Simpson Bay Villas & Vacation Rentals with Swimming Pool - 1168 Rentals Available.
1,168 Vacation rentals
Filters applied: Swimming pool
Paradise Found at Las Arenas - Beachfront Luxury!
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
$358.00
from $358.00 / night
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
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
BEACHSIDE CONDO... IRMA Survivor!! You can't get much closer to the beach than
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
IL PUNTO BLUE...Irma Survivor! located right on the beach in prestigious Pelican
Simpson Bay Apartment
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
UNFORGETTABLE... IRMA Survivor!! Beachfront contemporary condo on fabulous beach
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$519.00
from $519.00 / 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
BLUE WATER ... IRMA Survivor !! 2BR condo at Acqua Residences, steps to Simpson
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$429.00
from $429.00 / 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
ATLANTIS... IRMA Survivor!! Located right on Simpson Bay beach!
Simpson Bay Apartment
- 1 bedroom 1
- 1 bathroom
- Sleeps 2 2
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$286.00
from $286.00 / night
SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$372.00
from $372.00 / night
MAHO DREAM... comfortable 2BR penthouse condo at Blue Marine Residence in Maho!!
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$174.00
from $174.00 / 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
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
Contemporary penthouse at La Brisas
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
$455.00
from $455.00 / 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
Coco Beach Duplex
Simpson Bay Villa
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$300.00
from $300.00 / night
SIMPSON BAY BEACH CONDO #2...located right on the beach at beautiful Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$372.00
from $372.00 / night
COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$386.00
from $386.00 / night
COCO BEACH CLUB #5.... step out the door on to the soft white powdery sand of S
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$386.00
from $386.00 / 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
CASA DE BELLA... IRMA Survivor!! great location at a great price!!
Simpson Bay House
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$400.00
from $400.00 / 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
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
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
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
SUR MER * Coco's Beach Club...Irma Survivor, beachfront condo on Simpson Bay Bea
Simpson Bay Apartment
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$772.00
from $772.00 / night
Coco Beach #5 ON THE BEACH
Simpson Bay Apartment
- 2 bedrooms 2
- 5 bathrooms
- Sleeps 6 6
- 1 night min
- Beach/lakeside relaxation
- Swimming pool
- Air conditioning
$372.00
from $372.00 / 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
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
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
SOL Y MAR.. 3 bedroom, 3 bath penthouse villa, beachfront on Kim Sha beach! Walk
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
$795.00
from $795.00 / 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
SEA BEACH TREASURE...Irma Survivor!! Gorgeous 2BR Penthouse on Simpson Bay Beach
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$465.00
from $465.00 / night
MARISOL... IRMA Survivor!! light and airy townhouse at Point Blue in Pelican Key
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$329.00
from $329.00 / 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
RENDEZVOUS... IRMA Survivor!! A fabulous 2 BR contemporary 2 BR condo unit on
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / 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
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / 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
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
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