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.
Serene home with enclosed nature walk, meditation spot, & gardens
E Komo Mai Retreat Ohana | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Channel your yogi self and experience the serenity and spirituality of the EKomoMai Retreat....
Holua Moana Hale: Spectacular Oceanfront Home with Private Pool & Spa
Nestled within the private, gated community of Holua Kai in Kailua Kona, Holua Moana Hale offers a seamless blend of modern comfort and barefoot island luxury. Overlooking the rolling greens of Kona Country Club and the endless Pacific beyond, this two-story residence...
Breathtaking Oceanfront Suite @ Kalapaki Bay
Luxury oceanfront suite in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this suite is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate indoor-outdoor...
Malia Kai #12 condo in Kailua-Kona Town!
Three story townhome corner unit located in Malia Kai condominiums w/private carport walking distance from just about anywhere in Kona! Share our private retreat and where you can work from Paradise with laptop workstation featuring a high end 32” screen and the...
Kona Bali Kai 307 Oceanfront– 2BR/2BA Condo with Panoramic Views
Absolutely Oceanfront!Vast sea views await from this 2 bed/2 bath condo at Kona Bali Kai. Enjoy the sounds of the surf and year-round sunsets from the large, private lanai. In season, you might even spot turtles, dolphins, and whales passing by. This third-floor unit is...
Walk to Dtwn Hilo: Island Escape w/ Pool!
5 Blocks to Bayfront & Beach | 1 Mi to Rainbow FallsPack up for paradise, where relaxation and adventure blend seamlessly. This 2-bedroom, 1-bath Hilo vacation rental places you within just 1 mile of hot spots like the lively Hilo Farmers Market and the breathtaking...
Ka'anapali Maui Westin 2bedlockoff Oceanview Villa
Steps from beach, on site pools,restaurant and bars. Beach boardwalk access to all of strip including 5 star shopping and eating at Whaler's Village. World Class snorkelling 5 minutes away on foot at Black Rock. Unit is a 2 bedroom Lock off composed of one-bedroom...
NEWLY REMODELED-QUIET LOCATION-AC-WELL EQUIPPED-METICULOUS CLEANING
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that was just completely remodeled with all new furnishings. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of...
Gorgeous Private Home with Pool and Spa in Waikoloa Resort, Big Island
Our commitment to you, our guests, is to provide a high level of satisfaction through attention to details, high quality amenities and outstanding customer service. Please read on to discover what a special place our Ainamalu home truly is.DISCLAIMER** Please keep in...
Luxurious golf villa with updated appliances
Welcome to Kapalua Golf Villa 20V1, a luxurious 1-bedroom, 1.5-bath condo that can accommodate 4 guests and is located in the prestigious Kapalua resort, offering the perfect blend of elegance, comfort, and breathtaking natural beauty. As you enter the villa, you'll be...
7 Mi to Volcanoes NP: Serene Cottage w/ Deck!
8 Mi to Volcano Golf Course | Picturesque ViewsNamed ‘Halakea Hale (Pineapple House),' this peaceful 2-bedroom, 1-bath cottage combines traditional charm with modern comforts. Sip coffee on the deck as you marvel at the natural beauty of one of the few remaining...
Island Breeze Oasis - Newly Furnished
Welcome to our slice of paradise! Prepare for a vacation that feels like a dream – our villa is not just a place to stay; it's an experience waiting to unfold!Imagine waking up to the sun-kissed charm of four stunning lagoons right at your doorstep. These...
April SALE-9,10,14,15 SALE 159-TreeHouse Vibe AC-WiFi-BBQ-W&D-Cliffs-Sleeps 6
(Please Note we do not rent longer than 7 days)Casa by the Sea Welcomes you.Relax in Paradise with 1 acre of Tropical Jungle to explore and the sounds of the Ocean,Birds & Frogs. 5 Min short walk to Paradise Cliffs & Parks. COME SEE THE ONLY HAWAIIAN ISLAND WITH AN...
Spectacular Lakeside, Bali Hai Mountain View, Fairway Home
Welcome to Hale Mahina! Long hidden as a luxury private residence, this Princeville pearl is now yours to enjoy. All one level, Hale Mahina offers unobstructed expansive views of the bejeweled Nanolokama Mountains and Bali Hai across Lake Mahina and the world renowned...
Doesn't get better than this! A201
A LITTLE ABOUT THIS CONDO...Lokelani A201 is a 1130 sq. ft., 2 Bedrooms (A/C), 2 Bathrooms (sleeps 4), corner unit. Unobstructed panoramic ocean views, 30 feet from the private sandy beach with surf break. Boogie boarding, paddle boarding, surfing, snorkeling right out...
Maui's Best - Wailea Ekahi 47A
Aloha and mahalo for your interest in our spot in Paradise. Ekahi says it all. This one bedroom (with comfortable sleeper sofa), two-bath renovated unit is on the ground floor. This means the lanai is much larger than upper units. It also means that when you step off...
Kauai Bay House, Ocean Front, AC
KAUAI BAY HOUSE AT KOLOA KAI VACATION RENTALSOceanfront Luxury Overlooking Kukuiula BayWelcome to Kauai Bay House, a stunning two-bedroom, two-bathroom retreat perched above Kukuiula Bay on Kauai’s sunny South Shore. Offering breathtaking ocean and mountain views from...
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...
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
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...
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...
BIG ISLAND PLUMERIA COTTAGE New AC! Ideal Couples Getaway in Magical Puako!
Plumeria Cottage offers a vacation of ease indoors and out. Compact yet perfectly proportioned in the vintage beach style, it is a delightful combination of convenience and charm. And, with a roomy, sunny lanai and large shaded grassy yard, it becomes quite spacious. An...
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...
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! This new and spacious 1 bedroom studio (sleeps 2) is located within a new luxury home subdivision called "Ainamalu" in Waikoloa Beach Resort. The studio is...
🏖️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...
Kaanapali Alii | 234
Welcome to Kaanapali Alii 234, your ideal luxury vacation rental nestled in the heart of Lahaina, HI. This one-bedroom, three-bath residence offers an exquisite garden view and a private lanai with peekaboo ocean views, making it a perfect short-term rental for families...
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 – 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 2nd-floor ocean views within the resort, overlooking...
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,...
Spectacular Oceanfront View at Hanalei Bay Resort 9101,2,3
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!
Situated 7 miles north of Lahaina,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,...
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...