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Vacation rentals near Rocca of Montestaffoli
We found 1,836 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Rocca of Montestaffoli, scroll through and discover private vacation rentals to find the perfect home base for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.
Vacation rentals with weekly discounts - Rocca of Montestaffoli
Showing deals for:Nov 14 - Nov 21
Image gallery for Exclusive panoramic villa with private pool between Florence and Siena.
1010 out of 10 rating
Exceptional
(16 reviews)
Exclusive panoramic villa with private pool between Florence and Siena.
Certaldo, Toscana
10% off
Price is CA $4,630
CA $4,630
CA $33,745 total
CA $33,745 total
includes taxes & fees
Image gallery for VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge
1010 out of 10 rating
Exceptional
(38 reviews)
VILLA BELSOLE - Certaldo Tuscany HEATED POOL and electric car recharge
Certaldo, Tuscany
19% off
Price is CA $977
CA $977
CA $8,531 total
CA $8,531 total
includes taxes & fees
Image gallery for Casa Del Grifone, vacation home in Tuscany.
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Casa Del Grifone, vacation home in Tuscany.
Volterra, Provincia di Pisa
10% off
Price is CA $564
CA $564
CA $5,190 total
CA $5,190 total
includes taxes & fees
Image gallery for FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
9.49.4 out of 10 rating
Exceptional
(18 reviews)
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Poggibonsi, Tuscany
10% off
Price is CA $203
CA $203
CA $1,749 total
CA $1,749 total
includes taxes & fees
Image gallery for San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
1010 out of 10 rating
Exceptional
(97 reviews)
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
San Gimignano, SI, Italy
10% off
Price is CA $796
CA $796
CA $6,180 total
CA $6,180 total
includes taxes & fees
Image gallery for Holiday house with private pool and fenced garden
1010 out of 10 rating
Exceptional
(57 reviews)
Holiday house with private pool and fenced garden
Volterra, Toskana
10% off
Price is CA $368
CA $368
CA $3,190 total
CA $3,190 total
includes taxes & fees
Image gallery for Podere le Monache - entire house in the tuscan hillside with spectacular view
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Podere le Monache - entire house in the tuscan hillside with spectacular view
Montaione, Toscana
5% off
Price is CA $611
CA $611
CA $7,305 total
CA $7,305 total
includes taxes & fees
Image gallery for The Photographer's House
1010 out of 10 rating
Exceptional
(11 reviews)
The Photographer's House
Colle di Val d'Elsa, Toscana
15% off
Price is CA $137
CA $137
CA $1,056 total
CA $1,056 total
includes taxes & fees
Image gallery for Perfect home base for exploring Tuscany w/private pool
8.88.8 out of 10 rating
Excellent
(18 reviews)
Perfect home base for exploring Tuscany w/private pool
Colle di Val d'Elsa, Provincia di Siena
13% off
Price is CA $199
CA $199
CA $1,530 total
CA $1,530 total
includes taxes & fees
Image gallery for RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
1010 out of 10 rating
Exceptional
(15 reviews)
RONDINE: Peaceful farmhouse close to Tuscany 's treasures, 1mile from shops far
Poggibonsi, Tuscany
10% off
Price is CA $159
CA $159
CA $1,479 total
CA $1,479 total
includes taxes & fees
Image gallery for Holiday House "La Sassolina"
1010 out of 10 rating
Exceptional
(8 reviews)
Holiday House "La Sassolina"
Montaione, Toscana
5% off
Price is CA $389
CA $389
CA $3,342 total
CA $3,342 total
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
10% off
Price is CA $159
CA $159
CA $1,479 total
CA $1,479 total
includes taxes & fees
Image gallery for PETIROSSO: Peaceful apt close to Tuscany 's best treasures, 1 mile from shops
9.09.0 out of 10 rating
Wonderful
(10 reviews)
PETIROSSO: Peaceful apt close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
10% off
Price is CA $166
CA $166
CA $1,535 total
CA $1,535 total
includes taxes & fees
Image gallery for Typical dwelling in the heart of the Tuscany between FLORENCE and SIENA
1010 out of 10 rating
Exceptional
(51 reviews)
Typical dwelling in the heart of the Tuscany between FLORENCE and SIENA
San Gimignano, Tuscany
5% off
Price is CA $183
CA $183
CA $1,461 total
CA $1,461 total
includes taxes & fees
Image gallery for PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops
9.29.2 out of 10 rating
Wonderful
(20 reviews)
PASSERO:Peaceful farmhouse close to Tuscany 's best treasures, 1 mile from shops
Poggibonsi, Tuscany
10% off
Price is CA $203
CA $203
CA $2,084 total
CA $2,084 total
includes taxes & fees
Image gallery for A Charming Authentic Manor House on the Chianti hills.
9.29.2 out of 10 rating
Wonderful
(5 reviews)
A Charming Authentic Manor House on the Chianti hills.
Gambassi Terme, Toscana
5% off
Price is CA $164
CA $164
CA $1,300 total
CA $1,300 total
includes taxes & fees
Image gallery for House in a typical village in the heart of Chianti
9.69.6 out of 10 rating
Exceptional
(72 reviews)
House in a typical village in the heart of Chianti
Castellina in Chianti, Tuscany
10% off
Price is CA $129
CA $129
CA $1,051 total
CA $1,051 total
includes taxes & fees
Image gallery for Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
1010 out of 10 rating
Exceptional
(107 reviews)
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano
San Gimignano, SI, Italy
10% off
Price is CA $796
CA $796
CA $6,180 total
CA $6,180 total
includes taxes & fees
Image gallery for La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
1010 out of 10 rating
Exceptional
(42 reviews)
La Casetta, Casole d'Elsa, Siena. Join the real Tuscany countryside!
Casole d'Elsa, Tuscany
19% off
Price is CA $169
CA $169
CA $1,378 total
CA $1,378 total
includes taxes & fees
Image gallery for Country House Nazzano in Vineyards/ near San Gimignano Florence Siena - Ro
9.69.6 out of 10 rating
Exceptional
(35 reviews)
Country House Nazzano in Vineyards/ near San Gimignano Florence Siena - Ro
Gambassi Terme
10% off
Price is CA $217
CA $217
CA $1,760 total
CA $1,760 total
includes taxes & fees
Image gallery for La Casetta del Borgo San Gimignano, relax nature swimming pool, STARLINK powered
9.69.6 out of 10 rating
Exceptional
(55 reviews)
La Casetta del Borgo San Gimignano, relax nature swimming pool, STARLINK powered
Gambassi Terme, Firenze
10% off
Price is CA $145
CA $145
CA $1,228 total
CA $1,228 total
includes taxes & fees
Image gallery for Wonderful Tuscan farmhouse in the Tuscan countryside
9.09.0 out of 10 rating
Wonderful
(28 reviews)
Wonderful Tuscan farmhouse in the Tuscan countryside
Colle di Val d'Elsa, Tuscany
10% off
Price is CA $130
CA $130
CA $1,559 total
CA $1,559 total
includes taxes & fees
Image gallery for Comfortable 2-bedroom apartment with 2 bathrooms near San Gimignano and Volterra
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Comfortable 2-bedroom apartment with 2 bathrooms near San Gimignano and Volterra
Montaione, Tuscany
10% off
Price is CA $174
CA $174
CA $1,722 total
CA $1,722 total
includes taxes & fees
Image gallery for Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
9.09.0 out of 10 rating
Wonderful
(20 reviews)
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Tavarnelle Val di Pesa, Tuscany
10% off
Price is CA $123
CA $123
CA $1,134 total
CA $1,134 total
includes taxes & fees
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Find properties near top attractions in Rocca of Montestaffoli
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Find the best place to stay - Rocca of Montestaffoli
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
66 reviews(66 reviews)
san gimignano apartment in historical center, courtyard and fast free wifi
Sleeps 4
9.69.6 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Holiday house with private pool and fenced garden
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
57 reviews(57 reviews)
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Sleeps 12 · 5 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
FABULOUS 8BR-8.5BA VILLA W PRIVATE HEATED POOL IN PRIME LOCATION NEAR FLORENCE!
Sleeps 16 · 8 bedrooms · 8+ bathrooms
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Country House & Spa - Inside Nature with panoramic views, Art Surrounded
Sleeps 29 · 9 bedrooms · 9+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
61 reviews(61 reviews)
Top rated rentals - Rocca of Montestaffoli
Birthday Celebration in Tuscany
1010 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
Great location
1010 out of 10
Exceptionalexceptional
105 reviews(105 reviews)
Breathtaking Property
1010 out of 10
Exceptionalexceptional
97 reviews(97 reviews)
Perfect and centrally located to visit all of Tuscany
1010 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Tuscany 2024
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Quiet, Relaxing Villa in a Beautiful Village!
1010 out of 10
Exceptionalexceptional
107 reviews(107 reviews)
Beautiful
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
Fantastic location
1010 out of 10
Exceptionalexceptional
15 reviews(15 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, yards and more
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