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Holiday rentals with a pool in Guardistallo

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Guardistallo

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

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Home in Florence

4.89 out of 5 average rating, 721 reviews

TREEhouse/casaBARTHEL

casaBARTHEL is a perfect place for a vacation and an artist residency, immersed in the Tuscan landscape only 15' from the Duomo and 30' from Siena. Come and live with us; enjoy our olive trees, the kitchen garden and our family life style away from the working rhythm. By providing wifi only in the communal courtyard we suggest our guests to utilize internet only when is really needed. Taking a break from been connected with elsewhere and enjoy the 'here and now' could be our best present to you!

23 – 30 Oct

$3,442 AUD total

Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 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

13 – 20 Apr

$6,826 AUD total

Guest favourite

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!

30 Mar – 6 Apr

$1,862 AUD total

Guest favourite

Apartment in Caminino

4.92 out of 5 average rating, 129 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.

14 – 21 Mar

$1,723 AUD total

Guest favourite

Farm stay in Lastra a Signa

4.96 out of 5 average rating, 168 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.

18 – 25 Oct

$1,544 AUD total

Guest favourite

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 views that you can admire from your private terrace, the perfect place to spend moments of peace and serenity accompanied by a glass of Panzanello wine. Access to the apartment is private and free parking is available. The kitchen is equipped with everything you need to prepare delicious meals. We don't have a restaurant but we'll help you book in Panzano.

7 – 14 Nov

$1,397 AUD total

Guest favourite

Cottage in Chianni

4.98 out of 5 average rating, 118 reviews

La Pietruzza - The Private Chalet with a Soul -

Detached country cottage (in exclusive use) in stone and glass dating from XVIII century ideal for 4 persons. Wide wooden veranda. EXCLUSIVE POOL with SALTED WATER ( 33 ft x 16.40 ft ) depth of the pool from 4.6 ft to 7.9 ft. The Chalet is surrounded by 6000 meters of land with fruit trees, olive trees, acacias. We care about nature and do not use herbicides. There is no gas at home because it is all electric with photovoltaic system. (CIR O5OO12LTNOOO3)

7 – 14 Apr

$2,764 AUD total

Guest favourite

Cottage in Lucardo

4.99 out of 5 average rating, 216 reviews

Best view ever & private pool

Antique Tuscan barn made into a comfortable home with private swimming pool. Best views ever. Close to Florence, Siena and Pisa. Very quiet, yet easy to reach. Sunsets you can only dream of. Ideal Tuscan getaway for family or two couples. The house has two bedrooms and two bathrooms plus a guest bathroom on the ground floor. The pool has a panoramic edge and whirlpool section. There are two restaurants on walking distance (a few hundred meters).

14 – 21 Mar

$2,877 AUD total

Farm stay in Monterotondo Marittimo

4.83 out of 5 average rating, 166 reviews

Studio apt. in Estate with Craft Brewery

Our organic farm is surrounded by 400 hectares of fields and woods, which gently slope down towards the quiet Val di Cornia. The ancient farmhouses and terrain represent the traditional Maremma Toscana. Here, we offer an unforgettable experience of culture, nature, food, adventure and relaxation. The estate features or farm-to-table restaurant, two panoramic swimming pools, farm animals, signed paths and agricultural craft brewery.

25 Oct – 1 Nov

Guest favourite

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.

23 – 30 Sept

$9,029 AUD total

Guest favourite

Home in Certaldo

4.91 out of 5 average rating, 109 reviews

Paluffo Stillo House

Paluffo is an historic 15th century building restored in 2010 conserving its original structure and design. Stillo house features a spacious living room with dining room and a fireplace, 2 bedrooms and 1 of them has a loft with a single bed, 2 bathrooms, a big kitchen, and a private garden with a wonderful view of the Chianti hills.

18 – 25 Oct

$3,608 AUD total

Guest favourite

Farm stay in Pisa

4.99 out of 5 average rating, 249 reviews

Estate Closing it in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer.

24 – 31 Mar

$3,427 AUD total

Holiday rentals for every style

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Popular amenities for Guardistallo rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Volterra

4.92 out of 5 average rating, 159 reviews

Podere Collina

14 – 21 Dec

$3,363 AUD total

Home in San Miniato

4.91 out of 5 average rating, 102 reviews

Private villa/swimming pool in Tuscany

26 Oct – 2 Nov

$2,756 AUD total

Guest favourite

Home in Localita' Pievescola

4.93 out of 5 average rating, 147 reviews

Antico Borgo Ripostena – no. 8 Casa Vecchia

15 – 22 Apr

$2,277 AUD total

Home in Lucca

4.84 out of 5 average rating, 149 reviews

SunnySide, house with pool on Lucca hills

5 – 12 Dec

$1,426 AUD total

Guest favourite

Home in Barberino Val D'elsa

4.97 out of 5 average rating, 103 reviews

Podere Villetta La Colombaia

11 – 18 Jan

$1,521 AUD total

Guest favourite

Home in Castelfiorentino

4.9 out of 5 average rating, 139 reviews

App.with pool and beautiful view, 5+2

29 Mar – 5 Apr

$1,491 AUD total

Guest favourite

Home in Bagno a Ripoli

4.94 out of 5 average rating, 101 reviews

Casetta Melograno - Cozy farmhouse in Chianti

7 – 14 Oct

$1,185 AUD total

Guest favourite

Home in Montescudaio

4.96 out of 5 average rating, 91 reviews

Open space immersed in nature

7 – 14 Dec

$1,700 AUD total

Condo rentals with a pool

Guest favourite

Condo in San Gimignano

4.95 out of 5 average rating, 110 reviews

Adalberto Apartment inside the Manor of Fulignano

9 – 16 Oct

$1,301 AUD total

Guest favourite

Condo in Morrona

4.96 out of 5 average rating, 112 reviews

Casa Luna-Splendida overlooking the pool and Tuscan nature

16 – 23 Oct

$1,364 AUD total

Guest favourite

Condo in Strada in Chianti

4.94 out of 5 average rating, 324 reviews

Chianti Apartment in 12th Century Tuscan farmhouse

26 Feb – 5 Mar

$1,149 AUD total

Guest favourite

Condo in Casole d'Elsa

4.93 out of 5 average rating, 124 reviews

La Casetta

15 – 22 Dec

$1,675 AUD total

Condo in Fiesole

4.88 out of 5 average rating, 154 reviews

Poggiolieto Studio - on hills 10' from city center

17 – 24 Feb

$1,350 AUD total

Guest favourite

Condo in Florence

4.93 out of 5 average rating, 137 reviews

VILLA LE PERGOLE - Florence

3 – 10 July

$3,080 AUD total

Guest favourite

Condo in Guardistallo

4.82 out of 5 average rating, 17 reviews

Two-room apartment with swimming pools and garden

11 – 18 June

$1,401 AUD total

Guest favourite

Condo in Montecatini Val di Cecina

4.94 out of 5 average rating, 17 reviews

Agriturismo Santa Chiara Apartment with pool

7 – 14 Dec

$1,700 AUD total

Home rentals with a private pool

Guest favourite

Cottage in San Filippo A Ponzano

4.98 out of 5 average rating, 171 reviews

Stone House with Exclusive Pool Codilungo in Chianti

17 – 24 Jan

$4,084 AUD total

Guest favourite

Villa in San Ginese di Compito

4.99 out of 5 average rating, 112 reviews

Farmhouse , pool, 13 px. Lucca 10km

14 – 21 Feb

$7,649 AUD total

Guest favourite

Home in San Casciano in Val di pesa

4.82 out of 5 average rating, 73 reviews

Tuscan Villa Featured Conde Nast Best Villas Italy

23 – 30 Nov

$7,406 AUD total

Guest favourite

Home in Tavarnelle Val di Pesa

4.92 out of 5 average rating, 73 reviews

Casa Luigi Suite with Exclusive Pool

11 – 18 Sept

$2,620 AUD total

Guest favourite

Villa in San Miniato

4.86 out of 5 average rating, 37 reviews

Villa with exclusive pool

20 – 27 Apr

$3,814 AUD total

Home in Vecchiano

4.67 out of 5 average rating, 3 reviews

Belvedere by Interhome

20 – 27 Sept

$2,174 AUD total

Villa in Crespina

Bellavista

19 – 26 Nov

$8,594 AUD total

Villa in Casino di Terra

4.81 out of 5 average rating, 62 reviews

Private Retreat in Tuscan Countryside

9 – 16 Sept

$4,583 AUD total

Quick stats about holiday rentals with a pool in Guardistallo

Total rentals
110 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
610 reviews
Nightly prices starting at
$61 AUD before taxes and fees

Destinations to explore