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.
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...
Tropical Escape w/ Pool Access ~ 1 Mile to Beach
Pack your bags and prepare for tropic splendor when you make this slice of paradise your Hawaiian home base! Located in The Villages At Mauna Lani, this well-appointed 3-bed, 3.5-bath vacation rental invites you to embrace island living with ease. Take the townhome’s...
Wrap Around Lanai Oceanview Luxury Suite – Hokulani 441
This condo is zoned hotel and is a legally compliant vacation rental in Maui CountyOceanview Luxury Suite – Hokulani 441Experience unparalleled island living at Hokulani 441, a two-bedroom, two-bathroom suite at the renowned Honua Kai Resort & Spa. With an expansive...
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...
Konea 505: 2 Bed/2 Bath with Stunning Ocean & Sunset Views at Honua Kai
SUMMER FLASH SALE - BOOK 7 NIGHTS OR MORE AND RECEIVE 10% OFF THE NIGHTLY RATE FOR ARRIVALS NOW UNTIL JUNE 29TH 2025 Welcome to Konea 505, a luxurious 5th-floor interior courtyard two-bedroom suite at the Honua Kai Resort in Maui, Hawaii. This stunning suite boasts...
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...
Beautiful Lae Nani Unit 112 Oceanfront One Bedroom Condo Coconut Coast Wailua.
You will enjoy a completely remodeled (AC included) condo with all new appliances, fresh paint, floors, cabinets, and countertops when you book your stay with us!! Aloha & welcome. Thank you for considering our condo. The current price is your win and don't miss out on...
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....
Spectacular Oceanfront Puako 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...
Gorgeous condo in a beachfront Wailea resort
Wailea Ekahi 24B is a 1-bedroom, 2-bathroom condo that offers a split A/C system, a private washer/dryer, and easy access to this ground-floor unit. Unit 24B can accommodate up to 4 guests. The master bedroom features a California king-size bed and elegant touches. The...
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....
Side by side penthouse suites with Central Air and unencumbered Ocean Views
* 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 activities desk.*Penthouse consists of TWO one-bedroom...
Hallor House: Breezy Hideaway Near Tunnels & Na Pali Trail
Enjoying a prized location among the closest legal vacation rentals to picturesque Tunnels Beach, Hallor Hale is situated on a quiet cul-de-sac, surrounded by a large lawn and tropical vegetation. Within this tranquil setting on Kauai's spectacular north shore, guests...
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 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...
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...
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 : Two Twin Size Beds (beds can be converted to King for $50.00 fee with...
Privacy, Beach, Hot Tub and Ocean Views. TVNC#4284
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 through...
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...
Romantic Waikiki Beachfront Condo w/ Spectacular Ocean View
💖 A Romantic Retreat for TwoWelcome to your dream couples’ getaway in the heart of Waikiki! Perched high inside the iconic Foster Tower, directly across from Waikiki Beach, our ocean‑front condo delivers sweeping Pacific views, modern comforts, and the...
Posh & Lavish ... 2 ADJOINING SUITES ... Direct Ocean Views
*************************************************************************************ALL ADULT GUESTS IN YOUR PARTY MUST AGREE TO SEND PHOTO ID AFTER BOOKING CONFIRMATION AND BEFORE ARRIVAL &...
Infinity-edge Pool, Spa, BBQ, Fire-Pit, Ocean Views! HOSTED ~ Hale Laule'a
Summary:Hale Laule'a, an Island Style Beach Hosted Property with (2) separate dwellings, is located on the Kohala Gold Coast of the Big Island. In the main residence that guests stay in, there is air conditioning throughout this 4 bedroom, 3 bath home situated on nearly...
Dog-friendly condo with furnished lanai & washer/dryer plus pool & tennis
Hale Kamaole 249Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This second-floor retreat is a bright and open oasis located just steps from the ocean! Enjoy evenings watching...
Hale A Kai - a 4br/4ba golf course home in Princeville
TAT # 063-351-8080-01 - "House by the Sea"Hale A Kai. This beautiful custom home is located in the Queen Emma Bluff's gated community in Princeville. The home is approximately 4000 sq feet. Upstairs is a large great room with beautiful hardwood floors. There’s a well...
Oceanfront Cottage 5A
You can't beat the views and privacy from 5A!Perfectly situated on the lot, with picture-perfect views of sunsets, Kaiaka rock, and Oahu. Your cottage has a new kitchen (January 2023) and offers amazing natural light and sense of space from 3 walls of windows/doors and...