Leeward Vacation Rentals & Homes with Swimming Pool - 63 Rentals Available.
63 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
Responds fast! Avg. 1 hour 34 minutes
$1,088.00
from $1,088.00 / 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
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
$5,830.00
from $5,830.00 / night
Turquoise Villa | Near Ocean - Located in Magnificent Grace Bay with Private Po
Leeward Villa
- 1 bedroom 1
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,430.00
from $1,430.00 / 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
$5,500.00
from $5,500.00 / 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
$6,600.00
from $6,600.00 / 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
$2,668.00
from $2,668.00 / 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. 2 hours 5 minutes
$458.00
from $458.00 / 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
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. 2 hours 59 minutes
$401.00
from $401.00 / 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. 2 hours 59 minutes
$745.00
from $745.00 / 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. 2 hours 59 minutes
$687.00
from $687.00 / 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. 2 hours 59 minutes
$916.00
from $916.00 / 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
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
$400.00
from $400.00 / night
Samsara TCI, Luxury vacation living, just add family and friends!
Providenciales Villa - 5.9 miles away
- 10 bedrooms 10
- 8 bathrooms
- sleeps 22 22
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$5,000.00
from $5,000.00 / night
Blue Villa 2BR – CLOSED UNTIL FURTHER NOTICE
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
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 27 minutes
$229.00
from $229.00 / 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
$1,650.00
from $1,650.00 / night
Second Chances 5 Bed Villa in Grace Bay
Grace Bay Villa - 0.1 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Ask about children
- Air conditioning
Responds fast! Avg. 1 hour 40 minutes
$2,806.00
from $2,806.00 / 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. 1 hour 40 minutes
$974.00
from $974.00 / night
Classic elegant plantation manor at Grace bay beach
Grace Bay Villa - 0.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$4,950.00
from $4,950.00 / night
Contemporary Luxury one-bedroom beach villa
Grace Bay Villa - 5.1 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
$540.00
from $540.00 / night
Beachfront fully staffed villa with unique design
Grace Bay Villa - 0.1 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Ask about pets
$5,400.00
from $5,400.00 / night
Two story colonial styled villa
Grace Bay Villa - 0.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- 4 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,300.00
from $2,300.00 / 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
$514.00
from $514.00 / night
TC Villas // Sandy Beaches // Secluded Beach Vacation
Long Bay Beach Villa - 3.3 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,114.00
from $1,114.00 / 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
TC Villas // Ocean Edge Villa // Romantic Getaway
The Bight Settlement Villa - 5.2 miles away
- 1 bedroom 1
- 2 bathrooms
- sleeps 3 3
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$471.00
from $471.00 / 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
$829.00
from $829.00 / night
TC Villas // Caicos Cays Villa // Luxurious Waterfront in Chalk Sound
Turtle Cove Villa - 10.4 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$686.00
from $686.00 / 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
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$350.00
from $350.00 / 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
Beachfront breathtaking 6 bedroom villa on Grace Bay Beach
Grace Bay Villa - 1.5 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$6,000.00
from $6,000.00 / night
TC Villas // Plum Wild // Perfect location w. snorkeling
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
$757.00
from $757.00 / night
TC Villas // Villa Isla // Family villa in paradise
Long Bay Beach Villa - 3.4 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,643.00
from $1,643.00 / 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
$1,098.00
from $1,098.00 / 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
Beautiful contemporary style villa on the beach
Grace Bay Villa - 0.1 miles away
- 8 bedrooms 8
- 8 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$15,000.00
from $15,000.00 / 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
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