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Featured Province of Siena Romantic Getaways & Hotels

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
At this villa, guests enjoy features like an outdoor pool, a gym, and a sauna. Transportation is made easy with limo/town car service. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub

Palazzo Leopoldo Dimora Storica & Spa
Via Roma 33 Radda in Chianti SI
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $112 total per night
$112 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa features a full-service spa, an indoor pool, and an outdoor pool. There's free parking, and an airport shuttle (available 24 hours) for EUR 150 per room one-way. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, tours or tickets, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include a gym, a sauna, and a rooftop terrace.
Pool
Hot Tub

Castello di Fonterutoli Wine Resort
Via Puccini 4 Castellina in Chianti SI
Free Cancellation
Reserve now, pay when you stay
$196 nightly
The price is $220 total per night
$220 total
Dec 22 - Dec 23
Total with taxes and fees
Guests of Castello di Fonterutoli Wine Resort enjoy features like a winery, free WiFi in public areas, and refrigerator in a common area. You can take advantage of free offsite parking, along with limo/town car service. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Additional amenities include a meeting room, a library, and wedding services.
Pet friendly
Free WiFi

Hotel Le Fontanelle
SP 408-km 14.7 Castelnuovo Berardenga SI
A local mainstay since 1200, Hotel Le Fontanelle offers a winery, a full-service spa, and an indoor pool. Free valet and self parking are available, and there's also limo/town car service. The 24-hour front desk has multilingual staff ready to assist with securing valuables, dry cleaning/laundry, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a gym, a sauna, and free WiFi in public areas.
Pool
Hot Tub

ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km
Siena, Toscana Italy
Guests of this villa have access to an outdoor pool, a gym, and free WiFi in public areas. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub

Castello di Casole, A Belmond Hotel, Tuscany
Localita Querceto Casole d'Elsa SI
Guests of Castello di Casole, A Belmond Hotel, Tuscany enjoy a full-service spa, an outdoor pool, and a gym. Free valet and self parking are available, and there's also an airport shuttle for a fee. The 24-hour front desk has staff standing by to help with securing valuables, concierge services, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include in-room fitness, a steam room, and free WiFi in public areas.
Pool
Hot Tub

Castello di Leonina Relais
Strada Di Leonina 5 Asciano SI
Free Cancellation
Reserve now, pay when you stay
$162 nightly
The price is $185 total per night
$185 total
Dec 29 - Dec 30
Total with taxes and fees
Guests staying at Castello di Leonina Relais enjoy an outdoor pool, a sauna, and free WiFi in public areas. If you drive, put free parking to good use. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include a hot tub, express check-in, and express check-out.
Pool
Hot Tub

Cdh Hotel Radda
Loc La Calvana, 138 Radda in Chianti Tuscany
At Cdh Hotel Radda, guests enjoy a full-service spa, an outdoor pool, and a children's pool. Onsite parking is offered for a fee. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this spa hotel include a gym, a sauna, and a rooftop terrace.
Pool
Hot Tub

Relais Vignale & Spa
Via Pianigiani 9 Radda in Chianti SI
A full-service spa, a sauna, and a rooftop terrace are featured at Relais Vignale & Spa. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for EUR 135 per vehicle one-way. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, luggage storage, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this spa hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub

Hotel Palazzo San Lorenzo & SPA
Via Gracco Del Secco 113 Colle di Val d'Elsa SI
Free Cancellation
Reserve now, pay when you stay
A full-service spa, a sauna, and free WiFi in public areas are featured at Hotel Palazzo San Lorenzo & SPA. A stay here includes free offsite parking. The front desk is staffed 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a hot tub, meeting rooms, and free newspapers.
Hot Tub
Breakfast included

Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Free Cancellation
Reserve now, pay when you stay
Castello di Velona Resort Thermal SPA & Winery features a winery, a full-service spa, and 2 outdoor pools. Free valet and self parking are available, and there's also an area shuttle. Multilingual staff at the 24-hour front desk can assist with securing valuables, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include an indoor pool, a gym, and 4 hot tubs.
Pool
Hot Tub

Villa San Lucchese
Località San Lucchese, 5 Poggibonsi SI
Free Cancellation
Reserve now, pay when you stay
Villa San Lucchese offers a children's pool, free WiFi in public areas, and an outdoor tennis court. There's free parking, and an airport shuttle (available 24 hours) for EUR 140 per vehicle. The 24-hour front desk has multilingual staff ready to assist with securing valuables, concierge services, and dry cleaning/laundry. Other amenities at this family-friendly hotel include a seasonal outdoor pool, a library, and express check-out.
Pool
Breakfast included

Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection
Via Poliziano 18 San Quirico d'Orcia SI
Free Cancellation
Reserve now, pay when you stay
$173 nightly
The price is $197 total per night
$197 total
Dec 19 - Dec 20
Total with taxes and fees
A full-service spa, a sauna, and free WiFi in public areas are featured at Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection. There's onsite parking for a fee, and an airport shuttle (available 24 hours) for EUR 220 per room one-way. The front desk has multilingual staff that can help with securing valuables, concierge services, and dry cleaning/laundry. Other amenities at this luxury hotel include meeting rooms, a conference center, and a business center.
Pool
Breakfast included

Villa Scacciapensieri Boutique Hotel
Strada di Scacciapensieri 10 Siena SI
Guests of Villa Scacciapensieri Boutique Hotel enjoy a rooftop terrace, free WiFi in public areas, and a seasonal outdoor pool. Free offsite parking is included with your stay. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, pet-sitting services, and litter boxes. Other amenities at this family-friendly hotel include coffee/tea in a common area, a computer station, and a library.
Pool
Breakfast included

Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Free Cancellation
Reserve now, pay when you stay
$299 nightly
The price is $336 total per night
$336 total
Dec 21 - Dec 22
Total with taxes and fees
Guests of Grand Hotel Continental Siena – Starhotels Collezione enjoy access to free WiFi in public areas, conference space, and a 24-hour business center. Valet parking is EUR 55 per day if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for EUR 252 per vehicle one-way. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a computer station, a library, and laundry facilities.
Pet friendly
Free WiFi
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View all propertiesLowest 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.
Province of Siena Romantic Getaways & Hotels essential information
Romantic Getaways & Hotels in Province of Siena |
415 |
|---|---|
Highest price | $336 |
Cheapest price | $112 |
Total number of hotels in Province of Siena | 5,950 |
Popular hotels | VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA., Palazzo Leopoldo Dimora Storica & Spa, Castello di Fonterutoli Wine Resort, Hotel Le Fontanelle, ALL PROPERTY 7BR- Charming Tuscan Villa with pool, hot tub, A/C,Siena 15 km, Castello di Casole, A Belmond Hotel, Tuscany, Castello di Leonina Relais, Cdh Hotel Radda, Relais Vignale & Spa, Hotel Palazzo San Lorenzo & SPA, Castello di Velona Resort Thermal SPA & Winery, Villa San Lucchese, Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection, Villa Scacciapensieri Boutique Hotel, Grand Hotel Continental Siena – Starhotels Collezione |
Recent Reviews

Hotel Athena
5/5 Excellent
"Great location, very friendly staff"
A verified traveler stayed at Hotel Athena
Posted 5 days ago
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