Leeward 2-bedroom Vacation Rentals, Homes & More - 51 Rentals Available.
51 Vacation rentals
Filters applied: 2+ Bedrooms
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
Grace Haven - brand new villa in Leeward
Leeward Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Child friendly
Responds fast! Avg. 1 hour 34 minutes
$1,203.00
from $1,203.00 / 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 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
2 bdrm, pool, hot tub, beach, very clean, private,
Providenciales Apartment - 11 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Air conditioning
Responds fast! Avg. 2 hours 59 minutes
$630.00
from $630.00 / 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
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
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
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
$10,850.00
from $10,850.00 / 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 // 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 // Turtle Breeze Villa
The Bight Settlement Villa - 5 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 14 14
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,779.00
from $2,779.00 / night
TC Villas // Grace Bay Retreat // Steps to Grace Bay Beach
The Bight Settlement House - 3.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
$500.00
from $500.00 / 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 // 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 // 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
$1,929.00
from $1,929.00 / 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 // 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 // Beach Villa Shambhala // Elegant Mansion on the beach
Five Cays Settlement Villa - 2.1 miles away
- 5 bedrooms 5
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,700.00
from $1,700.00 / 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 // 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
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
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
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
Contemporary beach front villa at Grace Bay beach
Grace Bay Villa - 0.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,425.00
from $2,425.00 / 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
$850.00
from $850.00 / 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
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
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
$443.00
from $443.00 / night
TC Villas // Conched Out Villa // Large family retreat
Long Bay Beach Villa - 3.1 miles away
- 7 bedrooms 7
- 8 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,543.00
from $1,543.00 / night
Spectacular spacious 8 bedroom family home
The Bight Settlement Villa - 5.5 miles away
- 8 bedrooms 8
- 8 bathrooms
- sleeps 16 16
- min stay varies
- Child friendly
- Air conditioning
$4,200.00
from $4,200.00 / night
TC Villas // Villa Sandpebble // Perfect Location!
The Bight Settlement Villa - 5.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 7 7
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786.00
from $786.00 / 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
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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.