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Holiday Homes in Leeward

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90 rentals in Leeward.
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Villa Kendara~$995Aug/Sep~Private, Pristine Guesthouse~Panoramic SeaFront Luxury, holiday rental in Leeward
Villa Kendara~$995Aug/Sep~Private, Pristine Guesthouse~Panoramic SeaFront Luxury, holiday rental in Leeward
Villa Kendara~$995Aug/Sep~Private, Pristine Guesthouse~Panoramic SeaFront Luxury, holiday rental in Leeward

Villa Kendara~$995Aug/Sep~Private, Pristine Guesthouse~Panoramic SeaFront Luxury

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fantastic family villa, sleeps 8-10, 4 bedrooms, 2 pool, BBQ Pit, outdoor cabana, holiday rental in Leeward
Fantastic family villa, sleeps 8-10, 4 bedrooms, 2 pool, BBQ Pit, outdoor cabana, holiday rental in Leeward
Fantastic family villa, sleeps 8-10, 4 bedrooms, 2 pool, BBQ Pit, outdoor cabana, holiday rental in Leeward

Fantastic family villa, sleeps 8-10, 4 bedrooms, 2 pool, BBQ Pit, outdoor cabana

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Villa Tropica | Luxury Villa Near Beach, Lush Garden, Chromatic Private Pool, holiday rental in Leeward
Villa Tropica | Luxury Villa Near Beach, Lush Garden, Chromatic Private Pool, holiday rental in Leeward
Villa Tropica | Luxury Villa Near Beach, Lush Garden, Chromatic Private Pool, holiday rental in Leeward

Villa Tropica | Luxury Villa Near Beach, Lush Garden, Chromatic Private Pool

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Villa Vivace - Brand New Luxurious Waterfront Home, holiday rental in Leeward
Villa Vivace - Brand New Luxurious Waterfront Home, holiday rental in Leeward
Villa Vivace - Brand New Luxurious Waterfront Home, holiday rental in Leeward

Villa Vivace - Brand New Luxurious Waterfront Home

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Seclusion, Privacy, Luxury - This is the perfect place for 2 people., holiday rental in Leeward
Seclusion, Privacy, Luxury - This is the perfect place for 2 people., holiday rental in Leeward
Seclusion, Privacy, Luxury - This is the perfect place for 2 people., holiday rental in Leeward

Seclusion, Privacy, Luxury - This is the perfect place for 2 people.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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***Kick Back and Relax Tiki Style!!!***, holiday rental in Leeward
***Kick Back and Relax Tiki Style!!!***, holiday rental in Leeward
***Kick Back and Relax Tiki Style!!!***, holiday rental in Leeward

***Kick Back and Relax Tiki Style!!!***

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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** RAVE REVIEWS- Family Friendly Ocean Front 3 Bedroom, 3 Bath Villa, holiday rental in Leeward
** RAVE REVIEWS- Family Friendly Ocean Front 3 Bedroom, 3 Bath Villa, holiday rental in Leeward
** RAVE REVIEWS- Family Friendly Ocean Front 3 Bedroom, 3 Bath Villa, holiday rental in Leeward

** RAVE REVIEWS- Family Friendly Ocean Front 3 Bedroom, 3 Bath Villa

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Villa Cariad, beautiful pool, luxury for 8, kayaks, SUPs on Leeward Canal!!, holiday rental in Leeward
Villa Cariad, beautiful pool, luxury for 8, kayaks, SUPs on Leeward Canal!!, holiday rental in Leeward
Villa Cariad, beautiful pool, luxury for 8, kayaks, SUPs on Leeward Canal!!, holiday rental in Leeward

Villa Cariad, beautiful pool, luxury for 8, kayaks, SUPs on Leeward Canal!!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Beach House 2 on Kite Boarding Beach. Silver Palms Cottage #2, holiday rental in Leeward
Cozy Beach House 2 on Kite Boarding Beach. Silver Palms Cottage #2, holiday rental in Leeward
Cozy Beach House 2 on Kite Boarding Beach. Silver Palms Cottage #2, holiday rental in Leeward

Cozy Beach House 2 on Kite Boarding Beach. Silver Palms Cottage #2

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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2 Bedroom Villa With 360 Degree Views Set High On Hill On 5 Acre Estate., holiday rental in Leeward
2 Bedroom Villa With 360 Degree Views Set High On Hill On 5 Acre Estate., holiday rental in Leeward
2 Bedroom Villa With 360 Degree Views Set High On Hill On 5 Acre Estate., holiday rental in Leeward

2 Bedroom Villa With 360 Degree Views Set High On Hill On 5 Acre Estate.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Captivating and breathtaking villa with 360 degree view overlooking the ocean, holiday rental in Leeward
Captivating and breathtaking villa with 360 degree view overlooking the ocean, holiday rental in Leeward
Captivating and breathtaking villa with 360 degree view overlooking the ocean, holiday rental in Leeward

Captivating and breathtaking villa with 360 degree view overlooking the ocean

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Providenciales Resort Style Villa close to beaches Flexible cancellation policy, holiday rental in Leeward
Providenciales Resort Style Villa close to beaches Flexible cancellation policy, holiday rental in Leeward
Providenciales Resort Style Villa close to beaches Flexible cancellation policy, holiday rental in Leeward

Providenciales Resort Style Villa close to beaches Flexible cancellation policy

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A colourful, Caribbean retreat, a short walk to stunning Pelican Beach, holiday rental in Leeward
A colourful, Caribbean retreat, a short walk to stunning Pelican Beach, holiday rental in Leeward
A colourful, Caribbean retreat, a short walk to stunning Pelican Beach, holiday rental in Leeward

A colourful, Caribbean retreat, a short walk to stunning Pelican Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Moringa Villa, holiday rental in Leeward
Moringa Villa, holiday rental in Leeward
Moringa Villa, holiday rental in Leeward

Moringa Villa

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay., holiday rental in Leeward
Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay., holiday rental in Leeward
Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay., holiday rental in Leeward

Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Oceanfront. Newly renovated 4 bed, private pool, water access. Holiday dream!, holiday rental in Leeward
Oceanfront. Newly renovated 4 bed, private pool, water access. Holiday dream!, holiday rental in Leeward
Oceanfront. Newly renovated 4 bed, private pool, water access. Holiday dream!, holiday rental in Leeward

Oceanfront. Newly renovated 4 bed, private pool, water access. Holiday dream!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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☀️New Leeward Jewel Luxury Villa!☀️, holiday rental in Leeward
☀️New Leeward Jewel Luxury Villa!☀️, holiday rental in Leeward
☀️New Leeward Jewel Luxury Villa!☀️, holiday rental in Leeward

☀️New Leeward Jewel Luxury Villa!☀️

Holiday Rental House
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Brand New Waterfront Luxury Villa With Views!!, holiday rental in Leeward
Brand New Waterfront Luxury Villa With Views!!, holiday rental in Leeward
Brand New Waterfront Luxury Villa With Views!!, holiday rental in Leeward

Brand New Waterfront Luxury Villa With Views!!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER, holiday rental in Leeward
LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER, holiday rental in Leeward
LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER, holiday rental in Leeward

LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Pelican Cottage - Minutes to Grace Bay Beach!!Bikes Incuded!!/Car 4 Rent!!, holiday rental in Leeward
Pelican Cottage - Minutes to Grace Bay Beach!!Bikes Incuded!!/Car 4 Rent!!, holiday rental in Leeward
Pelican Cottage - Minutes to Grace Bay Beach!!Bikes Incuded!!/Car 4 Rent!!, holiday rental in Leeward

Pelican Cottage - Minutes to Grace Bay Beach!!Bikes Incuded!!/Car 4 Rent!!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Oasis with Pool, holiday rental in Leeward
Private Oasis with Pool, holiday rental in Leeward
Private Oasis with Pool, holiday rental in Leeward

Private Oasis with Pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Picture Perfect 5 Bed Villa in Grace Bay.  ⭐️ Gated enclave ⭐️ Golf cart Leeward, holiday rental in Leeward
Picture Perfect 5 Bed Villa in Grace Bay.  ⭐️ Gated enclave ⭐️ Golf cart Leeward, holiday rental in Leeward
Picture Perfect 5 Bed Villa in Grace Bay.  ⭐️ Gated enclave ⭐️ Golf cart Leeward, holiday rental in Leeward

Picture Perfect 5 Bed Villa in Grace Bay. ⭐️ Gated enclave ⭐️ Golf cart Leeward

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Pelican Vista: 150 yards from incredible Grace Bay Beach!, holiday rental in Leeward
Pelican Vista: 150 yards from incredible Grace Bay Beach!, holiday rental in Leeward
Pelican Vista: 150 yards from incredible Grace Bay Beach!, holiday rental in Leeward

Pelican Vista: 150 yards from incredible Grace Bay Beach!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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PERIWINKLE | Charming Caribbean Home | Steps to the World's Best Beach, holiday rental in Leeward
PERIWINKLE | Charming Caribbean Home | Steps to the World's Best Beach, holiday rental in Leeward
PERIWINKLE | Charming Caribbean Home | Steps to the World's Best Beach, holiday rental in Leeward

PERIWINKLE | Charming Caribbean Home | Steps to the World's Best Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area, holiday rental in Leeward
WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area, holiday rental in Leeward
WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area, holiday rental in Leeward

WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury villa in gated enclave. ⭐️ Steps to Grace Bay Beach ⭐️ Golf cart. Leeward, holiday rental in Leeward
Luxury villa in gated enclave. ⭐️ Steps to Grace Bay Beach ⭐️ Golf cart. Leeward, holiday rental in Leeward
Luxury villa in gated enclave. ⭐️ Steps to Grace Bay Beach ⭐️ Golf cart. Leeward, holiday rental in Leeward

Luxury villa in gated enclave. ⭐️ Steps to Grace Bay Beach ⭐️ Golf cart. Leeward

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Moringa 5 BR Villa - Canal Front, holiday rental in Leeward
Moringa 5 BR Villa - Canal Front, holiday rental in Leeward
Moringa 5 BR Villa - Canal Front, holiday rental in Leeward

Moringa 5 BR Villa - Canal Front

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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The Caicos House -5 mins to the Beach  & Dining!, holiday rental in Leeward
The Caicos House -5 mins to the Beach  & Dining!, holiday rental in Leeward
The Caicos House -5 mins to the Beach  & Dining!, holiday rental in Leeward

The Caicos House -5 mins to the Beach & Dining!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy & Chic | Grace Bay Beach | Pets Welcome!, holiday rental in Leeward
Cozy & Chic | Grace Bay Beach | Pets Welcome!, holiday rental in Leeward
Cozy & Chic | Grace Bay Beach | Pets Welcome!, holiday rental in Leeward

Cozy & Chic | Grace Bay Beach | Pets Welcome!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Dream 5 BR Aqua, holiday rental in Leeward
Ocean Dream 5 BR Aqua, holiday rental in Leeward
Ocean Dream 5 BR Aqua, holiday rental in Leeward

Ocean Dream 5 BR Aqua

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Khaya | Newly Built Luxury Waterfront Villa, holiday rental in Leeward
Khaya | Newly Built Luxury Waterfront Villa, holiday rental in Leeward
Khaya | Newly Built Luxury Waterfront Villa, holiday rental in Leeward

Khaya | Newly Built Luxury Waterfront Villa

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Dream 5 BR Villa Azur - Oceanfront, holiday rental in Leeward
Ocean Dream 5 BR Villa Azur - Oceanfront, holiday rental in Leeward
Ocean Dream 5 BR Villa Azur - Oceanfront, holiday rental in Leeward

Ocean Dream 5 BR Villa Azur - Oceanfront

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated 5 Bedroom 5 Bath Villa Spectacular Views Ocean, Beaches close!!!, holiday rental in Leeward
Newly Renovated 5 Bedroom 5 Bath Villa Spectacular Views Ocean, Beaches close!!!, holiday rental in Leeward
Newly Renovated 5 Bedroom 5 Bath Villa Spectacular Views Ocean, Beaches close!!!, holiday rental in Leeward

Newly Renovated 5 Bedroom 5 Bath Villa Spectacular Views Ocean, Beaches close!!!

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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2 bed villa - Closest villa to the ocean on island!, holiday rental in Leeward
2 bed villa - Closest villa to the ocean on island!, holiday rental in Leeward
2 bed villa - Closest villa to the ocean on island!, holiday rental in Leeward

2 bed villa - Closest villa to the ocean on island!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Dream 5 BR Villa Aqua - Oceanfront, holiday rental in Leeward
Ocean Dream 5 BR Villa Aqua - Oceanfront, holiday rental in Leeward
Ocean Dream 5 BR Villa Aqua - Oceanfront, holiday rental in Leeward

Ocean Dream 5 BR Villa Aqua - Oceanfront

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda, holiday rental in Leeward
Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda, holiday rental in Leeward
Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda, holiday rental in Leeward

Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Cozy House, 3 bedroom house, near #1 Grace Bay Beach, Turks and Caicos, holiday rental in Leeward
The Cozy House, 3 bedroom house, near #1 Grace Bay Beach, Turks and Caicos, holiday rental in Leeward
The Cozy House, 3 bedroom house, near #1 Grace Bay Beach, Turks and Caicos, holiday rental in Leeward

The Cozy House, 3 bedroom house, near #1 Grace Bay Beach, Turks and Caicos

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Salt Air Villa, holiday rental in Leeward
Salt Air Villa, holiday rental in Leeward
Salt Air Villa, holiday rental in Leeward

Salt Air Villa

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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*FOOTPRINTS ON GRACE BAY*  OCEAN FRONT VILLA, INCL CHEF, BUTLER, DAILY CLEANING, holiday rental in Leeward
*FOOTPRINTS ON GRACE BAY*  OCEAN FRONT VILLA, INCL CHEF, BUTLER, DAILY CLEANING, holiday rental in Leeward
*FOOTPRINTS ON GRACE BAY*  OCEAN FRONT VILLA, INCL CHEF, BUTLER, DAILY CLEANING, holiday rental in Leeward

*FOOTPRINTS ON GRACE BAY* OCEAN FRONT VILLA, INCL CHEF, BUTLER, DAILY CLEANING

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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55 Oasis Villa  (Make it your Home), holiday rental in Leeward
55 Oasis Villa  (Make it your Home), holiday rental in Leeward
55 Oasis Villa  (Make it your Home), holiday rental in Leeward

55 Oasis Villa (Make it your Home)

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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AMAZING GRACE VILLA - Amazing 5 Bedroom Luxury Beach Front Villa on Grace Bay Be, holiday rental in Leeward
AMAZING GRACE VILLA - Amazing 5 Bedroom Luxury Beach Front Villa on Grace Bay Be, holiday rental in Leeward
AMAZING GRACE VILLA - Amazing 5 Bedroom Luxury Beach Front Villa on Grace Bay Be, holiday rental in Leeward

AMAZING GRACE VILLA - Amazing 5 Bedroom Luxury Beach Front Villa on Grace Bay Be

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Stunning Canal Front Villa, holiday rental in Leeward
Stunning Canal Front Villa, holiday rental in Leeward
Stunning Canal Front Villa, holiday rental in Leeward

Stunning Canal Front Villa

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Enjoy sunset on the large deck! ⭐️NEW luxury villa in gated enclave.  ⭐️ Golf ca, holiday rental in Leeward
Enjoy sunset on the large deck! ⭐️NEW luxury villa in gated enclave.  ⭐️ Golf ca, holiday rental in Leeward
Enjoy sunset on the large deck! ⭐️NEW luxury villa in gated enclave.  ⭐️ Golf ca, holiday rental in Leeward

Enjoy sunset on the large deck! ⭐️NEW luxury villa in gated enclave. ⭐️ Golf ca

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!, holiday rental in Leeward
30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!, holiday rental in Leeward
30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!, holiday rental in Leeward

30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!, holiday rental in Leeward
Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!, holiday rental in Leeward
Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!, holiday rental in Leeward

Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Two bedroom with swimming pool, holiday rental in Leeward
Two bedroom with swimming pool, holiday rental in Leeward
Two bedroom with swimming pool, holiday rental in Leeward

Two bedroom with swimming pool

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom Condo in the heart of Grace Bay, holiday rental in Leeward
2 Bedroom Condo in the heart of Grace Bay, holiday rental in Leeward
2 Bedroom Condo in the heart of Grace Bay, holiday rental in Leeward

2 Bedroom Condo in the heart of Grace Bay

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Brand new nearly beachfront 4 bedroom villa, holiday rental in Leeward
Brand new nearly beachfront 4 bedroom villa, holiday rental in Leeward
Brand new nearly beachfront 4 bedroom villa, holiday rental in Leeward

Brand new nearly beachfront 4 bedroom villa

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Ocean Dream Studio Blue - Ocean View, holiday rental in Leeward
Ocean Dream Studio Blue - Ocean View, holiday rental in Leeward
Ocean Dream Studio Blue - Ocean View, holiday rental in Leeward

Ocean Dream Studio Blue - Ocean View

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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6 Bedroom Villa - Turks & Caicos, holiday rental in Leeward
6 Bedroom Villa - Turks & Caicos, holiday rental in Leeward
6 Bedroom Villa - Turks & Caicos, holiday rental in Leeward

6 Bedroom Villa - Turks & Caicos

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Frequently Asked Questions about Leeward