Tuscany
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Rent a Luxury Villa with a Swimming Pool in Tuscany

Holiday rentals with private swimming pool in Tuscany, Italy

Discover our handpicked villas with private pools in Tuscany, from the rolling hills of Val d’Orcia to Chianti, Arezzo, Florence, and Siena. Each house combines elegant interiors with gardens, some offering heated pools, tennis courts, or the services of a private chef and house staff. A refined setting for family holidays and Italian living. Explore also our full collection of villas in Tuscany.
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Tuscany

  1. ArezzoExternal link
  2. ChiantiExternal link
  3. FlorenceExternal link
  4. GrossetoExternal link
  5. LuccaExternal link
  6. PisaExternal link
  7. PistoiaExternal link
  8. San GimignanoExternal link
  9. SienaExternal link
  10. Val d'OrciaExternal link

Number of rooms

  1. 3+
  2. 4+
  3. 5+
  4. 6+
  5. 7+
  6. 8+

Equipment and Services

  1. Swimming pool
  2. Heated swimming poolExternal link
  3. Secure pool
  4. Indoor swimming pool
  5. House staff
  6. Chef or Cook
  7. Self catering
  8. Garden
  9. Private parking space
  10. Jacuzzi
  11. Spa
  12. Tennis
  13. Fitness room
  14. Yoga
  15. Playroom - Game room
  16. Billard
  17. Cinema lounge
  18. Children welcome
  19. Party and Wedding

Themes

  1. Child-friendly villasExternal link
  2. City breaksExternal link
  3. Corporate retreat villasExternal link
  4. Countryside villasExternal link
  5. Event villasExternal link
  6. Family friendly villasExternal link
  7. Fully staffed villasExternal link
  8. Heated pool villasExternal link
  9. Large group villasExternal link
  10. Long week-end short stay villasExternal link
  11. Pet-friendly villasExternal link
  12. Pretty villas with low pricesExternal link
  13. Resort villasExternal link
  14. Spa villasExternal link
  15. Tennis villasExternal link
  16. Villas for photo shootsExternal link
  17. Villas near the cityExternal link
  18. Villas with a gardenExternal link
  19. Villas with chefExternal link
  20. Villas with extra privacyExternal link
  21. Villas with gymExternal link
  22. Villas with jacuzziExternal link
  23. Villas with swimming poolExternal link
  24. Wedding villasExternal link
  25. Wheelchair accessible villasExternal link
  26. Wine region villasExternal link
  27. Yoga villasExternal link

Types of property

  1. Architectural villasExternal link
  2. Historic estatesExternal link
  3. Luxury villasExternal link
79 Villa Villas

Villa Massa

(2 reviews)
357 € - 1 228 € per night
Traveler 10 (12 max.) Rooms 5 Bathroom 5

Tuscany - Pistoia

Villa Monteroni

(2 reviews)
2 116 € - 3 428 € per night
Traveler 14 (18 max.) Rooms 9 Bathroom 8

Tuscany - Siena

Casa Pippo

(1 review)
333 € - 742 € per night
Traveler 6 (8 max.) Rooms 3 Bathroom 3

Tuscany - Lucca - Forte dei Marmi

Villa Maestani

(1 review)
1 421 € - 1 998 € per night
Traveler 14 Rooms 9 Bathroom 5

Tuscany - Arezzo - Lucignano

Villa Victorina

(4 reviews)
1 410 € - 2 700 € per night
Traveler 14 Rooms 7 Bathroom 7

Tuscany - Val d'Orcia - San Casciano dei Bagni
1 100 € - 2 400 € per night
Traveler 12 (14 max.) Rooms 7 Bathroom 7

Tuscany - Siena
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Our destination experts as well as our concierge service will help organise your ideal vacation

2 142 € - 2 857 € per night
Traveler 15 Rooms 8 Bathroom 8

Tuscany - Lucca - Vorno
4 285 € - 4 857 € per night
Traveler 16 Rooms 8 Bathroom 7

Tuscany - Val d'Orcia - Buonconvento
642 € - 1 100 € per night
Traveler 10 Rooms 5 Bathroom 5

Tuscany - Arezzo
1 142 € - 2 128 € per night
Traveler 11 (13 max.) Rooms 7 Bathroom 7

Tuscany - Chianti - Tavernelle Val Di Pesa

Villa Rivela

(3 reviews)
885 € - 1 771 € per night
Traveler 6 (7 max.) Rooms 3 Bathroom 4

Tuscany - Pisa

Villa Parsina

(1 review)
307 € - 600 € per night
Traveler 8 Rooms 4 Bathroom 2

Tuscany - Lucca - San Martino in Freddana
557 € - 1 085 € per night
Traveler 8 (11 max.) Rooms 4 Bathroom 3

Tuscany - Pistoia
1 680 € - 3 500 € per night
Traveler 10 Rooms 5 Bathroom 5

Tuscany - Florence
3 142 € - 4 214 € per night
Traveler 22 (24 max.) Rooms 12 Bathroom 12

Tuscany - Lucca - Vorno

Villa Catherina

(6 reviews)
875 € - 1 588 € per night
Traveler 8 Rooms 5 Bathroom 5

Tuscany - Val d'Orcia - Montepulciano
592 € - 1 057 € per night
Traveler 6 (8 max.) Rooms 4 Bathroom 4

Tuscany - Val d'Orcia - Castelmuzio
2 857 € - 3 928 € per night
Traveler 12 (14 max.) Rooms 7 Bathroom 6

Tuscany - Chianti
2 300 € - 7 200 € per night
Traveler 16 (22 max.) Rooms 11 Bathroom 10

Tuscany - Florence

Villa Farfalla

(3 reviews)
2 571 € - 2 714 € per night
Traveler 12 (14 max.) Rooms 6 Bathroom 6

Tuscany - Lucca

Villa Amandina

(3 reviews)
485 € - 900 € per night
Traveler 10 Rooms 5 Bathroom 5

Tuscany - Arezzo

Villa Bart

(1 review)
1 285 € - 2 128 € per night
-20%
Traveler 12 (14 max.) Rooms 6 Bathroom 7

Tuscany - Val d'Orcia - Sarteano
603 € - 1 190 € per night
-35%
Traveler 10 (13 max.) Rooms 5 Bathroom 3

Tuscany - San Gimignano
635 € - 1 245 € per night
-25%
Traveler 8 (11 max.) Rooms 4 Bathroom 5

Tuscany - San Gimignano

Villa Cielo

(1 review)
228 € - 685 € per night
Traveler 10 Rooms 5 Bathroom 5

Tuscany - Arezzo - Ripoli
628 € - 928 € per night
Traveler 12 Rooms 6 Bathroom 7

Tuscany - Arezzo

Casa Maria

(1 review)
801 € - 1 098 € per night
Traveler 10 Rooms 5 Bathroom 4

Tuscany - Val d'Orcia - La Vittoria
828 € - 1 300 € per night
Traveler 18 Rooms 9 Bathroom 11

Tuscany - Arezzo - Cortone
1 428 € - 2 428 € per night
Traveler 12 (14 max.) Rooms 6 Bathroom 7

Tuscany - Val d'Orcia - Castiglioncello del Trinoro
3 600 € - 6 200 € per night
Traveler 18 Rooms 9 Bathroom 11

Tuscany - Florence
2 200 € - 3 125 € per night
Traveler 12 (14 max.) Rooms 6 Bathroom 7

Tuscany - Pistoia
1 542 € - 2 464 € per night
Traveler 10 Rooms 5 Bathroom 6

Tuscany - Florence - Castelfiorentino
1 157 € - 1 540 € per night
Traveler 14 Rooms 7 Bathroom 7

Tuscany - Val d'Orcia - La Vittoria

Villa Duchessa

(3 reviews)
510 € - 1 000 € per night
Traveler 12 Rooms 6 Bathroom 6

Tuscany - Arezzo

Villa Pistoia

(1 review)
700 € - 1 400 € per night
Traveler 15 (19 max.) Rooms 7 Bathroom 7

Tuscany - Pistoia
1 428 € - 3 035 € per night
Traveler 16 (19 max.) Rooms 8 Bathroom 9

Tuscany - Val d'Orcia - La Vittoria
2 657 € - 4 485 € per night
Traveler 10 (12 max.) Rooms 6 Bathroom 6

Tuscany - Chianti - Gaiole in Chianti
1 714 € - 2 285 € per night
Traveler 14 Rooms 7 Bathroom 7

Tuscany - Lucca - Vorno

Podere Bachi

(1 review)
803 € - 1 517 € per night
Traveler 10 Rooms 5 Bathroom 6

Tuscany - Val d'Orcia - Castiglioncello del Trinoro
1 214 € - 1 928 € per night
Traveler 12 Rooms 6 Bathroom 5

Tuscany - Chianti - Tavernelle Val Di Pesa
per night 1 828 €
Traveler 8 (12 max.) Rooms 4 Bathroom 4

Tuscany - Val d'Orcia - Montepulciano
1 257 € - 1 971 € per night
Traveler 18 (20 max.) Rooms 9 Bathroom 9

Tuscany - Arezzo - Pietraviva
500 € - 1 121 € per night
Traveler 10 (13 max.) Rooms 5 Bathroom 6

Tuscany - Pistoia
1 357 € - 2 142 € per night
Traveler 18 (20 max.) Rooms 9 Bathroom 10

Tuscany - Val d'Orcia - Buonconvento

Podere Lino

(1 review)
1 428 € - 3 214 € per night
Traveler 18 (19 max.) Rooms 9 Bathroom 9

Tuscany - Val d'Orcia - La Vittoria
2 800 € - 4 430 € per night
Traveler 16 Rooms 8 Bathroom 12

Tuscany - Grosseto
928 € - 1 285 € per night
Traveler 10 Rooms 6 Bathroom 4

Tuscany - Val d'Orcia - Chianciano Terme
722 € - 1 042 € per night
Traveler 8 Rooms 4 Bathroom 4

Tuscany - Val d'Orcia - Chianciano Terme
1 307 € - 2 928 € per night
Traveler 10 Rooms 5 Bathroom 6

Tuscany - San Gimignano
2 142 € - 3 285 € per night
Traveler 14 Rooms 7 Bathroom 7

Tuscany - Lucca - Vorno
892 € - 1 696 € per night
Traveler 10 (11 max.) Rooms 5 Bathroom 6

Tuscany - Val d'Orcia - Castiglioncello del Trinoro
514 € - 1 085 € per night
Traveler 22 Rooms 10 Bathroom 10

Tuscany - Pisa - Palaia

Villa Marco

(1 review)
1 008 € - 1 428 € per night
Traveler 12 Rooms 6 Bathroom 6

Tuscany - Lucca - San Martino in Freddana
1 285 € - 2 500 € per night
Traveler 20 Rooms 10 Bathroom 9

Tuscany - Chianti - Tavernelle Val Di Pesa
3 314 € - 4 428 € per night
Traveler 24 Rooms 12 Bathroom 12

Tuscany - Lucca - Vorno
300 € - 1 057 € per night
Traveler 12 Rooms 6 Bathroom 7

Tuscany - Arezzo - Ripoli
1 171 € - 2 564 € per night
Traveler 14 (19 max.) Rooms 9 Bathroom 9

Tuscany - Val d'Orcia - Biancacamicia
942 € - 1 285 € per night
Traveler 12 (14 max.) Rooms 7 Bathroom 7

Tuscany - Val d'Orcia - Trequanda
1 000 € - 1 500 € per night
Traveler 10 Rooms 5 Bathroom 5

Tuscany - Val d'Orcia - Pienza
2 895 € - 4 595 € per night
Traveler 10 Rooms 5 Bathroom 5

Tuscany - Siena - Pievescola
Contact us

Our destination experts as well as our concierge service will help organise your ideal vacation

Contact us

Our destination experts as well as our concierge service will help organise your ideal vacation

Luxury Tuscan villas to rent with heated pools, tennis courts and more

From a swimming pool overlooking the Val d’Orcia to an infinity pool framed by olive trees, each villa offers the perfect setting for relaxation. Heated pools in your villa extend the pleasure of bathing beyond summer, while terraces invite long evenings al fresco with fine local food. Interiors combine refinement and comfort, opening onto gardens designed for moments of tranquillity or convivial gatherings.

Holiday house rentals with pool near Florence, Siena and the tuscan coast

Our villas with private pool are ideally located near San Gimignano, Siena, and the Tuscan coast, with alternatives in nearby destinations such as Florence and Lucca. You can discover Tuscany and its culture and nature thanks to your villa with a swimming pool in Val d'Orcia, Arezzo or even in the famous Chianti. Whether in the countryside or closer to the River Arno, each villa with pool provides privacy while allowing easy access to the treasures of the region.

Tailored holiday services: From private chef to family care

Our concierge service brings peace of mind with discreet and tailored arrangements. From a private chef preparing seasonal food, to spa treatments, yoga sessions, vineyard visits or private transfers, every detail is coordinated to suit your wishes. House staff can be arranged, ensuring comfort throughout your stay while you remain free to enjoy your time in Tuscany.

Discover all Tuscany from your holiday letting with pool

Tuscany reveals itself through its UNESCO World Heritage Sites, from the towers of San Gimignano to the palaces of Siena. The landscapes of the Val d’Orcia invite slow exploration on foot or by bike of the emblematic villages of the Val d’Orcia. The Tuscan coast offers sandy escapes by the water, while inland you can discover unique nature experiences such as wild swimming spots in Tuscany. Days here are shaped by encounters with art, tradition, and gastronomy deeply rooted in the land.

As the day ends, returning to your villa means another swim in your private pool, a glass of wine under the cypress trees, and the sound of bells drifting across the hills. More than a holiday, it is an immersion into the essence of Tuscany.


Frequently Asked Questions

How does VILLANOVO select the villas?

VILLANOVO seeks villas offering unique and unforgettable experiences to its occupants. Exceptional geographical location, personalised services, luxury amenities and authenticity of the house are some of the criteria allowing us to add a house to our catalogue. The opinions of holidaymakers and the flexibility of the owners are also taken into account.

What is the price of a villa rental in the destination Tuscany?

Villanovo offers 79 villas in the destination Tuscany with prices ranging from 0 € to 0 € overnight. These rates include travel tips, personalised support throughout the stay and other options included with the rental of the villa.