Leeward Vacation Rentals & Homes with Swimming Pool - 65 Rentals Available.
65 Vacation rentals
Filters applied: Swimming pool
BRAND NEW Aqueous - Sunset Beach Villas TCI
Leeward Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,088.00
from $1,088.00 / night
Villa Cabuya | Beach Front - Located in Exquisite Leeward
Leeward Villa
- 1 bedroom 1
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$5,565.00
from $5,565.00 / night
Villa Alee - Brand new luxury villa - Only 10 min walk to Grace Bay beach!
Leeward Villa
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$745.00
from $745.00 / night
Villa Cabuya | Beach Front - Located in Stunning Leeward with Private Pool
Leeward Villa
- 1 bedroom 1
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$5,250.00
from $5,250.00 / night
Villa Blondel Cove | Beach Front - Located in Tropical Leeward with Private Poo
Leeward Villa
- 1 bedroom 1
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$6,300.00
from $6,300.00 / 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
$2,546.00
from $2,546.00 / night
Your search has been expanded 11 miles to include more rentals
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. 20 minutes
$458.00
from $458.00 / night
Blue Villa 2BR – CLOSED
Turtle Cove Villa - 4.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$428.00
from $428.00 / 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
$258.00
from $258.00 / 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. 1 hour 6 minutes
$745.00
from $745.00 / 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. 1 hour 6 minutes
$916.00
from $916.00 / night
Ocean pool views 1 bdrm private beach hot tub nice
Providenciales Apartment - 10.9 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 3 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 6 minutes
$401.00
from $401.00 / 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. 1 hour 6 minutes
$687.00
from $687.00 / 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
$1,603.00
from $1,603.00 / 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. 1 hour 6 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
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$2,233.00
from $2,233.00 / night
Villa Beach Cake | Beach Front - Located in Exquisite Grace Bay with Private Po
The Bight Settlement Villa - 5.2 miles away
- 1 bedroom 1
- 3 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,575.00
from $1,575.00 / night
TC Villas // Mandalay Villa // Winner International Property Awards
Long Bay Beach House - 3.1 miles away
- 6 bedrooms 6
- 8 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$10,000.00
from $10,000.00 / night
TC Villas // Caicos Cays Villa // Luxurious Waterfront in Chalk Sound
Turtle Cove Villa - 10.4 miles away
- 5 bedrooms 5
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$843.00
from $843.00 / night
TC Villas // Beachfront Villa Sandpiper // Built on the beach!
The Bight Settlement Villa - 5.1 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$629.00
from $629.00 / night
TC Villas // Little Plum Villa // Direct beach path
The Bight Settlement Villa - 5.1 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$350.00
from $350.00 / night
TC Villas // Miami Vice One // Clean, Modern, Luxurious
Turtle Cove Villa - 9.8 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$418.00
from $418.00 / night
TC Villas // Beach Villa Sandstone // Amazing snorkeling!
The Bight Settlement House - 5.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 9 9
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$757.00
from $757.00 / night
TC Villas // Callaloo Cottage // Romantic Beachfront
The Bight Settlement Cottage - 5.3 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
TC Villas // Gumbo Cottage // Steps to the beach
The Bight Settlement Cottage - 4.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / night
TC Villas // Dawn Beach Villa // Space, Privacy, Comfort
The Bight Settlement Villa - 5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 11 11
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,357.00
from $1,357.00 / night
TC Villas // Aguaribay // Secluded family vacation
Long Bay Beach Villa - 3.4 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,400.00
from $1,400.00 / night
TC Villas // Hillview Cottage // Elevated views & privacy
Turtle Cove House - 8.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$350.00
from $350.00 / night
TC Villas // Conch Beach Villa // Beachfront with private Tennis court!
The Bight Settlement Villa - 4.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$993.00
from $993.00 / night
Hura Sea Villas // 6BR minimalist beachfront // Enjoy added privacy!
Turtle Cove House - 8.2 miles away
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,554.00
from $1,554.00 / night
TC Villas // Sea Edge Villa // Luxury & Romance
The Bight Settlement Villa - 5.2 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$418.00
from $418.00 / night
TC Villas // Nutmeg Cottage // Private pool & beach access
The Bight Settlement Cottage - 5.1 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$307.00
from $307.00 / night
TC Villas // Water Edge Villa // Perfect Honeymoon
The Bight Settlement House - 5.2 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$418.00
from $418.00 / night
TC Villas // Impulse Beach Estate // Large & Luxurious Estate
The Bight Settlement Villa - 4.9 miles away
- 6 bedrooms 6
- 10 bathrooms
- sleeps 20 20
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,071.00
from $3,071.00 / night
TC Villas // Reef Beach House // Beach for a backyard!
The Bight Settlement Villa - 5 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$829.00
from $829.00 / night
TC Villas // Coccoloba Beach House // Comfy, cozy, right on the beach
Turtle Cove Villa - 10.1 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$514.00
from $514.00 / night
TC Villas // Coriander Cottage // Privacy & Romance
The Bight Settlement Cottage - 5.1 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 3 3
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$293.00
from $293.00 / night
TC Villas // Reef Pearl // Private beach deck
The Bight Settlement Villa - 5 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 9 9
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$771.00
from $771.00 / night
TC Villas // Beach Villa Shambhala // Elegant Mansion on the beach
Five Cays Settlement Villa - 2.1 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,700.00
from $1,700.00 / night
TC Villas // Cascade // Ultimate Caribbean Estate
The Bight Settlement House - 5.7 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,222.00
from $2,222.00 / night
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Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.