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Leeward Vacation Rentals & Homes - 197 Rentals Available

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197 Vacation rentals

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

(2)

1 / 15

Leeward Villa

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

Responds fast! Avg. 31 minutes

$1,661.00

Excellent (2 reviews)

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from $1,661.00 / night

(1)

1 / 29

Leeward Villa

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

$6,000.00

Excellent (1 reviews)

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from $6,000.00 / night

(1)

1 / 20

Leeward House

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

$501.00

Excellent (1 reviews)

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from $501.00 / night

1 / 25

Leeward Villa

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

Responds fast! Avg. 3 hours 35 minutes

$1,300.00

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from $1,300.00 / night

1 / 41

Leeward Villa

  • 1
  • 12
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$6,000.00

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from $6,000.00 / night

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

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

1 / 61

Leeward Villa

  • 6
  • 12
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$1,700.00

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from $1,700.00 / night

1 / 35

Leeward Villa

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

Responds fast! Avg. 1 hour 15 minutes

$1,480.00

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from $1,480.00 / night

1 / 31

Leeward Villa

  • 7
  • 14
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$9,000.00

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from $9,000.00 / night

1 / 28

Leeward Villa

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

Responds fast! Avg. 1 hour 15 minutes

$1,300.00

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from $1,300.00 / night

1 / 26

Leeward Villa

  • 8
  • 12
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$8,300.00

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from $8,300.00 / night

1 / 26

Leeward Villa

  • 8
  • 16
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$10,350.00

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from $10,350.00 / night

1 / 26

Leeward Villa

  • 8
  • 10
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$6,800.00

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from $6,800.00 / night

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

1 / 23

Leeward Villa

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

Responds fast! Avg. 1 hour 15 minutes

$850.00

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from $850.00 / night

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

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

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

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

(4)

1 / 22

Turtle Cove Condo - 5 miles away

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

$235.00

Very Good (4 reviews)

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from $235.00 / night

(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

$575.00

Excellent (13 reviews)

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from $575.00 / night

(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

(11)

1 / 26

Turtle Cove Villa - 4.9 miles away

  • 2
  • 5
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly

$385.00

Excellent (11 reviews)

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from $385.00 / night

(15)

1 / 34

Turtle Cove Villa - 4.9 miles away

  • 3
  • 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$579.00

Very Good (15 reviews)

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from $579.00 / night

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

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 3 minutes

$458.00

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from $458.00 / night

(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

1 / 14

Grace Bay Villa - 1 miles away

  • 1
  • 2
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$775.00

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from $775.00 / night

(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

(4)

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

Excellent (4 reviews)

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from $573.00 / night

1 / 19

Providenciales Apartment - 11 miles away

  • 2
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

$630.00

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from $630.00 / night

1 / 18

Grace Bay Villa - 0.1 miles away

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

Responds fast! Avg. 1 hour 15 minutes

$4,950.00

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from $4,950.00 / night

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

1 / 20

Grace Bay Villa - 0.1 miles away

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

$7,718.00

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from $7,718.00 / night

1 / 23

Turtle Cove Villa - 6.1 miles away

  • 1
  • 8
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$2,250.00

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from $2,250.00 / night

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

(1)

1 / 10

Grace Bay Villa - 0.1 miles away

  • 2
  • 4
  • min stay varies
  • Child friendly

$1,450.00

Excellent (1 reviews)

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from $1,450.00 / night

1 / 44

Long Bay Beach Villa - 3.1 miles away

  • 1
  • 14
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 1 hour 15 minutes

$6,000.00

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from $6,000.00 / night