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.
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's BEST AC Beachfront – Panoramic Ocean Views! No Cleaning/ Parking Fees
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...
Spectacular Urban Location - A Peaceful Surrender 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,...
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...
Luxurious golf villa with updated appliances
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...
Sans Souci 1106 - A Studio above the Beach
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! Lower rates for April and May!
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 at Turtle Bay Resort - Kuilima Estates West
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...
Kapalua Golf Villas 11P7-8: 2 BR Luxury Condo with Lanai
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...
New Listing | Beautiful 2bed/2bath Oceanfront Unit 105
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...
New Listing! - Wailea Ekahi 39E - Luxurious Ocean View Condo, 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...
VOK29 Hawaiiana 3br 3ba Villa of Kamalii, AC, Pool
Professional photos coming soon. Located in the resort community of Princeville are the Villas of Kamalii, a gated complex located across from the Makai Golf Club. Enjoy lush garden, mountain and waterfall views from Villa #29, an end unit, split-level townhouse with...
Noiulu One – Brand New Hualalai Estate
Located in the exclusive Noi‘ulu Estates neighborhood, this brand new 6 bedroom, 6.5 bathroom custom gated estate home offers an expansive luxury residential experience highlighted by majestic ocean views. Abundant natural light accentuates modern, natural finishes...
crater rim cabin garden view
Crater Rim Cabin is located on the boundary of Hawaii Volcanoes National Park in the edge of the ohia-fern forest of Kilauea. The cabin is nestled among ohia and koa trees in botanical-garden-like surroundings. At an elevation of just over 4000 feet we have a cool...
NEW Listing Spectacular Ocean Front View from Every Room - PRINCEVILLE/HANALEI
A beautiful, unobstructed view of the deep blue Pacific Ocean and coral reef from every room! Our condo is located on an ocean bluff having the luxury of a 180 degree view of blue water from every room. Along with magical waves, you will see outrigger paddlers and sea...
Ideal Family Retreat! - Beach Pass Included - Great Location - Beautiful Sunsets
Fairways at Mauna Lani 1001 -- One of the best locations within the complex -- INCLUDES COMPLIMENTARY ACCESS to the parking at the Beach Club (calm water beach with a great snorkeling and restaurant: 5 minutes driving from us) -- Renovated with attention to details in...
PUN 202 Updated Oceanfront Condo at Punahoa Beach with Stunning Views
Punahoa 202 NEW LISTING! Refreshed OceanFront Condo with Spectacular Ocean Views for a Peaceful and Relaxing Hawaiian Vacation FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal),...
Spacious luxury 2-floor villa with breathtaking ocean, golf, and mountain views.
Welcome to our spacious luxury villa, where you can enjoy breathtaking ocean views, golf courses, and mountains.This exceptional two-floor, 2-bedroom, 3-bathroom unit beckons you into a bright and open layout, encompassing an impressive 1756 square feet of interior...
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and...
Fairway Villas Waikoloa G31-Top Floor Villa w/loft and 2025 Hilton Pool Pass!
Aloha and Welcome to our 2 Bedroom 2 Bath with a loft villa located at the Fairway Villas Waikoloa. We are located in the Waikoloa Beach Resort on the Island of Hawaii. You can explore our Island of Hawaii, beaches, waterfalls, coffee farms, Mauna Kea snow-capped...
Cozy Kona condo walking distance to the beach, shops and restaurants.
Beautiful, clean, cozy, recently updated Kona condo, your home away from home. Beaches, coffee shops, restaurants and boutique stores are all in walking distance. Includes all the essentials to make your stay comfortable and worry-free. In home amenities include:•...
ALOHA-WAIKIKI 2 Blocks 2 Shoreline of BEACH and Upgraded!!!
Located just two short blocks from the shoreline, this unit features a comfy queen sized bed, free wifi, a kitchenette, private bathroom and a private covered balcony from which you are able to enjoy mountain views and tropical breezes.Within our CLEAN PRIVATE unit, my...
WHALE Watching & OCEAN Views! Honua Kai Penthouse- Top Floor- Remodeled June'24
🌴 West Maui is Open – and Honua Kai is Resort-Zoned. 🌴Book with confidence knowing you’re safe from the recent legislation impacting other short-term rentals.🌊 Welcome to Hokulani 749 at the award-winning Honua Kai Resort – a stunning penthouse offering one of the most...
Hidden Jewel 30-day min stay
Your Private Beachfront Retreat in Haleiwa – 30-Day Minimum Stay Escape to your own slice of paradise at Haleiwa Beach on Oahu’s legendary North Shore. This charming one-bedroom, two-bath condo offers the perfect blend of comfort and island charm, with breathtaking...
Poipu Kai Hale - Oceanfront Elegance at Makahuena Point
Welcome Poipu's Hidden Gem! This amazing home offers 3 bedrooms and 3 bathrooms on the ocean with incredible views of Poipu! Imagine your vacation experience in this gorgeous location with unparalleled and unobstructed 200°+ views. This spacious home consists of a...
Modern, Designer Owned 2BD+2BA w/ Loft @ Kuilima Estates West
Experience this spacious, clean & comfortable, newly remodeled unique 2-story townhouse with the conveniences of a home which is fully air-conditioned w/ new quiet Mitsubishi split system a/c. This is especially important for the hot and humid days. There is no unit...
Prime Location for Oceanfront Lovers
Situated in Maalaea, just a short drive from the airport, Island Sands 110 is the perfect base to enjoy all that Maui has to offer. The condo is steps away from the daily bustle of Maalaea Harbor, where you can indulge in a variety of ocean activities, including snorkel...
Royal Mauian #307: Beachfront Bliss with Stunning Views & Resort Amenities
Royal Mauian #307 – Oceanfront Views in the Heart of KiheiRoyal Mauian #307 is a two-bedroom, two-bathroom condo offering breathtaking views of the Pacific Ocean and Maui’s stunning coastline. Perfectly located along the oceanfront in South Kihei, this unit combines...
Downtown Luxury Penthouse, Free Parking, Washer/Dryer
Welcome to your stunning getaway in the heart of downtown Honolulu! This spacious, High-Ceiling two story Penthouse is perfect for families, large groups, or anyone looking to experience the best of the city with comfort and style. With 8 beds distributed across 3...
Pacific Palm Villas at Hali’I Kai 5H! 3 bedroom, Luxury Location With A/C
Welcome to your dream vacation home at Pacific Palm Villas, Hali'i Kai, located in the heart of the exquisite Waikoloa Beach Resort. This opulent 3-bedroom, 2-bathroom villa offers a seamless blend of elegance and comfort, featuring breathtaking views of the lush golf...
Breathtaking Ocean Views from Quiet Beachfront Condo! Free Parking & Wi-Fi!
Colony Surf #1005 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)Stunning ocean and Diamond Head views! This spacious (853 sq. ft.) open floor plan suite is the perfect spot to enjoy...
Renovated beachfront with gorgeous ocean views! Luxurious and family friendly!
(See Video Below) Upgraded, with ocean and garden views, direct beach access, patio and luxury amenities to make this your most memorable vacation! Minutes from Shops at Wailea! Family friendly and serene! Just bring your swimsuit and flip flops because we have you...
Kona Sea Ridge#X1: Beautiful 2 level Spacious 3 bedroom with Ac & Ocean Views
Kona Sea Ridge#X-1 is an excellent beautifully furnished option for your Vacation. This VERY spacious, 2 story 3 bedroom, 3 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people! ~Largest Floor Plan in Kona Sea Ridge. Living Area,...
Maui Resort Rentals: Honua Kai Hokulani 341 - Upgraded 2BR Ocean View Suite w/ Deluxe Corner Floor Plan!
Hokulani 341 delivers a tranquil interior courtyard location with stunning views of the Pacific Ocean. Gather, reconnect, and celebrate in this spacious 2 bedroom/2 bathroom deluxe floor plan which offers an abundance of interior living space and a 340 sq. Ft....
Bright & Cozy Stay Near Waikiki Beach + 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...