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.
Renowned villa with modern touches and golf views
Kapalua Golf Villa 16V2 is a unique, newly remodeled, 3-bedroom, 3-bathroom villa located on the third level and can accommodate up to 6 guests. The fully equipped kitchen is perfect for dining in with granite counters, an island with a stove top, and additional counter...
Waipouli Beach Resort Penthouse Exquisite Ocean & Pool View Condo!
Oceanview! Resort lifestyle at its best at Kauai’s Hidden Gem: Waipouli Beach Resort, Oceanview Penthouse with cathedral ceilings, located on the fourth floor and highest floor in a quiet setting overlooking the only fantasy pool on the island! One of the most...
Condo in downtown Kailua-Kona - walk to restauants, shops, the beach
Come meet Wally the Whale! He hangs in the large living room. Newly renovated condo at Kona Pacific - shops, restaurants and the beach all within walking distance. Elevators and carts to make it easy to check in and haul groceries to your unit. Underground, assigned...
Malia Makai - F - Honu - A/C, Ocean Views
MALIA MAKAI - F AT KOLOA KAI VACATION RENTALSHonuYour Modern Island Escape in PoipuWelcome to Malia Makai F – Honu, a newly renovated 2-bedroom, 1-bathroom cottage designed for relaxation and adventure in Poipu. From its vibrant island-inspired interiors to its prime...
2 Bedrooms Oceanfront
This premium oceanfront Two Bedroom, Two Bath condo is conveniently located on the ground level. Master Bedroom has a King Bed with a private bathroom. Second Bedroom has a queen bed; and the living room has a queen sofa bed for the extra guests. This unit is...
BEACHFRONT LEGAL BUDGET CONDO-VIEWS-FREE PKG/WIFI, POOL, HOT TUB, TENNIS/PICKLE7
AWESOME! 180º UNOBSTRUCTED OCEAN /SUNSET VIEWS! BEACHFRONT! LIGHT, BRIGHT, AIRY, AND SUPER CLEAN CONDO! LEGAL VACATION RENTAL. NO RESORT FEE. FREE PARKING IN GATED LOT FREE iNTERNET/WiFi This unit has not been remodeled as recently as our other condos, so it is...
Molokai Shores C134
This condo is located on beautiful Molokai. Enjoy the quiet setting of this condo located on the ground floor at the far eastern side of the complex unit C134. Many people that have stayed in this unit comment that its location on the grounds makes it the best for...
Largest One bedroom at Kuleana - Oceanfront Unit!! #105
When you arrive at our condo, you will know that you have reached paradise! Kuleana is a low-rise condominium complex built around serenity. As an OCEANFRONT property, this unit is on the oceanfront side. The property is located near Kahana, where you will find plenty...
Beautiful Private Cottage w/ AC in Sunny Poipu Beach Estates 5 Minutes to Beach!
This new, air-conditioned suite is in an exclusive neighborhood of Poipu, offering you the most rare and impressive accommodation the sunny South Shore has to offer. The rolling golf course greens that surround this property provide an open and airy feel. Enjoy the...
Perfect Home for your Hawaiian Vacation! HR
Have your dreamed of vacationing near Keauhou Bay? Now is your opportunity!! This charming 2 bedroom, 2 bath home is awaiting you! Keauhou Bay is known for its, beautiful, calm waters, it is ideal for families, snorkeling, kayaking, fishing, and stand up paddling. Our...
KRL C202 2BD Kaanapali Golf Course w Pool AC
Kaanapali Royal C202 Golf Course View from 2BD/2BA West Maui Condo Near The Beach 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...
100% Walk Score to Eat & Play Across from Kamaolé Beach. 2bd 2bd AC Kihei Condo
** ACROSS THE ROAD FROM KAMAOLE BEACH ** Catch the Peek-a-boo Ocean View from the LanaiStart your stay with all the amenities you need for a more affordable vacation!Conveniently located in the heart of Kihei where you can walk to dine, shop, surf, snorkel, boogie board...
Hawaiian Escape with all the Amenities
Located in one of the newest and most sought after resorts in Hawaii, this beautiful ground floor 2-bedroom, two full bath upgraded condominium with lanai and garage parking is right in the heart of the gated Ko Olina Kai golf course community. It is a short walk or...
Going Green at the Kuleana Ranch.
Off grid luxury. Powered by state of the art photovoltics solar hot water. Surrounded by thousands of acres of DNLR land. Super quiet and private. Complete with granite counters, open beam celings, tiled shower, mountain and ocean views. Partially covered 400 sq. ft....
Hilo Shangrila - Oceanfront, Pool and Hot Tub Private Vacation Rental
Let the oceanfront, gated retreat of Hilo Shangrila envelop you, with its private saltwater pool, hot tub, and covered lanai, all just a stone's throw from the peaceful Pacific. New air conditioning has been added in all bedrooms for total guest comfort. We are...
Top Floor Gem! Direct Ocean Views! Near Kaanapali #215
ALOHA AND WELCOME TO HALE KAI # 215 Located right on the ocean on the beautiful island of Maui, our second floor Condominium can be your home by the sea. View Molokai, watch sailboats pass by, and during the winter months, watch whales -- all from the lanai. You can...
Waikiki 2 Bedrooms with free parking near beaches, and Ala Moana shopping center
This condo is near beach, across from ocean in Waikiki. The home itself is a cozy two bedroom ( Queen size beds) home and one bathroom with two balconies. This condo is perfectly situated walking distance to everything in Waikiki. We are one block from Waikiki beach,...
White Sand Beach - Puako Beach House - Beach 69
Experience true paradise in this charming Puako beach house! Featuring two bedrooms and two bathrooms, it's the perfect spot for a family or small group getaway. Just steps away from Beach 69, you can enjoy the peace of the ocean along with a relaxing stroll to take in...
Maui Resort Rentals: Honua Kai – 6 Bedroom Oceanfront Gem, Stunning Ocean Views, Over 4500 combined Sq. Ft. w/ 2 Built-in Viking B.B.Q.s
This 6 bedroom gem combines two of our very finest adjacent 3 bedroom oceanfront residences to create a true masterpiece, perfectly suited to larger groups or families. Each of these oceanfront Ali'i (Hawaiian word for royalty) residences offers sweeping oceanfront...
Lush, peaceful, Vista Waikoloa B201! Walk to the beach, sunset, dinner & shops!
OWNER OPERATED. Our condo is perfect for 1 or 2 couples with King and Queen beds and 2 private bathrooms (1 ensuite). It is a spacious end unit with garden views from every window and a peek of the ocean from the huge covered lanai (400 square feet) with dining table...
Private lanai steps from the Fairway, fully stocked for a home-like experience
Very comfortable! Relax on your own private lanai steps off the Second Fairway. Feel the wonderful trade winds sweep across the Greens and take in the aroma of the beautiful Plumeria trees and Hawaiian foliage. This unit is fully stocked with all the amenities needed to...
Beachside Retreat with High-Speed Wi-Fi and Pool
Summary:🏖️ Walk to the beach, shops & top restaurants 🌅 Stunning garden lanai – perfect for coffee & wine 🛏️ Ultra-comfy queen beds for a restful sleep 💦 Resort-style pool, hot tub & BBQ area 📺 Smart TV & high-speed WiFi for entertainment 🚗 Free...
Hilo Lagoon 2 BD Condo-A/C, Pool
About this spaceThis peaceful condo is located in the heart of Hilo at the Hilo Lagoon Center. Walking distance to downtown, restaurants, shopping, lagoons and Hilo Bay parks! Fully Air Conditioned, total amenities, 24 hour security bldg.This nice 2-bedroom condo offers...
Golf course views with custom gourmet kitchen
Kapalua Golf Villa 18T1&2 is a 2-bedroom, 2-bathroom villa situated right on the Kapalua Bay Course and can accommodate up to 4 guests. Beautifully renovated, step inside to enjoy the high end kitchen featuring top of the line appliances, custom cabinet, and gorgeous...
Secluded Luxury At The Beach!
Aloha! This spectacular one-bedroom apartment is located direct ocean front with panoramic mountain and ocean views from sunrise to sunset. On the lanai, you have the feeling of being on a cruise ship, looking down directly into the ocean. The constant sounds of the...
ICC 34 Spacious 2BD Plantation Cottage w Pool AC Near Beach
International Colony Club 34 Spacious and Clean 2Bedroom Tropical Plantation Style Cottage in Kaanapali with Pool, AC Throughout, and Close to Beach; Your Perfect Maui Vacation REE daily activities included with your stay value up to $570! Complimentary admission, every...
PK D304 Remodeled Kaanapali Condo Ocean Views Pool AC
Papakea D304 Stunning Ocean Views & Lush Tropical Grounds At This Home Away From Home 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...
Great 2bd condo on iconic Sugar Beach
Kihei Sands B2 is a 2-bedroom, 2-bathroom condo located on the 2nd floor that offers a three-split air conditioning system - one in every room and can accommodate up to 6 guests. Access to the second floor is by stairs only; this low-rise complex does not have an...
KBR #302 - 2 Bedroom/2 Bath Ocean Front Upgraded Condo on Sugar Beach!
Tiled throughout, the interior of this upgraded 2 bedroom/2 bath unit is clean and bright with a view that stuns you every time you walk through that front door! The beautiful furnishings and gorgeous granite & stainless-steel kitchen add to the appeal. While you...
Beautiful studio condo on Kaanapali Beach
Honua Kai H237 is a cozy 1-bathroom studio located on the 2nd floor in the Hokulani Tower and offers central A/C, garden views, and an in-unit washer/dryer. This property has elevators for easy access. Unit H237 can accommodate up to 4 guests. The living room features a...
Panoramic View of Black rock and beach
One bedroom, 2 bath beach front condo at The Whaler on Kaanapali Beach in Maui, sleeps 5. Beautifully appointed, on the 9th floor overlooking the Pacific Ocean this well maintained Maui beach condo features breathtaking ocean views, and every convenience in your...
Permitted Hawaiian Princess condo on beach with sea turtles and amazing sunsets
This mid-floor beachfront condo at the Hawaiian Princess comes complete with a spectacular sunset ocean view from the lanai. The condo has been remodeled with the best of everything. Amenities include a deluxe fully equipped kitchen with top-of-the-line stainless steel...
Oceanfront on Kauai starting at $140/night!
Our 1 bedroom oceanfront Kauai condo, unit 111, has been with VRBO for over 10 years and has been booked almost everyday with over 100, 5-star reviews. You will find yourself right on the ocean and far from the highway! Sit and relax on your private lanai while watching...
Kalanikai 306: Cozy Oceanview Unit w/ AC & Shared Pool in the heart of Kona Town
Stay in the heart of Kona town at Kalanikai 306, a recently remodeled 1-bedroom, 1-bath condo that blends cool comfort with a walk-everywhere location. From your top-floor lanai, enjoy tranquil views of the pool framed by palms, with the Pacific glimmering beyond. With...
Oceanview, private pool, 5 acres of avocados! Gorgeous coffee district jewel!
Pu'u Mahana Plantation is the perfect destination for vacations and celebrations. Our hosted property lies in the heart of the coffee district, a secluded tropical estate offering guests a tranquil setting, 7 acres of manicured avocado and citrus trees, and lush borders...
Steps to beach! - Kihei Holiday 113
This beautiful, Two-bedroom/One-bath condo is just a two-minute stroll from one of Kihei’s most stunning beaches! Watch the sunset over the ocean accross the street, take long walks along the sand all the way to Maalaea Harbor, or cool off with a dip in the warm...
Deluxe Two Bedroom Partial Ocean View Luana Kai Resort B307
Unit B307 with AC is a deluxe, two bedroom two bathroom. It has a partial ocean view and courtyard view with tiki torches at night. B307 has a full wall mirror in the living room. A mix of carpet and tile graces the floors. The furnishings are rattan and wood. The...
Waipuna Hale: Oceanfront Cottage w/Panoramic Views, Yard, & Private Beach Access
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.Welcome to Waipuna Cottage, a charming...
Kona Alii 707 Stunning Top Floor Penthouse w/ Roof Top Deck, AC, & Elevators
Beautifully remodeled spacious 1 bedroom, 2 bath that includes AC in the living room, modernized kitchen, large lanai, and 7th story viewing sundeck where you can bask in the Hawaii sunshine or under the shade of the outdoor umbrella, enjoy sunsets, & stargaze at night!...
Plantation Hale Suites K5, King Bed, AC, Wifi, Near Shops and Beaches
No Resort Fees! Plantation Hale Suites Unit K5. Kauai Vacation Rental in the heart of Kapaa Town. The perfect Kauai vacation rental for the budget minded traveler. All vacation rental units have spacious bedrooms, are non-smoking, air conditioned, and fully furnished....
4 br Luxury Home in Kukuiula w Pool
Spectacular golf course views are just some of the highlights of the Pa'ina Makai vacation rental in the luxury Poipu community of Kukuiula. Pa'ina, meaning “to gather” in the Hawaiian language, is the perfect name for this home, which has many open living areas for...
Oceanfront condo with ocean views, balcony, pool
Nohonani 301Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Live the true meaning of "island life" at this gorgeous oceanfront condo. Boasting expansive water and mountain views from...
Mesmerizing oceanfront condo with expansive views
Valley Isle 1109 is a 1-bedroom, 1-bathroom condo on the 11th floor featuring amenities such as panoramic ocean views, a private washer/dryer, and 1 ceiling fan. This condo does not have air conditioning. Valley Isle 1109 can accommodate up to 4 guests with a queen-size...
Ideal Makai Golf Course location, 2 primary suites plus loft, ocean view & AC
Hale On'tarioOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'High on a cliff in Princeville, a prime neighborhood in the heart of Kauai’s North Shore, Hale On'tariō is perfectly...
Private, quiet, ocean view home. 5 minutes from the beach!
Tiny home with ocean view and loaded with character and amenities! Quiet, serene, high ceilings, AC and more! 5 minutes from the beach, and gorgeous 2nd floor lanai (patio) overlooking the neighborhood.
GC 163 Spacious Wailea 2BD w AC Pool Close to Beach
Grand Champions 163 Spacious 2Bedroom, 2Bathroom Luxurious Wailea Condo. Ideal Location to Walk to Beach, Tennis, Golf, Fine Dining, Luxury Shopping, and so much more. FREE daily activities included with your stay value up to $956! Complimentary admission, every day of...
Maui Resort Rentals: Honua Kai Konea 345 - Large 2BR w/ Great Interior Courtyard Location
Konea 345 is a luxurious two-bedroom suite offering lush interior courtyard views as well as partial views of the ocean through the palm canopy. Guests will enjoy its fantastic location located in the closest two-bedroom column to the ocean in the desirable south facing...
Sugar Beach Resort #305
Beach Front Sugar Beach Resort. 3rd Floor, Ocean View Unit. Beautifully updated unit with sweeping ocean views. Enjoy all of the amenities in a clean, well-kept property. The entire complex sits ocean front, there are no roads to cross to get you onto the beach! 305 is...
Hibiscus Beach Cottage, Steps to Beach, Beautiful Mountain Views, TVNC#5067
"Hibiscus Hula Beach Cottage". Kauai Vacation Rental, Anahola, Kaua`i, Hawaii. TAT ID#: TA-092-402-4832-01, TVNC#: 5067. On-Island Manager, Garden Island Properties LLC, Kapa'a Kaua'i. Accommodates up to 4 guests, including children and infants.Step back into the 1950's...
Beautiful ground floor unit at Kiahuna plantation with A/C.
Aloha and welcome to paradise at Kiahuna Plantation Unit 86, a stunningly remodeled one-bedroom, one-bath condo on Kauai’s sunny south shore in Poipu Beach. Nestled in the northeastern corner of this 35-acre resort, this ground-floor retreat boasts zero-step...