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.
Chic Waikiki condo! Kitchen, city/mountain views, close to beach!
Ilikai Marina #1287 – 1765 Ala Moana Blvd.Fall in love with this beautifully remodeled studio located near the Ala Wai Yacht Harbor! With city/mountain views, this 427-sqft condo (plus small 28-sqft lanai), is centrally air-conditioned, fully-furnished, and has stylish,...
Lush Garden Island Condo | Pono Kai Resort | PK-F105
Pono Kai's pool and spa will be closed January 6-31, 2026 for the installation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Lush Ocean View Condo is a 1 bedroom, 1 bathroom ocean view condo located...
Contemporary City View One Bedroom Condo at the Ilikai w/King Bed & AC!
Experience the beauty of Waikiki with Happy Vacations! Our team is excited to offer you a contemporary condo at the Ilikai. You'll love the spacious balcony, thoughtfully furnished with attention to detail, providing an ideal spot to sip your morning coffee and take in...
Bright, open-concept living area with ocean view
Papakea B306 is a bright 1-bedroom, 1-bathroom condo with a stunning ocean view, featuring amenities such as a washer/dryer, and air-conditioning! The condo was remodeled in 2021 and 2024 and can accommodate up to 3 guests with a King-size bed in the bedroom and a...
Sunset Oasis in Paradise
Wake up to songbirds every morning, enjoy breakfast on the lanai and watch the day unfold. End the day on the lounger as the sun sets right before your eyes after exploring the island. Our home in paradise offers:o Step through the front door and be greeted by...
Majestic North Shore "Cliffs" Condo
Princeville is one of the most majestic places in the world and our spacious condo allows you to take in the views of both the ocean and the mountains.Corner unit, tons of natural light, 2 lanais (off bedroom and living room) offering gorgeous views and cooling ocean...
1 Bdrm Ocean View walk to Turtle Beach, close to Kona Village&Magic Sands Beach
Cute one bedroom beach side apartment with ocean view in perfect location, on Ali'i Drive across the street from Turtle Beach. Turtle Beach access 2 blocks south at white and blue Public Access Sign, follow to shoreline. Be careful traversing the rocks, wear water shoes...
Marriott Maui Ocean Club- Stunning Three Bedroom Villa Lahaina/Napili Towers
Concierge Realty is proud to present luxury villas at Marriott Maui Ocean Club TowersWe are able to offer 7 night weekly rentals with check-in on Saturdays only.Beginning Aug. 23, 2025, to Dec.16, 2025, Marriott’s Maui Ocean Club - Lahaina & Napili Towers will be...
Breathtaking Panoramic Bali Hai with Unobstructed Bali Hai Ocean View
Named by Condé Nast Traveler as one of the top tropical resorts in the world. This is truly the Hawaii of your dreams.Hanalei Bay Resort is a scenic paradise with awe inspiring views. You'll be surrounded by cascading waterfalls and lush foliage - a mixture of tropical...
"Oceanfront Condo: Coconut Tree & Ocean Views, Whale Watching, Paddlers, and Surfers at Wailua Bay!"
"Picturesque Oceanfront" Wailua Bay View Condo with an Coastline ViewScenic Oceanfront View from this attractive top floor condo at Wailua Bay View. Decorative upgrades with splashes of color with a tropical Hawaiian touch helps you to feel at home. If you are looking...
Wheelchair Accessible Ground Floor 2BR/2BA Makani a Kai
This is a unique property on Maalaea Bay. Recently upgraded and renovated, it boasts wheelchair accessible features such as a large master bathroom, ADA compliant, including a large roll-in shower. Ground floor accessibility and very close accessible parking stalls make...
Elua 2303: Gorgeous Luxe Condo, Ocean Sunset Views
This property is hotel zoned, and not being affected by the recent proposed legislation.This bright and spacious condo is perfect for honeymooning couples, anniversary stays, and those just looking to escape to their own island retreat. Stunning ocean views and lush...
Spectacular Ocean Maui Sunset View
This 3rd floor condo is the perfect spot to base your Maui vacation. Casual Hawaiian themed decor with all the comforts of home. Spend your vacation as busy -- or as relaxed -- as you'd like. You can explore the island or just stay in and enjoy the fabulous view from...
Maui Kamaole A107: Spacious 1 Br Condo across from Kamaole Beach Park III
Relax in your personal piece of paradise! This spacious one-bedroom condo is located on the ground floor and has a private lanai with peaceful ocean views. This condo will accommodate two people with a queen bed in the bedroom. The fully equipped kitchen is the perfect...
Mauna Kea South Fairways 4 BR -4.5 Bath 180 Ocean Views & Private Pool, Sleeps 8
To see a walkthrough of the house, visit: https://my.matterport.com/show/?m=NffDEzCwbow&brand=0. Situated in the South Fairways of the Mauna Kea Resort, our home has beautiful views of the ocean and mountains, and is the perfect retreat for extended family or friends to...
North Shore Guest House @ Maui Adventure Villa
The North Shore Guest House is conveniently located on Maui's famous North Shore. Spacious, very comfortable, peaceful and quiet THREE (3) BEDROOM/TWO (2 BATHROOM HOME with a large living room and open-style kitchen. A king size bed in the master-bedroom and queen size...
OceanView Tranquility: Luxurious Condo with Spectacular Grounds - Elua #1104
Wailea Elua #1104 – Ocean View Comfort with Versatile Sleeping Options and Elegant Island StyleWelcome to Wailea Elua #1104, a beautifully situated ocean view condo offering space, flexibility, and island elegance in one of Maui’s most exclusive beachfront communities....
Kehena Treetop Bungalow-Near Black Sand Beach
Kehena Treetop Bungalow – Close to Kehena Black Sands BeachKehena Treetop Bungalow is a tropical paradise, nestled in among lush green foliage and fruit trees. You’re going to enjoy the beautifully refinished hardwood floors and the tropcial décor. This house is the...
Majestic Mountain Studio Retreat
Imagine vacationing in a brand new studio set in a peaceful valley. You're surrounded by Ka’ala & Waianae mountains, towering palms, mango trees, wild peacocks, & famous beaches.You take a sunrise/sunset stroll around the gated neighborhood (w/24hr security) and return...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 5th floor Ocean AND West Maui Mountain Views
This tandem package is comprised of two fantastic 5th floor two bedroom suites that are right across the hall from each other. Hokulani 510 offers delightful partial ocean views along with views of the West Maui Mountains and Hokulani 511 offers full ocean views along...
Luana Hale: Peaceful Garden Home w/ AC & Serene Lanai in Princeville
Discover serenity and sophistication at Luana Hale by Gather, a single-level luxury retreat in the heart of Princeville, Kauai. This three-bedroom, two-and-a-half-bathroom home offers 2,800 square feet of refined living space framed by lush tropical landscaping and...
Fantastic Oceanfront Condo at the Cliffs Resort. Great amenities & free WiFi.
Large 1 bedroom / 2 full bath ground-floor condo in Princeville, on Kauai's North Shore at The Cliffs Resort. No need to worry about struggling up stairs with your bags to get to this easily accessible condo. Check out our:1. Queen sized sleeper sofa in living room.2....
Tropical breezes, ocean view and sunny white sand beaches.
Tropical breezes, ocean view and sunny white sand beaches make this an ideal vacation rental house. It is furnished in a traditional island style with a fully equipped kitchen. Upstairs is a large ocean-facing master suite with a California King, an adjoining sun-room...
3 Bedroom Home with a Pool at Waikoloa Beach Resort
Enjoy a 3 bedroom home in Waikoloa Beach Resort at a nice price. This home is situated on one of the larger lots at Ainamalu and offers an open view with both the Mauna Kea and Mauna Loa mountains in the background.The spacious great room offers ample space for...
New Ductless Split A/C System! Close to complex pool and grocery store.
Nestled next to the Kona Country Club Golf Course, this one-bedroom plus den, two-bath condo at the Keauhou Palena complex offers a cozy retreat for your Big Island vacation. Take a quick dip in the pool located just outside, or go for a stroll down the road and enjoy...
Kolea 1A ~ 3 Bedroom Ground Level Kolea Vacation Rental
This ground-level villa offers a prime location with convenient access to a spacious, open grassy area directly off the lanai—ideal for children and anyone looking to enjoy the scenic views in a private, relaxing setting.As you step into the villa, you'll be welcomed by...
Tropical ocean front breezes and stunning views
Kahana Reef 321 does not have A/C, is a 1-bedroom, 1-bathroom condo on the 3rd-floor with oceanfront views! Kahana Reef offers an elevator for your convenience. Unit 321 can accommodate up to 4 guests. Fall asleep to the tropical sounds of Maui! In the master bedroom,...
Keoniana Kai - Pool & Hot Tub with Ocean Views
Keoniana Kai, Princeville Perched on a dramatic ocean bluff above the surf, Keoniana Kai, a 3-bedroom (King, Queen, Queen), 4-bath architectural masterpiece, that sits with panoramic ocean and white water surf views.Keoniana Kai, located in the prestigious town of...
All the beauty and tranquility that Kauai has to offer starts with this lovely villa.
Whether you are looking for an adventure-filled visit to Kauai or a peaceful retreat to recharge your senses, this is the place for you! Situated only five miles from Lihue Airport sits this wonderful vacation get-away within the Kauai Beach Villas.This...
This townhouse is a 2 bedroom(s), 2 bathrooms, located in Koloa, HI.
Explore our airy and roomy Royal Palm unit, which is situated in the midst of verdant tropical landscaping and measures 1550 square feet in size. The pure white sands of Poipu Beach are within a five-minute stroll. Luxurious deep tub in the master bathroom, a...
2 BR Kihei Oceanfront Vacation Home - Sleeps 6
Welcome to our exquisite oceanfront home, where you can indulge in breathtaking, uninterrupted 180° views of the Pacific Ocean. This private sanctuary offers a truly unique experience, as you will have exclusive access to your own sandy entrance leading directly to the...
Spacious Cliffs Condo with Beach Gear & Ocean View
BEDROOMBedroom: King bed, dresser + closet, connecting bath, lanai w/seating for 2. Room darkening curtains, full length mirrors, mini-fridge, 55” smart TV.Our memory foam mattresses are medium firm with a 1.5" quilted top panel and multiple layers of memory foam,...
The Ishihara Home- Classic Quality!
TVNC-1317 TA-150-219-3664-01Recently refreshed and decorated, this executive style plantation home features fascinating exotic wood finishes with the feeling of home from days past. You will never tire of the expansive jaw dropping Waimea Valley and Ocean Views. Most of...
Hale Kaheka 6596, Oceanfront Private Home and Ohana with a Pool and A/C
Located along the iconic Ali'i Dr., this oceanfront home has privacy and world class amenities. Upon driving into the gate, you will be greeted with unobstructed ocean views. Take a ride down the slide into the pool. Or jump in the spa to relax from a long day of...
Rare Ground Floor Ocean Front, best at Maui Sunset
Ocean front! Ground Floor! B-122 is the closest 2 bedroom to the ocean. Best location and your living area is the 10 acres of manicured lawns and gardens just steps from the large "L" shaped swimming pool of Maui Sunset. Large private condominium apartment at the resort...
Newly renovated Oceanfront Condo! Incredible Sunsets, Endless Views
Hawaii Tax #172-837-0688-01Welcome to Sugar Beach #521. Your Hawaiian paradise -- and your home away from home.Your condo rests peacefully on the 5th floor of one of Maui's best resorts, Sugar Beach. From the spacious lanai (patio), you will gaze upon 4.5 miles of...
NEW - Wailea Getaway - steps to great pool & beach
Summary:Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Our Wailea Ekahi Villa is a spacious and private home away from home that makes you feel far from it all yet is still close to everything!Situated above what is widely...
Ground-Floor Condo w/Shared Hot Tub, Pool, Gym, Central A/C, Free WiFi, Patio
Waikoloa Fairway Villas H3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this wonderful spot in the Fairway Villas. As you can see, this is an easy and convenient...
Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates
Wish You Were Here – Turtle Bay Condo | Stylish, Spacious + Steps to your next Adventure..Escape to Oahu’s legendary North Shore and stay in this beautifully updated 2-bedroom, 2-bath ground-floor condo at Turtle Bay Resort, with a bonus loft and room for the whole...
Pali Ke Kua 106, Fabulous view near a bluffs edge
Near the edge of a bluff overlooking the ocean, this special condominium is a favorite with many guests who return each year. Comments in the guest book reflect how much they enjoy vacationing here in their "home away from home" and some have even said that this end...
Quiet, Licensed, Clean & Affordable Cottage Studio with Kitchenette
This charming, affordable, and clean little unit is one of the few free-standing units within the Paniolo Complex. It is situated in a quieter area, as it faces the Prince Golf Course rather than the street. Being a single-level unit, there are no neighbors above to...
Cliffs 6-306 with Extraordinary views of the ocean and lush foliage
From the moment you enter The Cliffs 6306 and see the breathtaking ocean front view, you will feel the stress melting away. Perched on a bluff above the beautiful Pacific Ocean, this spacious corner unit with 18-foot floor-to-ceiling windows and two lanais offers...
Home Sweet Home
Stay in this Charming, Quiet & Private, 2 Bed/2 Bath Home Near Beaches and Adventure!This lovely 2 bedroom/ 2 bath home is ready for you and your family! You will love the fully equipped kitchen with granite counter tops, full range stove, microwave, coffee maker,...
🏖️Close to Complex Amenities | Ground Floor | Nice Unit | vrKCV
vrKCV - Casa de Emdeko 109, Professionally Managed by Kona Coast VacationsWelcome to Casa De Emdeko 109 – Your Ideal Garden View Getaway for Couples or Families!Nestled on historic Ali'i Drive in Kailua-Kona, Casa De Emdeko offers a perfect combination of comfort and...
Hale Kamaole 271 Second floor condo, easy access to best beach on Maui!
This Maui condo rental, has two bedroom’s plus a sleeping loft featuring Ocean, garden, and pool views ! Master bedroom has king bed. Unit has flat screen TVs & Blue-ray players in both bedrooms, a large flat screen/Blu-ray player in living room area. This unit has 3...
Kai Nalu: Spacious Beachfront Home in Waimea
Kai Nalu, which means "Ocean Wave" in Hawaiian, is right on the beach in Waimea, between the river and the historic Waimea Pier. Located on the sunny West side of Kauai, this spacious home provides a perfect setting for your holiday in paradise. Enjoy spectacular ocean...
Tropical Vacation Home in Hawaiian Beaches, Pahoa, HI
We have an amazing Hale for your tropical paradise getaway. This clean, quaint, tropical getaway is in the perfect location to explore the East side of Hawaii. Whether you enjoy Hiking, Volcano exploring, Water Falls, Snorkeling, Kayaking, or what ever you enjoy, this...
Kalama Terrace P-307 - a charming 3rd-floor walkup near Kam 1 Beach with AC!
Welcome to Kalama Terrace P-307, a charming one-bedroom condo located in the heart of sunny Kihei. A short walk from Kihei's stunning Kamaole I Beach, this tropical retreat is an amazing value – it's clean, beautifully decorated, and has AC, smart ROKU TVs for...
In the Heart of Kauai, Great Location, Steps from the Beach and Shops
We are proud to offer you a clean and modern condo in the heart of Kapaa! This lower unit in Village Manor has just been remodeled and is optimized for the comfort of a family or group of four (up to 4). It has 2 bedrooms that are furnished with a queen bed, the other...
Hale Kona Kai 405 - Find your Beach with Kona Beach Properties
Hale Kona Kai 405 is on the top floor. Flooring was updated in 2025 with engineered wood flooring. Central air conditioning keeps the unit cool and comfortable, especially on those extra warm nights. Updated wifi equipment and settings provide high speed wifi, a...