Floor Lanai!
Panoramic views and beautiful sunsets from the lanai await you at this completely remodeled, fully air conditioned condo at Royal Kahana. The remodel included new window treatments, new appliances, new solid wood dark cherry cabinetry, and a tiled, walk-in shower, all...
Waikoloa Colony Villas Unit 2001 Garden 2BD 2BA
Waikoloa Colony Villas is located at 69-555 Waikoloa Beach Drive, Waikoloa, HI 96738 - Guests check in at Hawaii Vacation Condos by Outrigger’s office located at the Kings’ Shops, 69-250 Waikoloa Beach Drive, Suite B-13. Open daily from 9am-5pm. - Townhome with garden...
Steps to the Beach, Calming Ocean Sounds & Views, Amazing Sunsets, Remodeled
Beachfront living at its finest. This recently remodeled condo offers it all! Incredible oceanfront views, quiet complex, breathtaking sunsets, whale watching during the season, steps to the beach, great restaurants, grocery store, coffee shops and convenience stores...
A/C Jacuzzi ~BBQ ~Golf Course & Mountain Views
Indulge in island-inspired artwork and luxurious elegance that awaits the discerning traveler in this exquisite home. Air conditioning seamlessly envelops the entire residence, ensuring comfort throughout. Just steps away from Hanalei Bay Resort, where open-air dining...
Beautiful Ocean & Golf course views at this Kapalua Golf Villa, discounted 2024
Our Kapalua Golf Villa sits on the 4th hole of the Bay Course. You will be street level with just three steps down to the entry. Enjoy watching golfers while having your coffee or have happy hour with beautiful ocean view sunsets from our oversized lanai. You are...
Walk to the beach in this lush, serene house with a private garden oasis
Welcome to Hale Leilani (Heavenly Home). Our home is a stunning 3 bedroom Hawaiian style home with soaring ceilings and a lush tropical garden with trees all around for privacy, making it great for couples or families visiting the island.We love design and creating a...
New Owner Special! Ocean View in KoOlina, HI
Create magical memories at this unique & family-friendly home. Koolina is a resort community with easy access to fine dining, boutique shopping, entertainment and Nature. We are out of the congestion, traffic and crowds of downtown. We are on the drier side of the...
Maui Resort Rentals: Westin Ka'anapali Ocean Resort South Studio Islandview Villa
This island view luxury studio villa sleeps up to 4 with one king sized bed and one queen sized convertible sofa sleeper. It is located in the Westin Kaanapali Ocean Resort Villas South. The villa is equipped with a gourmet kitchenette with granite countertops, a two...
Oceanfront, Renovated & Accessible Downtown Kona - Beautiful Ocean Views! 1st Fl
Accessible and modern ground-floor, 2 bedroom/2 bath unit with spectacular ocean front views on a 200 sq ft lanai. Only one small step from a parking spot directly in front of your unit separates you from your Hawaii Island home (walk around to the right for step-less...
LUXURY 2-Bed Condo, Kitchen, Wi-Fi, Parking, W/D, AC, LEGAL Monthly Rental!
Allure Waikiki #804 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! Max Stay 3 Months. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...
Magic Sands Retreat: Remodeled Cottage,Walk to Beach, Incredible Location,AC!
The Magic Sands Retreat is a quaint 3 bedroom/2 bath cottage just around the corner from the famed Magic Sands Beach and the Ali'i Drive beach corridor. Just a 10 minute walk to the most popular beach in Kona! This upgraded home shows attention to detail with an artists...
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
The best location in Wailea! Quick 2-minute walk to Wailea beach, shops, restaurants & the stunningly scenic Wailea Beach Path. BOOKING CALENDAR/MINIMUM NIGHT STAY:Our calendar opens 1 year in advance. Please reach out if you want to inquire about specific dates prior...
Luxurious & Spacious Ocean Vistas
Summary:Beautifully remodeled in early 2023. This elegant 2-bedroom, 2-bath condo features upscale touches with magnificent ocean views. Located steps from Wailea, all of Maui is within reach. We offer a fully stocked kitchen for those who want to cook. Enjoy the...
Fabulous central location! Walk to restaurants, grocery store, and many beaches.
FABULOUS CENTRAL LOCATION! This condo is newly remodeled and is walking distance to the Kailua pier, beaches, restaurants and we are right next to a grocery store. This unit is located one block from the best coffee shop in town. This older Hawaii complex has a...
Delightful home with private W/D, desk workspace, & a great location
Aloha Valley Shores | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy relaxing in a cheerful home filled with light, close to attractions but still providing the...
Wailea Beach Villas PH402 - 2 Bedroom Ocean View Penthouse
Experience the very best in tropical island living from ocean view Wailea Beach Villas Penthouse 402. Revel in sweet sunsets and seasonal whale watching from your spacious, private lanai with scenic views of the Maui horizon, Molokini Crater and the island of...
Maui Resort Rentals: Honua Kai Konea 529 - 5th Floor 3BR w/ Ocean Views from Every Room!
This three-bedroom deluxe oceanview residence offers breathtaking views of the Pacific Ocean and neighboring island of Lanai from its prime 5th-floor vantage point.The residence affords a perfect opportunity to gather, reconnect, and celebrate. There is ample room to...
Cottage on Beachfront Estate property, central Hanalei Bay
This amazing and completely refurbished home is situated on a stunningly beautiful one-acre, gated OCEANFRONT estate property, right in the middle of magical Hanalei Bay. It is, in fact, one of the ONLY vacation rental cottages on beachfront property to be found...
Tropical haven, close to beaches and shopping
Paki Maui 414 is a 1-bedroom, 1-bathroom condo located on the fourth floor with wonderful garden views from your lanai and floor-to-ceiling sliding glass doors, bringing natural light into the condo. The condo does have a split air conditioning in the bedroom and living...