Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 1623 Rentals Available.
1,623 Vacation rentals
Filters applied: 2+ Bedrooms
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
SIMPSON BAY BEACH CONDO #3...right on the beach at Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$515.00
from $515.00 / 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
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
$454.00
from $454.00 / night
Aqualina 102 - Ideal for Couples and Families, Beautiful Pool and Beach
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Air conditioning
$415.00
from $415.00 / 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
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
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
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
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$515.00
from $515.00 / 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
Coco unit 16 - Luxury ocean front condo
Simpson Bay House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 4 nights min
- Ask about children
$343.00
from $343.00 / 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
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / 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
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
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
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
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
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
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
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
- 14 nights min
- Swimming pool
- Child friendly
- Air conditioning
$500.00
from $500.00 / 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 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 - 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
Aqualina 102
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Child friendly
- Ask about pets
$314.00
from $314.00 / 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
$570.00
from $570.00 / 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
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 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
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
Villa Amaryllis Waterfront, Private Pool
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
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
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
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
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 Amaryllis Waterfront, Private Pool
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
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
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
Simpson Bay Yacht Club Condo - Unit 6
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$157.00
from $157.00 / 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
Villa Amaryllis Waterfront, Private Pool
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
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