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.
Two homes on the ocean with a private saltwater pool.
The Cliff House is has two detached structures each with its own full kitchens. The private saltwater pool is on the ocean-side with a large shaded patio. Perfect for large families, co-workers and/or friends to gather in one place but have separate, private living...
Okika Lani: Kealakekua Bay Oceanfront Home & Guest Cottage
'Okika Lani sits at the south end of Kealakekua Bay on a private road with spectacular views of the Pacific Ocean, the Captain Cook Monument, and crescent shaped, white sand Ke'ei Beach. Enter the gate at 'Okika Lani and walk into an inner courtyard of Bamboo Palms,...
Luxury Laie Beachfront Estate w/ Private Pool, Spacious Living & Ocean Access
Welcome to Laie Beachfront Estate by GatherExperience the beauty of Oahu’s North Shore at Laie Beachfront Estate, a luxurious oceanfront retreat where contemporary island design meets timeless comfort. Nestled along a half-mile stretch of soft, swimmable white sand,...
Kaanapali Alii | 371
Kaanapali Alii 3712 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Kaanapali Alii 371 is a premier one-bedroom ocean-view residence with a fully enclosed den that functions as a second bedroom. Located on the seventh floor, this...
Waikiki Sunset 3110
See my other properties #3156864 and #3197017 and #3512192 for more 5-star reviews and to book multiple condos for large groups.Located on a high floor of the Waikiki Sunset with sweeping ocean, coastline, and park views this condo offers enough beds to sleeps 6. 1...
Exquisite Oceanview and Mountainview Home with Private Pool!
This is the vacation you will always remember! Welcome to 'PARADISE POIPU', our little slice of Heaven in Kauai. Indulge your senses in this newly built, 1800 square foot home on Kauai’s SUNNY south shore. If you’re one who has an appreciation for the finer things in...
MAUI OCEAN Beach FRONT AMAZING VIEWS Summer Special 275 nightly
Our beautiful condo is located on the world famous Kaanapali Beach and shores. You can't get any closer to the ocean then the MAUI KAI Resort, the Bldg. Is just feet away with the best snorkeling right outside the front door. As you relax on the lanai, it's easy to...
Luxury Hawaiian Style Condo with A/C, Nihilani 16A
Nihilani 16A is a beautifully decorated 2-bedroom, 2-bath, air conditioned plantation style condo. Set in a lush, garden setting, this spacious, one-story, 1,400-square-foot home is a destination where you can retreat into the relaxed Hawaiian lifestyle in comfort and...
Diamond Head Surf House: Gold Coast Oceanfront Home w/AC & Gorgeous Views
Completely immerse yourself in oceanfront island living at the stunning three-level retreat known as the HLH Team, a spacious 3BR luxury home positioned along Oahu’s coveted Gold Coast between Diamond Head and Waikiki. This monthly rental delivers panoramic shoreline...
Steps to Kamaole beaches/Upgraded kitchen & baths/2 Pools/Tennis/Close to Wailea
This second floor 2 bedroom/2 bath peek-a-boo ocean view condo is your perfect Maui vacation retreat just across the street from beautiful Kamaole III beach park! Maui Kamaole is one of the lowest density projects in South Kihei and features beautiful landscaping, 2...
Spacious 5-Bedroom Oceanview House in Holualoa
This prime location has views of the ocean and coastline while being adjacent to a forest reserve. The custom 2-level home offers 5 bedrooms and 4.5 bathrooms, a cool elevation, and lush green areas. The home is equipped with air conditioning and a dehumidifier in each...
Hyatt Residence Club, Ka'anapali Beach, Oceanfront Resort, Beautiful Villas
Please choose a Friday through Sunday for check-in and enjoy a seven-night stay.Rates are set for Garden/Island View. Ocean view/oceanfront may be available depending on your travel dates. Hyatt Kaanapali's new policy now requires guests to pay a daily resort fee of...
Mermaid’s Lookout WOW the views! Ocean Front, full lanai, heated pool & AC.
Welcome to Mermaid's Lookout! This 2-bedroom efficiency home in Hawaiian Paradise Park is perfect for your escape to paradise. With 1 king and 1 split adjustable king, a deep soaking tub with two shower heads, and all the essentials like AC and WiFi, this stunning...
One-Bedroom Villa in Ocean Front Resort, all amenities and services.
The quoted base rent is in Canadian Dollars, including resort fees. Currently, the currency exchange rate is $1.0 USD = $1.4 CAD! 5% discount rate for the week of March 28-Apr 4!This one-bedroom Villa (840 s.f.) in a huge oceanfront resort is managed by the Westin in...
Ma'alaea Surf Unit E4-2 BR Ground Floor Beachfront Condo, AC, Wi-Fi, Pool, TV
Ma'alaea Surf, Unit E4, is conveniently located on the ground floor, just steps away from the large pool. It was completely remodeled recently. This unit is well furnished, features a full kitchen and a second bedroom and bath. This condo features everything including...
Oceanfront Luxury 1 BR Condominium - Perfect Honeymoon Spot!
Escape to our charming 1-bedroom condo in the heart of Wailuku(Ma'alaea Village), Maui. Nestled just a short walk from the stunning West Maui Mountains, you'll be surrounded by breathtaking natural beauty. Take a leisurely 13-minute stroll to the vibrant Maalaea Harbor,...
❤️PiH❤️ Pineapple Hale ★ Elegant Private ★ Bikes ★Free Hilton Pool & Waterslide Passes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Pineapple Hale at KaMilo is a wonderful 4 bedroom home, part of our Hawaiian Luxury Collection.Pineapple Hale at KaMilo, with updated furnishings (2024) and decor provides a perfect setting for your Hawaii...
TOP Floor-Stunning Ocean Views-Well Equipped-All NEW Furnishings
Book with confidence, this remodeled top floor unit at The Royal Mauian with stunning ocean views. This 2 bedroom, 2 bathroom condo offers an exceptional vacation experience and is fully equipped with everything that you need to have a great vacation. It has been...
Beachfront Paradise North Shore, 4BD, King Beds, AC, Parking.
Escape to paradise in this newly remodeled beach house with panoramic ocean views. Step from the back lanai directly onto the sand. In the summer months, enjoy a private stretch of beach right out front, or take a few steps to the right to a larger, semi-private beach....
Hanalei Bay Oceanfront Spacious Home
Come to the charming town of Hanalei and experience the Jones House, a spacious oceanfront home on spectacular Hanalei Bay. Steps away from the beach with breathtaking views of Hanalei Bay, the Jones House is sure to delight. Swim, surf, sunbathe, and stroll along the...
Hale Hiwa Hiwa By Parrish Kauai - AC & privacy at Wainani village
Hale Hiwa Hiwa or our "Beloved Home" at Wainani is the perfect place to spend a relaxing and pampered vacation on Kauai. Located in a cul-de-sac on Kiahuna Plantation Drive you are centrally located in Poipu and close to shopping, dining and Poipu Beach.Enjoy the...
Modern Charm: Renovated 1BR, fast 600Mbps Wifi, W/D in unit, Stunning Views
Welcome to your island paradise! Soak in floor-to-ceiling mountain views with your morning cup of coffee; at night, savor the vista of twinkling city lights. You’ll love whipping up homecooked meals with the full kitchen, working comfortably with the remote work setup,...
Regency 111 Defines Comfort & Spaciousness. Lovely Furniture & Furnishings
*Completely refurbished corner unit with high ceilings and over 1300 square feet of living space with new and comfortable furniture.*Master bedroom has a King SLEEP NUMBER bed which allows you to adjust the firmness of the mattress.*Twin beds in the second bedroom allow...
Makahuena 5203 - Elima Building: Oceanfront 2BR Condo
Located on the southernmost point of Kauai, this unique oceanfront property is situated on the edge of a bluff providing spectacular views of the blue Pacific and the entire Poipu coastline from each unit. Incredible ocean views are the dominant feature of this resort...
Luxury Condo Waikoloa Beach Resort, Gold Member Golf Package included.
This beautiful luxury 2 bedroom, 2 bath condo comes with amazing golf & pool benefits and is located in the Waikoloa Beach Villas at the Waikoloa Beach Resort. The space: Our beautiful newly remodeled luxury 2 bedroom, 2 bath condo comes with amazing golf & pool...
Lovely 2nd Floor Unit On Golf Course, Easy walk to Beach, Restaurants, Shopping
Located on the beautiful Waikoloa Beach Course, 1st fairway and green with the Petroglyph Trail and Mauna Kea as the backdrop, the second floor unit has two bedrooms with king size beds and options for separate twin beds, an open lanai and generous living space for your...
West Maui Ocean front Condo, Lahaina
Thank you for your interest in our condo. Our condo is outside the fire of 2023 perimeter, but clean-up is still going on and Lahaina Town is closed. Our unit has a King bed, WIRELESS INTERNET and views. Do you need anything else to have a great vacation? Hale Ono Loa,...
Ocean view home on beautiful Sugar/Kihei Beach - PERMIT #STKM 2015/0003
Over 150 glowing reviews and counting. This beachfront gem is the perfect retreat for families, couples, or groups seeking space, comfort, local feel (not touristy) and unbeatable central location.Property Highlights:Spacious 3-bedroom, 2.5-bath home with optional...
4 Bdrm Luxury Golf Course Home with A/C
Welcome to Molokama. Walking distance to a white sand beach through Hanalei Bay Resort in Princeville, Kauai. The home overlooks the Robert Trent Jones designed Makai Golf Course. The 4-bed, 3-bath home sleeps 8 comfortably. 4 bikes, beach gear, outdoor shower. Master...
25% discount now to mid July. Fab Kihei Condo-Across from beach, A/C, Pickleball
Our unit is in Building 9. As we vacation often in our condo, we have furnished it to represent our home away from home. Central air has been installed with units in the living room and both bedrooms. Each room can be controlled to enjoy wonderful, noiseless air...
🏖️AC Included | Gated Community | Pool & Ocean Views | vrKCV
vrKCV - Kamilo Place, Professionally Managed by Kona Coast Vacations Private 4-Bedroom Retreat with Ocean Views, Pool & AC in Gated CommunityEscape to your own island oasis in this luxurious 4-bedroom, 3.5-bathroom vacation home located in the prestigious gated...
Waikoloa Beach Villas O2 - Ground Floor Villa 7th Night Free April-June 2025!
Aloha and Welcome to our beautiful 2 bedroom 2 bath villa with a bbq kitchen on lanai in Waikoloa Beach Villas. Come enjoy the beauty of Hawaii in our perfectly located condo at Waikoloa Beach Villas. Just 20 minutes north of the Kona airport you will find yourself in...
Spacious 4BR Princeville Home -AC, SPA, and Bikes for faster beach access
Welcome to Paradise! Great design for family or friend gatherings in spacious two story home. Fast WiFi, and LG 75" inch OLED Smart TV and Outdoor Shower. Enjoy your vacation or workation with family and friends in a tropically landscaped property with Bali Hai...
Pakala Beach Estate: Island-Style Retreat on Kauai's West Shore
Rates shown are for 8 guests; additional guests up to maximum of 11 are $20/night each. This magnificent, island-style estate truly exceeds all expectations. Located on secluded Pakala's Beach on Kauai's west side, this totally serene property borders an orchard and is...
Gorgeous Oceanfront Studio at Lahaina Shores Beach Resort
Welcome to our oceanfront studio condo located on the 2nd floor of the newly renovated Lahaina Shores Beach Resort. You’ll love the beautiful ocean and sunset views from the lanai (balcony), with occasional whale sightings during Fall and Spring. The studio has a king...
OCEANFRONT to Walking Path & Beach TVNC #1287
$325 per night up to 4 guests. $35 per night for each additional guest. Due to oceanfront location, this unit is located within the Tsunami Evacuation Zone. Honu Hale Kai is a warm and casual home base for your family vacation adventure. This home sits upon an...
Kahana Village #7 Beach Front Luxury
Elegant and luxurious describes our 3 bedroom, 2 bath condo with travertine floors, which makes it the perfect beach house. Our updated ground floor unit faces north with a spectacular view of the ocean and the island of Molokai. It's paces from the beach and overlooks...
Island Touches w/Modern Kitchen, Wood Floors, Lanai, Flat Screen, WiFi–Kaha Lani 203
Castle Kaha Lani Resort #203 - This 739 sq. ft. vacation unit looks out over our resort. Unit 203 features relaxing tropical décor along with convenient touches such as a full kitchen with dishwasher, ceiling fans, dining area, flat screen TV, and WiFi. Sleeps 4 in 1...
Tropical Oasis Studio in Ko Olina Beach Resort - 30 Day Rental
**Note: This property cannot be rented for less than 30 consecutive days. Rental prices will not be adjusted based on the number of days the rental is actually used or occupied.**Prime Location!** Nestled within the prestigious Coconut Plantation community of Ko Olina...
North shore Maui B and B room 1.
Holomakai B and B is a vacation rental with three bedrooms for rent individually on Maui’s north shore. Each room is on a separate floor with a private bathroom, ac, tv and Wi-Fi. The rest of the house, the entrance, fully equipped kitchen, living room and spacious...
Fully Renovated Corner Unit a Block to Waikiki Beach! Parking, AC, Wi-Fi
Ni'ihau Apartments #305 – 247 Beach WalkLocation, location, location! Ni'ihau is a hidden gem found within the hustle and bustle of Waikiki just a block away from world-famous Waikiki Beach where surfers and paddlers spend their days! This beautiful corner unit (673...
Kaanapali Alii | 383
Kaanapali Alii 3832 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 383, a beautifully renovated two-bedroom ocean-view residence that serves as the perfect gathering place for your Hawaiian getaway. The...
Spacious1bed Ocean View Pool Beach Access Tennis Pickle Ball Air Conditioning!!
Our spacious 1bed, 1 bath condo is the perfect place to unwind after a long day of adventuring around this beautiful island. Relax on the lanai with a tropical drink in your hand while watching the beautiful sunset.*3 min walk to swimmable beaches & restaurants*10 min...
Luxury Villa at Mauna Kea w/Private Pool, Stunning Coastal Views & AC: Villa 21
This newly renovated ground-level villa in Kamuela offers the best of Big Island living. With panoramic views of the Pacific, Maui in the distance, and the lush greens of Mauna Kea’s championship course, this four-bedroom retreat is designed for families, couples, and...
The Maui Moon Oceanfront Condo- Perfect for couples!
Voted as one of the top 25 islands in the world 2020 by Travel and Leisure magazine. Maui is truly the garden paradise for your hard earned Hawaiian Vacation. Aloha and welcome to the Maui Moon Condo in the Menehune Shores oceanfront complex in low key Kihei located on...
Hilton Hawaiian Village Rental
We are please to provide our Suite units by Hilton Grand Vacations. The resort gives guests ideal access to the best stretch of Waikiki's famous white-sand beach and the extensive entertainment, shopping and dining options within the renowned Hilton Hawaiian...
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
Perfect Kailua Home on 18,000 square feet of land all your own!! Lots of room to spread out!! We have a gorgeous newly tiled Swimming Pool and spa! You are invited to rest and relax in “Ka Hale Lai” , Kailua’s House of Serenity, 5 minutes to the beach, and a short drive...
Steps from waves - Ground Floor - Direct Ocean Front condo -full AC & King bed
Our well-appointed, ground floor, completely remodeled condo is waiting to welcome you in to RELAX. The breathtaking ocean view straight out onto the waves will thrill you the moment you enter into our home. "WOW!!" As our guests, we are confident that you will love it...
KoOlina Beach Club Oceanfront Resort
Please choose a Friday through Sunday check-in for a 7 night stay. Thank you for your interest in booking with Dash Realty Group, Windermere Florida. Dash Realty Group is registered in Florida as a licensed Fla. Seller of Travel Ref. No. ST42435.Rates are set for...
Ocean&Mountain View Paradise - 3BD2BAParking CONTACT HOST FOR LENGTH OF STAY?'s
North East Shore Hawaiian Paradise: This property is located in the perfect spot on the North East Shore with gorgeous views of the ocean. It's the perfect getaway for you and your family. Ka'a'awa Kasa is a tranquil escape for guests looking to unwind. Located at the...