Hotels with a Pool in Chianti Region
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Chianti Region Hotels with Pool

Villa I Barronci Resort & Spa
Via Sorripa 10, (GPS: Via Empolese), San Casciano in Val di Pesa, FI
$186 nightly
The price is $211 total per night
$211 total
Sep 21 - Sep 22
Total with taxes and fees
Renovated in 2020, Villa I Barronci Resort & Spa offers a full-service spa, an outdoor pool, and a sauna. There's free parking, and an airport shuttle (available on request) for EUR 80 per vehicle one-way. The front desk has multilingual staff that can help with securing valuables, concierge services, and luggage storage. Other amenities at this luxury hotel include a rooftop terrace, free WiFi in public areas, and a hot tub.
Pool
Hot Tub

Locanda le Piazze
Localita Le Piazze 41, Castellina in Chianti, SI
$344 nightly
The price is $386 total per night
$386 total
Sep 17 - Sep 18
Total with taxes and fees
Guests of Locanda le Piazze have access to a winery, a full-service spa, and an outdoor pool. You can take advantage of free parking, along with an airport shuttle for a fee. The front desk has multilingual staff that can help with securing valuables, tours or tickets, and luggage storage. Other amenities at this adults-only hotel include a gym, free WiFi in public areas, and meeting rooms.
Pool
Breakfast included

Villa la Palagina
Via Grevigiana 4, Figline e Incisa Valdarno, FI
A winery, a rooftop terrace, and free WiFi in public areas are featured at Villa la Palagina. There's free parking and an airport shuttle for a fee. The front desk has multilingual staff that can help with luggage storage, tours or tickets, and dry cleaning/laundry. Other amenities at this family-friendly hotel include a hot tub, a seasonal outdoor pool, and a computer station.
Pool
Hot Tub

Villa Scacciapensieri Boutique Hotel
Strada di Scacciapensieri 10, Siena, SI
Free Cancellation
Reserve now, pay when you stay
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 luggage storage, concierge services, and securing valuables. 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

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA.
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

Borgo Grondaie
Strada delle Grondaie, 15, Siena, SI
Free Cancellation
Guests of Borgo Grondaie enjoy free WiFi in public areas, a seasonal outdoor pool, and free use of bicycles. If you drive, put free parking to good use. Front-desk staff can assist with dry cleaning/laundry, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a library, a terrace, and laundry facilities.
Pool
Pet friendly

Hotel Pescille - Tuscany Charme
Strada Statale 47, Localita Pescille, San Gimignano, SI
$105 nightly
The price is $122 total per night
$122 total
Sep 30 - Oct 1
Total with taxes and fees
Guests of Hotel Pescille - Tuscany Charme enjoy features like a winery, free WiFi in public areas, and a seasonal outdoor pool. A stay here includes free parking. The front desk has multilingual staff that can help with concierge services, luggage storage, and securing valuables. Additional amenities include a terrace, a TV in a common area, and a garden.
Pool
Pet friendly

Villa Ermellina Siena, a Tribute Portfolio Hotel
Via Custoza 2, Siena, SI
Free Cancellation
Reserve now, pay when you stay
$213 nightly
The price is $240 total per night
$240 total
Oct 1 - Oct 2
Total with taxes and fees
At Villa Ermellina Siena, a Tribute Portfolio Hotel, guests enjoy features like a children's pool, a gym, and a rooftop terrace. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for EUR 360 per vehicle roundtrip. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, tours or tickets, 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 family-friendly hotel include free WiFi in public areas, an outdoor tennis court, and meeting rooms.
Pool
Pet friendly

Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13, Gaiole in Chianti, SI
Castello di Spaltenna- Small Luxury Hotels of the World features a full-service spa, an indoor pool, and an outdoor pool. You can put free parking to good use if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, concierge services, and securing valuables. Other amenities at this spa hotel include a gym, a sauna, and free WiFi in public areas.
Pool
Breakfast included

Relais Della Rovere
Via Piemonte 10, Colle di Val d'Elsa, SI
Free Cancellation
Reserve now, pay when you stay
Relais Della Rovere features an outdoor pool, free WiFi in public areas, and conference space. If you drive, put free parking to good use. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this golf hotel include a seasonal outdoor pool, a computer station, and a library.
Pool
Breakfast included

Villa Casagrande Resort & SPA
Via del Puglia, 61, Figline e Incisa Valdarno, FI
Free Cancellation
Reserve now, pay when you stay
$145 nightly
The price is $162 total per night
$162 total
Sep 14 - Sep 15
Total with taxes and fees
Guests of Villa Casagrande Resort & SPA have access to a winery, a full-service spa, and an indoor pool. There's free parking and an area shuttle. Front-desk staff can answer questions 24/7, and assist with concierge services, 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 spa hotel include a gym, free WiFi in public areas, and meeting rooms.
Pool
Spa

Hotel Certaldo
via del Molino, 74, Certaldo, FI
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $218 total per night
$218 total
Sep 21 - Sep 22
Total with taxes and fees
Guests of Hotel Certaldo have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking, and an airport shuttle (available 24 hours) for EUR 120 per person roundtrip. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, and dry cleaning/laundry. Additional amenities include a business center, coffee/tea in a common area, and a meeting room.

Borgo Vescine
Località Vescine, Radda in Chianti, SI
$368 nightly
The price is $414 total per night
$414 total
Sep 14 - Sep 15
Total with taxes and fees
Guests staying at Borgo Vescine enjoy access to a winery, an outdoor pool, and a rooftop terrace. There's free parking, and an airport shuttle (available on request) for EUR 170 per vehicle one-way. The front desk has multilingual staff that can help 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 free WiFi in public areas, a library, and express check-in.

COMO Castello Del Nero
Strada Spicciano 7, Barberino Tavarnelle, FI
$1,201 nightly
The price is $1,330 total per night
$1,330 total
Sep 18 - Sep 19
Total with taxes and fees
Guests staying at COMO Castello Del Nero enjoy access to a full-service spa, a gym, and a sauna. You can take advantage of free parking, along with an airport shuttle for a fee. 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 luxury hotel include outdoor tennis courts, free WiFi in public areas, and a business center.
Pool
Breakfast included

Hotel Colle Etrusco Salivolpi
Via Fiorentina 89, Castellina in Chianti, SI
Hotel Colle Etrusco Salivolpi features an outdoor pool, free WiFi in public areas, and a seasonal outdoor pool. Free parking is available if you drive. The front desk has multilingual staff that can help with dry cleaning/laundry, luggage storage, and concierge services. Other amenities at this hot springs hotel include coffee/tea in a common area, a computer station, and a library.
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.
Chianti Region hotels essential information
Accommodation | 5,146 hotels |
---|---|
Lowest Price | $122 |
Highest Price | $1,330 |
Popular hotels | Villa I Barronci Resort & Spa, Locanda le Piazze, Villa la Palagina, Villa Scacciapensieri Boutique Hotel, VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN SUITE ROOMS, SWIMMING POOL, SPA, SAUNA., Borgo Grondaie, Hotel Pescille - Tuscany Charme, Villa Ermellina Siena, a Tribute Portfolio Hotel, Castello di Spaltenna- Small Luxury Hotels of the World, Relais Della Rovere, Villa Casagrande Resort & SPA, Hotel Certaldo, Borgo Vescine, COMO Castello Del Nero, Hotel Colle Etrusco Salivolpi |