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Leeward Vacation Rentals & Homes with Swimming Pool - 130 Rentals Available.

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130 Vacation rentals

Filters applied: Swimming pool

1 / 16

Leeward Villa

  • 6
  • 12
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1,857.00

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from $1,857.00 / night

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(2)

1 / 15

Leeward Villa

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 32 minutes

$1,661.00

Excellent (2 reviews)

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from $1,661.00 / night

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(1)

1 / 29

Leeward Villa

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$5,750.00

Excellent (1 reviews)

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from $5,750.00 / night

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1 / 25

Leeward Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,300.00

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from $1,300.00 / night

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1 / 11

Leeward Villa

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,100.00

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from $2,100.00 / night

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1 / 36

Leeward Villa

  • 8
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$17,745.00

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from $17,745.00 / night

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1 / 36

Leeward Villa

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$15,225.00

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from $15,225.00 / night

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1 / 36

Leeward Villa

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$11,392.00

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from $11,392.00 / night

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1 / 19

Leeward Villa

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$3,938.00

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from $3,938.00 / night

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Your search has been expanded 11 miles to include more rentals

(16)

1 / 26

Grace Bay Villa - 0.1 miles away

  • 3
  • 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 49 minutes

$983.00

Excellent (16 reviews)

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from $983.00 / night

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(2)

1 / 43

Grace Bay Villa - 0.1 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 32 minutes

“A very beautiful home with private pool and lovely outdoor living area. 2 minute walk to a most beautiful stretch of Grace Bay beach. Great outdoor grill. Fully equipped kitchen. We stayed here for two weeks and wish it had been three. Brita was a...”
- Review left on 01/26/2017

$1,432.00

Excellent (2 reviews)

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from $1,432.00 / night

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1 / 27

Grace Bay Villa - 0.1 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$540.00

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from $540.00 / night

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(4)

1 / 22

Turtle Cove Condo - 5 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$235.00

Very Good (4 reviews)

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from $235.00 / night

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(4)

1 / 23

Providenciales Villa - 10.2 miles away

  • 9
  • 18
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$1,963.00

Excellent (4 reviews)

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from $1,963.00 / night

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(1)

1 / 20

Providenciales Villa - 6.3 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
“The house was perfect in every way. Owner Tina was very responsive to every email and question Shelly (onsite manager) was great, she helped us out on the last day. Anybody considering a quiet house in a great area must look at this one. Western...”
- Review left on 06/05/2016

$414.00

Excellent (1 reviews)

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from $414.00 / night

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(13)

1 / 25

Turtle Cove Cottage - 5.9 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“Xanadu is truly a one of a kind escape from reality! The location was absolutely beautiful and Carla, Yamali, and all the rest of the staff were AMAZING! Linda was wonderful with all of the logistics (and she is a pretty awesome person too!)Samsara...”
- Review left on 05/12/2017

$550.00

Excellent (13 reviews)

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from $550.00 / night

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(15)

1 / 27

Turtle Cove Villa - 4.9 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$393.00

Very Good (15 reviews)

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from $393.00 / night

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(1)

1 / 15

Providenciales Villa - 5.9 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We rented 5 Little Cays Villa for a 4 couples get away. From the time we walked into the villa, til the time we left we had the most amazing time. The photos are spot on, but they don't do it justice. The best part of the Villa is the beachfront....”
- Review left on 10/17/2016

$1,071.00

Excellent (1 reviews)

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from $1,071.00 / night

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1 / 19

Providenciales Cottage - 0.1 miles away

  • 2
  • 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 6 minutes

$458.00

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from $458.00 / night

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(25)

1 / 40

Providenciales Villa - 5.9 miles away

  • 7
  • 22
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Samsara Villa is amazing. From the moment you walk in and see the view of the infinity double pool, the jacuzzi and the turquoise water in the background, you know you are about to relax in luxury. Each suite is totally separate with its own...”
- Review left on 05/09/2017

$4,500.00

Excellent (25 reviews)

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from $4,500.00 / night

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1 / 25

Grace Bay House - 0.1 miles away

  • 4
  • 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 49 minutes

$1,064.00

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from $1,064.00 / night

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(7)

1 / 28

Providenciales Villa - 5.6 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“White Osprey far surpassed our expectations. The villa is superb in taste, location and the views are to-die-for. Christina is a gracious host and she does a wonderful job making sure her guests feel welcome and comfortable. When we arrived, she...”
- Review left on 12/02/2016

$450.00

Excellent (7 reviews)

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from $450.00 / night

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(6)

1 / 28

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 32 minutes

“Our family of six had the most wonderful vacation! The description of the house does not do it justice, it was incredible! The house was beautifully decorated, and had all desired amenities. The outdoor area and pool were just as luxurious. The...”
- Review left on 01/05/2017

$2,577.00

Excellent (6 reviews)

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from $2,577.00 / night

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(1)

1 / 14

Providenciales Apartment - 11 miles away

  • 2
  • 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

$745.00

Very Good (1 reviews)

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from $745.00 / night

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(1)

1 / 27

Providenciales Villa - 5.7 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,929.00

Excellent (1 reviews)

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from $1,929.00 / night

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1 / 20

Turtle Cove Penthouse - 11 miles away

  • 3
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$687.00

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from $687.00 / night

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(2)

1 / 15

Providenciales Apartment - 10.9 miles away

  • 1
  • 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$401.00

Average (2 reviews)

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from $401.00 / night

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(3)

1 / 21

Providenciales Apartment - 11 miles away

  • 2
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
“We have been going back to Providenciales for over 10 years now. We have mostly stayed at the Northwest point. We have been in many units and this one was particularly nice because of it's high ceilings, furnishings, and attention to detail....”
- Review left on 02/27/2016

$573.00

Very Good (3 reviews)

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from $573.00 / night

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(1)

1 / 20

Providenciales Villa - 5.3 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$471.00

Excellent (1 reviews)

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from $471.00 / night

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(2)

1 / 19

Providenciales Villa - 5.3 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Air conditioning

$471.00

Very Good (2 reviews)

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from $471.00 / night

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1 / 41

Grace Bay Villa - 0.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,300.00

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from $2,300.00 / night

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1 / 16

Turtle Cove Apartment - 11 miles away

  • 3
  • 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

$916.00

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from $916.00 / night

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1 / 49

Grace Bay Villa - 0.1 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$7,000.00

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from $7,000.00 / night

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1 / 30

Grace Bay Villa - 0.1 miles away

  • 10
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$10,350.00

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from $10,350.00 / night

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1 / 11

Grace Bay Villa - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,425.00

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from $2,425.00 / night

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1 / 14

Grace Bay Villa - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,782.00

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from $2,782.00 / night

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1 / 20

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$7,719.00

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from $7,719.00 / night

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1 / 18

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,950.00

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from $4,950.00 / night

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1 / 32

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

$4,950.00

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from $4,950.00 / night

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1 / 27

Grace Bay Villa - 0.1 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,462.00

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from $4,462.00 / night

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