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Leeward Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
208 rentals in Leeward.
VillaKendara~FREENITE 10/28-11/4~Private~Gated~SeaFront GuestHous~Panoramic View, vacation rental in Leeward
VillaKendara~FREENITE 10/28-11/4~Private~Gated~SeaFront GuestHous~Panoramic View, vacation rental in Leeward
VillaKendara~FREENITE 10/28-11/4~Private~Gated~SeaFront GuestHous~Panoramic View, vacation rental in Leeward

VillaKendara~FREENITE 10/28-11/4~Private~Gated~SeaFront GuestHous~Panoramic View

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Byculla 4 BR Villa - Canal Front, vacation rental in Leeward
Byculla 4 BR Villa - Canal Front, vacation rental in Leeward
Byculla 4 BR Villa - Canal Front, vacation rental in Leeward

Byculla 4 BR Villa - Canal Front

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Villa Tropica | Near Grace Bay Beach | Newly Remodeled, vacation rental in Leeward
Villa Tropica | Near Grace Bay Beach | Newly Remodeled, vacation rental in Leeward
Villa Tropica | Near Grace Bay Beach | Newly Remodeled, vacation rental in Leeward

Villa Tropica | Near Grace Bay Beach | Newly Remodeled

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Sunset One Beach Villa - Golf Cart, Kayaks, and Paddleboards; Free Beach Set Up, vacation rental in Leeward
Sunset One Beach Villa - Golf Cart, Kayaks, and Paddleboards; Free Beach Set Up, vacation rental in Leeward
Sunset One Beach Villa - Golf Cart, Kayaks, and Paddleboards; Free Beach Set Up, vacation rental in Leeward

Sunset One Beach Villa - Golf Cart, Kayaks, and Paddleboards; Free Beach Set Up

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Aug and Sept 25% off at super popular Villa!, vacation rental in Leeward
Aug and Sept 25% off at super popular Villa!, vacation rental in Leeward
Aug and Sept 25% off at super popular Villa!, vacation rental in Leeward

Aug and Sept 25% off at super popular Villa!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Moringa Villa, vacation rental in Leeward
Moringa Villa, vacation rental in Leeward
Moringa Villa, vacation rental in Leeward

Moringa Villa

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Private Resort Style Villa and pool close to beaches, vacation rental in Leeward
Private Resort Style Villa and pool close to beaches, vacation rental in Leeward
Private Resort Style Villa and pool close to beaches, vacation rental in Leeward

Private Resort Style Villa and pool close to beaches

Holiday Rental House
2 bedrooms
3 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.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay., vacation rental in Leeward
Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay., vacation rental in Leeward
Gorgeous Pool, Private Garden, 5 min walk to Pelican Beach on Grace Bay., vacation 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. 4 ocean faciig bedrooms. Private pool, water access. Holiday dream!, vacation rental in Leeward
Oceanfront. 4 ocean faciig bedrooms. Private pool, water access. Holiday dream!, vacation rental in Leeward
Oceanfront. 4 ocean faciig bedrooms. Private pool, water access. Holiday dream!, vacation rental in Leeward

Oceanfront. 4 ocean faciig bedrooms. Private pool, water access. Holiday dream!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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30 Second Walk  to Grace Bay Beach!,  3BR,  Private Pool!   Lush Gardens!!, vacation rental in Leeward
30 Second Walk  to Grace Bay Beach!,  3BR,  Private Pool!   Lush Gardens!!, vacation rental in Leeward
30 Second Walk  to Grace Bay Beach!,  3BR,  Private Pool!   Lush Gardens!!, vacation rental in Leeward

30 Second Walk to Grace Bay Beach!, 3BR, Private Pool! Lush Gardens!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER, vacation rental in Leeward
LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER, vacation rental in Leeward
LIQUID LUXURY - NEW NEW NEW TURKS & CAICOS PRIVATE VILLA ON THE WATER, vacation 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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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!!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2, vacation rental in Leeward
Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2, vacation rental in Leeward
Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2, vacation rental in Leeward

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Villa Vivace - New Luxurious Seaside Home, vacation rental in Leeward
Villa Vivace - New Luxurious Seaside Home, vacation rental in Leeward
Villa Vivace - New Luxurious Seaside Home, vacation rental in Leeward

Villa Vivace - New Luxurious Seaside Home

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Pelican Vista: 150 yards from Grace Bay Beach!, vacation rental in Leeward
Pelican Vista: 150 yards from Grace Bay Beach!, vacation rental in Leeward
Pelican Vista: 150 yards from Grace Bay Beach!, vacation rental in Leeward

Pelican Vista: 150 yards from Grace Bay Beach!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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Beauty and the Beach!, vacation rental in Leeward
Beauty and the Beach!, vacation rental in Leeward
Beauty and the Beach!, vacation rental in Leeward

Beauty and the Beach!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Second Chances Modern Luxury in Gated Community, vacation rental in Leeward
Second Chances Modern Luxury in Gated Community, vacation rental in Leeward
Second Chances Modern Luxury in Gated Community, vacation rental in Leeward

Second Chances Modern Luxury in Gated Community

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Piccolo Ponte | 3 BR Caribbean Villa & Pool & SPA | Canal front, vacation rental in Leeward
Piccolo Ponte | 3 BR Caribbean Villa & Pool & SPA | Canal front, vacation rental in Leeward
Piccolo Ponte | 3 BR Caribbean Villa & Pool & SPA | Canal front, vacation rental in Leeward

Piccolo Ponte | 3 BR Caribbean Villa & Pool & SPA | Canal front

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
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.

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

Moringa Villa

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Where Sun Happens!!!, vacation rental in Leeward
Where Sun Happens!!!, vacation rental in Leeward
Where Sun Happens!!!, vacation rental in Leeward

Where Sun Happens!!!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Listing 60 Second Walk  to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!, vacation rental in Leeward
New Listing 60 Second Walk  to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!, vacation rental in Leeward
New Listing 60 Second Walk  to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!, vacation rental in Leeward

New Listing 60 Second Walk to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Edge of Paradise Modern Luxury in Gated Community, vacation rental in Leeward
Edge of Paradise Modern Luxury in Gated Community, vacation rental in Leeward
Edge of Paradise Modern Luxury in Gated Community, vacation rental in Leeward

Edge of Paradise Modern Luxury in Gated Community

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 6
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!!!

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 20
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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy & Chic | Grace Bay Beach | Pets Welcome!, vacation rental in Leeward
Cozy & Chic | Grace Bay Beach | Pets Welcome!, vacation rental in Leeward
Cozy & Chic | Grace Bay Beach | Pets Welcome!, vacation 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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2 bed villa - Closest villa to the ocean on island!, vacation rental in Leeward
2 bed villa - Closest villa to the ocean on island!, vacation rental in Leeward
2 bed villa - Closest villa to the ocean on island!, vacation 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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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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Barefoot Bliss - Leeward cottage w/ private pool & short walk to the beach, vacation rental in Leeward
Barefoot Bliss - Leeward cottage w/ private pool & short walk to the beach, vacation rental in Leeward
Barefoot Bliss - Leeward cottage w/ private pool & short walk to the beach, vacation rental in Leeward

Barefoot Bliss - Leeward cottage w/ private pool & short walk to the beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Cozy House, 3 bedroom, Short walk to best beach,  Grace Bay Beach,, vacation rental in Leeward
The Cozy House, 3 bedroom, Short walk to best beach,  Grace Bay Beach,, vacation rental in Leeward
The Cozy House, 3 bedroom, Short walk to best beach,  Grace Bay Beach,, vacation rental in Leeward

The Cozy House, 3 bedroom, Short walk to best beach, Grace Bay Beach,

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

Salt Air Villa

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Handfield's Hideaway Cozy one bedroom, vacation rental in Leeward
Handfield's Hideaway Cozy one bedroom, vacation rental in Leeward
Handfield's Hideaway Cozy one bedroom, vacation rental in Leeward

Handfield's Hideaway Cozy one bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Waterfront Luxury Villa with Optional Boat and Beach Access Just Steps Away, vacation rental in Leeward
Waterfront Luxury Villa with Optional Boat and Beach Access Just Steps Away, vacation rental in Leeward
Waterfront Luxury Villa with Optional Boat and Beach Access Just Steps Away, vacation rental in Leeward

Waterfront Luxury Villa with Optional Boat and Beach Access Just Steps Away

Holiday Rental House
7 bedrooms
0 bathrooms
Sleeps 16
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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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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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!!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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AMAZING GRACE VILLA - 5-bedroom Luxury Beachfront Villa on Grace Bay Beach, vacation rental in Leeward
AMAZING GRACE VILLA - 5-bedroom Luxury Beachfront Villa on Grace Bay Beach, vacation rental in Leeward
AMAZING GRACE VILLA - 5-bedroom Luxury Beachfront Villa on Grace Bay Beach, vacation rental in Leeward

AMAZING GRACE VILLA - 5-bedroom Luxury Beachfront Villa on Grace Bay Beach

Holiday Rental House
1 bedroom
6 bathrooms
Sleeps 10
Match: Sleeps
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Chic Waterfront Villa, vacation rental in Leeward
Chic Waterfront Villa, vacation rental in Leeward
Chic Waterfront Villa, vacation rental in Leeward

Chic Waterfront Villa

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Caribbean Chic Villa with private pool; 4 min to Beach!, vacation rental in Leeward
Caribbean Chic Villa with private pool; 4 min to Beach!, vacation rental in Leeward
Caribbean Chic Villa with private pool; 4 min to Beach!, vacation rental in Leeward

Caribbean Chic Villa with private pool; 4 min to Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New Luxury Waterfront Private Escape- Sugar Apple Villa, vacation rental in Leeward
New Luxury Waterfront Private Escape- Sugar Apple Villa, vacation rental in Leeward
New Luxury Waterfront Private Escape- Sugar Apple Villa, vacation rental in Leeward

New Luxury Waterfront Private Escape- Sugar Apple Villa

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
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!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sugar Apple Villa - A modern, waterside base, vacation rental in Leeward
Sugar Apple Villa - A modern, waterside base, vacation rental in Leeward
Sugar Apple Villa - A modern, waterside base, vacation rental in Leeward

Sugar Apple Villa - A modern, waterside base

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Byculla Villa, vacation rental in Leeward
Byculla Villa, vacation rental in Leeward
Byculla Villa, vacation rental in Leeward

Byculla Villa

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Romantic Getway Steps from the Beach, vacation rental in Leeward
Romantic Getway Steps from the Beach, vacation rental in Leeward
Romantic Getway Steps from the Beach, vacation rental in Leeward

Romantic Getway Steps from the Beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Showing results 1-50 of 208
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