Simpson Bay 2-bedroom Villas, Vacation Rentals & More - 695 Rentals Available.
695 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. 2 hours 30 minutes
$409.00
from $409.00 / night
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
COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$415.00
from $415.00 / night
Burgeoux Villa... Comfortable Beach front home, walk to Maho or Simpson Bay bea
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$758.00
from $758.00 / 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
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
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
- Air conditioning
$672.00
from $672.00 / 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
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
MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$329.00
from $329.00 / 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
RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / 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
PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos
Simpson Bay Villa
- 6 bedrooms 6
- 5 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,386.00
from $1,386.00 / night
SEA BEACH TREASURE... Gorgeous 2BR Penthouse on Simpson Bay Beach, St Maarten
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$465.00
from $465.00 / night
ST TROPEZ... amazing views of the Caribbean Sea from this lovely villa in Pelica
Simpson Bay Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$729.00
from $729.00 / night
Spellbound Too Catamaran *Fully-Crewed & All-Inclusive*
Simpson Bay Yacht
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- 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
$748.00
from $748.00 / night
UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!
Simpson Bay Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$519.00
from $519.00 / night
LA PLAGE PENTHOUSE....3BR suite in Royal Islander Resort...walk to restaurants,
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
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
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
$850.00
from $850.00 / night
Your search has been expanded 19.7 miles to include more rentals
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
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
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$491.00
from $491.00 / 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. 58 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. 58 minutes
$2,176.00
from $2,176.00 / 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
PORT CARAIBES 74... Cosy 2nd floor condo in quiet, tropical area with gorgeous
Cul de Sac Apartment - 6.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$189.00
from $189.00 / night
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. 48 minutes
$176.00
from $176.00 / night
Villa Hurakan | Ocean Front - Located in Magnificent Colombier with Private Po
Anse des Flamands Villa - 18.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$577.00
from $577.00 / night
Villa Cascades | Ocean View - Located in Exquisite Terres Basses with Private
Terres Basses Villa - 3.5 miles away
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$950.00
from $950.00 / night
Villa Ylang Ylang | Ocean View - Located in Beautiful Flamands with Private Po
Anse des Flamands Villa - 18.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$493.00
from $493.00 / night
Villa La Pinta | Near Ocean - Located in Fabulous Terres Basses with Private P
Terres Basses Villa - 3.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$516.00
from $516.00 / night
Villa Happy Bay | Beach View - Located in Magnificent Happy Bay with Private P
La Savane Villa - 4.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$665.00
from $665.00 / night
Villa SandCastle | Beach Front - Located in Fabulous Limestone Bay with Privat
The Valley Villa - 13.5 miles away
- 4 bedrooms 4
- 5 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,805.00
from $1,805.00 / night
Villa Globe Trotter | Ocean View - Located in Tropical Lurin with Private Pool
Lurin Villa - 19.7 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,900.00
from $1,900.00 / night
Condo Acadia | Ocean Front - Located in Tropical Porto Cupecoy with House Clea
Cupecoy Bay Villa - 2 miles away
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$408.00
from $408.00 / night
Villa Luna | Beach View - Located in Fabulous Cupecoy with Private Pool
Cupecoy Bay Villa - 2.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$475.00
from $475.00 / night
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