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Vacation rentals with a pool in Siena

Find and book unique homes with a pool on Airbnb

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Top-rated rentals with a pool in Siena

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

Guest favorite
Villa in Castellina in Chianti
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
Oct 24 – 31
$516 per night
4.93 out of 5 average rating, 164 reviews
Guest favorite
Apartment in Asciano
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
$84 per night
4.96 out of 5 average rating, 111 reviews
Guest favorite
Villa in Siena
Fascinating Villa Senese with View!
Old restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time flows slowly according to ancient traditions. One of the most beautiful views that the Tuscan view can give, exclusive pool, large triple garden, BBQ, BBQ, poolside table, terrace to enjoy the sunset on the medieval towers on the horizon while sipping the organic wines of the estate, original and working fireplace, free parking, WI-FI internet, WI-FI.
Dec 5 – 12
$705 per night
4.9 out of 5 average rating, 252 reviews

Popular amenities for Siena rentals with a pool

House rentals with a pool

Superhost
Home in Florence
TREEhouse/casaBARTHEL
Aug 5 – 12
$268 per night
4.89 out of 5 average rating, 710 reviews
Guest favorite
Home in Certaldo
Paluffo Stillo House
May 6 – 13
$433 per night
4.9 out of 5 average rating, 105 reviews
Guest favorite
Home in Casale
Infinity view
Jan 8 – 15
$434 per night
4.86 out of 5 average rating, 153 reviews
Guest favorite
Home in Anghiari
Casa Rosmarino Eco-Wellness Country Home
Nov 26 – Dec 3
$399 per night
4.99 out of 5 average rating, 187 reviews
Guest favorite
Home in Prato
Tofanello Orange Luxury and Modern Comfort with Outdoor Pool
Nov 25 – Dec 2
$188 per night
4.98 out of 5 average rating, 109 reviews
Guest favorite
Home in Localita' Pievescola
Antico Borgo Ripostena – no. 8 Casa Vecchia
Oct 6 – 13
$185 per night
4.93 out of 5 average rating, 143 reviews
Guest favorite
Home in Lecchi in Chianti
Casa di Lyndall - Entire house with exclusive pool
Mar 8 – 15
$141 per night
4.98 out of 5 average rating, 111 reviews
Superhost
Home in Anghiari
Tuscan dream in the ancient Tobacco's villa, sauna
Nov 22 – 29
$238 per night
4.88 out of 5 average rating, 121 reviews
Guest favorite
Home in Foiano della Chiana
Conca d'Oro house sleeps 4
Jan 21 – 28
$271 per night
4.92 out of 5 average rating, 110 reviews
Guest favorite
Home in Terranuova Bracciolini
Villa Lolù with private heated swimming-pool
Aug 21 – 28
$692 per night
4.96 out of 5 average rating, 103 reviews
Guest favorite
Home in Poggibonsi
Fairy House with Pool, Chianti Area
Aug 20 – 27
$278 per night
4.94 out of 5 average rating, 116 reviews
Guest favorite
Home in Sorana
Tuscan Nature Views From Casa Gave
Mar 17 – 24
$80 per night
4.96 out of 5 average rating, 238 reviews

Condo rentals with a pool

Guest favorite
Condo in Noce
Vergianoni estate nestled in the Chianti with a pool
Feb 12 – 19
$106 per night
5.0 out of 5 average rating, 109 reviews
Guest favorite
Condo in arezzo
Explore Nature in Downtown Chianti Vigneti
Oct 25 – Nov 1
$231 per night
4.97 out of 5 average rating, 197 reviews
Guest favorite
Condo in Casole d'Elsa
La Casetta
Jan 11 – 18
$127 per night
4.93 out of 5 average rating, 121 reviews
Guest favorite
Condo in San Gimignano
Adalberto Apartment inside the Manor of Fulignano
Oct 11 – 18
$99 per night
4.94 out of 5 average rating, 109 reviews
Guest favorite
Condo in Strada in Chianti
Chianti Apartment in 12th Century Tuscan farmhouse
Oct 7 – 14
$92 per night
4.94 out of 5 average rating, 315 reviews
Guest favorite
Condo in Florence
VILLA LE PERGOLE - Florence
Aug 15 – 22
$244 per night
4.93 out of 5 average rating, 136 reviews
Superhost
Condo in Castelnuovo dei Sabbioni, caviglia
Chianti La Pruneta, Michelangelo apartment
Dec 6 – 13
$93 per night
4.89 out of 5 average rating, 122 reviews
Superhost
Condo in Fiesole
Poggiolieto Studio - on hills 10' from city center
Apr 27 – May 4
$130 per night
4.87 out of 5 average rating, 151 reviews
Guest favorite
Condo in Morrona
Casa Luna-Splendida overlooking the pool and Tuscan nature
Jul 6 – 13
$144 per night
4.96 out of 5 average rating, 108 reviews
Guest favorite
Condo in Greve in Chianti
ROSA cosiest and romantic studio
Jul 20 – 27
$98 per night
4.86 out of 5 average rating, 149 reviews
Guest favorite
Condo in Castelnuovo Berardenga
Castello di Orgiale Charme Residenz
May 13 – 20
$249 per night
4.95 out of 5 average rating, 38 reviews
Guest favorite
Condo in Castellina in Chianti
Apartment with terrace and stunning view
Oct 25 – Nov 1
$86 per night
4.97 out of 5 average rating, 32 reviews

Home rentals with a private pool

Guest favorite
Cottage in San Filippo A Ponzano
Stone House with Exclusive Pool Codilungo in Chianti
Jan 6 – 13
$322 per night
4.98 out of 5 average rating, 169 reviews
Guest favorite
Villa in Castiglion d'orcia
Villa Vignalunga
Mar 3 – 10
$745 per night
4.95 out of 5 average rating, 74 reviews
Superhost
Home in San Casciano in Val di pesa
Tuscan Villa Featured Conde Nast Best Villas Italy
Jan 3 – 10
$581 per night
4.82 out of 5 average rating, 72 reviews
Guest favorite
Home in Tavarnelle Val di Pesa
Casa Luigi Suite with Exclusive Pool
Aug 30 – Sep 6
$257 per night
4.92 out of 5 average rating, 73 reviews
Guest favorite
Home in Pergaccio
Villa Pergo is an ancient charming country villa
May 2 – 9
$320 per night
5.0 out of 5 average rating, 32 reviews
Guest favorite
Villa in San Miniato
Villa with exclusive pool
Apr 18 – 25
$217 per night
4.86 out of 5 average rating, 37 reviews
Villa in Casino di Terra
Private Retreat in Tuscan Countryside
Sep 8 – 15
$650 per night
4.81 out of 5 average rating, 62 reviews
Guest favorite
Villa in Montalcino
Breathtaking Views from a Tuscan Villa
May 10 – 17
$978 per night
5.0 out of 5 average rating, 44 reviews
Guest favorite
Home in Greve in Chianti
Casa 360
Apr 8 – 15
$408 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Villa in San Casciano in Val di pesa
Charming villa with pool in the hills of Chianti
Oct 9 – 16
$396 per night
5.0 out of 5 average rating, 28 reviews
Home in San Gimignano
Sissi
Jul 6 – 13
$506 per night
4.85 out of 5 average rating, 13 reviews
Guest favorite
Home in Castiglion Fiorentino
Nido del Sorbino
Nov 2 – 9
$63 per night
5.0 out of 5 average rating, 9 reviews

Quick stats about vacation rentals with a pool in Siena

Total rentals

90 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

2.2K reviews

Nightly prices starting at

$30 before taxes and fees

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Rentals with pools