Vacation rentals with a pool in Maui County

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Top-rated rentals with a pool in Maui County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Lahaina

4.91 out of 5 average rating, 262 reviews

The Sunset Stowaway—A Peaceful Napili Ridge Studio

Peaceful studio located at The Napili Ridge, in the highly sought-after west side of Maui. Equipped with a Westin Heavenly Brand KING bed, full kitchen and loads of ALOHA. Complete with all the essentials of island living and cooking (All utensils, microwave, full fridge, DW, french press, coffee grinder, toaster, blender, fresh linens, beach towels, cooler, beach chairs, hair dryer, Smart TV, free WiFi and tropical fans and AC to keep you nice and cool. Brand new stainless steel appliances. This is a QUIET off the beaten path residence- not a resort- with both long term residents and vacationers utilizing the property-please respect the quiet. This space is optimal for those who want to get out and enjoy the Maui outdoors with all its magic it has to offer at a GREAT price. Please note: We are located on the bottom floor but there are a few stairs to get to us from the parking space. The entire studio space is yours! Full kitchen and bath (shower only, no tub). A nice outdoor lanai to enjoy your morning cup of locally grown coffee. A FREE and RESERVED parking space. The property itself is equipped with a pool, BBQ, and coin-op laundry for our guests to use. ( property rules and hours of operation do apply). Available by text, email, and phone. We live very close if you should need but have lock box entry so that you may check in on your own accord. Check in is 3pm (or anytime after, until 10pm), Check out is 10am. The location of Napili is the highly desired west side of Maui, right in the heart of the action. It's only a block from Napili Bay, and a walk or a short drive to many great restaurants and beaches, plus a grocery store. Make sure and catch the bi-weekly farmers' market. Best to rent a car to see all Maui has to offer. We do have a free reserved parking spot just for you. There is a local bus that can be easily accessed, with a stop just at the bottom of our road. Uber, Lyft, and cabs available; times and rates vary. Bike rentals available. We are committed to being as sustainable and eco-friendly as we can possibly be and we appreciate our guests to be as well. Recycle, reduce, and conserve while you visit Maui. We have Hi-5 recycling available on property. Electricity costs at least double up to triple that on the mainland. Please turn off lights TV AC and fans when not using. Do not walk on the reef. Ever. Just because you have reed shoes doesn’t mean you should use them. Do not litter-Take your trash with you and dispose of it properly while visiting our parks and beaches. Support local business. Rent a "Bio-Beetle" or hybrid vehicle to get around. Volunteer if you have time. There are always beach clean ups happening or preform your own mini version. Leave the sand at the beach! Sounds simple right?-Please shake your towels, beach chairs and rinse your feet out at the beach. And finally a common sense disclaimer....Since we are in a residential community there may be construction happening. While we live in a very quiet community that has quiet hours we cannot guarantee work will not be happening around us during week day work hours. Mahalo! TAT-202-886-4512-01

Mar. 21 – 28

$300 CAD per night

Guest favourite

Home in Kihei

4.96 out of 5 average rating, 390 reviews

Stunning ocean view, heated pool at home by Wailea

Last minute bookings 5 days before arrival, and week long stays are 10% off. Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Oct. 24 – 31

$927 CAD per night

Guest favourite

Cabin in Maui

4.98 out of 5 average rating, 172 reviews

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

Jul. 14 – 21

$1,183 CAD per night

Guest favourite

Condo in Kihei

5.0 out of 5 average rating, 137 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

SPECTACULAR OCEAN AND SUNSET VIEWS, including outer islands from the living room and lanai. You'll enjoy drinks in the evening watching the incredible sunsets. The condo has been totally redecorated and upgraded. The kitchen and bathroom are newly remodeled with maple cabinets and elegant granite counter tops. There is a very comfortable king size bed, a well-stocked kitchen, central AC, bamboo floors throughout, and a washer / dryer. The Condo is owned and maintained by Maui residents.

Feb. 20 – 27

$820 CAD per night

Guest favourite

Townhouse in Kihei

4.79 out of 5 average rating, 286 reviews

Kihei Bay Surf #149 / HI Taxes included in price

Kihei Bay Surf #149 is a first floor studio with patio and grass area. The unit is located across the street from the State Beach and the National Humpback Whale Sanctuary. Quiet split system A/C (no noisy window unit) 55 inch Samsung TV, DVD, Wireless and wired internet. Full Kitchen with all amenities. In addition, there is a large pool, hot tub, tennis court and gas grills in the pool area for your use. Free parking and no additional resort fees or taxes are added to your daily rate.

Oct. 15 – 22

$288 CAD per night

Guest favourite

Condo in Lahaina

4.99 out of 5 average rating, 135 reviews

Sunsets and turtles and whales... oh my!

Spectacular ocean views Whales and turtles galore(whale season Nov-March) Great snorkeling Gorgeous landscaping Pool, grills, shuffleboard, laundry, and huge sundeck Pristine beaches, grocery stores, world class shopping nearby Sleek and modern Maui hale New lanai flooring and comfy outdoor couch Chef's kitchen Stainless steel appliances Tv & wifi Cali King bed with luxury linens Beach toys Cooling trade winds Boutique building Elevators and luggage carts Free parking

Jun. 4 – 11

$400 CAD per night

Guest favourite

Condo in Maunaloa

4.97 out of 5 average rating, 235 reviews

Sweet Upstairs Corner Ocean View Studio on Molokai

Top floor corner unit at Kepuhi Beach Resort, on the special island of Molokai....in between Maui and Oahu! Vaulted open ceilings, spacious and airy. Completely remodeled and freshly outfitted. Close to beach and ocean-side pool, views of Kaiaka Rock, ocean surf, vivid sunsets. Fully equipped kitchen, luxurious King sized bed. Fast wireless , 40” SmartTV. Perfect setting to unplug, hike or bike the red dirt trails, explore beaches, and experience Molokai fully.

Aug. 10 – 17

$174 CAD per night

Guest favourite

Condo in Lahaina

4.92 out of 5 average rating, 381 reviews

Napili Nani cottage for 2 w/AC ~ *Renovated*

"Napili Nani" is a darling studio cottage in the Napili Ridge Condominiums, located just a short walk to the beautiful Napili Bay, The Gazebo Restaurant and The Sea House Restaurant. Our cottage for two is a relaxing and lovely alternative to the high traffic, commercial areas on the island and offers a more "authentic, local Hawaiian" experience. If mismatched furniture and a beachy, cottage style vibe is your thing, then Napili Nani is the place for you!

Nov. 6 – 13

$307 CAD per night

Guest favourite

Condo in Kihei

4.92 out of 5 average rating, 190 reviews

Beautiful & clean condo w/ excellent location

This condo is marked with special touches to accent the beauty of the location. The condo is beautifully decorated with local and tropical art and furniture. We value cleanliness, comfort, beauty and exceptional service and hospitality. Whenever we have the chance, we escape to our condo and feel the peace and tranquility the space and surrounding location has to offer. We return to our busy lives feeling refreshed and invite you to do the same.

Oct. 24 – 31

$319 CAD per night

Guest favourite

Condo in Kaunakakai

4.94 out of 5 average rating, 182 reviews

Welcome to Hotel Molokai, Unit 102...

*This unit is located on the island of Moloka'i, not MAUI. Welcome to Moloka'i, where time slows down and you're able to relax and unwind. Hotel Moloka'i is a hotel convenient located on the outskirts of Kaunakakai town. Whether you're on Moloka'i for business or pleasure, our unit offers you a comfortable place to stay. Enjoy beaches all to yourself, go on hikes and listen to live music at Hiro's 'Ohana Grill.

Sep. 7 – 14

$165 CAD per night

Superhost

Condo in Kihei

4.79 out of 5 average rating, 99 reviews

Your Paradise Awaits at Sunny Kihei Kai Nani!

Step into your own private tropical oasis! This adorable ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This condo boasts an open and airy living space you will love. Enjoy your favorite grilled meals al fresco on the Weber gas BBQ grill and table with seating for four, just steps from your lanai.

Jun. 6 – 13

$296 CAD per night

Guest favourite

Apartment in Kihei

4.84 out of 5 average rating, 249 reviews

Your Vacation Right Across from Sandy Beach

Located in Kihei, this private and spacious 750 square foot condo provides you with all the comfort and resort-like amenities you could possibly need. Adjacent to the upscale town of Wailea, which features world class resorts, fine dining, and shopping, Kihei boasts beautiful coastlines and amazing weather. Come enjoy scenic South Maui without paying luxury prices.

Jun. 18 – 25

$267 CAD per night