The 11 Best Maui Vacation Rentals With Private Pools

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You’re coming to Maui, and you’ve decided to skip the resorts or condos in favor of a house with a private pool. Maybe you just want to retreat somewhere solo without having to share the pool with others (or wake up early to reserve your pool chair). 

I thought that getting a Maui vacation rental with a private pool would be reserved only for the high-end luxury homes (that sleep an army). But I was wrong. There are plenty of vacation rentals on Maui with private pools that fit a range of budgets. 

We’ve rounded up our 11 favorite vacation rentals on Maui with private pools. Pick the location and amenities that are right for you and your family.

Let us help you with all the most important planning details:
1. We have an entire guide to planning the perfect Maui getaway.
2. Maui calls for a rental car, and we call for saving on one.
3. These are the best Maui beaches, plus our tips for parking.
4. If planning gets overwhelming, grab our Maui itinerary and rest easy, knowing the hardest parts are done for you.

1. Hale Makai (Kihei)

This four-bedroom, three-bathroom home sleeps 10 and has a gated pool area — important for keeping young children out when unsupervised. The home requires a minimum stay of 5-7 nights, depending on the time of year, but for most visitors, that shouldn’t be a problem. While this is one of the more affordable homes on the list, it’s a great value for guests. If you’re tired of the pool, the beach is a quick 3-5 minute walk away. 

Average price: $1,000/night
Bedrooms: 4
Minimum stay: 7 nights

Book this home directly on VRBO. 

2. Maui Ocean Palms (Wailea)

Want some real space? This two-bedroom, two-bathroom home in Wailea is set on a half-acre with ocean views. The owners live on the property in the downstairs unit, but reviews mention that you’ll hardly notice that they’re there. You are up a hill from the beach so if you decide to walk, just be ready for a slight workout on your way home. 

And while a private pool is a great draw of this home, take a look at the ocean-view lanai and just imagine having coffee out there every morning. 

Average price: $525 – $675/night
Bedrooms: 2
Minimum stay: 4 nights (14 nights over the holidays).

You can book this home directly on VRBO. 

You can save a lot of money by choosing a vacation rental and eating in. But you can also get the best of both worlds with well-priced, delicious food from Maui food trucks!

3. Auntie Kali’s Cottage (Kihei)

This two-bedroom ocean-view cottage has been recently updated and offers a stunning spot for your Maui retreat. It’s on the smaller size (700 square feet), but with the beautiful grounds, a private pool, a private hot tub, a fully-equipped tiki bar, a firepit, a built-in BBQ, and an outdoor shower, you likely won’t be spending much time inside anyway. The cottage is located just above Wailea beach, on the Kihei/Wailea border. 

Average price: $900/night
Bedrooms: 2
Minimum stay: 7 nights

You can book the cottage directly on VRBO. 

4. South Beach at Coconut Bay (Kihei)

Traveling with a large group? This five-bedroom home is a great spot for up to 10 guests. Set on the beach in Kihei, you’ll have a hard time finding a better lanai. You can sit in the private pool or private hot tub and stare out at the ocean. Or jump into the water for a swim before retreating back to your home for relaxation. Modern, clean, updated, and spacious (3500 square feet!), this place is truly luxurious.

Average price: $3,750/night
Bedrooms: 5
Minimum stay: 5-7 nights

You can book the home directly from VRBO. 

5. Summit Residence at Kaanapali Vista (Kaanapali)

If you’re looking for a lot to keep you busy at your vacation home, this home is for you. Not only does it feature a private pool, you have a hot tub, entertainment room, fitness center, and mini-spa within the 4,500 square foot home. Just up the hill, you are a short walk from the beaches and resorts of Kaanapali and Whaler’s Village but away from it all that it’s quiet. Plus, one of the lanais overlooks the golf course for a scenic view. 

Average price: $2,000/night
Bedrooms: 5
Minimum stay: 4-7 nights

You can book the home directly on VRBO. 

6. Updated Napili Bay (Napili)

This four-bedroom home was recently renovated in 2018 and is just a short walk to Napili Bay, one of the best beaches on Maui. With a sleeper sofa and bunk beds, this home can sleep 12 people. The pool is private, new, and beautiful, but beware that there is an extra cost to heat it. 

Average price: $1,250/night
Bedrooms: 4
Minimum stay: 6 nights

You can book the home directly on VRBO. 

Related articles:

• The 15 Best Things to do in Kapalua and Napili
• 65 Things to Do with Kids in Maui (by age): Your Family Will Love Them
• Where to Stay on Maui with Kids: 10 Best Resorts and Vacation Rentals

7. 1946 Kihei Home (Kihei)

This might be one of the most stunning backyards. This four-bedroom home was built in 1946 on a large lot along a beach reserve. The home sleeps 14, assuming that it’s a mix of children and adults staying at the home. The lanai overlooks the private pool and is covered with ceiling fans — helpful for those hot days. The backyard is large with plenty of room for kids to run around and explore. 

Average price: $2,300/night
Bedrooms: 4
Minimum stay: 5-10 nights

You can book the home directly on VRBO. 

8. Cloud 9 Beach House (Kihei)

Welcome to this charming, 3-bedroom two-bathroom home on the border of Kihei and Wailea. Tucked back in a residential neighborhood, you’re a quick 10-minute walk to the beaches. Newly remodeled, the home can sleep seven people. Enjoy the yard in the pool or in the shaded hammock — perfect for an afternoon of relaxation. 

Average price: $680/night
Bedrooms: 3
Minimum stay: 5-14 nights

You can book the home directly on VRBO. 

9. Kula Private Home (Kula)

If you really want to get away from the resort areas on Maui, this upcountry home is exactly what you need. Located on seven acres, this three-bedroom home has panoramic ocean views (the view from the pool is breathtaking). 

Note: as the bird flies you are not too far from the beaches. But it’s actually a deceptively long drive to enjoy the ocean. This may not be a drawback, depending on the type of vacation you’re looking for. 

Average price: $1,175/night
Bedrooms: 4
Minimum stay: 3 nights

You can book the home directly on VRBO. 

10. Kalapana (Launiupoko)

Another option for those looking to get away from it all, while actually being pretty centrally located to everything. This home is located in the hills above Lahaina with a sweeping view of the ocean. It features a new pool and a jacuzzi, as well as three bedrooms, a gym, and a wrap-around lanai. You’re just a 10-minute drive to downtown Lahaina and a 15-minute drive to the beaches in Kaanapali. 

Pick the fresh fruit on the property for a delicious breakfast before heading out for the day. 

Average price: $1,200/night
Bedrooms: 3
Minimum stay: 5-14 nights

You can book the home directly on VRBO. 

11. Pililani (Haiku)

Want to experience the north shore? This home is located on four acres and comes with so many features: a private pool, hot tub, tennis court, sauna, an outdoor shower, and fruit trees. It’s a true retreat. Like with other homes that are away from it all, it’s a bit of a drive to get to the beach. But that drive will be worth it for people who are looking for this unique rental home experience on Maui. 

Average price: $1,500/night
Bedrooms: 5
Minimum stay: 4-14 nights

You can book the home directly on VRBO. 

Time to book your place to stay on Maui. These vacation rentals with a private pool are the best we found, after extensive research. Enjoy your trip to Maui knowing you found the rental you wanted at the right price.

Now that you have your place to stay with a private pool, time to figure out what to do on Maui. Grab our Maui Itinerary to finish off your Hawaii vacation planning.