Vacation rentals with a pool in Tuscany

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Top-rated rentals with a pool in Tuscany

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 164 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Nov 2 – 9

$507 per night

Guest favorite

Condo in Noce

5.0 out of 5 average rating, 124 reviews

Vergianoni estate nestled in the Chianti with a pool

Podere Vergianoni is located in the beautiful hills of Chianti. The apartment is furnished in perfect traditional style of ancient Tuscany : wooden beams, terracotta floors and unique, handcrafted furniture. Inside you will find a large living room with kitchen ,sofa bed , a bathroom and a bedroom with double bed. In the large outdoor courtyard you will find at your disposal a swimming pool on a breathtaking terrace where you can enjoy a wonderful view of the view with unique sunsets!

Nov 1 – 8

$142 per night

Guest favorite

Apartment in Asciano

4.96 out of 5 average rating, 111 reviews

Loggiato 1 in farm stay with shared pool

Apartment for 2 people IN the Santa Lucia farm stay (farmhouse divided into 7 apartments) IN the Crete Senesi 10 km from Siena. Located on the first floor with a private coffee table in front of the windows of the entrance loggia. It consists of a double bedroom (two single beds joined to form a double bed), bathroom with shower and living room with functional kitchen. Outdoor space with table and chairs on the ground floor. Paid air conditioning in the room according to consumption.

Oct 3 – 10

$82 per night

Guest favorite

Apartment in Caminino

4.92 out of 5 average rating, 127 reviews

Pieve di Caminino Historic Farm

L'antica fattoria Pieve di Caminino, oggi biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due antiche strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Mar 10 – 17

$134 per night

Guest favorite

Farm stay in Lastra a Signa

4.96 out of 5 average rating, 167 reviews

Cozy Room in Tuscany

We have created a cozy and exclusive, that welcomes a maximum of 10 guests, where you can find a feeling of tranquility and freedom. The Micia room of 30 square meters is located on the ground floor and has an independent entrance and can accommodate 2 people. The room has a private bath, microwave, frigobar, express coffee machine and tea kettle. ATTENTION, there is no stove for cooking! Outside, the room's private gazebo overlooking the garden and swimming pool.

Oct 18 – 25

$131 per night

Guest favorite

Castle in Ferrano

4.99 out of 5 average rating, 160 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Mar 14 – 21

$222 per night

Guest favorite

Apartment in Panzano in Chianti (FI)

4.96 out of 5 average rating, 202 reviews

Apt. Panzanello-Panzano in Chianti

The apartment offers all the comforts and tranquility of the Tuscan countryside. Enjoy the wonderful view that you can admire from your private terrace, a perfect place to spend peaceful and serene moments and accompanied by a glass of Panzanello wine. Access to the apartment is private and free parking is available. Kitchen is equipped with everything you need to prepare delicious meals. We do not have a restaurant but we will help you book in Panzano.

Nov 7 – 14

$130 per night

Guest favorite

Apartment in La Presura

4.91 out of 5 average rating, 108 reviews

Country house 9 km to Florence-2+1g,free parking

We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

Dec 2 – 9

$102 per night

Guest favorite

Home in Anghiari

4.99 out of 5 average rating, 194 reviews

Casa Rosmarino Eco-Wellness Country Home

Price Includes: - WELLNESS HOT TUB w/Jacuzzi Infrared SAUNA - FOOD & DRINKS 1 Welcome Aperitivo 1 Wine 1 Nespresso w/Capsules - COMFORT Heater 2 Night Included, Extra Night 25 Euro Shower Gel / Shampoo / Hair Dryers Bathrobes / Flips Flops Wood for the HotTub and Fireplace - EXTRA (not included) MASSAGES PASTA Making Class, Oil/Truffle/Wine TASTING Please INQUIRE for price & availability

Dec 30 – Jan 6

$416 per night

Guest favorite

Farm stay in Castelnuovo dei Sabbioni

4.92 out of 5 average rating, 300 reviews

Chianti La Pruneta, Raffaello Apartment

Stunning apartment in the heart of Tuscany set in the middle of vines and olives trees. The apartment has been totally refurbished keeping the lovely old features, beamed ceilings, marble floors with antique furniture. Patio doors lead to a private terrace with sun loungers for relaxing and space. With table and chairs you can eat 'Al fresco' enjoying the beautiful views.

Nov 24 – Dec 1

$91 per night

Guest favorite

Tower in Fiesole

4.95 out of 5 average rating, 153 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Aug 23 – 30

$784 per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 303 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence. Hayloft completely independent on two floors connected by an internal staircase. Private garden of 300 mq sorrounded by secolar oaks.

Nov 7 – 14

$170 per night