Compare Castelfiorentino Villa Deals

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 Villas in Castelfiorentino

Villa Le Polle di Meletro

Villa Le Polle di Meletro

Via dei Poggi Rivalto Provincia di Pisa
$193 nightly
The price is $212 total per night
$212 total
Sep 29 - Sep 30
Total with taxes and fees
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
Relais Badia a Passignano

Relais Badia a Passignano

Via Martiri di Pratale 12 Barberino Tavarnelle FI
Guests of this villa have access to a seasonal outdoor pool and a garden.
Pool
Kitchen
"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 barbecue grills.
Pool
Kitchen
Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City

Impruneta (Florence) Tuscany
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly villa include barbecue grills and a garden.
Pool
Hot Tub
Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti

Greve in Chianti (Firenze) Toscana
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Transportation is made easy with limo/town car service. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include local meal delivery service, a garden, and barbecue grills.
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
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, a garden, and barbecue grills.
Pool
Hot Tub
Your Perfect Tuscan Retreat for Families and Friends

Your Perfect Tuscan Retreat for Families and Friends

gambassi terme Tuscany
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Other amenities at this family-friendly villa include barbecue grills and a garden.
Pool
Kitchen
TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA

TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA

Buti Tuscany
At this villa, guests have access to a children's pool, a sauna, and a hot tub. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and a garden.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Castelfiorentino
View all properties
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

    Plus Florence - Hostel

    Plus Florence - Hostel

    Via Santa Caterina D'Alessandria, 15 Florence FI
    $127 nightly
    The price is $149 total per night from Oct 25 to Oct 26
    $149 total
    Oct 25 - Oct 26
    Total with taxes and fees
    8.6/10 Excellent! (1,003 reviews)
    The Social Hub Florence Belfiore

    The Social Hub Florence Belfiore

    Viale Belfiore, 55 Florence FI
    $129 nightly
    The price is $158 total per night from Oct 25 to Oct 26
    $158 total
    Oct 25 - Oct 26
    Total with taxes and fees
    9.4/10 Exceptional! (754 reviews)
    The Social Hub Florence Lavagnini

    The Social Hub Florence Lavagnini

    Viale Spartaco Lavagnini 70 72 Florence FI
    $133 nightly
    The price is $162 total per night from Oct 25 to Oct 26
    $162 total
    Oct 25 - Oct 26
    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
1714 Villas
Lowest Price
$149
Highest Price
$212
Popular accommodation
Villa Le Polle di Meletro, Relais Badia a Passignano, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C, Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City, Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti, Montecarlo, 1.5 acres, private pool, walk to restaurants. WIFI Close Lucca, CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5, Your Perfect Tuscan Retreat for Families and Friends, TUSCANY - VILLA - MAX PRIVACY - PISCINA CON VISTA PANORAMICA