Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 748 Rentals Available.
748 Vacation rentals
Filters applied: 4+ Bedrooms
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
Coral Breeze - STM
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$856.00
from $856.00 / 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
CORAL BREEZE...Large affordable beachfront villa! Bring the whole family!
Simpson Bay House
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,052.00
from $1,052.00 / 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
Villa La-Di-Da - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / night
SUNSHINE VILLA... IRMA Survivor!! Huge, affordable beachfront villa, full AC, wa
Simpson Bay House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- 7 nights min
- Child friendly
- Air conditioning
$1,715.00
from $1,715.00 / 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
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
LA DI DA...Irma Survivor! 6BR Hilltop Villa Overlooking Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,115.00
from $1,115.00 / 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
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
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
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
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
$1,143.00
from $1,143.00 / 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
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
Villa Amaryllis GREAT REVIEWS Fully Serviced Book Now and Save
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
$435.00
from $435.00 / 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
$809.00
from $809.00 / 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
$1,801.00
from $1,801.00 / 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
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
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
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
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