
Palapa Marina Rentals

- From $605 per night (USD)
VRBO
Villa Saint-Tropez
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the sought after area of Pelican Key, next to all the casino bars restaurants of Simpson Bay, the beautiful b ...
From $605 per night (USD)VRBO
- From $3080 per night (USD)
VRBO
Bella Vita - Seven Bedroom Villa, Sleeps 14
- Bedrooms:
- 9
- Bathrooms:
- 7
- Sleeps:
- 14
Life is good at villa Bella Vita, a sumptuous 7 bedroom contemporary home located in the residential enclave of Pelican ...
From $3080 per night (USD)VRBO
- From $380 per night (USD)
VRBO
SIMPSON BAY on beach 2 BR, 2.5 bath, panoramic ocean view, pool, GENERATOR
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
ENJOY THE BREATHTAKING OCEAN VIEWS OF MEGA YACHTS, SAILBOATS, WATER ACTIVITIES AND BEACH FROM YOUR DOUBLE WIDE TERRACE w ...
From $380 per night (USD)VRBO
- From $2258 per night (USD)
Expedia
Beachfront Witenblauw Estate, the best beachfront property in dutch St.Maarten
- Bedrooms:
- 7
- Bathrooms:
- 11
- Sleeps:
- 24
They say a picture is worth a thousand words… That being said, Witenblauw speaks volumes when it comes to making memorie ...
From $2258 per night (USD)Expedia
- From $83 per night (USD)
VRBO
LimeTree Studio, Pelican Key. Cozy retreat in excellent location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
LimeTree Studio apartment is located on the first floor of a private villa in the beautiful and conveniently located res ...
From $83 per night (USD)VRBO
- From $700 per night (USD)
Expedia
One Hundred Million Dollar Yacht On Land 5 star Villa on the ocean
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to paradise ! this newly updated and unique beach-side Villa Namaste – an ultra luxury, multi-faceted dream be ...
From $700 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Beach Front Modern Condo on the beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Your stay at this property will leave you with a very luxurious and modern Caribbean vacation experience. It is the pref ...
From $418 per night (USD)VRBO
- From $468 per night (USD)
Expedia
Il Punto Blu - Beautiful renovated condo, AC, WIFI, walkable restaurants/beach.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Escape to Il Punto Blu – Beachfront Luxury in Pelican Key, St. Maarten Experience the best of island living at Il Punto ...
From $468 per night (USD)Expedia
- From $351 per night (USD)
VRBO
Stunning 2BD oceanfront villa; spacious, modern, and close to restaurants/bars
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our oceanfront in Pelican Key/Simpson Bay, 2 bedroom, 2 bathroom private villa is a short walk to great shops, restauran ...
From $351 per night (USD)VRBO
- From $128 per night (USD)
Expedia
Top of Pelican Key! Spectacular sea views, near beaches, Wifi, parking, private
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Relax and enjoy your vacation in this 1 bedroom studio situated in a private villa. Villa Cleavage is nestled between th ...
From $128 per night (USD)Expedia
- From $474 per night (USD)
VRBO
Paradise in the West Indies
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in Simpson Bay, within steps of Simpson Bay Beach. Coco Beachfront Bliss offers a tranquil view including the fo ...
From $474 per night (USD)VRBO
- From $841 per night (USD)
VRBO
Villa Seaclusion accommodates 20 guests 10 beds 6 villas Ocean view pool
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 20
One of a kind, just completed high-end renovation resulting in the most desirable, spacious residence in Pelican Key. Ov ...
From $841 per night (USD)VRBO
- From $268 per night (USD)
VRBO
Simpson Bay Ocean View - Deluxe 1 Bedroom Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We normally have a min night requirement. These condo's are owned and Managed by Mary's Boon Beach Hotel and Spa and its ...
From $268 per night (USD)VRBO
- From $3094 per night (USD)
VRBO
Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: BELLA VITA 7BR, Pelican Key, St Maarten Life is good at Villa Bella Vita, a sumptuous 7 bedroom contemporary ...
From $3094 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Studio on the water in the Simpson Bay Yacht Club
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The studio is located in the Simpson Bay Yacht Club right on the waterfront. A gated residence with 24/7 security, 2 swi ...
From $180 per night (USD)VRBO
- From $569 per night (USD)
Expedia
3 BR Ocean View Villa in Pelican Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to this beautiful "St Tropez Villa" with superb ocean views on the hill in Pelican Key with everything you’ll nee ...
From $569 per night (USD)Expedia
- From $545 per night (USD)
VRBO
LUXURIOUS BEACH FRONT UNIT - SPECTACULAR OCEAN VIEWS.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Simpson Bay is bordered by a beautiful 2-mile long, lightly-populated curved beach. It Heaven fronts right on the beac ...
From $545 per night (USD)VRBO
- From $1219 per night (USD)
Expedia
BLUE OPAL Private Pool-Generator, Ocean Views Pelican Key - Simpson Bay
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Blue Opal can be booked as a 3 or 4 or 5 bedroom villa. Please ask about special rates... **During Xmas/New Years’ week ...
From $1219 per night (USD)Expedia
- From $641 per night (USD)
VRBO
Amazing Ocean Front Villa in Pelican Key - Pool and Private Ocean Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
'La Calanthe', named after a beautiful variety of Orchids is a beautiful Villa. It sits right in front of the ocean all ...
From $641 per night (USD)VRBO
- From $1404 per night (USD)
Expedia
Villa Vittoria | Beach Front - Located in Exquisite Simpson Bay with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Private Villa Rentals is licensed and registered with the Travel Industry Council of Ontario (TICO) which protects your ...
From $1404 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Pelican Key Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
My place is close to the beach, family-friendly activities, nightlife, public transport, and the airport. You’ll love my ...
From $250 per night (USD)VRBO
- From $219 per night (USD)
VRBO
1 BR-Walk out patio and jump in the pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
This 1 bedroom/2 full bath unit is located in the very desirable Pelican Key, next to La Vista Resort. The bedroom has a ...
From $219 per night (USD)VRBO
- From $595 per night (USD)
VRBO
Sea View @ La Siesta, Simpson Bay, St. Maarten, N.A.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Siesta Residence is a small private 13 unit villa/condominium resort comprised of two buildings. Building A has ten ...
From $595 per night (USD)VRBO
- From $143 per night (USD)
VRBO
Studio Simpson Bay Yacht Club
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The studio is located in the Simpson Bay Yacht Club. A gated residence with 24 hours security, a swimming pool overlooki ...
From $143 per night (USD)VRBO
- From $216 per night (USD)
VRBO
Apartment in Simpson Bay Yacht Club located on the water
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We would love to welcome you to the Simpson Bay Yacht Club. A gated residence with 24 hours security, 2 swimming pools, ...
From $216 per night (USD)VRBO
- From $433 per night (USD)
Expedia
Rendezvous at Las Arenas
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
From the moment you set foot inside the luxurious, gated courtyard of Las Arenas in Sint Maarten, you know that this is ...
From $433 per night (USD)Expedia
- From $221 per night (USD)
VRBO
ENJOY THE BEAUTY OF ST MAARTEN BY STAYING RIGHT ON THE OCEAN IN LUXURY CONDO
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
LOCATED IN PELICAN KEY, the most desirable location in ST MAARTEN. One bedroom, one bath luxury condo. Sleeps 2. Living ...
From $221 per night (USD)VRBO
- From $6390 per night (USD)
VRBO
LUXURY COUACH 70 FT YACHT
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cohiba is from luxury french boat builder COUACH, kevlar deep V hull can handle easy and big space inside! Tunnel prope ...
From $6390 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Beach front 1 bedroom apartment overlooking Simpson Bay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This hotel is located next to the Simpson Bay Beach. Flamingo Beach Resort offers a restaurant, infinity-edge pool and f ...
From $150 per night (USD)VRBO
- From $679 per night (USD)
VRBO
Sol Y Mar (2/3 Rooms)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*** Only 2 out of 3 bedrooms and 2 bathrooms will be available for your use at this rate. The remaining bedrooms will be ...
From $679 per night (USD)VRBO
- From $679 per night (USD)
VRBO
Sol Y Mar Luxury villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sol Y Mar, a charming second-level private penthouse villa, nestled between a vibrant collection of favorite eateries, b ...
From $679 per night (USD)VRBO
- From $421 per night (USD)
VRBO
Palm Sea Views ground floor at La Siesta w/ backup generator; beach and sunset!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazingly remarkable apartment has tranquil Palm and Sea views from sunrise to sunset. It’s an astonishing space fo ...
From $421 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Coco Palm; Beach & Luxury!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Whether you are seeking a Peaceful Haven or Romantic Getaway, the 2 + miles of beautiful sandy Simpson bay beach situate ...
From $475 per night (USD)VRBO
- From $307 per night (USD)
Expedia
Waterfront Marina vacation Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, spacious Penthouse apartment on a Marina with lagoon waterfront views. Three bedrooms 2 bathrooms. Boat slip ...
From $307 per night (USD)Expedia
- From $298 per night (USD)
VRBO
Le Papillon Condo; Modern, Steps to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With direct access to the sand and sea, the Le Papillon condo is located in the brand new, and very upscale Le Papillon ...
From $298 per night (USD)VRBO
- From $2738 per night (USD)
VRBO
Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: BELLA VITA 6BR, Pelican Key, St Maarten Life is good at Villa Bella Vita, a sumptuous 7 bedroom contemporary ...
From $2738 per night (USD)VRBO
- From $1830 per night (USD)
VRBO
Bella Vita in Pelican Key by Personal Villas - Spacious and Sophisticated Villa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: BELLA VITA 4BR, Pelican Key, St Maarten Life is good at Villa Bella Vita, a sumptuous 7 bedroom contemporary ...
From $1830 per night (USD)VRBO
- From $532 per night (USD)
VRBO
Luxurious 2BR/2.5BA Unit on Simpson Bay Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled in an unbeatable location, this exquisite property offers modern luxury and stunning design. The spacious unit i ...
From $532 per night (USD)VRBO
- From $608 per night (USD)
VRBO
New Condo Eternal Sea
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
<p>A short distance from scuba diving, snorkeling, and more, this smoke-free vacation home lets you experience it all. F ...
From $608 per night (USD)VRBO
- From $214 per night (USD)
Expedia
B253 - Incredible Top Floor Lagoon Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
B253 - Deluxe 1 Bedroom with Lagoon View Discover your dream getaway at B253, a deluxe one-bedroom apartment perched on ...
From $214 per night (USD)Expedia
- From $204 per night (USD)
VRBO
B224 - Amazing Lagoon-View Apartment with Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Hills Residence Vacation Rentals' Apartment B224! Step into a realm of luxury and elegance with our stun ...
From $204 per night (USD)VRBO
- From $210 per night (USD)
Expedia
B226 - Amazing Lagoon View with Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Apartment B-226 at The Hills Residence Vacation Rentals! Step into a world of luxury and elegance with our ...
From $210 per night (USD)Expedia
- From $177 per night (USD)
VRBO
1-bedroom condo in amazing Simpson Bay Pool Steps from the beach, with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay comfortably in Simpson Bay at this 1-bedroom 1 and 1/2 bath Condo. This beautiful property comes equipped with ever ...
From $177 per night (USD)VRBO
- From $208 per night (USD)
Expedia
B255 - Beautiful Top Floor With Lagoon View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Apartment B255 at The Hills Residence in Simpson Bay, Sint Maarten—your luxurious lagoon retreat awaits! We a ...
From $208 per night (USD)Expedia
- From $136 per night (USD)
VRBO
Heavenly Haven - Royal Retreats Maho
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to this charming condo in Sint Maarten. This awesome rental offers 1 bedroom, complete with all the essentials l ...
From $136 per night (USD)VRBO
- From $522 per night (USD)
Expedia
Sunny Days at Simpson Bay Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your slice of paradise located in the prestigious Simpson Bay Yacht Club, one of Saint Maarten’s most sought- ...
From $522 per night (USD)Expedia
- From $225 per night (USD)
VRBO
B257 - Wonderful 1 bedroom with view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover your perfect getaway at the Hills Residence - Simpson bay Step into this stunning one-bedroom apartment, perche ...
From $225 per night (USD)VRBO
- From $518 per night (USD)
Expedia
Dream Beachfront Home : Stunning sea views, private pool and walking distance
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
<p>Located in Simpson Bay, this welcoming vacation home brings it all within your reach. There's convenient onsite parki ...
From $518 per night (USD)Expedia
- From $315 per night (USD)
VRBO
*New* SeaBliss 3BR Palm Beach Condo. Simpson Bay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to your dream Caribbean getaway at Palm Beach Condos, a luxurious and spacious 3-bedroom, 3.5-bathrooms ...
From $315 per night (USD)VRBO
- From $343 per night (USD)
Expedia
SeaRenity Apartment with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to our stunning 2-bedroom apartment with a private pool, perched high in the vibrant Simpson's Bay! Exp ...
From $343 per night (USD)Expedia
- From $220 per night (USD)
VRBO
SeaShores Beach Front 1 Brm Apt With Generator
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Welcome to your perfect getaway in Simpson Bay, Sint Maarten! This brand-new, modern 1-bedroom apartment offers ...
From $220 per night (USD)VRBO
- From $149 per night (USD)
Expedia
Family Room 12 with AC and Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Cozy Queen Room with Convertible Couch and Private Bath Relax in this comfortable and well-appointed queen roo ...
From $149 per night (USD)Expedia
- From $251 per night (USD)
VRBO
SeaWaves Beachfront 1 Brm Apt with Generator
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Escape to paradise in this charming 1-bedroom beachfront apartment located in the heart of Simpson Bay, Sint Ma ...
From $251 per night (USD)VRBO
- From $139 per night (USD)
Expedia
Comfort Room 6 with AC and Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Cozy Queen Room with Private Bath. Relax in this comfortable and well-appointed queen room, ideal for solo tra ...
From $139 per night (USD)Expedia
- From $125 per night (USD)
VRBO
Newly Renovated Pelican Key Studio.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Pelican Key is the most desirable areas on the island and a close walk to all of the island amenities on the “Strip “. A ...
From $125 per night (USD)VRBO
- From $348 per night (USD)
VRBO
3 Sea Vistas, Palm Beach Condos, Simpson Bay Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The condo, located in Palm Beach Apartment complex is a beautiful 2-level, 2-bedroom and 2.5 bathroom condo right on gor ...
From $348 per night (USD)VRBO
- From $135 per night (USD)
VRBO
Comfort Room 9 with AC and Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Cozy Queen Room with Private Bath. Relax in this comfortable and well-appointed queen room, ideal for solo tra ...
From $135 per night (USD)VRBO
- From $424 per night (USD)
Expedia
SeaHeaven 3BR Beachfront Penthouse With Generator
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Experience the ultimate Caribbean getaway in this luxurious 3-bedroom beachfront apartment, perfectly situated ...
From $424 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Comfort Room 4 with AC and Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Cozy Queen Room with Private Bathroom. Relax in this comfortable and well-appointed queen room, ideal for solo ...
From $135 per night (USD)VRBO
- From $315 per night (USD)
Expedia
SeaShells 2BR Beachfront Apartment with Generator
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Indulge in a luxurious beachfront escape at this modern 2-bedroom apartment, ideally located in the picturesque ...
From $315 per night (USD)Expedia
- From $294 per night (USD)
VRBO
Simpson Bay 2 bedr/2.5 bath apt
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this comfortable condo in Simpson Bay. It has 2 bedrooms with king size beds and ensuite bathrooms. There is a sep ...
From $294 per night (USD)VRBO
- From $458 per night (USD)
Expedia
Welcome to Peace of Mind - Spacious 3 bedroom apartment in Las Brisas, Cole Bay.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
COME STAY IN OUR PEACEFUL HAVEN Magnificent 3-master-bedroom apartment located near Juliana International Airport. A on ...
From $458 per night (USD)Expedia
- From $1416 per night (USD)
VRBO
Villa Impala, 5 bedroom villa beachfront in Simpson Bay, Sint Maarten
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Villa Impala offers one of the most unbeatable locations in St. Maarten. At the water's edge on Simpson Bay, it is part ...
From $1416 per night (USD)VRBO
- From $119 per night (USD)
VRBO
Hillside Haven in Simpson Bay: Cozy Cottage with Stunning Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perched on a charming hillside, this cozy, budget-friendly one-bedroom cottage offers an ideal retreat for business trav ...
From $119 per night (USD)VRBO
- From $227 per night (USD)
VRBO
B206 - Magnificent 1 bedroom with terrace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Apartment B206 at The Hills Residence – Your Luxurious Oasis in Simpson Bay, Sint Maarten Discover an exceptional geta ...
From $227 per night (USD)VRBO
- From $212 per night (USD)
Expedia
A121 - Condo with amazing view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover this amazing one-bedroom apartment at The Hills Residence, located in Simpson Bay, Sint-Maarten! Perched on the ...
From $212 per night (USD)Expedia
- From $204 per night (USD)
VRBO
B217 - 1 bedroom with amazing view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to this splendid one-bedroom apartment at The Hills Residence, in Simpson Bay, Sint-Maarten! Located on the firs ...
From $204 per night (USD)VRBO
- From $206 per night (USD)
Expedia
B243 - Deluxe 1 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
B243 - Deluxe 1 Bedroom with Lagoon View Discover your dream getaway at B243, a deluxe one-bedroom apartment perched on ...
From $206 per night (USD)Expedia
- From $211 per night (USD)
VRBO
B237 - Cosy 1 Bedroom with Lagoon View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
B237 - Cosy 1 Bedroom with Lagoon View Discover your dream escape at B237, a charming one-bedroom apartment nestled on t ...
From $211 per night (USD)VRBO
- From $213 per night (USD)
Expedia
B213 - Deluxe 1 Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
B213 - Deluxe 1 Bedroom Apartment Discover your dream getaway at B213, a deluxe one-bedroom apartment conveniently locat ...
From $213 per night (USD)Expedia
- From $116 per night (USD)
VRBO
Le Coeur in the heart of SimpsonBay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Le Cœur De Simpson Bay offers accommodations in Simpson Bay, a 3-minute walk from Kim Sha Beach and 0.6 miles from Simps ...
From $116 per night (USD)VRBO
- From $276 per night (USD)
Expedia
Beachfront 1 Bedroom - Feet in the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your Caribbean vacation begins on one of the prettiest unspoiled beaches on all of St. Maarten / St. Martin. Quiet, cal ...
From $276 per night (USD)Expedia
- From $194 per night (USD)
VRBO
Cozy space, conveniently located just 10 minutes away from beaches, the airport.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This tranquil retreat offers a perfect balance of comfort and sophistication, making it an ideal getaway. Enjoy the conv ...
From $194 per night (USD)VRBO
- From $562 per night (USD)
VRBO
Peaceful Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Experience luxury island living in this fully furnished 4-bedroom, 4-bathroom villa in the prestigious gated community o ...
From $562 per night (USD)VRBO
- From $277 per night (USD)
VRBO
Spacious 3BD Home - Private Cozy Pool - Centrally Located - Quiet Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This modern 3-bedroom, 2.5-bathroom home is the perfect retreat for those seeking a luxurious yet cozy getaway. This hom ...
From $277 per night (USD)VRBO
- From $1911 per night (USD)
Expedia
PELICAN KEY BEACH VILLA
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Pelican Key Beach Villa is an exquisite, contemporary-styled vacation property that offers an idyllic setting for an unf ...
From $1911 per night (USD)Expedia
- From $245 per night (USD)
VRBO
A127 - Stunning 2-Bedroom Lagoon View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Apartment A-127 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury lagoon retreat awaits! We a ...
From $245 per night (USD)VRBO
- From $205 per night (USD)
Expedia
A115 - Incredible Lagoon View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Apartment A- 115 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury lagoon getaway awaits! We ...
From $205 per night (USD)Expedia
- From $226 per night (USD)
VRBO
A114 - Beautiful Lagoon View & Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Apartment A-114 at The Hills Residence in Simpson Bay, Sint Maarten - your first floor luxury oasis awaits! W ...
From $226 per night (USD)VRBO
- From $237 per night (USD)
Expedia
A101 - Outstanding Lagoon View & Garden
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the fabulous condo A-101 of The Hills Residence in Simpson Bay, Sint Maarten - your ultimate destination for ...
From $237 per night (USD)Expedia
- From $227 per night (USD)
VRBO
A134 - Panoramic View of the Lagoon
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Apartment 134 at The Hills Residence in Simpson Bay, Sint Maarten - your luxury third floor hideaway awaits! ...
From $227 per night (USD)VRBO
- From $217 per night (USD)
Expedia
Amazing Ocean views for this Simpson Bay Beachfront Condo in Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience Simpson Bay like a local in this 2-bedroom beach front condo with an unobstructed view of the ocean. The spac ...
From $217 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Gorgeous 1 bed- 1,5 bath apt in Simpson Bay - GENERATOR
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This gorgeous apartment is located in the best spot of the island. You have everything right at your doorstep. Of course ...
From $202 per night (USD)VRBO
- From $183 per night (USD)
Expedia
SIMPSON BAY YACHT CLUB NEW VERY LARGE STUDIO CONDO 872 SQFT IN THE HEART OF SXM!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Having owned a much larger villa on the island for 23 years which I rented to a lovely and respectful group of guests, I ...
From $183 per night (USD)Expedia
- From $468 per night (USD)
VRBO
2 Bedroom 2.5 Bath Penthouse on Simpson Bay Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Penthouse at Las Arenas is a 2 bedroom 2.5 bathroom penthouse located on St. Maarten’s longest beach – the Simpson B ...
From $468 per night (USD)VRBO
- From $104 per night (USD)
Expedia
Flamingo Beach by Hilton: Oceanfront Resort, Pools & Spacious Studios To Relax!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Flamingo Beach, a Hilton Vacation Club, where luxury, adventure, and relaxation combine to create the ultimat ...
From $104 per night (USD)Expedia
- From $91 per night (USD)
VRBO
Adorable Private Room with partial Sea View
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
On vacation or on business, forget your worries in this spacious and serene space. See the sunset from the balcony with ...
From $91 per night (USD)VRBO
- From $356 per night (USD)
VRBO
Le Bleu at Las Arenas
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Contemporary elegance at its best. Le Bleu, located in the exclusive Las Arenas complex, is a newly renovated ground flo ...
From $356 per night (USD)VRBO
- From $444 per night (USD)
Expedia
For Sunset Lover! Ocean view villa \"Sunset Heaven\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover your ideal beach getaway at our villa located in the prestigious Pelican residential area in Sint Maarten. With ...
From $444 per night (USD)Expedia
- From $467 per night (USD)
VRBO
Penthouse Suite La Siesta, beach and sunsets! Backup generator!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Spacious, elegant with an open floor plan and stunning, panoramic views of all Simpson Beach can be yours to enjoy!! Re ...
From $467 per night (USD)VRBO
- From $297 per night (USD)
VRBO
Condo on the beach La Siesta w/ backup generator; beach and sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A2 La Siesta Beach Condo is an oceanfront, ground floor, 1-bedroom condo directly on Simpson Bay Beach. A2 @ La Siesta ...
From $297 per night (USD)VRBO
- From $396 per night (USD)
VRBO
Sea Place at La Siesta
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you’re seeking a romantic getaway or a family vacation, white and sandy beach, or an amazing seafront dream….; t ...
From $396 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Villa Jade Pearl in Pelican; Sunset Views!!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful sunsets and relaxing days in Pelican. Enjoy your vacation lounging at your private pool or just stroll to the ...
From $370 per night (USD)VRBO
- From $277 per night (USD)
Expedia
Paradise Gem, ground floor on Simpson Bay Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Introducing the newly renovated PARADISE GEM directly on the pristine Simpson Bay Beach! The PARADISE GEM is luxurious ...
From $277 per night (USD)Expedia
- From $70 per night (USD)
VRBO
Cozy, Cole Bay, one bedroom with security and free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this calm, stylish, fully equipped and air conditioned space. The unit has been recently renovat ...
From $70 per night (USD)VRBO
- From $760 per night (USD)
Expedia
Villa Ladida - Luxurious Villa with Magnificent view
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous 4 bedroom - 4 bath villa is located right between Pelican and Simpson Bay. Also available as 6 bedroom!!!! ...
From $760 per night (USD)Expedia
- From $135 per night (USD)
VRBO
Comfort Room 10 with AC and Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Cozy Queen Room with Private Bathroom. Relax in this comfortable and well-appointed queen room, ideal for solo ...
From $135 per night (USD)VRBO
- From $616 per night (USD)
Expedia
Villa Turquoise Heaven
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this marvelous villa in Sint Maarten. This welcoming property boasts 3 bedrooms, including 2 king beds and 1 ...
From $616 per night (USD)Expedia
- From $608 per night (USD)
VRBO
Luxury Beachfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Luxury 2 bedroom unit at the prestigious Aqualina Beach Club directly on Simpson Bay beach. Unit 201 is ideal for one o ...
From $608 per night (USD)VRBO
- From $512 per night (USD)
Expedia
SeaViews 4Bedroom Penthouse with Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Experience luxury and comfort in our stunning 4-bedroom penthouse, perched elegantly above the pristine Kim Sha ...
From $512 per night (USD)Expedia