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.
Brand New! Luxurious Sky Ala Moana 2 Bed 2 Bath
Summary:*30 DAY MINIMUM* Discover the lively heart of Honolulu and enjoy leisurely walks along the beach with this 2 bed and 2 bathroom apartment on the 16th floor of Sky Ala Moana. Get a charming view of the city and take advantage of the convenience of being close to...
Kaanapali Stunner - Spectacular Ocean Views
Updated 2025 - New Furniture and flooring. New pictures soon.As owners, we are committed to providing a high quality safe and clean vacation experience for both first time and loyal guests of Whaler 559. This unit is highly upgraded with loads of extra amenities and...
Rare Beauty and Luxury at Kealakekua Bay
Your hosts Tammy and Joe are committed to providing a 5-star experience. The home is maintained in immaculate condition with the highest levels of spotless cleaning before you check in. The property is very private with secure gated access. Parking at the guest house...
Oceanfront Beachfront Escape Hale Kai 1Bed
Discover charm and comfort in our ground floor vacation rental, nestled by the pool and oceanfront. Immerse yourself in stunning sunsets just steps from the water. This cozy unit boasts a fully equipped kitchen, a luxurious king-size Tempur-Pedic bed, and a sofa sleeper...
Three bed three bath luxurious townhome in gated Princeville community
3 Bedrooms, 3 Baths, Sleeps 6VILLAS ON THE PRINCE #2 is a luxurious 3 bedroom, 3 full bath townhome in one of only 3 gated communities in Princeville on Kauai’s beautiful north shore. Newly renovated, it is one of the only units offering A/C upstairs as well as in...
Maui Kamaole B101 - Gorgeous designer condo! Modern luxury and great rates!
Condo was fully renovated, new cabinets, tile floor, granite countertops, stainless appliances and new A/Cs. The Master Bedroom boasts a California King bed, ensuite bathroom, and private courtyard. The modern kitchen is very well stocked and you will enjoy the Weber...
LUXURY VILLA, 3 Private Suites, Pool/Spa, Gym, Central A/C, Beach
This exquisite Villa has it all! Located in The Villas at Poipu Kai boutique development. With 1900 s.f. living area, this three bedroom three bath view unit features an expansive covered lanai, private elevator access, central air, central vacuum, washer/dryer, and...
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
We are a 2-3 minute walk to beautiful Kamaole Beach III. Our building is located in quiet building 5 on the 2nd floor. Our unit is close to the elevator but far enough away to not hear it. Additionally, there is a beautiful ocean view from our lanai!The remodel of our...
Gorgeous Oceanfront! - Sweeping Views & Steps to the Beach
Welcome to our oceanfront home away from home! You'll find views straight out to the ocean and the wild coastlines of Kapalua. The villa is perched above the sweeping white sands of Oneloa Beach and is steps away from three other world-renowned beaches. Our...
Maui Kamaole One Beachfront Condo at Charley Young Beach
Discover your perfect Maui beachfront getaway at Kamaole One #9, this beautiful 2-bedroom, 2-bath oceanfront vacation rental located directly on Charley Young Beach, the north end of the world-famous Kamaole I Beach Park in sunny South Kihei.This rare oceanfront condo...
Luxurious, 2 bedroom / 2 bath, FULL Ocean View Wailea Condo
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and desirable complex that is exceptionally quiet and free of any traffic noise. This property is located in less than a 5...
Edge of Cliff Luxury Penthouse over Largest Coral Reef in Hawaii - Beach Access & AC
Very large penthouse with 2, 000+ square feet of living space under roof, vaulted ceilings and the most incredible views over the largest coral reef in the State of Hawaii. Ocean views available throughout the condo's living area and into the huge master bedroom suite....
Hale Hihimanu - newly renovated house and guest cottage with AC
Hale Hihimanu - a newly renovated house and guest cottage with AC throughout. Located on a private driveway with just two neighbors, this property offers unprecedented privacy for a home in the resort community of Princeville. The beauty and elegance of this property...
Luxury Villa: Hilton Pool Passes, Renovated, Private Beach Club, Sunset Views
Enjoy staying at the best location at Golf Villas, featuring ultimate privacy with breathtaking sunset views and unlimited access to a private beach club and unlimited access to the Hilton Pool for 6 people. Our well-appointed and recently renovated villa is located in...
Kaanapali Alii | 265
Welcome to your dream vacation rental at Kaanapali Alii! This luxurious two-bedroom paradise is the perfect destination for your Hawaiian getaway. Nestled in the heart of Maui's renowned Kaanapali Beach, this spacious rental offers a blend of comfort, convenience, and...
Welcome to 3 Luana Garden Villas 1A,1C& 1D Oceanfront resort Partial ocean Views
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful Luana Garden Villas at the Honua Kai Resort.This listing is for “three” separate neighboring villas, which is perfect for a multi-family vacation. Luana Garden Villas is the final phase of Honua Kai...
Highest Guest Rating at Mana Kai, Best Ocean Views, Luxury Amenities, Ocean End
THE TOP-RATED, 5-STAR LUXURY VACATION RENTAL CONDO AT MANA KAI WITH DIRECT OCEAN VIEWS ON KEAWAKAPU BEACH:This is the one! Mana Kai Unit 402 is a newly remodeled luxury condo with direct beach and ocean views available at the Mana Kai Maui Resort. This premier condo is...
Private Luxury Estate w/Pool, Jacuzzi, AC & Ocean Views: Ohana Le'ale'a
Step into the beauty of island life at Ohana le'ale'a, a newly built 3-bedroom, 3.5-bath luxury estate in Kona that blends expansive indoor-outdoor living with sweeping Pacific views. With 3,180 square feet of refined design, a private pool and spa, and a game room...
- Luxury Vacationing Modern Condo - Spring Specials -299 USD-
***The pool has just been renovated and is gorgeous*** DESIGNED BY A NYC ARTIST. THIS BEAUTIFUL CONDOMINIUM IS BORDERING KIHEI AND WAILEA IN SOUTH MAUI, HAWAII. IT IS LOCATED AT THE GORGEOUS MAUI HILL RESORT BY ASTON. THE PROPERTY HAS BEAUTIFUL GARDENS, SWEEPING VIEWS...
Oceanfront HK-B7 - Maui Condo on the Beautiful Serene Beach of Ma’alaea Bay
Experience the ideal beachfront getaway at Hono Kai B-7, a charming condo nestled in the serene beauty of Maui. This idyllic retreat offers stunning ocean views from the living room, bedroom, and lanai, providing a picturesque backdrop for your vacation. The...
Panoramic Ocean & Mountain Views --we have FULL AVAILABILITY please message us.n
Let the Aloha spirit be with you during your Hawaii visit by staying along the famous Koolau Mountain range on the lush Windward Side of Oahu. With 3900 sq. ft. of space to relax and enjoy a panoramic view of the grand mountains and the peaceful ocean as a backdrop,...
Ho'olei Ocean View 21-6 Newly Listed, Renovation May 2025
Remodel completed June 2025! See the new photos just posted!The entire home has been repainted, almost all the furniture was replaced, a lot of new beautiful art was added, and all new hardwood French oak floors were installed in the bedrooms.. We also remodeled the...
Luxury Oasis Palm Villas at Mauna Lani
Luxury Oasis at Palm Villas in Mauna Lani Resort on the Big Island of HawaiiWelcome to your dream Hawaiian getaway at the Palm Villas located in the Mauna Lani Resort, where paradise meets perfection! Nestled within the prestigious Palm Villas community, our luxurious...
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Welcome to your tropical paradise getaway! This resort-like 5 bedroom home with swimming pool, hot tub, waterfalls, and stream is ideally located in a quiet cul-de-sac and offers the perfect blend of relaxation, comfort, and breathtaking ocean views. With Magic Sands...
Tropical-inspired decor with partial ocean view
Kuleana Resort 313 is a charming 1-bedroom, 1-bathroom condo that comfortably accommodates up to 4 guests. The spacious bedroom features a luxurious California King bed, complemented by 1 window A/C unit for added comfort. Additional sleeping arrangements include a...
3 BR Oceanfront Villa: Marriott's Lahaina Tower; Jan 9 - Mar 6th, 2027
Spend up to 8 consecutive weeks in the same 6th floor oceanfront villa within Marriott Ocean Club Lahaina Tower! Availability 1/9/27 through 3/6/27Can also be rented weekly. All weekly rental reservations must begin on a Saturday and depart on a Saturday.This 1700...
Hale Hahalua - Serenity and Ocean Views in Kona now with upgraded A/C in bedr.
Aloha! Welcome to Hale Hāhālua – the gateway for your dream vacation on the Big Island of Hawai’i. Located in the picturesque community of Keauhou (Kailua-Kona), right above Keauhou Bay, our condo offers you the perfect starting point for your adventures. In...
Kona Coast, BEST Oceanview&Pool, Yoga/Meditation Space, Pickle Ball&Basket Ball
Welcome to Halani — Your Serene Sanctuary on the Big IslandEscape the busyness and crowds of the resort scene and discover Halani, meaning “heavenly breath”—a peaceful retreat perched above the South Kona coast, offering one of the most unparalleled ocean views...
New Listing! Tropical-themed 7th floor studio
Kaanapali Shores 721 is a Studio condo with central air conditioning that can accommodate up to 3 guests. Located on the seventh floor, you will find an open-concept layout and tropical-inspired decor with a sense of island serenity. When it's time to rest, unwind on...
Mau Loa Hale: Perfect Location 5 Acres Walk to Bch! Open concept! Breeze & Views
Welcome to Mau Loa Hale, a private island-style retreat on five acres between the Koʻolau Mountains and the Pacific. Here, dramatic ridgelines meet ocean breezes, creating a peaceful escape where you can spread out, recharge, and experience Oʻahu at a slower rhythm....
TRUE OCEANFRONT PARADISE! Royal Mauian #311
ALOHA!Welcome to Kihei, Maui and your oceanfront paradise! Our incredibly beautiful condo is near the center of the building and only steps away from the water. Watch whales, savor the sunset and enjoy the sound of the waves from the large lanai, the living room or even...
Spectacular Panoramic Ocean Views - Private Ohana
Live like a local at the Ocean Blue Ohana. You'll have the entire private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500...
Aloha Condos, Kanaloa at Kona, Condo 3703, Oceanfront, AC
1700 Square feet of breezy vaulted-ceiling living space, with new tile floor and paint throughout. Refinished koa wood cabinetry in all new kitchen. Ceiling fans in all major rooms and lanai (5). Powerful whole house ventilating system reduces demand for AC. High...
Waikiki Shore Beach Front Studio
Large beach front studio (460 sq, ft,) located at the Waikiki Shore, the only condo building in Waikiki that is directly on Waikiki Beach. This unit is located in a building that is within the designated Resort Zone, and therefore eligible for short term vacation...
Waikoloa Village Golf Course Fairway 2-bedroom condo with Central AC-WiFi, Views
Waikoloa Fairways -From the Summit of Mauna Kea to the Kohala Coast Line, Welcome to Paradise! Central Air Conditioning! Aloha! E Komo Mai! This gorgeous condominium offers everything you need for your Big Island getaway. Located in the highly sought after community of...
Renovated 03/23! Direct Oceanfront Condo with 2 Master Suites!
*Available for booking! Thankfully, our condo is not located in the wildfire affected area*Enjoy stunning views in this newly renovated oceanfront condo located on Kahana Beach! This spacious 1,040 sqft condo located at Valley Isle Resort has been completely renovated...
Kolohala in Haena is a tranquil place to enjoy your tropical vacation!
Kolohala in Haena is a peaceful place to enjoy your tropical vacation. Great for honeymooners! It faces a beautiful meadow with horses and cows. You can walk to a string of white sand beaches in 5 mins. Close to Ke'e beach, Tunnels beach, Kalalau hiking trails, Napali...
Westin-Top island and beach in the world, oceanfront, pools, kitchen, family
The Westin Nanea Ocean Villas, Ka'anapali, is built on 16 acres on Maui's legendary North Kā’anapali Beach. Enjoy Maui's newest oceanfront resort, where you can relax in paradise. Walk out onto the spectacular beach, lounge at the beautiful pools (heated pool,...
Oceanfront Boutique Condo. 5% Discount for Most Stays of 7 or More Nights
Enjoy stunning ocean views from all the bedrooms and living area of the condo. Greet every morning on your bed enjoying the views and sounds from the ocean!*** OCEANFRONT overlooking greenbelt, quiet and private, no noise from pool or parking lot ***Uncork a bottle of...
Two Bedroom Upgraded Waikoloa Fairway Villa
Perfect for a postcard worthy family vacation, girls’ getaway, solo trip, or whatever your heart desires, Fairway Villa C21 is located in the Fairway Villas gated community of Waikoloa Beach Resort and is the perfect destination for rest, relaxation, reconnection, fun...
Luxurious 2-Bdrm, 2.5-Bath Condo with Parking & Fitness Center in Prime Waikiki!
Experience luxury living in this 2 bdrm/2.5 baths/1 parking, corner-end unit at Waikiki Landmark! Located in the Makai Tower, this unit offers breathtaking city and partial ocean views. No detail was overlooked in the thoughtfully designed kitchen renovation, featuring...
Hale o ka Nene: Luxury 6BR Estate with Pool, Spa & Golf Views
Welcome to Hale o ka Nene by Gather, a luxurious six-bedroom, six-and-a-half-bathroom estate on the sunny South Shore of Kaua'i. Perfect for families or group getaways, this private retreat accommodates up to 15 guests and features panoramic golf course views, a private...
Hawaiian Bungalow ~ A/C~ Near Beaches & Shops
Experience the aloha spirit in this bright, airy Hawaiian-style home, where vaulted ceilings and tropical garden views create the perfect island retreat. Designed with family fun in mind, the game room offers ping pong and foosball, and the garage is stocked with...
Lei Hali'a - Steps Away from Poipu Beach with A/C!
Located just steps away from the world famous Poipu Beach and Brennecke’s Beach on Kauai’s sunny South Shore, Lei Hali’a is ready to help you create lasting vacation memories from this island paradise. From the spacious and comfortable outdoor living space...
Pu'uwai Place in the heart of Volcano Village
Pu'uwai Place is centrally located in the heart of Volcano Village, just outside Hawaii Volcanoes National Park. Cooper Center, convenience stores, and restaurants are all within walking distance. You'll feel right at home in this newly updated home with full private...
Beautiful Mountain Views & Steps to Waikiki Beach
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Oceanfront Paradise! Sea Turtle Cove Napili Point
WOW! Spectacular Ocean and outer island views. Your oceanfront patio is just steps away from the beautiful Honokeana Cove (commonly called turtle cove), which lends to excellent and safe snorkeling on most days. Sip on your Mai Tai, take a deep breath, and enjoy the...
STEPS FROM STUNNING MOLOAA BAY
Formerly "Hale Houston" Moloaa Beach Hideaway is a 2 bedroom, 2 bath home situated just steps away from beautiful Moloaa Bay on the northeast shore of Kauai. Walk up a flight of stairs to enter this 1200 sq.ft. spacious, air conditioned well appointed home with an open...
Ocean View Paradise: Spacious 2-Bedroom Condo at Kaanapali Shores
Experience the ultimate Maui getaway at Kaanapali Shores 416, a beautifully maintained 2-bedroom, 2-bathroom condo that promises breathtaking ocean views. The open-concept living space seamlessly blends indoor and outdoor dining, making it easy to savor meals while...
Gratitude Bed and Breakfast BBWK2022/0001
This is a Bed and BREAKFAST, I provide you with Local food for breakfast!We are within walking distance to Wailuku town which has coffee shops, restaurants, boutiques, antique shops and Local Acting Theater. You’ll love my place because of the coziness, the vaulted...