Simpson Bay 4+ bedroom Villas, Vacation Rentals & More - 29 Rentals Available.
29 Vacation rentals
Filters applied: 4+ Bedrooms
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
$858
from $858 / 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
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
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
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
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
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 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
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
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
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
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
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 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
$658
from $658 / night
Villa La Di Da 4 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643
from $643 / 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
Villa Amaryllis 4 + 1 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786
from $786 / night
Classy 5 Bedroom Villa in Pelican Bay
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$1429
from $1429 / 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
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
Coral Breeze - STM
Simpson Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- Min stay varies
- Child friendly
$342
from $342 / 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
$1158
from $1158 / night
6 Bedroom Villa with Pool in Pelican Key
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1800
from $1800 / night
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
Villa La Di Da 5 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$750
from $750 / night
Villa Amaryllis 4 + 1 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786
from $786 / night
Ravishing 5 Bedroom Villa in Pelican Bay
Simpson Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$843
from $843 / night
Villa La Di Da 6 Bedroom SPECIAL OFFER
Simpson Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858
from $858 / night
Your search has been expanded 1.1 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
$458
from $458 / night
Villa LaLuna 4 Bedroom SPECIAL OFFER
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 LaLuna 4+1 Bedroom SPECIAL OFFER
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
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
Terrific 5 Bedroom Waterfront Villa in Beacon Hill
St. Maarten-St. Martin Villa - 1.1 miles away
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 12 12
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$1071
from $1071 / night
Villa Sunshine 4 Bedroom SPECIAL OFFER
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 6 Bedroom SPECIAL OFFER
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
Villa Sunshine 5 Bedroom SPECIAL OFFER
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
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
$786
from $786 / 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
$458
from $458 / night
Exceptional 5 Bedroom Villa with Private Pool in Pelican Bay
Cole Bay Villa - 1.1 miles away
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- 4 nights min
- Swimming pool
- Ask about children
- Air conditioning
$1701
from $1701 / night
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