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.
![Sleep to Surf Sounds & Trade Winds [or AC!] While Enjoying Your Oceanfront Home.](https://media.vrbo.com/lodging/19000000/18960000/18955800/18955754/5f6c3ef4.jpg?impolicy=ccrop&w=1000&h=666&q=medium)
Sleep to Surf Sounds & Trade Winds [or AC!] While Enjoying Your Oceanfront Home.
Our comfortable, fourth-floor, south shore condo is right ON the ocean so you will SEE --and HEAR-- the sound of the surf as soon as you open your front door. The condo, with stylish, contemporary furniture, boasts a comfortable king-size bed. Relax "at home" and enjoy...
Kona coffee farm retreat, with full ocean views near Kailua Kona!
Escape to a lush and secluded mountain retreat Kona coffee farm, just minutes away from sun-kissed beaches, Kailua and Captain Cook. Enjoy picturesque sunsets and stargaze at night. Relax in peaceful moments surrounded by full ocean views, exotic flowers, coffee trees...
Beautiful Ocean/Resort View Villa- in Ka'anapali: Westin Nanea-2 bd 2 ba
Hi! Please "INQUIRE" about a reservation you are interested in. Inventory is always in flux. I can reserve most dates 8-12 months out, but not always. Anything less than 8 months is hit and miss depending on the month you are interested in going. But I am always happy...
Maui Resort Rentals: Westin Nanea Villas 2BR Oceanfront Villa
2 Bedroom Oceanfront Villa at Ka'anapali's Newest Luxury Beachfront Resort! Located on 16 prime beachfront acres on Ka’anapali North Beach, The Westin Nanea Villas is Kaanapali’s newest beachfront resort. The resort features 390 elegantly appointed 1, 2, and 3...
Lae Nani Condo 317
Paradise awaits you in this beautiful ground floor, one-bedroom, two-full-bath Lae Nani Condo, Unit #317 on the beautiful Garden Isle of Kauai!Located on Kauai’s beautiful Coconut Coast (East side), this Condo has all the amenities you would ever need for a restful...
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
ON SALE 10/25 TO 11/1/25 TAKE 20% OFF Beachfront Wailea: Ocean Panoramic & Outer Island Views, Penthouse K-208, 4 Full Bedrooms & 3 Full Baths; Total 3892 S.F. READ ALL OUR REVIEWS for YOUR BEST INSIGHTS, PLEASE.The Wailea Beach Villas Finest Upgrades. Complete...
Maui Resort Rentals: Honua Kai Hokulani 814 - Top Floor 1BR w/ Partial Ocean & Mountain Views!
This beautifully appointed top floor "penthouse" suite boasts one of the best one-bedroom locations available at Honua Kai. Enjoy generous partial ocean views from the balcony and primary bedroom in addition to great views of the verdant West Maui Mountains. This suite...
Stunning Ocean View In Luxury Home In Keauhou Estates
Enjoy spectacular 180-degree ocean views from this 3 bedroom, 3700 square foot luxury home in Keauhou Estates on the Big Island of Hawaii. The house has an open floor plan, marble floors throughout most of the main living spaces, and large rooms with tasteful and...
Kiahuna Paradise condo with A/C
Kiahuna plantation unit 120 in Building 18.You are very short walk away from a beach, actually 200 steps.On ground floor. Poipu beach is very near.Welcome to Kiahuna Plantation on the sunny south shore of Kauai! This newly remodeled 1 bedroom 1 bathroom Kiahuna...
Luxury Living in Allure Waikiki with Free Parking
Indulge in an elegant and spacious 1 bed 1 bath plus powder room with large balcony luxury condo unit in the prestigious Allure Waikiki. The unit is conveniently located at the edge of Waikiki. A premiere destination for world class shopping on Kalakaua Avenue's luxury...
Absolute Oceanfront on Ancient Lava Cliffs! Whales, dolphins, turtles!
Swap the daily grind for luxurious absolute oceanfront tranquility with an escape to Paradise Breeze Retreat in Keaau, Hawaii. Only a 25 minute drive from Hilo Airport but a world away from stress. Stunning panoramic oceanfront views from every room and the audible...
Cute Seaview Studio! Steps from Kamaole 2 Beach & Pool 🌺 Maui Banyan Resort
Relax in our cute studio apartment at the Maui Banyan Resort, just a few steps from the gentle, sandy shores. Take in glimpses of the ocean from the lanai and embrace the aloha spirit.✓ Right across the street from Kamaole Beach II✓ Kitchenette w/ microwave + fridge...
Ocean View - 1 Bedroom - Hyatt Ka'anapali Beach - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using...
Luxury 2 bedroom in Waikiki!
Welcome! We hope you enjoy the newly renovated and spacious 2 bedroom/2 bathroom. This high-floor unit has an amazing wrap-up lanai deck featuring 180 views of Diamond Head, the ocean, the mountains, the sunrise, sunset, and metro Honolulu. You’ll be a 10-minute walk...
Large 3-bedroom condo in Kona Coast Resort with AC, WiFi, fitness room - NEW!
Kona Coast Resort #1-301 is a 3 bedroom, 2 bath condo with fantastic ocean views and all of the amazing amenities of a 5-Star Resort! Enjoy two swimming pools, three spas, a sauna, a playground, tennis/pickle-ball courts, volleyball courts, and two fitness centers.Relax...
Ocean Front Condo at Kanai A Nalu
WELCOME to Our Beautiful Ocean Front Condo at Kanai A Nalu, on the quiet side of Maui. Our ocean front unit, located on the third floor overlooks the grounds Lush Tropical Garden as well as the Crystal Blue Waters of Maalaea Bay. Kanai A Nalu is a beautiful beachfront...
Alihi Lani 6: Ocean Front 2 bedroom 2 bath!! Air Conditioned!!
May we welcome you to Alihi Lani at Poipu. Our beautiful air conditioned condo located in the heart of Kauai's sunny south shore! Alihi Lani. or 'Beautiful Horizon Views', aptly describes the magnificent ocean panorama of Hawaiian sunsets, majestic whales, local...
New Listing! Free Night at Kahana Sunset E5E – Remodeled Corner Unit with AC
This property is not currently affected by the recent proposed legislation.Summer Deals! Book 5nights get the 6th night free, or complimentary Early or Late checkout!Welcome to your perfect Maui escape! Located in the peaceful Kahana area, this bright and breezy...
Nicely upgraded 2bd oceanfront resort condo
Kaanapali Shores 513 is a 2-bedroom, 2-bathroom condo with central air conditioning that can accommodate up to 6 guests. Located on the fifth floor, inside you will find an open-concept layout and Hawaiian-inspired decor with a sense of island serenity. When it's time...
❤️PiH❤️ PARADISE AWAITS ★ Private Pool & Spa ★ Guest Cottage
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Paradise Awaits, a part of our Hawaiian Luxury Collection. Paradise Awaits at KaMilo is a wonderful, large, single-level 4 bedroom home that includes three bedrooms in the main house, each with a large primary...
Welcome to Luana Villa 9D Oceanfront Resort , Upstairs, Mountain/Pool view
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful upper level Luana Villa at the Honua Kai Resort.This luxurious villa is located within the 38 family-friendly acres of the Honua Kai Resort & Spa, designed with relaxation and memory-making in mind,...
Christmas on Maui! Available Dec. 21-December 28
The Hyatt Residence Club is a luxury ocean front resort on the south end of Kaanapali Beach, blending the best features of a deluxe condominium with the most popular amenities of a luxury hotel.Enjoy a guaranteed 2BR/2BA ocean front villa, featuring floor-to-ceiling...
Experience luxury near golf courses, 4 mins to Four Seasons Resort
STVR-19-357988 https://tours.spaces.808.com/1759448 Luxury living can be found at this spectacular 4 bedroom, 4.5 bath, resort home. Located within the Four Seasons Resort Hualalai on the Big Island of Hawaii. The gourmet kitchen is fully equipped with high-end...
ICC 18 Remodeled Cottage w Pool AC Beach
International Colony Club 18 Beautifully Remodeled Air Conditioned Hawaiian Plantation Style Cottage Across the Street from the Beach FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch...
Ocean Views | Steps to Sandy Beach | Kam 5-205
Welcome to Kamaole Sands 5-205, a rare single-level 2-bedroom, 2-bathroom haven just steps from world-famous Kamaole Beach III. This beautifully updated vacation retreat features a spacious open floor plan with modern amenities, including a fully renovated kitchen with...
View of Mauna Kea in Gated Community across from Golf Course
Quiet & Private 1 King bed/1 Twin daybed/1 bath kitchenette (attached to main house) w/ separate entrance & patio ~600 sqft in secluded & gated community at a cool 2400 ft elevation. Wake up to beautiful views of Mauna Kea. Located 30 min by car from Kona Airport,...
Aloha Villas # 4, Luxury Oceanfront Townhouse, Steps to Beach
Imagine this: stepping off the plane and into paradise at Aloha Villas, a beachfront complex in South Maui. Eha Villa, your home away from home, offers a luxurious two-story townhouse experience, perfect for families or groups.Unwind in Spacious ComfortSpread out over...
Ocean View Cottage with Separate Suite
Incredible COTTAGE! with a new Separate Suite! How can you vacation in Hawaii and not have an ocean view!! Authentic Hawaii vacation retreat in Hawaii Kai-East Side of Oahu! Get away from the hustle and bustle of everyday day life, rejuvenate, and revitalize yourself at...
Top-Floor Mana Kai 814: Stunning Ocean Views, Sunsets, and Whale Watching!
Stay 5 Nights, Get 1 Free – More Time to RelaxEnjoy an extra night on us! Book 5 consecutive nights, and we’ll give you the 6th night free—a perfect way to extend your getaway without extra cost.Limited availability: This offer is not valid during peak travel...
Hulili Tropical Fruit Farm - Pineapple Cottage
Opened for guests in 2010, the original HULILI FARM COTTAGE (pronounced who-lee-lee) has welcomed so many wonderful guests that it became time to enable more people to enjoy the farm. Introducing Pineapple Cottage! Please check out our reviews for the original cottage...
Beautiful Stylish Condo W/ Amazing Ocean Views, Walk To World Class Beach!
***Professionally Cleaned Condo, No-Contact Check-In/Check Out***Welcome to Kamaole Beach Royale #310, located in the heart of Kihei, Maui!. Enjoy a spectacular views of the ocean, beaches and neighboring islands in this recently remodeled condo!This condo has just been...
Wai'ula'ula I101 - Designer Residence
This corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living and 52 inch plasma TV, a chefs' kitchen outfitted with Wolf and Sub-Zero appliances/gas range, king beds in each bedroom (1 bed can be...
Beachfront on Kaanapali Mahana 1106!
SPECTACULAR 11TH FLOOR OCEAN FRONT MAHANA 1106! KAANAPALI BEACH, A/CWelcome to Mahana 1106! Located on the eleventh-floor, this one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands from the living room,...
Ho'omaika'i
This newly renovated, well-stocked two-bedroom, two bathrooms with loft space is fantastic getaway and a convenient, clean space for you home away from home with your family or friends. You can enjoy all that the North Shore has to offer and then come home to a...
Wailea Ekolu Village | 1007
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
Spectacular Oceanfront Home! Watch turtles from deck while relaxing in the spa!!
Located on Maui's South Shore in the heart of beautiful Makena Bay, this single story oceanfront cottage is an island paradise. Built over 60 years ago and recently remodeled, guests are provided with all the modern conveniences for an incredible vacation. We recently...
Spectacular Views of Hanalei Bay and Bali Hai 3 bedroom
Kauai’s Most Breathtaking Views at Hanalei Bay ResortWelcome to our North Shore paradise. Unit 9201/9202/9203 is located in the renowned Bamboo building which features the most stunning views of Hanalei Bay and Bali Hai. This property is a spacious 1750 square foot...
PUAKO 1940's Vintage Beach Cottage - Now with Air Conditioning
Immerse yourself in paradise at our tranquil completely restored vintage beach cottage. We're located in Puako, the only beachfront community on the Kohala coast on the Big Island of Hawaii.Puako was an ancient fishing village and is now known for its green sea turtles,...
BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C
Dream your most desired vacation. Then come to magical Maui, one of the world’s most elite vacation destinations. How better to experience our island than by renting from an owner who has combined her own personal getaway with the conveniences of home and the...
Charming Hanalei Bungalow A/C Walk to Town and Hanalei Bay Beach! TVNC-5096
Mana Kauai Island Vacations present the charming Umetsu Cottage! Welcome to our idyllic one bedroom, one and a half bath cottage at the Hanalei Bay. This remodeled beach cottage reflects the era of Old Hawaii. Located steps from the iconic Hanalei Bay and a short stroll...
Gorgeous Luxury Estate Home - Hualalai Resort - Spectacular Ocean and Golf Course Views - Private Pool and Spa - 3 Golf Carts Included
Gorgeous, Contemporary, Newer Home Exemplifies Luxury and ease of Living in our Island Paradise. This 5-bedroom, 5 1/2 bath pod-style estate home is exceptionally appointed and designed to take full advantage of the temperate climate and island breezes.Upon arrival to...
Garden view dining on your spacious lanai
Maui Kaanapali Villas A210 is a 1-bedroom, 1-bathroom condo that is located on the 2nd floor of the Aloha Tower. This unit offers central AC, flat-screen TVs, and tropical views and can accommodate up to 4 guests. The bedroom opens to the living room and offers a...
Ocean Front, Walking Distance to 3 Pristine Beaches - Kapalua Bay Villa #20B3
Experience unparalleled ocean and white sand beach views from every room in Kapalua Bay Villa 20B3. Designed to accommodate 2 guests in absolute luxury, this one-bedroom, one-and-a-half bathroom oceanfront villa epitomizes paradise. Its prime building location next to...
Palms at Wailea Villa 806 Ocean View 2BD 2BA
- 2nd floor, walk-up unit- Renovated Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- Guest bedroom with 1 queen bed- Queen sofa bed...
Lua Hoana - 3-BD Home with Ocean Views and Hot Tub
Welcome to your tropical paradise! This A-frame cedar cabin offers a stunning backdrop to your island vacation. With 3 comfortable bedrooms (including one with a private balcony) and plenty of outdoor space, there’s no shortage of room to relax. Enjoy ocean views from...
PARADISE PROMISED! Spacious 6 bedroom home. Minimum Stay
This property will only be made available once every 30 days to comply with the Hawaii rental laws. Rental contracts will reflect a 30 day rental period and no other guests may occupy the home during that time period. Please contact us for further information prior to...
Kona Lighthouse Hawaii - FAMILY BEACH HOUSE
The Kona Lighthouse is centrally located in a peaceful neighborhood along the Gold Coast of the Big Island, a 5-mile scenic, oceanfront drive between the towns of Kailua-Kona and Keauhou-Kona. —- Ideal for family and small group vacations. A block from White Sands...
One Ocean Mauna Lani Golf Estate 4 with Infinity Pool & Spa
Welcome to 6BD Mauna Lani Lux Golf Estate (4) at One Ocean, a brand-new luxurious six-bedroom, six-and-a-half bathroom home built in 2024 nestled in the prestigious Mauna Lani Resort area in Waimea, Hawaii. Perfect for large families or groups of up to ten guests, this...
RENOVATED 10/21! Corner Oceanview Condo w/ AC!!
Our recently remodeled 1 bed, 1 bath home is located on the second floor, so you’ll enjoy more privacy in your home-away-from-home. Being in the corner also gives us breath-taking views of the Pacific Ocean. During whale season, you’ll also see whales breaching from...
119 night April disc Alii Dr Fully Equipped, Pool, Jacuzzi, BBQ, High-Speed WiFi
Welcome to Kona Bali Kai Ocean and Surf location! Your dream vacation awaits at our beautiful condo located in a prime spot close to downtown, Magic Sands Beach, and Kahalu'u Bay. Picture yourself opening the slider and listening to the soothing waves at night. Our...