COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Search 105,200+ Vacation Rentals
✕

Leeward Vacation Rentals & Homes - 85 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

85 Vacation rentals

1 / 37

Leeward Villa

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

Responds fast! Avg. 1 hour 26 minutes

$1,088.00

Book

from $1,088.00 / night

Book
1 / 12

Leeward Villa

  • 3
  • 6
  • 5 nights min
  • Child friendly

Responds fast! Avg. 1 hour 25 minutes

$630.00

Book

from $630.00 / night

Book
1 / 25

Leeward Villa

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

$1,300.00

Book

from $1,300.00 / night

Book
1 / 36

Leeward Villa

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

$8,250.00

Inquire

from $8,250.00 / night

Inquire
1 / 18

Leeward Villa

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

$7,150.00

Inquire

from $7,150.00 / night

Inquire

(1)

1 / 38

Leeward Villa

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

$7,590.00

Excellent (1 reviews)

Inquire

from $7,590.00 / night

Inquire
1 / 25

Leeward Villa

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

$1,430.00

Inquire

from $1,430.00 / night

Inquire
1 / 19

Leeward Villa

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

$2,668.00

Inquire

from $2,668.00 / night

Inquire
1 / 36

Leeward Villa

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

$12,540.00

Inquire

from $12,540.00 / night

Inquire
1 / 36

Leeward Villa

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

$10,120.00

Inquire

from $10,120.00 / night

Inquire

Your search has been expanded 11 miles to include more rentals

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

Book

from $458.00 / night

Book

(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)

Book

from $258.00 / night

Book

(19)

1 / 41

Turtle Cove Villa - 4.9 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

$429.00

Very Good (19 reviews)

Inquire

from $429.00 / night

Inquire
1 / 19

Providenciales Apartment - 11 miles away

  • 2
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Air conditioning

Responds fast! Avg. 2 hours 59 minutes

$630.00

Book

from $630.00 / night

Book

(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 59 minutes

$401.00

Average (2 reviews)

Book

from $401.00 / night

Book

(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 59 minutes

$745.00

Very Good (1 reviews)

Book

from $745.00 / night

Book
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 59 minutes

$687.00

Book

from $687.00 / night

Book
1 / 16

Turtle Cove Apartment - 11 miles away

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

Responds fast! Avg. 2 hours 59 minutes

$916.00

Book

from $916.00 / night

Book

(51)

1 / 42

Providenciales 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 (51 reviews)

Inquire

from $5,000.00 / night

Inquire

(15)

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

$400.00

Excellent (15 reviews)

Inquire

from $400.00 / night

Inquire

(4)

1 / 21

Providenciales Apartment - 11 miles away

  • 2
  • 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

Responds fast! Avg. 3 hours 24 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

$229.00

Excellent (4 reviews)

Book

from $229.00 / night

Book

(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

$1,963.00

Very Good (10 reviews)

Book

from $1,963.00 / night

Book

(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 46 minutes

$1,105.00

Excellent (1 reviews)

Book

from $1,105.00 / night

Book

(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 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

$974.00

Excellent (2 reviews)

Book

from $974.00 / night

Book

(6)

1 / 28

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Responds fast! Avg. 1 hour 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

$2,806.00

Excellent (6 reviews)

Book

from $2,806.00 / night

Book
1 / 17

Grace Bay Villa - 0.1 miles away

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

$5,445.00

Inquire

from $5,445.00 / night

Inquire
1 / 15

The Bight Settlement Villa - 5.3 miles away

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

$880.00

Inquire

from $880.00 / night

Inquire
1 / 17

The Bight Settlement Villa - 5.1 miles away

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

$565.00

Inquire

from $565.00 / night

Inquire
1 / 36

Grace Bay Villa - 0.1 miles away

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

$2,530.00

Inquire

from $2,530.00 / night

Inquire
1 / 39

Grace Bay Villa - 0.1 miles away

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

$7,590.00

Inquire

from $7,590.00 / night

Inquire
1 / 20

Grace Bay Villa - 0.1 miles away

  • 1
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$4,741.00

Inquire

from $4,741.00 / night

Inquire
1 / 20

Grace Bay Villa - 0.1 miles away

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

$5,445.00

Inquire

from $5,445.00 / night

Inquire
1 / 31

The Bight Settlement Villa - 5.1 miles away

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

$1,617.00

Inquire

from $1,617.00 / night

Inquire
1 / 29

Grace Bay Villa - 0.1 miles away

  • 5
  • 14
  • min stay varies
  • Child friendly

$5,500.00

Inquire

from $5,500.00 / night

Inquire
1 / 50

Grace Bay Villa - 0.1 miles away

  • 4
  • 10
  • min stay varies
  • Child friendly

$2,300.00

Inquire

from $2,300.00 / night

Inquire
1 / 19

Grace Bay Villa - 0.1 miles away

  • 5
  • 10
  • min stay varies
  • Child friendly

$5,500.00

Inquire

from $5,500.00 / night

Inquire

(1)

1 / 10

Grace Bay Villa - 0.1 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly

$1,450.00

Excellent (1 reviews)

Inquire

from $1,450.00 / night

Inquire
1 / 29

Grace Bay Villa - 0.1 miles away

  • 6
  • 12
  • min stay varies
  • Child friendly

$6,900.00

Inquire

from $6,900.00 / night

Inquire

(17)

Certificate of Excellence

1 / 42

Grace Bay Villa - 0.1 miles away

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

Responds fast! Avg. 1 hour 46 minutes

Travelers’ Choice award

$1,023.00

Excellent (17 reviews)

Book

from $1,023.00 / night

Book
1 / 37

Grace Bay Villa - 0.1 miles away

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

$10,850.00

Book

from $10,850.00 / night

Book