Simpson Bay Villa Rentals - 1514 Rentals Available.
1,514 Vacation rentals
Filters applied: Villa
Faja Lobie - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$412.00
from $412.00 / night
Provence - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
CLIFF HOUSE... IRMA Survivor!! charming, affordable, modern 2BR oceanfront renta
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$472.00
from $472.00 / night
La Vista Grande - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$529.00
from $529.00 / night
BISOU DU SOLEIL ... IRMA Survivor !! (Formerly Riviera) 3 BR hillside villa Pel
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$672.00
from $672.00 / night
BELLE AMOUR... IRMA Survivor!! 5BR fall in love again! Breathtaking sunsets righ
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$829.00
from $829.00 / night
Diamond Chateau - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 7 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$772.00
from $772.00 / night
WITENBLAUW... Irma Survivor, Magical Beach Front Estate on Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,000.00
from $3,000.00 / night
CARIBBEAN BLUE... IRMA Survivor 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
$1,272.00
from $1,272.00 / night
Villa Amaryllis - Waterfront * Located in Fabulous Simpson Bay with Private Po
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$637.00
from $637.00 / night
Tropical Paradise Villa at Coral Shores in Pelican
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 5 nights min
$234.00
from $234.00 / night
SAPPHIRE... IRMA Survivor!! A casual, comfortable villa with ocean views in Pel
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
Beautiful 5 bedroom contemporary villa
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
Responds fast! Avg. 3 hours 57 minutes
$1,143.00
from $1,143.00 / night
Riviera - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$415.00
from $415.00 / night
Francesca - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
Villa Sapphire - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$358.00
from $358.00 / night
St. Tropez - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$558.00
from $558.00 / night
Belle Amour - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$543.00
from $543.00 / night
PROVENCE... IRMA Survivor!! Affordable villa, gorgeous views, close to dining,
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,386.00
from $1,386.00 / night
Villa Amaryllis - Waterfront * Located in Magnificent Simpson Bay with Private
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$693.00
from $693.00 / night
Coral Breeze - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$856.00
from $856.00 / night
TARA... IRMA Survivor!! 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
$843.00
from $843.00 / night
La Casita - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$358.00
from $358.00 / night
Villa Tara - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$658.00
from $658.00 / night
Villa Amaryllis ^ Waterfront :: Located in Wonderful Simpson Bay with Private
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$778.00
from $778.00 / night
Villa Vista - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$457.00
from $457.00 / night
St. Tropez - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$558.00
from $558.00 / night
Witenblauw Estate - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,800.00
from $1,800.00 / night
Villa Hardman
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
$143.00
from $143.00 / night
Caribbean Blue - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
LA CASITA...charming, comfortable oceanfront villa in Beacon Hill, St Maarten
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$543.00
from $543.00 / night
Daffodil - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Air conditioning
$1,072.00
from $1,072.00 / night
Indigo-Sky-Villa - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$368.00
from $368.00 / night
BEAU RIVAGE... IRMA Survivor!! comfortable home on Burgeoux Bay beach, walk to M
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / night
Beautiful beachfront 5 bedroom villa
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Ask about pets
Responds fast! Avg. 3 hours 57 minutes
$809.00
from $809.00 / night
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