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.
Kailua Beachfront Estate by Gather: Beachfront Luxury w/ Pool, Spa & Guest House
Welcome to Kailua Beachfront Estate, an exceptional 7-bedroom, 6.5-bath sanctuary that sleeps up to 14 guests on O'ahu’s most exclusive stretch of sand. Blending timeless coastal architecture with luxurious modern amenities, this 5,902-square-foot residence offers the...
Kiahuna Plantation Resort 161 Ocean View 1 Bedroom
Gaze out at the Pacific from this 2nd floor ocean view condo, just steps from Kauai’s most iconic beach. A perfect blend of comfort and scenery, ideal for couples or small groups. Unit 161 Ocean View 1 Bedroom 1 Bath• Fully equipped kitchen includes full size...
Terrific 2-bedroom condo in Kapaʻa
Aloha and welcome to Paradise. We feature a boutique resort with an old Hawaii feel right in the middle of all the action. We are a 2 bedrooms, 1 and 1/2 bath duplex townhome, sleeping 6. Featuring a King bed in the upstairs master with a balcony to see the ocean, a...
REDECORATED! Like-New Oceanview 4 Bedroom 3.5 Bath Lux Montage Kapalua Grand Residence Sleeps 8!
New Offering! 5201 recently joined Private Paradise Villas our newest "Your Own Private Paradise". An extensive redecoration was just completed as of late 2025. We are thrilled to welcome our first guests to this FULLY redecorated (all new!) villa boasting expansive...
Niu Beach Estate – Private Luxury Meets Island Sophistication
Welcome to Niu Beach Estate, a breathtaking 5-bedroom, 5.5-bath modern plantation retreat set along the peaceful southern shores of Oʻahu. Spanning an expansive 7,711 sq ft of indoor–outdoor living, this newly remodeled estate blends contemporary coastal luxury with...
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...
Westin Kaʻanapali North 1BR Premium – Island Retreat
Discover your perfect Maui escape in this 1-Bedroom Premium Island View Villa at The Westin KÄÊ»anapali Ocean Resort Villas North. Offering approximately 750–900 square feet of space, this villa is ideal for couples or small families, with thoughtful details that make...
Oceanfront Villa on Kona Coast with breathtaking views
Your home away from home in the Mauna Lani Beach Resort with 5 bedrooms, 7 beds and 9 bathrooms. This villa offers guests a relaxing retreat with an outdoor oasis with 2 pools, 2 spas, and modern amenities like WiFi, a fitness room, and AC. The 9 bathrooms ensure...
Luxury suite overlooking Waikiki skyline with Ocean View, FREE Parking!
Allure Waikiki #2702 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches throughout features...
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 the...
Kapalua Ridge Villa 1222 Ocean View 1 Bedroom
Nestled on a gentle slope, this Ridge Villa boasts beautiful ocean views and a calm atmosphere. Located within Kapalua Resort, it’s perfect for those looking to unwind in style.Ridge Villas #1222 1 Bedroom Ocean View• The Ridge Villas are perched high above the ocean...
Spacious 5-bedroom house with WiFi, fitness room in enchanting Keaau
Discover the beauty of Keaau from this 5-bedroom house. With 1 king bed, 2 queen beds, 1 child bed, and 1 crib, this terrific property offers plenty of space for guests. Enjoy the convenience of a washing machine and dryer, WiFi, fitness room, heating, AC, and more....
Fairways South 23 Four Bedroom
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...
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...
Always a Great Idea To Unwind! 2 Comfortable Units, Outdoor Pool, Oceanfront!
When it comes to comfort, convenience, and an aloha spirit - you found the right place to stay. Relax by the pool, indulge in our buffet dinner, and enjoy views out over Kahului Bay. All this is yours within 10 minutes of the airport, and you'll be close to many of the...
Incredibly roomy, adjacent to the best beaches/Wailea
Extremely roomy, high-end 1-bedroom 2-bathroom, deluxe 1039 square feet condo at the gateway to Wailea. Remodled and features a king bed, high-end furnishings, and a sofa bed. The property has two pools, two hot tubs, two tennis courts and lush gardens. Home boasts...
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: 2 guestsWelcome to my luxury home in one of America’s premier destinations. Located just a few miles from Waikiki, this beautifully appointed retreat sits atop a hill in a secure, gated community, offering sweeping ocean views and...
Aqua Aloha Surf Waikiki 1505 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1505 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed, (1) Queen sofa sleeper, sleeps 4, 365 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Extra Large Lanai | 2 Units, 5 Bedrooms | HK ML-1904
** 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...
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
Wake up to panoramic ocean views in this charming 2nd floor condo, just steps from the sands of Kauai’s iconic beach. A peaceful, fully equipped retreat for up to four guests. Unit 33 Ocean View 1 Bedroom 1 Bath• Fully equipped kitchen includes full size refrigerator,...
Oceanfront Studio with Panoramic Views - Kapa'a Sands 09
Wake up to panoramic ocean views in this charming second-floor studio nestled in a quiet, boutique-style property right on the shoreline. Surrounded by lush gardens and cooled by trade winds, this unit features a full kitchen, private lanai, and access to a pool, BBQ...
4th Fl Marine Surf Studio | Corner Unit | Parking
Stay in comfort and style within walking distance of the International Market Place, restaurants, shops, and Waikiki’s vibrant nightlife. This bright corner studio is ideally located in the heart of Waikiki and includes one free parking stall—a rare bonus in this area!🏠...
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 comfortable retreat offers a prime Maui location and resort-style amenities for a relaxing and...
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 a...
Ocean View 1BR Premium Villa at Westin KÄÊ»anapali North
Wake up to the beauty of Maui’s coast in this 1-Bedroom Premium Ocean View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering 750–900 square feet, this spacious villa is ideal for couples or small families seeking a blend of comfort and luxury with...
Maui Resort Rentals: Marriott's Maui Ocean Club Studio Oceanview Suite
Freshly Renovated Studio Oceanview Suite at Marriott's Maui Ocean Club. Marriott’s Maui Ocean Club is a full-service resort with everything needed for a fabulous stress-free vacation. Amenities include mid-week clean-up service, pool towel service, exercise facilities,...
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...
Hale Ho'omaha • Relaxation • Short Walk to Beach
This home is our passion project, with thoughtful improvements ongoing. Located in Kaaawa near Kualoa Ranch, it offers a peaceful setting with mountain views, nearby beaches, and a slower pace to unwind. The space is clean, comfortable, and intentionally simple, ideal...
Cozy Yurt retreat on a Coffee Farm in Holualoa. 8 mn from the Beach & shopping
Located at 1200 ft elevation. Does not require AC nor heat as it always has the perfect temperature. Experience living in yurt nestled among the coffee trees. You can enjoy your coffee out on the deck while listening to the birds or watching the magnificent...
Aloha Vibes Road to Hana explorer
Immerse Yourself in the Aloha Spirit with Our Cozy Camper Van!Experience Maui like never before in this ultra-comfortable, fuel-efficient camper van—perfect for two adventurous travelers looking to relax, explore, and embrace island life. With all the essentials and...
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | Large Master Suite | 3 Units, 4 Bedrooms | ML-2041
** 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...
Fairway Villas at Waikoloa Golf View 2 Bedroom
Enjoy beautiful golf course views from this bright two-bedroom condo on the scenic Kohala Coast. Lots of room to relax and unwind and ideal for exploring the Big Island’s beaches and natural beauty. Golf View 2 Bedroom 2 BathFairway Villas is located at 69-200...
Central Waikiki Beach Studio
5-min walk to Waikiki Beach from this sunny high-floor studio with partial ocean view and private balcony.Rest on a new queen pillow-top bed, stay connected with fast Wi-Fi, and cook in the stocked kitchenette.Enjoy free assigned parking, secure elevator access, self...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢'𝐬 Luxury Beachfront Kaua‘i Club Resort + Amenities
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 2-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at the 𝐥𝐮𝐱𝐮𝐫𝐢𝐨𝐮𝐬 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐊𝐚𝐮𝐚𝐢 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛 — perfect for families or friends seeking a luxurious escape on 𝐊𝐚𝐥𝐚𝐩𝐚𝐤𝐢 𝐁𝐞𝐚𝐜𝐡.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞...
Waipouli Beach Resort Oceanfront 1 BD 2 BA
Relax in this oceanfront one-bedroom condo, where the waves are your backdrop. Perfect for a couple’s retreat; with an open concept living space and a lanai that brings the ocean right to your doorstep.Oceanfront 1 Bedroom 2 Bathroom• Kitchen features granite...
Spacious, family friendly Waikomo Streams condo with pool - walk to Baby Beach
Waikomo Stream Villas 131Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your tropical paradise in Poipu, HI! This charming condo is nestled amidst lush landscaping and...
Napili Point | 2 FREE Rental Cars | KBM Resorts | Water Front | 2 Units, 2 Bedrooms | NAP ML-2525
** 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...
Canoe House at Champion Ridge - 4 Minutes to Private Mauna Lani Beach Club
Experience the luxury and tranquility of Canoe House at Champion Ridge, a breathtaking four-bedroom, three-and-a-half-bath retreat within the prestigious Mauna Lani Resort. Designed by acclaimed architect Lucky Bennett, this single-level residence seamlessly blends...
Cosy Room next to Waikiki
Come relax and enjoy easy access to everything located in Waikiki. Located next to Waikiki close to all the great hotspots Oahu has to offer. This is a private room in a two bedroom townhouse. Lots of public transportation, restaurants and grocery stores all less than a...
Indulge in Home-Like Comfort! 3 Comfortable Units, Outdoor Pool, Oceanfront!
When it comes to comfort, convenience, and an aloha spirit - you found the right place to stay. Relax by the pool, indulge in our buffet dinner, and enjoy views out over Kahului Bay. All this is yours within 10 minutes of the airport, and you'll be close to many of the...
🏝️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...
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 of...
Makaha Villa by AvantStay | Mountain + Ocean Views
Makaha Villa is your Oahu haven perched in a prestigious gated enclave within the scenic Makaha Valley. This sunny home boasts four bedrooms, a beautiful outdoor space with mountain and ocean views, and a 7-minute drive to Makaha Beach.Nestled in a cul-de-sac, you'll...
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...
Kaanapali Alii 425
Kaanapali Alii 4252 Bedroom | 2 Bathrooms | Sleeps 6 | Garden View________________________________________Welcome to Kaanapali Alii 425, a stunning two-bedroom garden view condo in Maui’s exclusive Kaanapali Alii Resort. This 1,807-square-foot residence offers serene...
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...
Alii Villas#322 Stunning & Special Top Floor Condo with Ocean Views
Alii Villas 322 – Incredible Top Floor Ocean View RetreatWelcome to one of the most unique and desirable units at Alii Villas. Perched on the top floor, this beautifully appointed 1-bedroom, 1-bathroom condominium offers a private retreat with sweeping ocean views that...
Panoramic Views | Balcony w/ Full Building Access
This bright studio is like a 1-bedroom, 1-bath vacation unit located in the heart of Honolulu. Enjoy ocean and city views from your private balcony, with easy access to a community pool, resort shops, and cafés—plus all the perks of a modern, open-concept layout filled...