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Leeward 2-bedroom Vacation Rentals, Homes & More - 134 Rentals Available.

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134 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

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1 / 5

Leeward Villa

  • 3
  • 6
  • min stay varies
  • Child friendly

Responds fast! Avg. 36 minutes

$573.00

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from $573.00 / night

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1 / 37

Leeward Villa

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

Responds fast! Avg. 36 minutes

$1,260.00

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from $1,260.00 / night

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(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

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(1)

1 / 21

Leeward House

  • 3
  • 6
  • min stay varies
  • Air conditioning

$357.00

Excellent (1 reviews)

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from $357.00 / night

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1 / 11

Leeward Villa

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

$1,880.00

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from $1,880.00 / 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 / 35

Leeward Villa

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

Responds fast! Avg. 48 minutes

$1,480.00

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from $1,480.00 / night

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1 / 36

Leeward Villa

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

$15,886.00

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from $15,886.00 / night

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1 / 61

Leeward Villa

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

Responds fast! Avg. 48 minutes

$1,700.00

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from $1,700.00 / night

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1 / 28

Leeward Villa

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

Responds fast! Avg. 48 minutes

$1,300.00

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from $1,300.00 / night

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1 / 37

Leeward Villa

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

Responds fast! Avg. 48 minutes

$7,100.00

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from $7,100.00 / night

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1 / 37

Leeward Villa

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

Responds fast! Avg. 48 minutes

$10,850.00

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from $10,850.00 / night

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1 / 31

Leeward Villa

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

Responds fast! Avg. 48 minutes

$9,000.00

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from $9,000.00 / night

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1 / 37

Leeward Villa

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

Responds fast! Avg. 48 minutes

$8,700.00

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from $8,700.00 / night

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1 / 36

Leeward Villa

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

$13,630.00

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from $13,630.00 / night

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1 / 23

Leeward Villa

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

Responds fast! Avg. 48 minutes

$850.00

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from $850.00 / night

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1 / 36

Leeward Villa

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

$10,199.00

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from $10,199.00 / night

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1 / 19

Leeward Villa

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

$3,525.00

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from $3,525.00 / night

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Your search has been expanded 11 miles to include more rentals

(1)

1 / 27

Grace Bay House - 0.1 miles away

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

Responds fast! Avg. 2 hours 5 minutes

$1,064.00

Excellent (1 reviews)

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from $1,064.00 / night

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(30)

1 / 43

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

$5,250.00

Excellent (30 reviews)

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from $5,250.00 / night

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(16)

1 / 28

Grace Bay Villa - 0.1 miles away

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

Responds fast! Avg. 2 hours 5 minutes

$983.00

Excellent (16 reviews)

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from $983.00 / night

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(17)

1 / 31

Turtle Cove Villa - 4.9 miles away

  • 3
  • 7
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$298.00

Excellent (17 reviews)

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from $298.00 / 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

$2,491.00

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from $2,491.00 / night

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1 / 16

Turtle Cove Apartment - 11 miles away

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

Responds fast! Avg. 3 hours 45 minutes

$916.00

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from $916.00 / night

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(1)

1 / 15

Providenciales Villa - 5.9 miles away

  • 4
  • 8
  • min stay varies
  • 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 / 20

Turtle Cove Penthouse - 11 miles away

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

Responds fast! Avg. 3 hours 45 minutes

$687.00

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from $687.00 / night

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(9)

1 / 23

Providenciales Villa - 10.2 miles away

  • 9
  • 18
  • 7 nights min
  • 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

$1,963.00

Excellent (9 reviews)

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from $1,963.00 / night

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1 / 21

Grace Bay Villa - 3.8 miles away

  • 2
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 48 minutes

$1,048.00

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from $1,048.00 / night

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1 / 14

Grace Bay Villa - 1 miles away

  • 2
  • 4
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 48 minutes

$875.00

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from $875.00 / night

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(1)

1 / 34

Grace Bay Villa - 0.1 miles away

  • 5
  • 12
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 48 minutes

$2,564.00

Average (1 reviews)

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from $2,564.00 / night

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(9)

1 / 14

Grace Bay Villa - 1 miles away

  • 3
  • 6
  • min stay varies
  • Ask about children
  • Ask about pets

Responds fast! Avg. 48 minutes

$1,025.00

Excellent (9 reviews)

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from $1,025.00 / 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. 36 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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1 / 14

Grace Bay Villa - 0.1 miles away

  • 3
  • 8
  • min stay varies
  • Child friendly

$2,025.00

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from $2,025.00 / night

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(2)

1 / 34

Providenciales Villa - 10.6 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

Responds fast! Avg. 48 minutes

$826.00

Excellent (2 reviews)

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from $826.00 / night

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1 / 36

Grace Bay Villa - 0.1 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

$5,401.00

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from $5,401.00 / night

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1 / 49

Grace Bay Villa - 0.1 miles away

  • 4
  • 8
  • min stay varies
  • Child friendly

$2,300.00

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from $2,300.00 / 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. 36 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

$1,260.00

Excellent (2 reviews)

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from $1,260.00 / night

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1 / 12

Providenciales Villa - 6.1 miles away

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

Responds fast! Avg. 48 minutes

$2,000.00

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from $2,000.00 / night

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(13)

1 / 22

Providenciales Villa - 10.2 miles away

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

Responds fast! Avg. 48 minutes

$1,515.00

Very Good (13 reviews)

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from $1,515.00 / night

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