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.
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...
Serene Lanikai House Near the Beach w/Full Kitchen and Great Outdoor Space
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out,...
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...
Wailea Elua Village 2006 - 2 Bedroom Ocean View Condo
Wailea Elua Village 2006 is a charming vacation rental that epitomizes the luxury and tranquility of Maui. This beautifully appointed two-bedroom, two-bath condo offers an ideal retreat for families or friends seeking a relaxing island escape. The residence boasts a...
KP13-Beachfront-WD-Pool -Sunsets-2nd Floor
Unit #13 is a beautifully situated, top-floor located in Building 3 of Kiahuna Plantation Resort in Poipu. This unit offers a private retreat with ocean views, making it an ideal choice. This condo does not have AC at this time but we also own #9 with AC.Guests have...
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 is a hotel zoned property so it is not affected by any proposed government action dealing with vacation rentals. Our unit is fully licensed by the State of Hawaii and County of Maui,...
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
Set within the exclusive gates of Mauna Lani Resort, Beach Walker at Champion Ridge by Gather is a 4-bedroom, 4.5-bath luxury estate that blends island serenity with sophisticated design. Overlooking lush fairways and framed by distant ocean and mountain vistas, this...
Ocean View Condo with 3 shared pools, beach access, grill areas, & more!
Plantation Hale F5 - November Promotional Rate!Our 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,...
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Enjoy the exclusive Wailea lifestyle in this fashionably decorated, high-end suite with incredible ocean views!!!---This gorgeous, bright and spacious 1-bedroom, 2-bathroom top floor unit offers unmatched views of the ocean and the scenic Wailea greenbelt area. This...
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
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
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 14K, a contemporary three-bedroom, three-bath condo located on the scenic Kiahuna Golf Course in Poipu on Kauai’s sunny south shore. With sweeping mountain vistas, distant ocean glimpses, and refined island design, this spacious second-floor...
Maui Kamaole H207: across the street from Kamaole Beach Park III in South K
PROPERTY PROJECT:The upper pool will be closed from November 11th through November 21st 2025 to re-coat the upper pool deck. 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...
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...
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...
🏖️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...
Adorable Guest Cottage with Lanai -sleeps 3
This adorable 2 bedroom 1 bath Guest House is in a country like setting surrounded by sounds of nature and overflowing with ambiance. Located at about 1000 ft. above sea level, you will be serenaded by coque frogs , roosters, turkeys and chickens. There is a picnic...
Beautiful, large studio with Mountain views from deck, beach access & A/C
This is a large studio, "The Mountain Suite" resides within a triplex building on the edge of a cliff over Anini beach on the North shore of Kauai! Complete with kitchenette, separate bathroom, partial ocean views and The Napali coast. This is a great place for a couple...
AquaTemple Lodge & Waterfall Jungle Property
Imagine relaxing and swimming in a private river just steps from your home...the gorgeous river front property has multiple waterfalls, a secluded river beach and a lava tube/cave surrounded by lush jungle. Your group will have the whole property to yourself, with a...
Shores of Maui - Ocean View with pool
The Shores of Maui UNIT #208 overlooking the pool and ocean. Everything is first Class 'A', with granite in the kitchen & bathroom and new flooring throughout. All new class 'A' furniture, appliances, linens, carpet, 55' HDTV, NEW BEDS. Pack & Play crib and high chair...
1-Bed, 1-Bath - Walk to Beach. Inquire for May and June.
Private, detached, gorgeous, newly built, fully equipped, one bedroom guest house ready and waiting to be booked by you! Superb location! Short walk to beautiful parks and beaches and minutes drive to historic Haleiwa Town.This incredible, newly constructed modern home...
🌺Moku Paradise Hale - Oceanfront
***30-day rental. Please inquire.Welcome to Moku Paradise! This 3-bedroom, 3-bath + studio cottage island style oceanfront home has breathtaking ocean views and a semi-private beach. This is a perfect getaway paradise for those seeking a calm, private, and relaxing...
🏖️Renovated Penthouse | Lake & Golf Course Views | AC | vrKCV
vrKCV - Fairway Villas Waikoloa J34, Professionally Managed by Kona Coast VacationsRelax. Rewind. Renew. Welcome to "Nani 'ola ola" at Fairway Villas Waikoloa Beach Resort, a stunning mid-century modern penthouse retreat designed for relaxation and unforgettable views....
Maui Resort Rentals - Exclusive Hyatt Residence Club 1BR Mountainview Lower Viilla
Exquisite 1 Bedroom Mountainview Lower Villa at Kaanapali's Newest, Most Exclusive Resort! Proudly perched upon Ka'anapali, one of the world's most beautiful beaches, is the Hyatt Residence Club Ka'anapali. Within the lush borders of this sprawling tropical paradise,...
New May Specials, 5 Star Reviews! F403 Top Floor 2 BR/3 BA
Welcome to the Waipouli Beach Resort and Spa! The premier resort on Kauai!Waipouli Beach Resort and Spa is located beach front on the Coconut Coast between the historic towns of Kapaa and Wailua. Located convenient to both Princeville on the north and Poipu Beach on the...
Experience Paradise At Our Modern Hawaiian Cottage With Ocean Across The Street
Experience paradise living at "Surf Temple," a stunning Hawaiian Cottage with a perfect blend of modern decor and traditional charm. With lava rock walls gracing both the house and property, every corner of this place embodies the essence of Hawaiian culture and spirit....
S&N Lux suite/Free Parking/King Bed/Kitchen/Wi-Fi
Experience luxury in our modern suite in Honolulu, Hawaii. Nestled amidst European-style gardens, our resort harmonizes with Oahu's tropical charm. Relax in the outdoor pool, stroll through the garden, stay fit in our gym, or unwind in the sauna. Explore Honolulu's...