Simpson Bay 3-bedroom Villas, Vacation Rentals & More - 976 Rentals Available.
976 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
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
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
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
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
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
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
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
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
$455.00
from $455.00 / 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
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
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
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
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
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
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
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
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
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
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
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 19.7 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
$343.00
from $343.00 / 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
$557.00
from $557.00 / night
Apartment Florence
Cupecoy Bay Apartment - 2.4 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
$296.00
from $296.00 / night
Villa Robert
Colombier Villa - 17.5 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$141.00
from $141.00 / night
Villa Clooney
Gustavia Villa - 19.2 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$143.00
from $143.00 / night
Villa Stanley
Gustavia Villa - 19.5 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,414.00
from $1,414.00 / night
Villa Malone
St. Jean Villa - 19.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
$141.00
from $141.00 / night
Villa Cecile
Terres Basses Villa - 3.4 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
$444.00
from $444.00 / night
Villa Speedman
Anse des Flamands Villa - 17.8 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Air conditioning
$143.00
from $143.00 / night
Villa Mars
Terres Basses Villa - 2.9 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
- Child friendly
$444.00
from $444.00 / night
Villa Demetrius
Terres Basses Villa - 3.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 5 nights min
- Swimming pool
$148.00
from $148.00 / night
Villa Hopkins
Lurin Villa - 19.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
$1,386.00
from $1,386.00 / night
Villa Russell
Anse des Cayes Villa - 18.8 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,429.00
from $1,429.00 / night
Villa Depp
Lurin Villa - 19.7 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$143.00
from $143.00 / night
Villa Sheldon
Anse des Flamands Villa - 18.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
$1,400.00
from $1,400.00 / night
Villa Saget
Anse des Flamands Villa - 18.3 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,414.00
from $1,414.00 / night
Villa Chateau de Versailles
Terres Basses Villa - 3.6 miles away
- 9 bedrooms 9
- 11 bathrooms
- sleeps 18 18
- 5 nights min
- Swimming pool
- Child friendly
$4,437.00
from $4,437.00 / night
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