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2 Bedroom Beachfront Penthouse with 360 degree view, Private Roof Deck & Pool

Bedrooms 2
Space 700 sq ft
Property type apartment
Minimum Stay 7 nights


About the property

Fully furnished 2 bedroom suite for up to 8 (with 2 sofa beds).

Corner 4th floor air-conditioned penthouse. Separate lockout rooms: 1 one bedroom, one studio, each with king beds. Private roof deck with pool and kitchen and SPECTACULAR view. Each suite has full kitchen, washer, dryer, cutlery, dishes, glassware. Just add food and drink.

All the comforts of home - already here!


Cook in, dine out, entertain, be entertained, bring in a private chef (available) Have it just as you like it.

Property Manager
John Dunbar
Member since: 2015
Speaks english, Thai
Response time:
Within a day
Response rate:
Calendar last updated:
October 14, 2017

About John Dunbar

World travelers, retired after careers in government and private contracting. Currently live in DC area and in Arkansas.

Bette - Southern lady, advanced degrees, enjoys English murder mysteries, travel, power tools and gardening;

John - Army brat, former Arctic Ranger, community service, cooking, travel, good company

John Dunbar purchased this apartment in 2009

Why John Dunbar chose Oyster Pond

Being pampered. Relatively close to home. Being pampered. Treated like family. Being pampered, being well taken care of.

Convenient English-speaking right next door to a slice of France.

Laid back. Excellent restaurants.

Full conveniences of home.

Being pampered.

What makes this apartment unique

The private roof-top deck and pool, with grill, stove, fridge and bar.

The view, the view, the view. Ocean one side, harbor and mountains the other side.

Complete privacy with full resort facilities and some of the loveliest and friendliest people on the planet.

Plenty of activities, plenty of time and space to just kick back and relax.

Guestbook comments from the manager

Didn't realize how tired I was...'till I got to the condo and went out like a light. And awoke to the magic of St Maarten - deep blue skies; blue-green ocean and the sound of waves on the beach, sunny and warm with a constant quiet breeze.

Extraordinary food from nearby restaurants where you're greeted in friendly family welcome. People everywhere treat you like long-lost family, and graciously include you without reservation. John, the owner, is that way, too.

And then there's the rooftop pool/hot tub and barbeque area. Relaxing in the pool at 2:00 in the morning, looking up at a star-filled sky and listening to the waves. Nothing like it. NOTHING

It's like a slice of paradise - with all the comforts of home! I can hardly wait to go back - same condo, same pool, same everything.
May 2014
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Accommodation and Amenities for this vacation apartment rental in Oyster Pond

Property Type:
  • apartment
  • floor 4
Building Type:
  • building
  • Catering available
  • Breakfast - Booking Possible
  • Lunch - Booking Possible
  • Dinner - Booking Possible
  • Housekeeper Included
Floor Area:
  • 700 sq ft
House Rules:
  • Check-in: 4:00 PM / Check-out: Noon
  • Max. occupancy: 8
  • children not allowed
  • Minimum Age Limit for Renters ...
  • pets not allowed
  • non smoking only
Location Type:
  • Downtown ...
  • Mountain View ...
  • Oceanfront ...
  • Resort ...
  • Away From It All
  • Family
  • Romantic
  • Spa
  • Sports & Activities
  • Air Conditioning ...
  • Clothes Dryer ...
  • Elevator ...
  • Fitness Room / Equipment ...
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room ...
  • Parking ...
  • Telephone ...
  • Towels Provided ...
  • Washing Machine ...
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Kitchen ...
  • Microwave ...
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster ...
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , tub , shower , Double sink, towels changed daily, hair dryer, makeup mirror
    Bathroom - Studio - toilet , tub , shower
  • Bathroom on each side. The one-bedroom unit has a double sink, shower, bath, toilet. Studio has one sink, shower, toilet.
  • 2 Bedrooms, Sleeps 8
  • Bedroom 1 - 1 king , With private lanai
    Bedroom 2 - 1 king , Studio with private lanai
  • King bed with table and safe, private lanai, TV and bedroom. AC and ceiling fan. Maid service daily. One unit has a bedroom, the other is a connected studio.
  • Books ...
  • DVD Player
  • Games ...
  • Ping Pong Table
  • Satellite / Cable ...
  • Television ...
  • Video Games ...
  • Video Library
  • Balcony ...
  • Boat ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Outdoor Grill ...
  • Water Sports Gear ...
  • long term renters welcome
  • wheelchair accessible
Pool / Spa:
  • Communal Pool ...
  • Heated Pool
  • Hot Tub ...
  • Private Pool ...
Onsite Services:
  • Car Available
  • Concierge
  • Massage
  • Private Chef
  • Staff
  • botanical garden
  • cinemas
  • duty free shops
  • festivals
  • health/beauty spa
  • library
  • marina
  • playground
  • recreation center
  • restaurants
  • zoo
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • gambling casinos
  • horseback riding
  • luaus
  • miniature golf
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • walking
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • golf
  • jet skiing
  • kayaking
  • paragliding
  • parasailing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • snorkeling/diving
  • sound/bay fishing
  • surf fishing
  • swimming
  • water skiing
  • wind-surfing


Wonderful! 4.9/5 -
(9 traveler reviews)

88% Complete
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2 Bedroom Beachfront Penthouse with 360 degree view, Private Roof Deck & Pool
average rating of 4.888889 based on 11 reviews

Great views

  • 4 of 5

Awesome 2 bedroom penthouse with great views of the ocean and oyster bay. Only setback was the rooms are ready for a refresh, a lot of bathroom fixtures leaking and unsecured from walls and door trims between bedroom and living area

  • Submitted: 20-Feb-2017
  • Stayed: February 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you! I'll get on it with maintenance and get these corrected!
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The best vacation experience I have ever had!

  • 5 of 5

We spent our family’s first vacation in years on St Maarten at Oyster Bay Beach Resort. Choosing this penthouse double suite was our best decision. Luxurious interior, a balcony in every room with the astonishing view of the ocean, the best part however, is the rooftop deck with private pool overlooking the resort’s infinity pool, a beach and the harbor. The deck is equipped with lounging chairs and umbrellas, it also has a grill and a dining area, which makes it a perfect place to have dinners right under the stars. The owner, John, was very friendly and accommodating; he told us the best places to shop at and eat out, he also suggested us some of the unique wonders the island has to offer. This was truly an unforgettable vacation!

  • Submitted: 25-Jan-2017
  • Stayed: November 2016
  • Source: VRBO, from HomeAway
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Another Trip to Paradise!

  • 5 of 5

This was my second stay at this condo in St. Maarten and it proved to be as memorable and enjoyable as the first time! The best part is the rooftop deck that affords privacy, a personal pool and tanning area, and breathtaking views of the ocean and sky. If you are after total relaxation, this is the place. John, the owner, was easy going, dependable, and extremely helpful in answering questions I had.

  • Submitted: 25-Jan-2017
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
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Vienna, VA

Outstanding Vacation Escape

  • 5 of 5

This was my fourth year in a row renting these units at Oyster Bay Beach Resort and I continue to be thrilled with my vacation experience! This unique top floor end unit provides the resort’s best view out over the ocean, communal infinity pool, and the harbor. While you have great views from both units, the view is truly spectacular from the rooftop penthouse where you can swim in a private pool and jacuzzi, relax in lounge chairs with umbrellas, grab a beer from the portable refrigerator, and grill and dine under the stars. Several amenities on site make for a total experience including excellent restaurants, a spa and fitness center, a small grocer, and a beachside bar. Staff is friendly and helpful. The owner, John is terrific to work with and can offer lots of advice on the many adventures that the island offers. I unreservedly recommend this rental as an outstanding vacation escape!

  • Submitted: 24-Jan-2017
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
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A true gem!

  • 5 of 5

This penthouse unit is truly a Caribbean gem! Located near the border makes it convenient to travel between the two countries. The owner is very knowledgeable and gave us wonderful recommendations for shopping, dining and sightseeing. But the private rooftop is so awesome that it makes it difficult to want to do anything except relax by the private pool/jacuzzi admiring the stunning view of the marina on the harbor side and the Caribbean Sea on the other side. Both units have balconies off the bedrooms that overlook the sea. What a great view to wake up to! The living room also has a balcony with a table for four that many meals were enjoyed at. If you enjoy people watching, the balconies overlook the resort's pool. They offer water aerobics and yoga and have a nice fitness center. If you go into town on Sunday, most things are closed unless a cruise ship is in port. We did not eat at any of the onsite restaurants since we had a car and wanted to dine in the French restaurants. A favorite was Mama's Pizza, which is very close to the resort on the French side. They also deliver. The market in Marigot was a real treat! Wednesday is one of the better days to go although they are open every day the cruise ships are in port. The spices were the best part of my shopping experience. I am so happy to have been able to stay at this wonderful resort and can't wait to go back again.

  • Submitted: 22-Feb-2016
  • Stayed: February 2016
  • Source: VRBO, from HomeAway
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Vienna, VA

Fabulous getaway retreat

  • 5 of 5

What a fabulous getaway retreat this site offers! I can't say enough good things about this penthouse apartment and adjoining studio unit at Oyster Bay Beach Resort. I have stayed in these units in each of the past three years and plan on coming back again next year.

The rooftop (penthouse) is the real gem of this vacation rental. A private pool and jacuzzi, lounge chairs, umbrella and sunning area, grill, fridge and dining table, and the view -- oh the view! -- out to the ocean on one side and out to the harbor on the back! (not to mention the view upward to the sky). You could easily spend your entire week on the roof alone!

But the island has lots to offer as well. I highly recommend the butterfly farm, the midweek vendor market in Marigot for souvenirs, the shops in Phillipsburg where the cruise ships dock, and oh the fabulous restaurants, particularly on the French side. Oyster Bay is on the quieter side of the island just at the Dutch/French border so offers easy access to key cities and sites.

If you prefer not to rent a car, everything you need is onsite at Oyster Bay. High quality restaurants, a small grocer, beachside bar, and fitness center, among other amenities. Staff are incredibly friendly and willing to help. The concierge can arrange any special adventures you might want to engage in (snorkeling, a day trip to St. Barth, horseback riding, etc).

If you are looking for a relaxing escape to paradise, this is the place!

An added plus is that the owner is very easy to work with and is fair and reliable

  • Submitted: 27-Jul-2015
  • Stayed: May 2015
  • Source: VRBO, from HomeAway
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Nearest Airport
17 Kilometres
Princess Juliana (SXM)
Nearest Ferry
1 Kilometres
St Barth's
Nearest Golf
14 Kilometres
Mullet Bay
Nearest Restaurant
1 Kilometres
Infinity, Beau Beaus, Big Fish, Canoa
Nearest Beach
1 Kilometres
Car: recommended

The exquisite 4th floor corner penthouse of the Mainsail Building located in the gated Oyster Bay Beach Resort (OBBR) in Oyster Pond, Dawn Beach, on the Dutch side of the French/Dutch border. The penthouse enjoys access to the facilities of the Resort while having private amenities such as the large 2-level private rooftop deck with lap pool (with Jacuzzi), and outside kitchen: bar, fridge, sink, grill and dining area. The 360-degree view of sea, mountains and harbor from our rooftop unit is stunning; the sound of the sea is enchanting.

OBBR is located right on the ocean, on the East side of St. Maarten at Dawn Beach - away from airport and city noise and crowds, and backs up to a marina with deep draft access. Just a short ride to Phillipsburg, the airport, and other area attractions; the Westin Hotel and Casino is within a mile.

This unit is a two bedroom lockout suite for four (up to 8 with 2 sofa beds). The units can be rented separately, though we prefer to rent as a whole. This unit has a master bedroom suite with living room, kitchen with clothes washer/dryer and dishwasher, and an adjoining studio with kitchen and bath, each sleeping up to 4. Each room - living room and each bedroom - has sliding glass doors opening onto ocean-front balconies with 180 degree views from Tintamarre Island to Dawn beach. Prepare to be spoiled: maid service is daily.

You’ll have complete access to all facilities and activities of the full-service Oyster Bay Beach Resort including beach, restaurants, spa, pool, exercise facility with great equipment, and shops. Two first-class restaurants, a pizzeria, an open-air beachfront restaurant and a grocery are within a 3-minute walk. There are organized activities daily at the resort. Concierge service is most gracious and friendly.


Air Conditioning : Zoned, central air conditioning

Ceiling fans in every room

Maid service

Elevator : 10 steps to penthouse unit

Washer : Front-load washer/dryer in kitchen

Parking : Secure parking within property gate


King Beds

Queen-sized convertible sofa in living room and in junior suite


Private lap pool/Jacuzzi/hot tub on top roof deck

Cable/Satellite TV: US satellite stations; 2 TVs in 1-bdr suite; 1 TV in junior suite.

DVD/CD player: 1 per suite

Shared Pool : Resort infinity pool for OBBR residents

Clothing optional beaches nearby


Full kitchen: G.E. monogram stainless appliances: dishwasher, microwave, refrigerator, freezer, range hood, glass top cooking service, large oven/convection, large pantry, under cabinet lighting, granite countertops, large island with seating for four.

Cooking utensils, flatware, glassware and dishes provided


Catering Available : for menus

Outdoor Features

Gas/Electric BBQ Grill : Private roof-top gas grill

Deck/Patio : Large, private sun deck on roof

Balcony (3): Each bedroom and living room has a private balcony with ocean view. One features lounge chairs, two have a dining table with chairs; all have spectacular views of Dawn Beach.


Beach View : Dawn Beach is steps from the property

Oceanfront: This property is directly on the ocean with panoramic views of the Atlantic and Caribbean from every room.


Telephone: Local telephone service

WiFi (Wireless Internet) (Skype access)

Other Amenities

Roof-top deck, sunning pavilion, and pool


No Pets Allowed

Handicapped Accessible (limited): Full elevator access, wide doorways, large shower, toilets will not accommodate wheelchair.

Not Suitable for young children. Minimum Age Limit for Renters:

Under 25 must be accompanied by a responsible adult.

Smoking Not Allowed: Smoking in unit will result in forfeiture of deposit.

Other Activities

Concierge services, private chef and catering available, zip-line adventures, world class golf on Anguilla - a short ferry ride away

Why the Owner Chose Dawn Beach

This building is unique to St. Maarten with 20 units on 4 floors. An elevator takes you to our top floor corner penthouse with ocean, marina and beach views as well as views of boats entering and leaving Oyster Pond, and the ferry to St. Barths.

The Unique Benefits of this Condo

The Mainsail at Oyster Bay is within the Oyster Bay Beach Resort property, and allows renters to use all the resort facilities while maintaining its own amenities including a roof-top private pool, jacuzzi, kitchen and dining area, and sun pavilion.


Rates & Availability

Rental Rates for this vacation apartment rental in Oyster Pond

Rental Basis:
per property
Manager accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly Event
My Standard Rate
7 night minimum stay

Manager's Cancellation Policy

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.
Contact Manager