Penna holiday rentals

We found 740 holiday rentals — enter your dates for availability
Discover a selection of 10 apartments and other holiday rentals in Penna that are perfect for your trip. Holiday homes provide the amenities that you need and want for your stay with friends, family or just your pet, such as air conditioning and a pool. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Why visit Penna

  • Historic Landmarks: Explore charming castles and quaint churches that echo Penna's rich history.
  • Piazza Culture: Relax in picturesque piazzas, ideal for soaking in local culture and ambience.
  • Scenic Vistas: Enjoy breathtaking views of the Tuscan landscape, perfect for outdoor enthusiasts.
  • Romantic Ambience: Experience a blend of historical charm and tranquility for a romantic escape.
  • Local Heritage: Immerse yourself in the friendly local culture and traditional Tuscan lifestyle.

Popular types of accommodation in Penna

Welcome to Penna, Terranuova Bracciolini, Tuscany, Italy – a charming destination offering a variety of holiday rentals. Explore cosy apartments, elegant villas, and private holiday homes, each promising comfort and local charm. Enjoy the rich heritage and scenic beauty that Penna has to offer, with attractions and experiences unique to this historic town. Discover the best homes in Terranuova Bracciolini and make your stay memorable with a perfect penna house or penna apartment.

  • Apartments: A preferred choice for visitors, these self-contained units offer the comfort of home, often with kitchens and living areas.
  • Villas: Ideal for those seeking luxury and space, these elegant properties typically feature gardens and stunning views.
  • Private Holiday Homes: Perfect for families or groups, these homes provide privacy and a homely atmosphere.
  • Caravan Parks: A fun and affordable option, these parks offer a variety of caravan and camping spots amidst nature.
  • Lodges: Set in scenic locations, these charming accommodations provide a rustic experience with essential amenities.**

Top attractions near Penna

Penna, located in Terranuova Bracciolini, Tuscany, is a charming destination perfect for romantic escapes and outdoor adventures. Visitors can explore captivating landmarks such as historic castles and quaint churches, while the picturesque piazzas provide ideal spots for relaxation and cultural immersion. Whether you're seeking a vibrant city experience or a tranquil retreat, Penna offers a delightful blend of history and natural beauty for all travellers.

  • Castello di Albola: This enchanting castle exudes a sense of romance and rich cultural heritage. Nestled in the Tuscan hills, it offers stunning views and a glimpse into the region's medieval history.
  • Franciscan Monastery of St. Francis: A serene sanctuary, this monastery invites visitors to explore its peaceful surroundings and appreciate its significant cultural value, reflecting the spiritual traditions of the Franciscan order.
  • Piazza Guido Monaco: A vibrant square in the heart of the city, Piazza Guido Monaco is a hub of activity, brimming with local culture, delightful cafes, and the charm of Tuscan life.

Things to do recommended for couples

Discover Tuscany's charm in Penna, Terranuova Bracciolini. Enjoy leisurely walks through historic streets, savour local cuisine and explore romantic vineyards. Experience authentic Italian romance in a picturesque setting. Ideal for couples seeking a memorable getaway.

Things to do recommended for families

In Penna, families can explore vibrant local markets, savour authentic Tuscan gelato, and participate in traditional cooking classes, while admiring scenic countryside vistas within a short stroll.

Things to do recommended for groups

Embark on an adventure at Saltalbero Adventure Park, a zipline ropes course 31km from Penna, and relish the spirit of local outdoor fun with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Penna

Whether you’re journeying with a group, as a family, with your pets, or seeking extended stays, ensure you select the appropriate filters. Here are some Stayz booking pointers for you.

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

Where to stay in Penna

Penna in Terranuova Bracciolini offers an enchanting retreat with its romantic, outdoor ambience and friendly locals. The village is nestled amid the captivating Tuscan landscape, inviting visitors to explore its charming streets, scenic vistas, and relaxed atmosphere. Ideal for a romantic and entertainment-themed holiday, Penna showcases the quintessential allure of Tuscany.

  • Terranuova Bracciolini: Nestled in the heart of Tuscany, Terranuova Bracciolini offers travellers an enticing blend of outdoor adventures, romantic escapes and cultural insights. As the local hub, Penna is nestled within its bounds, giving visitors easy access to bustling shopping centres, refined shopping mall centres and exclusive country private clubs. Historic landmarks, serene lakes and charming places of worship add to the town’s rich tapestry, inviting you to immerse yourself in its storied past and vibrant present.
  • Loro Ciuffenna: Just 3km away, Loro Ciuffenna is a delightful city that promises a romantic and entertaining escapade with a dash of outdoor charm. This destination is well-known for its rejuvenating spas, indulgent body treatments and scenic golf courses. Wander through areas dotted with historic buildings, ancient monuments and other notable historic places, each contributing to a captivating narrative that makes every visit a memorable experience.
  • Montevarchi: Situated 6km away, Montevarchi caters to families and city enthusiasts alike with a mix of urban attractions and leisure activities. Enjoy a day out at the local shopping centres and shopping mall centres or unwind with a relaxing spa session. The area also boasts historic sites, picturesque lakes and verdant parks, offering a well-rounded experience that blends modern entertainment with a touch of historical allure.

Booking with Stayz is a breeze

Are you hoping to save on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Stayz property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s Trip Board provides a dedicated space to plan new journeys, continue your existing plans, or review and organise your bookings. Properties you have saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

Explore the natural setting in Penna

Learn about the unique charm of Penna with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Penna

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Penna a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Badia a Coltibuono (9.4 mi / 15.2 km)
  • Castello di Albola (10.9 mi / 17.5 km)
  • Cantalici Winery (11.5 mi / 18.5 km)
  • Villa a Sesta Polo Club (12.6 mi / 20.3 km)
  • Castello di Radda Winery (13 mi / 20.9 km)
  • Borgo di Vescine - Tenute di Castelvecchi (13.3 mi / 21.4 km)

Exploring the natural landscape of Penna

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Penna is a great place to get out in nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Piazza Guido Monaco (15.2 mi / 24.5 km)
  • Arno River (22.3 mi / 35.9 km)
  • Valle dell'Inferno e Bandella (4 mi / 6.4 km)
  • Riserva Naturale Regionale Valle dell'Inferno e Bandella (4.5 mi / 7.3 km)
  • Gianfranco Carla Fineschi Botanical Rose Garden (5.9 mi / 9.4 km)
  • Area Naturale Protetta di Interesse Locale Arboreto Monumentale di Moncioni (7.9 mi / 12.8 km)

Travelling to and around Penna

The nearest airport is in Peretola Airport (FLR), located 26.1 mi (42 km) from the city centre.

Frequently asked questions

What is the best area to stay in Penna when booking a holiday rental?
When considering a holiday rental in Penna, Tuscany, the best area to stay is the charming village itself, which offers an authentic Tuscan experience. Nestled amidst the picturesque rolling hills, Penna boasts stunning views and a serene atmosphere that captures the essence of rural Italy.The village is relatively small, with a limited number of properties available, allowing for a more intimate and peaceful getaway. One of the top attractions nearby is the beautiful Church of San Giovanni Battista, which showcases remarkable architecture and provides a glimpse into the region's rich history. Additionally, the surrounding countryside is superb for scenic walks and hikes, with trails that lead through vineyards and olive groves, offering a chance to immerse oneself in the stunning landscape.Another point of interest in close proximity is the historic town of Volterra, renowned for its medieval architecture and Etruscan heritage. This makes Penna an ideal base for exploring both the immediate area and the broader Tuscan region.
What are the top attractions in Penna?
In Penna, Tuscany, visitors can immerse themselves in a tranquil atmosphere surrounded by stunning landscapes. The town itself boasts charming medieval architecture, with narrow winding streets and quaint stone houses that capture the essence of Tuscan life.Nearby, the picturesque village of Castellina in Chianti offers breathtaking views of the Chianti hills and is famous for its wine production. The local wineries often welcome visitors for tours and tastings, making it a superb spot for wine enthusiasts.For those interested in history, the nearby town of Volterra is a must-visit, known for its Etruscan origins and well-preserved medieval structures. The Roman Theatre and the stunning Palazzo dei Priori are highlights worth exploring.Nature lovers can enjoy the beautiful hiking trails that weave through the surrounding countryside, where the rolling hills and vineyards create an idyllic backdrop. The scenic routes provide opportunities for peaceful walks and photography, making this area a gem for outdoor activities.
Are all fees included in the Penna holiday homes prices shown on Stayz?
Stayz 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.
Are there any Penna holiday homes with parking?
Stayz offers a wide selection of holiday homes in Penna 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 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.
Are there any discounts for Penna holiday homes?
You can find great discounts on holiday homes in Penna on Stayz, 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 change or cancel my Penna holiday home booking on Stayz?
To find Penna holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Penna?
A long-stay holiday home in Penna 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Penna holiday home?
Book your Penna holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Penna?
Prices for holiday homes in Penna 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Penna to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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