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.
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....
Ohana Retreat: 10 BR Poipu Estate with Private Pool, Sleeps 28
OHANA RETREAT AT KOLOA KAI VACATION RENTALSYour Ultimate Group Getaway in PoipuWelcome to Ohana Retreat, a one-of-a-kind vacation rental in Poipu that can accommodate up to 28 guests, making it the perfect haven for large family reunions, retreats, or multi-family...
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....
Valley Isle Resort #1202 - Vacation West Maui
Free Parking, Free Wi-fi, No Resort Fees★Newly Installed AC Unit will keep you cool!★Unit 1202 at Valley Isle offers a comfortable and functional living space ideal for a small family or a couple seeking a beautiful retreat on the Maui coast. This 1-bedroom,...
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....
Maui Resort Rentals: Honua Kai – 4 Total Bedrooms, Stunning 5th Floor Deluxe Ocean Views from Every Room!
This phenomenal 4BR deluxe oceanview offering pairs two neighboring 5th-floor residences for over 2100 sq ft of combined interior living space. Each suite boasts spacious floor plans, luxurious finishes, and breathtaking views of the Pacific Ocean from high above the...
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,...
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...
40% off ! Oceanfront Views in the Heart of Kihei - Full A/C, W/D, 85"TV
Panoramic ocean views from this beautifully updated, fully air-conditioned condo at the popular Island Surf complex in Kihei. This airy guest favorite is across from Kalama Beach Park and Cove Beach. It's a 2-3 minute walk to food trucks, bars, restaurants and shopping....
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...
Wailea Elua Village 2104 - 2 Bedroom Garden View Condo
Wailea Elua 2104 is a charming two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. Designed with an island-inspired aesthetic, this condo blends comfort with contemporary style, making it an ideal getaway for families or groups of friends....
Wailua Bay View 107 Oceanfront condo
This 1-bedroom condo in Kapaʻa is perfect for your escape to paradise. With WiFi, and a washing machine, guests can enjoy a fantastic stay in this wonderful space. The pleasant atmosphere and convenient amenities make it a great choice for a relaxing getaway. Fall in...
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 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...
Ma'alaea Surf #C-7 – Oceanfront Getaway with Spectacular Views & Pool
Ma‘alaea Surf #C-7 – Remodeled Ocean View Townhouse with Premium UpgradesWelcome to Ma‘alaea Surf #C-7, a stunningly remodeled two-bedroom, two-bathroom townhouse with breathtaking views of the Pacific Ocean. This rare condo features an in-unit washer and dryer,...
Oceanfront-Amazing Views-Quiet-Private Turtle Viewing Beach-Great Location
Noelani 119 sits only 10 feet from the water's edge, and we welcome you with so much Aloha....Some of the many owner-supplied extras are:• Beach chairs• Beach umbrella• Beach towels• Cooler• Complimentary daily turtle viewing and free sunsets!We provide all of...
Luxury Ground Floor Villa, Sunset/Ocean Views, Huge Lanai, 2 King MBR suites
We first listed Villa One on VRBO May 2022. We've had many happy guests, and many 5 star reviews. This exceptional and private condominium is the first ground floor villa at The Shores at Waikoloa Beach. Villa One has views of the Pacific Ocean peeking through Palm and...
Penthouse with Panoramic Ocean Views From Private Lanais
Welcome to your dream getaway on the Garden Isle! This top-floor penthouse in the heart of world famous Poipu Beach offers the perfect blend of luxury, comfort, and island charm. With soaring vaulted ceilings, four spacious bedrooms, and 3.5 baths, this retreat is...
Ultimate Oceanfront Luxury - Polo Beach Club #706 in Wailea, Maui
Polo Beach Club 706 is an ideal home base for your tropical getaway. Make your Maui experience one to be remembered. Whether you’re celebrating with family, vacationing with friends, or simply seeking a peaceful and private alternative to a high-end hotel, our...
Surf Cove - Ocean - Jeep
Welcome to Maui! Stay in this stylishly updated, fully furnished vacation condo in the heart of Kihei. The ground-level unit lanai/patio is conveniently located steps away from the resort-style pool and outdoor barbecue area. The interior consists of top-of-the-line...
Mauna Lani Terrace - G301 New Rental Opening Special Rates - Stunning View
Mauna Lani Terrace G301. We few reviews because we just launched this jewel of a spot. The view is gorgeous and the bathrooms and kitchen have been updated! Stunning ocean views overlooking the pool and beach! This updated one-bedroom features two beautifully renovated...
Spacious luxury 2-floor villa with breathtaking ocean, golf, and mountain views.
Welcome to our spacious luxury villa, where you can enjoy breathtaking ocean views, golf courses, and mountains.This exceptional two-floor, 2-bedroom, 3-bathroom unit beckons you into a bright and open layout, encompassing an impressive 1756 square feet of interior...