Photo by Vanessa Sgaravizzi

Search Castelfiorentino Cottages

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Cottages in Castelfiorentino

BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Outdoor pool

BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany

9.8 out of 10, Exceptional, (67)
"This is a great property with loveku views and a great welcome. Loved our stay and will be going back."
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Typical Tuscan Countryside Cottage near Florence
Property grounds

Typical Tuscan Countryside Cottage near Florence

10.0 out of 10, Exceptional, (28)
"Had a great stay with another couple staying upstairs and my wife and and in the downstairs. Host was amazing and her dog, Gustavino, checked in on us each morning! I wish there had been a vineyard with tasting room within walking distance but there were many within 15 minutes by car. Host set us up with restaurant options and they were all excellent. "
Typical Tuscan Countryside Cottage near Florence
Santo Pietro Resort
Front of property

Santo Pietro Resort

10.0 out of 10, Exceptional, (1)
"Un excellent service à la clientèle. Un gros merci à Chiara pour son accueil et sa rapidité de régler une petite problématique "
Santo Pietro Resort
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Exterior

FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

9.4 out of 10, Exceptional, (18)
"We stayed in apartment Falco which has great views over the valley.The apartment is exactly as listed,well equipped and spotlessly clean.It is perfectly placed for visiting all the top Tuscan towns and there are numerous local restaurants within easy reach. Fabio and Annemarie are wonderful hosts and we will definitely be visiting again. Thanks for a wonderful stay."
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Outdoor pool

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle

9.6 out of 10, Exceptional, (20)
"More than we imagined for our Tuscany vacation. Spacious, well appointed and clean. Marzio was an excellent host with knowledge of the area and its history. He gave wonderful suggestions for wines, restaurants and touring excursions. We highly recommend this historical villa for a Tuscany vacation!"
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
TUSCAN COTTAGE WITH PRIVATE GARDEN AND PANORAMIC POOL. 1 KM WALK TO THE VILLAGE.
Outdoor pool

TUSCAN COTTAGE WITH PRIVATE GARDEN AND PANORAMIC POOL. 1 KM WALK TO THE VILLAGE.

9.8 out of 10, Exceptional, (31)
"This beautiful holiday house iis located at a beautiful county side in Casole d'elsa and is closeby to Florence, Chianti, Siena and Umbria. It is also easily accessible and you can take a train to Florence in less than an hour. Owner is friendly and you will feel like home once you walk in. They are also helpful in giving advise on interesting places to visit and even planning for your trip if you need it."
TUSCAN COTTAGE WITH PRIVATE GARDEN AND PANORAMIC POOL. 1 KM WALK TO THE VILLAGE.
COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN
Outdoor pool, sun loungers

COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN

9.8 out of 10, Exceptional, (40)
"Everything was very satisfactory"
COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN
Cottage 'Vinombrosa' with Private Pool, Wi-Fi and Air Conditioning
TV, fireplace

Cottage 'Vinombrosa' with Private Pool, Wi-Fi and Air Conditioning

10.0 out of 10, Exceptional, (1)
Cottage 'Vinombrosa' with Private Pool, Wi-Fi and Air Conditioning
Happy holidays in Chianti, among olives and vineyards, From Florence
Pool

Happy holidays in Chianti, among olives and vineyards, From Florence

9.6 out of 10, Exceptional, (18)
"A lovely little cottage in beautiful surroundings and perfectly situated to discover Tuscany. Elisabeth is lovely and very friendly and helpful and Oliver is brilliant"
Happy holidays in Chianti, among olives and vineyards, From Florence
Charming Farmhouse with Private Pool among Vineyards
Outdoor pool, a heated pool

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (50)
"We stayed here with our family as a large group of 8 adults and 1 infant. The layout of the house worked great, each couple had their own room (even our daughter) and their own bathroom! Our daughter loved the pool and the property had everything we needed. The location was great, our group took day trips to explore Siena, Florence, and wine country. The winery on the property was also fantastic! A great place to say and I highly recommend it!"
Charming Farmhouse with Private Pool among Vineyards
Independent Cottege in Tuscany
Pool

Independent Cottege in Tuscany

9.0 out of 10, Wonderful, (2)
Independent Cottege in Tuscany
Panorama Nest - Countryside charm with private pool
Outdoor dining

Panorama Nest - Countryside charm with private pool

9.0 out of 10, Wonderful, (4)
"A very quiet und beautiful Place for These looking for siilence and nature.Small House, but clean and excellent equipped.A wonderful terrace with breathtaking view."
Panorama Nest - Countryside charm with private pool
Old cottage in the heart of Tuscany, quiet, near Lucca, Florence, Pisa, Siena
Terrace/patio

Old cottage in the heart of Tuscany, quiet, near Lucca, Florence, Pisa, Siena

9.6 out of 10, Exceptional, (43)
"My husband surprised me with a trip to Tuscany to celebrate a "big" birthday. We had been watching movies and travel shows on TV for a while and knew that we wanted to walk the wall in Lucca for sure. We looked at many accommodations in the area, and decided that our key decision factors would be: (1) a place that looks and feel like Tuscany, where we could relax with a glass of wine at the end of the day, (2) proximity to restaurants, (3) conveniently located to travel the area. This house was...
Old cottage in the heart of Tuscany, quiet, near Lucca, Florence, Pisa, Siena
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Terrace/patio

Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani

10.0 out of 10, Exceptional, (4)
"A slice of Tuscany heaven. Endless views with a pool too! Il Casetto is a loved home and it shows everywhere you look. From lovely decorated rooms to beautiful gardens and a great "cucina" Il Casetto was perfect for our family. The location is just minutes from Castellina in Chianti which is a great home base for touring Tuscany. The VRBO photos are excellent at capturing the home. Every day our family would enjoy sunrise with the aroma of the flowering plants. Jasmin, oleander and others...
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Outdoor pool

Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.

9.0 out of 10, Wonderful, (20)
"A great stay in a beautiful part of the world. We go some great recommendations from the host on places to eat and we weren’t disappointed. Just an amazing stay!"
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano
Outdoor pool

Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano

7.0 out of 10, Good, (4)
"Loved this quaint cottage. We will be back."
Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Outdoor pool

Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities

9.8 out of 10, Exceptional, (31)
"This is a great location to experience the beauty of Tuscany. People interested in history find this place even more interesting and mystical. Check out the history on their website. Owners did an incredible job restoring the beauty of this place. The entire family lives on site , so it so convenient to seek their advise. They are very helpful and knowledgeable and for us it felt like we were with family. I would definitely recommend this place to my friends and family members. We loved our 5...
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Rustikale Villa mit Privat Pool in Buti, Toscana. Haustierfreundlich
Fridge, microwave, oven, stovetop

Rustikale Villa mit Privat Pool in Buti, Toscana. Haustierfreundlich

Rustikale Villa mit Privat Pool in Buti, Toscana. Haustierfreundlich
Charming Vineyard Escape
Cottage | View from property

Charming Vineyard Escape

Charming Vineyard Escape
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Pool

Exceptionally pretty cottage with pool, views, in walking distance from Panzano

10.0 out of 10, Exceptional, (43)
"Superb location / great scenery Lucrezia is a welcoming hostess "
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castelfiorentino Hotel Reviews

Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

10/10 Excellent
"The hotel was very nice and perfectly located"
Menachem 3-night trip
Posted 11 hours ago
Plaza Hotel Lucchesi