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.
Lilikoi Cottage - In The Heart of Lovely Waimea
We have switched to renting for a longer term of a minimum of 6 months. Available from Oct 2023 onwards. Spacious artist's cottage in heart of Waimea. Rare find! Walking distance to coffee shop, celebrated restaurants, farmer's market, art galleries. 15 mins to the best...
Fern Grotto Inn -Trip Advisor & Lonely Planet Recommends our Old Style Cottages!
Tropical Garden Cottages—One Block from BeachWhy stay at Fern Grotto Inn? The reasons are as numerous as our glowing guest reviews. In fact, Fern Grotto Inn recently became the best-rated vacation rental on TripAdvisor and was featured in Lonely Planet—all thanks to...
A Welcoming Beachfront 2BR/2BA, Vacation Home, W/D, AC, STEPS TO BEACH!
This is a completely renovated 2 bedroom/2 bath 1,148 sq ft. condo within a stones throw from the beach! When you enter the unit you will be taken aback by the Hawaiian vibes! Open the patio door and immediately feel the ocean breeze from the trade winds and smell the...
❤️PiH❤️ PACIFIC VISTA RETREAT ★ Luxury Retreat w/ Ocean Views ★ Heated Pool
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Pacific Vista Retreat, a part of our Hawaiian Luxury Collection.Pacific Vista Retreat in Kahakai Estates is a wonderful 5-bedroom home, minutes away from downtown Kailua-Kona. It has some of the most amazing...
Konea 301 at Honua Kai Resort ~ Rare Frontline Ocean Views, Private BBQ on Lanai
FALL SALE - BOOK 7 NIGHTS OR MORE AND RECEIVE 10% OFF THE NIGHTLY RATE FOR ARRIVALS NOW UNTIL OCTOBER 31st 2025Welcome to Konea 301, a luxurious and spacious suite with stunning ocean views with full access to the Honua Kai Resort. Experience breathtaking ocean views...
Stunning Property in Building 10 of Kamaole Sands
Completely remodeled, luxury condo in Kihei, Maui. 2 bedroom, 2 bathroom, third floor, end unit in Building 10 of Kamaole Sands. Kamaole Sands is directly across the road from Kamaole III Beach Park and Building 10 is closest to the beach. The ocean views are amazing...
Modern Luxury Suite at Waikiki Beach Tower w/ Ocean View
Relax in this beautifully renovated unit with ocean views at Waikiki’s finest oceanfront condo building. Wake up to the crystal blue ocean from the luxurious king bed in the master bedroom, entertain family and friends in the open kitchen and living room, and enjoy a...
Stunning, Romantic Cottage on Slope of Hualalai
On the Kona side, safe and away from the volcanic activity, the Cottage awaits you. The perfect, peaceful getaway for those on a honeymoon or looking for a relaxing, romantic experience. This warm, welcoming, newly-built and finely crafted studio cottage provides modern...
Lae Nani 433. New renovation. Fabulous Ocean View from this Top Floor Condo. A/C in Bedroom!
This top floor (3rd) condo has one of the best views on the island. From your living/dining area and lanai you can view Wailua Bay and even watch the Humpback whales breach in the winter months.As you can see from the photos, it is an updated and very comfortable condo...
Enjoy this Lovely Tropical Paradise!!
Enjoy this Lovely Tropical Paradise!! Registration Number: GE-096-482-7136-01, TA-096-482-7136-01 ********************************************************************************************************
Home with Panoramic Ocean Views + Private Pool
E Koma Mai (Welcome) to this upscale retreat that offers you a true luxury experience. Sitting on a hillside, this home boasts unobstructed views of the coastline from the main pool deck, upper lanai, and from nearly all interior spaces. With 3 bedrooms and space for 6...
Hapuna Beach Paradise 2 BD Penthouse Oceanfront Views + Mauna Kea Beach Resort
Important Notice for 2026 BookingsIf you're booking a stay with us for dates beginning on or after January 1, 2026, please be aware that a Hawaii tourism tax increase of 0.75% will be implemented to support climate relief efforts on the Hawaiian islands.Although this...
147 Ten Star Reviews out of 147, AMAZING, Maui Magic, A206 with AC, BEACHFRONT
BEACHFRONT ON MAUI... A206 AT NAPILI SHORES RESORT! Located directly on gorgeous Napili Bay on West Maui with 240-degree view of the water and spectacular West Maui sunsets. This property is NOT affected by the vacation rental issues here on Maui. There is practically...
Charming oceanfront condo with lovely views - pool, hot tub & sauna on-site
Sugar Beach Resort 415Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Snorkel, surf, and swim at this charming Sugar Beach Resort condo! Boasting a prime, walkable location to one of...
Ocean Pearl at Turtle Bay Resort - Kuilima Estates West
Ocean Pearl is a luxurious retreat nestled in the heart of scenic Turtle Bay Resort, offering a perfect blend of comfort, convenience, and breathtaking views. With three full bedrooms and two full Jack & Jill bathrooms, this spacious abode provides ample accommodation...
Maui Stunning Prime Ocean Front View of the Bay and Haleakala! *Maalaea Kai 212*
Enjoy this 2nd floor unit featuring gorgeous views throughout the unit of Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. The unit is tastefully decorated with the spirit of Aloha and has a portable a/c unit in the bedroom to keep you...
Kailua Beach Historic Renovated Cottage
This property is offered as a monthly rental. Although full-month occupancy isnot required, the monthly rate remains fixed and applies in full, regardlessof the number of nights stayed, as prorated rates are not available.One of the original homes on Kailua Beach, this...
Beautiful Ocean View Studio at Kihei Akahi
Welcome to Kihei Akahi! This is the perfect location for your Maui vacation. Step cross the street and enjoy Kamaole Beach 2, one of Maui's best swimming beaches. The condo has a fully equipped kitchen, making it ideal to enjoy dinners at home. The lanai is perfect for...
Best 2 Bedroom Condo In Wailea - Enjoy Paradise All Year
Aloha and welcome to our home at The Palms at Wailea. The ocean view will take your breath away the minute you step inside. But it's the condo renovation and our commitment to our guests that will keep you coming back.Our remodeled unit has beautiful floors, plenty of...
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
• Oceanfront• Split A/C units• King bed• Remolded June 2023• Beach access from condo complexFully remodeled in June 2023, unit 218 is bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei welcomes you! This second floor condo is...
OCEANFRONT Spectacular Condo - Breathtaking Ocean Views and 60ft From the Water!
Allow the sound of the waves to relax you as you enjoy a beautiful condo with all the modern amenities directly on the Ocean in Maui. High end appliances throughout. Modern decor professionally accessorized by Swan Interiors. Enjoy all the modern conveniences; free high...
Westin Princeville Luxury One-Bedroom Villa
Perfect for a couple or small family just wanting to get away and enjoy the beautiful island of Kauai. Villa has full kitchen, king bed in bedroom and queen size sofa bed in living room.. Lanai has chairs and table. Next door to golf course. Beautiful swimming pools,...
Large Luxury Home w/ pool and Ocean Views. Special discounted rate March 2025
This magnificent architectural masterpiece - a luxury home that captures an unobstructed 180-degree vistas of the Pacific Ocean, stretching from the iconic Diamond Head to Koko Kai awaits you. Enjoy ever-changing views, from sunrise to sunset, a daily spectacle. Nestled...
Waipouli Beach Resort D407, 199.00 May19-21 BlowOutSal wKitchen, 10 StarReviews!
Luxurious Hawaiian Modern Timeless Theme Top Floor PENTHOUSE Waipouli Beach RESORT D407, Beachfront Resort."CRAZY" Mountain Range VIEWS and Evening SUNSETS, a "ROMANTIC" Master 2bd/3ba w/a King bd in one rm & 2 Full bds in another & Queen Sleeper sofa. "Hawaiian Theme"...
Beautifully Decorated Whaler Studio at The Whaler on Ka'anapali Beach
Property Description: West Maui is open for business and welcoming visitors! The Whaler on Ka'anapali Beach is a world class oceanfront condominium resort located directly on Ka'anapali Beach in the heart of world-famous Ka'anapali Resort. The Whaler offers all the...
Alohale - Serene Premium View Luxury Villa, Mauna Kea & Golf Views......Paradise
Alohale | Aloha (Hello) + Hale (Home). Kulalani is a special place you will want to return to again and again. This artistically presented home offers true serenity and privacy with world class services and amenities all around. 3 beautifully furnished Bedrooms, Granite...
Beach Walker at Champion Ridge: Mauna Lani Resort Home with Pool & Spa
Welcome to Beach Walker at Champion Ridge by Gather, a stunning four-bedroom, four-and-a-half-bathroom estate located in the prestigious Mauna Lani Resort on Hawaii's renowned Kohala Coast. This 3,500-square-foot retreat offers breathtaking views of the ocean, volcanic...
Ocean View Condo with 3 shared pools, beach access, grill areas, & more!
Plantation Hale F5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*BOOK MAY 28-JUNE 2, 2025 FOR A DISCOUNTED NIGHTLY RATE*Located in the heart of Wailua, on the Royal Coconut Coast...
New Remodel & Rare Find #35 w/ Oceanview, AC, and corner unit! Look no further!
It's all about the location, views, and our new remodeled unit! Located in building 7, one of the smaller buildings with only 6 condos, you are in the heart of this oceanfront resort and steps from the beach!Remodeled kitchen and bathroom, all new flooring throughout,...
Hapuna Beach Residence A21 at Mauna Kea Resort
This immaculate, oceanfront, newly-constructed, island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a sleek, epicurean kitchen with Wolf and Sub-Zero appliances, wine storage and hand-crafted cabinetry, plus a dining...
Yonegan Maui Getaways - Haiku - Unit 7
Yonegan Haiku beckons to travelers seeking the lush side of Maui offering centered between downtown and more “cosmopolitan” Kahului and the up-country paniolo charms of Kula and Makawao. A five-minute drive brings you to Ho’okipa Beach, the surfing Mecca of the...
KBM Resorts | FREE CAR | Honua Kai | Ocean view | 2-Bedroom Condo with Huge Wraparound Lanai! HKK-413
Luxurious Ocean View villa at Honua Kai Resort featuring spacious living areas, gourmet kitchen, resort pools, dining, and Kaanapali beach access.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31,...
Sea, beach and courtyard views - prime location
Unit 811 at the Whaler is one-bedroom, two-bath. Sitting in the best location on Maui’s prestigious Kaanapali beach, this luxurious courtyard-facing condominium has breathtaking ocean and island views. Relax on the spacious private lanai while looking out over the...
Oceanfront Remodeled-30 Feet to Ocean-CENTRAL AC-Highly Sought After
One of only a dozen like it at Papakea, this oceanfront corner unit wraps you in 180° views of Moloka’i, Lana’i, and the deep blue Pacific. Sip coffee from the lanai, prep dinner in the gourmet kitchen, or catch whales mid-breach while stretched out on the designer...
Pili Mai by Gather: Stylish 3BR Condo w/ Pool, Lanai & Scenic Views
Welcome to Pili Mai by GatherDiscover your perfect island retreat at Pili Mai by Gather, a modern and stylish 3-bedroom, 3-bathroom condo located on the scenic Kiahuna Golf Course in sunny Poipu on Kauai’s south shore. With picturesque panoramic mountain and distant...
Maui Kamaole H207: across the street from Kamaole Beach Park III in South K
Between the ocean views, floods of sunlight, and adorable tropical accents you are sure to find your piece of paradise in this cozy South Maui Condo. Every room has an abundance of storage space and furnishings so you can make yourself at home. There are ceiling fans in...
BEST LOCATION with Incredible Direct Ocean Views, A/C Papakea L207
L207 rests in the most HIGHLY DESIREABLE locaton at the Papakea Resort. Enjoy a front row seat to direct oceanviews and spectacular nighly sunsets. This condo and location is everything you dreamed about when coming to Maui. This one bedroom one bath has been remodeled...
Great value! Two Bedroom Hilo Condo with air conditioned bedrooms
Welcome to Hilo Terrace 228 in the heart of the historic town of Hilo on the east side of Hawaii Island where tourists mingle with locals and really experience the 'spirit of Aloha'. We welcome you enjoy Hilo and the surrounding areas. This complex is a mixed use with...
Ko Olina Resort Beach Oasis- Ground Floor 2 bedroom Condo, Near Pool, sleeps 4
Coming to Ko Olina for a full month? Come stay in a great condo with a prime location at Ko Olina Kai gated community.This is a wonderful 1,144 sq. ft. two bedroom ground floor end-unit condo, within a 8 to 10 minute walk to the beach lagoons, and directly behind the...
15% OFF Season - Exclusive Penthouse with 3 Master Bedrooms & Breathtaking Views
"Majestic Masterpiece" is located in one of the most beautiful vacation areas in Hawaii....overlooking Kapalua Bay, Maui, on the ocean's edge of a world famous beach, offering year round breathtaking sunset views. This spectacular 5th floor, private penthouse occupies a...
Beachfront Resort - 2 Bedroom Villa - Resort View w/ Balcony - Family Friendly!
*IMPORTANT NOTE - Availability varies. Please message me with desired dates for availability confirmation*Welcome to the Westin Nanea Ocean Villas in Maui, Hawaii! This stunning resort offers a variety of luxurious villas, perfect for your vacation getaway. Enjoy...
🏖️AC Thruout | Beautiful Ocean & Golf Views | 2 Bedrooms w/ Loft | vrKCV
vrKCV - Country Club Villas 315, Professionally Managed by Kona Coast VacationsUnit 315 at Country Club Villas offers an unparalleled experience, perfectly positioned on the 18th fairway of the Kona Country Club Ocean Golf Course. Whether you're a golf enthusiast or...
Maui Kamaole G211, picturesque ocean views!
Maui Kamaole G211, picturesque ocean views! This 2bed/2bath condo offers the perfect getaway for families or couples traveling together. Take in the relaxing views from your private lanai. Enjoy your morning coffee or dine al fresco with seating for four! With floor to...
Luxurious ocean inspired studio in Paia short walk to Maui's coolest beach town
This modern newly remodeled studio is hidden away in our tropical sanctuary we call Mangolani Inn. The studio has a king size bed, comfy love seat w/ driftwood coffee table & Mango wood dresser. Spa like custom tile bathroom and shower will make you feel like you are...
Luxury Ko'Olina Coconut Plantation Oahu, 2-Story, 5 min to beach
Dream-like comfort awaits you and your family in this beautifully appointed 2-story, 1,700-square foot, 3 bedrooms, 2.5 bath townhouse vacation rental condominium in an award-winning residential resort community that offers privacy, relaxation, entertainment, and...
Vintage Farmhouse and Botanical Garden
Old Hawaii Style restored home! One minute to Kalopa State Park hiking trails! Private deck, botanical garden, walking paths, large sunroom bedroom, retro kitchen, clawfoot tub, outdoor shower, and more. Ten minutes to Historic Honokaa Town, with it's great restaurants,...
STUNNING NEW REMODEL-SUNSETS-LUXURY-QUIET LOCATION-AC-LARGE LANAI
Book with confidence, this stunning, 1 bedroom, 2 bathroom (1022 sq. ft) condo that has been completely remodeled from top to bottom with modern finishes, where even the lanai sliding doors were replaced. This condo is managed by PMI Maui, a local Real Estate Brokerage...
Hale Lanikai – Classic Hawaiian Style Beach House & Guest Cottage
HALE LANIKAILic# TA-161-257-7280-01Non-Conforming Use Permit Number 90/TVU-0031and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations.Hale Lanikai is BACK! Better than ever!!All new furnishings throughout the property.Original Koa...
>> 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...
Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course withnPool.
Serene, peaceful, and relaxing. This 3 bedroom, 2 bath single story home is located in Kailua-Kona, across the street from beautiful He'eia Bay (a one minute walk). The house sleeps 6 people and is stocked with most items needed for a relaxing convenient vacation. Most...