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.
Private cottage above Kona surrounded by coffee farms.
Experience living in Hawaii lush garden property. Very private fully remodeled 1bed/1bath cottage on 2 acre property in Holualoa, just above Kailua Kona. Cooler elevation, surrounded by coffee farms. Hike to a famous Kona Coffee farms like : Heavenly Hawaiian and...
Charming 2-bedroom near the beach with AC, WiFi, Yoga, Surf, Golf
Consider this unique stay your home away from home while you visit Ewa Beach. Our unit is located upstairs with a private entrance. This cool property features 2 bedrooms with a queen bed and a full bed, along with a cozy living room with a sofa bed for extra guests....
Seaside Serenity in Hawaii
About this spaceDiscover our island oasis in Koloa!, Hawaii Nestled in a tranquil and tropical paradise, our upgraded unit at Kiahuna Plantation Resort (Unit 434) offers modern comforts like a new AC, plush mattress, and cozy couch. A short stroll through lush grounds...
Kona Condo at Magic Sands Beach-Ocean Views-Top Floor-Quiet
Aloha and welcome to our condo at White Sands Village. Brand new to the rental market, this wonderfully appointed 2-bedroom, 2-bathroom top floor condo offers everything you’ll need to enjoy your stay in Kailua-Kona and the Big Island Of Hawaii. This newly upgraded...
❤️PiH❤️ Sunset Villa ♥ Families ★ 3 Master Ensuites ★ Luxury Home with Bikes ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sunset Villa, a part of our Hawaiian Luxury Collection. Sunset Villa at Mauna Lani Villages is a wonderful 3 bedroom home with luxurious high end finishes in a premier resort community. This is one of a very...
Wailea Grand Champions 71 - 2 Bedroom Golf Course & Partial Ocean View
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views from the living room and private lanai. This spacious two-bedroom, two-bath condo comfortably accommodates up to six guests, providing ample room for...
Maui Sunset A415: 1 BR, 2 BA Condominium in Kihei, Sleeps 5
Condo rental on the beach in sunny Maui, Hawaii. Condo A415 has one of the best locations for views of the ocean and Maui vistas.Great location, one bedroom two bath ocean view. Watch the life of Maui unfold from the morning till evening from your private 114 sq foot...
Ho’okipa Hideaway - North Shore, Walk to Cafe
This North Shore Maui Hideaway has its own private entrance, a charming private garden, cozy queen bed and off-street parking for one car. An attached covered and enclosed screened porch with two overstuffed lounge chairs looks out onto the beautiful private and gated...
Modern and Relaxing Oceanfront Vistas
Summary:Bright, modern, and spacious. Complete remodel in May 2022! Thoughtfully designed to elevate your experience with us. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in the sunny and vibrant...
Beautiful BeachFront condo Oceanview
Welcome to our luxurious Maalaea, Ocean & Beachfront newly remodeled 2 bedroom, 2 bathroom Condo. Kanai A Nalu is one of 8 complexes on our quite street. This lovely unit is situated on famous “Sugar Beach”, a beautiful and quiet white sands beach that stretches for...
New Bathrooms! Modern Spacious Penthouse Oceanview
Indulge in the allure of a stunning ocean-view penthouse nestled within the renowned Kamaole Sands Resort, accommodating up to eight guests comfortably. Ideal for families or travel parties. Enjoy enticing amenities like the spacious pool, hot tub, let the little ones...
'Best Vacation Ever' Say Our Guests! Special May Rates
You will love this luxurious, air conditioned, two bedroom, two bath, 1300 square foot Villa! Fully furnished, with its own spacious, private dining lanai, this unit was completely remodeled in 2020. It is immaculate, impeccably maintained and cleaned to the highest...
Luxury at its Best with Big Ocean Views!!
Aloha & welcome to the Wailea Diamond Suite at Ekolu Village #305!The moment you step through the door you’ll know you’ve come home to luxury in this elegant 2 bedroom, 2 bath condo. Each bedroom features its own unique bath, private lanai sanctuary, ambient...
Turtle Bay Hideaway - Kuilima Estates East
Our Turtle Bay Hideaway is the perfect place for your Hawaiian getaway! Enjoy 5 miles+ of secluded beaches, 2 private swimming pools, 2 private tennis courts, 2 PGA golf courses, horseback riding, surfing, snorkeling, diving, fishing, activity rentals and fine dining...
Sun, Sand And Surf …….. A Romantic Couple’s Getaway…… Hale Ono Loa 306 --
Our unit has an incredible 3rd floor oceanfront view of our neighboring island, Lana’i. Enjoy the sounds of the surf while watching turtles and whales from the shoreline or your private lanai. The complex provides a relaxing sundeck and pool with beautiful floral...
ON THE SAND! Chuns Reef Beach House - Oceanfront Main House - A/C - Beach Toys
****Please note this property may not be rented for less than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied. Please inquire regarding availability for stays from 5 to 30 days.Chuns...
Breathtaking Ocean Front Views. Incredible Reviews.
Unit 516 is a stunning fifth-floor penthouse with unobstructed ocean views of Molokini, Kahoʻolawe, Lānaʻi, and the West Maui Mountains. Perched above the palms with a spacious ocean-facing lanai, this is your ideal base for sunsets, turtle-watching, whale season, or...
Tropical Retreat in Paradise-steps from the Ocean! Newly remodeled with A/C.
Beautifully remodeled ground floor corner unit in Building 20, with Pacific Ocean views! From the front Lanai, there is a broad green lawn, lined with palm trees that take you to one of the most beautiful swimming and surfing beaches in the world. Our one bedroom, first...
STUNNING OCEANFRONT * Poipu's Best View * New Air Conditioning throughout
Words cannot describe the incredible view from this penthouse condo. It's mesmerizing!! You'll hear the waves crash below you along the coastline and marvel at the Pacific Ocean stretching out as far as you can see. Turtles, spinner dolphins, and whales are often...
Two-story ocean view home with a furnished patio & deck, washer/dryer, & AC
Ka Hale me Ka ike 30 Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in the amazing view from both inside and out at this four-bedroom, family-friendly retreat here...
Our Place of Joy: An Ocean Retreat
Length of stay: MINIMUM 30 NIGHTS. Monthly rental. Property damage insurance required.Kai Lani is a quiet gated community located in Ko Olina, a 640 acre oceanfront resort on West Oahu, the dry leeward side of the island. Ko Olina means 'Place of Joy,’ where the aloha...
NEW - THE OUTRIGGER 3BR 2Bath - Hilo cold AC
Welcome to The Outrigger!! You will love our 3BR 2Bathroom Home super central located in Downtown Hilo. Our home is well equipped and ready to be discovered by you your family and friends! We have ceiling fans in every room and AC`s in each Bedroom. Total of two...
Air Conditioned 2 Bedrooms 1 Bath Apartment, fine decorated, Free Laundry in HPP
Built in 2022!This is a 2-bed, 1-bath apartment with a separate kitchen and dining area, has air conditioners in both bedrooms, located on a one-acre land harboring the most unique feature of Hawaii Paradise Park in Keaau, offering a real retreat from the busy world....
Maile Treehouse in Volcano, Hawaii is "Magical!"
Welcome to Maile Treehouse this lovely vacation rental with views of the forest in Volcano, Hawaii on the lush Big Island. Tucked into a quiet neighborhood right in Volcano Village you are a few minutes drive to Volcanoes National Park and several excellent restaurants....
The Reef House in Puako: 2 BR Oceanfront Home and Cottage
Your oceanfront authentic Hawaii vacation destination awaits you! The Reef House is a perfect place to get away from it all. With breathtaking views, a paradise of snorkeling at your back door and a lush tropical yard to relax in and soak it all in. Ideally located,...
Hualalai Hillside Villa 3101 - Prime Location~Ocean Views!
This fabulous 3 bedroom, 2.5 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the amazing ocean views from this ground floor Hillside Villa. Koa cabinets, travertine floors and wooden privacy...
Newly Remodeled, Ocean View, Beachfront Paradise at Lae Nani
Lae Nani Condo unit 435 is a 2-bedroom, 2-bathroom Penthouse unit with two ocean view lanais from the main living area and the master bedroom suite. Our remodel in late Spring 2024 included a full kitchen remodel, new flooring throughout and an update to both bathrooms....
Ocean View! Lagoon Tower! Family Friendly Resort! Beautiful Hilton Condo On Waikiki Beach!
Set along the breezy coastline of Honolulu, and with all the comforts of home. You will have access to four swimming pools, one with multiple waterslides, a saltwater recreation lagoon, daily planned family activities, Waikiki Beach access, water sports, spa...
Side by side penthouse suites with Central Air and unencumbered Ocean Views
* 10% Discount November 1st thru December 17, 2025.Penthouse enjoys the best location at the Kona Coast Resort, and is situated steps away from the Kona Coast Resort’s main pool, large jetted spa, restaurant, exercise facility, check-in office, and concierge...
Hallor House: Breezy Hideaway Near Tunnels & Na Pali Trail
Discover the serene charm of Hallor House TVNC #5147, nestled in the tropical beauty of Hanalei, HI. This inviting vacation home offers 1,158 square feet of thoughtfully designed space, perfect for families and friends seeking an authentic island experience.**What...
Pinnacle at Poipu - Luxury Estate w/ Ocean Views and Salt Water Oasis Pool!
Introducing the Pinnacle of Poipu: A Magical and Exquisite Getaway on the Garden Isle. Elevate your vacation experience at this exclusive luxury vacation rental nestled in the heart of Poipu, Kaua'i. Perched high atop its picturesque surroundings. A true masterpiece...
Paradise + Turtles!
Our beautiful and spacious Kona home is just a 2 minute drive or 10 minute walk to the world famous Kahalu'u beach park where swimming with Turtles is virtually guaranteed. While you are a guest in a privately owned Condominium the property has resort-amenities such as...
Gorgeous 2b w/ ocean view, tastefully renovated, great location.
Welcome to your Kona retreat at White Sands Village, Unit 307 – a stylish top-floor condo with rare no-stairs access and a comfortable layout that makes it ideal for families, couples, or friends traveling together. Just steps across the street from Magic Sands Beach,...
Gorgeous Poipu Villa with Pool & Spa
Arriving at this stunning custom ocean view Kukui‘ula residence is an exercise in tranquility. A passage across the welcoming water feature and through the custom mahogany front doors unveils a framed view full of Kaua‘i’s colorful landscape, mountains and...
Milo Maui County permit STPH 20130018
4 bedroom, two bathroom, oceanfront cottage, sleeps 8, one rental group at a time. Relax in this charming 2 story house or under the palm trees. Enjoy the surf or nearby swimming beach. Minutes away from world famous Ho'okipa Beach Park and Paia Bay.The property has the...
Entire Cottage w/ Private Plunge Pool, A/C, BBQ
Air Conditioning is in the living room and principal bedroom. Guest bedroom has a ceiling fan only. A private freestanding cottage with its own Private Heated Plunge Pool. Air Conditioning, a rare amenity on Kaua'i, cools the space for a restorative nights sleep. Relax...
Wailea Grand Champions 73 - 1 Bedroom Partial Ocean View Condo
Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, and stunning views in the heart of Wailea, Maui. As you enter the villa, you\'re greeted by a bright and spacious great room, ideal for relaxation...
Maui Resort Rentals: Hokulani 505 – 5th Floor, Closest 2BR Column to the Beach, Superb Ocean Views!
Recently upgraded, Hokulani 505 boasts an incredible 5th-floor interior courtyard location in the closest two bedroom column to the ocean at the entire resort. Due to its premier vantage point, Hokulani 505 is one of the few two-bedroom suites at Honua Kai offering...
ONLY $129 ...... LUXURY CONDO SPECIAL ***TOTAL REMODEL*** Bldg 1
OCEAN VIEWBOOK WITH US TODAY! BEST REMODEL in MAUI VISTACompletely gutted with NEW EVERYTHING!!!Tigerwood Hardwood Floors, Italian Tile, Travertine, Fresh Paint, Ceiling Fans, All New Furniture, New Mattress and Box Spring, Bed Linens, Towels, Custom Cabinets, Stainless...
Banyan Tree 301: DIRECT OCEANFRONT 2/2 REMODELED WITH AIR CONDITIONING!
WOW! That's what you'll say when walking into Banyan Tree, Unit#301, a third floor fully remodeled condo in a secure and private building with an elevator, pool, spa and barbecue! You'll find floor to ceiling glass showcasing the beautiful ocean almost at your feet! ! A...
Maui Resort Rentals: Honua Kai Hokulani 837 - Stunning 8th Floor Ocean View Studio
This spacious oceanview studio provides awe-inspiring views of the Pacific Ocean and Maui's neighbor island Lanai from its prime 8th-floor vantage point nestled in the Hokulani interior courtyard.Relax and reconnect in the ample living space fully appointed for your...
The Villas at Poipu Kai #E210 By Parrish Kauai- Premier Villa with AC and walkab
The Villas at Poipu Kai are one of the newer luxury condominium resorts on the South side of Kauai in Poipu. These spacious and upscale condominiums are part of the Poipu Kai Resort that offers access to additional recreational amenities to all in the Poipu Kai...
Hale Kailani at Poipu Beach Estates - Walking Distance to Shops, Beaches & Fine Dining!
Welcome to Hale Kailani at Poipu Beach Estates! Kailani means “heavenly waters” in the beautiful Hawaiian language, and you will find just that at this luxurious tropical property. Cascading waterfalls into the heated pool create a soothing ambiance as you enter the...
Islander On The Beach - Oceanfront Resort /Oceanview Unit 244
CALENDAR GAP SPECIALS/ DISCOUNTED RATES Please ask for quote by responding to us for special discounted rates! We have "NO" added resort fees, "NO" amenity fees and "NO" parking fees.Units 244 – Check for any other specials that may also be available. Quick quote will...
Spacious 2-story condo with Maui views
Maui Kamaole J212 has split A/C units in the living area and each of the bedrooms. This two story, 2-bedroom, 2-bath spacious condo is situated on the 2nd floor and this property does not offer an elevator. J212 can accommodate up to 6 guests when using the queen sized...
Beautiful Oceanfront Condo on West Side of Oahu. Spectacular Sunsets
ALOHA, this beautiful, white sandy beach front home is located, right in front of Turtle Cove Beach. Not to mention, that it is also close to the world famous Makaha Surf Beach. Of course all the beaches on the West side are beautiful and is one of Oahu's best kept...
Includes Beach Gear! N24 Waikoloa Fairway Villas
Waikoloa Fairway Villas N24This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationBedding Configuration:Main Bedroom: King BedGuest Bedroom : King Bed (can be converted to Twins for $50 fee with advance...
Hideaway Bay: 2 BR Kilauea Home on 3 Acres - Tropical Garden & Ocean Views
Licensed Rental: TVR#4284/SP-2001-15Located on the bluffs of Kauai's Kilauea Farms, Hideaway Bay boasts stunning, unobstructed ocean views from every room in the house. The home is completely private and surrounded by three acres of citrus trees, mangoes, papayas,...
Hilton Pool Pass for stays thru June 2025. Waikoloa Beach Villas C23
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas C23 Please scroll down for detailed information:Bedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedLoft Area: Two Twin BedsHilton Pool Pass: Valid for stays now...
Luana Villa 18C ~ Your Private Oasis at Honua Kai w/ Large Lanai, BBQ, & Garage
Aloha & welcome to Luana Garden Villa 18C, the newest and most luxurious offering at the Honua Kai Resort in Kaanapali, Maui. This 3-bedroom, 3-bathroom villa is the epitome of elevated vacation experiences, with high-end amenities and stylish decor that exude both...