Globe trotters exploring central Italy cannot miss a chance to swing by Tuscany. This Italian region boasts breathtaking landscapes, must-visit municipalities, and fine wine. If you’re a big fan of Diane Lane and wish to enjoy your own “Under The Tuscan Sun” moments, you’ll surely have the best time here. You can explore the beautiful town of Cortona, where the American romantic drama was shot, or breeze through more popular destinations, such as Florence and Pisa. From admiring the majestic Duomo in Siena to capturing breathtaking souvenir pictures with Leaning Tower of Pisa, exciting places and must-try activities await visitors. For a truly memorable holiday, stay in accommodation with a swimming pool and make the most of your leisure time. To get an idea of where to stay, browse through this list of the top Airbnbs with pool in Tuscany, Italy.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 30, 2025.
1. Casa Luigi Suite, Tavarnelle Val di Pesa (from USD 1347)
Old meets new in this gorgeous rental, which resonates with traditional Tuscan aesthetics and modern-day accents. From the exposed wooden beams to the fascinating wall art, this accommodation is curated with visually pleasing details. Apart from the design, the amenities are worth appreciating, as well. The fully furnished abode has WiFi, barbecue equipment, and a backyard fitted with a private pool.
The above-ground pool is surrounded by greenery and measures 10 m by 5 m (32.8 ft by 16.4 ft) in width and 1.40 m (4.6 ft) in depth. It is semi-fenced, comes with sun loungers, and offers breathtaking country views.
Barberino Tavarnelle, Firenze, Italy
4.6 km (2.9 mi) from Antinori nel Chianti ClassicoSuperhost
Accommodates: 5
Top guest reviews
Host:
giovanna makes you feel at home and is a great hostgiovanna is a great host that will help you if you have any requestsgiovanna is a great host tries to speak in english as much as possiblegiovanna is such a lovely host and made everything possible to make us feel welcome and at homedefinitely a super hostLocation:
it is perfectly located for a quiet relaxed holiday set in a fabulous location in tuscanya quiet place in the middle of tuscany but still close to many gorgeous places ans citiesi would recommend giovanna's place to anyone but especially cat loversthe pool is a place to spend very relaxing sunny daysthe place is a little paradise with a huge and well taken care of gardenCleanliness:
the place was nice quiet stylish and very cleanRead more reviewsAmenities & Room:
from the view to the private pool to the amazing interiorthe pool and the views from there are simply awesomegreat to have the swimming pool all to yourself (and giovanni conveniently provided large towels)perfect for families great pool we will be back
2. Beautiful treehouse with air-conditioning, Florence (from USD 478)
This Airbnb vacation rental offers tranquility and relaxation. Inspired by laidback treehouses, this elevated rustic retreat blends vintage and modern fittings. It sleeps guests in a cozy queen-size bed and provides them with air-conditioning for added comfort. While the well-furnished, WiFi-ready abode will surely impress you, the outdoor common area will excite you even more.
Vacationers have access to a dreamy shared space with a swimming pool as the main attraction. It nestles in a grassy yard, where your fur baby can roam around while you enjoy a swim. There are loungers surrounding the pool, in case you need a break from swimming.
Florence, Tuscany, Italy
13.39 km (8.4 mi) from Antinori nel Chianti ClassicoAccommodates: 2
Top guest reviews
Host:
great host and great placeshe was very pleasant and helpfulelena was a very gracious host and the place is so romanticthe hosts are friendly and easy to get in touch withelena and her family are wonderful hostsLocation:
the location is most breathtakingly beautifuli definitely recommend this location for a unique getawaythe most beautiful location for a long weekendonly 15 minutes outside of florence it feels a world away so quiet and sereneyou are close enough to florence to get there easily by taxiCleanliness:
treehouse was clean and compacti was impressed how clean the treehouse wasthe place is very clean organized and it has everything you needthank you teresa clean great accommodations super cute and romanticRead more reviewsAmenities & Room:
the air conditioning works but we asked for an additional fan to help circulate the airthere are also a communal pool and tennis court to enjoy as wellthe location is beautiful and the pool amenities were perfect for relaxingwe visited during the europe heatwave so having a pool was a big bonusthe huge garden has many hidden places offering a pool day beds benches chaires etc
3. Fully furnished dwelling close to vineyards, Castellina In Chianti (from USD 351)
How would you like to spend your Tuscan holiday close to a scenic vineyard in Castellina In Chianti? Check out this gorgeous Airbnb with spectacular country scenery and tranquil surroundings, promising vacationers a relaxing stay. The two-bedroom abode is fully furnished, WiFi-ready, and pet-friendly. Plus, guests can enjoy a Pinterest-worthy outdoor pool, surrounded by lush greens and offering landscape views.
The pool is shared among guests and is only seasonally available (from early May to early November). You’ll find sunbeds by the pool, handy whenever you’re in the mood for a poolside reading session.
Castellina in Chianti, Toscana, Italy
19.98 km (12.5 mi) from Antinori nel Chianti ClassicoAccommodates: 4
Top guest reviews
Host:
the hosts are very helpful and accommodating we plan to returnall communications with the hosts were prompt and clearaurelia was kind lovely and a great caretaker of the property as well as hostaurelia is very friendly and instantly made us feel welcomehost were very sweet and even gave us a bottle of wine when we arrived great experienceLocation:
the location is an easy drive from the center of town and also from florencegreat place in a lovely location - just outside castellino in chianti overlooking rolling tuscan hillsa charming apartment in a gorgeous location for an amazing valueit was such a beautiful locationit is close to nearby towns and is a beautiful propertyCleanliness:
very clean and welcomingit is very clean and cozyvery spacious and very cleanthe grounds are beautiful and the space was exceptionally clean and comfortableexcellent stay the apartment was clean and easy to findRead more reviewsAmenities & Room:
our apartment had a great view of the vineyard and tuscan sunsetnewly renovated; complete kitchen with dishwasher ( ); excellent sheets and comforterthe place is amazing the pool area is very nice and the views are amazingthis place was incredible the apartment is very comfortable and has great viewsit is as advertised: a charming apartment on a vineyard in the rolling hills of tuscany
4. Charming hayloft with a hot tub, Greve in Chianti (from USD 142)
Perched atop one of the Chanti Hills, this Airbnb vacation rental offers breathtaking landscape views. Apart from the scenery, the charming stone house delights travelers with a functional kitchen, a cozy queen-size bed, and WiFi. Since it is pet-friendly, your fur baby is welcome to tag along.
From the end of April to the end of October, the salt-filtered outdoor pool, with a solar thermal shower and lighting system, is accessible to vacationers. It measures 11 m by 6 m (36 ft by 19.7 ft) in width and 1.6 m (5.2 ft) in depth. Decorated with sun beds and umbrellas and offering beautiful views, the pool area is a relaxing place to be even when you’re not looking to swim.
Greve in Chianti, Firenze, Italy
16.82 km (10.5 mi) from Antinori nel Chianti ClassicoAccommodates: 2
Top guest reviews
Host:
the host so passionately hospitablegianvani is kind and friendly mangiovanni is an amazing hostgiovanni was an amazing hostgiovanni is the perfect hostLocation:
beautiful location amongst olive trees and grape vineswish we can visit this place again soon in near future thanks giovanni for an amazing staythe location was breathtaking as was chianti's winehad an amazing stay the cabin is located at such a beautiful location surrounded by vineyards all aroundit's a beautiful villa in a great locationCleanliness:
it was clean and comfortableeverything is clean and well equipped for a short visitthe space was comfortable and cleanthe appartment itself was perfectly clean a was better then we expectedRead more reviewsAmenities & Room:
what a place stunning views great hospitality gorgeous grounds and apartmentthe apartment is incredibly comfortable and spacious with a full kitchen patio to eat and a great showerwe has a fireplace in our unit with made it all very romantic and cozythe area is gorgeous and the hayloft is very comfortable and cozywe stayed in the "apartment giovanni" and it was the perfect place for us
Tuscany Tour Guide
Joanna
Hello, my name is Joanna. I was born and raised in Poland but then I fell hopelessly in love with Tuscany and have been living in Florence for 20 years. Wisely enough, I decided to turn my passion into work and became a tour guide. Now I can share with you my immense love for the beauty, history and art of these enchanted places. I am particularly passionate about the Middle Ages, history, scu... Read more
Tours by Joanna
Tuscany Tour Guide
Sara Pallabazzer
I am a lively well-spoken tour guide and tour leader from Florence, and a person who has the ability to motivate different sets of audience; to communicate effectively and possesses a high degree of energy and enthusiasm.I am able to manage multiple tasks, self-motivated team player with excellent communication skills. I am proficient in Italian, English and Norwegian and possess a strong love ... Read more
Tours by Sara
5. Bright abode with an equipped kitchen, Sorana (from USD 318)
If the dreamy town of Sorano is your ideal destination for your Tuscan holiday, you may consider this bright and cozy Airbnb. It is drenched in white, accentuated with beautiful rustic details and modern home decors. An equipped kitchen, a wood burner, and WiFi are some of the many convenient amenities ready for you.
The best part? An outdoor pool, with olive trees for a backdrop, is available for your use. It lights up at night, offering a truly magical experience under the starry skies.
Sorana, Toscana, Italy
54.96 km (34.2 mi) from Antinori nel Chianti ClassicoAccommodates: 4
Top guest reviews
Host:
the hosts were really nice and took care of everythingvery friendly and accommodating hostselisa and her family are wonderful hosts very caring and courteouselisa and her family were very welcoming and kindwe were greeted and treated very friendly and lovely by elisaLocation:
loved the location and privacya perfect getaway locationbeautiful apartment and quiet locationthe location is amazing close to firenze lucca pisa and even the seathe apartment is wonderful furnished and the location is marvelousCleanliness:
sparking clean and thoughtfully designedit was super clean and super cozyit was very quite charming clean and romanticit is impeccably clean stylish and modern while fitting perfectly with the countrysidethe surrounding views are amazing and the house was so clean and well decorated and suppliedRead more reviewsAmenities & Room:
this cozy apartment was by far the best air bnb we have stayed inextremely comfortable bed fully equipped kitchen great showerthe place was very lovely and cozy full of charmeeverything is available in the flat like for cooking and making breakfast the kitchen is fully equippedwe also really enjoyed the fireplace so cozy
6. Characterful stone house with WiFi, Montescudaio (from USD 331)
You can book this traditional Tuscan villa with a bright and sunny interior design for a minimum of two nights. Here, you are free to enjoy great facilities, from an equipped kitchen to WiFi access. On cold days, lounge in the tranquil living area while basking in the warmth from the fireplace.
On a fine summer day, a refreshing soak in the private outdoor pool might just feel perfect. The pool is strategically set outside, inviting patrons to enjoy a swim under the starry skies and surrounded by greenery.
Montescudaio, Toscana, Italy
55.68 km (34.6 mi) from Antinori nel Chianti ClassicoAccommodates: 2
Top guest reviews
Host:
such a lovely place and very nice ownerswe received warm welcome and lot of help from the hostsLocation:
the house is in the middle of a forest perfect place to have a restthe house of giglio is very nice quiet and peacefulRead more reviewsCleanliness:
the house was beautiful clean fully equipped and comfortablegigliola's house was beautifully decorated cozy and very clean
7. Family-friendly country house, La Presura (from USD 484)
Make the most of your visit by staying in this cozy country house, suitable for small groups. An extra single bed can be accommodated for an additional fee. The two-bedroom property nestles in an organic farm, offering peace, quiet, and breathtaking scenery. An equipped kitchen, air-conditioning, and WiFi are also available. Towels and toiletries are provided to guests for added convenience.
Groups with toddlers can request a cot and high chair. Children’s books and toys are also offered here. Holidayers can find an on-site pool, which they can access freely (depending on availability). The seasonal facility is operational from April to October. The pool is unheated and lined by chic white loungers with umbrellas, making it a picture-perfect spot to take your Instagram selfies.
La Presura, Tuscany, Italy
11.5 km (7.2 mi) from Antinori nel Chianti ClassicoAccommodates: 4
Top guest reviews
Host:
the host is welcomingthe staff was wonderfulthe host is always the to helpthe receptionist was extremely sweet and helpful whenever we had questionsour host was fantastic at communicating and offered to help us get a rental carLocation:
ideal location for exploring the rest of tuscany near the auto routefederico's place was the perfect location for usgreat location to a michelin star restaurant and neighboring townswhat an incredible experience the location is perfectly situated between the beautiful countryside as the city of florencela presura is a wonderful location in the countryside outside of florenceCleanliness:
beautiful place big space clean quietthe room was very clean and comfortablethe apartment was fantastic very clean and comfortablethe area was clean and the entire property was very well-maintainedthere is also a nice and clean pool for relaxing in the afternoonRead more reviewsAmenities & Room:
the great advantage was the air conditioningvery nice pool area corresponds with the photoesla presura was a gorgeous property the pool was our favorite part with views of the surrounding valleysthe pool was gorgeous wifi worked great everyone was very friendly and helpfulnice place in the chianti hills with a charming pool and a great view
8. Tuscan-style apartment with barbecue equipment, Gavignano (from USD 109)
Will a swimming pool complete your dream Italian holiday? If so, this cozy Airbnb for two will suit you well. The Tuscan-style apartment grants vacationers access to a beautiful outdoor pool surrounded by rich vegetation. The pool area is semi-fenced and furnished with sunbeds for those lazy afternoon reads. Vineyard views are the property’s best accessory. These vineyards can also be explored by guests.
Additionally, you can expect WiFi, barbecue equipment, and a pet-friendly policy on this property.
Gavignano, Toscana, Italy
14.36 km (9.0 mi) from Antinori nel Chianti ClassicoAccommodates: 2
Top guest reviews
Host:
very friendly hosts make you feeling at home and being part of the familymaritza and elisa were great hosts and vere welcomingelisa is a perfect host who has a lot of attention for her guestsgreat host great family lovely placeyou can't have better hosts than this wonderful familyLocation:
exceptional value and beautiful location couldn't ask for better locationamazing location and great local tipsmagnificent place very beautiful location and viewgreat central location to florence siena and all the great wineries in the areagreat location with short drive to monterigiano san gimignano siena etcCleanliness:
the place was really cleanit was clean comfortable and wonderfully rusticour apartment was very clean and had everything our hearts desiredclean space with many amenitiesthe apartment was clean the yards are well kept and everything was wonderfulRead more reviewsAmenities & Room:
it wasn't a big deal because the view pool garden and patio make this place amazingthe pool was amazing and the views of the tuscan hills were breath takinglovely apartment with a wonderful view over the tuscan hillswe jumped into the big pool and enjoyed the beautiful viewwe felt very comfortable we cooked a tasty dinner and enjoyed the sunset at the pool terrace
9. Casa Vinaria, San Martino In Freddana-monsagr (from USD 1159)
If comfort, tranquility, and privacy are your top priorities for your Tuscan holiday, this accommodation is the perfect home away from home for you. Secluded in an idyllic country location, the fenced Casa Vinaria welcomes four guests as well as fur babies. A kitchen, WiFi, and parking space are all available here.
The cherry on top is the modest-size rectangular outdoor pool set in the beautiful garden, to which you’ll have exclusive access throughout your stay. It measures 4.60 m by 2.60 m (15.1 ft by 8.5 ft), and it is available from April to October. Pool towels are ready for guests, so you can pack light.
San Martino in Freddana, Toscana, Italy
69.05 km (43.0 mi) from Antinori nel Chianti ClassicoAccommodates: 4
Top guest reviews
Host:
good facilities and welcoming hostthe host is very friendly responsive and cooperative (before and during the stay)also a very friendly extra with a welcome basket and croissantscontact with mimicha was very good and friendlyLocation:
what a great place to get away to relaxan ideal relaxing place for two peoplethe area is great and lucca is very closeloved the place and hope to come back again sooni small place ideal for a couple nice kitchen living area bathroom small shower and nice bedroomCleanliness:
swimming pool and the area were very clean and equippedRead more reviewsAmenities & Room:
lovely rustic 'nest' for two in a beautiful setting with exclusive use of a private poolwe had a lovely relaxing week and the pool made the stayfriendly host great view and great terrace with private pool
10. La Pietruzza, Chianni (from USD 433)
All members of the pack will love this self-catering cottage, equipped with two double beds, two single beds, a kitchen, and high-speed internet. If you’re arriving by car, you can securely park on site for free. The accommodation’s highlight is the exclusive outdoor pool, fronting olive and acacia trees on the terrace. The saltwater pool measures 10.5 m by 5 m (33 ft by 16.40 ft) in width and 1.4 m to 2.4 m (4.6 ft to 7.9 ft) in depth. A changing room and an outdoor shower can be found near the pool, so you can clean up before and after a swim. For guests’ convenience, beach towels are ready for use, as well.
For safety purposes, the pool is professionally tested and analyzed. No animals are allowed in the swimming pool.
Chianni, Toscana, Italy
47.37 km (29.5 mi) from Antinori nel Chianti ClassicoAccommodates: 4
Top guest reviews
Host:
your hosts are just perfecti can highly recommend the place and the hostsi highly recommend la pietruzza and getting to know its amazing ownersperhaps the most lovely airbnb we have ever stayed in from designer touches to fantastic hostssuch friendly and helpful peopleLocation:
beautiful property in stunning locationwe had a lovely vacation at this placea little small for 5 people but we are all close so this worked fine for usla pietruzza is a very pleasant place in the heart of toscanadefinitely a place worth exploring especially with nice weatherCleanliness:
the house was very clean and well equippedthe pool was fantastic it's also very deep and very cleannice clean light chalet and enormous garden with pool for your exclusive usagethe pool was beautiful and always cleanit was very clean the kitchen has everything you need and the property is very hugeRead more reviewsAmenities & Room:
the beds linens and other furniture were very comfortablethe view from the pool area is just beautifulthe pool and sound system was great as the general outdoor space was fantasticthe kitchen was well equipped with everything we needed to make wonderful meals including an outdoor grillthe hammocks trampoline bikes table tennis pool grill and home all perfect
Fall in love with Tuscany's dreamy countryside
Tuscany is a gorgeous region with plenty to offer tourists, from iconic cities to tranquil country destinations. For a more memorable visit, be sure to choose the best accommodation for you. You can refer to this list of the best Airbnbs with pools in Tuscany to find where you can stay.
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