Updating...

More filters (1)

Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Fax machine
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Clothes dryer
Games room
Table tennis
Pool or snooker table
Shared outdoor pool (unheated)
Swing set or jungle gym
Video player
Freezer
Stereo system
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
Microwave
Boat available
Linen provided
Towels provided
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

See all

Less

Parking
Car not required
Children under 5
Smoking allowed

Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

See all

Less

Beach or lakeside relaxation
Walking trips
Tennis in town
Water sports

Horse riding
Fishing
Cycling trips
Waterfront
Golf within 30mins drive
Mountain Views

See all

Less

262 villas

Sort by:

COCO BEACH CLUB #5.... Located on the soft white powdery sand of Simpson Bay be

Simpson Bay apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$230

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

1 bedroom
2 bathrooms

sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$258

Studio in Pelican Key Paradise

Simpson Bay apartment

1 bathroom

sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$172

MARISOL... Light and airy townhouse at Point Blue in Pelican Key Estate

Simpson Bay apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$230

COCO BEACH CLUB 6...walk out onto the sand of Simpson Bay Beach

Simpson Bay condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$230

1Bedroom in Pelican Key

Simpson Bay apartment

1 bedroom
1 bathroom

sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$316

IL PUNTO BLUE...Located right on the beach in prestigious Pelican Key

Simpson Bay apartment

3 bedrooms
4 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$430

RENDEZVOUS...A fabulous 2 BR contemporary 2 BR condo unit on a great beach!

Simpson Bay apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$443

Beach Heaven

Simpson Bay penthouse

2 bedrooms
6 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$344

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

2 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$304

ATLANTIS... Beachfront on Simpson Bay - totally redone after Irma!

Simpson Bay apartment

1 bedroom
1 bathroom

sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$273

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Simpson Bay apartment

2 bedrooms
3 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$509

Beach view

Simpson Bay apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$569

Encanto -2 Bedroom Beachfront Condo in Simpson Bay, Sint Maarten -GORGEOUS VIEW!

Simpson Bay apartment

2 bedrooms
2 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$286

ROYAL PALM BEACH #101 ... 3 BR beachfront resort! Close to restaurants & shoppi

Simpson Bay condo

3 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$358

THE GREAT ESCAPE... Rare 3BR Beachfront on Simpson Bay! Perfect for couples!

Simpson Bay condo

3 bedrooms
3 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$626

Beautiful 1-bedroom rental apartment in Simpson Bay

Simpson Bay apartment

1 bedroom
1 bathroom

sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$316

Caribbean Breeze SXM

Simpson Bay condo

2 bedrooms
3 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$316

Atrium Beach Resort and Spa 2BR

Simpson Bay condo

2 bedrooms
2 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$206

Beachfront Retreat. Newly renovated modern apartment on the beach side

Simpson Bay apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$299

COCO BEACH HOUSE... Charming refurbished 2BR on Simpson Bay Beach

Simpson Bay condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$391

THE DREAM at Los Arenas... 7th Night FREE thru Nov 15! Beachfront on Simpson Bay

Simpson Bay condo

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$483

Great rentals within 20 miles that match your search

3 bedroom Caribbean dream Vacation

Oyster Pond apartment

3 bedrooms
2 bathrooms

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$516

European Luxury Orient Beach Tortola 5318

Orient Bay apartment

1 bedroom
1 bathroom

sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$149

LUXURY STUDIO THE WATERFRONT

Marigot studio

Studio
1 bathroom

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$112

Apartement with fantastic sea view

Marigot apartment

2 bedrooms
1 bathroom

sleeps 6

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$223

safari on the beach

Marigot apartment

1 bedroom
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$172

APARTMENT ANY COMFORT

Oyster Pond apartment

1 bedroom
1 bathroom

sleeps 3

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$155

Duplex Creole Nettle Bay view and pool

Baie Nettle apartment

1 bedroom
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$149

Suite 6/8 pers au Westin Dawn Beach ST Marteen

Oyster Pond hotel apartment

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$530

Dawn Beach Club

Oyster Pond condo

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$655

The Westin Dawn Beach Spa and Resort

Oyster Pond condo

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$435

Dawn Beach Resort, Westin Penthouse for 8 Guests!

Oyster Pond penthouse

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$491

Mount Vernon Villas

Cul de Sac apartment

2 bedrooms
3 bathrooms

sleeps 5

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$299

CARIBBEAN PARADISE... Affordable 2BR condo at Rainbow Beach Club on the shores o

Cupecoy Bay apartment

2 bedrooms
2 bathrooms

sleeps 4

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$181

Loue appartement de luxe 6/8 personnes(DBC) refait à neuf .Balcon vue mer.

Oyster Pond apartment

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$574

Suite 5* 3 BD 2 BA Westin Dawn Beach Sint Maarten res. saturday to saturday

Oyster Pond apartment

3 bedrooms
2 bathrooms

sleeps 8

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$867

SKI BEACH CONDO... romantic beach front condo on Nettle Bay beach

Baie Nettle apartment

1 bedroom
1 bathroom

sleeps 2

Match: Shared outdoor pool (unheated)

All filters match

Price per night from

$171

Viewing 38 of 262
rentals in Simpson Bay

Also consider

Oyster Pond 67 properties
Cupecoy Bay 53 properties
Philipsburg 46 properties
Maho 17 properties
Cole Bay 8 properties
Pelican Key 6 properties
Dawn Beach 5 properties
Little Bay 5 properties
Sint Maarten 282 properties
Dominican Republic 4,636 properties
Jamaica 2,105 properties
Martinique 1,057 properties
Barbados 954 properties
Puerto Rico 857 properties
St. Martin Sint Maarten 778 properties
St. Barthelemy 775 properties
Bahamas 636 properties
St. Lucia 504 properties
Aruba 458 properties
US Virgin Isles 422 properties
Curacao 329 properties
Antigua and Barbuda 180 properties
Cayman Islands 178 properties
Dominica 175 properties
St. Vincent and the Grenadines 118 properties
Bonaire 119 properties
Anguilla 71 properties
Haiti 43 properties
Bermuda 35 properties
Montserrat 23 properties
Saba 6 properties

Vacation Rentals & Villas in Simpson Bay

Per night

262 villas

Viewing 38 of 262rentals in Simpson Bay

Also consider

Viewing 38 of 262
rentals in Simpson Bay