Leeward Vacation Rentals
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Bedrooms
Bathrooms
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Distinctive Features
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5 km
208 rentals 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
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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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
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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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.
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.
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!
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!!
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
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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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
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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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
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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!
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
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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
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
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
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.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Moringa Villa
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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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!!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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!!!
Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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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
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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!
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!
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
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
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,
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Salt Air Villa
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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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
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
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)
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!!
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
Holiday Rental House
1 bedroom
6 bathrooms
Sleeps 10
Match: Sleeps
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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!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sugar Apple Villa - A modern, waterside base
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Byculla Villa
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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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
Frequently Asked Questions about Leeward
- Yes, here are some popular vacation rentals in Leeward that have a pool:
- Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach
- Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony
- Ocean Dream 5 BR Aqua
- Yes, here are some popular vacation rentals in Leeward that have internet access:
- Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach
- Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony
- Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!
- Some of the most popular kid friendly rentals in Leeward are:
- Paradise Apartment: Exquisite Short-Term Rental - Steps from Grace Bay Beach
- Tropical Oasis Retreat: Romantic Upstairs Unit with Pool View and Balcony
- Pelican Cottage -Minutes to Grace Bay Beach! Bikes included!/Car for Rent!