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Leeward 2-bedroom Vacation Rentals, Homes & More - 59 Rentals Available.

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59 Vacation rentals

Filters applied: 2+ Bedrooms

1 / 37

Leeward Villa

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

Responds fast! Avg. 1 hour 25 minutes

$1,088.00

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from $1,088.00 / night

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1 / 12

Leeward Villa

  • 3
  • 6
  • 5 nights min
  • Child friendly

Responds fast! Avg. 1 hour 25 minutes

$630.00

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from $630.00 / 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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Your search has been expanded 11 miles to include more rentals

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

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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 / 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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(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 / 19

Providenciales Cottage - 0.1 miles away

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

Responds fast! Avg. 2 hours 5 minutes

$458.00

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from $458.00 / night

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(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

$229.00

Excellent (4 reviews)

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from $229.00 / night

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(10)

1 / 23

Providenciales Villa - 10.2 miles away

  • 9
  • 18
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“This is about 10 years going to Provo. I absolutely love Emerald Shores. Allows the privacy and quiet I want and access to beautiful views and enough room to stretch out.. hang out with friends or just find a lonely little corner to chill...”
- Review left on 02/22/2019

$1,637.00

Very Good (10 reviews)

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from $1,637.00 / night

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(19)

1 / 43

Turtle Cove Villa - 4.9 miles away

  • 3
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$428.00

Very Good (19 reviews)

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from $428.00 / night

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(15)

1 / 40

Turtle Cove Villa - 4.9 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly

$298.00

Excellent (15 reviews)

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from $298.00 / 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. 1 hour 23 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

$2,233.00

Excellent (6 reviews)

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from $2,233.00 / night

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(51)

1 / 42

Providenciales Villa - 5.9 miles away

  • 10
  • 22
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Island was quiet and even more beautiful than we remember. We revelled in our time away. Everyone was wonderful and kind and we were thrilled to be able to enjoy the white sands and perfect sea...”
- Review left on 08/01/2020

$5,000.00

Excellent (51 reviews)

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from $5,000.00 / night

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1 / 31

The Bight Settlement Villa - 5.5 miles away

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

$4,200.00

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from $4,200.00 / 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 / 24

Grace Bay Villa - 0.1 miles away

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

$15,000.00

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from $15,000.00 / 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

$2,025.00

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from $2,025.00 / night

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1 / 37

Grace Bay Villa - 0.1 miles away

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

$10,850.00

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from $10,850.00 / night

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1 / 13

Grace Bay Villa - 0.1 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1,450.00

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from $1,450.00 / 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 / 25

Grace Bay Villa - 0.1 miles away

  • 4
  • 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 / 45

Grace Bay Villa - 1.5 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$6,000.00

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from $6,000.00 / night

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1 / 58

Grace Bay Villa - 0.1 miles away

  • 4
  • 10
  • 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 / 49

Grace Bay Villa - 0.1 miles away

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

$5,400.00

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from $5,400.00 / night

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(2)

1 / 33

Turtle Cove Villa - 10.4 miles away

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

$549.00

Excellent (2 reviews)

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from $549.00 / night

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(9)

1 / 35

The Bight Settlement Villa - 4.9 miles away

  • 3
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$681.00

Excellent (9 reviews)

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from $681.00 / night

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1 / 54

The Bight Settlement Villa - 4.9 miles away

  • 6
  • 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$3,071.00

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from $3,071.00 / night

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(1)

1 / 22

Long Bay Beach Villa - 3.3 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,141.00

Very Good (1 reviews)

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from $1,141.00 / night

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1 / 50

Long Bay Beach House - 3.1 miles away

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

$10,000.00

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from $10,000.00 / night

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(3)

1 / 32

Turtle Cove Villa - 10.1 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$446.00

Excellent (3 reviews)

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from $446.00 / night

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1 / 21

The Bight Settlement Cottage - 4.9 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$390.00

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from $390.00 / night

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1 / 42

Turtle Cove House - 6.1 miles away

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

$971.00

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from $971.00 / night

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(12)

1 / 43

The Bight Settlement House - 5.7 miles away

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

$1,543.00

Excellent (12 reviews)

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from $1,543.00 / night

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(2)

1 / 25

The Bight Settlement Villa - 5 miles away

  • 5
  • 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,414.00

Very Good (2 reviews)

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from $1,414.00 / night

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(11)

1 / 43

Turtle Cove Villa - 10.4 miles away

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$663.00

Excellent (11 reviews)

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from $663.00 / night

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1 / 36

Five Cays Settlement Villa - 2.1 miles away

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,700.00

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from $1,700.00 / night

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(4)

1 / 35

The Bight Settlement Villa - 3.4 miles away

  • 4
  • 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,017.00

Excellent (4 reviews)

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from $1,017.00 / night

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(5)

1 / 21

Turtle Cove Villa - 9.8 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$545.00

Excellent (5 reviews)

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from $545.00 / night

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(3)

1 / 32

The Bight Settlement Villa - 5 miles away

  • 3
  • 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$687.00

Excellent (3 reviews)

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from $687.00 / night

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