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1,734 Houses
2BR-Oceanfront-Royal Palm
Simpson Bay / Simpson Bay Beach
2 6 5 nights min
- 2 bedrooms
- sleeps 6
- 5 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$401
Price per night from
$401
Le Papillon - REOPENED AFTER IRMA - Modern Beachfront Unit with great view
Simpson Bay / Simpson Bay Beach
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 0.01 mi
- Child Friendly
Map
Price per night from
$325
Responds fast!
avg. 1 hour 55 minutes
Price per night from
$325
PELICAN KEY - CHARMING STUDIO WITH OCEAN VIEW
Simpson Bay / Simpson Bay Beach
1 2 4 nights min
- 1 bedroom
- sleeps 2
- 4 nights min
- Beach / lakeside relaxation
- Nearest beach 0.8 mi
- Air conditioning
Map
Price per night from
$121
Responds fast!
avg. 3 hours 41 minutes
Price per night from
$121
Caribbean Sun
Simpson Bay / Simpson Bay Beach
2 4 6 nights min
- 2 bedrooms
- sleeps 4
- 6 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$300
Responds fast!
avg. 2 hours 24 minutes
Price per night from
$300
Pearl on the Beach
Simpson Bay / Simpson Bay Beach
2 4 5 nights min
- 2 bedrooms
- sleeps 4
- 5 nights min
- Beach / lakeside relaxation
- Child Friendly
Map
Price per night from
$516
Price per night from
$516
Barefoot Oceanfront Condo St Maarten
Simpson Bay / Simpson Bay Beach
2 6 4 nights min
- 2 bedrooms
- sleeps 6
- 4 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$305
Price per night from
$305
Beachfront Condo
Simpson Bay / Simpson Bay Beach
2 4 5 nights min
- 2 bedrooms
- sleeps 4
- 5 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$515
Price per night from
$515
Anchorage Apartment
Simpson Bay / Simpson Bay Beach
1 4 min stay varies
- 1 bedroom
- sleeps 4
- min stay varies
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Child Friendly
Map
Price per night from
$160
Responds fast!
avg. 2 hours 17 minutes
Price per night from
$160
Vacation Villa at Simpson's bay and Marina
Simpson Bay / Simpson Bay Beach
1 4 7 nights min
- 1 bedroom
- sleeps 4
- 7 nights min
- Beach / lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
Map
Price per night from
$136
Responds fast!
avg. 1 hour 33 minutes
Price per night from
$136
Beach Heaven
Simpson Bay / Simpson Bay Beach
2 4 1 night min
- 2 bedrooms
- sleeps 4
- 1 night min
- Swimming pool
- Air conditioning
Price per night from
$344
Price per night from
$344
Great rentals within 20 miles that match your search
Distance approx 2.82 km from Simpson Bay Beach Show on Map
Exclusive and private Caribbean Guesthouse
Saint-Martin / Terres Basses
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Nearest beach 2 mi
- Swimming pool
- Child Friendly
Map
Price per night from
$200
Price per night from
$200
Distance approx 5.28 km from Simpson Bay Beach Show on Map
NEW & CENTRAL Apartment on the Grand Case Beach. Pool, Parking. Kind Size Bed.
Saint-Martin / Grand Case
1 4 5 nights min
- 1 bedroom
- sleeps 4
- 5 nights min
- Beach / lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Map
Price per night from
$266
Responds fast!
avg. 2 hours 42 minutes
Price per night from
$266
Distance approx 9.56 km from Simpson Bay Beach Show on Map
Lockrum Point Villa:Ocean front 3-bed/ 3-bath/pool
Anguilla / Little Harbour
3 6 4 nights min
- 3 bedrooms
- sleeps 6
- 4 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$450
Price per night from
$450
Distance approx 15.32 km from Simpson Bay Beach Show on Map
James Place Apartments, Anguilla , British West Indies
Anguilla / Island Harbour
1 2 1 night min
- 1 bedroom
- sleeps 2
- 1 night min
- Beach / lakeside relaxation
- Nearest beach 8 mi
- Child Friendly
Map
Price per night from
$100
Responds fast!
avg. 3 hours 27 minutes
Price per night from
$100
Distance approx 5.47 km from Simpson Bay Beach Show on Map
Dawn Beach Resort, Westin Penthouse for 8 Guests!
Sint Maarten / Oyster Pond
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$428
Price per night from
$428
Distance approx 19.79 km from Simpson Bay Beach Show on Map
Villa Eden Island, 3 bedroom
St. Barthelemy / Gustavia
3 6 5 nights min
- 3 bedrooms
- sleeps 6
- 5 nights min
- Nearest beach 0.5 mi
- Swimming pool
- Ask about children
Map
Price per night from
$857
Price per night from
$857
Distance approx 5.07 km from Simpson Bay Beach Show on Map
Villa Robinson. Breathtaking view!
Sint Maarten / Oyster Pond
3 8 2 nights min
- 3 bedrooms
- sleeps 8
- 2 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$1,032
Price per night from
$1,032
Distance approx 16.73 km from Simpson Bay Beach Show on Map
Ocean View Apartment at Captain's Ridge (view from every room)
Anguilla / Island Harbour
2 4 3 nights min
- 2 bedrooms
- sleeps 4
- 3 nights min
- Nearest beach 3 mi
- Air conditioning
- Private garden
Map
Price per night from
$120
Price per night from
$120
Distance approx 2.43 km from Simpson Bay Beach Show on Map
Modern Blue Residence Condo, Cupecoy, Sint Maarten
Sint Maarten / Philipsburg
2 6 3 nights min
- 2 bedrooms
- sleeps 6
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$450
Responds fast!
avg. 41 minutes
Price per night from
$450
Distance approx 9.8 km from Simpson Bay Beach Show on Map
Gardenia Villa at Indigo Reef
Anguilla / The Valley
1 2 4 nights min
- 1 bedroom
- sleeps 2
- 4 nights min
- Nearest beach 0.9 mi
- Child Friendly
- Pet Friendly
Map
Price per night from
$325
Price per night from
$325
Distance approx 6.42 km from Simpson Bay Beach Show on Map
Emmas Beach Studio 4316
Saint-Martin / Orient Bay
Studio 4 5 nights min
- Studio
- sleeps 4
- 5 nights min
- Beach / lakeside relaxation
- Nearest beach 0 mi
- Swimming pool
Map
Price per night from
$140
Price per night from
$140
Distance approx 5.67 km from Simpson Bay Beach Show on Map
Oyster Bay Beach Resort
Sint Maarten / Philipsburg
1 4 7 nights min
- 1 bedroom
- sleeps 4
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$243
Responds fast!
avg. 2 hours 37 minutes
Price per night from
$243
Distance approx 5.44 km from Simpson Bay Beach Show on Map
Beachfront home featured on HGTV 5 bedrooms, pool
Sint Maarten / Philipsburg
5 20 3 nights min
- 5 bedrooms
- sleeps 20
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 0.25 mi
- Swimming pool
Map
Price per night from
$899
Price per night from
$899
Distance approx 1.38 km from Simpson Bay Beach Show on Map
Villa Blue Lagoon SXM
Sint Maarten / Maho
5 10 7 nights min
- 5 bedrooms
- sleeps 10
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$1,430
Price per night from
$1,430
Distance approx 15.6 km from Simpson Bay Beach Show on Map
Allamanda Beach Club - Ground Floor Deluxe Apartment #1
Anguilla / The Valley
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Swimming pool
- Car not necessary
- Air conditioning
Map
Price per night from
$276
Responds fast!
avg. 2 hours 46 minutes
Price per night from
$276
Distance approx 9.92 km from Simpson Bay Beach Show on Map
Luxurious and Exclusive Beachfront Property
Anguilla / West End Village
9 18 min stay varies
- 9 bedrooms
- sleeps 18
- min stay varies
- Swimming pool
- Air conditioning
Map
Price per night from
$14,286
Responds fast!
avg. 3 minutes
Price per night from
$14,286
Distance approx 1.99 km from Simpson Bay Beach Show on Map
Jacqueline's 3BDR Guest House
Saint-Martin / Marigot
3 9 3 nights min
- 3 bedrooms
- sleeps 9
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$148
Responds fast!
avg. 3 hours 11 minutes
Price per night from
$148
Distance approx 15.6 km from Simpson Bay Beach Show on Map
Allamanda Beach Club - 2nd Floor Deluxe Queen #1
Anguilla / The Valley
1 4 2 nights min
- 1 bedroom
- sleeps 4
- 2 nights min
- Swimming pool
- Car not necessary
- Air conditioning
Map
Price per night from
$297
Responds fast!
avg. 2 hours 46 minutes
Price per night from
$297
Distance approx 9.67 km from Simpson Bay Beach Show on Map
Anguilla Bow Green Villa on Rendezvous Bay Beach
Anguilla / West End Village
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$1,093
Price per night from
$1,093
Distance approx 1 km from Simpson Bay Beach Show on Map
Oceanfront Townhouse in Pelican Key
Sint Maarten / Philipsburg
3 6 5 nights min
- 3 bedrooms
- sleeps 6
- 5 nights min
- Child Friendly
- Air conditioning
Map
Price per night from
$295
Price per night from
$295
Distance approx 9.43 km from Simpson Bay Beach Show on Map
AVALON BEACHFRONT VILLA
Anguilla / Little Harbour
4 10 2 nights min
- 4 bedrooms
- sleeps 10
- 2 nights min
- Beach / lakeside relaxation
- Suitable for children age 5+
- Air conditioning
Map
Price per night from
$1,200
Responds fast!
avg. 1 hour 49 minutes
Price per night from
$1,200
Distance approx 15.09 km from Simpson Bay Beach Show on Map
CATALINA VILLA AT SHOAL BAY EAST
Anguilla / Island Harbour
2 5 4 nights min
- 2 bedrooms
- sleeps 5
- 4 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$149
Responds fast!
avg. 1 hour 49 minutes
Price per night from
$149
Distance approx 5.43 km from Simpson Bay Beach Show on Map
COME SPEND HOLIDAY SUPER FACING THE SEA
Sint Maarten / Oyster Pond
3 8 7 nights min
- 3 bedrooms
- sleeps 8
- 7 nights min
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Price per night from
$491
Price per night from
$491
Distance approx 1.71 km from Simpson Bay Beach Show on Map
Studio private beach in Marigot
Saint-Martin / Marigot
1 2 3 nights min
- 1 bedroom
- sleeps 2
- 3 nights min
- Child Friendly
Map
Price per night from
$69
Responds fast!
avg. 1 hour 30 minutes
Price per night from
$69
Distance approx 5.7 km from Simpson Bay Beach Show on Map
EDEN ROCK beautiful villa with stunning views
Saint-Martin / Oyster Pond
5 10 7 nights min
- 5 bedrooms
- sleeps 10
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$717
Responds fast!
avg. 2 hours 8 minutes
Price per night from
$717
Distance approx 5.71 km from Simpson Bay Beach Show on Map
Beautiful apartment on St Martin
Sint Maarten / Oyster Pond
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Beach / lakeside relaxation
- Swimming pool
- Child Friendly
Map
Distance approx 5.92 km from Simpson Bay Beach Show on Map
Eve Paradise Villa - Orient Bay - St Martin French Antilles
Saint-Martin / Marigot
4 8 5 nights min
- 4 bedrooms
- sleeps 8
- 5 nights min
- Child Friendly
Map
Price per night from
$424
Price per night from
$424
Distance approx 18.43 km from Simpson Bay Beach Show on Map
Villa Datcha
St. Barthelemy / Anse des Flamands
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Nearest beach 1 mi
- Swimming pool
- Air conditioning
Map
Price per night from
$866
Responds fast!
avg. 2 hours 9 minutes
Price per night from
$866
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