San Prospero Vacations from $1,456
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The Latest San Prospero Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Monastero di Cortona Hotel & Spa
Cortona Old Town
Save 100% on your flight
Price was $2,080, price is now $1,456 per person
$1,456
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (230 reviews)
Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect
Reviewed on Aug 7, 2025
L'Andana
Save 100% on your flight
Price was $2,626, price is now $1,752 per person
$1,752
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (80 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.
Reviewed on Jul 5, 2025
The Club House
Save 100% on your flight
Price was $2,450, price is now $1,717 per person
$1,717
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (2 reviews)
Excellent overall. Amenities. Service. Food. Vibe. All top notch
Reviewed on Sep 2, 2025
Castello di Spaltenna- Small Luxury Hotels of the World
Save 100% on your flight
Price was $2,456, price is now $1,739 per person
$1,739
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (247 reviews)
This was the most authentic place I have ever seen really takes back but all the amenities by far the best place to stay in Tuscany IT Fantastic staff 5star
Reviewed on Aug 31, 2025
Borgo Scopeto Wine & Country Relais
Save 100% on your flight
Price was $2,517, price is now $1,786 per person
$1,786
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (182 reviews)
This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint
Reviewed on Sep 2, 2025
Where to stay in San Prospero
Find the best San Prospero areas and neighborhoods for the activities you enjoy most. Learn more about San Prospero
Siena City Centre
8 out of top 10 points of interest in this area
Surrounded by photogenic Tuscan hill vineyards and villas, this enchanting medieval center features ancient ramparts, gourmet restaurants and artistic masterpieces.
San Prospero Hotel Deals
Hotel Athena
P Mascagni 55, Siena, SI
$213 nightly
The price is $240 total per night from Sep 4 to Sep 5
$240 total
Sep 4 - Sep 5
Total with taxes and fees
Hotel Ristorante Alcide
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $72 total per night from Sep 7 to Sep 8
$72 total
Sep 7 - Sep 8
Total with taxes and fees
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.
Discover the most popular places to visit in San Prospero
Piazza del Campo
Sit at a café and experience the atmosphere of Siena’s main square, known for its medieval architectural grandeur and famous horse races.
Siena Cathedral
Breathtaking masterpieces by some of the finest Italian artists of the Renaissance era decorate this grandiose 800-year-old religious complex.
Palazzo Pubblico
Palazzo Pubblico is just one of the places to see in Siena, so why not enjoy the other things to explore during your travels? Discover the area's beautiful countryside, or seek out its local tours.
Things to do
Siena & San Gimignano Day Trip from Florence with Chianti Views
$62
per adult
88% of travellers recommend
Siena and San Gimignano: Small-Group Tour with Lunch from Florence
$148
per adult
100% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
$76
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.