Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 26 Rentals Available.
26 Vacation rentals
Filters applied: 4+ Bedrooms
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
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
$787
from $787 / 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
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
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
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
Villa Hardman
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
$142
from $142 / 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
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
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 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
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
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
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
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
SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to
Simpson Bay House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Child friendly
- Air conditioning
$429
from $429 / 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
Coral Breeze - STM
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
$343
from $343 / 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
$1196
from $1196 / 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 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 4 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Child friendly
$643
from $643 / 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
$787
from $787 / night
Diamond Chateau at Cole Bay, Saint Maarten - Ocean View, Pool, Private
Simpson Bay Villa
- 5 bedrooms 5
- 7 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Ask about pets
Inquire for Rates
Pricing unknown
LaLuna at Beacon Hill Road, Simpson Bay - Beach Front, Pool
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$700
from $700 / night
Your search has been expanded 1.3 miles to include more rentals
TARA...large affordable oceanfront villa, walk to beach
St. Maarten-St. Martin Villa - 1 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$459
from $459 / night
Villa LaLuna 4 Bedroom
St. Maarten-St. Martin Villa - 1.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
$650
from $650 / night
Villa LaLuna 4+1 Bedroom
St. Maarten-St. Martin Villa - 1.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
$700
from $700 / night
LA LUNA VILLA... 5BR Beach Front Villa in Beacon Hill, St Maarten
St. Maarten-St. Martin Villa - 1.1 miles away
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$600
from $600 / night
Villa Sunshine 4 Bedroom
St. Maarten-St. Martin Villa - 1.1 miles away
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$650
from $650 / night
Villa Sunshine 5 Bedroom
St. Maarten-St. Martin Villa - 1.1 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$700
from $700 / night
Villa Sunshine 6 Bedroom
St. Maarten-St. Martin Villa - 1.1 miles away
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1500
from $1500 / night
Amaryllis - Simpson Bay Lagoon, St. Maarten
Cole Bay Villa - 1.1 miles away
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Ask about children
- Ask about pets
$787
from $787 / night
BELLE AMOUR...5BR fall in love again! Breathtaking sunsets right on the ocean...
St. Maarten-St. Martin Villa - 1.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$459
from $459 / night
Villa Bella Vita at Pelican Key, Saint Maarten - Ocean View, Media Room, Pool
Cole Bay Villa - 1.1 miles away
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1500
from $1500 / night
DIAMOND CHATEAU...5BR estate, gorgeous views! total privacy, convenient location
St. Maarten-St. Martin Villa - 1.1 miles away
- 5 bedrooms 5
- 7 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$593
from $593 / night
CORAL BREEZE...Large affordable beachfront villa! Bring the whole family!
St. Maarten-St. Martin House - 1.2 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$343
from $343 / night
Villa Diamond Chateau *Simpson Bay*
Bellevue House - 1.3 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 3 nights min
- Swimming pool
- Child friendly
$343
from $343 / night
Villa Balaclava - Pelican
Cole Bay House - 1.3 miles away
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 3 nights min
- Ask about children
$500
from $500 / night
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