Little Bay holiday lettings

We found 3,290 holiday rentals — enter your dates for availability
Discover a selection of 12 apartments, 12 villas and other holiday rentals in Little Bay that are perfect for your trip. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as parking and a fireplace. What you'll find is a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Little Bay

Showing deals for:6 Nov - 13 Nov

Image gallery for 4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

Pool
9.8 out of 10, Exceptional, (65 reviews)
Exceptional
(65 reviews)

4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

Simpson Bay

5% off
Price is £4,117
for 7 nights, 1 villa
£588 per night
includes taxes & fees
4 bedroom Pelican Key Private Luxury Villa, Panoramic View Of The Caribbean Sea

Find spaces that suit your style

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Why visit Little Bay

  • Picturesque Beaches: Soak up the sun on the stunning Little Bay Beach, perfect for relaxation and water activities.
  • Historic Exploration: Discover the rich history by visiting nearby historic forts and landmarks.
  • Charming Streets: Wander through the quaint streets of Little London, filled with local shops and culture.
  • Outdoor Adventures: Enjoy various outdoor activities, from hiking to water sports, amidst breathtaking scenery.
  • Varied Accommodation: Choose from a range of holiday rentals, from luxurious villas to cosy apartments, catering to all preferences.

Popular types of accommodation in Little Bay

Little Bay offers a delightful selection of holiday rentals to suit every traveller's needs. From modern condos and luxurious villas to cosy apartments, you'll find the perfect base for your getaway. Whether you're seeking a seaside retreat or a vibrant urban experience, our rental properties in Little Bay provide the ideal blend of comfort and convenience. Explore the best options for your next holiday in this charming destination.

  • Condos: The top choice for visitors to Little Bay, offering a blend of comfort and convenience, perfect for a relaxing getaway.
  • Villas: A luxurious option for those seeking privacy and spacious living, ideal for families or groups.
  • Apartments: A popular choice that provides a home-like atmosphere, suitable for both short and extended stays.
  • Houses: A great alternative for travellers wanting a unique experience with all the comforts of home.
  • Guest Houses: An inviting option, perfect for a more personal touch and a chance to connect with local culture.**

Top attractions in and around Little Bay

Little Bay in Philipsburg, Sint Maarten, is ideal for a beach and outdoor getaway, offering stunning scenery and cultural experiences. Visitors can enjoy the picturesque Little Bay Beach, explore historic forts, and relax in local parks. Whether you're seeking adventure or relaxation, this charming destination caters to all. Don't miss the chance to soak up the sun and immerse yourself in the vibrant culture. For more information, check the links for Little Bay Beach.

  • Great Bay Beach: A stunning stretch of soft sand located 373m from Little Bay, Great Bay Beach is perfect for soaking up the sun, swimming in crystal-clear waters, and enjoying a vibrant beach atmosphere.
  • Fort Amsterdam: Nestled within Little Bay, Fort Amsterdam is a historic fortress that offers a glimpse into the island's rich cultural heritage, featuring impressive architecture and panoramic views of the surrounding area.
  • Seaside Nature Park: Located 1.50m away, this eco-friendly park provides an excellent outdoor experience for families, with opportunities for hiking, bird watching, and exploring the island's natural beauty.

Things to do recommended for couples

For a romantic escape in Little Bay, Philipsburg, take a leisurely stroll along the picturesque Philipsburg Boardwalk, just 1.6km away. Enjoy the vibrant beach atmosphere and the stunning views, perfect for couples seeking a memorable experience together.

Things to do recommended for families

Your family will delight in the exciting experiences at Rainforest Adventures St. Maarten, located 621m from Little Bay. This recreation park offers a perfect blend of wellness and relaxation, making it an ideal spot for family-friendly fun and unforgettable memories.

Things to do recommended for groups

Experience a round of golf at Mullet Bay Golf, located 2.5km from Little Bay, perfect for enjoying the outdoors with your group. Alternatively, relax on the beautiful beaches or explore local eateries for a taste of authentic Caribbean cuisine.

What do I need to keep in mind when booking a vacation in 'Little Bay

When planning your trip, whether you're travelling with a group, a family, or your pets, or if you're seeking extended stays, it's essential to filter according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Little Bay with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Little Bay with young kids: Embarking on a journey with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Little Bay: For many, a family holiday isn’t truly finished without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Little Bay: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Little Bay

Little Bay, Philipsburg, offers a delightful blend of beach relaxation and outdoor adventures. Visitors can soak up the sun on Little Bay Beach, enjoy stunning views from Little Bay View, and explore the charming streets of Little London. For those seeking a romantic getaway, nearby villas provide the perfect retreat. With its picturesque scenery and laid-back atmosphere, Little Bay is an ideal destination for a memorable holiday experience.

  • Philipsburg: Philipsburg is a vibrant city located 621m from Little Bay, renowned for its stunning beaches and vibrant outdoor life. Visitors flock to this lively locale for its picturesque boardwalk, where you can enjoy a leisurely stroll alongside the turquoise waters. The city's attractions include a variety of educational opportunities and luxurious resorts, making it a perfect spot for relaxation and exploration. Notable landmarks include the beautiful beaches and the scenic bay, which serve as ideal settings for sunbathing and water sports.
  • Cay Bay Hill: Situated just 311m from Little Bay, Cay Bay Hill is a charming village that offers a serene escape with breathtaking scenery. This area is popular among tourists seeking beach experiences and outdoor activities. The village features a delightful boardwalk and educational venues, as well as several resorts for accommodation. The proximity to stunning beaches and the inviting bay makes Cay Bay Hill a perfect destination for those looking to unwind while enjoying the natural beauty of the area.
  • Belair: Belair is a picturesque neighbourhood nestled around Little Bay, attracting visitors with its scenic views and tranquil beaches. This area is renowned for its welcoming resorts and engaging boardwalk, making it an excellent choice for those seeking both relaxation and recreation. The nearby nudist beach and bay add to the allure, providing unique opportunities for sun-seeking adventurers. With its laid-back atmosphere, Belair is a wonderful spot to enjoy the picturesque coastal landscape of Sint Maarten.

Best time to go to Little Bay

If you're planning a trip to Little Bay, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs in March to April and September, while off-peak times, like May and October to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High
February76.1°F (24.5°C)No Rain (Dry)Mostly SunnyAverageAverage
March76.3°F (24.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April77.0°F (25.0°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May78.4°F (25.8°C)Light RainMostly SunnySlightly LowAverage
June79.9°F (26.6°C)Light RainMostly SunnyAverageAverage
July80.4°F (26.9°C)Light RainMostly SunnyAverageAverage
August81.0°F (27.2°C)Light RainMostly CloudyAverageAverage
September81.3°F (27.4°C)Light RainMostly SunnySlightly HighSlightly Low
October80.8°F (27.1°C)Light RainMostly CloudySlightly LowSlightly Low
November79.5°F (26.4°C)Light RainMostly CloudySlightly LowSlightly Low
December78.1°F (25.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, booking a longer stay frequently results in significant savings. To discover the ideal Vrbo property that suits your budget, make use of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated area for you to plan new adventures, refine your arrangements, or manage your existing bookings. The properties you've saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Book a holiday rental for your Little Bay getaway

Learn about the unique charm of Little Bay with a stay in a holiday home rental. This city has something for everyone. Maho Beach and Mullet Bay Beach are just a couple of the must-see attractions in the area. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in and around Little Bay

Are you hoping to discover things to do in the area? Venture out of your cosy holiday rental and experience everything that makes Little Bay a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Mullet Bay Golf (3.8 mi / 6.2 km)
  • Aurora International Golf Club (11.1 mi / 17.9 km)

Exploring the natural features in Little Bay

Whether you're looking for adventure or just want to spend some time taking in the scenery, Little Bay is a great place to get outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Maho Beach (3.8 mi / 6 km)
  • Mullet Bay Beach (4.3 mi / 7 km)
  • Little Bay Beach (0.6 mi / 1 km)
  • Great Bay Beach (0.6 mi / 1 km)
  • Kim Sha Beach (1.9 mi / 3.1 km)
  • Flamingo Beach (2.1 mi / 3.3 km)

Transport to and around Little Bay

Fly into Philipsburg (SXM-Princess Juliana Intl.), the closest airport, located 3.3 mi (5.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Grand Case (SFG-L'Esperance), which is 5.3 mi (8.6 km) away.

Frequently asked questions

What is the best area to stay in Little Bay when booking a holiday rental?
When considering a holiday rental in Little Bay, Sint Maarten, a popular area to stay is near the picturesque beach itself. This neighbourhood offers a delightful blend of relaxation and convenience, with a variety of properties available that cater to different preferences and budgets. You can find charming villas and condos that provide stunning views of the Caribbean Sea, ensuring you enjoy the beauty of the island from the comfort of your accommodation.

In addition to the beautiful beach, Little Bay is conveniently located near several attractions. For instance, the historic Fort Amsterdam is just a short distance away, offering a glimpse into the island's historic past along with breathtaking views. Another nearby highlight is the vibrant Kimsha Beach, which is known for its lively option, water sports, and numerous beach bars where you can enjoy local cuisine and refreshing drinks.

Staying in Little Bay not only places you right by the beach but also provides easy access to the vibrant culture and activities that Sint Maarten has to offer.
How much does it cost to rent a holiday home in Little Bay?
Prices for holiday rentals in Little Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Little Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Little Bay holiday house rentals?
You can find great discounts on house rentals in Little Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay holiday rentals in Little Bay?
A long-stay holiday rental in Little Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Little Bay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Little Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Little Bay for a holiday rental?
The best time to visit Little Bay for a holiday rental is during September, when the weather is still pleasantly warm and it's less busy. This month allows you to enjoy the beautiful beaches and vibrant local culture without the hustle and bustle of peak tourist season, which runs from July to September.

In September, you can expect average temperatures hovering around 27-30 degrees Celsius, making it ideal for both beach lounging and outdoor activities like snorkeling and hiking in the lush surroundings. The calm waters and sunny skies provide a great backdrop for exploring the stunning coastline or indulging in some water sports.

For those looking for a more budget-friendly option, October marks the beginning of the low season. While the weather remains fantastic, you can often find great deals on holiday rentals during this quieter time. Exploring Little Bay in October allows you to experience the area at a more relaxed pace, with fewer visitors and an opportunity to interact more closely with the local community.
How early should I book a Little Bay holiday rental?
Book your Little Bay holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Little Bay?
In Little Bay, Sint Maarten, visitors can enjoy a variety of attractions that highlight the area's natural beauty and vibrant culture. The stunning Little Bay Beach is a central draw, offering soft sands and crystal-clear waters ideal for swimming and sunbathing. Nearby, Fort Amsterdam provides a glimpse into the island's history with its well-preserved ruins and panoramic views of the coastline.

For those interested in water activities, the area around Little Bay is great for snorkelling and diving, with several operators offering excursions to explore the rich marine life. Additionally, the Great Bay Beach, just a short distance away, features a lively promenade with shops and restaurants, making it a great spot for dining and entertainment.

Cultural enthusiasts might enjoy visiting the nearby capital, Philipsburg, where colourful buildings, local markets, and the St. Maarten Museum can be found, providing insights into the island's heritage.
Can I change or cancel my Little Bay home rental booking on Vrbo?
To find Little Bay holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Little Bay holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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