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.
Le'ale'a by AvantStay | Ocean + Mountain Views!
Le'ale'a — that sunny, blissful feeling of wonder and joy you only feel when immersed in the beauty of a place like the Hawaiian islands. And there’s plenty of it here! In the heart of Mākaha Valley and surrounded by stunning tropical mountains, this bright...
Sunset in Paradise Oceanfront 1BR/1BA Condo at Kona Reef Fast WiFi & Central AC
Enjoy breathtaking sunset views every night from this beautifully updated condo steps from Downtown Kailua-Kona village with AC in both the living room and bedroom.Sunset in Paradise is your private paradise with gorgeous ocean views straight from a postcard. Relax on...
Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets
This breathtaking 3 Bedroom plus bunkroom, 2 bath single level home is located just minutes from Kailua, Kona and some of the most beautiful beaches in Hawaii. Everything in this house is new! Fresh full remodel just completed. This includes a brand new gourmet kitchen,...
Best Ocean Views at Kihei Kai Nani #206nSteps to the beach 1 Bdrm / 1 Bath
Looking for the best view at Kihei Kai Nani? It is unit #206! This updated, corner penthouse boasts stunning beach and ocean views from the living room and lanai (patio). Relax to the sounds of the ocean and enjoy sunset views every night from the lanai or living room....
Honolulu Condo Stay w/ Balcony: Walk to Beaches!
Embark on your next island adventure and stay at this Honolulu vacation rental located in the Chateau Waikiki community! When you stay at this 1-bedroom, 1-bath condo, you’ll have access to community amenities like outdoor pools, a game room, a fitness center, and...
Cycle or Walk to Hanalei Bay
Totally remodeled, updated - all new furniture, fixtures, finishes.TVNC - 5119This vacation rental is located in Hanalei which is in the tsunami evacuation zone. The house is in the quintessential beach town of Hanalei. Walk to the bay for a surf, swim or beach walk....
Best location at Kuleana (Unit 405)! New Remodel. Spectacular Oceanviews.
Welcome to your island escape at the Kuleana Resort, West Maui’s hidden gem. This newly remodeled oceanfront 1-bedroom, 1-bath condo offers the perfect blend of comfort, style, and location—just steps from the shoreline, heated pool, and resort amenities.Enjoy...
Spectacular home, pool spa near Kahala Beach. MAY CANCELLATION - CALL NOW!
An Oasis of Calm. Understated Elegance. These are the thoughts that first come to mind as you enter this stunning, contemporary property, offering a quintessential Hawaii experience in one of Oahu’s most upscale neighborhoods, steps away from the world-renowned,...
Newly Renovated Condo with SUP Paddle Boards and Golf Clubs Included
Newly renovated luxury short term vacation rental for up to 29 nights 2 bedroom, 2 bathroom en suit condo inthe greater Keauhou Resort area. Quiet Concrete Building! No Paper-Thin Walls Here, Folks!Located on the 8th fairway, our beautiful condo is situated in the...
Calming Volcano Studio 2 Blocks From The Ocean
This comfy and clean Volcano Studio is located 2 blocks from the beach and Ali'i drive where all the best attractions are such as tasty restaurants, fun retail shops, bars, coffee and smoothie spots, fresh farmers markets, Magic Sands Beach, and much more. The Volcano...
Thoughtfully Remodeled 3 Bedroom Townhouse North Shore Hale 6B
E Komo Mai (welcome!) to "The Cozy Aloha", a lovely 3-bedroom townhome oasis in the peaceful north shore community of Hale Honu in Princeville. This newly renovated 1,148 sq ft split-level condo seamlessly blends modern comfort with tropical charm.Step inside to...
NEW Construction! Just Steps from Maui's Best Beach!
UPDATE: THIS HOME WAS UNAFFECTED BY THE FIRES. FUTURE BOOKINGS ARE SECUREBRAND NEW CONSTRUCTION finished in Sept 2018! No expense was spared in this beautiful 1800 square foot gated and private home. Just steps to Maui's best sandy beach (perfect for family swimming and...
Ocean view studio with WiFi, balcony, onsite pool/spa/bar/grills, & beach access
Islander on the Beach 367Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in a tropical retreat at the Islander on the Beach! This beachfront complex hosts a bevy of onsite...
VIEWS VIEWS VIEWS with AC! Large Beautiful on Golf Course
Emmalani Court Unit #110 is the only 3 bedroom condo with AC on the cliff in Princeville! You will notice the absolutely amazing views as soon as you walk in. This peaceful location allows ocean views from every bedroom and the living space. This ground floor unit is...
Waimanalo Beach Cottages – Tranquil Island Retreat Steps from the Shore
Uncover the allure of Waimanalo and lose yourself in the tropical paradise of Waimanalo Beach, where our exquisite cottages and breathtaking surroundings await. Embark on a journey of discovery by indulging in the myriad of exciting activities we have to offer....
Luxurious Hali'i Kai Townhome with fabulous Ocean views and Private Ocean Club
Hali'i Kai Ocean Front Resort is truly a gem on the sun-drenched Kohala Coast of the Big Island in the Waikoloa Beach Resort. The properties' grounds are well-kept, and the sunset views are AMAZING! Our unit, Hale Little Blue Whale (7F), is a luxurious 3 bedroom, 3 bath...
Take advantage of our introductory rates! Your Hawaii home is ready for your arrival
Take advantage of our introductory rates! Your Hawaii home is ready for your arrival.If you're looking for the perfect place to spend your next (or first!) Hawaiian vacation, then you need look no further than this light and airy two bedroom 2.5 bath townhome that can...
Kuuipo Hale - Plantation-Style Beach House on Weke Road in Hanalei - Short Walk to the Beach & A/C!
Kuuipo Hale is the Sweetheart of Hanalei! This 3 bedroom/2 bath plantation style home is a super cute, beach house located right in Hanalei - a super short walk to the beach and just a few blocks to town. Bedding configuration is: 1 King, 1 Queen + 2 Twins so can...
Napali Sunset Views+Pool/Spa + Bali Hai
Welcome to island paradise on Kauai’s coveted North Shore! This stunning home boasts an expansive open-floor plan designed to capture the breathtaking natural beauty of the island. Flooded with natural light, the airy living space seamlessly blends modern elegance...
A/C!15% Off Kahana Sunset 2BR/2BA Beautiful Condo Near Kaanapali Napili Kapalua
Our condo, now with Air conditioning! Our condo is in north Lahaina, far away from the fire affected areas. We are considered to be located Napili Honokowai. Our unit E-8, is one of 72 units in an oceanfront resort. This unit is a 1000sf townhouse style with additional...
Rare find w/ 2 AC, 2 min walk to beach, Remodeled #151, ground floor!
New shortened cancellation policy! Book before it's gone! New ownership! New A/C in both Living and Bedroom! One of the only units in Kiahuna with Air Conditioning in both rooms!1bd/1b newly remodeled condo inside beautiful Kiahuna oceanfront resort. The perfect spot...
Puako Beach Getaway - Luxury Vacation Home with Old Hawaii Charm
Please note that while construction is ongoing for a separate ohana on the property, the main house is fully available for rental this holiday season. Though the ohana will not be ready by Christmas, the main house remains a peaceful retreat where you can experience the...
3982S Kalakaua Gorgeous Princevile Studio
Raise your vibes and take in the natural beauty and gorgeous architecture of this Island Style Home, built by a master carpenter.This spacious studio attached to the main home is located in a peaceful cul-de-sac near Queen's Bath, Hanalei Bay, and the forthcoming...
Vista E 302 Newly Painted Remodeled View Penthouse
Top Floor larger condo with ocean, bay, and both Mauna Loa and Mauna Kea views. Perhaps the best view in the complex.. Large lanai with all nearly new Tropitone furniture including tables, chairs, and chaise. We have just completed painting entire unit, added granite...
Hale Iki - A lovely Little House on the beautiful Big Island
Hale Iki is a treasured family home for 3 generations. Tropical sunsets and the wide Pacific Ocean is all yours, right out front, all day long for you to enjoy. Recently remodeled, Hale Iki has a darling new kitchen with black sand granite countertops, ocean seaglass...
Na Hale 4 at Pauoa Beach - Private Oasis - Luxury at Mauna Lani Resort - Exclusive Access to Pauoa Beach Club and Amenities
Welcome to Na Hale 4 at Pauoa Beach Club, your luxurious retreat in the heart of Hawaii's premiere Mauna Lani Resort. Nestled within the prestigious gated community of Pauoa Beach Club, this stunning estate promises a perfect blend of tropical serenity and modern...
Oceanfront...Endless Sunsets Everyday!
This charming three bedroom home offers a private "local" experience in one of Maui's rare oceanfront neighborhoods. With idyllic views of the ocean and sunsets, this home promises many unforgettable memories. Our clean and cozy home is complete with all you need and...
Special! Coconut Plantation 1214-2 Ko Olina Beachfront Escape Resort Amenities
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 Coconut Plantation 1214-2 Aloha...
Waipouli Beach Resort Exquisite Ocean View Condo with Beach Front View
Experience a Vacation of your Dreams in Exquisite Luxury Oceanview Waipouli Beach Resort & Spa H204 offering one of the most spectacular views of the sparkling blue azure Pacific Ocean as it washes over the white sand beachfront just beyond the living room and bedrooms...
Poipu Paradise Beach Condo
Welcome to the South Shore of the Garden Island of Kauai and beach town of Poipu! Your stay at our well appointed modern beach inspired condo will be a wonderful place for your Hawaii vacation. Just a short 5 min walk on the greenway to Poipu's beaches for activities...
Ekahi 4C - Quiet Garden View Close to Beach - 20% off Summer pricing
1 Bedroom, 1 Bathroom, Sleeps 2-4*** Now offering for a limited time - 20% off Summer pricing ***Located in the lower village, unit 4C is a ground floor unit is backing on to a quiet ravine and surrounded by a tropical lawn area where children may securely play. Very...
Ocean & Diamond Head View Condo at Waikiki+Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Hale Kai - Best Value Beachfront Home Steps from Beach
Youtube Video Presentation: https://youtu.be/-c1tR8mMI1gHale Kai in Hawaiian means “ocean house” as there are spectacular views of the coastline and a white sand beach from every room. This home sleeps four with two bedrooms, two bathrooms and laundry facilities. It...
NEW - Spectacular Modern Ocean Front House Huge Garden Private Sea Access
IMPORTANT: Due to Hawaii regulations this property is only available for a minimum of 30 nights. PLEASE do not inquire if you are looking for a shorter stay, we simply can not accommodate you. However, the property is very special, and the price pretty low, so you may...
Keauhou Punahele B-308 Top Floor, Ocean Views, 3 bedrooms, 3 Bathroom!
A True Beauty at Keauhou Punahele: New Rental in 2024! Keauhou Punahele#B-308 is a gorgeous top floor rarely available 3 bedroom, 3 bathroom condo with approximately 1594 interior sq. feet with an additional 234 square foot lanai! It sits right on Keauhou Country Club...
Unique 8th Floor King bedroom condo Full kitchen Sleeps 3
Legally Permitted Rental - WAIKIKI GRAND HOTEL®815 One-bedroom Suite 2 Rooms in 1 Space1 King Bed1 Sofa BedFULL KITCHENGrab this one if it pops up for your dates! It is seldom available and often booked far in advance. Some years ago, a much-loved radio personality...
Luxury Beachfront Condo with Amazing 180° Ocean Views!! Corner Unit.
Kana'i A Nalu 317 by KNOWLES MAUI• Recent full-condo remodel, new everything• Third-floor corner unit with unobstructed ocean and outer island views• Freshwater beachside swimming pool • On Sugar Beach – the longest beach in Maui, great for swimming,...
$500 off the normal nightly rate of $1,250 for NEW April 2025 reservations
Charming coastal craftsmanship meets serene, private beachfront living. Set amid mature tropical plantings, Ulu Niu offers a tranquil, two-story retreat that captures refreshing coastal breezes in a stylish and intimate setting. The home’s thoughtful craftsmanship...
Hale Wailani - 4 BR Home on the Kohala Coast
Breathtaking vistas meet indoor-outdoor luxury. Perched in a gated neighborhood, this gracious two-story residence offers panoramic views of Mauna Kea, Mauna Loa, the Kohala Mountains, and Waialea Bay from nearly every vantage point . With 3,700 square feet of elegant...
Tranquil 2-bedroom condo with AC, in Kihei. Steps from the Beach!
Stay comfortably in Kihei at this 2-bedroom condo. The space features 1 king bed and 2 twin beds, perfect for a small group of guests. With WiFi, AC, and a cozy living room with a sofa bed, this condo offers a superb stay. The bathroom includes a shower and a hairdryer...
Panoramic Ocean and Golf Course Views ! Luxury Multi Level Townhouse at Hualalai Resort- includes 2 Golf Carts
Ke Alaula Villa 217B at Hualalai ResortExperience unparalleled luxury and tranquility at Ke Alaula Villa 217B, located within the prestigious Hualalai Resort. This exceptional property is situated within one of Hawaii’s most renowned and award-winning resorts,...
Newly renovated with ocean views from every lanai
Kapalua Bay Villa 29G5 is a newly remodeled 1-bedroom, 1.5-bathroom villa that can accommodate up to 4 guests comfortably. Step inside to enjoy the bright and airy main living area. Hawaiian-inspired decor and furnishings throughout the villa provide an elegant yet...
Beautiful Penthouse Condo w/ Direct Ocean Views - Sleeps 8!
Aloha! This condo has everything you'll need for an amazing Hawaiian vacation! We selected this condo because we love the layout and the ability to comfortably sleep 8 people. Also, the grounds at the Papakea Resort are immaculately maintained and have something for...
Maui Sunset B119 Beachfront Ground Floor, Ocean-View, Poolside Family Friendly!
- Updated, ground-floor, oceanfront condo.- Breathtaking, unobstructed sunset views!- Manicured park grounds directly accessed from the unit's lanai.- Tropical landscaping and outdoor pool with an activity desk for booking tours, activities, and water sports rentals.- 2...
Kona Oceanfront-Gorgeous, Quiet, Sleeps 6
Summary:Discover paradise at our stunning oceanfront retreat! Nestled amidst swaying palms and lush tropical greenery, this three-bedroom, three-bathroom sanctuary offers a serene getaway for up to six guests. Wake up to the soothing sound of waves crashing, and soak in...
Kahikole Street Estate – Four Seasons Hualalai Home with Pool & Spa
Aloha and welcome to your private oasis at the exquisite 4 bedroom home in Hualalai with amenities at The Four Seasons resort. Spectacular views include an unobstructed ocean panorama and the Kohala Volcano to the north, you also enjoy a front row seat of the 8th hole...
Indulge, just steps to pristine beaches, restaurants & shopping.
Introducing the enchanting Honu Hale Cottage, a captivating retreat just steps away from a picturesque stretch of warm sand where sea turtles find solace in the tranquil waters of the Pacific Ocean.Located in the peaceful Kihei area of South Maui, this unique sanctuary...
125+ 5star REVIEWS SAYS IT ALL! Golf & Ocean! LAST MIN CANCL APRIL! 169 +tx rate
Location: Grand Champions, Wailea, South Maui, Maui, Hawaii, USA (2 miles Kihei, 13 miles airport, 1/2 mile beach.) Accommodations: Condominium, 1 Bedroom, 2 Baths (Sleeps 2) Maximum occupancy is 2 adults 25 years old or older onlyCOME ENJOY OUR FULLY RENOVATED FROM...
Kulanakauhale 3558: Lavish Oceanview Estate, Private Pool & Spa at Hualalai
September 15 – Mid-November, 2025The Hualalai Resort Spa will be undergoing enhancements to the outdoor aqua-thermal areas of both the men’s and women’s locker rooms. During this time, massage, body, and facial treatments will be temporarily relocated to the...
Magical views of Hanalei Bay, Napali Coast and the Makai Golf Course in a beautifully styled home
Spectacular views from living room, two lanais, king and queen bedrooms. The whole house is light and bright, recently updated with new paint, flooring, light fixtures and all new furniture, high-end mattresses and linens. Cook's kitchen is stocked with everything...