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Leeward Vacation Rentals & Homes - 111 Rentals Available

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111 Vacation rentals

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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

1 / 5

Leeward Villa

  • 3
  • 6
  • min stay varies
  • Child friendly

Responds fast! Avg. 1 hour 0 minutes

$682.00

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from $682.00 / night

1 / 37

Leeward Villa

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

Responds fast! Avg. 1 hour 0 minutes

$1,260.00

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from $1,260.00 / night

(2)

1 / 29

Leeward Villa

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

$6,000.00

Excellent (2 reviews)

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from $6,000.00 / night

1 / 25

Leeward Villa

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

Responds fast! Avg. 3 hours 15 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

$1,881.00

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from $1,881.00 / night

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

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

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

1 / 25

Leeward Villa

  • 1
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,833.00

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from $1,833.00 / night

1 / 14

Leeward Villa

  • 1
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,115.00

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from $2,115.00 / night

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

Your search has been expanded 10.4 miles to include more rentals

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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

$4,000.00

Excellent (30 reviews)

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from $4,000.00 / night

(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. 1 hour 0 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

$1,088.00

Excellent (2 reviews)

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from $1,088.00 / night

(17)

Certificate of Excellence

1 / 42

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

Certificate of Excellence

$983.00

Excellent (17 reviews)

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from $983.00 / night

1 / 28

Grace Bay Villa - 5.1 miles away

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

$6,000.00

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from $6,000.00 / night

(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

$349.00

Excellent (17 reviews)

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from $349.00 / night

1 / 27

Grace Bay Villa - 0.1 miles away

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

Responds fast! Avg. 1 hour 31 minutes

$540.00

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from $540.00 / night

(8)

1 / 28

Providenciales Villa - 5.6 miles away

  • 2
  • 4
  • 7 nights min
  • 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 (8 reviews)

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from $450.00 / night

(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

(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

(14)

1 / 28

Turtle Cove Villa - 4.9 miles away

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

$216.00

Excellent (14 reviews)

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from $216.00 / night

(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 0 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

(3)

1 / 17

Providenciales Villa - 5.2 miles away

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414.00

Excellent (3 reviews)

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from $414.00 / night

(1)

1 / 35

Turtle Cove Villa - 5.1 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$629.00

Excellent (1 reviews)

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from $629.00 / night

(3)

1 / 28

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

(4)

1 / 17

Grace Bay Villa - 0.1 miles away

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

$1,114.00

Excellent (4 reviews)

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from $1,114.00 / night

(2)

1 / 25

Turtle Cove Villa - 5.1 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$757.00

Excellent (2 reviews)

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from $757.00 / night

(5)

1 / 22

Providenciales Villa - 9.8 miles away

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

$671.00

Excellent (5 reviews)

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from $671.00 / night

(21)

1 / 39

Long Bay Beach Villa - 3.4 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,557.00

Excellent (21 reviews)

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from $1,557.00 / night

1 / 45

Turtle Cove Villa - 10.4 miles away

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

$643.00

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from $643.00 / night

1 / 62

Turtle Cove Villa - 10.4 miles away

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$786.00

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from $786.00 / night

(8)

1 / 17

Providenciales Villa - 9.8 miles away

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$414.00

Excellent (8 reviews)

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from $414.00 / night

(2)

1 / 20

Providenciales Villa - 5.1 miles away

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$314.00

Excellent (2 reviews)

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from $314.00 / night

(1)

1 / 25

Turtle Cove Villa - 5.1 miles away

  • 5
  • 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,257.00

Excellent (1 reviews)

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from $1,257.00 / night

(1)

1 / 19

Turtle Cove Villa - 5.1 miles away

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

$786.00

Excellent (1 reviews)

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from $786.00 / night

1 / 27

Turtle Cove Villa - 5.1 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$757.00

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from $757.00 / night

(1)

1 / 33

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 / 39

Five Cays Settlement Villa - 2.1 miles away

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

$1,700.00

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from $1,700.00 / night

(1)

1 / 25

Providenciales Villa - 5.2 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$757.00

Excellent (1 reviews)

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from $757.00 / night