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300+ stays

Stays in Leeward Settlement

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SUPERHOST
Entire house
Maddy's Cottage at SEE TURTLE HOUSE
2 guests1 bedroom1 bed1 bath
PoolAir conditioning
Price:$100 / night
SUPERHOST
Entire guest suite
Erisa Private En-suite ½ mile from Gracebay Beach
2 guests1 bedroom1 bed1 bath
Air conditioningKitchen
Price:$85 / night
SUPERHOST
Entire condominium
★★★★★ Modern Condo | Amazing Pool | Full Kitchen
5 guests2 bedrooms3 beds2 baths
PoolAir conditioningKitchen
Price:$210 / night
Entire cottage
Hummingbird Guesthouse Sleeps 4 250m from beach
4 guests1 bedroom2 beds1 bath
Air conditioningKitchen
Price:$205 / night
SUPERHOST
Entire apartment
Romantic Vacation at La Casita
2 guests1 bedroom1 bed1 bath
PoolAir conditioning
Price:$240 / night
SUPERHOST
Entire villa
Turks and Caicos Islands, Grace Bay Beach, New
6 guests2 bedrooms3 beds2.5 baths
PoolAir conditioningKitchen
Price:$498 / night
Entire house
A Private Deluxe Residence near Grace Bay - Car
2 guests1 bedroom2 beds1 bath
Air conditioningKitchen
Price:$100 / night
SUPERHOST
Entire guesthouse
Pelican Cottage -Mins. to the Beach!! Car 4 Rent!
2 guestsStudio1 bed1 bath
Air conditioningKitchen
Price:$150 / night
Entire guesthouse
New Cool Guest House!
2 guests1 bedroom1 bed1 bath
PoolAir conditioningKitchen
Price:$99 / night
SUPERHOST
Entire townhouse
Josy Villa New Location Grace Bay
5 guests2 bedrooms3 beds2 baths
PoolAir conditioningKitchen
Price:$207 / night
SUPERHOST
Entire house
island Retreat lll
2 guests1 bedroom1 bed1 bath
PoolAir conditioningKitchen
Price:$135 / night
SUPERHOST
Entire villa
Hakuna Matata Villa - Sleeps 7 with pool
7 guests3 bedrooms5 beds3 baths
PoolAir conditioningKitchen
Price:$359 / night
SUPERHOST
Entire house
Sunset Paradise - One bedroom/pool
2 guests1 bedroom1 bed1 bath
PoolAir conditioningKitchen
Price:$111 / night
SUPERHOST
Entire villa
Cozy & Chic | Grace Bay Beach | Pets Welcome!
4 guests2 bedrooms2 beds2.5 baths
PoolAir conditioningKitchen
Price:$410 / night
Entire apartment
Spacious 1 BDRM/1.5 Bath Condo in Gated Resort
3 guests1 bedroom1 bed1.5 baths
PoolAir conditioningKitchen
Price:$188 / night
SUPERHOST
Entire apartment
Palms Hideaway......1/2 mile to Grace Bay Beach!!
2 guests1 bedroom1 bed1 bath
Air conditioningKitchen
Price:$150 / night
SUPERHOST
Entire apartment
Leisure in Paradise
3 guests1 bedroom1 bed1 bath
PoolAir conditioning
Price:$225 / night
SUPERHOST
Entire house
Charming Garden cottage in Leeward
2 guests1 bedroom1 bed1 bath
PoolAir conditioningKitchen
Price:$175 / night
SUPERHOST
Entire house
PERIWINKLE | Charming Caribbean Home|Near to Beach
4 guests2 bedrooms2 beds2 baths
Air conditioningKitchen
Price:$255 / night
Entire house
Hummingbird Villa - Large pool steps from beach
6 guests2 bedrooms4 beds2.5 baths
PoolAir conditioningKitchen
Price:$450 / night
1 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.