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.
Ocean View Large Lanai Kamaole Sands
Hosted by VacaMauiLuxurious Condo at Kamaole Sands: Your Perfect Maui Getaway!Welcome to Kamaole Sands, your ultimate destination for a dream vacation in Maui! Our exquisite condo, located in Building #8, Unit #411, offers everything you need for a memorable stay....
Ocean Views | Polo Beach Club Ground Floor Condo | Walk to Beach, Private Patio
Summary:Escape to paradise at this ground-floor condo at the exclusive Polo Beach Club. Enjoy stunning ocean views, lush gardens and direct access to Wailea’s premier swimming beach. The “endless lanai” allows you to step straight onto the pool, beach or scenic...
Waterfalling Estate is an oceanfront compound on the Big Island unlike any other
Waterfalling Estate is an oceanfront compound unlike any other on the Big Island. Nestled clifftop along the breathtaking Hamakua Coast, this hideaway boasts a private 85-foot waterfall, an Olympic pool featuring a two-story waterslide, spa, fully loaded custom gym,...
#37 - Stunning Unit with Ocean View
This condo sits OCEANFRONT on the Sea Mountain Resort at Punalu'u Black Sand Beach. It is a spacious one-bedroom unit, fully furnished with laminate and ceramic tile floors throughout. The uniqueness of this Polynesian style condo with a modern flair is that it is a...
Coconut Plantation by AvantStay | Resort Access, 0.4mi Walk to Beach!
Please note that this home is available for 28+ night stays only.Aloha from Coconut Plantation! Immerse yourself in the island lifestyle at this stunning two-story condo, surrounded by swaying palm trees and lush tropical landscaping. With 4 bedrooms and 3 full...
Ho’okipa Hideaway - North Shore, Walk to Cafe
This North Shore Maui Hideaway has its own private entrance, a charming private garden, cozy queen bed and off-street parking for one car. An attached covered and enclosed screened porch with two overstuffed lounge chairs looks out onto the beautiful private and gated...
Fairway Villas At Waikoloa Beach Resort#I24: Gorgeous Top Floor 2 bedr/2 Bath
Welcome to your paradise retreat tucked away in a serene enclave of Fairway Villas at Waikoloa Beach. This villa offers a haven where you and your guests can unwind amidst gentle breezes and breathtaking views. This clean and attractive villa has attractive decor &...
Gorgeous Ocean View! Steps to Beach! Centrally located, full kitchen & more!
Waikiki Shore #712 – 2161 Kalia Rd.Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sand of Waikiki Beach!You'll be mesmerized by the incredible ocean views from this beautiful Hawaiian feel contemporary. The open concept...
Experience Tropical Tranquility: Luxury Studio Home in Hilo!
Experience convenient and comfortable living staying at our studio in our newly built duplex home. Located centrally in Hilo. You will be just 3 miles from Hilo airport, Liliuokalani Park and Garden, Carlsmith Beach Park, and many other popular attractions and...
(4102/03) 2Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 2 bedrooms, one with a King size bed and large en-suite bathroom with a shower to rinse off after a day...
(4101/02/03) 3Br Ground Floor Hanalei Bay Resort, Ocean View, Pool, Tennis
Welcome to Hanalei Bay Resort unit 4101/4102/4103. A ground floor unit with stunning views of Hanalei Bay and the surrounding Bali Hai Mountains. This beautiful unit has 3 bedrooms, 2 of which have King size beds and two large bathrooms with showers to rinse off after a...
Ala Moana Hotel 13th FL R0 Studio - 2Double Beds 4Person
NEWLY RENOVATED 13th floor with Partial Ocean ViewCozy Hotel Studio | 2 Beds | 1 Bath | Sleeps 4 Stay in the heart of paradise! This bright and comfy studio is perfect for friends or family, with 2 beds, 1 bath, and space for up to 4 guests. Just steps from Ala Moana...
Your Storybook Tropical Island Escape at Anini Beach- TVNC 1361
Tucked beneath swaying palms and just steps from the gentle turquoise waters of Anini Beach, this enchanting one-bedroom cottage is pure island charm. With its vintage flair and dreamy, movie-set vibes, it’s the perfect hideaway for romantic retreats, solo escapes, or...
Kihei Holiday Stunning Ocean View #309 2bd/1ba condo, 1 min walk to the ocean.
***Notice (July 2025) regarding Short Term Rentals on Maui: Kihei Holiday Condominium is legally zoned (H-1/H-M) for short term vacation rentals and is not affected by the new rules in Maui County for many other properties! Your booking is safe with us!!!Maui Ocean...
Chic & Upscale Waikiki Beach Ocean View w/ Parking
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...
Ground floor Condo with private golfside lanai, and views of golfcourse
The Golf Villas at Mauna Lani E3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Promotion Announcement: Complete your reservation and leave a review between May 1 and December 31 to...
Luxe Private Princeville Retreat Near Hanalei Bay!
Delight in the very best of Kauai from the comfort & convenience of this spacious private retreat! Perfectly situated in the heart of Princeville just minutes to Hanalei Bay, enjoy relaxing on Anini Beach, a round of golf at Makai Golf Club & luxury resorts simply a...
Oceanfront condo with resort amenities, stunning views, and top-notch comfort
Ali'i Cove Y1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience luxury living in this stunning condo located in the exclusive Ali'i Cove Condominium complex in Kailua-Kona,...
Elegant 3BR Pili Mai 12A w/ Pool, Golf Course Views & Modern Amenities
Welcome to Pili Mai 12A by Gather, the perfect three-bedroom, three-bathroom condo in Koloa. This ground-floor condo, alongside the picturesque Kiahuna Golf Course, offers garden views and a newly designed layout with central air conditioning. Each of the three...
Spectacular Oceanfront Luxury- Between Kam1 & Kam2 Beaches - Royal Mauian #511n
Royal Mauian #511 – Upgraded Oceanfront ComfortRoyal Mauian #511 offers a beautifully upgraded retreat in one of South Kihei’s most desirable oceanfront properties. This two-bedroom, two-bathroom condo combines modern design, stylish finishes, and the comforts of...
🏖️Hawaiian Unit Nearby Beaches, Restaurants, & Shopping | Concierge Included
vrKCV - Kolea 15L, Professionally Managed by Kona Coast VacationsWelcome to Kolea 15LA luxurious haven within the renowned Kolea community, located in the heart of Waikoloa Beach Resort on the stunning South Kohala coast. This exclusive residential gem offers direct...
❤️PiH❤️ BIG ISLAND OASIS ★ Family Fun! ★ Free 2026 Hilton Passes ★ Ping Pong & Bikes
Big Island Oasis brought to you by Paradise in Hawaii Luxury HomesWelcome to our Big Island Oasis at KaMilo, a spacious and beautifully appointed four-bedroom retreat on the Big Island of Hawaii. With room for up to ten guests, this home provides the perfect setting for...
Cozy Ko Olina Kai 1061F: 2BR w/ Open-Plan Living, Private Lanai & Spa Access
Nestled within the tranquil Ko Olina Resort, Ko Olina Kai 1061F by Gather is a beautifully designed ground-floor villa that embodies the spirit of island living. With two bedrooms, two full bathrooms, and 1,144 square feet of comfortable interior space, this...
Includes Mauna Lani Beach Club. Fairways at Mauna Lani 201
Fairways at Mauna Lani 201. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedMauna Lani Beach Club Pass: Your stay will include a pass card to the private parking area for...
Wyndham Bali Hai Villas | Three 2BR/2BA Villas!
Summary:This listing is for three 2BR/2BA suites at Club Wyndham Bali Hai Resort in Princeville, HI. Live Suite guests will have access to all resort amenities. Each suite sleeps up to 6 guests. - Photos are stock photos provided by the resort. Your suite may vary...
Maui Beachfront Paradise with AC, Beach gears, Snorkel, Surf, Pool & BBQ
Free Parking | Free WiFi | No Resort FeesWelcome to your dream Maui getaway! Our stunning beachfront corner unit condo on Kahana Beach offers breathtaking panoramic ocean views with floor-to-ceiling windows and doors, filling your space with endless blue horizons. Relax...
Ukulele Oasis @ Kiahuna l AC l Family-Friendly l Beach Amenities l Ground Floor
Welcome to Ukulele Oasis at Kiahuna Plantation! New A/C Unit New King Bed Ground Floor/End UnitFamily-Friendly New Sofa Sleeper Beach AmenitiesAt Ukulele Oasis you’ll enjoy an unforgettable family-friendly vacation immersed in the island spirit in your private oasis.Our...
❤️PiH❤️ Mauna Kea Palms ★Ocean Views★ Stunning Mauna Kea Resort ★ Best Beaches
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Mauna Kea Palms, a part of our Hawaiian Luxury Collection. Mauna Kea Palms at the Mauna Kea Resort Kumulani complex has majestic views of golf, mountains and sea. You will be mesmerized looking at the ocean...
Cozy Room with Kitchenette in Waikiki
This cozy room is perfect for couples or solo travelers looking for a comfortable and convenient stay in the heart of Waikiki. With a fully equipped kitchenette, free WiFi, and a smart TV with access to streaming services, you`ll have everything you need for a relaxing...
Luxury Laie Beachfront Estate w/ Private Pool, Spacious Living & Ocean Access
Welcome to Laie Beachfront Estate by GatherExperience the beauty of Oahu’s North Shore at Laie Beachfront Estate, a luxurious oceanfront retreat where contemporary island design meets timeless comfort. Nestled along a half-mile stretch of soft, swimmable white sand,...
Poipu Sands 126 By Parrish Kauai
Our luxurious Kauai vacation rentals at Poipu Sands offer spacious layouts, large covered lanais, a private heated resort swimming pool, community gas BBQs, on-site tennis courts, and more.Centrally located in Poipu, adjacent to the Grand Hyatt Resort & Spa as well as...
Breathtaking Ocean Views! Beach Front Luxury Penthouse, Polo Beach 2 Bed/2 Bath
Indulge in the ultimate Maui experience at this top-floor, direct oceanfront penthouse. Unit 804 boasts a brand-new, high-end luxury remodel and furnishings. There are unparalleled views of the Pacific Ocean and three picturesque islands: Molokini, Lanai, and...
Kuleana Club #513-Oceanview -1 bd & 1 ba-3rd Floor
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a 3rd floor ocean view condo, only steps to the ocean, surrounded by a plush Hawaiian garden. Enjoy...
Kuleana Club #107-Oceanfront Deluxe 1 bed &1 bath
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. These units are deluxe ground floor oceanfront condos, only steps to the ocean, and surrounded by a plush Hawaiian...
Waterfront condo with shared pools, private beach, balcony, W/D, and AC
Casa De Emdeko A317Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched on the top floor, this stunning 2-bedroom, 2-bathroom condo in Kailua-Kona offers sweeping ocean and...
Penthouse Condo with breathtaking views and conveniently located
Hololani B-802Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched in the heart of the west side of Maui, this stunning penthouse condo offers a luxurious ocean view retreat with...
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...
Kapalua Golf Villa, fresh updates and fairway view
Welcome to Kapalua Golf Villa 20V1, a luxurious 1-bedroom, 1.5-bath condo that can accommodate 4 guests and is located in the prestigious Kapalua resort, offering the perfect blend of elegance, comfort, and breathtaking natural beauty. As you enter the villa, you'll be...
Ultimate Oceanfront Luxury - Polo Beach Club #706 in Wailea, Maui
Polo Beach Club 706 is an ideal home base for your tropical getaway. Make your Maui experience one to be remembered. Whether you’re celebrating with family, vacationing with friends, or simply seeking a peaceful and private alternative to a high-end hotel, our luxurious...
Sans Souci 1106 🕶 Gold Coast Seaside Studio above the Beach 30+Nights
You'll find bicycles, golfing, and more on site at this smoke-free apartment. Waikiki Beach and Kaimana Beach are just a short walk away, so leave your car at the property, which offers covered onsite parking. After you return, unwind on the balcony and enjoy the...
2 bedroom home minutes to world class beaches, surf, scuba, snorkeling & golf!
Welcome to Puako Kai Hideaway, a beautifully updated vacation home in charming Puako. Located only minutes away from world class beaches, surf, scuba, snorkeling and golf. Extensive resort amenities, restaurants, shops and farmers markets are a short drive away.This...
Amazing 4th floor Oceanfront 3 bd/ 3bth condo!
Welcome to Papakea! Located on the ocean between the Kaanapali and Kapalua world-class golf resorts and minutes from shops, restaurants, and galleries. Papakea is a 13 acre oceanfront resort with the true aloha feeling of Maui. Our oceanfront unit is F406, a fourth...
Ocean Pearl: Luxurious Kahuku Retreat
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...
Luxurious Beachfront Condo with Modern Amenities - Makena Surf Resort #E-203
Makena Surf E203Welcome to Makena Surf E203, a beautifully remodeled luxury condominium within the prestigious Makena Surf Resort. With breathtaking ocean views, modern interiors, and access to exceptional resort amenities, this unit is the perfect retreat for your Maui...
Relaxing Beachfront Retreat - Sugar Beach #235 - Your Perfect Getaway!
SUGAR BEACH RESORT, #235Welcome to Sugar Beach Resort #235, a beautiful second-floor condo with stunning beachfront views. Perfectly located in North Kihei, this oceanfront retreat offers modern comforts, central AC, and the serene atmosphere of Maui’s longest stretch...
Hale O Imi Loa 3br 2ba Cute PrincevilleCottage
Welcome to Hale O Imi Loa. This 3br 2ba home has been in Princeville since 1986 and is a local treasure. Recently remodeled, the owners of this home have taken great care to ensure that guests can enjoy a beautiful Hawaiian Vacation here at the home dedicated to their...
Brand Newly Remodeled Luxury 2 BR-Kapalua Golf Villas 11P7-8
This is a legally permitted vacation rental according to the County of Maui ordinances.Your Ocean-View Escape in Kapalua – Luxury Condo with Lanai, Golf Course Views & Resort Pools E komo mai (welcome) to your dream Hawaiian getaway, where every moment is infused with...
❤️PiH❤️ HOKU LANI HOUSE ★ Heated Private Pool & Spa ★ Hapuna Park Waterslide ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hoku Lani House a brand new exquisite 4 bedroom, 4 1/2 bath home located in Hapuna Estates within the Mauna Kea Resort. Prepare to embark on a truly remarkable escape where luxury, comfort, and natural beauty...
BEAUTIFUL 2bed/2bath Oceanfront Condo
This 2 bedroom, 2 bathroom condo located on the ground floor, offers majestic ocean views and is fronting a beautiful golden sandy beach. Fully finished and equipped with everything you need in your home away from home, this is the perfect spot to enjoy with your...
Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split AC
Welcome to Wailea Ekahi 39E, a beautifully appointed one-bedroom, two-bath condo offering breathtaking ocean views and the perfect blend of comfort, style, and convenience. Whether you're planning a romantic retreat, a peaceful solo vacation, or a productive remote work...