Simpson Bay 3-bedroom Villas, Vacation Rentals & More - 719 Rentals Available.
719 Vacation rentals
Filters applied: 3+ Bedrooms
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Your search has been expanded 19.9 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
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 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
5% Off Three Day's Only. | Ocean View # Located in Wonderful Terres Basses with
Terres Basses Villa - 3.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$715.00
from $715.00 / night
Bird of Paradise Villa
Anguilla Villa - 12.6 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Ask about pets
Responds fast! Avg. 1 hour 5 minutes
$2,000.00
from $2,000.00 / night
Villa Bakea * Ocean View * Located in Exquisite Anse des Cayes with Private Po
Anse des Cayes Villa - 18.8 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,143.00
from $2,143.00 / night
Villa Kir Royal # Near Ocean | Located in Magnificent Saint Jean with Private
St. Jean Villa - 19.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$929.00
from $929.00 / night
Villa La Pointe | Near Ocean :: Located in Fabulous Gustavia with Private Pool
Gustavia Villa - 19.1 miles away
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,857.00
from $2,857.00 / night
Villa Casa Branca :: Ocean View ^ Located in Beautiful Anse Marcel with Private
Anse Marcel Villa - 6.2 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$400.00
from $400.00 / night
Villa Kuban :: Ocean View | Located in Stunning Colombier with Private Pool
Anse des Flamands Villa - 18.2 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,200.00
from $1,200.00 / night
Beachfront World-Class Luxury Estate - 10 Suites / Sleeps 20
Philipsburg House - 5 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 20 20
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$1,193.00
from $1,193.00 / 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
Airport Transfer Included At Elegant Villa Amancaya - Ocean View :: Located in
Anse des Cayes Villa - 18.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,286.00
from $3,286.00 / night
Villa Bakea :: Ocean View | Located in Wonderful Anse des Cayes with Private P
Anse des Cayes Villa - 18.8 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,857.00
from $1,857.00 / night
Ocean Five
Anse des Flamands Villa - 18 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Ask about pets
Responds fast! Avg. 1 hour 5 minutes
$1,143.00
from $1,143.00 / night
Beachcourt Villa
Island Harbour Villa - 15.2 miles away
- 4 bedrooms 4
- 8 bathrooms
- sleeps 8 8
- min stay varies
- Ask about children
- Ask about pets
Responds fast! Avg. 1 hour 5 minutes
$1,400.00
from $1,400.00 / night
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