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Best Oceanfront 2 Bedroom Villa in Guana Bay Sint Maarten; Hot Tub, Ocnfrt Deck

36 Reviews
Bedrooms 2
Property type villa
Minimum Stay 1 - 7 nights

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Minimum Stay
1 - 7 nights


Upper Prince's Quarter Villa Rental Photos and Description

2 Bedrooms, 2 Baths, Sleeps up to 6. Closest To The Ocean! Most Popular Villa

Villa Leone Sint Maarten is located on Guana Bay in St. Maarten, Netherlands Antilles. The area surrounding the villa is nestled between the foot of a large hill and the beautiful Atlantic Ocean. We are 3-1/2 hours from New York and 3 hours from Miami. Both Continental and American Airlines service the island. We are on the Dutch side of the island, 25 minutes from Juliana Airport and 15 minutes from Downtown Philipsburg. Philipsburg has shopping, fine restaurants, medium and expensively priced. This is where the cruise ships dock. We are on the tradewind, or windward side, which offers great winds 12 months a year. We are 25 minutes from Marigot, the capitol of the French side, and 20 minutes from Grand Case where many of the finest restaurants are located.

Celine Party Cruise: Try an evening cruise of the lagoon on the Celine; a beautiful catamaran where you can have an open bar and make stops at 3 restaurants to sample their food and drink....a great deal and a lot of fun!

Golden Eagle Round The Island Cruise: This usually leaves only on Friday but is a must do! It's only around $100 but well worth the price. You will spend the whole day on a 65' catamaran and have open bar, visit Tintamarre Island, snorkel at two locations and stop for a sit down lunch in Grand Case, the culinary capital of the Caribbean on the French Side. You should not miss this adventure!

Villa Leone can be rented together with 'The Waves; HomeAway listing #3918755, the 2 bedroom one bath ground floor level directly under Villa Leone. This configuration will provide 4 bedrooms and 3 baths and can sleep up to 10 guests using the sleeper sofa in Villa Leone.

Although Villa Leone and The Waves can be rented together, they are distinctly separate units with no shared stairways, entrances or doorways; insuring privacy between the two units when separately occupied.



Have breakfast at Chesterfield's in Philipsburg; a 10 minute drive. This restaurant is set directly on Bobby's Marina with fantastic water views. After breakfast, do a loop of the island to get a feel for what you may be interested in seeing during your stay. I recommend stops at Friar's Bay Beach as well as Marigot during your island loop. An afternoon stop at The Sunset Beach Bar near the airport is also nice. You can watch the large jumbo jets land just feet in front of you!

You will be tired after your long day circling the island, so, go back to The Waves for cocktails on your oceanfront patio.


After breakfast on the oceanfront patio, take a walk next door to explore Gibbs Bay Beach and then cross back by The Waves and walk down to Guana Bay Beach. There is a trail head at the end of Guana Bay Beach that will take you along the oceanfront into Philipsburg. If you are hikers, this would be a great way to spend the morning.

At night, a drive to Simpson Bay for dinner at Lee's and after for karaoke at Toppers could be fun.


If you like to snorkel, on day 1 or 2, make a reservation on one of the catamarans that go out of Bobby's Marina. Breakfast at Chesterfield's again. It's right near where the boats leave from Bobby's Marina.They have all day sails that have open bar, lunch and snorkeling at two or three spots. A great day!

At night, if you have any energy left, dinner and drinks at the Greenhouse; also near Bobby's Marina, is a good choice.


After breakfast on the patio, drive into Phiipsburg, park at the lot across from Windward Islands Bank and spend the morning walking along Front Street shopping and along the waterfront Boardwalk. The shopping for jewelry and electronics is very fun and can result in a great deal for the educated consumer. You can buy two beers and a Cuban cigar for $3 from the street vendors. You can rent Segways and ride along the Boardwak. One stop that I recommend is the Guavaberry store. Their shakes are delicious and thirst quenching. For lunch, try Kangaroo Court. Many local business owners eat here for lunch. Sit in the back by the huge old tree. Very nice setting!

At night, try Bamboo Bernies in Maho if you like sushi. Be sure to make a reservation though. They are always packed! After dinner, nearby is Soprano's piano bar; always a fun time.


One day on the French Side can be a nice experience.

In the morning, you can drive to Marigot, park and walk around the town. There is a nice hilltop fort to visit.

Be prepared to pay for everything in Euros on this side of the island. You can even hop on the ferry and go to Anguilla; a 20 minute ferry ride. There are nice beaches there and you can chalk off another island.

At night, continue on to Grand Case. This is a small town on the French Side that is home to a few excuisite French restaurants. Dinner can be pricey but the experience can be unforgettable!


A visit to Orient Beach on the French Side is a possibility for today. You can turn right at where the road from Guana Bay intersects the main road and continue north to Orient Beach. The beach is divided into nude and bathing suits required. The decision is yours!

You can then return to your favorite nightspot to finish off your week on this very fun island.

More Details
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters
  • children welcome
  • non smoking only
  • pets considered
  • wheelchair inaccessible

Property Manager
Frank Leone
Member since: 2004
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
October 12, 2016
Call Manager

About Frank Leone

I am a Registered Professional Engineer in Pennsylvania.

Frank Leone purchased this villa in 2004

Why Frank Leone chose World

The views from the deck of Villa Leone are something that words and photos alone can not adequately capture.

What makes this villa unique

Only a 5 minute drive from the capitol of Philisburg; where all the cruise ships dock with many restaurants and great shopping.

Guestbook comments from the manager

We have thoroughly enjoyed our stay and want to thank you for everything.
Feb 2014
  • 1 of 4


based on 36 traveler reviews

Best Oceanfront 2 Bedroom Villa in Guana Bay Sint Maarten; Hot Tub, Ocnfrt Deck
average rating of 4.9166665 based on 40 reviews

Great villa and location

  • 5 of 5

Our stay at Villa Leone was fantastic. The location of the villa is right on the water on Guana Bay

with easy access to Guana Bay beach and Gibbs Bay beach. The villa location was quiet and is

a quick ride to Philipsburg. The breeze and sound of the ocean made the atmosphere of our stay outstanding.

If you like sitting outside on a balcony enjoying a cool breeze and a great view of the ocean this is a perfect place for that.

The villa was well kept, clean, and had all the amenities needed for a comfortable stay. The kitchen was well

stocked for cooking in (which we did a good amount of), the bedrooms very comfortable, and the living space

perfect for the four of us. Upon our arrival, we had no trouble getting into the Villa (Simon greeted us at the entrance)

and parking was easy. Frank was outstanding in his responses to any questions with great information and quick

replies. We did not make use of the hot tub but did use the pool a couple of times which was very nice especially for

a late afternoon/evening swim. All in all, it was a great experience and we would absolutely return to Villa Leone.

  • Submitted: Mar 14, 2016
  • Stayed: Feb 2016
  • Source: HomeAway
Owner's Response: Hello Brian, I'm happy to hear that you enjoyed your stay. I agree with you that the experience of sitting or standing on the oceanfront deck and watching the powerful waves and gorgeous views of St. Barths is an experience that is mesmerizing, relaxing and almost magical. It's my favorite thing to do when I am in Sint Maarten. Of course, dining at the many fantastic restaurants is my 2nd favorite. We hope to see you back soon! Thank you for choosing Villa Leone. Ciao, Frank
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1 0
Philadelphia, PA

Fourth Time Back

  • 5 of 5

We have been coming to Villa Leone since 2007.

There is always something new in the way of changes or improvements.

Last trip was the new kitchen. The new tile floors the time before that.

The new sliding door to the oceanfront deck was welcomed this trip. The old one was getting a little hard to slide open.

The thing we like most about the villa is the oceanfront deck and hot tub.

The panoramic unobstructed views from the deck are without equal and are the best to be had from any available rental unit in Guana Bay.

The wifi was great, as usual and allowed us to keep in touch with the real world on occasion when we got bored of relaxing in the hot tub and pool; which is right at the bottom step of the villa.

Another nice change was the upgrade in the master bedroom from a queen to a king bed.

Simon, as always, was there to meet us upon arrival. He checks in to make sure all is well and to see if anything is needed.

  • Submitted: Dec 6, 2015
  • Stayed: Nov 2015
  • Source: HomeAway
Owner's Response: Hello Jackie, Thank you for taking your valuable time to share your experience. We hope to see you back at Villa Leone very soon. Merry Christmas and Happy New Year. Ciao, Frank
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1 0
Highland Park, Michigan

Villa Leone in Guana Bay St. Maarten

  • 5 of 5

The villa's amenities and location both met and exceeded our expectations. Although we were delayed getting to the villa because 1 of our party's bags did not arrive with our flight, Simon was still there to greet us. The villa was clean and well-maintained. What you see is really what you get. Having free wi-fi and an "on-the-premises" phone from which to make local calls was a BIG plus! There are many fine restaurants in Phillipsburg and the Grand Marché Supermarket in Cole Bay was as good as any in a major US city. Villa Leone is a perfect "off-the-beaten-path" location. We will return again.

  • Submitted: Mar 23, 2013
  • Stayed: Mar 2013
  • Source: HomeAway
Owner's Response: Hello Frank and Pat, So glad that you enjoyed your stay at Villa Leone Sint Maarten. Guana Bay Beach, Gibbs Bay Beach, Villa Leone and Simon all await your return. Also, please consider a stay at Villa Leone Cabarete in the Dominican Republic. Thank you so much for your patronage. Ciao, Frank
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1 0

Wonderful Villa but Windward location a letdown

  • 3 of 5

As all the other reviews can attest – this is a wonderful villa with a great owner and caretaker with lots of perks you wouldn’t find in a hotel. The filtered water & ice from the fridge, the cooler, cell phone, grill, hot-tub and free wireless were great amenities which made our stay even more enjoyable. The condo itself is aging but clean and well-maintained; the furnishing, appliances and electronics are relatively new and in great shape. There was plenty of hot water for 4 people at all times. The communication from both Frank & Simon was above expectations and extremely welcoming and friendly. This helped set the trip on the right foot before we even left and certainly made it even more enjoyable while we were there. The community pool was in great shape and during the day we had no issues with mosquitoes outside or dogs. The landscaping in the area is island/dessert minimalist.

The caveat in all of this is the location and the windward/tradewind aspect of the geography. There were extremely strong sustained winds with even stronger gusts every day of the entire week we were there at all times of the day. The otherwise lovely terrace was unfortunately not very tranquil or sanguine and it was impossible to eat outside (food would blow away), hard to hold a conversation or read a book and quite chilly even in the full sun. The layout of the terrace is such that the entire portion is windward facing and there is no respite around the house or with something obstructing the direct blast (we found the hefty deck chairs were frequently blown over during the course of the day). The nearby beaches were deserted for this same reason and the water was far too tumultuous to warrant going in far.

Ultimately this meant every day was a traveling day to other areas (orient beach, pinel island, baie rouge and simpsons bay were all wonderful) and that time at the villa was largely indoors. I have to assume that that the wind is mostly luck of the draw and had we gotten a few less windy days I would have given a higher overall experience. As we were hoping this villa would itself be a destination escape the constant need to travel elsewhere was a letdown. Guana bay is a ways away and often what should be a 15 minute drive doubles with the islands traffic situation.

  • Submitted: Feb 15, 2010
  • Stayed: Jan 2010
  • Source: HomeAway
Owner's Response: One of the reasons I purchased Villa Leone is because of it's Windward location. The breezes and waves remind me of my days growing up visiting the New Jersey shore. Many guests want to confirm that there will be waves so they can boogie board. For guests wanting bathtub calm water, I do recommend to them the leeward side of the island. As evidenced by the 32 previous reviews, the wind and waves has never been a point of disatisfaction. I do believe from your description of the winds that their duration and intensity was close to hurricane or tropical storm conditions. I also understand how this unfortunate weather week would have a negative affect on your overal experience and I do sympathize with you. However, I have yet to figure out how to control this very variable element to better ensure a positive experience for our guests. I very much appreciate your very nice comments about Villa Leone and strongly suggest that you give another chance to the windward side. I'm sure the odds will be in your favor next time and you will have more pleasant calm or moderate winds with wich to enjoy the intoxicating views from the deck of Villa Leone. Ciao, Frank and Patty
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2 0
Amherst, MA USA

Villa Leone, Sint Maarten

  • 5 of 5

The property was just as the pictures had showed and Simon was waiting for us upon our arrival. The villa was clean, bright, airy and provided everything that we could have needed for the week. The portable cooler was a blessing for packing picnic beach lunches and keeping food and drinks cold.

We visited several places on both the Dutch and French side. It is very true that the exchange rate on the Dutch side is much more favorable to those coming with dollars, as the Euro is very strong in comparison. If you want great shopping, cheap food and drinks, the Dutch side on the island is the place to go. Front Street in Phillipsburg was amazing. We got great deals on jewelry, alcohol and electronics. There was a place down a small alleyway off of Front Street headed towards the water that advertised 2 beers and 1 Cuban cigar for $3. We had to find out what the catch was! The catch was that there was NO catch. 2 full sized beers and a decent cigar for $3. A nice break in the day if you need one while shopping.

We visited several beaches while on the Island, on both the Dutch and French side. Happy Bay is worth the walk through the woods. Small, secluded with very few people. If water sports and activities are what you are looking for, Orient Beach has everything you could want, but in terms of relaxation and peacefulness, there are far too many people for that. Baie Rouge was very nice and the snorkeling was great with a swim through cave. We highly recommend the conch kebab served at Chez Albert on this beach (watch out though, it is expensive and in Euros). Guana Bay was great for boogie boarding and you can't beat the view of St. Barth's.

We ate a very nice meal at L'Esparade in Grand Case. Right on the water, great food, funny host, excellent service, reasonable prices for a traditional French restaurant. But really, every restaurant on the road is outstanding. Try fried plantains somewhere (lots of places have it), there are great when done well.

If you are looking to get off of the beach for a little bit, we went to Loterie Farm for part of a morning and did their Zip Line and Ropes Course ($45US for the basic course that took us about an hour and $70US for the extreme). Loads and fun and appropriate for lots of ages. There was a 7 year old behind us having the time of her life on a kids course.

  • Submitted: Jun 15, 2009
  • Stayed: Jun 2009
  • Source: HomeAway
Owner's Response: Glad to hear that you enjoyed your stay at Villa Leone Sint Maarten in Guana Bay. We look forward to welcoming you back to Villa Leone Sint Maarten or, possibly Dominican Republic for a different island experience. Ciao, Frank
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8 0


  • 5 of 5

Breathtaking! Nice beach, great waves! Beach bar is nice. We had a wonderful 2 weeks-we did the zip line at Loitler Farm, Chartered a boat w/ the Garfield 2, and horse back riding on the dutch side. Can't wait to rebook @ Villa Leone! Thanks Frank!

  • Submitted: Mar 25, 2009
  • Stayed: Mar 2009
  • Source: HomeAway
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1 0


Sunset Beach Bar
"Best bar for people and plane watching"
Bamboo Bernie's
"Best Sushi Place on the Island"
Friar's Bay Beach
"Calmest Water on the island"
Chesterfields Restaurant & Bar
"My favorite place for breakfast"
Guana Bay Beach
"Right next door to Villa Leone. Very private!"
"Nice place for lunch or dinner. Right on the water"
Taloula Mango's
"Nice place to eat on the boardwalk"
Nearest Airport
10 Miles
Princess Julianna Airport St Maarten
Nearest Barpub
3 Miles
Nearest Ferry
4 Miles
Nearest Golf
10 Miles
Nearest Motorway
2 Miles
Nearest Restaurant
3 Miles
Nearest Beach
Car: recommended

Villa Leone is located in the tranquil setting of Guana Bay; a pristine beach all by itself but yet only 5 minutes drive to the capital city Phillipsburg, where the cruise ships dock.

Golf: There is a beautiful golf course in Mullet Bay that is right next to the ocean!


Rates & Availability

Upper Prince's Quarter Villa Rental Rates

Rental Basis:
per property
Manager accepts payment in:
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Rate Period Nightly Weekend Night Weekly Monthly * Event
Sep 2 2016 - Dec 11 2016
1 night minimum stay
Dec 12 2016 - Dec 19 2016
7 night minimum stay
2016 Holiday Period
Dec 20 2016 - Jan 9 2017
7 night minimum stay
Jan 10 2017 - Apr 12 2017
4 night minimum stay
My Standard Rate
2 night minimum stay
Notes: Rates are based on 2 guests; add $30 per night, per additional guest

Additional information about rental rates

All listed rates based on 2 guests. Please add $30/pp/night for additional guests.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
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Upper Prince's Quarter Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 1000 sq. ft.
Location Type:
  • Beach
  • Beach View
  • Beachfront
  • Mountain View
  • Ocean View
  • Oceanfront
  • Water View
  • Waterfront
  • Waterfront
  • Away From It All
  • Budget
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Activities Guide
  • Air Conditioning
  • Ceiling Fans
  • Filtered Water
  • Hair Dryer
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Local Restaurant Guide
  • Mobile Phone
  • Parking
  • Parking Off Street
  • Parking On Street
  • Safe
  • Security System
  • Sofa Bed
  • Towels Provided
  • Wireless Internet
  • Blender
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Stove
  • Toaster
  • Dining
  • Dining Area
  • seating for 4 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , shower , bidet
    Bathroom 2 - toilet , shower , bidet
  • There are two bathrooms. The master bathroom is en-suite and offers a bidet, toilet, sink and shower. The guest bath also offers bidet, sink, toilet and shower.
  • 2 Bedrooms, Sleeps 6
  • Master Bedroom - 1 king , Master Bedroom Has Ensuite bath
    2nd Floor Bedroom - 2 twin/ single , The 2 twin beds can be assembled together to form a king bed
  • Villa Leone is ideal for two couples, offering two separate baths and a door that separates the upstairs bedroom/bath from the lower living area. The upstairs bedroom has two twin beds that can be put together to form a king bed. The lower master bedroom has a king bed. The living room sofa is a pull out queen bed.
  • Books
  • DVD Player
  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Video Library
  • Balcony
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill ...
  • Small Cooler
  • Walkway to Water
  • 2 garden chairs
  • 2 beach chairs
  • Long-term Renters Welcome
  • Minimum Age Limit for Renters ...
  • children welcome
  • non smoking only
  • pets considered
  • wheelchair inaccessible
Pool / Spa:
  • Communal Pool
  • Hot Tub ...
  • Outdoor Hot Tub
  • bay/sound
  • churches
  • cinemas
  • duty free shops
  • marina
  • museums
  • pond
  • restaurants
  • zoo
Leisure Activities:
  • beachcombing
  • bird watching
  • eco tourism
  • gambling casinos
  • horseback riding
  • scenic drives
  • sight seeing
  • walking
Local Services & Businesses:
  • Babysitter
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • golf privileges optional
  • hiking
  • jet skiing
  • mountain biking
  • pier fishing
  • sailing
  • scuba diving or snorkeling
  • snorkeling
  • sound/bay fishing
  • swimming
  • water skiing

Learn more about this vacation rental at the manager's website:

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