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.
Wailea Ekahi Village 3C - 1 Bedroom Garden View Condo
Wailea Ekahi 3C is a captivating vacation rental that offers a truly idyllic island getaway in the heart of Maui\'s picturesque Wailea resort area. Nestled within the lush, meticulously-maintained 34 acre Ekahi Village complex, this spacious one-bedroom, one-bathroom...
Wailea Ekahi Village 39A - 1 Bedroom Garden View Condo
If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush row of towering tropical plants. This hidden gem provides a tranquil oasis perfect for unwinding after a full day exploring Maui\'s scenic...
Wailea Ekahi Village 38F - 2 Bedroom Ocean View Condo
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts panoramic ocean views. Take...
Wailea Ekahi Village 38B - 1 Bedroom Ocean View Condo
Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start your morning on the lanai with a freshly brewed cup of coffee and walk out on the sprawling grass lawn to feel the soft grass beneath your toes. Take in...
Wailea Ekahi Village 35D - 1 Bedroom Ocean View Condo
Make your Maui dreams come true at Wailea Ekahi 35D! This vacation rental is perched on the top floor with a private entrance surrounded by manicured grass lawns, colorful bougainvillea, and fragrant plumeria trees. This modern remodeled one-bedroom one-bathroom condo...
Wailea Ekahi Village 35C - 1 Bedroom Garden View Condo
Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one-bedroom, one-bathroom condo offers an ideal blend of comfort and luxury. Make use of the ground floor location to really live an indoor/outdoor...
Wailea Ekahi Village 34E - 1 Bedroom Ocean View Condo
Wailea Ekahi Village 12E is a delight to the senses. A vibrant row of Bougainvillea and the sweet smell of plumeria welcome you to this picture-perfect Maui vacation rental in the heart of Wailea. Once inside Wailea Ekahi 12E, you will be immediately drawn to the...
Wailea Ekahi Village 30D - 1 Bedroom Ocean View Condo
Nestled in the prestigious Wailea Ekahi Village, condo 30D is an exquisitely decorated island-inspired vacation rental that offers a perfect blend of luxury and comfort with breathtaking ocean views. The lanai provides an idyllic setting for outdoor dining or morning...
Wailea Ekahi Village 29D - 1 Bedroom Ocean View Condo
This Wailea Ekahi Village residence completed a beautiful renovation in 2022. From colorful artwork to comfortable and sleek furnishings, you will instantly recognize why this Wailea vacation rental earned our highest internal ranking of \'\'platinum\'\' status. This...
Wailea Ekahi Village 25D - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 25D, an exquisite vacation rental that embodies the essence of luxurious island living in Wailea. This one-bedroom, one-bathroom second-floor condo offers a enjoys elevated views of the 32-acre manicured grounds. Vaulted ceiling and tiled floors...
Wailea Ekahi Village 23C - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you a relaxing, island-inspired retreat. Nestled within 34 acres of lush tropical landscaping, 23C is a ground-floor...
Wailea Ekahi Village 19B - 2 Bedroom Ocean View Condo
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired décor, creating a cozy and inviting atmosphere perfect for families or...
Wailea Ekahi Village 12C - 1 Bedroom Ocea View Condo
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers a perfect blend of comfort and tropical elegance, making it an ideal retreat for those looking to escape the hustle and...
Wailea Ekahi Village 11C - 2 Bedroom Garden View Condo
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a private lanai and en suite bathroom. Many guests return to this condo year after year for its close proximity to the pool...
Wailea Ekahi Village 10F - 1 Bedroom Garden View Condo
Wailea Ekahi Village 10F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo is part of the Wailea Ekahi Village, a low-density community set across 34 acres of meticulously landscaped tropical gardens. The condo...
Polo Beach Club 801 - 2 Bedroom Oceanfront Condo
Perched on the top floor, this vacation home offers breathtaking views and a touch of sophistication. The spacious kitchen, featuring a central island, provides ample room for culinary creativity while allowing you to enjoy the company of guests in the open living area....
Polo Beach Club 409 - 2 Bedroom Oceanfront Condo
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out front and stunning ocean...
Polo Beach Club 407 - 2 Bedroom Oceanfront Condo
Polo Beach Club 407 is a premier oceanfront vacation rental located in the upscale resort area of Wailea. This two-bedroom, two-bathroom condo offers guests a luxurious and comfortable stay with sweeping ocean views and direct beach access out front. If looking for the...
Polo Beach Club 301 - 2 Bedroom Oceanfront Condo
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies the indoor-outdoor lifestyle that Hawaii is famous for, making it perfect for both entertaining and relaxing with friends...
Makena Surf F306 Beachfront Resort - 2 Bedroom Oceanfront Condo
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the refreshing ocean breezes beneath the cathedral ceilings while taking in the stunning ocean views. This residence boasts...
Makena Surf F208 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor, this 1,313 square foot residence is designed to provide the ultimate in comfort and relaxation, featuring elegant touches...
Makena Surf F206 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf F206 is a delightful retreat for your Maui vacation.The interior design features a harmonious palette and finishes that highlight organic beauty. The calming ambiance is enhanced by subtle Venetian plaster walls, cool travertine tile, and plush carpeting,...
Makena Surf F109 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf F109 is a stunning oceanfront vacation condo that places you just steps away from the beautiful shores of Maui. With nothing but a lush patch of green grass separating you from the ocean, this ground-floor unit offers breathtaking views that you can enjoy...
Makena Surf C207 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf C207, a vacation rental nestled in paradise. This spacious suite offers a serene escape, featuring two large lanais surrounded by the sweet scent of Plumeria. Unwind after a day at the beach by relaxing with friends and family, engage in a...
Makena Surf B106 Beachfront Resort - 2 Bedroom Oceanfront Condo
Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean\'s edge. This beautifully appointed residence combines luxury and comfort, featuring elegant tray ceilings, exquisite wood cabinetry, and...
New Luxury Listing: Where Sweeping Ocean and Coastal Views Meet Elevated Island Living
Limited Time Introductory Rates! Property Highlights • Luxury one-bedroom, two-bath townhouse, fully remodeled with refined finishes • Expansive ocean, coastal, sunrise, and golf course views from both levels • Enjoy two spacious lanais complete with outdoor dining and...
Sugar Mill Shore, 2 Kitchens, A/C, Modern Finishes
This charming North Shore property offers a versatile layout perfect for multi-family vacations or groups of friends. The main house, private mother-in-law unit, and a separate bunkhouse with four twin beds offers the perfect balance for multi-family or group stays. The...
New Listing! Cozy condo with partial ocean views!
Aloha and welcome to your slice of paradise at Kaanapali Shores 309! This beautifully appointed 1-bedroom, 1-bath condo is perched on the 3rd floor of the sought-after Kaanapali Shores Resort, nestled right on the golden coastline of West Maui. Perfect for couples or...
Kona Reef A1: Ocean-view 2BR condo in Kailua-Kona, perfect for 4-6 guests.
Newly renovated 2-bedroom, 2-bath ocean / beachfront condo, AC throughout home. Short walk to Kona town bars & restaurants. Snorkel, swim, or surf right in front of the condo. Enjoy the parade of activities in the ocean and on shore from the comfort of the lanai couch....
Aloha and welcome to our family friendly home of 50 years!
Located a 5-minute walk from Kamaole Beach III; our 1200 square foot condo can accommodate up to 6 people comfortably and is our little piece of paradise.The open concept living space includes a kitchen equipped with all the amenities; a dining table for all six guests...
Waikoloa Colony Villas 1404 Townhome, Central AC & Resort Amenities!
Discover the charm of Waikoloa Colony Villas, one of the Kohala Coast’s best-kept secrets for its live-ability, privacy, and exceptional value.This two-story 2-bedroom, 2.5-bath townhome offers 1,446 sq. ft. of interior living space, soaring 18’+ ceilings, and an open...
New Listing! Akahi C613 – Ocean View Top Floor Condo, Newly Updated, Sleeps 4
Welcome to Kihei Akahi C613, a beautifully refreshed top-floor condo with ocean and sunset views. Newly updated in October 2025 with modern furnishings, fresh paint, refinished tile floors, and a brand-new ductless AC system, this stylish retreat offers comfort and...
Waikiki Stay 1 BR w/Kitchen, 2 blocks from the beach
Perfect for families or groups, this unit sleeps up to 5 with a queen bed, sofa bed & a rollaway. Enjoy a full kitchen, open living area, and unbeatable location—just a short walk to Waikiki Beach, shopping & dining.- Flexible Sleeping Arrangements – The space includes...
NEW | KBM Resorts | FREE CAR | Kapalua Bay Villas | Ocean View | 1-Bedroom condo steps to beach with spacious lanai! KBV-24G3
** 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...
Bali Hai Resort 1 Bedroom w/ HOT TUB & POOL
Perched atop the cliff terrain of Princeville, adjacent to the renowned Makai golf course, seamlessly integrates natural beauty with carefully crafted amenities. Surrounded by the lush, tropical mountains of the north shore, the resort offers a harmonious blend of...
Cozy Waikiki Apt with FREE parking sleeps 4
Cozy studio apartment loaded with amenities to make you feel at home while on vacation. The space can best be described as a hotel room with a small kitchen. This apartment is located in the heart of Waikiki. -parking is included (if paid separately would be at between...
B2 Poipu Makai: Cruise-ship view-AC-Whale Watch
Breathtaking up close and personal ocean views in this rarely available OCEAN FRONT Poipu Makai Condominium! One of the few condos in Poipu with covered parking. Experience the ultimate island lifestyle in this stunning 2-bedroom, 2-bathroom Oceanfront 2nd-floor condo...
Hale Hui Kai By Parrish Kauai - Central Poipu Location
Welcome to Hale Hui Kai, your Gathering Place by the Sea. This spacious three-bedroom plus den retreat in the heart of Poipu Beach Estates. Designed for families and friends to come together, this inviting home combines the ease of island living with modern comforts,...
Ko Olina Resort - Inquire re: Discount!
Welcome to this brilliant townhome in Ko Olina Resort Community. This peaceful retreat offers 3 cozy bedrooms, including 2 king beds and 2 full bed. With AC and heating, guests can relax in comfort. It's easy to see why you'll be able to unwind at our place.Enjoy...
Seaside Escape Just steps to the Beach!
Breaking News! Iconic, cultural, and beautiful Maui is back in business. We are proud to be welcoming guests to our legal vacation rental which has a full kitchen and is far more affordable than the pricey hotels and resorts. Thank you in advance for showing your...
"Waimea Vista," Oceanfront Views, Walk to Beaches
Vrbo Premier Host presents: Oceanfront with sweeping views of surfers, whales, and sunsets. This 3-bedroom retreat sits within a marine sanctuary, offering rare privacy and walking distance to three iconic beaches, world-class snorkeling, local eats, grocery. Endless...
Lahaina Shores Maui Dream Oceanfront Ocean Views
Your Maui Dream Awaits! Oceanfront Condo in LahainaImagine waking up to the gentle rhythm of the waves, stepping onto your private lanai, and being greeted by breathtaking, unobstructed views of the Pacific Ocean. This isn't just a dream – it's your next vacation at our...
Lahaina Shores Oceanfront Ocean Views Oasis
Oceanfront Oasis: Stunning Views, Steps to the SandEscape to our beautiful oceanfront studio condo, where the rhythmic sound of waves will be your daily soundtrack. This newly renovated studio retreat offers the perfect blend of luxury and location, putting you just...
3-bedroom townhome in peaceful Ewa Beach with AC
Enjoy a peaceful stay at this charming 3-bedroom townhome in Ewa Beach. This terrific property features 2 queen beds, 1 twin bed, and a cozy office space with a futon. With amenities like AC, iron, and a hair dryer, guests can relax and escape close to the ocean in this...
New Listing! Poipu Townhome with Resort Amenities
Poi'pu Townhome with Lanai, Pool and Gym Experience island living at this lovely Pili Mai townhome in Poipu, surrounded by Kiahuna Golf Course with breathtaking mountain and South Shore views. Elegant design meets tropical paradisePremium Location and Resort...
Newly Renovated Waikiki 2BD 2BA Ocean City View
Summary:Aloha! Experience the best of Honolulu in this fully renovated apartment at 444 Niu Street. Enjoy the convenience of a full kitchen, partial ocean views, and free garage parking. With two bedrooms and two bathrooms, this apartment is perfect for a relaxing...
Nihilani 18C Newly renovated plantation style home
Located on an upper floor and a corner unit .... this newly renovated and elegantly furnished town home will comfortably accommodate your family. Nihilani 18C features central air conditioning and garage parking. Sit on your lanai with a tropical beverage and enjoy the...
PK K207 Relaxing Maui 1BD Condo w Pool & Beach
Papakea K207 NEW LISTING Relax on Maui at this 1Bedroom, 1Bathroom, Just Steps from the Pool and Beach! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel...
Guesthouse in quiet Pāhoa St with AC
Come stay in our charming guest house and experience the beauty of Hawai‘i’s Puna side. Our little ‘ohana offers a peaceful place to relax, surrounded by tropical greenery, yet it’s just a short drive from black sand beaches, Hawai‘i Volcanoes National Park, and...
Poipu Retreat: 3BR with Ocean & Golf Views, Lanai Sunsets, Pool & Central A/C
Welcome to Pili Mai 8C – Your Private Poipu Retreat.Perched on the edge of the scenic Kiahuna Golf Course, Pili Mai 8C is a three-bedroom, three-bath condo that captures the very best of Kaua‘i living. With sweeping views of the ocean, golf greens, and surrounding...