Simpson Bay Villas & Vacation Rentals with Swimming Pool - 836 Rentals Available.
836 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
$409.00
from $409.00 / 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
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
$843.00
from $843.00 / 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
$401.00
from $401.00 / 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
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
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
- Child friendly
- 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
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
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
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
$3,001.00
from $3,001.00 / 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
$401.00
from $401.00 / 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
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
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
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos
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
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
$401.00
from $401.00 / 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
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
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
$675.00
from $675.00 / 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
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
$735.00
from $735.00 / night
CARIBBEAN SUN... Charming Beachfront Condo on Simpson Bay, Fully Redone after Ir
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
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 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
ATLANTIS... 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
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
$825.00
from $825.00 / 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
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
$1,200.00
from $1,200.00 / night
BEACON BUNGALOW... Charming, affordable, modern 2BR oceanfront dollhouse!
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
BELLE AMOUR... 5BR fall in love again! Breathtaking sunsets right on the ocean..
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
Your search has been expanded 18.3 miles to include more rentals
La Casita Villa - Oceanfront Vacation Rental
St Martin / St Maarten Villa - 1.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0.32 mi
- Swimming pool
$393.00
from $393.00 / night
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
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$357.00
from $357.00 / night
Sea view studio by the sea
Orient Bay Studio - 6.3 miles away
- Studio -1
- 1 bathroom
- sleeps 4 4
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 4 minutes
$98.00
from $98.00 / night
Sandcastle Villa - Luxury Beachfront (owner)
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 10 10
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$1,900.00
from $1,900.00 / night
THE PALMS CASTLE ... Consider Yourself Royalty
Terres Basses Villa - 3.6 miles away
- 9 bedrooms 9
- 10 bathrooms
- sleeps 18 18
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$10,572.00
from $10,572.00 / night
Villa Ocean's 5 (2 bedrooms)
Anse des Flamands Villa - 18.3 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
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