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Leeward Vacation Rentals & Homes with Swimming Pool - 60 Rentals Available.

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60 Vacation rentals

Filters applied: Swimming pool

1 / 37

Leeward Villa

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

Responds fast! Avg. 29 minutes

$1,317.00

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from $1,317.00 / night

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1 / 25

Leeward Villa

  • 4
  • 8
  • 4 nights min
  • 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 / 39

Leeward Villa

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

Responds fast! Avg. 29 minutes

$791.00

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from $791.00 / night

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1 / 40

Leeward Villa

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

$6,300.00

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from $6,300.00 / night

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1 / 19

Leeward Villa

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

$2,546.00

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from $2,546.00 / night

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Your search has been expanded 11 miles to include more rentals

(86)

1 / 46

Turtle Cove 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 (86 reviews)

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from $5,000.00 / night

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(10)

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

$1,603.00

Very Good (10 reviews)

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from $1,603.00 / 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

Responds fast! Avg. 2 hours 16 minutes

“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

$458.00

Excellent (4 reviews)

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from $458.00 / 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

Responds fast! Avg. 2 hours 16 minutes

$401.00

Average (2 reviews)

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from $401.00 / 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

Responds fast! Avg. 2 hours 16 minutes

$745.00

Very Good (1 reviews)

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from $745.00 / 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. 2 hours 16 minutes

$687.00

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from $687.00 / 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. 2 hours 16 minutes

$916.00

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from $916.00 / night

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(1)

1 / 24

Providenciales Villa - 8.6 miles away

  • 4
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“We loved this home. It was set up perfectly for our four couples. The beach location is unbelieveable and being so close to town was a bonus. The managment company was also very helpful and took care of our needs promptly. We definitly recommend this...”
- Review left on 09/08/2016

$1,429.00

Excellent (1 reviews)

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from $1,429.00 / night

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(22)

1 / 24

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

$450.00

Excellent (22 reviews)

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from $450.00 / night

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(6)

1 / 28

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 29 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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(2)

1 / 43

Grace Bay Villa - 0.1 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

Responds fast! Avg. 29 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

$1,020.00

Excellent (2 reviews)

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from $1,020.00 / night

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(1)

1 / 25

The Bight Settlement Cottage - 5.1 miles away

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

$293.00

Excellent (1 reviews)

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from $293.00 / night

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1 / 41

Turtle Cove House - 8.2 miles away

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

$1,829.00

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from $1,829.00 / night

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(3)

1 / 25

Turtle Cove Villa - 10.1 miles away

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

$700.00

Excellent (3 reviews)

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from $700.00 / night

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1 / 38

Turtle Cove House - 6.8 miles away

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

$1,643.00

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from $1,643.00 / night

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(9)

1 / 19

The Bight Settlement Villa - 5.2 miles away

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

$500.00

Excellent (9 reviews)

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from $500.00 / night

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(2)

1 / 16

The Bight Settlement House - 5.2 miles away

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

$586.00

Excellent (2 reviews)

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from $586.00 / night

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(3)

1 / 32

The Bight Settlement Villa - 5 miles away

  • 3
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$986.00

Excellent (3 reviews)

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from $986.00 / night

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1 / 25

Turtle Cove House - 8.2 miles away

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

$350.00

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from $350.00 / night

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(8)

1 / 23

The Bight Settlement Cottage - 5.1 miles away

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

$307.00

Very Good (8 reviews)

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from $307.00 / night

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(2)

1 / 33

Turtle Cove Villa - 10.4 miles away

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

$700.00

Excellent (2 reviews)

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from $700.00 / night

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(2)

1 / 35

The Bight Settlement Villa - 5.1 miles away

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

$643.00

Excellent (2 reviews)

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from $643.00 / night

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(8)

1 / 18

Turtle Cove Villa - 9.8 miles away

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

$514.00

Excellent (8 reviews)

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from $514.00 / night

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(25)

1 / 70

Long Bay Beach Villa - 3.1 miles away

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

$1,557.00

Excellent (25 reviews)

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from $1,557.00 / night

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(1)

1 / 34

Long Bay Beach Villa - 3.4 miles away

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

$1,857.00

Very Good (1 reviews)

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from $1,857.00 / night

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1 / 50

Five Cays Settlement Villa - 2.1 miles away

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

$1,700.00

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from $1,700.00 / night

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(4)

1 / 16

The Bight Settlement Villa - 5.2 miles away

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

$530.00

Excellent (4 reviews)

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from $530.00 / night

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(1)

1 / 66

The Bight Settlement Villa - 5 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$3,972.00

Excellent (1 reviews)

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from $3,972.00 / night

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(23)

1 / 23

The Bight Settlement Villa - 5 miles away

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

$757.00

Excellent (23 reviews)

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from $757.00 / night

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1 / 22

The Bight Settlement House - 5.1 miles away

  • 2
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$971.00

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from $971.00 / 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

$1,357.00

Very Good (2 reviews)

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from $1,357.00 / night

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(1)

1 / 42

Turtle Cove House - 6.1 miles away

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

$1,029.00

Excellent (1 reviews)

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from $1,029.00 / night

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(1)

1 / 21

Long Bay Beach Villa - 3.3 miles away

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

$1,114.00

Very Good (1 reviews)

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from $1,114.00 / night

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(12)

1 / 43

The Bight Settlement House - 5.7 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2,222.00

Excellent (12 reviews)

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from $2,222.00 / night

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(5)

1 / 18

The Bight Settlement Cottage - 5.3 miles away

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

$519.00

Excellent (5 reviews)

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from $519.00 / night

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