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Leeward Vacation Rentals & Homes - 86 Rentals Available

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86 Vacation rentals

1 / 37

Leeward Villa

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

Responds fast! Avg. 1 hour 21 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 21 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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1 / 36

Leeward Villa

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

$7,312.00

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from $7,312.00 / night

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1 / 11

Leeward Villa

  • 5
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$6,338.00

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from $6,338.00 / night

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(1)

1 / 38

Leeward Villa

  • 1
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$6,728.00

Excellent (1 reviews)

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from $6,728.00 / night

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1 / 14

Leeward Villa

  • 1
  • 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,974.00

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from $1,974.00 / 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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(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

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(14)

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

$300.00

Excellent (14 reviews)

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from $300.00 / 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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(43)

1 / 42

Providenciales Villa - 5.9 miles away

  • 10
  • 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 (43 reviews)

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from $5,000.00 / 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 / 22

Turtle Cove Condo - 5 miles away

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

$258.00

Very Good (4 reviews)

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from $258.00 / 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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(1)

1 / 41

Grace Bay House - 0.1 miles away

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

Responds fast! Avg. 1 hour 35 minutes

$1,064.00

Excellent (1 reviews)

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from $1,064.00 / night

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(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. 1 hour 35 minutes

Certificate of Excellence

$982.00

Excellent (17 reviews)

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from $982.00 / night

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1 / 15

The Bight Settlement Villa - 5.3 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$620.00

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from $620.00 / night

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1 / 27

Grace Bay Villa - 0.1 miles away

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

$2,242.00

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from $2,242.00 / night

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1 / 17

The Bight Settlement Villa - 5.1 miles away

  • 1
  • 2
  • 7 nights min
  • Child friendly
  • Air conditioning

$502.00

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from $502.00 / night

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1 / 31

The Bight Settlement Villa - 5.1 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,365.00

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from $1,365.00 / night

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1 / 14

Grace Bay Villa - 0.1 miles away

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,364.00

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from $2,364.00 / 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. 1 hour 21 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

$974.00

Excellent (2 reviews)

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from $974.00 / 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 21 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 / 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

$1,451.00

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from $1,451.00 / 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 / 41

Long Bay Beach Villa - 3.1 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$843.00

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from $843.00 / night

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1 / 38

Long Bay Beach Villa - 3.1 miles away

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

$645.00

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from $645.00 / 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

$6,001.00

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from $6,001.00 / 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

$5,401.00

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from $5,401.00 / 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 / 23

Grace Bay Villa - 5.1 miles away

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$514.00

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from $514.00 / 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 / 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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