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.
Mauna Kea Resort Villa, Ocean Views With Pool & Spa In Backyard
Aloha and welcome to our home, villa #311. Our villa offers concierge service to all of our guests. We have ocean views, a private pool with spa, and gourmet kitchen with professional grade appliances. The villa is bright, airy and spacious with vaulted ceilings,...
Oceanfront Home w/ Pool Access, Views in Papaikou
Furnished Gazebo | Gas Grill | 3 Mi to Honoli'i Beach Park | Off-Grid PropertyYour next Hawaii adventure awaits at this eco-friendly Papaikou vacation rental! With easy access to hiking trails, beach parks, chocolate farms, and more, this 2-bedroom, 2-bath house ensures...
The Whaler! ~Beautifully remodeled ground floor courtyard studio~
Unit 162. Update: Fall of 2022 we installed a Grohe hand-held shower head so that parents could more easily wash their children. In the summer of 2021 we added new artwork. In 2019 we installed a new 55” Samsung LED LCD Smart TV! It’s beautiful and has “Dynamic...
KRV 1423 2BD Kapalua Villa w Ocean Views Relax Recharge
FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu’au, Golf, Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W3)*One...
Paia Inn - 3 Bedroom Ocean Front Beach House
At the Paia Inn, your safety and well-being is our top priority. Our dedicated staff is here to make your stay comfortable and memorable – with outstanding customer service, in-house amenities and dining, and great vibes. We have implemented new cleaning + safety...
Charming Modern Home Stunning Scenery and Nature BBPH2021/0002 SUP2 2020/0008
Located in the heart of the north shore of Maui, this charming 3-bedroom residence is a refuge for those who want to experience the beauty of Maui in comfort and tranquility. The house is 2254 square feet and has a beautiful view of a Hawaiian native forest. It has...
Kaanapali Alii | 493
Escape to paradise in this stunning 1,513 square foot mountain view condo at Kaanapali Alii. Perched on the ninth floor, this one-bedroom, two-bath vacation rental with an additional den comfortably accommodates up to four guests, offering a perfect blend of space,...
Hale Kokio: A Magical, Romantic Cottage, on North Shore Kauai #4212
Welcome to Hale Kokio, a well loved getaway, designed for two. This is the place to stay on North Shore Kauai for relaxation, privacy and island living. Enjoy a quiet setting and a convenient location. The newly updated cottage is designed with your comfort in mind. A...
Kope Cottage -1 BR -1B-Endless Views
The Cottage sleeps 3 people in 600 sq ft. It is a true one bedroom and not a studio. It has 1 full size bed and 1 queen size bed. It also has a queen-size pull-out sleeper bed as outlined above. There is also a modern washer/dryer in the Kitchen area.In the cottage, it...
Oceanfront, Split AC unit, remodeled November 2024, king bed washer dryer unit
• Oceanfront• Split A/C units• King bed• Remolded November 2024• Beach access from condo complexFully remodeled in November 2024, unit 313 is a custom built, detailed, upscale condo welcoming you. You will find this bright, beautiful one bedroom, one bathroom...
Enjoy Sun Rise over Volcano & Sunset over Ocean from our Lanai! BEST VIEWS!!
This completely renovated condo features:-Two bedrooms-Vaulted ceiling-Two full baths-Loft-Over 1200 square feetLanai offers breathtaking views of Haleakala volcano and the ocean.All-inclusive rates: Free WiFi, no resort fee, no extra charges for parking, no security...
Seabreeze:110' Oceanfront, Majestic Mountain Views, AC, Outdoor Shower, 30 Daysn
Seabreeze is a beautiful North Shore Hau'ula beach home with 110' of ocean frontage, spectacular sunrises & majestic mountain views. Dine on the lanai with turquoise ocean water so close you can almost touch it. Our home overlooks the sea & mountains (a rare & gorgeous...
Ocean Views from this 2 bdrm/2 Bath Ground Floor Family Friendly Condo
Welcome to Kauai Hale Kai at Poipu Sands. Poipu Sands unit 313 is a Deluxe two bedroom/two bathroom, ground level condominium with a spectacular ocean view. Poipu Sands is right next to the Grand Hyatt Resort property.Poipu Sands has a large heated pool with a deep end...
Waipouli Beach Resort Gorgeous Luxury Oceanfront!
Gorgeous Oceanfront Waipouli Beach Resort G302, one of Waipouli Beach Resort's most desirable Ocean Front suites, offers spectacular 180 degree unobstructed ocean and sandy beach views. You can see the ocean from every room! Fall asleep to the sound of the waves every...
Stunning Ocean View - Steps from the beach - Kahala 623
Kahala 623 is a 1,000 square foot condo overlooking the immaculately kept Poipu Kai greenbelt with barbecues and walkways leading down to Brennecke's Beach. Imagine yourself sitting on the lanai, your favorite beverage in hand, a gentle trade wind flowing over you as...
A Tropical Paradise 2 Bed/1bath. Stunning Bay and Ocean Views
A Tropical Paradise on Hawaii's Big Island This updated 2bed, 1/bath penthouse has stunning views of both the bay and the ocean. Whether you are a lover of marine life or just a lover of tropical views, this home is the perfect spot for you. The penthouse's prime...
Contemporary upgraded villa with ocean views
Kapalua Bay Villa 11G1 sits at the front of the resort, offering stunning views of Oneloa Bay and the island of Molokai. This one-bedroom, one-and-a-half-bathroom villa is the perfect getaway for a small family or couple, with a maximum occupancy of 3 guests—2 adults...
A wonderful place to be.....
E 'Aka 'Aka Mau loosely translates as Laughs a Lot House in Hawaiian. Our two bedroom, two bath home is a perfect getaway for couples and families! Just 400 feet from the beach, and with a beautiful view of Mauna Kea and Mauna Loa, our house offers two sides of Hawaii,...
Two-story condo in central Poipu with lanai, pool & W/D - walk to Baby Beach
Waikomo Stream Villas 132Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tropical breezes, lush landscaping, and beautiful on-site amenities await at this two-story condo in Waikomo...
Fairway Villas at Waikoloa Golf View 1 Bedroom
1 Bedroom Golf View- Kitchen features granite countertops, ceramic cooktop and oven, refrigerator, microwave, dishwasher, coffeemaker, toaster, rice cooker, blender, cookware and tableware- 1 king bed or 1 queen bed - Queen sofa bed in living area- 950 sqft/89 sqm-...
Perfect Family Beach House. Walk out gate to Amazing Beach.
The Waialua Beach House is located on the North Shore of Oahu, just steps from the beach. It’s only 2 miles from Haleiwa and its shops and restaurants and a short drive to the famous surf spots of Sunset, Pipeline, Haleiwa and Waimea. This recently remodeled and...
New Listing! Luxurious 4BR/3BA House with AC
Discover Elegance at Poipu: The Leilani House hosted by BlueTideVillasWelcome to The Leilani House, a beautifully designed 2,100-square-foot retreat set on a private half-acre just minutes from Poipu Beach and local dining. Celebrated as one of Poipu’s most desirable...
Kauai Loft Retreat PF-H307
Pono Kai's pool will be closed for repairs September 2025 through November 2025.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Welcome to Kauai Loft Retreat – Your Perfect Island Escape!Nestled in beautiful Kapaa, this...
Exquisite Oceanfront Home, 4 Bedrooms, 2 Baths, Central A/C, Sleeps 8
Privacy for your family, but still close to town. Quiet beach at your doorWelcome to "Aloha Niulani"! Our 4-bedroom 2 bath Oceanfront Beach home comfortably sleeps up to 8. Conveniently located in the Old Kauai town of Kapa'a. Tucked away in a secluded neighborhood with...
Easy Kauai Living! Lanai to Lawn, Full Kitchen, WiFi, Ceiling Fans–Kaha Lani 102
Castle Kaha Lani Resort #102 - Energy flows from the tropical decor living area onto the lanai and across expansive lawns of this 739 sq. ft. ground floor villa with beautiful ocean view. Dine in with meals prepped in the full kitchen. Other touches include ceiling...
Kona Isle D2 DIRECT OCEANFRONT, Best View!
Updated kitchen and bathroom! D2 at the Kona Isle is a beautiful DIRECT OCEANFRONT property on the 1st floor of building D! No stairs! Cook in the full kitchen or on the grill! Enjoy dinner with a sunset view from your living room, lanai, or picnic tables! Feel the...
60% OFF April - June/25, Ocean & Garden Views, Kaanapali Beach, Air Conditioned
Thank you for checking us out! The condo has been updated and new pictures are coming. Current pictures do not show the updates. NO resort fees!!! Resort fees are covered by us!!!We are located North Kaanapali beach and this is a legally permitted vacation rental and is...
Whale Watching! Spectacular Ocean Views – Newly Remodeled Maui Condo!
Newly remodeled, fully air-conditioned, ocean view condo. Ocean, Island, Sunset, and Whale Watching Views! Our unit is on the third floor of Building G at Papakea Resort with pool view and unobstructed ocean view with year-round sunsets.We want to provide our guests...
Just renovated and right on the ocean! No hidden fees.
Book with Confidence! If there is any government restriction in the United States which prevents you from travelling to Kauai, or which imposes an isolation period for travellers upon arrival in Kauai, I will refund 100% of your payment (I can't speak to VRBO's policy...
Watermark - Luxury 2BD/2BA/2PA on 36th floor with an Ocean View!
Discover a breathtaking retreat perched "on top of the world" with wide-open ocean views that showcase Magic Island and Ala Moana Beach Park. Experience the perfect blend of indoor and outdoor living with a stunning, usable lanai to savor paradise every day.LIVING...
Spectacular Oceanview Condo: Stylish, Serene, Modern
Enjoy contemporary sophistication in a tropical setting from our top-floor, corner oceanview condo in the Waikoloa Beach Resort on the Big Island of Hawai'i. Sunlight fills the space and the lanai faces west, providing a shaded breakfast area as the day blossoms, and...
NEW LISTING! ~ Napili Point with Amazing Views
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! Welcome to Napili Point C35, a stunning 2-bedroom, 2-bathroom condo nestled in the heart of Napili. Spanning 1,059 square feet, this spacious oceanfront retreat comfortably accommodates up to 6...
Papakea Paradise, G102, 2 Bedroom & 2 Bathroom, Ground Level, Air Con, Specials!
The much coveted ground floor, one level, 2 bedroom - 2 bathroom floor plan at Papakea. No steps! Also, brand new ductless air conditioning system in both bedrooms and living room / kitchen area. An amenity not all of the condos have! AND PAPAKEA IS NOW A NO FEE...
PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!
"Kihei Oasis On Maui” is a LEAGALLY permitted vacation rental home located in Kihei, Maui, and not included as a property in Maui County's phase out bill. Permit #STKM 20130014. Please know that you can book this legal, permitted home and will not have you booking...
Cool retreat at the entrance to Lanikai. Very Close to Beach. 3 Primary Bedrooms
Live your best life! An opportunity for beach living in this renovated and updated luxury rental with views of Kailua Beach and Kailua Beach Park - it's brilliant turquoise blue ocean, sandy beach, large grassy areas and tall ironwood trees. Fine craftsmanship abounds...
BEACHFRONT/GROUND Floor B-103: Renovated, LARGER unit, & steps from the sand.
Pocket sliding doors from the large 2 living room areas to the large lanai to the white sandy beach! Open concept with amazing ocean views everywhere in the large room, which includes the dining room area plus well equipped kitchen with subzero fridge and marble counter...
Hawaiian Treehouse, Peaceful Glamping Retreat
BAUMHAUS - a fully off-grid 12 feet high tree house on 2 acres of tropical rainforest on the Big Island of Hawaii. Experience stargazing like no where else in the world, while warming up at the fire pit. Chill out in the large hanging net or spend rainy days in the hot...
Charming Holualoa Ranching-Era Estate near Kailua and Keauhou. Away from it all!
Gracious comforts of yesteryears and featured in the coffee table book, The Hawaiian House Now, the home is an historic 1895 structure, modified in the 1940s. Retaining the charm of old Hawaii with architecture and furnishings of the day, while satisfying the needs and...
Modern Waikiki Studio, 2 Beds, AC, WiFi, Pool & Fitness room
Escape to this fabulous studio in Waikiki, Honolulu. This welcoming retreat offers a peaceful atmosphere for up to 4 guests to unwind. With a cozy living area with 2 beds (1 Queen & 1 Full), a relaxing bathtub, and convenient amenities like WiFi and AC, this studio is...
Luxurious Upgraded 2 master BR 2 private BA Fairway views, 200 yards from Ocean
We invite you to enjoy the peaceful, old-Hawaiian feel of Kauai’s North Shore and the upscale yet understated elegance of Princeville with a visit to our beloved home. Located on the 8th fairway of the world-class Makai golf course, our second story corner unit...
LOOKING FOR A LUXURY CONDO WITH FAB VIEWS? THIS IS IT! Located in Hotel Zone.
Just steps away from the famous Kamaole I beach is our luxury 3 bedroom/2 bathroom condo. This extra large unit boasts luxury furnishings. We have amazing views of the Ocean and West Maui from almost every room! Relax and enjoy breakfast on the double lanai viewing the...
Kalo Homes ~ Sunset Retreat
Escape to our enchanting vacation rental nestled in the picturesque Makaha Valley. Ideal for nature lovers and beach enthusiasts, our cozy retreat offers the perfect blend of tranquility and adventure. With more than enough room for a large family or multiple small...
Grand Island Paradise on Golf Course w/Ocean Views
🌅 Relax and enjoy sunset ocean views every night!🏖️We are
Includes Beach Gear! 518 Villages at Mauna Lani
Villages at Mauna Lani 518. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: Two Queen BedsGuest Bedroom Downstairs: One King BedMauna Lani Beach Club Pass: Your stay will...
❤️PiH❤️ House of Manta ★ Hilton Waterslide & Pool Passes ★ Bikes ★ Golf Clubs
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to House of Manta, a part of our Hawaiian Luxury Collection. House of Manta at KaMilo is a wonderful new single level 3 bedroom home. We pride ourselves on provide some of the most sought after homes on the...
Steps to Beach at Maui Banyan-resort style amenities-AC, WIFI, Full Kitchen
Cozy 1BR Condo in the Heart of Kihei – Walk to Beach!Escape to sunny Kihei, where this charming one-bedroom condo puts you just a short walk from Kamaole Beach Parks 2 & 3—perfect for sunbathing, swimming, and catching breathtaking sunsets. With beach gear provided...
Experience Luxury Living in our Penthouse Condo with Free Parking-Book Now!
Our luxury one bedroom condo is a penthouse (top floor) mountain and pool facing condo with vaulted ceilings, new appliances and Keurig. We are situated at the beautiful ocean front Waipouli Beach Resort. The large main bedroom features a King size bed (with a brand new...
Best Maui Adventure!! Explore the island while you sleep under the stars
Ready for a unique experience on Maui? Want to explore the entire island and stay over in the most remote and beautiful spots? Want to spend a fraction of the price of staying at a hotel/resort? You've found the best accommodation with Epic Maui Camping :)Whether you...
Private, Peaceful, Perfect!
Our lovely townhome is a hidden gem located in the Fairways development at the Mauna Lani Resort. The small Fairways complex surrounds a large pool, hot tub and common area. The outer perimeter borders golf course and open space. The gated complex is private, peaceful,...
Maui Kamaole A205 Remodeled with spectacular Ocean Views
Stunning ocean views from this spacious Maui retreat at the popular Maui Kamaole in South Kihei. This two-bedroom condo is amongst 14 of the largest floor plans at 1,224 square feet, and features high ceilings and lots of room to entertain. The fully equipped kitchen is...