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Apartment vacation rentals in Castelfiorentino

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Popular amenities for Castelfiorentino apartment rentals

Weekly apartment rentals

Top guest favorite
The exterior view of a rustic two-story building surrounded by olive trees. A gravel pathway leads to the entrance, and the structure features a blend of stone and plaster with decorative details on the roof. Lush greenery and a clear blue sky provide a serene backdrop.
Apartment in Montaione
4.99 out of 5 average rating, 67 reviews

Col di Pietra – Montaione Country house Belvedere

AndrewRating, 5 stars3 weeks ago
Francesca was an incredible host who supplied us with some great tips on local places to visit and eat at. Her welcome with some snacks and drinks were above and beyond expectation. The accommodation was excellent, and also nice to be able to use the washing machine. Will definitely recommend to friends and family, and would rebook if we return to the area.
Guest favorite
A bright sleeping area features a spacious bed dressed in vibrant red and orange linens. Large windows allow natural light to fill the room, with decorative plants placed nearby. An open wardrobe with wooden hangers and a stylish shelf with ornamental flowers enhance the inviting setting.
Apartment in Castelfiorentino
4.92 out of 5 average rating, 25 reviews

Tuscany Hug Holiday Home

NiekRating, 5 stars1 week ago
Beautiful clean apartment in the heart of Tuscany! Also the communication with the host was fast and very friendly.
Guest favorite
The image captures a view of a historic town square with a Gothic and Romanesque church in the foreground. A rounded window is visible on the church's brick wall. Traditional buildings line the square, while rolling hills and structures adorn the background under a clear blue sky.
Apartment in Castelfiorentino
4.87 out of 5 average rating, 67 reviews

SAN FRANCESCO 1, a two-room with church view

ConnorRating, 5 stars1 week ago
A great place to access Tuscany, 3-minutes walk from the train station with easy access to Florence, Siena, and more. Clean, good value, with great local bakeries and restaurants nearby, and a bottle of wine thrown in too - what more could we ask! On top of that, our host was very responsive and helpful: he called to help to answer questions, and even organised a local taxi for us too. Thanks for a fantastic stay - we’d love to come back!
Guest favorite
Apartment in Castelfiorentino
4.92 out of 5 average rating, 12 reviews

Appartamento "My Tuscan Suite"

IrinaRating, 5 stars2 months ago
Me and my family really enjoyed our stay at Stefania’s apartment. It’s bigger than it seems in the photos, very nice and clean. It has all the facilities, it is a silent area and 5 minutes by walk to the center of the city and railway station. Stefania is a very nice person and it was a pleasure to meet her. I really recommend it, it was the best rent I ever had in Castelfiorentino.
Superhost
An aerial view showcases the agriturismo set among lush vineyards and greenery. The stone buildings with terracotta roofs are surrounded by trees, while the swimming pool is visible near the main structure, providing a refreshing spot in the expansive landscape.
Apartment in San Gimignano
4.66 out of 5 average rating, 159 reviews

comfortable apartment farmhouse SanGimignano

ChristinaRating, 5 stars1 week ago
We had a wonderful time at Poggio! The location is perfect for daytrips and we especially enjoyed the pool which is only to be shared with a few other guests. The view is one of a kind. The apartment is equipped simple, but sufficient as one doesn’t spend too much time there anyways.
Top guest favorite
An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.
Apartment in San Gimignano
4.98 out of 5 average rating, 42 reviews

Herons Superior Apartment - Splendid view!

MicahRating, 5 stars3 weeks ago
Highly recommend anyone new to Italy to try San gimigano first. Staying here allowed us flexibility to explore other cities and had plenty of great spots in walking distance. Lorenzo provided fantastic recommendations and assisted with everything we asked for.
Superhost
The aerial view presents a sprawling landscape containing rows of vineyards and olive trees surrounding a rustic property. In the center, a seasonal swimming pool is nestled within a green garden area, enhancing the serene rural setting.
Apartment in Gambassi Terme
5 out of 5 average rating, 5 reviews

Podere Boscone 3

LiekeRating, 5 stars9 months ago
We really enjoyed it! It was a beautiful location and the location is very central to go to the big well-known cities. The view was breathtaking! You can sit outside. The cottage is a bit more authentic, but that also gives character.
Top guest favorite
A selection of wine glasses is arranged on a tray, accompanied by a bottle of red wine and vibrant flowers. A textured flower vase enhances the setting, reflecting a serene landscape in the background with rolling hills and clear blue skies.
Apartment in Gambassi Terme
4.93 out of 5 average rating, 76 reviews

Bernarduccio's Little House

PedroRating, 5 stars1 week ago
Thanks to Giulia for her responsiveness, the local products left for us and her very clean accommodation with a beautiful view. It is in a great location for visiting the main Tuscan cities.

Private apartment rentals

Guest favorite
A spacious bedroom features a large bed adorned with soft linens. Natural light enters through a window, complemented by warm lamplight. Stone walls and wooden beams add rustic charm. A dresser and side table provide functional decor, and framed images line the walls, enhancing the elegant atmosphere.
Apartment in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars3 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Guest favorite
Three light-colored lounge chairs are positioned beside a swimming pool with clear turquoise water. A towel is draped casually over one chair. Olive trees and greenery surround the pool area, providing a natural and serene backdrop.
Apartment in Castelnuovo Berardenga
4.88 out of 5 average rating, 26 reviews

Colle ai Lecci: Design Apartment in Tuscany

JamesRating, 5 stars2 weeks ago
Beautiful property and a spotless, stylish room. The host was incredibly kind and attentive—made us feel right at home. Would definitely stay again!
Top guest favorite
A spacious living area is presented, featuring a sleek television mounted on a wooden console. A marble coffee table is centered on a soft rug, with a modern armchair positioned nearby. Natural light filters through large windows adorned with light curtains, highlighting the greenery in the corner.
Apartment in Florence
4.96 out of 5 average rating, 74 reviews

Cozy design house with view

AineRating, 5 stars6 days ago
Beautiful place to stay if you’re looking for something further out to enjoy a more scenic stay outside the city! Easy enough to get the bus into the city of Florence for the day also so best of both worlds! The decor and design of the place was beautiful also.
Guest favorite
A private terrace is featured, equipped with a small dining table and chairs. Scenic views of the surrounding historic rooftops and towers are visible, showcasing the charm of the Oltrarno district under a clear blue sky.
Apartment in Centro Storico
4.96 out of 5 average rating, 91 reviews

Panoramic loft with terrace near Ponte Vecchio

SethRating, 5 stars1 week ago
This was the perfect place to stay! Just minutes to the bridge leading to city center along with some fun spots right outside the door. Lots of steps but WORTH IT! The view from the terrace was great and the apartment itself was better than we could’ve asked for! Would definitely recommend this spot to anyone else planning a trip to Florence!
Top guest favorite
A serene outdoor lounge area is framed by lush greenery and features a wooden gazebo with flowing white drapes. Comfortable seating is arranged beneath shaded areas, complemented by a rustic wooden planter with a small tree. Clear blue skies are visible above.
Apartment in Siena
4.97 out of 5 average rating, 32 reviews

Palazzo del Papa Standard Suites

TravisRating, 5 stars1 month ago
AMAZING stay. More beautiful than the photos. Spotless. 5 min drive to Siena. View of the wine country. Bed was more comfortable than my bed at home. Owner was extremely friendly and helpful.
Guest favorite
An inviting living area features rustic wooden beams and terracotta tiles. A round ottoman is centered on a patterned rug, surrounded by a sofa, dining table, and chairs. Large arched windows provide ample natural light, while a decorative chest and artwork accent the walls.
Apartment in San Gimignano
4.96 out of 5 average rating, 24 reviews

Apartment La Roccaia

MelanieRating, 5 stars2 weeks ago
This place is what I imagined when I close my eyes and think of Tuscany. The view from the bedroom is amazing and the apartment is adorable. There is AC but we didn’t end up needing it since the windows let in such a glorious breeze. The kitchen was well equipped, we were just missing paper towels. The pool was great with a fantastic view although it would have been helpful to have access to pool towels. The location is great and about a 15 minute drive into San Gimignano so you probably need a car. It was also a quick drive to supermarkets and nearby wineries which we loved. Berta was really helpful during check-in and provided us with recommendations in the area.
Top guest favorite
An outdoor seating area is illustrated with four black wicker chairs arranged around a small table. Lush greenery surrounds the space, featuring a mix of tall trees and vibrant shrubs. Sunlight filters through the leaves, creating a peaceful ambiance in the garden.
Apartment in Treggiaia
5 out of 5 average rating, 32 reviews

Volpe Sul Poggio - Country Suite

MiriamRating, 5 stars2 weeks ago
We had an amazing stay at Jacopo's place, true paradise! Jacopo is a masterhost and we felt very welcome. The bed is great and we had a bbq in the wonderful garden, very peacefull Tuscan vibes. The cats also roam the garden and are very nice. It is not far from Pisa, about 30 min by car. We recommend this airbnb to everyone! :)
Superhost
A panoramic view captures a sunlit jacuzzi surrounded by lush greenery, with palm trees and verdant hills in the background. A glimpse of distant San Gimignano can be seen, offering a serene and inviting atmosphere for relaxation.
Apartment in Ulignano
4.97 out of 5 average rating, 34 reviews

Breathtaking view of San Gimignano - jacuzzi&pool

SibylleRating, 5 stars3 weeks ago
Very nice accommodation, beautiful complex with large garden/pool and great location for activities nearby by car (including San Gimignano, Florence, Siena) as well as good accessibility to restaurants in the area (e.g. in San Gimignano). The apartment is well furnished and equipped with the essentials for a few days' stay (including kitchen, bathroom). We can recommend the place without further ado. The only point: if you have booked the apartment in the host's house, you must be able to accept the noise of the house (even in the middle of the night).

Apartment rentals with a hot tub

Guest favorite
A view of Palazzo Vecchio is visible through an open window, framed by sheer curtains. The clock tower and architectural details of the building can be seen against a clear blue sky.
Apartment in Centro Storico
4.88 out of 5 average rating, 165 reviews

Love Honeymoon Jacuzzi Piazza Signoria View Ac WiF

MatthewRating, 5 stars2 weeks ago
Our stay at Luca’s place in Florence was wonderful. The location was extremely convenient with main attractions like the uffizi and galleria dell’academia just a short walk away. The apartment is also located in a very nice square that is lively and fun, but not noisy from the room. There are many restaurants and shops just down the stairs. The room itself was all that we could have wanted. The whirlpool tub was a very nice feature, the bed was conformable, and the atmosphere of the room was very cozy. If we return to Florence, we would love to stay at Luca’s place again!
Guest favorite
The luxurious bedroom features a stunning ceiling adorned with a captivating fresco. A spacious bed is placed in the center, accompanied by a state-of-the-art TV nearby. A hydromassage tub situated at the foot of the bed complements the elegant decor, with soft lighting and decorative elements enhancing the ambiance.
Apartment in Centro Storico
4.93 out of 5 average rating, 543 reviews

House of Delights - The Medici private leisure house

XavierRating, 5 stars2 weeks ago
Easy check in and out. Beautiful space and much bigger than expected. Great place to relax and explore if staying in the city. Really no negatives, book it and be happy.
Guest favorite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Apartment in Castelnuovo Berardenga
4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

RachelRating, 5 stars1 week ago
This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.
Top guest favorite
A bright living area features a striped sofa and an elegant glass coffee table on a polished marble floor. Natural light enters through two windows, adorned with light-colored curtains. A small yellow accent chair adds a pop of color to the neutral-toned space.
Apartment in Siena
4.94 out of 5 average rating, 109 reviews

Domus Nannini - L'Angolo di Paradiso Spa (Spa)

DanyelleRating, 5 stars3 weeks ago
After another Airbnb mishap, Gianluca was so accommodating to allow to book and check in late last minute. He even met us there personally to be sure we got in okay. He even had the fold out couch ready with linens and provided a few breakfast items. The place was better than we’d hoped, location was fantastic, updated and perfectly clean! We would absolutely stay here again. This place will be one of the highlights of our trip!
Superhost
A private jacuzzi pool is set in a garden surrounded by greenery. A bottle of champagne and two glasses are placed nearby on a table. Comfortable loungers, with soft cushions, are positioned close to the pool, creating a relaxing outdoor space.
Apartment in Centro Storico
4.8 out of 5 average rating, 274 reviews

Pepi Garden Loft with Jacuzzi Pool

DarrenRating, 5 stars1 month ago
We had a wonderful stay. The patio and hot tub were amazing. Walk to everything. No need for a car. Lots of restaurants and attractions close by. Grocery store around the corner. Outdoor hot tub was lovely after a day of steps.
Guest favorite
An exclusive terrace features a relaxing hot tub surrounded by a spacious seating area with light-colored cushions. Two sleek lounge chairs are positioned nearby, with the checkerboard floor adding a modern touch. Lush greenery complements the serene outdoor space.
Apartment in Lucca
4.86 out of 5 average rating, 201 reviews

The Terrace of Olive Trees in Lucca

KevinRating, 5 stars2 days ago
Emily's apartment is the perfect location to explore Lucca. She was extremely helpful when communicating and very prompt when replying to any queries.
Top guest favorite
The image features a view of the iconic Ponte Vecchio bridge spanning over the Arno River. A small, narrow balcony with a railing is visible, offering a perspective of the historic buildings lining the riverbank under a clear blue sky.
Apartment in Centro Storico
4.98 out of 5 average rating, 268 reviews

[Ponte Vecchio] Prestige and unique view

VieriRating, 5 stars6 days ago
Excellent location and beautiful apartment. Easy to get in self-check in and good communication with the host. Great kitchen, stocked with all the hardware you need. Common area was comfortable for the 4 of us. The view is amazing. Balconies on the water with close up views of Ponte Vecchio. Definitely one of the best places we've stayed in a 20 day trip in several cities.
Top guest favorite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena
4.91 out of 5 average rating, 129 reviews

Villa'Colombaiolo di Marciano', 28

HannahRating, 5 stars3 weeks ago
We loved staying here and had the most fantastic time. They were super helpful and responsive to everything and we can’t wait to go back.

Destinations to explore