Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 986 Rentals Available.
986 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
$409.00
from $409.00 / night
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
$572.00
from $572.00 / 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
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
$1,272.00
from $1,272.00 / night
BEAU RIVAGE... Comfortable home on Burgeoux Bay beach, walk to Maho or Simpson B
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
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
$400.00
from $400.00 / night
SAPPHIRE... A casual, comfortable villa with ocean views in Pelican Key!
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
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
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
$729.00
from $729.00 / 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
$429.00
from $429.00 / 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
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
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
WITENBLAUW... 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... Light and airy townhouse at Point Blue in Pelican Key Estate
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
IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key
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
COCO BEACH CLUB 6...walk right out onto the beach at Simpson Bay
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$400.00
from $400.00 / 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
CASA DE BELLA... 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
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
$1,386.00
from $1,386.00 / night
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!
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
CARIBBEAN SUN... Charming Beachfront Condo on Simpson Bay, Perfect for Couples!
Simpson Bay Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$529.00
from $529.00 / night
SEA BEACH TREASURE... Gorgeous 2BR Penthouse on Simpson Bay Beach, St Maarten
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
UNFORGETTABLE... 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
5% Off Plus Airport Transfer # Waterfront | Located in Fabulous Simpson Bay wi
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
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
$729.00
from $729.00 / night
SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to restaurant
Simpson Bay House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572.00
from $572.00 / night
5% Off Plus Airport Transfer :: Waterfront - Located in Stunning Simpson Bay w
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
5% Off Plus Airport Transfer ^ Waterfront * Located in Tropical Simpson Bay wi
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$787.00
from $787.00 / night
BEACHSIDE CONDO... You can't get much closer to the beach than this!!
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
Coco unit 16 - Luxury ocean front condo
Simpson Bay House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 4 nights min
- Ask about children
- Ask about pets
$342.00
from $342.00 / night
Your search has been expanded 19.7 miles to include more rentals
Luxury Villa with private heated pool and full AC
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
$358.00
from $358.00 / night
Sandcastle Villa - Luxury Beachfront (owner)
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1,900.00
from $1,900.00 / night
Casa Roc | Ocean View * Located in Fabulous Gustavia with Private Pool
Gustavia Villa - 19.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
Complimentry $150 USD Grocery Credit Upon Arrival :: Beach Front ^ Located in S
Cupecoy Bay Villa - 2.6 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$929.00
from $929.00 / night
Complimentry $100 USD Grocery Credit Upon Arrival * Beach Front # Located in Tr
Cupecoy Bay Villa - 2.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$815.00
from $815.00 / night
Villa Fleur De Cactus | Ocean View # Located in Beautiful Lurin with Private P
Lurin Villa - 19.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,000.00
from $2,000.00 / night
Villa Ushuaia * Ocean Front | Located in Tropical Flamands with Private Pool
Anse des Flamands Villa - 17.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$936.00
from $936.00 / night
Eden Rock Villa Claridge | Ocean View - Located in Exquisite Anse des Cayes wi
Anse des Cayes Villa - 18.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,714.00
from $1,714.00 / night
Villa Vitti # Ocean View ^ Located in Stunning Shell Beach with Private Pool
Gustavia Villa - 19.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$4,571.00
from $4,571.00 / night
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