Vacation Rentals with Pool in Maui

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Filtering by: Swimming pool

2,449 vacation rentals

(10) Very Good 

21

Maui Beautiful Westside Beach Front Condo See May- Oct Discounted Reduced Rates

Maui / Lahaina

Lahaina apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“Paradise” The condo was very nice. It had everything we needed. We had a wonderful time there!! Thanks for being a part of making our vacation perfect!! Randy May
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Price per night from

$186

Price per night from

$186

(126) Excellent 

33

Kamaole Sands 10-211 "OCEAN VIEW" Remodeled/Full A/C /Large Lanai/Great reviews!

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Perfect - just as described!” Kameole Sands is an ideal location - close to beaches, restaurants & easy drives to more. The unit is updated, spotlessly clean and has all one needs ( and more) to enjoy the paradise that is Maui. View from the lanai is
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Price per night from

$150

Responds fast!
avg. 50 minutes

Price per night from

$150

(20) Excellent 

40

SPECIAL: Maui Vista- only $107/night for avail nights in April

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“Close to great beaches all you need is your flip flops” This is our 3rd year staying in this condo. It is clean and has all the amenities including beach toys,coolers,and even suntan lotion. The property has a place to grill and a pool. It also has a
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Price per night from

$107

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$107

(5) Excellent 

28

One-of-a-Kind Maui Getaway!

Maui / Wailea

Wailea house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool

Price per night from

$1,340

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$1,340

(63) Excellent 

16

Milowai #204--Tropical Maui Oceanfront Condo

Maui / Maalaea

Maalaea apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
“Fabulous!” It is the perfect location on the island. Easy to get to everything. Right on the water w/beautiful views of the sunrise over Halekuela. Enjoying all the sea turtle activity from the lanai is always special. Delightful & relaxing!
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Price per night from

$146

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$146

(55) Excellent 

30

Direct Oceanfront Valley Isle Unit 1009

Maui / Lahaina

Lahaina apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Fabulous Sunsets and Whale Watching - Room 1009!” I had the great fortune to come to Maui during whale season and was able to see all of the action from my lanai in Room 1009. This room at the Valley Isle is just spectacular! It is private, beautifull
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Price per night from

$190

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$190

(4) Excellent 

24

Royal Kahana #815 - Stunning Views! Free Wi-Fi!

Maui / Lahaina

Lahaina apartment

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$288

Responds fast!
avg. 57 minutes

Price per night from

$288

(78) Excellent 

26

Direct Oceanfront Studio Unit 307 -Valley Isle Resort

Maui / Lahaina

Lahaina apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“Cute condo” Looking for a small quaint condo? This is it. Very nicely decorated. Loved it! Very relaxing. Beach right outside the patio. Hearing the waves at night was very soothing. Location great. Just a ride away to shopping n eateries. Beach right
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Price per night from

$155

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$155

(15) Very Good 

49

Palms at Wailea Unit #2305 1Bd/2Ba Quiet, Very Private! Near Beach, Sleeps 2

Maui / Wailea

Wailea apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great for Couples” For those of us who hate living in hotels, or paying for services we don't use, this 1 bedroom/2 bathroom condo is perfect. It feels and looks even larger than the photos and is equipped with a full kitchen, that is very well stocke
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Price per night from

$189

Responds fast!
avg. 5 minutes

Price per night from

$189

(10) Excellent 

21

Kihei Bay Vista #A-205 Ocean View 1 Bedroom 1 Bath Near Beach Great Rates!!

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“A-205 Kihei Bay Vistas” Lovely condo. Very close to the beaches. Lots of useful amenities and beach gear.
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Price per night from

$109

Responds fast!
avg. 5 minutes

Price per night from

$109

(28) Excellent 

19

Maui Oceanfront Paradise See April- Oct Specials Act Fast

Maui / Lahaina

Lahaina apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children
“Beautiful Ocean Front Studio” My wife and I just returned from our stay in this beautiful studio and we were very pleased. Thomas, the owner, was very responsive and great to work with! The location at the Royal Kahana is great with many places to w
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Price per night from

$176

Price per night from

$176

(10) Excellent 

58

# Beautiful Kihei Maui Condo - Menehune Shores 126

Maui / Kihei

Kihei condo

2 6 4 nights min

  • 2 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“Felt right at home, great location” The condo was the perfect location for my family. I was glad the kitchen was fully stocked and had everything we needed. The beach chairs, toys and other gear provided were put to great use and it was nice we didn
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Price per night from

$220

Price per night from

$220

(17) Very Good 

28

Waiohuli Beach Hale #B-206 Ocean View Oceanfront 1Bd/1Ba Great Rates Sleeps 4

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Maui journey july 2013” 5 nights journey in Kihei to explore major key spots of the island.
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Price per night from

$120

Responds fast!
avg. 5 minutes

Price per night from

$120

(3) Very Good 

17

Maui Sunset 401B Remodeled w/ full kitchen and partial ocean view.

Maui / Kihei

Kihei apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Great Getaway from Saskatchewan” Very Satisfied. Wendi was very helpful and professional
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Price per night from

$180

Price per night from

$180

(12) Excellent 

22

Updated Spacious 3 Bdrm. Wailea Ocean View Condo

Maui / Wailea

Wailea apartment

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Great condo!” We absolutely loved the condo.  It was well appointed and spacious.  We hosted a gathering of about 20 people and the kitchen, dining, living spaces combined with the lanai comfortably held that many people. The location was perfect, ri
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Price per night from

$285

Responds fast!
avg. 3 hours 0 minutes

Price per night from

$285

(4) Excellent 

24

EXTRAORDINARY RATE FOR KAPALUA LUXURY September 8-

Maui / Kapalua

Kapalua villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$230

Price per night from

$230

(3) Excellent 

28

Kihei Kai Nani #2-210 Across From Kamaole Beach #2 Great Rates Sleeps 4

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great Home Base in Maui” A great value with all the amenities we were looking for - air conditioning, updated kitchen, laundry, free parking. Property is very updated and well maintained.
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Price per night from

$110

Responds fast!
avg. 5 minutes

Price per night from

$110

(6) Excellent 

21

Wailea Orchid Villa - Panoramic Views! 3 Bd/3 Ba

Maui / Wailea

Wailea villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“Wonderful stay in the Penthouse Villa...” Service: 5 Stars - The owner was very prompt in replying to email with questions, concerns. Concierge and front desk staff were courteous and very helpful. The bellman/staff even brought all of our luggage
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Price per night from

$1,050

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$1,050

14

King Protea Residence

Maui / Lahaina

Lahaina villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,725

Price per night from

$1,725

23

Kihei Bay Vista #C-106 Best Location, Garden View, Sleeps 4, Great Rates!

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$109

Responds fast!
avg. 5 minutes

Price per night from

$109

14

Special! Maui Sunset 502B, 1 BR, 2 BA with Partial Ocean View

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$150

Price per night from

$150

(31) Very Good 

17

Kihei Bay Surf #119 Completely Remodeled Show Stopper! Great Rates! Sleeps 3.

Maui / Kihei

Kihei studio

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Kihei Stay” I would consider coming back. Very affordable pricing. The unit has been upgraded (except for the TV). We did spot one cockroach, but those are native to the island. Location isn't uber busy, which I recommend for a mellow/relaxing vacatio
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Price per night from

$99

Responds fast!
avg. 5 minutes

Price per night from

$99

(5) Very Good 

26

Kihei Bay Surf #226 Studio Sleeps 3 Convenient, Near Beach, Great Rates!

Maui / Kihei

Kihei studio

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“more than expected!” To our suprise the unit had boggie boards, louged chairs,umbrella for beach usaged. Kitchen fully equip however the ice maker is not hook up with the water supply,(w/c can be easily fix). The condo right across from the small beac
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Price per night from

$89

Responds fast!
avg. 5 minutes

Price per night from

$89

(1) Very Good 

38

Palms at Wailea #1102 Probably the best ocean view at the Palms at Wailea!

Maui / Wailea

Wailea apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
“Great place to stay for the price” We loved the location and views from our units. The pool was warm and quite nice despite having many restrictions. The units were clean and nice looking however many of the amenities promised (ie. beach equipment) we
…see more

Price per night from

$295

Responds fast!
avg. 5 minutes

Price per night from

$295

(17) Excellent 

23

Kamaole Sands 1-303 "OCEAN VIEW" Remodeled/Full A/C / Large Lanai/Great reviews!

Maui / Kihei

Kihei condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$150

Responds fast!
avg. 50 minutes

Price per night from

$150

(23) Excellent 

Certificate of Excellence

30

Papakea Resort, Unit G-407

Maui / Ka'anapali

Ka'anapali apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Beautiful condo and with breathtaking views...your own little bit of paradise” The condo is located in a most desirable and sought after area of the western coast of Maui. Being right on the beach, you will have breataking views and depending on the t
…see more

Certificate of Excellence

Price per night from

$270

Responds fast!
avg. 3 hours 14 minutes

Price per night from

$270

20

Kihei Bay Surf #208 Remodeled 2nd Flr Studio, Part. Ocean View, Great Rates!

Maui / Kihei

Kihei studio

Studio 3 min stay varies

  • Studio
  • sleeps 3
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$89

Responds fast!
avg. 5 minutes

Price per night from

$89

(26) Excellent 

14

VALLEY ISLE CONDOMINIUM RESORT Oceanfront

Maui / Lahaina

Lahaina hotel apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Hard to find a better view with a whale guarantee!” If you spend 10 minutes looking straight out at Molokai, you are bound to see a whale. While many boast of a spectecular view, Valley Isle delivers! The room has everything you need for a romantic
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Price per night from

$162

Responds fast!
avg. 3 hours 19 minutes

Price per night from

$162

(25) Excellent 

Certificate of Excellence

35

Maui Paradise 2018 Award Sun, Sand & Sea 2 BR Vacation Condo at Maui Kamaole!

Maui / Kihei

Kihei apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
“Will return to Maui!!” We stayed in this lovely 2-bedroom condo in March 2014. Everything you could ask for was supplied right down to beach towels & coolers to take to the beach and the "Hawaii for Dummies" book. Used our GPS once and that was jus
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Certificate of Excellence

Price per night from

$252

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$252

(14) Excellent 

26

Kahana Reef 212

Maui / Lahaina

Lahaina condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
“Paradise perfect” The view was fabulous and the location of the condo was great! We enjoyed coming”home” and sitting on the deck and enjoying the views! The condo could use a little updating and the bedroom carpet replaced. The only drawbacks we fo
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Price per night from

$125

Responds fast!
avg. 3 hours 23 minutes

Price per night from

$125

(23) Excellent 

19

OCEAN FRONT WITH AMAZING VIEWS

Maui / Lahaina

Lahaina apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Maui at its best!” We stayed for last two weeks of June, 2013. Wow, could not come up with a complaint if I tried. The unit is recently updated & well stocked. So much is provided & everything is first rate. Everything you need is just a 3-5 min wa
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Price per night from

$287

Price per night from

$287

(42) Excellent 

29

Kamaole Sands -inner court - granite -views- Open winter

Maui / Kihei

Kihei apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Great place to stay!” We had a wonderful time in Maui and we owe a great part of that to our stay in this condo. It was the perfect retreat and place to come home to after the day's outings. The grounds are beautiful and the condo complex is well lo
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Price per night from

$145

Responds fast!
avg. 3 hours 27 minutes

Price per night from

$145

(1) Very Good 

24

Renovated! Ocean views! New AC! 2 bedroom ,Top Floor!!

Maui / Lahaina

Lahaina condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Price per night from

$210

Price per night from

$210

(22) Very Good 

26

Kihei Bay Vista #D-208 1Bd/1Ba, Great Location Steps from the Beach. Sleeps 4

Maui / Kihei

Kihei apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Easy to arrange and surpassed exppectations” First time renting a vacation property through the internet, the overall experience surpassed what I expected. It was easy to reserve and coordinate with the property management. They were friendly and help
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Price per night from

$104

Responds fast!
avg. 5 minutes

Price per night from

$104

(6) Excellent 

15

Hale Kai 217 - Maui Oceanfront Majesty with Old Hawaii Spirit

Maui / Lahaina

Lahaina apartment

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Ask about children
“A great vacation at Hale Kai” A most pleasant experience. Valerie Kane is the best manager the property ever had in the 40 years of our vacations at Hale Kai
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Price per night from

$140

Price per night from

$140

(17) Excellent 

24

The most Gorgeous 2bd2ba OV Villa in Kapalua!

Maui / Kapalua

Kapalua hotel apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
“Every morning on the patio, with a cup of coffee, made us realiz” We had a wonderful time in Maui and your home was so comfortable and up to date. It had everything we needed, and the coffee table book you put together (with all the suggestions of th
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Price per night from

$357

Responds fast!
avg. 2 hours 16 minutes

Price per night from

$357

(14) Excellent 

22

Kahana Sunset 2 BR Condo, Ocean View, Great Beach

Maui / Lahaina

Lahaina apartment

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“A decision you won't regret!” We recently stayed in E-6 and absolutely loved it. From the ease of being able to book the condo to the great service we received from Mike. He was always willing to help with all and any questions I had with not only the
…see more

Price per night from

$220

Price per night from

$220

54

Palms at Wailea #305 A/C Throughout, Close to Pool, Nicely Appointed Sleeps 6

Maui / Kihei

Kihei apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$245

Responds fast!
avg. 5 minutes

Price per night from

$245