Simpson Bay Villa Rentals - 42 Rentals Available.
42 Vacation rentals
Filters applied: Villa
$458
from $458 / night
Sunshine at Beacon Hill, St. Maarten - Beachfront, Pool
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
$1500
from $1500 / night
Aqualina 102
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
- Ask about pets
$314
from $314 / night
Villa Hardman
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
$142
from $142 / 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
$1205
from $1205 / night
BELLA VITA... a gorgeous, 7BR super deluxe... views galore
Simpson Bay Villa
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1200
from $1200 / night
Daffodil at Pelican Key, Saint Maarten - Beachfront, Gated Community, Pool
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1071
from $1071 / night
Villa Tara at Beacon Hill, Saint Maarten - Oceanfront & Pool
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$657
from $657 / night
Villa Amaryllis 4 + 1 Bedroom
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786
from $786 / night
Summer Hill in Pelican Key, Saint Maarten - Gated, private pool
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$614
from $614 / night
SAPPHIRE... a casual hillside 3 BR villa, St Maarten villa with ocean views in
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$358
from $358 / night
Faja Lobie at Beacon Hill, Saint Maarten - Beachfront & Pool
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$412
from $412 / night
Witenblauw Estate at Pelican Key, Saint Maarten - Directly On The Beach
Simpson Bay Villa
- 6 bedrooms 6
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1800
from $1800 / night
LA DI DA...St Maarten villa high atop a mountain at the mouth of Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500
from $500 / night
Coco Beach Duplex
Simpson Bay Villa
- 2 bedrooms 2
- 3 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
$229
from $229 / night
ST TROPEZ... amazing views of Heineken Regatta from this beautiful villa in
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$500
from $500 / night
Caribbean Blue at Pelican Key, Saint Maarten - Beachfront, Amazing Sunset View
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$843
from $843 / 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
$1800
from $1800 / night
PROVENCE... affordable 6BR villa w/ gorgeous views, close to lots of dining
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$572
from $572 / night
Provence at Pelican Key, Saint Maarten - Ocean View, Pool, Lovely Outdoor
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$643
from $643 / night
The Reef at Simpson Bay, Saint Maarten - Private Pool, Ocean Views, Modern
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$1143
from $1143 / 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
$643
from $643 / night
RIVIERA... 3 BR hillside villa in Pelican Key, St Maarten
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$358
from $358 / night
Villa La-Di-Da at Pelican Key, Saint Maarten - Spectacular Ocean View, Infinity
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$857
from $857 / night
Coral Breeze - STM
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
$342
from $342 / night
Villa La Di Da 4 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
$643
from $643 / night
SMART VILLA...nestled beachfront at Pelican Key
Simpson Bay Villa
- 3 bedrooms 3
- 4 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
- Air conditioning
$258
from $258 / night
La Perla Estate at Terres Basses, Saint Maarten - Oceanfront, Luxury, Private
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
Inquire for Rates
Pricing unknown
Villa Amaryllis 3 Bedroom
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / night
Tropical Paradise Villa at Coral Shores in Pelican
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- 5 nights min
$234
from $234 / night
Villa La Di Da 5 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
$750
from $750 / night
Villa La Di Da 3 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Child friendly
$571
from $571 / night
Villa La Di Da 6 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
$857
from $857 / night
Villa Hope
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$629
from $629 / night
Villa La Di Da 2 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Child friendly
$500
from $500 / night
Villa Amaryllis 3 Bedroom
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / night
Villa Amaryllis 4 + 1 Bedroom
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786
from $786 / night
Villa Amaryllis 2 Bedroom
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / night
Villa Hope
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$629
from $629 / night
Villa Amaryllis 2 Bedroom
Simpson Bay Villa
- 2 bedrooms 2
- 2 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / night
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