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.
Wailea Elua Village | 1704
Wailea Elua 1704 is a stunning oceanfront vacation rental located a short stroll from one of the top snorkeling beaches on Maui. This spacious two-bedroom, two-bathroom corner unit spans approximately 1,600 square feet and comfortably accommodates up to six guests,...
Wailea Elua Resort Gorgeous Remodel #1507
Wonderful ocean views and serene location with a privacy garden and spacious outdoor area for relaxing, using the grill and having dinner. Beautiful finishes and amenities throughout this restful space. Access to tennis courts, putting green, workout center, pools and...
Sky Ala Moana 43rd fl PENTHOUSE Ocean & Diamond head view 1 Parking
-Luxurious Penthouse Retreat in the Heart of HonoluluIndulge in the ultimate urban oasis with our luxurious 43rd-floor penthouse condo, perfectly situated in the vibrant Ala Moana Center area between Waikiki and Kaka'ako. This prime location offers unparalleled...
Beachfront Molokai Sanctuary Romantic Getaway Writers retreat Solo Rejuvenations
3 Minute walk to the Beach! Hawaii as you imagined it 50 years ago! Breathtaking beaches only steps away in a serene, uncomplicated paradise of days gone by. Sparkling ocean views from the airy screened in lanai with only the sounds of waves at night and tropical birds...
Sugar Mill Cottage at Poipu Kai By Parrish Kauai - short walk to beach & quiet l
Sugar Mill Cottage is located in the heart of the Poipu Kai Resort community. It is the perfect location for beach access to either Shipwrecks beach or Poipu Beach park. A short stroll in either direction will take you to sun and sand!Enjoy the air conditioned bedrooms...
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
This Hawaiian plantation style suite is one of our largest and most spacious. It is very relaxing and romantic, especially in the evening when stars can be seen. This suite was named Hoku, meaning star in Hawaiian. You will find all sorts of star gazing tools in this...
Peaceful Location with Lush Tropical Views
From the moment you step inside this island-inspired home, you’re greeted by panoramic views of lush tropical gardens through a wall of windows. The beautifully landscaped yard invites visits from local birds, creating a peaceful soundtrack to your stay—best enjoyed...
Kama'ole One Beachfront Condo
Kama'ole One (oh-nee) means from "the Mountain to the sand" Discover the beauty of Kihei from this delightful beachfront 2-bedroom, 2-bath condo. Located on one of Maui’s finest beaches, Charley Young Beach. This wonderful property offers aloha spirit for all guests....
Hidden paradise with a hot tub, wood fireplace, large lanai, & jetted tub
Anthurium CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up to the melodic serenade of native birds and step out onto your private lanai to behold the lush, natural...
Endless Ocean Views from your Sugar Beach Retreat -Central AC #208
Come enjoy the amazing ocean views and breathtaking sunsets in our newly updated deluxe one bedroom, one bath, air-conditioned condo. Sugar Beach Resort, is just steps away from the 5-mile white sandy beach. Our beach access is excellent for swimming, snorkeling,...
Newly Remodeled Kailua-Kona Condo w/ Pool Access
A trip to the Island of Hawaii is calling your name and this breezy 1-bedroom, 1-bathroom condo in Kailua-Kona is the answer! Located just a quick walk away from the beach, this vacation rental provides a fully equipped kitchen, an in-unit washer and dryer, and access...
Makanui Estate - AC, Sleeps 17
MAKANUI ESTATE AT KOLOA KAI VACATION RENTALSA Private Paradise for Your Kauai EscapeWelcome to Makanui Estate, a luxurious retreat in the heart of Poipu offering breathtaking ocean views, serene mountain backdrops, and spacious accommodations for your family or group....
Maui Spring Break Deal: Stay for $199/Night! We now have A/C!
Annie’s Surf Shack Maui – Your Oceanfront Paradise AwaitsFor savings of up to 25%, no booking fees, and exclusive discounts, search “Annie’s Surf Shack Maui” online and book directly! Not in the Lahaina fire area, we’re safely located 6 miles north in the...
Elegant Poolside Penthouse with Private Elevator
Summary:F300 | TA-018-220-0320-02Experience elegance in our Poipu Penthouse Villa, boasting luxury designer furnishings and gourmet kitchens. Stay cool with central A/C and enjoy elevator access directly into F300. Relax amidst tropical views and exceptional luxury in...
NOW OPEN & REDUCED- up to > 4/21 ~ Platinum Maui Vacations Villa ~ ALL 5 STARS ~
THIS IS ONE OF THE GOOD ONES; NO DISAPPOINTMENTS HERE! ALL 5 STAR guest posted REVIEWS!VERY COMPETITIVE PRICING; VERY WELL APPOINTED; VERY NICE VILLA!Hawaii Tax ID# TA‐017‐672‐8064‐01Aloha! Welcome to Hale 'Ikena Makai, pronounced Ha-lay e-ken-na ma-ki, 'Home...
Kauai charm at affordable upstairs studio, walk to everything
Paniolo 210B - this lovely Paniolo studio is a comfy, convenient, and tranquil home base for your exploration of Kauai. It's an upstairs unit, quiet and away from the road, very close to the path to Anini beach and to the walking path through Princeville. Start your day...
Modern Luxury 2bed 2bath with Ocean Views and Easy Parking
Great care was taken in creating this comfortable, practical, and modern luxury home with ocean views from every room. Materials, colors and features uncommon in a rental were thoughtfully combined to create a unique, calm environment for relaxing. This is living well...
One of highest # of five star reviews, 1 of largest units, best panoramic views
This home is positioned at the very front row on the Maui Kamaole knoll, has spectacular panoramic ocean/sunset views and is known to have one of the better views than the other units at this resort. Being one of the largest homes at Maui Kamaole with its unique...
Waikoloa condo with amazing amenities! Close to beaches and golf courses.
Enjoy a centrally located condo with the perfect home base for your big island adventure. You are located just six miles from the island's most beautiful beaches along the Kohala Coast where you'll enjoy spectacular snorkeling, swimming, and other ocean activities....
Wyndham Bali Hai 3B Presidential ~ Sleeps 8 ~Resort Amenities! ~ FAMILY FRIENDLY
Enjoy a relaxing home away from home after days of adventure on Kauai. All units have washers/dryers, fully-equipped kitchens with everything needed to cook -- utensils, dishes, pots, pans, full-size stove, refrigerator, coffee maker, toaster, blender. An amazing oasis...
Hale Makai - Luxury Beach Home with AC and Private Hot Tub! TVR#5012
Welcome to Hale Makai, our luxury beach home located on the beautiful and sunny west side of Kaua'i. We offer a host of amenities and a picturesque location for a relaxing and unforgettable vacation experience.Take your pick of comfortable seating in the spacious living...
Fabulous Ocean View Condo, Near Kaanapali.
This is one of the best spots on Maui & a great way to support local businesses as Maui recovers. Easy access to anywhere you want to go, and close to shopping, beach and snorkeling. Snorkel in Kapalua, or go for a little hike - it's all a short ride away.Condo...
Sophisticated freshly remodeled two story Golf Villa w/Private Beach Club
This VERY PRIVATE- 2 STORY-CORNER VILLA with UNOBSTRUCTED MOUNTAIN VIEWS, along with the CONSIDERABLE BENEFITS offered thru Mauna Lani resort and hotel exclusively to owners and their guests, make this a very special opportunity for your holiday visit.The Mauna Lani...
Luxury Ko Olina Beach Villa with direct beach view. Sleeps 6.
Premium Beach Villa very close to the beach. B-208 is the closest villa to the beach on the sunset side. Enjoy direct views of the beach and ocean without looking past another lanai. Enjoy added privacy and ocean views on the desired sunset side of the beach tower....
Elegant Pili Mai 14-J: Spacious 3BR Villa with Pools, A/C, and Beach Proximity
The Resort:Pili Mai was built in 2019 and features plantation-style design, cobblestone drives, tropical gardens, a large swimming pool, a children's pool, spa, and an air-conditioned fitness room. It is nestled between Kiahuna Golf Club and the beautiful Poipu beaches:...
Papakea D206 - Ocean and pool views
Book with us and come to Maui to explore everything we have to offer!This well maintained 2nd floor private location has ocean, pool, and koi pond views from the lanai. Relax on the lanai listening to soothing Koi pond fountains while watching the whales breach in the...
Kamaole Sands 1-403 - Ultimate getaway! Spacious 2/2 with split AC, Large Lanai
Welcome to Kamaole Sands 1-403, your perfect Hawaiian retreat in the heart of South Kihei. This spacious two-bedroom, two-bathroom condo offers breathtaking ocean views from a large private lanai, where you can relax with your morning coffee or enjoy sunset cocktails....
SPECTACULAR ! Ground Floor Condo Sleeps 5 , Golf, Tennis, Gym, Pool, Jacuzzi
This is a an amazing 1 bedroom 1 Bath ground floor unit with plenty of space. It has been fully renovated with beautiful furnishings inside and out. It has lots of windows that lead out to a spacious patio. It has central air if the cool Hawaiian breeze is not enough....
The Jewel Box - Kehena Beach
Experience breathtaking ocean views from every level of this professionally decorated vacation home. Located on the Eastern side of the Big Island, The Jewel Box is a traditional Hawaiian bungalow remodeled with your comfort and luxury in mind. Features include...
Best value for prime location! Ocean & Golf Course View At Hali'i Kai 6E
Come and enjoy all the amenities of a fully stocked three bedroom condominium at Hali'i Kai. Our beautiful condo (in Building 6) in Hali'i Kai (in the Waikoloa Beach Resort area) is the best value in the area. The bedrooms offer 1 King, 1 Queen and 2 Twin Beds. Bringing...
new Luxury Ocean View Penthouse
Summary:Relax on the expansive lanai with ocean, mountains, and golf course views in this newly remodeled penthouse. Enjoy sunsets with a drink from your private bar. High ceilings, abundant natural light, and two large bedrooms, each with a king bed, blackout shades,...
Hale Pahonu – Secluded Polynesian Beachfront Estate in Waimanalo
Make unforgettable memories in this secluded, polynesian-styled beachfront estate situated on the eastern side of Oahu next door to the famous Magnum PI Robin's nest. Flanked by the majestic Ko’olau mountains on one side and a reef-protected lagoon and beach on the...
Islander Beach Resort, condo # 166
This ground-floor studio condo is the perfect tropical getaway for your most memorable vacation. Grab a cold drink, head out to the private lanai to the lush Hawaiian gardens, the sound of birds, and sparkling waves. The private lanai is furnished with a 4-person dining...
Wailea Beach Villas | PH209
Welcome to Wailea Beach Villas Penthouse 209, a beautifully furnished 2,600 sq. ft. garden view suite that offers a serene escape overlooking the family pool. This open and airy vacation rental is designed for relaxation and leisure, featuring an expansive tiled great...
40% off ! Oceanfront Views in the Heart of Kihei - Full A/C, W/D, 85"TV
40% off nightly rates during construction. Are you the kind of travelers who get up early and get going? This can be a great opportunity for you. Construction hours 8am-4pm. No construction on weekends or holidays. No impact on your unit. Noise ranges from occasional to...
Spacious Maui Paradise Retreat-Across from 2 Fave Beaches MK-B202
Experience paradise in this fantastic 2-bedroom, 2-bath Maui Kamaole condo. Located in the coveted B building, closest to the main pool pavilion and pristine Kamaole beaches, this newly renovated vacation rental sleeps up to 6 guests comfortably.Highlights:• Prime...
Wow! Maui On Sale-Inner Courtyard Ocean View-Steps to Beach & Pool-100+ Reviews
WELCOME TO OUR VRBO LISTING and RENT FROM AN ACTUAL OWNER.Honua Kai is a special place combining the benefit of a luxury condo in a spectacular resort setting. We look forward to sharing our slice of paradise with you and know you will love it as much as we do. OUR...
If Looks could Kill...Prime Location, Close to pool. Weekly Discount!
Oceanview Luxury Retreat – Steps from Pool & Beach | Unit E, Building 16Welcome to your Hawaiian home away from home! Nestled in the heart of paradise, this beautifully appointed 3-bedroom, 2-bath condo offers garden and sunset views, upscale amenities, and unbeatable...
*Lauloa 306* Maui Prime Oceanfront Condo, A/C!
This nicely remodeled 3rd-floor condo offers breathtaking views of Maalaea Bay, the grand volcano Haleakala, and the sparkling Kihei lights at night from the private lanai! The primary suite features a comfy king bed and ensuite bathroom with a walk-in shower and a...
Maluhia Ma Ka Honua: Huge Ocean View Home in Poipu
Maluhia ma ka Honua is Hawaiian for "Peace on Earth" and that is what you will find in this beautiful house located just a 40 second walk to the ocean and just four houses from the famous Brennecke's Beach in Poipu Beach Park. The question everyone asks themselves as...
IRONMAN is Available! 100 Feet From Your Bed to the Ocean! Romantic Shower for 2
Aloha and E'Komo Mai (Welcome!) to the SeaCluded Hideaway Inn Kona, Hawaii where you are only 100 FEET FROM YOUR BED TO THE OCEANS EDGE™ !Our unique Hawaiian-themed 4-bedroom, 3-bathroom property on the Ocean Side of Ali'i Drive offers an unbeatable location and...
NS H262 BeachFront Condo w Ocean Views Pool Hot Tub
Napili Shores H262 NEW LISTING Ocean Views and Beach Days from this West Maui 1Bedroom Tropical Retreat! 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...
Hanalei Bay Villas #2, Beautiful Free-standing Hawaii Villa, walk to beach
Welcome to your tropical retreat at Hanalei Bay Villas #2 in Princeville, Kauai.Unwind at the adorable and comfortable free-standing 2-story villa located in the prestigious community of Princeville! This spacious, fully furnished 2 bedroom and 2.5 bath stand alone...
PARADISE OCEAN VIEWS & GOLF w/ A/C + Pool / PickleBall / Tennis
E Komo Mai - Welcome to our Hawaiian Sanctuary (otherwise known as our Hawaiian Happy Place) offering nearly 180-degree Ocean View over Waikoloa Village Golf Course, with golf (at reduced rates plus a range/putting green), free tennis and pickleball (under lights), and...
Luxury, oceanfront condo. Newly renovated; best location! Sunset views! #404
Aloha! Welcome to Sugar Beach Resort, #404! This luxury renovated unit has all you need for your perfect Maui vacation: incredible ocean sunset views and just steps from crystal clear Sugar Beach. During whale season (Nov-April), you will see humpback whales from the...
Gorgeous 3 Bedroom Condo as Close to the Beach as You Can Get!! 30 day rental
Perched on the top floor of Foster Tower, this stunning three-bedroom penthouse offers an elevated island living experience with sweeping panoramic views of the Pacific Ocean, Diamond Head, and the Honolulu skyline. Designed for those who appreciate sophisticated...
FOUR PADDLE Mountain view with full kitchen, AC, washer/dryer, Wi-Fi, parking
Four Paddle #2311 – 2140 Kuhio Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Located on the cool side of the building, you'll enjoy lovely Ala Wai Canal and Ko'olau Mountain views from this well-equipped 23rd floor one-bedroom condo (553 sqft...
New Listing, Wailea Ekahi 4A, Close to Best Beaches, Shops of Wailea & World Class Golf
Escape to paradise at Wailea Ekahi Village 4A, Maui's dream vacation rental. This spacious 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of indoor comfort and outdoor living.Unwind in Style:Indulge in expansive living areas, ideal for families or...
FLASH SALE 25% OFF MAY Oceanfront 2bd/2bth Penthouse w/AC Menehune Shores #625
Nani Kai Escape is a 6th Floor Oceanfront Penthouse with breathtaking ocean views offering the perfect Hawaiian getaway. Maui is known for it's world-famous beaches so come check that off your bucket list and literally stay steps from the beach. From the moment you...
DISCOUNTED RATES! Brand New - Completely Remodeled, steps from the beach.
This gorgeous unit was remodeled in 2020 and professionally designed with the most modern amenities. It features a King bed in the bedroom as well as a pull out cabinet Queen sleeper and Queen couch sleeper, each with memory foam mattresses. You will find all the modern...