15 Best Vacation Rentals in Leeward - Holiday Lettings - Cabins

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15 Vacation rentals

13

Vacation cottage in Leeward

Providenciales / Leeward

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 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 $138 / night

$898 / week

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from $138 / 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
Rafters 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 access. Fr …see more

from $2500 / night

$17500 / week

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from $2500 / night

35

Vacation villa in Leeward

Providenciales / Leeward

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • 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 $1880 / night

$13160 / week

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from $1880 / 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 $1042 / night

$7294 / week

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from $1042 / 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, and nearly as much living space outdoors as i …see more

from $5750 / night

$40250 / week

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from $5750 / 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, and nearly as much living space outdoors as i …see more

from $5750 / night

$40250 / week

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from $5750 / night

21

Villa rental in Leeward with swimming pool

Providenciales / Leeward

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A secluded Mediterranean Villa in the heart of Turtle Tail named after the European town located on the northwestern coast of Sicily. Constant upgrades including all new outside furniture by Restoration Hardware, all new lounge and dining furniture, new beds and an i …see more

from $1000 / night

$7000 - $11000 / week

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from $1000 / night

10

Villa rental in Leeward with swimming pool

Providenciales / Leeward

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Discover an authentic island escape at Villa Tropidero. Villa Tropidero offers one large master suite and two junior suites to accommodate up to six guests; all suites include separate air conditioning, ceiling fans, private veranda access, DVD/CD players, a televisi …see more

from $1072 / night

$7500 - $9500 / week

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from $1072 / night

(1) Excellent 

17

Leeward Vacation villa rental

Providenciales / Leeward

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • 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 $500 / night

$3500 / week

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from $500 / night

16

Vacation villa in Leeward

Providenciales / Leeward

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Lighten your soul and feel your cares melt away the moment you step through the doorway at Villa de Ligera (villa of light). This spacious designer villa is located on unspoiled Turtle Tail, overlooking the sparkling waters of the Caribbean Sea and has a private walled …see more

from $1428 / night

$10000 - $14000 / week

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from $1428 / night

23

Vacation home with swimming pool in Leeward

Providenciales / Leeward

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • 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, origin …see more

from $357 / night

$2499 - $6999 / week

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from $357 / 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, and nearly as much living space outdoors as i …see more

from $5750 / night

$40250 / week

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from $5750 / night

25

Villa accommodation in Leeward

Providenciales / Leeward

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Designed by the acclaimed architect, Ron Shaw, this Turks and Caicos luxury villa provides world-class contemporary design with a stunning designer-furnished interior. Engulf the senses in an awe-inspiring space filled with an abundance of polished glass and steel, fuse …see more

from $2000 / night

$14000 - $35000 / week

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from $2000 / night

44

Vacation home with swimming pool in Leeward

Providenciales / Leeward

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Swimming pool
  • 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 $10000 / night

$70000 / week

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from $10000 / 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 House Turks & Caicos. Turks & Caicos is known for its luxury properties and exclusive destinations, and though there are many premium accommodations, the Villa Turtle House rates as one of the rare "ultra-premium" settings. Set in Turtle Tail, it is immense …see more

from $10000 / night

$70000 - $140000 / week

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from $10000 / night

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