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Simpson Bay Rentals with Pools

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677 villas in Simpson Bay with pools

Vacation Villa at Simpson's bay and Marina

Simpson Bay villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$172

2BR-Oceanfront-Royal Palm

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$453

PROVENCE... Affordable villa, gorgeous views, close to dining, shopping, casinos

Simpson Bay villa

6 bedrooms / 5 bathrooms / sleeps 12

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Price per night from

$643

Villa Ocean Pearl - Private Pool - 2 Masters - Private Courtyard

Simpson Bay villa

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$493

Beach view

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$594

ST TROPEZ... amazing views of the Caribbean Sea from this lovely villa in Pelica

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$557

WOW WOW WOW, STUNNING INSIDE AND OUT! VILLA LIBRE`

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

“Incredible ! Definiately five star 5* Accomdations” This villa is incredible. It exceeded my expectations. It was immaculate. It is beautiful inside and out. All three of the bedrooms are very spacious with their own large, modern bathrooms. The kitchen is also large for those who want to cook inside, plus there is a new BBQ on the patio, with a table beside. The grocery store and numerous restaurants are within walking distance. The panoramic view was spectacular. You can watch the boats go by all day and evening, and listen to the sound of the surf, just below. There is lots of sun or shade, whichever you prefer, from morning until night on the lovely patio. I would highly recommend this villa. It's first class accommodation in every way. I/we hope to spend more time at this villa next year. We loved it.

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Price per night from

$458

TARA... Affordable oceanfront villa, walk to beach

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

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Price per night from

$657

1Bedroom in Pelican Key

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 5

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Price per night from

$315

A breathtaking view

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$321

SUNSHINE VILLA... Huge, affordable beachfront villa, full AC, walk to restaurant

Simpson Bay house

5 bedrooms / 6 bathrooms / sleeps 10

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Price per night from

$850

SUR MER... Rare 3BR beachfront condo at Coco's Beach Club on Simpson Bay!

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$471

Villa Speranza | Near Ocean - Located in Fabulous Simpson Bay with Private Poo

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$660

SURFSONG VILLA-NEW LUXURY WATER FRONT VILLA-6 BEDS, also available in 4 and 5 be

Simpson Bay villa

6 bedrooms / 6 bathrooms / sleeps 12

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Price per night from

$1,424

BELLA VITA... Stunning Super Deluxe 7BR, Breathtaking Views, Full AC, and Tons

Simpson Bay villa

7 bedrooms / 8 bathrooms / sleeps 14

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Price per night from

$2,215

Beachfront Condo

Simpson Bay condo

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$590

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

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$329

SEA BEACH TREASURE... Gorgeous 2BR Penthouse on Simpson Bay Beach, St Maarten

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$350

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

Simpson Bay condo

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$343

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

Simpson Bay apartment

3 bedrooms / 4 bathrooms / sleeps 6

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Price per night from

$336

CASA DE BELLA... Great location at a great price!!

Simpson Bay house

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$400

Ocean Front with Private Pool

Simpson Bay villa

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$287

Steps to Caribbean, pool and 2 mile-long beach

Simpson Bay apartment

1 bedroom / 2 bathrooms / sleeps 2

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Price per night from

$258

SURFSONG... 6BR fall in love again! Breathtaking sunsets, directly on ocean!

Simpson Bay villa

5 bedrooms / 4 bathrooms / sleeps 12

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Price per night from

$1,497

Popular Beachfront property/ Barefoot in SXM

Simpson Bay condo

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$306

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

Simpson Bay apartment

1 bedroom / 1 bathroom / sleeps 2

“Cant get closer to the beach!” location was fantastic. apartment was plenty roomy. kitchen was well appointed. easy walk for groceries & to bakery for baguettes and croissants. nice music from mary's Boon just 2 doors down. couple of lovely spots to eat or drink an easy walk down the beach. We also walked to many restaurants along Welfare road simpson bay, easy 5-10 min walk. Driving over to Maho took only about 10 minutes. Room for improvement: need a better mattress. would be really nice to have lounge chair to take to beach and maybe one more chair in the living room, currently there is only a futon.

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Price per night from

$272

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

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$643

FAJA LOBIE... 3 BR Offers Great rates for a beachfront villa

Simpson Bay villa

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$700

Pelican Key 1Bedroom For Rent

Simpson Bay hotel apartment

1 bedroom / 1 bathroom / sleeps 4

“Great location, great resort, great service!” Just wanted to give a quick thank you and let folks know what a great time we had on our July, 2012 vacation in St Maarten at the atrium Beach Resort. Jackie (the lady who booked our condo) told us the place was being renovated and couldn't say if we would be in a new or "old" unit, oceanfront or non oceanfront, but for the price, we were totally fine with any 1BR. We ended up in a renovated room, oceanfront and of course thought we would owe more because the unit was worth way more than what we paid. Everyone at the resort was great. The pool was great. The location was great. Be sure to go to the Greenhouse downstairs for some great prime rib on Mondays and Crab Legs on Wed (I think I have the nights right, but check to be sure). And the Buccaneer Beach Bar is great on Fri nights for a fire on the beach which is actually in a ball with sculptured cut outs all around. I will definitely return to the atrium and will definitely use Jackie again for all my future bookings.

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Price per night from

$264

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

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$272

LITTLE SEAGULL... Pelican Key, St Maarten

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$300

WITENBLAUW... Magical Beach Front Estate on Pelican Key

Simpson Bay villa

6 bedrooms / 7 bathrooms / sleeps 12

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Price per night from

$2,072

UNFORGETTABLE... Beachfront contemporary condo on fabulous beach!

Simpson Bay apartment

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$482

CARIBBEAN BLUE... 5BR beachfront home in Pelican Key

Simpson Bay villa

5 bedrooms / 5 bathrooms / sleeps 10

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$914

MARY'S BEACH ESTATE... a plane watcher's dream! Huge observation deck at this be

Simpson Bay villa

6 bedrooms / 6 bathrooms / sleeps 14

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Price per night from

$1,522

Paradise Found at Las Arenas - Beachfront Luxury!

Simpson Bay apartment

2 bedrooms / 3 bathrooms / sleeps 4

“Amazing place - all the owner says it is, and more!” This was our first trip to St. Maarten so we had no idea what kind of places were available or what 'neighborhood' was best to stay in. I've got to say that we really lucked-out in choosing 'Paradise Found' in Las arenas. The building is very modern, and the Paradise Found unit is on 2nd floor so it's very convenient to to the pool and the complex is located directly on Simpson Bay Beach. This is arguably the best thing about staying at Las arenas as the beach has no big condo or hotel buildings...we practically had the entire beach to ourselves...and it's a long, wide beach. Water is warm and clear (it can be a little choppy but there were storms over the island when we were there late July/early aug). The unit itself has a huge, wrap-around balcony. The floor plan is great because the open central kitchen/living room area separates the two bedrooms. We heard hardly any sounds from the other units in the building. Maid service was three times during the week and was very good. The bathrooms, especially, are very nicely appointed and have an upscale hotel look and feel. Yes there is some noise from departing jets but only between 8am and 8pm (and there's only about a dozen aircraft departing during the whole day). The Simpson Bay location is convenient to lots of dining and grocery stores. Traffic out on the airport road (several blocks from Las arenas) can be a mess but that seems to be true all over the Dutch side. However at sunset you could even walk down the beach to Karakter or Mary's Boon (about 1/4 mile). The rental company is a local call if you need anything at all...they were very cordial. Yes, it is a little pricey but I consider it a great value for what you get.

Responds fast! avg. 2 hours 57 minutes

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Price per night from

$409

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

Simpson Bay condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$272

2 BEDR townhouse overlooking OCEAN ST- MAARTEN

Simpson Bay house

2 bedrooms / 1 bathroom / sleeps 4

“Fabulous resort living with a tropical breeze!” A most wonderful place to enjoy all St Maarten has to offer! Beautiful, airy, spotless accommodations with a contemporary Carribean decor and all the amenities you need for a wondrous vacation! Centrally located; walk to local French bakery , intimate Piano Bar, beautiful white sand beaches, beachside coctail bars, restaurants, shopping, etc! Parking for a rental car so you can hop all around the island. We enjoyed an absolutely fabulous time here..and at the end of the day a relaxing time gazing out at the turquoise ocean from our veranda!

Responds fast! avg. 3 hours 53 minutes

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Price per night from

$245

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