Simpson Bay Villas & Vacation Rentals - 1058 Rentals Available
1,058 Vacation rentals
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
- 7 nights min
- 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
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 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
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
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
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
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
Beautiful 5 bedroom contemporary villa
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1,143.00
from $1,143.00 / night
Beautiful beachfront 5 bedroom villa
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 5 nights min
- 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
- 5 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
$400.00
from $400.00 / 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
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
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
Villa Amaryllis - Waterfront * Located in Magnificent Simpson Bay with Private
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$736.00
from $736.00 / 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
ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!
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 Fabulous Simpson Bay with Private Po
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$675.00
from $675.00 / 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
Villa Amaryllis ^ Waterfront :: Located in Wonderful Simpson Bay with Private
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$825.00
from $825.00 / 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
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
COLONY MANOR GUEST COTTAGE... Romantic hideaway right on Simpson Bay Beach!
Simpson Bay Studio
- Studio -1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Child friendly
- Air conditioning
$300.00
from $300.00 / 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 13.5 miles to include more rentals
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 2 minutes
$92.00
from $92.00 / night
QUIET APPARTMENT with large terrace next to VILLA AT POINT BLANCHE
Philipsburg Apartment - 4.6 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 2 mi
- Swimming pool
$109.00
from $109.00 / night
Your Paradise Villa
Orient Bay Villa - 5.6 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0.5 mi
- Swimming pool
Responds fast! Avg. 1 hour 51 minutes
$638.00
from $638.00 / 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
SANDCASTLE BEACH HOUSE
The Valley Villa - 13.5 miles away
- 3 bedrooms 3
- 5 bathrooms
- sleeps 6 6
- min stay varies
- Air conditioning
- Pet friendly
- Private garden
$1,250.00
from $1,250.00 / night
Studio Mont Vernon 4 Stars on Orient Beach
Orient Bay Condo - 6.3 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$84.00
from $84.00 / night
Modern 2 bedrooms apartment at 50 meters from the beach
Orient Bay Apartment - 6.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 1 hour 2 minutes
$170.00
from $170.00 / night
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