Simpson Bay Villa Rentals - 401 Rentals Available.
401 Vacation rentals
Filters applied: Villa
TARA... Affordable oceanfront villa, walk to beach
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$657.00
from $657.00 / night
Burgeoux Villa... Comfortable Beach front home, walk to Maho or Simpson Bay bea
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$758.00
from $758.00 / night
CARIBBEAN BLUE... 5BR beachfront home in Pelican Key
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$843.00
from $843.00 / night
WITENBLAUW... Magical Beach Front Estate on Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,072.00
from $2,072.00 / night
BISOU DU SOLEIL... beautiful, immaculate, affordable villa in Pelican Key
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Air conditioning
$672.00
from $672.00 / night
SMART VILLA...Beachfront at Pelican Key
Simpson Bay Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Child friendly
- Air conditioning
- Private garden
$286.00
from $286.00 / night
SOL Y MAR... fabulous beachfront penthouse on Kimsha Beach! Private pool, Walk t
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$557.00
from $557.00 / night
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
ST TROPEZ... amazing views of the Caribbean Sea from this lovely villa in Pelica
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$557.00
from $557.00 / night
Villa Speranza | Near Ocean - Located in Fabulous Simpson Bay with Private Poo
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$692.00
from $692.00 / night
MARY'S BEACH ESTATE... a plane watcher's dream! Huge observation deck at this be
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,523.00
from $1,523.00 / night
FAJA LOBIE... 3 BR Offers Great rates for a beachfront villa
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700.00
from $700.00 / night
SURFSONG... 6BR fall in love again! Breathtaking sunsets, directly on ocean!
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,498.00
from $1,498.00 / night
CARIBBEAN BLUE... 4BR beachfront home in Pelican Key
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$743.00
from $743.00 / night
VILLA VITTORIA... Spectaculer, RARE 6BR villa sits directly on Simpson Bay Beach
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,143.00
from $1,143.00 / night
BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons
Simpson Bay Villa
- 7 bedrooms 7
- 8 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,215.00
from $2,215.00 / night
Your search has been expanded 19.9 miles to include more rentals
Your Paradise Villa
Orient Bay Villa - 5.6 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Swimming pool
$638.00
from $638.00 / night
Luxury Villa with private heated pool and AC in all bedrooms
St Martin / St Maarten Villa - 5.5 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$491.00
from $491.00 / night
Villa Bahari | Beach Front - Located in Fabulous Cupecoy with Private Pool
Cupecoy Bay Villa - 2.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$761.00
from $761.00 / night
Listen to the waves
St. Barthelemy Villa - 17.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
$600.00
from $600.00 / night
$3,571.00
from $3,571.00 / night
Reef Point
St. Jean Villa - 19.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
$2,143.00
from $2,143.00 / night
What is Travelers’ Choice award?
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.