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.
DISCOUNTED RATES! 311 Beautiful oceanfront 2 bed 2 bath 3rd floor condo
Located on the 3rd floor of a small (only 42 units) quiet complex, you will have unlimited views of the beautiful sunsets, turtles feeding and playing in the reefs, right in front of the complex, and whales at play, during their season, on your private lanai. We have...
Kailua Beach Oceanfront Estate – Grand 6-Bedroom Retreat on Oahu’s Shores
This property is professionally managed by Private Homes Hawaii, LLC, a licensed brokerage in the State of Hawaii (RB-21170). It is licensed as a short term vacation rental, Non-Conforming Use Permit Numbers 1990/NUC-1777/1778 and is compliant with Hawaii State...
Maui Resort Rentals: Honua Kai Hokulani 448 - Spacious 2BR w/ Partial Ocean & Mountain Views!
Hokulani 448 is a luxurious two-bedroom suite offering gorgeous views of both the blue Pacific Ocean and the lush West Maui Mountains. Suite 448 affords a perfect opportunity to gather, reconnect, and celebrate. The suite can accommodate up to six guests in two...
Gorgeous Oceanview at Kaleialoha 214 Special 175 nightly for Nov- Dec
Amazing ocean views in an oceanfront condo at Kaleialoha. Nicely furnished and updated with a/c in living room and bedroom unlike other units in this complex, fully appointed kitchen and bathroom. Washer/dryer inside the unit for your convenience. Very quiet and private...
❤️PiH❤️ Island Melody Villa ♥ Stunning Views ★ Free Hilton Resort Passes ★ Bikes
Brought to you by Paradise in Hawaii Luxury HomesIsland Melody Villa at The Islands is a spacious 2,600-square-foot home that effortlessly blends luxury, comfort, and thoughtful design.Featuring three beautifully appointed bedrooms, this villa comfortably accommodates...
Imperial Hotel at the Waikiki Beach Walk Penthouse
PLEASE READ THIS IN IT'S ENTIRETY......Hawaii Tax ID #TA-137-632-1536-01 & GE-137-632-1536-01 TMK/Parcel# 260020140286 Address: 205 Lewers St Unit C/12B, Honolulu, HI 96815Located atop the newly remodeled Imperial Hotel at the Waikiki Beach Walk! New salt water rooftop...
Kauai's Sunny Poipu Beach Estates! A Beautiful Plantation Style home sleeps 8.
Summary:Escape to paradise in this spacious Poipu house, perfect for large families! Enjoy a huge private yard, a relaxing lanai for dining, and a luxurious primary bedroom with a jetted jacuzzi. This home offers a blend of comfort and convenience, ideal for creating...
!!! Come Swim With The Turtles!!!
This most beautiful oceanfront property location offers luxury living in paradise. This is the best location on Maui. Just steps to the ocean, you can truly unwind and relax here while enjoying an ever changing ocean show of breathtaking sunsets, sunrises and rainbows...
Palekaiko Estate - Kailua Kona Luxury Home with Ocean View
Palekaiko, meaning paradise, is our 3200+ sq. ft. home away from home situated on over an acre in a gated community. Palekaiko has three bedrooms, three and a half bathrooms, an office and almost 1000 sq. ft. of outdoor living space. On the property, you will enjoy over...
Lehua Lounge in the Heart of Downtown Kona
This place truly is hard to beat! Just 10 minutes walk to all Kona town, the beach & pier. In a peaceful neighborhood where you don’t hear any traffic noise at all. Newly installed AC (October 2025) keeping you cool & comfortable throughout the entire home. AC in both...
Oceanfront condo with pool, water view, & high-speed WiFi
Mahina Surf 114Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a lovely view of the ocean on your own privately furnished deck, as well as a view of the shared pool! This home...
Best of Mauna Lani! Clean, Spacious Resort Townhome, Pool/Beach Club!
This wonderful townhouse will help you make your Hawaiian vacation dreams come true! Beautifully decorated and well appointed you will find all of the comforts of home in this amazing tropical setting. The luxurious master suite will not disappoint with a king bed,...
"Drift Away" Studio Oceanview at Islander on the Beach 259
Drift Away – Oceanview Studio at Islander on the Beach 259Welcome to Drift Away, a second-floor oceanview studio at Islander on the Beach where you'll be transported to the peaceful beauty of Old Hawaii. Wake to the sound of the waves, breathe in the fresh ocean air,...
At Awapuhi Views, you can check out the surf conditions, and enjoy the breezes
Our home is located halfway down the Miloli'i Rd. We have a very large master bedroom with a King bed, the Master has bow- windows and its own door to the wrap around deck.oceanside deck. The Master bedroom has a walk-in closet, and en suite bath with tub and shower and...
Luxury condo in prestigious Hali'i Kai oceanfront community. Ocean bar and grill
Condo, 2 bedrooms, 2 baths, ( Sleeps 6 )Hali' i Kai is a 30 acre gated oceanfront complex on the Big Island of Hawaii with numerous luxurious resort like amenities. It is about a 20 minute drive from Kailua-Kona airport. Our condo, #23D is a spacious second floor end...
Tropical hideaway with pools, hot tub & grill - the waves await
Maui Kamaole H206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.
Aloha. Have you noticed how we're constantly towards the top of Kihei and Maui Vista searches. Well, vrbo has a system of metrics they use that ranks all listings, basically putting the best units available in front of guests...and we're crushing those metrics and have...
Modern, Oceanfront with A/C, discounted for 2025, plus monthly discounts!
Welcome to your Hawaiian Haven on Maui!Please scroll down & read the full description & FAQ's as we have likely already answered your questions below! You can also find out more (and get exclusive discounts) by searching for Hawaiian Haven and the Elikapeka Suite...
Zen Home with AC, Pool, Near Kailua Beach
Inquire about short stays, we accommodate them where possible. Spend your vacation in our Hawaiian style 4 bedroom, 4 bathroom home a 3 minute walk from Kailua Beach. Our home features a balance of indoor and outdoor living. There is a Zen like courtyard and inviting...
Deluxe Ka'anapali Condo with AC Luxurious Retreat
**Kaanapali Plantation #16 – Your Peaceful Island Getaway**Welcome to Kaanapali Plantation #16, your serene island retreat with expansive views of lush landscapes, the Royal Kaanapali Golf Course, and the islands of Lanai and Molokai, all framed by the stunning blue...
3BR Nihilani Condo with AC, Pool & Close to Shops 8C
PROPERTY DESCRIPTIONCome stay in Hale Honu! A luxurious, newly furnished, split-level Nihilani floor plan. Nihilani 8C is in an interior building away from streets and traffic noise and just a short walk to the pool and BBQ area.This unit features hardwoods throughout...
KeALOHA - INCREDIBLE views, Spectacular Beach Park, the Best snorkeling, Turtles
The MAUNA LOA SHORES is right on the ocean in HILO; an exceptional town with plenty to do here on the east side of our beautiful island. The Beach Park next door where you can swim with sea turtles is a once in a life experience. My 45 years as a resident and 42 years...
Kona Plaza#411 Top Floor In Heart of Kona Town, Ac & Elevators!
This unit of Kona Plaza is a beautifully appointed , 1 bedroom, 1 bathroom condo that has beautiful views. Boasting secluded tranquility and unforgettable sunsets overlooking the Historic Maku'aikaua Church steeples! Ocean Peekaboo views add to the magic, all framed by...
North Shore Barefoot Hideaway -- come relax with us!
NUC Registration # 1990/NUC-1967TMK # 1570010270146Welcome to our one bedroom, 2 bath condo at Kuilima Estates East. We are an easy 5 minute walk to the beaches by the Turtle Bay Resort. This clean and comfortable condo has a king bed in the master, pull out couch in...
Luxury Private Vacation | 180° Ocean View | AC | Pool | WiFi
Wanting a little getaway? The perfect private oasis awaits you. Imagine the background of the sun setting in the distance drink in hand, and all from your backyard look no further. Upon arrival through the 24 hr guard gated neighborhood, you feel overwhelmed with the...
Ocean Front Home with a Sandy Beach
Enjoy sunsets from the privacy of the large covered lanai, a sandy beach right out front, enticing tidepools, and the serenity of the perpetual song of ocean breezes in the trees at this lovely oceanfront setting.This versatile beachfront home can serve as the perfect...
SPECTACULAR VIEW LE PENTHOUSE 513B Luxury KING Bed OCEAN FRONT UPSCALE REMODEL
'LE PENTHOUSE' - BREATHTAKING VIEW- WHY STAY IN A CONDO...WHEN YOU CAN STAY IN LE PENTHOUSE! READ OUR REVIEWS, STAY IN UPSCALE WAILEA STYLE SURROUNDINGS! TRAVEL IN STYLE - EXPERIENCE OUR LUXURY PENTHOUSE OASIS! THIS 1 BED, 2 BATH HAS BEEN EXQUISITELY RENOVATED. ONE OF...
Villas By The Cove, Villa 3 · Step to White-Sand Beach
Villa 3 at Villas By The Cove is a stand-alone, single story 1 bedroom Villa Suite with ocean views. Its prime location is just steps from two of South Maui's most popular white sand beaches. Newly remodeled, and conveniently located, this 600 sq. ft. 1 bedroom villa...
Maui Kamaole B114 Book with Owner Summer Specials
Maui Kamaole Vacation Condo Rental. WE ARE NOT A MANAGEMENT COMPANY. RENT DIRECTLY FROM THE OWNER AND SAVE!New King size bed, new paint and drapes.Maui Kamaole B114 Vacation Rental is located at the front of the property, close to the main pool, Peek a boo view, and...
Hilo Lagoon Centre 707, air conditioned 2 bedroom, 2 bath condo in Hilo
Hilo Lagoon Centre is a mid-century modern building in downtown Hilo, Hawaii Island. Our condo unit 707 offers sweeping views of Mauna Loa, Mauna Kea mountains and the vibrant downtown area. Inside you have two suites flanking the main living area with kitchen....
Poipu Vibes in Modern Comfort! New Remodel AC- OCEAN VIEW Washer Dryer Rare find
New Remodel in Tropical Paradise..... A/C and Washer Dryer in the unit. This Penthouse unit has a very private setting. Enjoy this beachfront property with Penthouse ocean view.7+ night discount on non peak dates.The lanai will keep you captivated for hours. Watch the...
Prestigious villa with endless ocean views
Kapalua Ridge Villa 2622 is a high-end 1-bedroom, 2-bathroom villa situated on the second level that can accommodate up to 4 guests. Step inside the bright and airy main living area featuring Hawaiian-inspired decor and furnishings with a window air-conditioner and...
"What a Deal, for a unit this nice" (3/30- 4/30) RATE DROPPED to $199 per night ~ FRESH & AFFORDABLE
Welcome to one of the exclusive members of the Platinum Maui Vacations Ohana. We call this Kapalua Golf Villa, Hale O Kauka'i. A Hawaiian phrase which translates to English to 'Home of Sunsets'.Hawaii Tax ID # TA-089-018-4704-02NEW CENTRAL AC, (including new ductwork);...
🏖️Concierge Included | AC | WIFI | Mauna Lani beach access card | vrKCV🏖️
vrKCV - Kulalani at Mauna Lani 802, Professionally Managed by Kona Coast VacationsWelcome to Your Island Retreat in Kulalani at Mauna Lani!Experience the essence of tropical luxury in this professionally decorated and furnished 3-bedroom, 2.5-bath townhome. Perfectly...
Waipouli Beach Resort Luxury Garden Ground Floor! AC Pool
Luxury Garden Ground Floor!It was very easy to get in and out. No long lines at registration. Just walk to your unit. We may be flexible with an earlier check in. The Unit is spacious, pool is wonderful and location is great. Kauai has become quite the destination spot...
Beautiful Maui Home Away from Home
Aloha! Welcome to Hale Ma'kai (house beside the sea), my tropical-themed one-bedroom vacation condo in the Kihei Akahi complex in sunny Kihei. It is the perfect place to spend your Maui vacation. Hale Ma'kai is a spacious (696 SF), ground-floor condo with lanai opening...
This exquisite three bedroom ocean view residence offers stunning views of the Pacific Ocean from its prime 6th-floor vantage point, well above the tropical foliage of the Konea Tower interior courtyard, and located only one column back from oceanfront. Your group will...
Pili Mai 11I: Tropical Condo w/ Fairway Views, AC, Shared Pool & Jacuzzi
Modern island living comes to life at Pili Mai 11I, a newly constructed two-story townhome tucked along the 9th fairway of the Kiahuna Golf Course in sunny Poipu. With sweeping golf, mountain, and partial ocean views from its covered lanai, this spacious 3-bedroom...
Special Rate! Royal Kahana 1207, Top floor Condo with Amazing Ocean Views!
This property is hotel zoned, and not being affected by the recent proposed legislation.Royal Kahana 1207 located on the top floor with amazing ocean views! This 1 bedroom/1 bath has been fully updated and offers a gorgeous Maui retreat.As you enter you are immediately...
Kailua- Kona, Hi Vacation Rental Home With Pool
Ocean view and more! This is a beautiful 3 Bedroom, 4 Bath, Split level home with a private pool on the ocean. The large upper level lanai is a great place to relax and enjoy the sounds of the ocean. The view is amazing from here, whether you’re watching the family in...
$100 off the normal nightly rate of $595 for 7/2-7/16 new bookings
Tucked into lush tropical surroundings just steps from the soft sands of Waialea Bay, Ehu Kai is a charming two-story cottage designed to evoke the feel of a cozy beach treehouse. Surrounded by mature landscaping and flowering trees, this unique retreat offers privacy,...
🏖️Walking Distance to Private Beach | Lagoon & Ocean View | Concierge Included | vrKCV
vrKCV - Mauna Lani Terrace D203, Professionally Managed by Kona Coast VacationsExperience comfort and breathtaking ocean views at Mauna Lani Terrace D203, a 2-bedroom, 2.5-bathroom townhome located in the heart of the prestigious Mauna Lani Resort. Just a short walk to...
Private Hidden Retreat On North Shore Near Beach!
Discover Ha‘ena Place | North Shore Kaua‘iNestled on a quiet cul-de-sac, Ha‘ena Place is a true hidden gem—just a short stroll to some of Kaua‘i’s most iconic North Shore beaches, including Tunnels (Makua), Ke‘e, Lumaha‘i, and Hanalei Bay. Whether you’re snorkeling,...
KA 211 OceanFront Island Style Condo w Ocean View Pool
Kaleialoha 211 OceanFront Island Style 1Bedroom Condo with Ocean Views for Beautiful Sunsets, Whale Watching and Year Round Indoor-Outdoor Living for Getaways, Relax and Recharge FREE daily activities included with your stay value up to $570! Complimentary admission,...
BRAND NEW AC | Ground Floor 1 Bdrm | Peekaboo Ocean View | Pool | 5 Min to Beach
Brand new 24,000 BTU AC installed in the living room March 2023.The perfect Hawaiian getaway at this ground floor 1-bedroom condo with private lanai, located at the beautiful Kiahuna Resort.The condo is centrally located in Poipu and is within a 5 min walk of the...
Summary:Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled in September of 2021, no expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features...
Aloha Suite Near the Sea I, 3 Block Walk to Beach! Great Location!
TA-166-694-5024-01 STR Permit # 2211-CCH-0303, TMK 1260230500039Enjoy the ocean with gorgeous sunsets day after day. Fun shopping, great restaurants & entertainment all around you!This studio is the perfect choice for your Hawaiian holiday! With comfortable...
Dreamy 2 Bedroom Condo on Kiahuna Beach in Poipu! With AC! Unit 140
This beautiful 2 bedroom/2 bath 2-story beachy, tropical treehouse-feel condo is located on the 35 acres of impeccably landscaped tropical gardens of Kiahuna Plantation; considered to be the only beachfront complex in beautiful Poipu, Kauai. Year after year Poipu Beach...
Garden Oasis Near Kukuiʻula Shopping Village w/Shared Pool and Free WiFi
Waikomo Stream Villas 202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Like right out of the scene of a magazine, the garden oasis around Waikomo Stream Villas 202 welcomes you to...
Awesome Ocean Views in Top Floor Unit
Newly Remodeled Honua Kai Hokulani 710 - This is a top floor ocean view unit which is on the quiet south side of the Hokulani building. You will start your day with a beautiful sunrise over the Maui mountains and end your day watching the sunset all from the comfort of...