25 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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359 Vacation rentals

13

Vacation cottage in Leeward

Providenciales / Leeward

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
This charismatic island studio cottage is approximately 550 sq. ft. (450 sq. ft. indoor and 100 sq. ft. outdoor space), newly renovated and tastefully furnished with an island feel, accented with sky scraper coconut trees and singing birds. Our cottage is modern, fully …see more

from $135 / night

$945 / week

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from $135 / night

(1) Excellent 

20

Vacation home in Leeward

Providenciales / Leeward

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Welcome to a Caribbean dream. The three charming bungalows of The Retreat are 190 paces down a manicured path to Grace Bay Beach Tucked into the serenity of 25 year old gardens, come relax and feel the magical serenity of this well loved property. The main house, orig …see more

from $500 / night

$3,500 - $7,000 / week

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from $500 / night

(1) Excellent 

17

Leeward Vacation villa rental

Providenciales / Leeward

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Welcome to Caicos Dream Villa, Turks and Caicos Islands!! This villa is brand new and located 1 minute from the worlds number one beach Grace Bay of Turks and Caicos Islands. Villa is a modern contemporary master piece complete with two King Master en suites, modern kit …see more

from $475 / night

$3,500 / week

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avg. 3 hours 1 minutes

from $475 / night

13

Vacation villa in Leeward

Providenciales / Leeward

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
With stunning views of the Turks and Caicos Banks, a unique modern layout and exotic accents, villa Balinese is an unforgettable retreat. Located on Ocean Drive on Providenciales and laid out around a private infinity pool, the spacious three-bedroom villa pairs strikin …see more

from $1,042 / night

$7,294 / week

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avg. 15 minutes

from $1,042 / night

23

Vacation villa with shared pool in Leeward

Providenciales / Leeward

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Less than 600 miles southeast of Miami, the idyllic Turks and Caicos Islands beckon sophisticated travelers. Here on the sugar-sand shores of Providenciales, outlined in azure blue, the simple pleasures of island living mesh seamlessly with contemporary luxuries in a Ca …see more

from $2,500 / night

$17,500 - $23,100 / week

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avg. 22 minutes

from $2,500 / night

(1) Excellent 

35

Leeward Vacation villa rental

Providenciales / Leeward

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Bajacu ("rising sun" ) is located on the beautiful island of Providenciales, Turks and Caicos. It is situated on a south shore hilltop with a breathtaking 270 degree view of the sea, surrounded by a 13 acre estate of lush tropical gardens with coconut, royal palm, fruit …see more

from $3,000 / night

$21,000 - $84,000 / week

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avg. 22 minutes

from $3,000 / night

23

Vacation villa with shared pool in Leeward

Providenciales / Leeward

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Less than 600 miles southeast of Miami, the idyllic Turks and Caicos Islands beckon sophisticated travelers. Here on the sugar-sand shores of Providenciales, outlined in azure blue, the simple pleasures of island living mesh seamlessly with contemporary luxuries in a Ca …see more

from $1,875 / night

$13,125 / week

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avg. 22 minutes

from $1,875 / night

23

Vacation villa with shared pool in Leeward

Providenciales / Leeward

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Less than 600 miles southeast of Miami, the idyllic Turks and Caicos Islands beckon sophisticated travelers. Here on the sugar-sand shores of Providenciales, outlined in azure blue, the simple pleasures of island living mesh seamlessly with contemporary luxuries in a Ca …see more

from $1,250 / night

$8,750 - $11,200 / week

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avg. 22 minutes

from $1,250 / night

32

Leeward Vacation villa rental

Providenciales / Leeward

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
Spend the vacation of a lifetime at villa Bajacu. Its bright coral walls are unforgettable, but the ocean views from its hilltop location on the island of Providenciales are even more memorable. With six bedrooms, two pools, a private beach and nearly as much living spa …see more

from $3,000 / night

$21,000 / week

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avg. 15 minutes

from $3,000 / night

53

Vacation villa with swimming pool in Leeward

Providenciales / Leeward

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set on a private cove on the south side of the island far from wandering tourists, Turtle House is an estate in the truest sense of the word, an oasis of calm and represents the best the Turks & Caicos has to offer. A mix of Asian design, modern elegance, and Caribbean …see more

from $10,135 / night

$70,942 / week

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from $10,135 / night

32

Leeward Vacation villa rental

Providenciales / Leeward

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
Spend the vacation of a lifetime at villa Bajacu. Its bright coral walls are unforgettable, but the ocean views from its hilltop location on the island of Providenciales are even more memorable. With six bedrooms, two pools, a private beach and nearly as much living spa …see more

from $3,000 / night

$21,000 / week

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avg. 15 minutes

from $3,000 / night

24

Vacation villa in Leeward

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Adam & Eve is a palatial luxury villa in the Leeward Settlement on the beautiful island of Providenciales in Turks and Caicos. With waterfront property along a swimmable canal, the four-bedroom vacation rental features outstanding outdoor and indoor spaces for relaxing …see more

from $850 / night

$5,950 / week

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avg. 15 minutes

from $850 / night

35

Vacation villa in Leeward

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Located in the fabulous Grace Bay area of the Turks and Caicos, Villa Islander comes together in a symphony of cool greys and copious natural wood. Just a two minute walk from the white sands at Coral Garden Beach, which is part of Princess Alexandra National Park, this …see more

from $1,480 / night

$10,360 / week

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avg. 15 minutes

from $1,480 / night

28

Vacation villa rental

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
A location close to the number-one beach in the world, eight hours of butler service each day and four suite-style bedrooms: it all adds up to a gorgeous luxury holiday at Turquoise Villa. This beautiful Leeward vacation rental is perfect for parties of up to eight, whe …see more

from $1,300 / night

$9,100 / week

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avg. 15 minutes

from $1,300 / night

38

Leeward Vacation villa rental

Providenciales / Leeward

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 8 Bedroom Villa can be rented as a 5 or 6 Bedroom Villa at special rates! This villa is an 8 bedroom Caribbean estate home spread across a number of separate buildings throughout the 5+ acre site. It can also be combined with the 2 bedroom Beach House property next …see more

from $10,600 / night

$74,200 / week

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from $10,600 / night

(1) Excellent 

40

Vacation villa in Leeward

Providenciales / Leeward

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Villa Turtle Tail Estate, Turks & Caicos. Turks & Caicos is known for its luxury properties and exclusive destinations, and though there are many premium accommodations, the Villa Turtle Tail Estate rates as one of the rare "ultra-premium" settings. Set in Turtle Tail, …see more

from $9,000 / night

$63,000 - $140,000 / week

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from $9,000 / night

(6) Very Good 

27

Villa rental in Leeward

Providenciales / Leeward

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Ask about children
  • Ask about pets
Emerald Villa is situated in a quiet cul-de-sac within the exclusive development of Old Leeward, directly opposite the Parrot Cay Landing. The villa is situated on a fully landscaped one acre lot facing the canal with a pool, large deck and an 80 ft. dock with ramp acce …see more

from $2,000 / night

$14,000 / week

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avg. 15 minutes

from $2,000 / night

11

Leeward Vacation villa rental

Providenciales / Leeward

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Hawksbill Beach House is located on the most pristine section of Grace Bay Beach in the luxurious residential community of Leeward. Design Features: Hawksbill Beach House on Grace Bay is everything you would imagine a beach house to be. This newly refurbished, spacious …see more

from $1,600 / night

$11,200 / week

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from $1,600 / night

32

Leeward Vacation villa rental

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Spend the vacation of a lifetime at villa Bajacu. Its bright coral walls are unforgettable, but the ocean views from its hilltop location on the island of Providenciales are even more memorable. With six bedrooms, two pools, a private beach and nearly as much living spa …see more

from $5,750 / night

$40,250 / week

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avg. 15 minutes

from $5,750 / night

44

Vacation home in Leeward

Providenciales / Leeward

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Child friendly
  • Air conditioning
The modestly named Turtle House boasts a property that’s anything but. Set on a private cove on the south side of the island far from wandering tourists, Turtle House is an estate in the truest sense of the word, an oasis of calm and represents the best the Turks & Caic …see more

from $10,000 / night

$70,000 / week

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from $10,000 / night

38

Leeward Vacation villa rental

Providenciales / Leeward

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 8 Bedroom Villa can be rented as a 5 or 6 Bedroom Villa at special rates! This villa is an 8 bedroom Caribbean estate home spread across a number of separate buildings throughout the 5+ acre site. It can also be combined with the 2 bedroom Beach House property next …see more

from $8,600 / night

$60,200 / week

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from $8,600 / night

19

Leeward Vacation villa rental

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Milestone Villa is a recently refurbished beach front villa located on the world renowned Grace Bay Beach. You can enjoy long walks along the shoreline or dip in the ocean – just steps away. This villa features 4 bedrooms, large heated pool, covered al fresco dining b …see more

from $2,650 / night

$18,550 / week

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from $2,650 / night

26

Vacation villa in Leeward

Providenciales / Leeward

8 10 Min stay varies

  • 8 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Hawksbill is a private eight bedroom villa located in the coveted Grace Bay area of Turks and Caicos. This luxury estate home has been spread across a number of separate buildings and designed as a multigenerational retreat. Showcasing contemporary Caribbean design that …see more

from $6,800 / night

$47,600 / week

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avg. 15 minutes

from $6,800 / night

38

Leeward Vacation villa rental

Providenciales / Leeward

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 8 Bedroom Villa can be rented as a 5 or 6 Bedroom Villa at special rates! This villa is an 8 bedroom Caribbean estate home spread across a number of separate buildings throughout the 5+ acre site. It can also be combined with the 2 bedroom Beach House property next …see more

from $12,500 / night

$87,500 / week

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from $12,500 / night

26

Leeward Vacation villa rental

Providenciales / Leeward

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Hawksbill is a private eight bedroom villa located in the coveted Grace Bay area of Turks and Caicos. This luxury estate home has been spread across a number of separate buildings and designed as a multigenerational retreat. Showcasing contemporary Caribbean design that …see more

from $8,300 / night

$58,100 / week

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avg. 15 minutes

from $8,300 / night

26

Vacation villa in Leeward

Providenciales / Leeward

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Ask about pets
Hawksbill is a private eight bedroom villa located in the coveted Grace Bay area of Turks and Caicos. This luxury estate home has been spread across a number of separate buildings and designed as a multigenerational retreat. Showcasing contemporary Caribbean design that …see more

from $10,350 / night

$72,450 / week

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avg. 15 minutes

from $10,350 / night

25

Vacation villa with swimming pool in Leeward

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
A modern luxurious four bedroom villa only a stone’s throw from the number one beach in the world. Listen to music in the shaded outdoor lounge and dining area next to the heated pool and jacuzzi. Alternatively relax in the hammock grove or sit with a glass of wine arou …see more

from $1,390 / night

$9,730 / week

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from $1,390 / night

61

Villa rental in Leeward

Providenciales / Leeward

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Villa Viatu is a spectacular luxury villa on Providenciales in Turks and Caicos. Situated on the leeward side of the island's northeast coast, the villa is just steps from Pelican Bay Beach and enjoys spectacular views of the Caribbean Sea. Outstanding outdoor amenities …see more

from $3,800 / night

$26,600 / week

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avg. 15 minutes

from $3,800 / night