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.
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...
8 Mi to Magic Sands Beach: Tranquil Home w/ Lanai!
Outdoor Dining | Fruit Picking On-Site | Short Drive to Snorkeling & BeachesGet the most out of your next stop on the Big Island when you stay at this Holualoa vacation rental! With a beautiful natural setting just a short drive from the coast, this 2-bedroom, 2-bath...
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...
Westin Ka'anapali - Beautiful Resort On The Beach! Family Friendly! Island View!
The Westin Kā‘anapali Ocean Resort Villas South, located on Maui’s renowned Kā‘anapali Beach, offers an upscale island escape. These spacious villa-style accommodations feature kitchens, private lanais, and luxurious touches. Enjoy multiple pools, a spa, fitness...
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...
Lahaina Shores 621: West Maui Studio with OF Views!
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE! Lahaina Shores 621 – OCEANFRONT!Lahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 621 is a 6th-floor oceanfront...
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 &...
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...
The Cedar House - Private Yard and Entrance!
Welcome to The Cedar House! Just 5 minutes from world-class beaches and surf breaks. Enjoy country living with cool mountain breezes and the soothing sounds of nature, amidst coconut trees, bananas, and tropical plants. Local laws require a minimum 30-night booking, but...
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...
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....
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...
Oceanfront Retreat! Near Waihee Coastal Dunes and Wetlands Preserve, Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Royal Kahana Maui 1105 Ocean View Studio
- - 11th floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile floors in entry, kitchen and...
Aqua Palms Paradise Studio | Walk to Beach
Enjoy sunny palm-tree views from this gorgeous hotel-style studio at the Palms at Waikiki Building. Nestled across the street from Ala Wai Boat Harbor, Hilton Hawaiian Village, Duke Kahanamoku Lagoon, Waikiki Beach, and so much more, our home is walking distance to...
Sugar Beach Resort 619: Many upgrades throughout this 1 Br Penthouse Condo
Ocean Front One Bedroom Condo. This has been refurbished and redecorated with new furniture, carpet, and appliances. This unit sleeps up to two people. New furnishings in the living room give this unit the comforts of home. There is a flat-screen TV in the living room....
Golf Villa 2102 – Contemporary & Ocean Views | Onsite Staff & Daily Housekeeping
Golf Villa 2102 – Contemporary & Ocean Views | Onsite Staff & Daily HousekeepingThis prime ocean-view villa enjoys the premier Golf Villas location at Hualalai Resort. This Golf Villa features unobstructed ocean, golf course, and sunset views and quick access to the...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, Stunning 7th Floor Ocean Views!
This tandem offering brings together one of our best 2br deluxe ocean view corner suites with our very best 1 bedroom suite. The 2br suite offers superb ocean views from its prime corner location, and the adjacent 1br suite offers superb ocean views of its own. Take in...
AirCon, Modern STUDIO in fabulous Kaloli Point, next to Trailhead to Haena Bch
With Airconditioning, after your long day of adventure, nice and cool cozy getaway awaits in Keaau Kaloli Point a Micro climate of sun, at this amazing Detached STUDIO. A detached Studio from Main House. Equipped with essential amenities like WiFi, AC, and a COUCH/Pull...
Maui Ka’anapali Villas #204: Studio Ocean View on N. Kaanapali Beach
Maui Ka’anapali Villas #204: Hotel Room with Ocean Views on N. Kaanapali Beach. Maximum occupancy: 2This hotel room is the perfect homebase for your Maui getaway. Situated on the 2nd floor, there are ocean views from the main room and out on the shared balcony. This...
Mele Olina, Private Home-golf Course & Ocean View
Nestled along the Makai Golf Course in the serene Princeville community, Mele Olina offers a beautiful, secluded retreat with stunning ocean and mountain views. This private family home comfortably accommodates up to 6 guests and is designed for relaxation, connection,...
Blissful Honolulu Oasis: Renovated & Modern w/ AC
*** Disclosure: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Washer dryer in the unit. Free tandem parking allowed Park two...
A11y Room with King Bed, Lanai - Upper Floor
Stay in this accessible 242 sq. ft. room featuring a king bed and a private lanai. Located between the 4th and 11th floors, this room offers accessibility features, air conditioning, free Wi-Fi, and modern amenities for a relaxing and inclusive stay.Key Features: •...
Just What You're Looking For! W/ Kitchen, Outdoor Pool, Free Parking!
Stay in a beautiful beach resort on Northshore Kauai, next to Makai Golf Club!This listing is for a room within a hotel.✦ Your room is 1162 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout...
Royal Sea Cliff Kona Oceanfront 2 Bedroom
Ocean Front 2 Bedroom 2 Bath- Condos located on 2nd, 3rd and 4th floors- Private balcony- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, cookware and tableware- Master bedroom with 1 king bed and private bathroom with...
Spacious 2100 sq. ft. North Shore Condo in a Princeville Resort
On the northern shore of Kauai, there's a beautiful plateau overlooking romantic Hanalei Bay called Princeville. Amidst this splendor, you'll find the private paradise the Ka'Eo Kai resort. A stroll along its winding paths takes you past waterfalls, streams, gardens and...
2br 2ba Modern Kamahana, Pool, Close to Beach
Modern Island Retreat – 2BR/2BA Condo in Kamahana, PrincevilleExperience the beauty of Kauai's North Shore from the comfort of this modern 2-bedroom, 2-bathroom condo located in the peaceful Kamahana complex in Princeville. Surrounded by tropical landscaping and...
Tropical Garden & Pool View at a Beach Front Property-Kihei Kai Unit 8
Condo #08 is a garden view unit located on the lower level. This charming condo is in front of our tranquil pool surrounded by lush palms and fragrant plumeria trees. The kitchen has been newly remodeled and equipped with upgraded appliances. This condo will sleep 4...
Cozy hotel suite in marvelous The Modern Honolulu Hotel
Enjoy a peaceful stay at this brilliant 1-bedroom hotel suites in Honolulu. This cozy retreat offers everything guests need for a nice getaway. With amenities like a fitness room, heating, AC, WiFi, iron, coin laundry, and a hair dryer, you'll have everything you need...
Beachfront Bliss in Kona - Saltwater Pool, Central AC, & Unmatched Views
Welcome to Kona By the Sea #312 — a beautifully remodeled 2-bedroom, 2-bath oceanfront condo with central air-conditioning, located on the top floor of the preferred main building. Enjoy sweeping, unobstructed views of the Kona coastline, saltwater pool, and sandy...
Peaceful, quiet condo with pool, private lanai, gas grill, WIFI, steps to beach
Hale Wailana 3AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your charming retreat in North Kihei, a delightful 2-bedroom, 2-bath condo just 50 yards from the pristine...