Explore Kaupo Vacation Rentals

About Kaupo Vacation Rentals

Explore more than 87 vacation rentals available in Kaupo. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Kaupo.

Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Kaupo, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Kaupo. The average room size in accommodations near Kaupo is 685.59 ft². Prices average US $503 per night.

HawaiiVillas streamlines and secures your search for vacation rentals in Kaupo, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.

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Top Rental Accommodation Types in Kaupo

Type Count
Holiday Apartments 31
Vacation Homes 25
Cottages 12

Use these Quick Filters to Find a Vacation Rental in Kaupo

Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal accommodation for your next vacation in Kaupo.

Weather in Kaupo, HI

View the weather forecast for Kaupo before booking your Kaupo Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Your Guide to Vacation Rentals in Kaupo

Are you ready for a vacation full of adventure, stunning natural scenery, and relaxation? Look no further than Kaupo, Maui, a lesser-known destination that's quickly gaining popularity among travelers. And what better way to experience the beauty of Kaupo than by staying in a vacation rental that provides all the comforts of home while immersing you in the local culture? In this comprehensive guide, we'll cover everything you need to know about vacation rentals in Kaupo, from choosing the right type of rental to booking your dream getaway.

Discovering Kaupo, Maui

A Brief Overview of Kaupo

Kaupo is a picturesque coastal community located on the southern coast of Maui, the second-largest of the Hawaiian Islands. It's known for its rugged terrain, lava rock formations, and stunning sea cliffs that drop off into the Pacific Ocean. Despite its stunning natural scenery, Kaupo remains a lesser-known destination compared to popular destinations like Lahaina and Kihei, making it an ideal location for travelers looking to get off the beaten path.

As you explore Kaupo, you'll discover a rich history and culture that dates back centuries. The area was once home to ancient Hawaiian settlements, and many of the local residents today are descendants of these early inhabitants. You'll find evidence of this history throughout Kaupo, from the petroglyphs etched into the lava rocks to the traditional Hawaiian fishing practices still used by local fishermen.

Top Attractions and Activities in Kaupo

From hiking to beachcombing, there's no shortage of activities to enjoy in Kaupo. Perhaps one of the most popular attractions is Haleakala National Park, which boasts breathtaking views of the sunrise and sunset and is home to a diverse range of rare plants, as well as numerous hiking trails.

If you're interested in learning more about the history and culture of Kaupo, be sure to visit the Kaupo Store. This historic building has been a gathering place for locals and visitors alike for over 100 years and is filled with fascinating artifacts and photographs that tell the story of Kaupo's past.

For those seeking adventure, Kaupo offers some of the best surfing and snorkeling spots on Maui. The area's secluded beaches provide the perfect backdrop for a day of water sports, and you may even spot some of the local marine life, such as sea turtles and dolphins, while you're out on the water.

But if you're looking for something a little more low-key, simply taking a leisurely stroll along the coastline can be a wonderful way to experience Kaupo's natural beauty. The sea cliffs and lava rock formations make for a dramatic backdrop, and you'll likely see a variety of seabirds and other wildlife along the way.

Whatever your interests, there's something for everyone in Kaupo. With its stunning natural scenery, rich history and culture, and wide range of activities and attractions, it's no wonder that this hidden gem is quickly becoming one of Maui's most popular destinations.

Types of Vacation Rentals in Kaupo

Kaupo, a small town located on the southeastern coast of Maui, is a popular destination for vacationers looking for a peaceful and secluded getaway. The town is known for its beautiful beaches, stunning sunsets, and lush tropical landscapes. When planning your trip to Kaupo, choosing the right vacation rental is key to making your stay comfortable and memorable. Here are some of the different types of vacation rentals available in Kaupo:

Beachfront Properties

For those dreaming of direct ocean access and stunning sunsets, beachfront properties are the perfect option. These rentals range from spacious multi-bedroom houses to cozy cottages, but all offer unbeatable access to the sand, surf, and sea. Imagine waking up to the sound of waves crashing and enjoying your morning coffee with a view of the Pacific. For many, this is the ultimate Kaupo vacation experience.

Some popular beachfront properties in Kaupo include the luxurious Wailea Beach Villas and the cozy Makena Surf.

Private Villas and Cottages

For travelers seeking privacy, exclusivity, and upscale amenities, private villas and cottages are the way to go. These rentals typically feature high-end furnishings, private pools, and modern appliances, making them ideal for families, couples, and small groups. Some of these properties even come with personal chefs, housekeeping services, and other perks to make your stay even more memorable.

One of the most popular private villas in Kaupo is the stunning Haleakala Villa, which features breathtaking views of the ocean and the surrounding mountains.

Condos and Apartments

Looking for a more budget-friendly option while still enjoying all the comforts of a home away from home? Consider booking a condo or apartment rental. These spaces range from cozy studios to multi-room apartments, with options that can accommodate families, couples, and solo travelers. Many of these rentals feature communal amenities like pools, barbecues, and fitness centers, and offer easy access to shops, restaurants, and other local attractions.

The Kihei Bay Vista is a popular condo complex in Kaupo, offering affordable and comfortable accommodations just steps away from the beach.

Unique and Off-the-Beaten-Path Options

If you're looking for something truly unique, consider one of Kaupo's many off-the-beaten-path rentals. These options abound with character and charm, from rustic treehouses to converted shipping containers. While they may not offer all the upscale amenities of other rentals, they provide a unique glimpse into the local culture and history of the area.

The Bamboo Temple is a popular off-the-beaten-path rental in Kaupo, offering guests a chance to stay in a beautifully crafted bamboo structure surrounded by lush tropical gardens.

No matter what type of vacation rental you choose in Kaupo, you're sure to have a memorable and relaxing stay in this beautiful and serene part of Maui.

How to Choose the Perfect Vacation Rental

Choosing the perfect vacation rental can be a daunting task, but it doesn't have to be. With a little bit of planning and research, you can find a rental that meets all of your needs and preferences. Here are some tips to help you get started:

Assessing Your Needs and Preferences

Before you start browsing vacation rentals, it's important to assess your needs and preferences. Consider factors such as the size of your party, the length of your stay, and the amenities you're looking for in a rental. Do you need a pet-friendly rental or one that's wheelchair accessible? Are you looking for a rental that's close to local attractions or one that's tucked away in a private location? Understanding your must-haves and nice-to-haves will help guide you through the search process and ensure you find the perfect rental for your needs.

For example, if you're traveling with a large group, you may want to look for a rental with multiple bedrooms and bathrooms to accommodate everyone comfortably. If you're planning a longer stay, you may want a rental with a washer and dryer to make laundry easier. And if you're looking to relax and unwind, you may want a rental with a private pool or hot tub.

Comparing Rental Prices and Amenities

Once you've narrowed down your search to a few key rentals, it's time to start comparing prices and amenities. Be sure to read the fine print, including any fees and taxes, to avoid surprises later on. Look for rentals that offer the amenities you need, such as air conditioning, high-speed internet, or a fully-equipped kitchen. If you're traveling with kids, consider rentals that come with kid-friendly amenities like cribs and high chairs.

It's also important to consider the location of the rental when comparing prices. A rental that's farther away from local attractions may be less expensive, but you'll need to factor in transportation costs to get to those attractions. On the other hand, a rental that's closer to attractions may be more expensive, but you'll save money on transportation.

Reading Reviews and Testimonials

One of the best ways to gauge the quality of a rental is to read reviews and testimonials from previous renters. Look for trends in what renters praise and criticize about the rental and the property owner. If you're concerned about cleanliness or maintenance issues, look for reviews that address these topics directly.

Most rental platforms offer reviews and ratings from previous renters, but you can also check social media and travel forums for more candid feedback on specific rentals and property owners. Keep in mind that some reviews may be biased or fake, so it's important to read a variety of reviews to get a well-rounded picture of the rental.

Proximity to Attractions and Activities

Finally, consider the location of your rental in relation to the attractions and activities you're most interested in. Do you want to be within walking distance of the beach or a short drive away? Are you interested in hiking trails or local restaurants?

By choosing a rental that's close to your ideal activities, you can make the most of your vacation time and enjoy all that Kaupo has to offer. And if you're not sure what activities are available in the area, don't be afraid to ask the property owner or do some research online.

With these tips in mind, you'll be well on your way to finding the perfect vacation rental for your next trip. Happy travels!

Booking Your Kaupo Vacation Rental

Are you looking for the perfect vacation rental in Kaupo? Look no further! Kaupo offers a variety of rental options, from cozy cottages to luxurious villas, that will suit any budget and style. Here are some tips for booking your dream vacation rental.

Using Online Booking Platforms

One of the easiest ways to book a vacation rental in Kaupo is through online booking platforms like Airbnb, Vrbo, and Expedia. These platforms allow you to browse and compare rentals, view photos and reviews, and book your rental with just a few clicks. You can filter your search by price, location, amenities, and more to find the perfect rental for your needs. Be sure to read the fine print, including any fees or cancellation policies, before booking.

When booking through online platforms, you can also communicate directly with the property owner or manager to ask any questions you may have before booking. This can give you peace of mind and help you make an informed decision.

Contacting Property Owners Directly

If you prefer a more personal touch and want to avoid service fees associated with online booking platforms, consider contacting property owners directly. Many rental owners list their properties on multiple platforms, so you can often find contact information to communicate directly with them. Simply send an email or make a phone call to inquire about availability and pricing.

When contacting property owners directly, you can also ask any questions you may have about the rental that aren't addressed in the listing. For example, you may want to know if there are any local restaurants or attractions nearby, or if the rental has any special features like a pool or hot tub.

Working with Local Rental Agencies

If you're still unsure about which rental to choose or prefer a more hands-off approach, consider working with a local rental agency. These agencies specialize in vacation rentals and have in-depth knowledge of the area and rental market. They can work with you to identify the rental that fits your budget and style and handle all the details of the booking process.

Local rental agencies can also offer valuable insights into the local area, including recommendations for restaurants, activities, and attractions. Some agencies even offer concierge services that can help you plan your vacation activities and make restaurant reservations, so you can sit back and relax while they take care of the details.

No matter which booking method you choose, be sure to book early to ensure availability and get the best rates. With these tips, you'll be well on your way to booking the perfect vacation rental in Kaupo!

Conclusion

Whether you're a first-time visitor to Maui or a seasoned traveler, a vacation rental in Kaupo is the perfect way to experience everything this stunning destination has to offer. With our guide to vacation rentals in Kaupo, you're now equipped with everything you need to know to book your dream getaway. So, what are you waiting for? Start planning your Kaupo vacation today!

Frequently Asked Questions About Kaupo?

What are the top vacation rentals in Kaupo?

Currently, HawaiiVillas lists over 87 properties in the Kaupo area for 2025, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Kaupo.

Which vacation homes in Kaupo are best for families?

If you're searching for a family-friendly vacation residence in Kaupo, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Kaupo:

How many Hawaii.Villas vacation rentals are available in Kaupo?

At present, HawaiiVillas showcases more than 87 properties available in the Kaupo area for 2025, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Kaupo.


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