Leeward Vacation Rentals & Homes with Swimming Pool - 132 Rentals Available.
132 Vacation rentals
Filters applied: Swimming pool

Private beachfront villa on Grace Bay sleeps 12
Leeward Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$1,857.00
from $1,857.00 / night

Aqueous - Sunset Beach Villas TCI
Leeward Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 38 minutes
$1,374.00
from $1,374.00 / night

Turnstone House - Sunset Beach Villas
Leeward Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 38 minutes
$1,661.00
from $1,661.00 / night


Brand new nearly beachfront 4 bedroom villa
Leeward Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$1,300.00
from $1,300.00 / night

Beach House At Hawkbill Beach Front Located in Wonderful Grace Bay with Pri
Leeward Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,000.00
from $2,000.00 / night

Villa Hawksbill Beach Front Located in Stunning Grace Bay with Private Pool
Leeward Villa
- 8 bedrooms 8
- 8 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$16,900.00
from $16,900.00 / night

Villa Hawksbill Beach Front Located in Tropical Grace Bay with Private Poo
Leeward Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$10,850.00
from $10,850.00 / night

Villa Hawksbill Beach Front Located in Exquisite Grace Bay with Private Poo
Leeward Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$14,500.00
from $14,500.00 / night

Turquoise Villa Near Ocean Located in Tropical Grace Bay with Private Pool
Leeward Villa
- 1 bedroom 1
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,950.00
from $1,950.00 / night

Villa Milestone Beach Front Located in Beautiful Grace Bay with Private Po
Leeward Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,750.00
from $3,750.00 / night
Your search has been expanded 11 miles to include more rentals

Pelican Nest Cinnamon Villa - 300 ft. of private beach on Grace Bay
Grace Bay Villa - 0.1 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 44 minutes
$983.00
from $983.00 / night

Edge of Paradise 3 bedroom Luxury Villa steps to Grace Bay
Grace Bay Villa - 0.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Responds fast! Avg. 38 minutes
$1,432.00
from $1,432.00 / night

Villas 5 bedroom Main & 4 bedroom Guest house
Providenciales Villa - 10.2 miles away
- 9 bedrooms 9
- 7 bathrooms
- sleeps 18 18
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 2 mi
- Swimming pool
$1,963.00
from $1,963.00 / night

*OCEAN VIEW FULL KITCHEN* 1 Bedroom Suite La Vista Azul *New furniture April/17*
Turtle Cove Condo - 5 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$235.00
from $235.00 / night

Waterfront Leeward Villa
Grace Bay Villa - 0.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$540.00
from $540.00 / night

Xanadu, Chic secluded beach living, indulge in the ultimate Caribbean vacation.
Turtle Cove Cottage - 5.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.1 mi
- Swimming pool
$575.00
from $575.00 / night

Blue Villa - 3BR On Grace Bay Beach
Turtle Cove Villa - 4.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 4 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$398.00
from $398.00 / night

Luxury 4-Bedroom Beachfront Villa private pool
Providenciales Villa - 5.9 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$1,071.00
from $1,071.00 / night

Samsara, private luxury retreat, indulge in the ultimate Caribbean vacation!
Providenciales Villa - 5.9 miles away
- 7 bedrooms 7
- 8 bathrooms
- sleeps 22 22
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$5,250.00
from $5,250.00 / night

Newly Constructed Cottage in Leeward
Providenciales Cottage - 0.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
Responds fast! Avg. 3 hours 3 minutes
$458.00
from $458.00 / night

Second Chances 5 Bed Villa in Grace Bay
Grace Bay Villa - 0.1 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
Responds fast! Avg. 38 minutes
$3,378.00
from $3,378.00 / night

2bdrm ocean front views, pool, hot tub, beach,
Providenciales Apartment - 11 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- 1 night min
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
Responds fast! Avg. 3 hours 45 minutes
$745.00
from $745.00 / night

Ocean Edge Villa on Grace Bay Beach, turquoise views & great snorkeling!
Providenciales Villa - 5.2 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$426.00
from $426.00 / night

Ocean View 2 bdrm pool, hot tub and private beach
Turtle Cove Penthouse - 11 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Responds fast! Avg. 3 hours 45 minutes
$687.00
from $687.00 / night

2 bdrm ocean view pool, hot tub, beach, nice
Providenciales Apartment - 11 miles away
- 2 bedrooms 2
- 5 bathrooms
- sleeps 4 4
- 3 nights min
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
Responds fast! Avg. 3 hours 45 minutes
$573.00
from $573.00 / night

Coccoloba Beach House, a 2BR with Private Pool on Taylor Bay Beach
Providenciales Villa - 10.1 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$562.00
from $562.00 / night

Two story colonial styled villa
Grace Bay Villa - 0.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,300.00
from $2,300.00 / night

3 bdrm, oceanfront , beach, views, pool, hot tub
Turtle Cove Apartment - 11 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 1 night min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 3 hours 45 minutes
$916.00
from $916.00 / night

Callaloo Cottage, a 1BR beachfront villa with island's best snorkeling
Turtle Cove Cottage - 5.2 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$471.00
from $471.00 / night

Villa Conch Beach Front Located in Magnificent Grace Bay with Private Pool
Grace Bay Villa - 0.1 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,650.00
from $2,650.00 / night

Stunning beach front 4 bedroom villa
Grace Bay Villa - 0.1 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,425.00
from $2,425.00 / night

Coral House Beach Front Located in Magnificent Grace Bay with Private Pool
Grace Bay Villa - 0.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$7,350.00
from $7,350.00 / night

5 bedroom plantation estate
Grace Bay Villa - 0.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,950.00
from $4,950.00 / night

Conch Beach Villa 3BR on Grace Bay Beach with tons of Amenities and pool!
Providenciales Villa - 4.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$851.00
from $851.00 / night

Miami Vice Two 2BR Oceanfront Villa with beautiful views of Sapodilla Bay
Providenciales Villa - 9.8 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$681.00
from $681.00 / night

Villa Saving Grace Beach Front Located in Fabulous Grace Bay with Private
Grace Bay Villa - 0.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,250.00
from $4,250.00 / night

Beautifully styled 8 bedroom estate home
Grace Bay Villa - 0.1 miles away
- 8 bedrooms 8
- 8 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$10,350.00
from $10,350.00 / night

Sandy Beaches 5BR Villa on Long Bay Beach with Unending Turquoise Views!
Long Bay Beach Villa - 3.3 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,114.00
from $1,114.00 / night

Stunning Turquoise Views at Aguaribay Beachfront 5BR Villa on Long Bay
Providenciales Villa - 2.6 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,557.00
from $1,557.00 / night
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