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Featured Villas in Castelfiorentino

Villa Le Polle di Meletro

Villa Le Polle di Meletro

Via dei Poggi Rivalto Provincia di Pisa
Villa Le Polle di Meletro features a sauna, free WiFi in public areas, and a hot tub. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with luggage storage, and answer any questions about the accommodations. Additional amenities include a terrace, laundry facilities, and a garden.
Hot Tub
Pet friendly
Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena

Fonterutoli Provincia di Siena
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This villa also has a garden.
Pool
Hot Tub
Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca

Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca

Montecarlo
Guests staying at this villa enjoy an outdoor pool, a terrace, and laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Monteriggioni SIENA Toscana
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. Transportation is made easy with limo/town car service. This family-friendly villa also has a garden.
Pool
Kitchen
EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE

EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE

IMPRUNETA Tuscany
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Villa Bartolini Baldelli - Authentic XV century villa with garden and pool

Toscana Città Metropolitana di Firenze
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Luxury Villa in Tuscany with Pool near Pisa and Florence - Ten Bedrooms 20 pl

Luxury Villa in Tuscany with Pool near Pisa and Florence - Ten Bedrooms 20 pl

Palaia Toscana
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Other amenities at this family-friendly villa include a garden and barbecue grills.
Pool
Hot Tub
CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5

Strada In Chianti Città Metropolitana di Firenze
Guests of this villa have access to an outdoor pool, a gym, and a hot tub. Transportation is made easy with limo/town car service. Additional amenities include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

San Casciano in Val di Pesa Tuscany
Guests of this villa enjoy features like an outdoor pool, a gym, and a terrace. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and a garden.
Pool
Kitchen
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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.

Hotel Options in Castelfiorentino

    The Social Hub Florence Lavagnini

    The Social Hub Florence Lavagnini

    Viale Spartaco Lavagnini 70 72 Florence FI
    $90 nightly
    The price is $116 total per night from Aug 30 to Aug 31
    $116 total
    Aug 30 - Aug 31
    Total with taxes and fees
    9/10 Wonderful! (1,505 reviews)
    Plus Florence - Hostel

    Plus Florence - Hostel

    Via Santa Caterina D'Alessandria, 15 Florence FI
    $81 nightly
    The price is $98 total per night from Aug 19 to Aug 20
    $98 total
    Aug 19 - Aug 20
    Total with taxes and fees
    8.6/10 Excellent! (1,010 reviews)
    Hotel Paris

    Hotel Paris

    Via Banchi 2 Florence FI
    $139 nightly
    The price is $167 total per night from Aug 14 to Aug 15
    $167 total
    Aug 14 - Aug 15
    Total with taxes and fees

Luxury Villas

Book luxury villas in Castelfiorentino
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Castelfiorentino. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Castelfiorentino, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Castelfiorentino
You won’t have a problem finding your own space in Castelfiorentino. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Castelfiorentino on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Castelfiorentino rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Castelfiorentino Villas essential information

Accommodation
1713 Villas
Lowest Price
$98
Highest Price
$167
Popular accommodation
Villa Le Polle di Meletro, Private villa in the heart of chianti with view of siena, Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca, Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence. , EXCLUSIVE CHIANTI VILLA SPECTACULAR POOL TENNIS COURT 15 MIN TOFLORENCE , Villa Bartolini Baldelli - Authentic XV century villa with garden and pool, Luxury Villa in Tuscany with Pool near Pisa and Florence - Ten Bedrooms 20 pl, CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C