This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Simpson Bay Vacation Rentals Show this location only Back to top
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Affordable Luxury~Sea Belle Villa~ Oceanfront with Pool
1BR/1BA
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Sleeps 1-2
– Simpson Bay #137398
$175 - $325 per night 5-7 night min stay
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Simpson Bay Oceanfront with Pool~ Private 2nd Fl ~Rent as 1 or 2 BR
2BR/2BA
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Sleeps 2-4
– Simpson Bay #110671
$195 - $375 per night 5-7 night min stay
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Bella Mare! Beach Front, Ground Floor & Luxurious
2BR/2BA
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Sleeps 2-5
– Simpson Bay #87855
From $229 per night
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5 Star/Flexible Wks/Fab Water Sports/Beachfrontresort.
2BR+/2BA
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Sleeps 8
– Simpson Bay #188078
$350 per night 4 night min stay
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Beachfront, Ground Floor, Affordable...Crystal Clear Water
1BR+/1BA
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Sleeps 2-3
– Simpson Bay #66671
$169 - $249 per night 5-7 night min stay
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Number 1 Rented Oceanfront Home on Sxm-Private-on the Water
4BR+/5BA
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Sleeps 2-12
– Simpson Bay #49189
$1995- $3995/wk
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Paradise Found, Luxurious 1or2 Bedroom Beachfront Condo in Simpson Bay
2BR/2.5BA
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Sleeps 4
– Simpson Bay #392981
$2100 - $3325 per week 7 night min stay
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Beach Front Ground Floor Luxury, 2 Bedroom Condo
2BR+/2BA
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Sleeps 4-5
– Simpson Bay #212403
$214 - $314 per night 5 night min stay
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Mary's Boon Beach Resort and Condo Hotel - Deluxe 1 Bedroom!
1BR+/1BA
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Sleeps 1-4
– Simpson Bay #153028
$165- $295/nt
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Luxury Beachfront Penthouse Ideal for Couple's Romantic Getaway 1BR/1.5BA – Sleeps 2 – Simpson Bay #446423
Special offer Special Discount offered 5/14-5/30/13 & 9/10-9/29/13
May 14, 2013 to May 30, 2013
$350 - $700 per night 5-10 night min stay -
The Sandpiper.....Elegant & Beachfront
2BR/2.5BA
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Sleeps 4
– Simpson Bay #365157
From $228 p/n
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Beautiful, New & Beachfront 2-Bedroom ....'Island Mermaid'
2BR/2BA
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Sleeps 4
– Simpson Bay #340284
From $1800/wk
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Beach Front Elegance....Sandpiper Suites with Virtual Tour !
2BR/2.5BA
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Sleeps 2-4
– Simpson Bay #375959
From $228 / nt
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Beachfront, Ground Floor....Luxury at it's Best
1BR/2BA
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Sleeps 2
– Simpson Bay #450377
From $243 per night
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Luxury Beachfront Two Bedroom Caribbean Condo in 5-Star Resort
2BR+/2BA
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Sleeps 4-6
– Simpson Bay #80463
$200 - $300 per night 4-7 night min stay
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Beachfront & More....for Less
1BR+/1BA
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Sleeps 2-4
– Simpson Bay #143206
$169 - $249 per night 5-7 night min stay
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New Luxury Condo ** Welcome to the Heart of it All!
2BR/2BA
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Sleeps 4
– Simpson Bay #352725
From $1100/wk
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Sea View @ La Siesta, St. Maarten, N.a.
2BR/2BA
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Sleeps 4
– Simpson Bay #339989
$2800/wk
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Luxurious Beachfront 2 BR Caribbean Condo in 5-Star Resort
2BR/2BA
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Sleeps 2-4
– Simpson Bay #256530
$195- $300/nt
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Condominiums on Beach
2BR+/2BA
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Sleeps 4-6
– Simpson Bay #2544
$1350- $2350/wk
- Casa Carib, Luxury 2 Bedroom / 2 Bath on Simpson Bay Beach 2BR/2BA – Sleeps 4 – Simpson Bay #233071ha
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Luxury Beachfront 2 Bedroom Caribbean Condo in 5-Star Resort
2BR+/2BA
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Sleeps 4
– Simpson Bay #197829
$175- $285/nt US Dollars or PAYPAL
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Elegant Beachfront Villa with Virtual Tour
2BR/2.5BA
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Sleeps 2-4
– Simpson Bay #153538
$1,600 per week
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Luxury Beachfront Villa! Step Off Deck on to Simpson Bay Beach
2BR/2.5BA
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Sleeps 2-4
– Simpson Bay #329528
$250- $440/nt
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Beachfront Elegance W/ Private Jacuzzi Hot Tub on Deck
2BR/2BA
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Sleeps 4
– Simpson Bay #476090
From $414 per night
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Beachfront 2 Bedroom at 5 Star Royal Palm! Oceanfront Villa!
2BR+/2BA
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Sleeps 6
– Simpson Bay #403202
$195 nt
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Lovely Beach Front 2 Bedroom Condo in 5-Star Resort
2BR/2BA
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Sleeps 4
– Simpson Bay #355521
$150 - $250 a night. PAYPAL Available.
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Beachfront Condo in Beautiful Simpson Bay, St. Maarten
2BR+/2.5BA
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Sleeps 4-6
– Simpson Bay #315784
From $1500/wk - $4000/mo
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Simpson Beach Apartment on the Caribbean Sea
2BR/2BA
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Sleeps 4-5
– Simpson Bay #217201
From $215/nt US Dollars
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Fantastic View Beach Front Condo. Caribbean Sun
2BR/2.5BA
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Sleeps 4
– Simpson Bay #88462
$1200- $2400/wk
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Beach Heaven at La Siesta-for the Vacation of Your Dreams!
2BR/2.5BA
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Sleeps 4
– Simpson Bay #114615
$225-$450/nt - $1575-$3150/wk
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Beach on a Budget
1BR+/1BA
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Sleeps 2-4
– Simpson Bay #431843
$169 per night
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The Penthouse at La Siesta - Newly Constructed 3BR/3BA Condo
3BR+/3BA
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Sleeps 6-8
– Simpson Bay #154992
$300-$550/nt - $2100-$3850/wk
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"Barefoot" Beachfront Luxury Ground Floor
2BR+/2BA
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Sleeps 4-6
– Simpson Bay #10669
$280 - $400 per night 5-7 night min stay
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"Coco Belle" 1 Bedroom Beachfront
1BR/1BA
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Sleeps 2
– Simpson Bay #164059
$275 - $360 per night 5-7 night min stay
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Condos on Beach
1BR/1BA
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Sleeps 2
– Simpson Bay #24286
From $1200/wk
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Luxurious Villa Vittoria ~ Private Beach. *Discounted Rates Available for Summer
6BR/5BA
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Sleeps 6-12
– Simpson Bay #443987
$7800 per week 7 night min stay
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5 Star Resort, Simpson Bay Resort Villas
2BR+/2BA
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Sleeps 6
– Simpson Bay #272855
1000- 2400/wk
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St.Maarten Dream Vacation Spot
2BR/2BA
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Sleeps 6
– Simpson Bay #3514671ha
$240 - $320 per night 2-3 night min stay
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Beach Front Ocean Villa, Modern 2 Bedroom Loft, 2.5 Baths
2BR+/2.5BA
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Sleeps 4
– Simpson Bay #339111
$275 per night 5 night min stay
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Hgtv Villa with Beautiful View
5BR/4.5BA
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Sleeps 11-14
– Simpson Bay #448264
$465 per night 3 night min stay
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Flamingo Beach Resort - Click “Book Now” to Securely Book Online
Studio/1BA
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Sleeps 4
– Simpson Bay #3493461ha
$100 - $259 per night 2 night min stay
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Simpson Bay Resort & Marina: All Weeks, Best Prices! Beachfront Resort
Studio/0BA
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Sleeps 6
– Simpson Bay #463855
$1750 per week 7 night min stay
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St. Maarten Escape
3BR/2.5BA
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Sleeps 6
– Simpson Bay #202967
$2500- $4000/wk
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One Bedroom, One and a Half Bath Beachfront Condominium
1BR/1BA
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Sleeps 2
– Simpson Bay #398724
$1500 - $2100/wk
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Beachfront Condo with Pool 1 Bdrm 1 1/2 Baths
1BR/1.5BA
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Sleeps 2
– Simpson Bay #404485
$160- 300/nt
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2BR+/3BA
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Sleeps 4
– Simpson Bay #952358a
$357 - $483 per night
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Studio+/1BA
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Sleeps 2
– Simpson Bay #959050a
$114 per night
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2BR/2BA
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Sleeps 6
– Simpson Bay #954068a
$143 - $250 per night
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Island Passion at Las Arenas, Saint Maarten
1BR/2BA
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Sleeps 2
– Simpson Bay #3247498ha
$257 - $515 per night
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2BR/2BA
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Sleeps 4
– Simpson Bay #862251a
$171 - $280 per night
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Spectacular Villa La-Di-Da Pelican Key St. Maarten
6BR/7BA
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Sleeps 12
– Simpson Bay #248845ha
$643 per night
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A Spectacular Well Appointed Ground Floor Unit with Breathtaking Views
2BR/2BA
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Sleeps 4
– Simpson Bay #146715ha
$1820 - $2625 per week 7 night min stay
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Beachfront Bliss-2-Bedroom Condo on Beautiful Simpson Bay
2BR/2BA
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Sleeps 4
– Simpson Bay #184582ha
$371 per night
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Elegant 1BR Condo with Rental Car Included!
1BR+/1BA
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Sleeps 6
– Simpson Bay #179176ha
$186 - $314 per night
- Simpson Bay Yacht Club Condo 2BR/1.5BA – Sleeps 6 – Simpson Bay #158182ha
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Newly Furnished Studio in Maho, St. Maarten Free Wi-Fi
Studio/1BA
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Sleeps 2
– Simpson Bay #3531600ha
$120 - $140 per night 2-3 night min stay
- Beautiful Large 1-Bedroom with Backyard Pool and Ocean Across the Road 1BR/2BA – Sleeps 6 – Simpson Bay #362862ha
- Beautiful St. Maarten Condo 2BR/2BA – Sleeps 6 – Simpson Bay #175310ha
- Summer Specials**1 Bedroom with Spectacular Ocean Views 1BR/1BA – Sleeps 4 – Simpson Bay #3247841ha
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Swimming Pool in the Residence, Front Beach and Restaurant. Ocean View
1BR/1BA
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Sleeps 1-4
– Simpson Bay #3537526ha
$120 - $350 per night 2 night min stay
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Affordable Luxury~Sea Belle Villa~ Oceanfront with Pool
1BR/1BA
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Sleeps 1-2
– Simpson Bay #137398
Overview of Simpson Bay Vacation Rentals
Simpson Bay Resorts on Antilles Island
Envision horseback riding along a sandy shore with the sun setting on the horizon, and you will have the ideal image of your Simpson Bay resorts vacation. Simpson Bay is located on the Dutch portion of St. Maarten, Antilles. The Antilles are broken into two sides, the Dutch and the French. St. Martin, Antilles is part of the western shore of the Greater Antilles Island. Though it is not a well-known fact, this island is the smallest land mass that two nations share peacefully. Long ago the two nations made an agreement that has allowed both to control portions of the Caribbean resort destination.
Yacht Sightings by Simpson Bay Lodging
Simpson Bay lodging sits above the largest lagoon in the western Caribbean. Simpson Bay Lagoon is shared equally with Saint Martin and St. Maarten. The larger land mass surrounding the lagoon is Saint Martin, the French nation. From St. Maarten rentals, you can watch mega-yachts come through one of the two draw bridges. The bridges are the only way to get into the lagoon as they sit over two narrow canals. Thousands of yachts visit Simpson Bay each year, especially during the summer months. You can also take the trip through the canal by booking a trip through Simpson Bay resorts.
Horseback Rides to St. Maarten Rentals
If you desire a glimpse of the sea around you from a higher altitude, leave your Simpson Bay lodging for the Seaside Nature Park. The nature park is on the Dutch side of St. Maarten, where natural beauty is only eclipsed by the amazing sunsets. Consider packing a picnic dinner at your St. Maarten rentals before going to the park. You can horseback ride, hike or stroll around Cay Bay which is part of the park before watching the sunset. Also consider spending the morning at the park to catch the sunrise.
Fun for the Family at Simpson Bay Resorts
Simpson Bay resorts are for the entire family with pirate treasure hunts, pizza, and soda offered in St. Maarten. Children can even take a pony ride along the shore of Simpson Bay Lagoon before relaxing by the pool at Simpson Bay lodging. St. Maarten rentals are close to many beach bars like Miss Lolo. Parents can feel secure in spending an hour or two at the bars after the children are asleep at this tropical destination.