
Vacation rentals with a pool in Siena
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Siena

Total vacation rentals
Explore 100 vacation rentals in Siena

Nightly prices starting at
Siena vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

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Over 2,070 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Siena vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Siena rentals

4.7 Average rating
Siena stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Siena
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 143 reviews
Manor House - IlVillinoFarmhouse
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area
4.93 out of 5 average rating, 256 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient family-run property from the 1600s located in the beautiful hills of Chianti in Tuscany, with the possibility of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with incomparable sunsets.
5.0 out of 5 average rating, 353 reviews
Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.
4.96 out of 5 average rating, 142 reviews
Loggia 1 in farmhouse with shared pool
Apartment for 2 people in the Santa Lucia farmhouse (farmhouse DIVIDED IN 7 APARTMENTS) in the Crete Senesi, 10 km from Siena. Located on the second floor with a private 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), a bathroom with shower and a living room with functional kitchen. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room FOR A FEE according to consumption.
4.97 out of 5 average rating, 188 reviews
Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
4.97 out of 5 average rating, 162 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 108 reviews
Farmhouse in Chianti with Swimming Pool
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.
4.99 out of 5 average rating, 516 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
4.89 out of 5 average rating, 311 reviews
La Loggia. House with pool and stunning view
LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.
4.99 out of 5 average rating, 104 reviews
Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.
4.96 out of 5 average rating, 209 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
4.91 out of 5 average rating, 101 reviewsPopular amenities for Siena rentals with a pool
House rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 138 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 123 reviews
Borgo Ripostena – n. 9 Frantoio
4.94 out of 5 average rating, 118 reviews
Relaxation and charm in the Chianti hills
4.99 out of 5 average rating, 115 reviews
Casa Giulia di Sopra Farmhouse
4.95 out of 5 average rating, 107 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
4.9 out of 5 average rating, 129 reviews
Conca d'Oro villa with private pool, sleeps 4
4.92 out of 5 average rating, 173 reviews
House Rigomagno Siena
4.96 out of 5 average rating, 125 reviewsCondo rentals with a pool

La Casetta
4.93 out of 5 average rating, 197 reviews
House between Firenze, Arezzo, chianti e Siena
4.84 out of 5 average rating, 302 reviews
Apt. Panzanello-Panzano in Chianti
4.96 out of 5 average rating, 282 reviews
[Ninfea] Ancient House in Tuscany
4.92 out of 5 average rating, 121 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 138 reviews
Manuela apartment with pool in farmhouse
4.97 out of 5 average rating, 119 reviews
Vintage Residence with Pool in Chianti
4.96 out of 5 average rating, 149 reviewsHome rentals with a private pool

Stone House with Exclusive Pool Codilungo in Chianti
4.98 out of 5 average rating, 218 reviewsWp Relais Villa Vignalunga
4.93 out of 5 average rating, 117 reviews
TREEhouse/casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Esplora la natura al centro di Vigneti Chianti
4.97 out of 5 average rating, 265 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 122 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviewsWhen is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 962 | ﺩ.ﺇ 1,047 | ﺩ.ﺇ 973 | ﺩ.ﺇ 981 | ﺩ.ﺇ 1,069 | ﺩ.ﺇ 1,186 | ﺩ.ﺇ 1,083 | ﺩ.ﺇ 955 | ﺩ.ﺇ 1,014 | ﺩ.ﺇ 948 | ﺩ.ﺇ 848 | ﺩ.ﺇ 859 |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
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