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.
*Hono Kai A14* New Listing! Maui condo steps to the sand!
Beautiful ground floor and newly remodeled! Hono Kai A14 is a garden-view unit, immersed in rich tropical foliage with a spacious private lanai only steps from the complex beach access! Decorated with a modern beachy decor, this unit features a master suite with a comfy...
1 Bedroom Partial Ocean View Condo - Kaanapali Shores 830
Settle into your Hawaiian vacation in this Oceanfront and ground-floor condo with beach and pool access in Kaanapali. Wake up to the ocean breeze and just steps away from one of the most popular beaches in Maui. Recent upgrades include: The kitchen has all-new stainless...
Feb. 15-21 Marriott Waiohai resort 2 Bedroom 2 Bath, full property access
Feb. 15-21 (6 days) at Incredible Wahohai Marriott vacation resort with full 2-bedroom villa in Poipu. Full access to property amenities including pools, beach access, hot tubs, kids play area, kids activities, firepits, and fitness center. Resort villa boasts a full...
"Windjammer" Studio w/FREE parking & Full Kitchen
Our Premium WINDJAMMER STUDIO is spacious, recently renovated, fully furnished and centrally located just steps away from famous Waikiki Beach where you can enjoy the sand and surf. We include FREE PARKING, full kitchen, free Wi-Fi and a private lanai. We provide 100%...
Airy Coastal Dream Vistas
Summary:Completely remodeled 1 br, 1 bath modern condo with upscale Hawaiian style. Located directly across from the beach in warm & sunny Kihei. Nestled in the lovely and desirable Kihei BayResort, you will be embraced in the tranquil grounds and ocean views. We...
RELAX w/ Direct Beach Access High Flr. Sans Souci 2BD/2BA🌴Stunning Ocean Views
Nestled along the southeastern coast of Oahu, Hawaii, welcome to Sans Souci condominium 901/902, on the only beach in the heart of Diamond Head along the Gold Coast adjacent to Waikiki. The first thing you will notice is the incredible ocean view from this luxurious...
One bedroom, sleeps 4, large lanai, great location, and free parking.
Our villa is on the 3rd (top) floor, with a large lanai (patio) overlooking the pool area. Our living room has a vaulted ceiling and an overhead fan, with sliding doors going out to the lanai. Our unit has one good sized bedroom, a full kitchen, and a bathroom. There is...
Worldmark Kihei
Once you arrive in Maui, WorldMark Kihei will welcome you with beautiful sights, wonderful amenities and exciting activities to do during your trip. The resort offers spacious studio, one-, two- and three-bedroom resort suites which come equipped with a kitchenette or a...
A11y Room with 2 Double Beds, Lanai and City Views
Designed with accessibility in mind, this 242 sq. ft. room features two double beds and a private lanai with city views. With accessible features, air conditioning, free Wi-Fi, and modern amenities, this room ensures a comfortable and convenient stay for all guests.Key...
Alii Villas#318 Beautiful Top Floor Condo with Garden & Ocean Views
Top-Floor Ocean Escape – Remodeled Beauty at Alii Villas #318Welcome to your slice of paradise on the top floor of the highly sought-after Alii Villas in stunning Kailua-Kona, Hawaii! Unit 318 is a fully remodeled, beautifully furnished condo that blends island charm...
Secluded Paradise, Stunning Views, Hidden Beaches, Ocean Sunset
Enjoy breathtaking sunset ocean views from the front, and take in the beauty of the majestic mountains and waterfalls from the back lanai. Our stand-alone condo offers privacy and convenience, just steps away from the renowned 1Hotel and paths to beautiful beaches. With...
STUNNING 1st Floor 🌴 Beachfront 2BD Sans Souci w/Parking 🐬
30 Day Rental: Checkout our 2024 Special Offers in July, September & October!Discover the tranquil retreat of this fully furnished two-bedroom vacation rental, perfectly situated on Kaimana Beach in Sans Souci. With just a few steps separating you from the gentle waves...
Honolulu Paradise Condo
Centrally located condo, steps to all your destinations while you visit Hawaii. 2 bedroom's and 2 bathrooms plenty of space to enjoy, relax, and adsorb paradise. Open full kitchen overlooking the balcony with mountain and water views best of both worlds. Completely...
Beach Inspired Family Suite w/ Kitchen, Washer/Dryer, Lanai–Waikīkī Shore 510
Welcome to your home-away in this fifth-floor, one-bedroom one-bathroom, ocean view unit. Upon entry, you will be greeted with a white back-drop that has been enhanced with many shades of blue throughout the space. Welcome to the 'beach house!'Guests can embrace the...
Large 2 Bed 2 Bath in Gorgeous Maui Kamaole Complex South Maui
Perfectly perched on the second floor, our vacation rental offers a serene retreat elevated above the ordinary. Upon arrival, conveniently park your vehicle in the space directly in front of the property. A welcoming staircase leads you to the entrance of the condo,...
Lanikai Oceanfront Home with Pool and Japanese-Style Hot Tub
Six bedroom ocean front home with pool and Japanese-style onsen (hot tub) is ideally suited for multi-family or multi-generational accommodation. Recent renovations and 2021 upgrades include split-air conditioning throughout the home, updated landscaping, new...
Urban Chic Meets Island Serenity in Waikiki
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch building.Enjoy breathtaking Mountain & Canal views. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right...
OCEAN FRONT 9th Floor Corner unit nWatch the Whales jumping from the Balcony
In the heart of Maui's famous Kaanapali Beach, steps away from Whaler's Village, with beautiful shopping and restaurants. Beautifully remolded and decorated one bedroom with 2 FULL baths, sleeper sofa and roll-away bed. Wrap around balconies and magnificent views....
Beach Front Condo-Everything you can dream of for a Hawaiian getaway is here!
Enjoy a pleasant stay at this 1-bedroom condo in the quiet country of Hauula. Perfect for relaxing after a day of exploring Oahu. This quaint property offers a cozy living room with a sofa bed. In your temporary home you can take advantage of all the amenities your used...
DEC 19-26th week in Westin Nanea on Kaanapali Beach-Full resort access
Come enjoy the holidays in paradise at Westin Nanea Villas on Kaanapali beach.RESERVATIONS AVAILABLE IN SEVEN NIGHT INCREMENTS ONLY WITH CHECK-INS ON FRIDAY, SATURDAY or SUNDAY. We have one week available, December 19-26th. You must book the entire week. PLEASE CHECK...
Westin Kaanapali North Oceanview - Christmas & New Years Weeks - 1 bedroom
We own a 2-bedroom unit that can be rented as a studio, 1-bedroom, or 2-bedroom. This is the 1-bedroom listing.While most guests do not know which unit they will be assigned to until arrival, this is a fixed unit, 7570. This unit is located on the 5th of 6 floors and...
Waikiki Grand 1005 - The Best location in Waikiki!
Elevate your stay in our charming flat, perched on the 10th floor of a unique boutique condotel. 🏛1005 at the Waikiki Grand Hotel® is perfect for couples or small families, our spacious retreat offers breathtaking views of the ocean and lush surroundings that will...
Palms at Wailea Villa 1805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- 473 square foot lanai- Master Bedroom with 1 king size bed and guest bedroom with Queen- Queen sofa bed in sunken living room- 1194...
Kapalua Golf Villas Fairway View 2 Bedroom
Golf Villas Fairway View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed or 1 queen bed and bathroom- Guest bedroom...
Aston at the Whaler on Kaanapali Beach 964
Stunning ocean views are the highlight of this beautifully remodeled studio located on the 9th floor of Tower 2 at the Whaler on Kaanapali Beach. This studio condo has a King bed and central air conditioning. The living area features a large flat-screen TV and a comfy...
Hanalei Oasis Steps from the Beach
Our home in Hanalei Bay (with a beautiful, recent interior makeover) is nestled in one of the most desirable locations on the North Shore, on a quiet cul-de-sac, 1 house away from the beach and some of the best surf in the world. Take an easy walk or bike into town or...
New Listing! Traditional Hawaiian-Inspired 1 bd
Maui Kaanapali Villas A412 is a charming 1-bedroom, 1-bathroom condo on the 4th floor, offering central A/C, high-speed Wi-Fi, and serene garden views. With convenient elevator access, getting to and from your island retreat is simple and seamless. This unit comfortably...
Wailea Beach Villas PH107
Wailea Beach Villas Penthouse 107 is a luxurious haven that embodies the essence of island living, offering breathtaking pool views and peekaboo ocean views from its prime Wailea location. This expansive 2-bedroom villa includes a versatile den that can be used as a...
Diamond Head View Condo, Steps to 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...
Ilikai Hotel, Breezy City Views! Great for your Hawaiian Getaway!
This condo has been fully renovated and tastefully decorated for your comfort and enjoyment. This spacious 1-bedroom condo has 500 sq ft of living space & a lanai of 120 sq ft. Relax on the cooler side of the building and enjoy the tropical breezes from the mountain....
Hip Hawaii Vibe w/AC, WiFi, Lanai, Modern Kitchenette – Waikīkī Grand #904
Castle at Waikīkī Grand #904 - Hawaiian décor defines this air-conditioned 204sf escape where the furnished lanai creates a perfect perch for morning coffee and evening mai tais. The upgraded kitchenette features granite countertops, mini-frig, microwave, and...
Royal Kahana Maui 205 Ocean View Studio
- 2nd floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in tiled shower with grab bar- 1 king bed and twin sofabed- Ceiling fan- Cable TV-...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms + Den w/ Stunning Ocean Views and Massive Wrap-Around Lanai!
This gorgeous 3 Bedroom/1 Den offering at The Honua Kai Resort on Kaanapali North Beach combines two best-in-class suites. The two-bedroom corner suite boasts deluxe ocean views from both the interior of the residence and the luxurious wrap-around balcony. The...
Kaanapali Alii | 285
Welcome to your dream vacation rental at the prestigious Kaanapali Alii, located on the stunning shores of Maui, Hawaii. This luxurious one-bedroom, two-bathroom residence offers the perfect blend of comfort, elegance, and breathtaking ocean views, making it an ideal...
38th Fl Azure Ala Moana Condo w/ Parking
Honolulu is waiting for you at this 1-bedroom condo. This gorgeous space features a king bed, AC, and a fitness room. Imagine waking up to the serene views and enjoying the amazing amenities provided. Fall in love with Honolulu and enjoy the magic it has to...
Lahaina Shores 621: West Maui Studio with OF Views!
Lahaina Shores 621 – Oceanfront Studio in West MauiLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 621 is a 6th-floor studio offering privacy, comfort and can accommodate 2 guests. Step onto...
Wailea Grand Champions | 140
Wailea Grand Champions 140 is a remarkable vacation rental nestled in the upscale Wailea community of Maui. This charming property combines elegance with comfort, offering a luxurious retreat that is perfect for both relaxation and adventure.Upon entering Wailea Grand...
Maui Bay Villas by Hilton Grand Vacations Club - 1 Bedroom Plus
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Kaanapali Plantation 7 - Remodeled - Summer Discounts!
** Last-Minute Cancellations...take advantage of special rates into the Summer! **Kaanapali Plantation #7 - Single level, spacious, two bedroom/two bath with central air conditioning. The jewel of this condominium is the lanai which can be accessed from the main living...
Your Hawaii Vacation Awaits in Ko Olina (KoK-1029B)
One Rate, You Choose the Length of Stay!All rates quoted will be based on a 30 day period. Our monthly rentals will be made available to you for your use and occupancy for a period of thirty (30) days. You are not required to stay for a full 30 day period. Just stay for...
Maui Resort Rentals: Westin Ka'anapali Ocean Resort South 1BR Islandview Villa
Welcome home to The Westin Ka'anapali Ocean Resort Villas and enjoy the luxury you deserve on vacation! The Westin Villas property is legendary with amazing pools coupled with an incredible location on prestigious North Ka'anapali Beach. This spacious 800 sq ft 1...
Luxury Ocean View Beachfront full-kitchen condo in Lahaina Maui
[New listing 6/11/22]A calm refreshing breeze came from the sea and ran through the living room. Half of it bolted out the front door and the other half through the bedroom, into the valleys of Maui.BEACH This is next to Kahana beach, part of Lahaina, a 10 minute drive...
New Listing! Chic 1bd with an updated kitchen
Welcome to Kapalua Golf Villa 23P 3&4—a beautifully maintained 2-bedroom, 2-bathroom condo that combines comfort with island elegance that can comfortably accommodate up to 6 guests. This villa features central A/C, and the convenience of an in-unit washer and dryer....
Spacious 3 Bedroom / 2 Bath / Sleeps 8
Beautiful home located on the east side of Oahu in Hawaii Kai. Located near beaches such as the famous Hanauma Bay, eateries, shopping centers, hiking trails, scenic lookouts and water sports. The home offers 3 bedrooms (3 queen beds), 1 sofa bed and 2 bathrooms....
Loft In Kailua - Spacious with Parking, Internet and minutes to Kailua Beach!
MINUTES TO KAILUA BEACH AND TOWN!!This well appointed one bedroom split level loft apartment is beautifully furnished with high ceilings and open floor plan. The upstairs has a shuttered master suite with queen bed, a huge en-suite full bath that has a soaking tub and...
Poipu Kai Kahala 232 - One-bedroom Ocean View condo on the island of Kaua'i.
Poipu Kai Kahala 232 - One-bedroom Ocean View condo on the island of Kaua'i. Primary bedroom: King BedPrimary bathroom: full bath ensuite with single showerLoft: Queen bedSecond bathroom: full bath with single showerMax Occupancy: 4 peopleAC: NoneLaundry: in the...
Marriott's Kauai Beach Club 1BR Oceanfront Suite
Nestled along the pristine shore of Kalapaki Beach, minutes from downtown Kauai in the gorgeous southeast city of Lihue, Marriott's Kauai Beach Club is a picturesque oceanfront community offering effortless access to world-class shopping, dining, golfing, and...
Marriott's Maui Ocean Club - Luxurious 1-Bedroom - Kids Pirate Pool - Island View
Come explore Maui at this premium level Marriott property by the ocean. Surrounded by clear, blue waters of the Pacific, this dream getaway is the perfect place to enjoy your next tropical destination.This property has everything you need for a tropical vacation. There...
Pool Access: Ocean-View Molokai Shores Condo!
Scenic Outdoor Dining | Direct Beach Access | Community PerksImmerse yourself in the enchanting Hawaiian ambiance at this 1-bedroom, 1-bath vacation rental. Situated on the shores of Kaunakakai, this oceanfront condo boasts tranquil ocean views from the cozy interior...