Old Prison Rentals by Owner
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Why Choose Rent By Owner for your Old Prison vacation rental?
What makes our Rentals by Owner special?
Popular Areas for Old Prison Rentals by Owner
Where are the best neighborhoods to stay in Old Prison?
Discover the charm of Old Prison in The Valley, Anguilla, where you can experience a peaceful and authentic Caribbean atmosphere. Staying in this neighborhood offers convenient access to local amenities and a tranquil environment, ideal for those seeking a relaxing getaway. As you explore options through Rent By Owner, you'll find a variety of rental properties that cater to your preferences, ensuring a seamless booking experience. Whether you're looking for a cozy retreat or a spacious villa, Old Prison provides a dependable base for your Anguilla adventure, all while enjoying the natural beauty and serene surroundings of The Valley.
Sea Rocks
Located in the picturesque area of Island Harbour, this neighborhood offers an authentic local experience just moments from your rental. Here, you can enjoy a tranquil atmosphere while staying within reach of the region's natural beauty.
View 149+ Rentals in Sea RocksBest Times to Visit Old Prison
When should you plan your Rentals by Owner stay?
Understanding the optimal times to visit can help you enjoy a more relaxing and enjoyable vacation here, making your experience in Old Prison, The Valley, Anguilla, truly memorable.
Peak Season Highlights
December to April
During this period, you can expect warm, sunny weather ideal for exploring the region’s outdoor attractions and enjoying the vibrant local culture. It is the most popular time to visit, so early booking is recommended.
July to October
This summer to early fall stretch offers hot temperatures and lively local events, making it an attractive season for visitors seeking a lively experience in the area. However, be mindful of the increased demand during these months.
Off-Season Highlights
May to June
In the late spring to early summer, fewer travelers arrive, giving you more tranquility and better rates while still enjoying pleasant weather in the region.
November
The late autumn period sees a slowdown in visitor numbers, offering a peaceful atmosphere for those looking to experience the destination without the crowds. It’s a perfect time to find excellent rental deals.
Weekly Weather Forecast for Old Prison
How to Book Your Old Prison vacation rental
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Old Prison
Common Rentals by Owner Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor swimming pool to relax and unwind in the warm Caribbean sunshine.
- Take advantage of spacious patios or decks perfect for al fresco dining or lounging with friends and family.
- Benefit from lush, landscaped gardens that create a serene outdoor environment just steps from your rental.
- Make use of outdoor barbecue grills to enhance your culinary experience during your stay here.
- Discover shaded seating areas or verandas ideal for enjoying the gentle breezes of the region.
- Have access to dedicated outdoor parking spaces to ensure convenience during your visit.
- Utilize outdoor showers or rinse stations to keep your gear clean after beach days along the coast nearby.
Top Attractions Around Old Prison
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of outdoor activities and explore nearby natural attractions that exemplify the beauty of Anguilla’s landscape, making your stay in this destination both memorable and engaging.
Family Activities
- Historical Tours at Old Prison: Explore the historic prison site to learn about the region’s rich history, providing an educational experience for the entire family.
- Nature Walks in The Valley: Enjoy scenic trails where you can immerse yourselves in the lush surroundings and native flora of this picturesque area.
- Local Market Visits: Discover local crafts and fresh produce, giving your family a taste of authentic Anguillan culture right here in the region.
- Beach Day at Nearby Shores: Relax and play on nearby beaches, ideal for building sandcastles and swimming in the calm waters suitable for families visiting here.
Adult Activities
- Historical Tours: Discover the rich history of the Old Prison through guided tours that offer fascinating insights into its past and unique architecture in The Valley.
- Photography Walks: Capture stunning photographs of the area's distinctive colonial buildings and scenic surroundings, perfect for photography enthusiasts visiting the region.
- Local Cuisine Experiences: Savor authentic Caribbean flavors at nearby eateries, immersing yourself in the culinary culture of this destination in Anguilla.
- Nature Excursions: Explore the lush landscapes and coastal scenery of the region on guided nature walks or eco-tours that highlight the area's natural beauty.
Old Prison Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining options: Take advantage of the region's authentic eateries to enjoy regional flavors and support small businesses during your stay.
- Plan outdoor excursions: Make the most of the area’s natural beauty by dedicating time to beach days, guided tours, or leisurely walks around the neighborhood.
- Connect with your host: Communicate openly with your rental owner to receive personalized tips and insights about the best spots and hidden gems nearby.
- Respect the community: Embrace the relaxed pace of this destination by observing local customs and maintaining a considerate attitude toward neighbors and surroundings.
Transportation Options
- Private Car Rentals: Renting a private vehicle here offers you the flexibility to explore the region at your own pace, making it ideal for travelers staying in rental homes by owner.
- Local Taxis: Reliable taxi services operate throughout the area, providing convenient transportation options for day trips and airport transfers.
- Official Buses: Public bus routes connect key parts of the region, offering an affordable way to navigate nearby attractions and amenities.
- Bike Rentals: For an eco-friendly and leisurely way to discover this destination, bike rentals are available, allowing you to enjoy scenic views around your rental property.
Local Customs Options
- Respect for Local Traditions: You will find that embracing the area's customs, such as local greeting gestures, enhances your connection to the community here in Old Prison, The Valley.
- Celebration of Cultural Events: Participating in regional festivals and observing traditional ceremonies can give you a deeper appreciation of this destination’s heritage.
- Dress Code Etiquette: When visiting communal or religious sites, dressing modestly is appreciated and shows respect for local customs along the region.
- Environmental Respect: Practicing responsible tourism by conserving natural resources and minimizing waste aligns with the community’s values here in Anguilla.
Frequently Asked Questions About Old Prison Rentals by Owner
1. What are the top vacation rentals in Old Prison?
There are a lot of options in Old Prison. If you plan on staying in the Old Prison area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Prison:
- Private; one of the best views on Anguilla; heated pool.
- Honeymooners! Romantic Private Anguilla Villa w/Pool, Ocean Views, Beach Access
- Shoal Bay Coastal Sanctuary, Anguilla, BWI
- DragonFly Studio, a charming place dedicated to relaxation
- Villa Tasha Luxury Seafront Villa in Anguilla on the Caribbean sea AMAZING!
- Water views, central location and infinity pool
- Penthouse Mimosa Great Views, Oceanfront Estate
- WONDERFUL APARTMENT ON TWO FLOORS WITH AIR-CONDITIONING NEXT TO THE SEA
- exquisite, rejuvenating, charming, private, elegant, beautiful sunset, luxury
- ON THE BEACH Luxury BeachHouse, sleeps 8, pool, hot-tub, fire-pit, …
2. How many Rentbyowner vacation rentals are available in Old Prison?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 204 in the Old Prison area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Old Prison.
3. What is the cancellation policy for rentals by owner in Old Prison, The Valley?
4. How do I confirm my booking at a rental by owner here?
5. Are there any additional fees I should be aware of when booking a rental here?
6. Can I communicate directly with the property owner before booking?
7. What amenities can I expect when staying in a rental by owner in this area?
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