Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 585 Rentals Available.
585 Vacation rentals
Filters applied: 2+ Bedrooms
Paradise Found at Las Arenas - Beachfront Luxury!
Simpson Bay Apartment
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Responds fast! Avg. 1 hour 58 minutes
$409.00
from $409.00 / night
Contemporary penthouse at La Brisas
Simpson Bay Apartment
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$586.00
from $586.00 / 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
$850.00
from $850.00 / night
Spellbound Too Catamaran *Fully-Crewed & All-Inclusive*
Simpson Bay Yacht
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 1 night min
- Ask about children
- Ask about pets
$2,000.00
from $2,000.00 / night
Villa Speranza | Near Ocean - Located in Fabulous Simpson Bay with Private Poo
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$598.00
from $598.00 / night
Villa Amaryllis | Waterfront - Located in Stunning Simpson Bay with Private Po
Simpson Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$747.00
from $747.00 / night
Your search has been expanded 19.7 miles to include more rentals
Modern 2 bedrooms apartment at 50 meters from the beach
Orient Bay Apartment - 6.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 42 minutes
$163.00
from $163.00 / night
La Casita Villa - Oceanfront Vacation Rental
St Martin / St Maarten Villa - 1.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.32 mi
- Swimming pool
$428.00
from $428.00 / night
Champagne Shores
Blowing Point House - 9.2 miles away
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 1 night min
- Swimming pool
- Ask about children
- Air conditioning
$1,700.00
from $1,700.00 / 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
$638.00
from $638.00 / night
NEW SANDCASTLE BEACH HOUSE + Jeep Wrangler + Pool & Jacuzzi
The Valley Villa - 13.5 miles away
- 3 bedrooms 3
- 5 bathrooms
- sleeps 6 6
- min stay varies
- Air conditioning
- Pet friendly
- Private garden
Responds fast! Avg. 1 hour 5 minutes
$1,432.00
from $1,432.00 / night
Sandcastle Villa - 10,000 sf Luxury Beachfront Villa + Chevy Tahoe (by owner)
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 6 bathrooms
- sleeps 10 10
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 5 minutes
$2,176.00
from $2,176.00 / night
Luxury Villa with private heated pool and AC in all bedrooms
St Martin / St Maarten Villa - 5.5 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$491.00
from $491.00 / night
Villa Casa Sunshine - 10 Suites
Philipsburg House - 5 miles away
- 10 bedrooms 10
- 10 bathrooms
- sleeps 20 20
- 5 nights min
- Swimming pool
- Ask about children
- Ask about pets
$2,550.00
from $2,550.00 / night
Villa Rosa *Dawn Beach*
Philipsburg House - 5.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Ask about children
- Ask about pets
$407.00
from $407.00 / night
Villa Blanco - Dawn Beach
Philipsburg House - 5.2 miles away
- 2 bedrooms 2
- 3 bathrooms
- sleeps 4 4
- 5 nights min
- Ask about children
- Ask about pets
$393.00
from $393.00 / night
Dawn Beach Estates - Atlantica Beach Club Condo - Unit 4
Philipsburg Apartment - 5.3 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$268.00
from $268.00 / night
$743.00
from $743.00 / night
Dream Island Views of Orient Bay - 4 Suites / Sleeps 8
Orient Bay House - 6.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$836.00
from $836.00 / night
$366.00
from $366.00 / night
10% OFF Special - Villa Belle Vue - Orient Bay
Orient Bay House - 5.5 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$836.00
from $836.00 / night
Oyster Bay Beach Club - Lighthouse Condo 2B - Newly Renovated - 3 bdrms
Oyster Pond Apartment - 5.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$585.00
from $585.00 / night
Spinnaker Condo - Unit 1312 *Oyster Pond*
Oyster Pond Apartment - 5.5 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 3 nights min
- Swimming pool
- Ask about children
- Ask about pets
$229.00
from $229.00 / night
Oyster Bay Beach Club - Lighthouse Condo - Unit 3A
Oyster Pond Apartment - 5.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 3 nights min
- Swimming pool
- Ask about children
- Air conditioning
$585.00
from $585.00 / night
The Palm trees
Anse des Cayes Villa - 19 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
$714.00
from $714.00 / night
Brown Rock
Anse des Cayes Villa - 18.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
$571.00
from $571.00 / night
Listen to the waves
St. Barthelemy Villa - 17.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
$571.00
from $571.00 / night
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