Holiday rentals near Fortress of Montestaffoli
We found 5,372 holiday rentals — enter your dates for availability
Find the perfect holiday home within close proximity to Fortress of Montestaffoli. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Fortress of Montestaffoli
Showing deals for:17 Oct - 24 Oct
Image gallery for Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
1010 out of 10 rating
Exceptional
(39 reviews)
Wonderful Villa - Air Bubble Massage Pool - WiFi - max.14peopl
Greve in Chianti, Toscana
8% off
Price is AU$13,468
AU$13,468
AU$1,924 per night
includes taxes & fees
Image gallery for Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
1010 out of 10 rating
Exceptional
(6 reviews)
Stunning private Castle 9 BR - 8 BA with pool just 7 miles from Florence!
Impruneta, Toscana
9% off
Price is AU$39,545
AU$39,545
AU$5,649 per night
includes taxes & fees
Image gallery for traditional Tuscan Villa, the perfect retreat for families and friends
9.69.6 out of 10 rating
Exceptional
(10 reviews)
traditional Tuscan Villa, the perfect retreat for families and friends
Gambassi Terme, Tuscany
5% off
Price is AU$12,699
AU$12,699
AU$1,814 per night
includes taxes & fees
Image gallery for Melograno of Casale Refoli rural apartment 4 people
1010 out of 10 rating
Exceptional
(5 reviews)
Melograno of Casale Refoli rural apartment 4 people
Casole d'Elsa, Tuscany
9% off
Price is AU$2,353
AU$2,353
AU$336 per night
includes taxes & fees
Image gallery for VILLA BELLAVISTA-TUSCANY-POOL -JACUZZI- breath-taking view-great for family
9.69.6 out of 10 rating
Exceptional
(5 reviews)
VILLA BELLAVISTA-TUSCANY-POOL -JACUZZI- breath-taking view-great for family
Certaldo, Città Metropolitana di Firenze
15% off
Price is AU$10,438
AU$10,438
AU$1,491 per night
includes taxes & fees
Image gallery for Holiday home in the Florentine Chianti half an hour from Florence
9.89.8 out of 10 rating
Exceptional
(55 reviews)
Holiday home in the Florentine Chianti half an hour from Florence
Montespertoli, Toscana
9% off
Price is AU$3,074
AU$3,074
AU$439 per night
includes taxes & fees
Image gallery for Beautifully restored farmhouse in the heart of the Chianti
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Beautifully restored farmhouse in the heart of the Chianti
Greve in Chianti, Chianti
5% off
Price is AU$7,150
AU$7,150
AU$1,021 per night
includes taxes & fees
Image gallery for Cottage Gelsomino near Fiorenze, San Gimignano, Siena...
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Cottage Gelsomino near Fiorenze, San Gimignano, Siena...
Gambassi Terme, Tuscany
9% off
Price is AU$1,420
AU$1,420
AU$203 per night
includes taxes & fees
Image gallery for Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Splendid Chianti Tuscany Villa with Panoramic Pool ,Cypress Trees-Lined Drive
Montespertoli, Città Metropolitana di Firenze
9% off
Price is AU$8,652
AU$8,652
AU$1,236 per night
includes taxes & fees
Image gallery for "Borgo dei Fondi" Il Forno Ground Floor free wifi-free parking
1010 out of 10 rating
Exceptional
(20 reviews)
"Borgo dei Fondi" Il Forno Ground Floor free wifi-free parking
Siena, Tuscany
6% off
Price is AU$2,142
AU$2,142
AU$306 per night
includes taxes & fees
Image gallery for Delightful villa in the heart of Tuscany
1010 out of 10 rating
Exceptional
(54 reviews)
Delightful villa in the heart of Tuscany
Radicondoli, Tuscany
14% off
Price is AU$16,775
AU$16,775
AU$2,396 per night
includes taxes & fees
Image gallery for Small house with panoramic swimming pool, terrace and wi fi
1010 out of 10 rating
Exceptional
(5 reviews)
Small house with panoramic swimming pool, terrace and wi fi
Casole d'Elsa, Toscana
8% off
Price is AU$1,419
AU$1,419
AU$203 per night
includes taxes & fees
Image gallery for Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location
San Casciano in Val di Pesa, Toscana
8% off
Price is AU$11,526
AU$11,526
AU$1,647 per night
includes taxes & fees
Image gallery for Tuscan style house, independent, panoramic swimming pool, whirlpool, wi fi.
1010 out of 10 rating
Exceptional
(8 reviews)
Tuscan style house, independent, panoramic swimming pool, whirlpool, wi fi.
Peccioli, Toscana
8% off
Price is AU$1,950
AU$1,950
AU$279 per night
includes taxes & fees
Image gallery for Charming ancient farm house in Chianti
9.69.6 out of 10 rating
Exceptional
(43 reviews)
Charming ancient farm house in Chianti
Montespertoli, Toscana
9% off
Price is AU$4,872
AU$4,872
AU$696 per night
includes taxes & fees
Image gallery for House in a typical village in the heart of Chianti
9.69.6 out of 10 rating
Exceptional
(71 reviews)
House in a typical village in the heart of Chianti
Castellina in Chianti, Tuscany
9% off
Price is AU$1,632
AU$1,632
AU$233 per night
includes taxes & fees
Image gallery for Agriturismo San Silvestro - Your home with pool in the hills of Chianti
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Agriturismo San Silvestro - Your home with pool in the hills of Chianti
Barberino Val d'Elsa, Tuscany
9% off
Price is AU$2,925
AU$2,925
AU$418 per night
includes taxes & fees
Image gallery for FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
9.69.6 out of 10 rating
Exceptional
(17 reviews)
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,541
AU$1,541
AU$220 per night
includes taxes & fees
Image gallery for Villa Poggialto, breathtaking views, large pool and private spa in luxury
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Villa Poggialto, breathtaking views, large pool and private spa in luxury
Radicondoli
11% off
Price is AU$11,864
AU$11,864
AU$1,695 per night
includes taxes & fees
Image gallery for Exclusive and private Bio Farmhouse in the tuscani countryside
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Exclusive and private Bio Farmhouse in the tuscani countryside
Castelnuovo di Val di Cecina
9% off
Price is AU$3,368
AU$3,368
AU$481 per night
includes taxes & fees
Image gallery for RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
1010 out of 10 rating
Exceptional
(14 reviews)
RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
Poggibonsi, Tuscany
8% off
Price is AU$1,454
AU$1,454
AU$208 per night
includes taxes & fees
Image gallery for GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops
9.69.6 out of 10 rating
Exceptional
(15 reviews)
GUFO: Peaceful apartment close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
8% off
Price is AU$1,638
AU$1,638
AU$234 per night
includes taxes & fees
Image gallery for Ancient house in Chianti Hills with private lake and garden
1010 out of 10 rating
Exceptional
(5 reviews)
Ancient house in Chianti Hills with private lake and garden
Radda in Chianti, Tuscany
8% off
Price is AU$1,790
AU$1,790
AU$256 per night
includes taxes & fees
Image gallery for Lovely country house in the Chianti region, for 4 persons, near Siena
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Lovely country house in the Chianti region, for 4 persons, near Siena
Castellina in Chianti, Tuscany
14% off
Price is AU$1,944
AU$1,944
AU$278 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Fortress of Montestaffoli
san gimignano apartment in historical center, courtyard and fast free wifi
Sleeps 4
9.69.6 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
63 reviews(63 reviews)
Holiday house with private pool and fenced garden
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
Sleeps 29 · 9 bedrooms · 9+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
58 reviews(58 reviews)
LUXURY COTTAGE WITH POOL & BREATHTAKING VIEW - NEXT TO A GOLF COURSE (PENDOLINO)
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
51 reviews(51 reviews)
House with character in typical medieval borgo on the Chianti Classico hills
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
49 reviews(49 reviews)
Top rated rentals - Fortress of Montestaffoli
Modern amenities
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Beautiful farmhouse in Chianti
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value