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.
Maui Tranquility II - Relax & Feel Welcomed!
Maui Tranquility II - Relax and Feel Welcomed! This is the second chapter in our Maui Tranquility story. Another amazing place to stay on Maui, completely remodeled with meticulous attention to the details so you'll feel comfortable and appreciate the aesthetics,...
Wailea Ekahi 40A - 5-Star South Maui Oasis
Welcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even sidewalk!Our private corner...
Wavecrest Oceanfront Rental
TA-061-740-4416-01GE-061-740-4416-01This recently remodeled ground floor oceanfront condo with spectacular ocean views on the lush and undeveloped east end of the " friendly" island of Molokai , is one of the most picturesque locations. Enjoy the amenities of the...
Hawaiian Charm..Just Steps From The Ocean..On Kauai's Sunny W Side * TVNC4216
PROPERTY OVERVIEW: House, 2 Bedrooms, 1.25 Baths, (Sleeps 4)The Nene Nest, Kauai is a classic, sugar plantation- style cottage located on the always sunny West Side of Kauai. Just 152 steps from the ocean, it offers a true Hawaii feel. Designed with a 'slow' pace in...
Magnificent Mountain Views ~Near Beaches & Village
We've got everything you need to enjoy your holiday: bicycles, boogie boards, beach chairs, umbrellas, BBQ and many other amenities.Only a 15 minutes drive to Hanalei Bay, Hideaways and Aninni Beach and a short stroll to Queen's Bath plus the amenities of Princeville...
🌴 Gorgeous Oceanfront Luxury Retreat 🌊 Pool, black sand beach, AC and billiards
We are THE perfect luxury listing on the east side of the Big Island! A quick distance to black sand beaches, waterfalls, the volcano and charming Hilo town. ALOHA! Welcome to Hale Kakahi or Hawaiian for “unique, outstanding, one-of-a-kind house” -a perfect name for...
Captivating Ocean Views from Polo Beach Club 805! Direct Beach Access
Book Your Stay and Get a $300 Gift Card!Planning a getaway? Book a stay of 5+ nights between September 24th and November 9th, and you'll receive a $300 gift card to enjoy at some of the best spots around! Choose from Cafe O Lei, Kohola Brewery, or Cool Cats to indulge...
>> Penthouse >> Ocean / Beach Front MILLION DOLLAR Views Spectacular 2Bd2Ba <<
The Ultimate Maui Vacation Rental. Spectacular Ocean / Beach Front Maui Penthouse the Hawaiian is an Ocean / Beach Front Maui Penthouse with 2 Bedrooms & 2 Bathrooms. Look no further The Hawaiian Penthouse has views you will never want to leave. The Hawaiian Penthouse...
Captivating Ocean Front Condo Living-Poipu Shores
Every evening, the sky transforms into a masterpiece of warm colors, reflecting off the endless ocean, creating an unforgettable view from this coastal retreat. This beautifully designed vacation rental offers breathtaking views of the Pacific, where you can watch sea...
Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.
Welcome to the monthly rental Penthouse in Lanikai! We have been sharing our piece of paradise for over 20 years.! Everyone deserves to experience the Hawaiian lifestyle! Sunrises, moonrises, walks, bike rides, and daily runs on the beach. We have guests from all over...
Kona Blue at Holua Kai: Luxurious Home w/ Private Pool, Spa, AC & Stunning Views
Kona Blue Vacations Holua Kai is a refined single-level retreat tucked within the private gates of Holua Kai in Kailua-Kona, perched along the manicured fairways of Kona Country Club. Blending island warmth with resort-inspired comfort, this 3-bedroom, 2.5-bath home...
3 bedroom Beach Tower at Ko Olina Beach Villas - Ocean View & Family Friendly!
Spacious 3-bd Villa at Ko Olina Resort. Beach Tower 5th floor on private wing with large floor plan (sleeps 6!)3 Bedroom 3 bath, with panoramic Ocean, Pool, and mountain views. Family friendly: pack-n-play crib and high chair provided.Exclusive beachfront property has 2...
99 steps to quiet beach - Centrally located - Great for families & groups
Ideally located on iconic Alii Drive directly where the world famous Iron Man takes place annually. A number of palm trees and local landscaping on the front and side of the property add to the tropical appeal.Nearby are many of Kona's enviable attractions including its...
Luxury Mahana Oceanfront Condo -1bd/2ba - Premium 10th Floor- Fully Upgraded
Welcome to Mahana 1015, a breathtaking oceanfront condo located on one of the top floors of the exclusive Aston Mahana at Ka’anapali Resort. Offering two full bathrooms and spacious accommodations, this one-bedroom suite is the perfect place to indulge in Maui’s natural...
Oceanfront tropical oasis in West Maui
Hale Mahina A 102 is a ground floor one-bedroom, one-bathroom unit making it convenient to unload groceries and beach equipment and does not have A/C. The master bedroom features a comfortable King size bed with bamboo sliding doors for privacy. The bathroom features a...
❤️PiH❤️ Sunshine Oasis ★Hilton Passes ★ Closest 4BR to KaMilo pools Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sunshine Oasis, a part of our Hawaiian Luxury Collection.Sunshine Oasis at KaMilo is a wonderful 4 bedroom home (Mahina Model)We pride ourselves on providing some of the most sought after homes on the Kohala...
2 Bedroom Kona Coffee Farm with Ocean Views in Holualoa
The rental is the entire downstairs with it's own private entrance and large patio with BBQ. The downstairs has two separate bedrooms with a large family room in the middle. The kitchen has a refrigerator, sink, microwave, two burner hotplate, toaster over, and coffee...
Ilikai 1 Bedroom City Views, minutes to the Beach!
This spacious 7th floor unit at the Ilikai Hotel offers comforts of home while on vacation. Relax on the cooler side of the building and enjoy the tropical breezes from the mountain. KITCHEN- Refrigerator- Cooktop/Oven- Microwave- Dinnerware, Glassware, Silverware,...
Ilikai Hotels Best Kept Secret!! Updated & Furnished with Yacht views!
Conveniently located on the 3rd floor of the Ilikai Hotel, this condo is perfect for your time on Oahu. With the convenience of full kitchen, two bedrooms, two bathrooms and two spacious lanai this is a great choice when traveling with friends or bringing your family....
Contemporary Hawaii Living, Calm North Shore Beach
Experience Hawaii in its purest form in this beautifully built custom home, sitting on an exclusive beachfront property on the North Shore of Oahu. Built with the idea of taking in the gorgeous ocean and mountain views, and maximizing the flow of the trade winds, this...
16B; Ocean View, Quiet Beachfront King Studio in Luxurious Wailea Ekahi Resort
Ocean View, King Bed, quiet Ground floor Studio condo, in the beautiful Wailea Ekahi Resort, near one of the 4 private pools and a short walk to the beach.Enhanced cleaning protocols and private ground floor entrance with Lanai opening onto the beautiful gardens and...
5 Bedroom with Private Pool, Spa, Gym and Putting Green in Waikoloa Beach
Welcome to Aloha Sunrise, your private paradise in Ainamalu at Waikoloa Resort. This luxurious retreat offers seclusion, convenience, and endless relaxation, near Kona's dining and entertainment.Inside, experience elegance and comfort. This lavish getaway accommodates...
Beautiful Ocean & Golf course views at this Kapalua Golf Villa, discounted 2024
Our Kapalua Golf Villa sits on the 4th hole of the Bay Course. You will be street level with just three steps down to the entry. Enjoy watching golfers while having your coffee or have happy hour with beautiful ocean view sunsets from our oversized lanai. You are...
5 Bedroom with Private Pool and Spa in Waikoloa Beach
Ainamalu - Protected Land - is a newer resort area on the big island. This is a luxurious and unique oasis: it is away from the tourist crowds, yet only minutes from great restaurants, grocery stores and some of the best beaches in the world.Ainamalu Memories is a...
Hilton Waikoloa Pool Pass for stays through 2025. ML Beach Club Pass. Palm Villa
Mauna Lani Palm Villas F4. Includes Mauna Lani Beach Club Pass. Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Two Twin BedsGuest Bedroom: One Queen BedLoft Area: Full Sleeper SofaHilton Pool Pass: Valid for stays...
Spacious Maui Beach House, Private Pool, AC, Sleeps 6
GE: 184-440-0128-01TAT: 184-440-0128-01Aloha and welcome to the Hale Anna, Maui. The Hale Anna is a beautiful, private home located across a quiet street from miles of sandy beach. This home is a legal grandfathered vacation rental with the Maui County Department of...
WOW! Stunning Ocean Views, Large Deck &Luxury Beds
*Please note that per Maui county law, that two adults and two minors are allowed per bedroom. We are allowed to host up to 4 adults and 4 minors for a total of 8 guests. This is a private top floor unit of a 2 level home. Our favorite aspects of the home are:*Large...
Watermark - Luxury 2BD/2BA/1PA on 22nd floor with an Ocean View!
This unit has 1 queen size bed, 2 twin size beds, and 1 sofa bed, and can accommodate maximum of 5 people. This picture-perfect luxurious unit has 2 bedroom/2 bathroom/1 parking. From the bedroom, you are able to see the brilliant view of Ala Moana Beach from a window...
Lanikea at Waikiki - Luxury 2BR Suite Ocean & Park View
This 2 bedroom unit comes with 1 California king-sized bed, 1 queen-sized bed, and 1 sofa bed, and can accommodate maximum of 6 people. The unit is equipped with a full kitchen with cookwares and utensils. A brilliant view of the ocean and park from the living room and...
Waialua Oceanfront Luxury Home – Secluded North Shore Escape
Featuring Two Master Suites!!!Search no further - this luxurious oceanfront beauty has all the makings of a heaven-sent vacation on one of Oahu's most secluded coastlines. Furnished throughout with hand-picked Balinese furniture and decor, this home is a treat to see...
Large Family Retreat on Calm Swimming Beach, A/C
Leimoku is a large and accommodating, beautifully updated, and modern Hawaii home on Oahu's famous North Shore. Located on the "quiet side" of the North Shore, away from all the crowds, this 3000 sq.ft. home is comfortable and luxurious, with three of the four large...
True Beachfront Luxury! Downstairs unit oceanfront 20' to water! NO resort fees.
Luxury Beachfront Retreat at The Pikake in Maui - Ground Floor GemEscape to paradise with our newly remodeled ground floor condo at The Pikake in Maui! Experience true luxury with this one-bedroom, one-bathroom beachfront oasis located on the desirable West side of the...
Pristine Hawaii Retreat with Ocean, Golf & Palm Tree Views. Top corner unit!
Feel at home in this gorgeous corner, top floor villa in the Hali'i Kai oceanfront development in upscale Waikoloa Beach Resort. This fabulous 2 bedroom villa is perfect for 4 adults (plus one child with owner approval).Enjoy your morning coffee on the lanai, taking in...
Kaanapali Shores Ocean View POST FIRE SAVINGS Unit 203 2BR 2BA
UNIT 203 (Remodeled in 2020) 2-Bedroom, 2-Bath Central Air-Conditioned Unit with a full kitchen, dining area, living room & 2 lanais. The bedrooms and Living Room all have an ocean view. A NEW pull-out sofa that turns into a Queen Bed allows for up to 2 additional...
🏖️Beautiful Ocean View! | Central AC | Serene Surroundings | vrKCV
vrKCV - Nakukui Ekolu, Professionally Managed by Kona Coast Vacations Nakukui Ekolu at Kahakai Estates - The Piece of Mind RetreatDo you need a vacation? Not just a trip, but an actual vacation? That is what you'll find at the Piece of Mind Retreat. If you wanted to,...
Luxury Ocean View 2 bed/2bath Beautifully Remodeled; Unit #325
Relax in luxury in this 1100 sf property which has plenty of space to enjoy the views and beaches of south Maui. Quite possibly the nicest and most complete renovation in Hale Kamaole with every detail attended to in its upkeep. Upgraded AC in this modern beach style...
Gorgeous 3 bedroom 3 bath, Luana Garden Villas, 10B Ground Floor
***Aloha and Welcome to Maui and Luana at Honua Kai Resort***Luana 10B is a ground level beautifully designed and fully furnished villa in the new Luana subdivision of the Honua Kai Resort with 2047 sf of indoor living space. The large lanai provides gorgeous outdoor...
Historic Upcountry Ranch Home
PERMITS: SUP2 2019/0015 and STMP T2019/0002MAUI’S VRBOS ARE NOW OPEN TO TRAVELERS FROM THE MAINLAND AND ELSEWHERE. FOR LATEST INFORMATION PLEASE GO TO travel.hawaii.gov. WE PROVIDE: 1. ENHANCED CLEANING PROCEDURES BETWEEN GUESTS 2. HAND SANITIZER AND DISINFECTING WIPES...
Beachside Bliss, Condo Just Steps Away From the Ocean - Sugar Beach #129
SUGAR BEACH RESORT, #129Welcome to Sugar Beach Resort #129 – a charming ground-floor condo that blends comfort, convenience, and beachfront beauty. With direct access to Maui’s longest beach, this updated retreat is perfect for morning walks, sunset strolls, and...
Next Generation / Remodeled-2 Bedroom-2 Full Bath-End Unit-Specials!
Magnificent large 7th floor end unit condo, considered the corner suite, is fully equipped with new furnishings, including barn doors, new ceilings, new bathrooms, new kitchen, new flooring and ultra modern features throughout. This condo has literally been rebuilt from...
Ocean Views and only Steps from Magic Sands Beach!
TAKE IN A VIEW OF LAʻALOA BEACH (aka Magic Sands) FROM OUR LANAI! The top floor condo is directly across the street from La'aloa beach park (aka Magic/White Sands) - at most a 5 minute walk from the front door. Try boogie boarding at the beach with one of the boogie...
Luxury Mahana 1bd/2ba-Beautiful Remodel- Incredible Views-Free Parking/WiFi
Mahana 715 is a 1BD/2BA condo featuring the best direct beachfront location, panoramic Pacific Ocean views, year round sunsets, and seasonal whale watching at its finest. The Mahana is one of a kind with its close proximity to the water and there is truly nothing like...
Poipu Pili Mai 9B, Flexible Cancellation, 4 bdrm, AC, Sunset/ Golf Course View
This is a 3 story building with our 2 story unit located on second and third floors with entry to condo up a flight of stairs. We have four bedrooms, 2 on the second story (the condo's main floor) which are Master suites. While upstairs on the third floor there are two...
Rustic Cabin in Volcano Village
Rustic Cabin in the rain forest, located 5 miles to Hawaii Volcanos National Park.The quaint country cottage will draw the image just right.House is tailored to rejuvenate and enjoy seclusion in the forest.You can expect peaceful surroundings suited to relax and boost...
Oceanfront Villa - 3 bedroom with amazing views! APRIL 18-25, 2025
-AMAZING VIEWS from the OCEANFRONT balcony!-Master bedroom with king-sized Westin Heavenly® Bed and HDTV-Master Westin Heavenly® Bath with large shower, vessel tub and double vanity-Guest bedrooms with king-sized Westin Heavenly® Bed and HDTV-Guest Westin Heavenly® Bath...
Exquisite on Paradise*Fully Upgraded with Ocean Views!
This freshly renovated condo offers stunning ocean views and a large, airy lanai with comfortable outdoor seating. Pack up the cooler and head to the beach or lounge by the pool and soak up the serenity that is Kauhale Makai.This roomy condo is just steps from the...
The "Promise Tree" - Great Family Gathering Place in Kailua Kona!
Please only book through VRBO or a reputable site!Experience the exquisite natural beauty of the Big Island. This beautiful custom home built in 2014 is located in an extremely quiet community 5 minutes from downtown Kailua-Kona. There are spectacular views of both the...
Ocean, Greenbelt and Haleakala view Ekahi 33E
Ekahi 33E offers a rare setting with views of the ocean, Ekahi's greenbelt and Haleakala. In Ekahi's lower village it's a short walk to the main pool and Keawakapu Beach. Renovation completed Jan 2020 & new to the rental market, 33E is exceptionally well furnished,...
Kuilima Condo with Split Air
Welcome to our little piece of paradise. A perfect place to stay during your visit to Oahu. Our CLEAN and beautifully UPDATED condo can sleep 6 comfortably. With TWO king beds and a one queen sofa bed. It also includes a brand new full-size kitchen with a dishwasher,...
ADORABLE*Modern Beachy Decor Studio in South Maui
** A Solar Panel Removal and Installation Project will occur in the KIHEI BAY SURF Complex in the month of July 2024. There could be times of intermittent noise and dust. Rates have been discounted to reflect accordingly.This studio offers every amenity to make for a...