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Leeward 2-bedroom Vacation Rentals, Homes & More - 148 Rentals Available.

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148 Vacation rentals

Filters applied: 2+ Bedrooms

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 / 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

(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

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

(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

(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

$5,000.00

Excellent (25 reviews)

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from $5,000.00 / night

(6)

1 / 28

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 31 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

(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 / 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

(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

(3)

1 / 26

Providenciales Villa - 10.1 miles away

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$562.00

Excellent (3 reviews)

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from $562.00 / night

(1)

1 / 44

Turtle Cove Villa - 5 miles away

  • 6
  • 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,193.00

Excellent (1 reviews)

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from $2,193.00 / 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 / 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

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

(5)

1 / 22

Providenciales Villa - 5 miles away

  • 4
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$829.00

Excellent (5 reviews)

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from $829.00 / 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 / 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

(4)

1 / 17

Grace Bay Villa - 0.1 miles away

  • 4
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,271.00

Excellent (4 reviews)

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from $1,271.00 / night