A trip to Castle of Oliveto makes history come alive. Stare up at its mighty walls and pull out your guidebook to find out about its once-great power.

You'll have sightseeing choices galore when in Castelfiorentino. Castle of Oliveto is a good place to start here, but there are many other fine places to consider. Montegufoni Castle, Castello Sonnino, and Casa del Boccaccio are not far from the fortified complex and will round out your day nicely.

Plan a trip to see Castle of Oliveto

Price found within the past 48 hours. Click for updated prices.

Hotel Palazzo San niccolò & Spa

$653

per person

Jan 14 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

18.4/10 Exceptional! (175 reviews)

The property is beautifully old but be careful how much luggage you bring as there is no elevator, Only stairs. Room is nice. Bathrooms nicely updated. No complaints!

Reviewed on Sep 30, 2025

Hotel Regency

Historic Centre of Florence

$1,517

per person

Jan 5 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

18.8/10 Exceptional! (439 reviews)

Loved it! Great place and very convenient

Reviewed on Jul 4, 2025

Villa Cora

Oltrarno

Save 100% on your flight

$2,209

per person

Jan 3 - Jan 9

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Florence (FLR)

19.6/10 Exceptional! (467 reviews)

Nice property and staff.

Reviewed on Nov 13, 2025

Browse tours and tickets to explore Castle of Oliveto

Tours & day trips

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Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

Free cancellation available

Classes & workshops

See all 32 activities

Private Ceramics Course in Tuscany

Free cancellation available

Adventure & outdoor

See all 4 activities

Private Tuscan meal with Wine and EVO oil tasting

Free cancellation available

Popular places to visit

Teatro del Popolo

You can make plans for a show at Teatro del Popolo during your stay in Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area.

Benozzo Gozzoli Museum

You can spend an afternoon studying the exhibits at Benozzo Gozzoli Museum in Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area.

Tenuta Maiano

You can enjoy a tasting or tour at Tenuta Maiano during your travels to Montespertoli. Discover the beautiful countryside and wineries in this quaint area.

Agricola Tamburini Emanuela

You can enjoy a tasting or tour at Agricola Tamburini Emanuela during your travels to Gambassi Terme. Discover the beautiful countryside and wineries in this quaint area.

Church of Saint Jacob and Saint Philip

Church of Saint Jacob and Saint Philip is just one of the places to see in Certaldo, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and wineries in this culturally rich area.

Museum of Sacred Art

You can study the exhibits at Museum of Sacred Art, a museum with a storied past, during your trip to Certaldo. Discover the beautiful countryside and wineries in this relaxing area.