Search 105,200+ Vacation Rentals

Leeward Vacation Rentals & Homes with Swimming Pool - 4 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

4 Vacation rentals

Filters applied: Swimming pool

1 / 16

Leeward Villa

  • 6
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1857

Inquire

from $1857 / night

1 / 15

Leeward Villa

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

$1250

Inquire

from $1250 / night

1 / 24

Leeward House

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

from $357 / night

1 / 53

Leeward Villa

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

$9681

Inquire

from $9681 / night

Your search has been expanded 5.3 miles to include more rentals

1 / 16

Grace Bay Villa - 0.1 miles away

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

$393

Book

from $393 / night

1 / 19

Providenciales Cottage - 0.1 miles away

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

$300

Book

from $300 / night

1 / 24

Grace Bay Villa - 0.1 miles away

  • 8
  • 16
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$16139

Inquire

from $16139 / night

1 / 41

Grace Bay Villa - 0.1 miles away

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

$2900

Inquire

from $2900 / night

1 / 11

Grace Bay Villa - 0.1 miles away

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

$2609

Inquire

from $2609 / night

1 / 49

Grace Bay Villa - 0.1 miles away

  • 6
  • 12
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

$7531

Inquire

from $7531 / night

(1)

1 / 37

Grace Bay Villa - 0.1 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$600

Excellent (1 reviews)

Book

from $600 / night

1 / 37

Grace Bay Villa - 0.1 miles away

  • 8
  • 16
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$11125

Inquire

from $11125 / night

(6)

1 / 28

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

$1550

Excellent (6 reviews)

Inquire

from $1550 / night

1 / 25

Grace Bay Villa - 0.1 miles away

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

$2609

Inquire

from $2609 / night

(2)

1 / 43

Grace Bay Villa - 0.1 miles away

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

$1050

Excellent (2 reviews)

Inquire

from $1050 / night

1 / 13

Grace Bay Villa - 0.1 miles away

  • 2
  • 4
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$1717

Inquire

from $1717 / night

(3)

1 / 19

Grace Bay Villa - 0.1 miles away

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

$971

Excellent (3 reviews)

Inquire

from $971 / night

1 / 18

Grace Bay Villa - 0.1 miles away

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

$5326

Inquire

from $5326 / night

1 / 19

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children

$4950

Inquire

from $4950 / night

1 / 26

Long Bay Beach Villa - 2.4 miles away

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

$1506

Inquire

from $1506 / night

(1)

1 / 33

Providenciales Villa - 2.6 miles away

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

$1557

Very Good (1 reviews)

Inquire

from $1557 / night

1 / 20

Long Bay Beach Villa - 3.1 miles away

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$2000

Inquire

from $2000 / night

1 / 23

Long Bay Beach Villa - 3.1 miles away

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$2700

Inquire

from $2700 / night

1 / 16

Providenciales Villa - 3.2 miles away

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

from $700 / night

(1)

1 / 23

Long Bay Beach Villa - 3.3 miles away

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

$985

Very Good (1 reviews)

Inquire

from $985 / night

(11)

1 / 38

Long Bay Beach Villa - 3.4 miles away

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

$1414

Excellent (11 reviews)

Inquire

from $1414 / night

1 / 30

Providenciales Villa - 3.5 miles away

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

$1642

Inquire

from $1642 / night

(14)

1 / 31

Turtle Cove Villa - 4.9 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$369

Very Good (14 reviews)

Inquire

from $369 / night

(2)

1 / 24

Providenciales Villa - 4.9 miles away

  • 3
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$785

Excellent (2 reviews)

Inquire

from $785 / night

(1)

1 / 31

Providenciales Villa - 5 miles away

  • 3
  • 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$714

Excellent (1 reviews)

Inquire

from $714 / night

(4)

1 / 20

Providenciales Villa - 5 miles away

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

$589

Excellent (4 reviews)

Inquire

from $589 / night

(3)

1 / 22

Turtle Cove Condo - 5 miles away

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

$150

Very Good (3 reviews)

Book

from $150 / night

1 / 24

Providenciales Villa - 5 miles away

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

$1464

Inquire

from $1464 / night

1 / 24

Providenciales Villa - 5.1 miles away

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

$1471

Inquire

from $1471 / night

1 / 19

Providenciales Villa - 5.1 miles away

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

from $693 / night

1 / 20

Grace Bay Villa - 5.1 miles away

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

$514

Book

from $514 / night

(1)

1 / 22

Providenciales Villa - 5.1 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$758

Excellent (1 reviews)

Inquire

from $758 / night

(2)

1 / 16

Providenciales Villa - 5.1 miles away

  • 1
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$265

Excellent (2 reviews)

Inquire

from $265 / night

(4)

1 / 21

Providenciales Cottage - 5.2 miles away

  • 1
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$265

Excellent (4 reviews)

Inquire

from $265 / night

1 / 21

Providenciales Cottage - 5.2 miles away

  • 1
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $265 / night

1 / 25

Providenciales Villa - 5.2 miles away

  • 6
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1499

Inquire

from $1499 / night

(2)

1 / 15

Providenciales Villa - 5.2 miles away

  • 1
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$425

Excellent (2 reviews)

Inquire

from $425 / night

(5)

1 / 15

Providenciales Villa - 5.2 miles away

  • 1
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$425

Excellent (5 reviews)

Inquire

from $425 / night

(3)

1 / 29

Providenciales Villa - 5.3 miles away

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

$1128

Excellent (3 reviews)

Inquire

from $1128 / night