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.
Kaanapali Alii | 414
Kaanapali Alii 414 is a luxurious ocean-view vacation rental located in the heart of Maui's Kaanapali Beach. This spacious condo accommodates up to six guests with a well-designed layout two bedrooms and an enclosed sleeping den. The ground floor location of this condo...
Comfortable Studio at The Palms with Pool, WiFi & A/C - Sleeps up to 4 guests.
Unwind in Honolulu at this welcoming studio. This modern space offers a cozy living room with a queen bed and sofa bed, perfect for a peaceful retreat on the quiet side of the property. Enjoy the convenience of amenities like pool, WiFi, AC, and a hair dryer during your...
1 Bedroom Suite, The Modern Resort & Spa, Honolulu
Enjoy the glamour of this stylish, upscale place. Enjoy Hawaii's capital in style at the Modern Honolulu! Guests have access to a variety of amenities, including a fitness center, gift shop, several restaurants, two swimming pools, full-service spa, concierge service,...
Historic Wailuku Inn: 10 Ensuite Bedrooms | Gourmet Chef Breakfast Included
Summary:Welcome to The Historic Wailuku Inn, a fully restored 1924 estate with 10 en-suite bedrooms surrounded by lush tropical landscaping and meandering plumeria-lined pathways. Wake to a chef-prepared farm-to-table breakfast, unwind on grand lanais, and explore Maui...
1 bdrm suite Mauna Loa Village
Located in Kailua-Kona next to a country club, this tranquil oasis sits away from town traffic and crowds while offering convenient access to the island’s many possibilities. it easy at this unique and tranquil getaway.The spaceThis spacious one-bedroom resort suite...
Mauna Loa Village condo in Kailua Kona with Pickleball, Pools and Tennis
Experience Kailua-Kona like a local in this 3-bedroom,2.5 bathroom condo. The bedrooms feature 1 king bed, 2nd bedroom, 2 queen beds, 3rd bedroom 1 queen bed ensuring a pleasant night's sleep for all guests. 2 master bathrooms equipped with hair dryers and showers,...
Gorgeous private home with spectacular ocean views & private pool at Kohala Ranch
Gorgeous home with spectacular views and extra privacy on 6 acres in the Kohala Ranch community. This newly upgraded dream home is perfect for couples and families looking for a spacious three bedroom home where they can relax and enjoy panoramic ocean and mountain...
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Ranch Beach Estate is a hidden Hawaiian gem,...
Walking Distance from Papaloa Beach, Outdoor Pool, Free Parking, Full Kitchen!
Step into a world of relaxation, surrounded by swaying palm trees and vibrant hibiscus blooms. Your spacious suite features a full kitchen, separate living room, and private lanai. Refresh yourself in our sparkling outdoor pools, perfect for relaxation or family fun....
Kiahuna Plantation Resort 161 Ocean View 1 Bedroom
- Second floor end unit with lanai overlooking the great lawn and out to the ocean- Walk-up, no elevators- Tropical beach décor and original artwork- Tile floors with carpet in living and bedrooms- Open kitchen includes Corian countertops and new appliances, microwave,...
North Shore Oceanfront Retreat by Gather: 5BR Spacious Home Paradise
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to North Shore Beachfront Retreat by...
REDECORATED! Like-New Oceanview 4 Bedroom 3.5 Bath Lux Montage Kapalua Grand Residence Sleeps 8!
New Offering! 5201 has just joined Private Paradise Villas as another "Your Own Private Paradise" residence to enjoy. An extensive redecoration was just completed as of July 2025. We are thrilled to welcome our first guests to this FULLY redecorated (all new!) villa...
Niu Beach Estate – Private Luxury Meets Island Sophistication
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Aloha and welcome to your own private slice of...
Kihei Estates G105 Gorgeous Remodeled Condo Home
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean, restaurants, and shops of Maui all within a couple minutes walk from this 1 bedroom 1 bath island oasis unit in the heart of Kihei. Wander right out to the well maintained grounds and...
Kolea 8E - 3 Bedroom Ocean View Vacation Rental
Kolea 8E is a three bedroom, three and a half bath villa with a sweeping view of Hualalai and an impeccable ocean view of Anaeho’omalu Bay. It is one of the few front row villas that also overlook the private Kolea Beach Club, where Kolea guests are invited to enjoy...
Kona Reef F2 – Charming Oceanfront Condo for 4!
Summary:The mesmerizing gem of Kailua-Kona is something that truly has to be seen to be believed, offering an unforgettable tropical escape for visitors from around the globe.The Space:Margo and Frank first came to the big island some 10 years ago. They came to Kona...
Kapalua Ridge Villa 1222 Ocean View 1 Bedroom
- Spacious lanai with views toward mountain, golf course, and ocean- Second floor unit, two-level townhome, with multiple stairs from parking to the villa- Tile in kitchen, and bathroom. Carpet in living room and bedroom- Fully equipped kitchen with stainless steel...
Westin Ka'anapali North Tower - Beautiful 2 Bedroom Villa in Maui - Family Friendly
The Westin Kā‘anapali Ocean Resort Villas North, nestled on Maui’s famous Kā‘anapali Beach, offers a luxurious Hawaiian getaway. Spacious villa-style accommodations include kitchens, private lanais, and upscale amenities. Guests enjoy lagoon-style pools, a...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beachfront Kaanapali Residence Club+Amenities, 3BR
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴🌺 Escape to Tropical Opulence at The Hyatt Residence Club on Kaanapali Beach! 🌺🌴𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 may provide an additional $500-$1000 SAVINGS for members on...
Fairways South #23
Located within the desirable South Fairways at the prestigious Mauna Kea Resort, this charming 4-bedroom home is adorned with exquisite Asia-Pacific decor. This beautiful vacation rental not only offers breathtaking ocean views but also provides a serene oasis to unwind...
Central HNL, Well-Established Neighborhood, Tandem Parking, Pet-Friendly!
Enjoy the best of both worlds. We offer a central location close to all the tourist attractions plus a family neighborhood with spacious yard. It is only a 5-10 min drive to Downtown and the main hospitals, and a 10-15 min drive to the main shopping centers (Ala Moana,...
Unwind in Style: Newly Remodeled Pacific Monarch with Spectacular Ocean Views!
Welcome to your new home away from home!Step into paradise with our beautifully remodeled Honeymoon Luxury Suite on the 25th-floor studio, offering mesmerizing east-facing views of the ocean that defy description. Nestled in the heart of historic Waikiki within the...
The Westin Nanea Ocean Villas | Two-Bedroom Villa
Summary:The Westin Nanea Ocean Villas maintains is situated on 16 acres of Maui's North Kā'anapali Beach and is designed to provide a relaxing haven replete with culturally inspired programs and authentic Hawaiian experiences. Depart from The Westin for a close...
Ko'Olina Hawai'i - Oahu - Ocean Front Resort - by Marriott - 2 Bd. Mountain View
In the Luxury community of Ko'Olina, on Oahu's west side, sits Marriott's Ko'Olina Beach Club. This oceanfront resort has all the amenities you expect from a world-class, luxury Marriott Resort. On-site is a spa, a health club, restaurants, bars, a sundry shop, multiple...
The Ideal Property for a Digital Nomad in Hawaii. Enjoy Paradise.
Minimum Stay: 30 DaysMaximum Occupancy: 1 GuestWelcome to my luxury home in one of America’s premier destinations! Located just a few miles from Waikiki, this stunning retreat sits atop a hill in a gated community, offering breathtaking ocean views and the soothing...
ALII PARK PLACE K202 BEAUTIFUL 3 BEDROOM WITH AC
Alii Park Place K202 offers a premium and quality living experience with a 31-night minimum stay. This beautifully furnished 3-bedroom, 2-bath unit overlooks a sparkling lagoon-style swimming pool and spa. Located on the second floor, the residence enjoys tropical...
Kiahuna Plantation Resort 33 Ocean View 1 Bedroom
- Second floor, fully renovated, end unit with ocean views and cool breezes- Walk-up, no elevators- Bright and airy tropical ambience- Carpeted living, dining and bedroom areas with tile in kitchen and bath- Fully equipped gourmet kitchen with Corian countertops and...
Kahana Villas E408 by Gather: Prime Location w/ Pool,Beach,Tennis & Sunset Views
Welcome to Kahana Villas E408 by Gather, a spacious two-bedroom, two-bathroom condo in the heart of Lahaina, HI. Located directly across the street from the beach, this condo offers a prime location and plenty of amenities to make your Hawaiian vacation...
Wailea Elua Village 2102
Wailea Elua 2102 is a delightful one-bedroom with a bonus room, two bathroom second-floor condo that comfortably accommodates up to five guests. Designed with a relaxed, island-inspired style, this residence blends casual elegance with modern comfort, creating an...
Ocean View Villa w/ Close Proximity to Ocean and Resort Amenities
This elegant, single-level ocean view villa is designed for sophisticated island living. It features a sunken living room with sliding doors for easy access between indoor and outdoor spaces, a gourmet chef’s kitchen outfitted with premium appliances, complemented by...
January-- 31 days just opened up, come whale watch!
Simply yet exquisitely designed for beachside living, Ka Momi is as close to the ocean as a home can get. This new build offers a comfortable central living/dining area & convenient kitchen with modern stainless steel appliances. Designed for optimal privacy, the two...
Discovery Bay 1 Bedroom, Ocean View, Near the Beach! Free Parking!
Wake up to breathtaking ocean views from this spacious 1-bedroom condo! Featuring a comfortable queen bed, central A/C, and all the amenities you need for a relaxing stay, including FREE WiFi, cable TV, a washer/dryer, and an assigned parking stall.Skip the hotels and...
Westin Princeville Ocean Resort VillasnOne Bedroom Villa
1 Bedroom Premium VillaWestin Princeville Ocean Resort VillasPrinceville, HawaiiLocated on the north shore of the Princeville Resort, along a cliff two hundred feet above the ocean, you might just have found your paradise. The beautiful Westin Princeville Ocean Resort...
Discovery Bay - 2 Bedroom, Parking Included - Prime Location in Waikiki!
Welcome to your island escape! This spacious 2-bedroom, 2-bathroom condo has everything you need for a comfortable stay in paradise. Fully furnished and thoughtfully equipped, you'll enjoy a complete kitchen with dishwasher and microwave, central A/C, and your own...
Maui Kaanapali Villas 293: 1 bedroom condo on N Kaanapali Beach
Maui Kā’anapali Villas #E293: Second floor 1 bedroom on N. Kaanapali Beach with Pool and Beach AccessThe space:This condominium is located in the popular Emerald building, renowned for stunning views of the pool, grounds, and people-watching. Situated on the second...
Discover Paradise at Hilton Vacation Club Ka’anapali Beach Maui – 2 Bd Villa
Set on the legendary Ka’anapali Beach, the Hilton Vacation Club Ka’anapali Beach Maui offers a dream Hawaiian getaway that’s perfect for families, couples, or friends. With breathtaking ocean views, a wealth of amenities, and a location that blends natural beauty...
Fairway Villas at Waikoloa Golf View 2 Bedroom
Golf View 2 Bedroom 2 Bath - Kitchen features granite countertops, ceramic cooktop and oven, refrigerator, microwave, dishwasher, coffeemaker, toaster, rice cooker, blender, cookware and tableware- Master bedroom with 1 king bed and master bath with large soaking tub...
Central Waikiki Beach Studio
Super location! Only 5-minute walk from famous Waikiki Beach and central to shops, restaurants, activities, and amenities. This sunny kitchenette studio has plenty to offer including partial ocean view on high floor, free assigned parking, secured elevator, and cooking...
Waipouli Beach Resort Oceanfront 1 BD 2 BA
Ocean Front 1 Bedroom 2 Bath- Spacious condo with full kitchen includes granite countertops, Wolf cooktop and convection oven, microwave, 2-drawer Fisher-Paykel dishwasher, full size Sub-zero refrigerator, coffeemaker, blender, toaster, cookware and tableware- Bedroom 1...
Canoe House at Champion Ridge - 4 Minutes to Private Mauna Lani Beach Club
Take advantage of this exclusive limited-time discount and experience the luxury of Canoe House at Champion Ridge—a breathtaking four-bedroom, three-and-a-half-bath retreat in the heart of Mauna Lani Resort. Designed by acclaimed architect Lucky Bennett, this stunning...
Private Home, Beaches, Volcano, Wi-Fi, Tv, Games, Fruit Trees
Cozy 2 bd/1ba home nestled in serene Orchidlands. We’re in 2 acres of island forestry, giving you plenty of privacy and quiet time to relax.Bedroom 1 has a King size bed. Bedroom 2 has a queen size bed with ample closet space. Phone charging ports at side tables and...
Magic Sand beach Cozy 2-bedroom Ohana in beautiful Kailua-Kona with AC, WiFi
The house is across the street from Magic Sand beach. One minute walk to the beach from our house. The Ohana is separated from the main house, which you might share the pool/spa with others if someone else rents the main house. Otherwise, you can enjoy the pool/spa...
Makaha 4 BR/2BA Ocean & Mountain Views home - 0.4 miles from Makaha Beach Park.
4 BR, 2 BA home with Ocean & Mountain views. Wake up to the fresh ocean air and splashing waves. Goats frolicking in the Waianae mountain range. Modern, clean and spacious home. Located in a quiet, well-established Makaha neighborhood just a few minutes walk from Famous...
🏝️Summer Deals-Ocean View, Great Location, Across from Kamaole Beach 2🏝️
Discover your perfect getaway at this charming one-bedroom, one-bathroom condo, ideally situated across from the stunning Kamaole Beach Park 2 in Kihei. With ocean views from the bedroom and a refreshing pool view, this property offers a serene ambiance that invites...
Westin Princeville Ocean Resort Villas" Best of the Best" 2 Bedroom
This luxurious 2 bedroom villa features 1311 sq. ft. of living space and comfortably sleeps up to 8 adults. The master bedroom is outfitted with Westin’s signature king size Heavenly Bed and the master bath features the Heavenly Bath complete with large shower, double...
Country Escape
Visit our "Country Escape" on the North Shore of Oahu and experience “Country Living” on a secluded one acre estate above Waimea Bay. Situated at the top of the Pupukea highlands, your hiking and cycling activities will be enhanced by the cool mountain air and lack...
Magic Skies Surfs Up Room
This room is large and is located on the main floor with two beds, a queen size and a full size bed, sitting area, frig, microwave, coffee, double doors lead out onto front lanai, with ocean view. Bathroom is dedicated but is also the bathroom for the living area on the...
OceanView Marriott Waiohai beach club 2BDRM villa , Full Resort Access
Welcome to Hawaii's Garden Isle, Kauai. The unspoiled terrain invites you to explore rugged cliffs, towering waterfalls and lush foliage. Marriott's Waiohai Beach Club is a superb location on the golden sand crescent of Poipu Beach, widely considered one of America's...
3 Marriott-Kauai Lagoons Beachfront Resort, Gym
Enjoy the glamour of this stylish, upscale place. Marriott Kauai Lagoons - Kalanipu'u is a secluded oasis amid this breathtaking beauty of Kauai. This master-planned community is an upscale vacation hideaway featuring more than 500 emerald acres of tropical foliage,...