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Leeward Vacation Rentals

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Bedrooms

Bathrooms

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5 mi
186 rentals in Leeward.
Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach, vacation rental in Leeward
Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach, vacation rental in Leeward
Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach, vacation rental in Leeward

Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony, vacation rental in Leeward
Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony, vacation rental in Leeward
Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony, vacation rental in Leeward

Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!, vacation rental in Leeward
Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!, vacation rental in Leeward
Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!, vacation rental in Leeward

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ocean Dream 5 BR Aqua, vacation rental in Leeward
Ocean Dream 5 BR Aqua, vacation rental in Leeward
Ocean Dream 5 BR Aqua, vacation rental in Leeward

Ocean Dream 5 BR Aqua

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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BRAND NEW Aqueous - Sunset Beach Villas TCI , vacation rental in Leeward
BRAND NEW Aqueous - Sunset Beach Villas TCI , vacation rental in Leeward
BRAND NEW Aqueous - Sunset Beach Villas TCI , vacation rental in Leeward

BRAND NEW Aqueous - Sunset Beach Villas TCI

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Grace Haven - brand new villa in Leeward , vacation rental in Leeward
Grace Haven - brand new villa in Leeward , vacation rental in Leeward
Grace Haven - brand new villa in Leeward , vacation rental in Leeward

Grace Haven - brand new villa in Leeward

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Villa Vision Beach | Beach Front - Located in Stunning Leeward with Private Poo, vacation rental in Leeward
Villa Vision Beach | Beach Front - Located in Stunning Leeward with Private Poo, vacation rental in Leeward
Villa Vision Beach | Beach Front - Located in Stunning Leeward with Private Poo, vacation rental in Leeward

Villa Vision Beach | Beach Front - Located in Stunning Leeward with Private Poo

Rental Home
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps
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Two Bedroom  Pool Villa on the Water - Near Grace Bay Beach, Comp Kayaks, Bikes, vacation rental in Leeward
Two Bedroom  Pool Villa on the Water - Near Grace Bay Beach, Comp Kayaks, Bikes, vacation rental in Leeward
Two Bedroom  Pool Villa on the Water - Near Grace Bay Beach, Comp Kayaks, Bikes, vacation rental in Leeward

Two Bedroom Pool Villa on the Water - Near Grace Bay Beach, Comp Kayaks, Bikes

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Garden Cottage on the canal in Leeward, vacation rental in Leeward
Charming Garden Cottage on the canal in Leeward, vacation rental in Leeward
Charming Garden Cottage on the canal in Leeward, vacation rental in Leeward

Charming Garden Cottage on the canal in Leeward

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Contemporary Beachfront Villa w/Heated Pool, Beach Toys, & Staff Included, vacation rental in Leeward
Contemporary Beachfront Villa w/Heated Pool, Beach Toys, & Staff Included, vacation rental in Leeward
Contemporary Beachfront Villa w/Heated Pool, Beach Toys, & Staff Included, vacation rental in Leeward

Contemporary Beachfront Villa w/Heated Pool, Beach Toys, & Staff Included

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Kenai’s Place-Just 2mins away from Grace Bay Beach Master Suite, vacation rental in Leeward
Kenai’s Place-Just 2mins away from Grace Bay Beach Master Suite, vacation rental in Leeward
Kenai’s Place-Just 2mins away from Grace Bay Beach Master Suite, vacation rental in Leeward

Kenai’s Place-Just 2mins away from Grace Bay Beach Master Suite

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ideally Located in Grace Bay!, vacation rental in Leeward
Ideally Located in Grace Bay!, vacation rental in Leeward
Ideally Located in Grace Bay!, vacation rental in Leeward

Ideally Located in Grace Bay!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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A colourful, Caribbean retreat, a short walk to stunning Pelican Beach, Leeward., vacation rental in Leeward
A colourful, Caribbean retreat, a short walk to stunning Pelican Beach, Leeward., vacation rental in Leeward
A colourful, Caribbean retreat, a short walk to stunning Pelican Beach, Leeward., vacation rental in Leeward

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Breezy Villa Luxury villa, vacation rental in Leeward
Breezy Villa Luxury villa, vacation rental in Leeward
Breezy Villa Luxury villa, vacation rental in Leeward

Breezy Villa Luxury villa

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Villa Belle Vie - Upper East Side Estate #9, vacation rental in Leeward
Villa Belle Vie - Upper East Side Estate #9, vacation rental in Leeward
Villa Belle Vie - Upper East Side Estate #9, vacation rental in Leeward

Villa Belle Vie - Upper East Side Estate #9

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Affordable Vacation in Turks and Caicos, vacation rental in Leeward
Affordable Vacation in Turks and Caicos, vacation rental in Leeward
Affordable Vacation in Turks and Caicos, vacation rental in Leeward

Affordable Vacation in Turks and Caicos

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ideal Location in Grace Bay!, vacation rental in Leeward
Ideal Location in Grace Bay!, vacation rental in Leeward
Ideal Location in Grace Bay!, vacation rental in Leeward

Ideal Location in Grace Bay!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful contemporary style villa on the beach, vacation rental in Leeward
Beautiful contemporary style villa on the beach, vacation rental in Leeward
Beautiful contemporary style villa on the beach, vacation rental in Leeward

Beautiful contemporary style villa on the beach

Rental Home
8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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A Designer Villa Near Beach - Waterslide, Chess, BBQ, Tanning Shelf, Kayaks, vacation rental in Leeward
A Designer Villa Near Beach - Waterslide, Chess, BBQ, Tanning Shelf, Kayaks, vacation rental in Leeward
A Designer Villa Near Beach - Waterslide, Chess, BBQ, Tanning Shelf, Kayaks, vacation rental in Leeward

A Designer Villa Near Beach - Waterslide, Chess, BBQ, Tanning Shelf, Kayaks

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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New! Luxury 1Bed Large Condo - Moments from the Beach, vacation rental in Leeward
New! Luxury 1Bed Large Condo - Moments from the Beach, vacation rental in Leeward
New! Luxury 1Bed Large Condo - Moments from the Beach, vacation rental in Leeward

New! Luxury 1Bed Large Condo - Moments from the Beach

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Pelican's Nest #4 · Oceanview 3 Bed Villa, vacation rental in Leeward
Pelican's Nest #4 · Oceanview 3 Bed Villa, vacation rental in Leeward
Pelican's Nest #4 · Oceanview 3 Bed Villa, vacation rental in Leeward

Pelican's Nest #4 · Oceanview 3 Bed Villa

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak., vacation rental in Leeward
Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak., vacation rental in Leeward
Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak., vacation rental in Leeward

Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Leeward Jewel Villa | 5-7 Bedrooms | Waterfront Villa | 10 mins from beach, vacation rental in Leeward
Leeward Jewel Villa | 5-7 Bedrooms | Waterfront Villa | 10 mins from beach, vacation rental in Leeward
Leeward Jewel Villa | 5-7 Bedrooms | Waterfront Villa | 10 mins from beach, vacation rental in Leeward

Leeward Jewel Villa | 5-7 Bedrooms | Waterfront Villa | 10 mins from beach

Rental Home
7 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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Beautifully Appointed Oceanfront Condos!  Life Doesn't Get Any Better!, vacation rental in Leeward
Beautifully Appointed Oceanfront Condos!  Life Doesn't Get Any Better!, vacation rental in Leeward
Beautifully Appointed Oceanfront Condos!  Life Doesn't Get Any Better!, vacation rental in Leeward

Beautifully Appointed Oceanfront Condos! Life Doesn't Get Any Better!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Seagrace Villa Luxury villa, vacation rental in Leeward
Seagrace Villa Luxury villa, vacation rental in Leeward
Seagrace Villa Luxury villa, vacation rental in Leeward

Seagrace Villa Luxury villa

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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18 Kelly Isle, vacation rental in Leeward
18 Kelly Isle, vacation rental in Leeward
18 Kelly Isle, vacation rental in Leeward

18 Kelly Isle

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Modern Beachfront Villa w/Heated Pool & Jacuzzi, Home Gym, Dock & Staff Included, vacation rental in Leeward
Modern Beachfront Villa w/Heated Pool & Jacuzzi, Home Gym, Dock & Staff Included, vacation rental in Leeward
Modern Beachfront Villa w/Heated Pool & Jacuzzi, Home Gym, Dock & Staff Included, vacation rental in Leeward

Modern Beachfront Villa w/Heated Pool & Jacuzzi, Home Gym, Dock & Staff Included

Rental Home
8 bedrooms
9 bathrooms
Sleeps 16
Match: Sleeps
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30% Discount from June - Nov '23 for 5 nights or more stay!, vacation rental in Leeward
30% Discount from June - Nov '23 for 5 nights or more stay!, vacation rental in Leeward
30% Discount from June - Nov '23 for 5 nights or more stay!, vacation rental in Leeward

30% Discount from June - Nov '23 for 5 nights or more stay!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Entire Villa for Rent, Leeward / Grace Bay, Short Walk to Sunset Beach, vacation rental in Leeward
Entire Villa for Rent, Leeward / Grace Bay, Short Walk to Sunset Beach, vacation rental in Leeward
Entire Villa for Rent, Leeward / Grace Bay, Short Walk to Sunset Beach, vacation rental in Leeward

Entire Villa for Rent, Leeward / Grace Bay, Short Walk to Sunset Beach

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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2 BDRM/2 Bathroom Luxury Condo at The Atrium Resort (BEST RATES), vacation rental in Leeward
2 BDRM/2 Bathroom Luxury Condo at The Atrium Resort (BEST RATES), vacation rental in Leeward
2 BDRM/2 Bathroom Luxury Condo at The Atrium Resort (BEST RATES), vacation rental in Leeward

2 BDRM/2 Bathroom Luxury Condo at The Atrium Resort (BEST RATES)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Newly Renovated 8 Bedroom 7 Bath Villa Spectacular Views Ocean, Beaches close!!!, vacation rental in Leeward
Newly Renovated 8 Bedroom 7 Bath Villa Spectacular Views Ocean, Beaches close!!!, vacation rental in Leeward
Newly Renovated 8 Bedroom 7 Bath Villa Spectacular Views Ocean, Beaches close!!!, vacation rental in Leeward

Newly Renovated 8 Bedroom 7 Bath Villa Spectacular Views Ocean, Beaches close!!!

Rental Home
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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55 Oasis Cottage. Studio suite. Nearby World's #1 Grace Bay Beach., vacation rental in Leeward
55 Oasis Cottage. Studio suite. Nearby World's #1 Grace Bay Beach., vacation rental in Leeward
55 Oasis Cottage. Studio suite. Nearby World's #1 Grace Bay Beach., vacation rental in Leeward

55 Oasis Cottage. Studio suite. Nearby World's #1 Grace Bay Beach.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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5 Bedroom Luxury modern and elegant beach house located along Grace Bay Beach, vacation rental in Leeward
5 Bedroom Luxury modern and elegant beach house located along Grace Bay Beach, vacation rental in Leeward
5 Bedroom Luxury modern and elegant beach house located along Grace Bay Beach, vacation rental in Leeward

5 Bedroom Luxury modern and elegant beach house located along Grace Bay Beach

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Villa Viatu - Impressive modern luxury – steps away from Pelican Beach, vacation rental in Leeward
Villa Viatu - Impressive modern luxury – steps away from Pelican Beach, vacation rental in Leeward
Villa Viatu - Impressive modern luxury – steps away from Pelican Beach, vacation rental in Leeward

Villa Viatu - Impressive modern luxury – steps away from Pelican Beach

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Cozy studio unit at The Atrium Resort Providenciales, Turks & Caicos, vacation rental in Leeward
Cozy studio unit at The Atrium Resort Providenciales, Turks & Caicos, vacation rental in Leeward
Cozy studio unit at The Atrium Resort Providenciales, Turks & Caicos, vacation rental in Leeward

Cozy studio unit at The Atrium Resort Providenciales, Turks & Caicos

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Y.O.L.O - Why not?  No Hidden fees. Walk to Beach  - Fun for the entire family, vacation rental in Leeward
Y.O.L.O - Why not?  No Hidden fees. Walk to Beach  - Fun for the entire family, vacation rental in Leeward
Y.O.L.O - Why not?  No Hidden fees. Walk to Beach  - Fun for the entire family, vacation rental in Leeward

Y.O.L.O - Why not? No Hidden fees. Walk to Beach - Fun for the entire family

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Villa Sentosa | Beach Front - Located in Fabulous Grace Bay with Private Pool, vacation rental in Leeward
Villa Sentosa | Beach Front - Located in Fabulous Grace Bay with Private Pool, vacation rental in Leeward
Villa Sentosa | Beach Front - Located in Fabulous Grace Bay with Private Pool, vacation rental in Leeward

Villa Sentosa | Beach Front - Located in Fabulous Grace Bay with Private Pool

Rental Home
1 bedroom
9 bathrooms
Sleeps 16
Match: Sleeps
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Cozy modern luxury 1bed with 1bath with pool and near to beach and golf course, vacation rental in Leeward
Cozy modern luxury 1bed with 1bath with pool and near to beach and golf course, vacation rental in Leeward
Cozy modern luxury 1bed with 1bath with pool and near to beach and golf course, vacation rental in Leeward

Cozy modern luxury 1bed with 1bath with pool and near to beach and golf course

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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10 Steps to Grace Bay Beach, 4BR sleeps 10, Private Pool, Luxury Villa, vacation rental in Leeward
10 Steps to Grace Bay Beach, 4BR sleeps 10, Private Pool, Luxury Villa, vacation rental in Leeward
10 Steps to Grace Bay Beach, 4BR sleeps 10, Private Pool, Luxury Villa, vacation rental in Leeward

10 Steps to Grace Bay Beach, 4BR sleeps 10, Private Pool, Luxury Villa

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!, vacation rental in Leeward
30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!, vacation rental in Leeward
30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!, vacation rental in Leeward

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Caya Villa 2 - 2 Bedroom - Island Fusion Home, vacation rental in Leeward
Caya Villa 2 - 2 Bedroom - Island Fusion Home, vacation rental in Leeward
Caya Villa 2 - 2 Bedroom - Island Fusion Home, vacation rental in Leeward

Caya Villa 2 - 2 Bedroom - Island Fusion Home

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Stunning Panoramic View - Oceanfront Villa - Calming Charm, vacation rental in Leeward
Stunning Panoramic View - Oceanfront Villa - Calming Charm, vacation rental in Leeward
Stunning Panoramic View - Oceanfront Villa - Calming Charm, vacation rental in Leeward

Stunning Panoramic View - Oceanfront Villa - Calming Charm

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 3 BDRM/3 Bathroom Two-Level Penthouse  at The Atrium Resort, vacation rental in Leeward
Luxury 3 BDRM/3 Bathroom Two-Level Penthouse  at The Atrium Resort, vacation rental in Leeward
Luxury 3 BDRM/3 Bathroom Two-Level Penthouse  at The Atrium Resort, vacation rental in Leeward

Luxury 3 BDRM/3 Bathroom Two-Level Penthouse at The Atrium Resort

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area, vacation rental in Leeward
WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area, vacation rental in Leeward
WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area, vacation rental in Leeward

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Brand New Waterfront Luxury Villa With Views!!, vacation rental in Leeward
Brand New Waterfront Luxury Villa With Views!!, vacation rental in Leeward
Brand New Waterfront Luxury Villa With Views!!, vacation rental in Leeward

Brand New Waterfront Luxury Villa With Views!!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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10 steps from Grace Bay beach, newly renovated, 9 bedroom house, sleeps 20, vacation rental in Leeward
10 steps from Grace Bay beach, newly renovated, 9 bedroom house, sleeps 20, vacation rental in Leeward
10 steps from Grace Bay beach, newly renovated, 9 bedroom house, sleeps 20, vacation rental in Leeward

10 steps from Grace Bay beach, newly renovated, 9 bedroom house, sleeps 20

Rental Home
9 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda, vacation rental in Leeward
Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda, vacation rental in Leeward
Villa - Canal Front - Large Sun Deck- Outdoor Lounge/Covered Veranda, vacation rental in Leeward

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Large Leeward Condo - walk to the beach, vacation rental in Leeward
Luxury Large Leeward Condo - walk to the beach, vacation rental in Leeward
Luxury Large Leeward Condo - walk to the beach, vacation rental in Leeward

Luxury Large Leeward Condo - walk to the beach

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Private Oasis with Pool, vacation rental in Leeward
Private Oasis with Pool, vacation rental in Leeward
Private Oasis with Pool, vacation rental in Leeward

Private Oasis with Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Sanmar Villa, vacation rental in Leeward
Sanmar Villa, vacation rental in Leeward
Sanmar Villa, vacation rental in Leeward

Sanmar Villa

Rental Home
3 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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