Leeward Holiday Rentals
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127 rentals in Leeward.
Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
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Private Oasis with Pool
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New Listing 60 Second Walk to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!
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Private Resort Style Villa and Pool close to beaches
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Romantic Getway Steps from the Beach
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Villa Vivace - New Luxurious Seaside Home
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Cozy & Chic Grace Bay Beach Pets Welcome!
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Cozy Beach House on Kite Boarding Beach,W/Private Pool and kayak.
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30 Second Walk to Grace Bay Beach!, 3BR, Private Pool! Lush Gardens!!
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Villa Tropica - Near Grace Bay Beach - Newly Remodelled
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SunsetOne Beach Villa - Golf Cart 6 seats, Kayaks, SUPs; Free Beach Set Up
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Popular Villa with great service and great value!
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Villa Kendara~BOOK APRIL 5th ON~Private~Gated~SeaFront GuestHouse~Panoramic View
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Charming Cottage
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Guest House 2 bedrooms & 2 baths near Grace Bay Beach & Long Bay Beach.
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Beauty and the Beach!
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Byculla 4 BR Villa - Canal Front
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Entire Villa for Rent, Leeward / Grace Bay, Short Walk to Sunset Beach
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2 BDRM/2 Bathroom Luxury Condo at The Atrium Resort (BEST RATES)
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1 Bedroom Luxury Modern Leeward Condo - 5 min walk from the beach
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30 Seconds to the Grace Bay Beach! 5 BR, Private Pool, Lush Gardens!!!
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Kick Back and Relax Tiki Style!
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Brand New Waterfront Luxury Villa With Views!!
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2 bed villa - Closest villa to the ocean on island!
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The Cozy House, 3 bedroom, Short walk to best beach, Grace Bay Beach,
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WATERFRONT& Private POOL *Hawksbill House in safe, prestigious area
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30 Second Walk to Grace Bay Beach!, 3BR +1BR (4) , Private Pool! Lush Gardens!!
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Ocean Pearl - A Cozy Room in Villa Near Sunset beach, Gracebay, Noah'sark Marina
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Ocean Pearl-Getaway Entire 2bedroom/bath villa near sunset Beach Leeward
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NEW! Luxury 1-Bed Condo in Upscale Gated Community !
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Barefoot Bliss - Leeward villa with private pool & short walk to the beach
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Grace's Condo in Leeward Settlement
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Perroquet | Family Villa near Leeward Beach
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Luxury Large Leeward Condo - walk to the beach
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Two BR Pool Villa on the Water - Near Grace Bay Beach, Golf. Kayaks, SUPs Bikes
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Vista Blue Rental-Grace Bay Beach just 4 mins away
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BOOK NOW FOR FALL 2024 Through Dec. 19, 2024 & Winter 2025!
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NEW! Luxury Modern 1Bd Condo, close to the beach
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Caribbean Chic Villa with private pool; 4 min to Beach!
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NEW!! Luxury 3-Bed Condo in Upscale Gated Community! 5 Minute Walk to the Beach
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18 Kelly Isle
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Stunning two level colonial styled villa on the beach
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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NEW! 1 Bedroom Luxury Modern Condo - very close to the beach
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Contemporary 3 bedroom beachfront beach house
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The Caicos House in Gated Community
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Apartment- 5 Mins Drive to the Beach
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1 Minute Walk To Grace Bay Pelican Beach!!! Nice Gardens!!
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Villa Seabatical - Upper East Side Estate # 12
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Two Acre Beachfront Estate With 2 Beach Decks, Bar, Gym, Volleyball & Pickleball
Holiday Rental House
10 bedrooms
12 bathrooms
Sleeps 20
Match: Sleeps
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Caya Villa 2 - 2 Bedroom - Island Fusion Home
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Showing results 1-50 of 127
Frequently Asked Questions about Leeward
- Yes, here are some popular holiday rentals in Leeward that have a pool:
- Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
- Private Oasis with Pool
- New Listing 60 Second Walk to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!
- Yes, here are some popular holiday rentals in Leeward that have internet access:
- Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
- Private Oasis with Pool
- New Listing 60 Second Walk to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!
- Some of the most popular kid friendly rentals in Leeward are:
- Cozy Beach House 2 on Kite Boarding Beach. Silver Palm Cottage #2
- Private Oasis with Pool
- New Listing 60 Second Walk to Grace Bay Beach! 1BR, Lush Gardens!! New Villa!!