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Rolling hills, vineyards, and scattered buildings in a hilly landscape.

Castelfiorentino Vacation Rentals

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    • Check prices for these dates

    Check prices for these dates, December 14 – 15, 2026

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    Our top choices for Castelfiorentino vacation rentals

    1. Agriturismo “Fattoria Bellosguardo”, 'mangiatoia' apartment

    An outdoor dining area with a table set for breakfast, surrounded by greenery and a flowering bush.

    2. La Coccinella - Relaxation, Private Courtyard

    A modern living room with a flat-screen TV, a dining area with a table and chairs, and a kitchen with white cabinets and stainless steel appliances.

    3. New Listing

    A modern kitchen with white cabinets, a microwave, and a dining area with a round table and chairs.

    4. B&B La Fonte del Machiavelli

    An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

    5. Villa il Fedino

    An arched entrance with a lantern above, flanked by two potted plants.

    6. Relais Villa Olmo - Place of Charme

    A spacious indoor area with arched windows, wooden furniture, and hanging plants.

    7. Palazzo Pacini

    An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

    8. hu Firenze Certosa camping in town

    A water park with a pool, slides, and a wooden deck area.

    9. Apartment in San Gimignano in the city center for 4 people with fast Wi-Fi and concierge service.

    A narrow alleyway with brick walls, wooden barrels, and potted plants.

    10. Fattoria il Milione Agriturismo

    A swimming pool with lounge chairs and a flag.

    11. Marignolle Relais and Charme

    A modern house with glass walls and a patio area.

    12. La Locanda di Pietracupa

    A dining area with a table set for two, featuring a view of greenery through a window.

    13. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

    An outdoor patio with a table, chairs, and a view of a landscape.

    14. I Vivai

    An aerial view of a hotel with a swimming pool, outdoor seating, and a landscaped garden.

    15. Hu Firenze Camping In Town

    An outdoor dining area with multiple tables and chairs, surrounded by plants and hanging lights.

    16. Terre di Baccio

    A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

    17. Signoria Collection

    A historic building with ornate iron gates, potted plants, and a visible staircase leading to an upper floor.

    18. Teatro Luxury Apartments Firenze - Starhotels Collezione

    A rooftop pool with a clear view of historic buildings and mountains in the background.

    19. Villa La Stella - Casa per Ferie

    A terrace with a table set for breakfast, a chair, and a large umbrella.

    20. Relais Piazza Signoria

    A balcony with a table, wine glasses, and a bottle, overlooking a historic building with a clock tower and another tower.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Top Castelfiorentino Hotel Reviews

    La Cisterna

    A table set for dining with a view of a vineyard.

    Art Hotel Villa Agape - Place of Charme

    A formal garden with neatly trimmed hedges, a central fountain, and stone pathways.

    Villa Neroli - Place of Charme

    A large, multi-story building with a courtyard, surrounded by greenery and trees.

    The Social Hub Florence Belfiore

    A rooftop terrace with solar panels, outdoor seating, and a central sculpture.

    Hotel Ville sull'Arno - Preferred Hotels & Resorts

    A pool area with lounge chairs and umbrellas, surrounded by lush greenery and white flowers.

    Hotel David

    A courtyard with outdoor seating, potted plants, and a statue.

    Il Malaspina - Place of Charme

    A reception area with a check-in counter, a green door, potted plants, and a framed picture on the wall.

    The Hoxton, Florence

    A neatly made bed with white linens, a pink upholstered headboard, and a bedside table with a lamp.

    Villa Olmi Firenze

    A spacious living room with a high ceiling, comfortable seating, and large windows offering a view of the outdoors.

    Hotel Villa Betania

    An aerial view of a residential area with houses surrounded by lush greenery, a clear sky, and distant mountains.

    Wyndham Garden Florence

    A spacious dining area with multiple tables and chairs, large windows, and pendant lighting.

    Hotel Cosmopolitan

    The entrance of the Cosmopolitan hotel with a curved glass facade and a sign above the entrance.

    Radisson Blu Hotel, Florence

    A modern lounge area with a sofa, dining table, chairs, and a view of outdoor umbrellas and a pool.

    IQ Hotel Firenze

    A modern hotel with a glass facade, a rooftop pool, and multiple balconies.

    The Market Urban Hotel

    A building with three arched windows, each displaying a sign that reads "THE MARKET".

    Solo Experience Hotel

    A spacious lobby with a reception desk, seating area, and large windows.

    The Social Hub Florence Lavagnini

    A modern bar area with a view of a cityscape and a pool.

    Hotel Horto Convento

    A modern restaurant with colorful chairs and tables, large windows, and potted plants.

    Find out more about Castelfiorentino

    Everything you need to know about Castelfiorentino vacation rentals

    Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castelfiorentino vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castelfiorentino vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Castelfiorentino vacation rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Castelfiorentino. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castelfiorentino in high season.

    Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $49 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

    How to find incredible deals on Castelfiorentino rentals

    At Expedia, we put the best Castelfiorentino vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Castelfiorentino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castelfiorentino vacation.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castelfiorentino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Can I find a vacation rental in Castelfiorentino?

    Yes, we give you a choice of vacation rentals near top attractions in Castelfiorentino, or you can choose a secluded option if you want a relaxing place to stay. Our travelers say Castelfiorentino has a good selection of restaurants. Make sure you have time to check out the theaters and wineries during your trip.

    What are some of the best vacation home rentals in Castelfiorentino?

    Villa La Stella - Casa per Ferie: This vacation home rental outside of Castelfiorentino is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

    How many vacation rentals are there in Castelfiorentino?

    Expedia has 9 vacation rentals for your stay in Castelfiorentino.

    What can I see and do in Castelfiorentino?

    Cultural attractions to visit include Benozzo Gozzoli Museum and Teatro del Popolo. Other places in town to visit include Castle of Oliveto and Castello di Coiano.

    What are vacation rentals like in Castelfiorentino?

    Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Castelfiorentino. Vacation rentals offer amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.

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