Search 105,200+ Vacation Rentals

Gaiole in Chianti Vacation Rentals & Homes - 38 Rentals Available

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

38 Vacation rentals

1 / 13

Gaiole in Chianti Villa

  • 1
  • 2
  • Min stay varies
  • Swimming pool
  • Child friendly

from $140 / night

1 / 22

Gaiole in Chianti Villa

  • 7
  • 13
  • 3 nights min
  • Swimming pool

$1657

Inquire

from $1657 / night

1 / 36

Gaiole in Chianti House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly

from $161 / night

1 / 77

Gaiole in Chianti Castle

  • 4
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $354 / night

1 / 18

Gaiole in Chianti House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children

$504

Book

from $504 / night

1 / 32

Gaiole in Chianti Apartment

  • 4
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$308

Book

from $308 / night

1 / 21

Gaiole in Chianti House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$535

Book

from $535 / night

1 / 29

Gaiole in Chianti Villa

  • 4
  • 10
  • Min stay varies
  • Child friendly

$3500

Book

from $3500 / night

1 / 25

Gaiole in Chianti Villa

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $275 / night

1 / 38

Gaiole in Chianti Apartment

  • 4
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$334

Book

from $334 / night

1 / 36

Gaiole in Chianti House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $161 / night

1 / 30

Gaiole in Chianti House

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $110 / night

1 / 32

Gaiole in Chianti House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $161 / night

1 / 21

Gaiole in Chianti House

  • 3
  • 50
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$203

Book

from $203 / night

1 / 27

Gaiole in Chianti Apartment

  • 3
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$261

Book

from $261 / night

1 / 30

Gaiole in Chianti Apartment

  • 2
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$202

Book

from $202 / night

1 / 16

Gaiole in Chianti Villa

  • 6
  • 11
  • 7 nights min
  • Ask about children
  • Ask about pets

$825

Book

from $825 / night

1 / 27

Gaiole in Chianti Villa

  • 4
  • 8
  • 7 nights min
  • Child friendly
  • Air conditioning

$342

Book

from $342 / night

1 / 16

Gaiole in Chianti Villa

  • 5
  • 9
  • 7 nights min
  • Ask about children
  • Ask about pets

$673

Book

from $673 / night

1 / 35

Gaiole in Chianti Apartment

  • 3
  • 50
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$334

Book

from $334 / night

1 / 35

Gaiole in Chianti House

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $127 / night

1 / 26

Gaiole in Chianti Apartment

  • 3
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $246 / night

1 / 30

Gaiole in Chianti Apartment

  • 3
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $329 / night

1 / 30

Gaiole in Chianti Apartment

  • 4
  • 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $301 / night

1 / 30

Gaiole in Chianti Apartment

  • 4
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $329 / night

1 / 30

Gaiole in Chianti Villa

  • 5
  • 10
  • 7 nights min
  • Child friendly
  • Ask about pets

from $371 / night

1 / 31

Gaiole in Chianti Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly

from $516 / night

(1)

1 / 36

Gaiole in Chianti House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$542

Excellent (1 reviews)

Inquire

from $542 / night

1 / 12

Gaiole in Chianti House

  • 5
  • 18
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Ask about pets

from $592 / night

1 / 18

Gaiole in Chianti Villa

  • 3
  • 6
  • 7 nights min
  • Child friendly

$465

Book

from $465 / night

1 / 20

Gaiole in Chianti Apartment

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $244 / night

1 / 19

Gaiole in Chianti Apartment

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $244 / night

(2)

1 / 30

Gaiole in Chianti Villa

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$600

Excellent (2 reviews)

Inquire

from $600 / night

1 / 16

Gaiole in Chianti Villa

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $568 / night

1 / 30

Gaiole in Chianti Villa

  • 11
  • 22
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $409 / night

1 / 25

Gaiole in Chianti Villa

  • 4
  • 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $208 / night

1 / 19

Gaiole in Chianti Villa

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $582 / night

1 / 17

Gaiole in Chianti Villa

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $198 / night

Your search has been expanded 4.3 miles to include more rentals

1 / 41

Radda in Chianti House - 0.1 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1607

Inquire

from $1607 / night

(1)

1 / 65

Tuscany Villa - 0.1 miles away

  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$498

Excellent (1 reviews)

Book

from $498 / night

1 / 49

Ambra Villa - 0.1 miles away

  • 18
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1391

Inquire

from $1391 / night

1 / 18

Castellina In Chianti House - 1.1 miles away

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $545 / night

(6)

1 / 13

Tuscany Villa - 1.3 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Ask about pets

$503

Excellent (6 reviews)

Book

from $503 / night

1 / 32

Radda in Chianti Villa - 1.8 miles away

  • 7
  • 13
  • 3 nights min
  • Child friendly

$2691

Book

from $2691 / night

(5)

1 / 31

Tuscany Villa - 2.4 miles away

  • 5
  • 10
  • 7 nights min
  • Ask about children
  • Ask about pets

$1606

Excellent (5 reviews)

Book

from $1606 / night

1 / 25

Moncioni Apartment - 2.5 miles away

  • 7
  • 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $111 / night

1 / 31

Radda in Chianti Villa - 2.8 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $209 / night

1 / 58

Radda in Chianti House - 2.8 miles away

  • 3
  • 50
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

$195

Book

from $195 / night

1 / 39

Montegonzi House - 2.9 miles away

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets

from $455 / night

1 / 19

Radda in Chianti Villa - 3.1 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $296 / night

1 / 19

Vagliagli Villa - 3.3 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $218 / night

1 / 40

Cavriglia House - 3.3 miles away

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$533

Book

from $533 / night

1 / 45

Radda in Chianti Villa - 3.3 miles away

  • 14
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1916

Inquire

from $1916 / night

1 / 27

Radda in Chianti Villa - 3.4 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+

$787

Book

from $787 / night

1 / 30

Volpaia Apartment - 3.5 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $544 / night

1 / 23

Tuscany Villa - 3.6 miles away

  • 5
  • 9
  • 7 nights min
  • Ask about children
  • Ask about pets

$601

Book

from $601 / night

1 / 28

Volpaia Villa - 3.6 miles away

  • 6
  • 12
  • 7 nights min
  • Child friendly

$372

Book

from $372 / night

1 / 29

Radda in Chianti House - 3.6 miles away

  • 6
  • 50
  • 7 nights min
  • Swimming pool
  • Child friendly

$506

Book

from $506 / night

1 / 24

Volpaia Villa - 3.6 miles away

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Ask about children

$506

Book

from $506 / night

1 / 38

Radda in Chianti Villa - 3.7 miles away

  • 5
  • 9
  • 7 nights min
  • Child friendly

$553

Book

from $553 / night

1 / 31

Radda in Chianti Villa - 3.8 miles away

  • 5
  • 50
  • 7 nights min
  • Swimming pool
  • Child friendly

$844

Book

from $844 / night

(1)

1 / 31

Radda in Chianti House - 3.8 miles away

  • 5
  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children

$601

Excellent (1 reviews)

Book

from $601 / night

1 / 30

Radda in Chianti Villa - 3.8 miles away

  • 5
  • 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $676 / night

(1)

1 / 28

Radda in Chianti House - 3.8 miles away

  • 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1127

Very Good (1 reviews)

Inquire

from $1127 / night

1 / 30

Vagliagli Apartment - 3.9 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $262 / night

1 / 30

Vagliagli Apartment - 3.9 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $262 / night

1 / 30

Vagliagli Villa - 3.9 miles away

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $275 / night

1 / 32

Radda in Chianti Farmhouse - 4.2 miles away

  • 11
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

from $653 / night

1 / 35

Radda in Chianti House - 4.2 miles away

  • 6
  • 50
  • 7 nights min
  • Swimming pool
  • Child friendly

$506

Book

from $506 / night

(3)

1 / 24

Volpaia Villa - 4.2 miles away

  • 6
  • 11
  • 7 nights min
  • Swimming pool
  • Ask about children

$506

Very Good (3 reviews)

Book

from $506 / night

1 / 22

Volpaia Villa - 4.2 miles away

  • 6
  • 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $569 / night

1 / 30

Volpaia Apartment - 4.2 miles away

  • 6
  • 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $544 / night

(1)

1 / 35

Volpaia Villa - 4.2 miles away

  • 6
  • 11
  • 7 nights min
  • Child friendly

$466

Very Good (1 reviews)

Book

from $466 / night

(6)

1 / 15

Tuscany Villa - 4.3 miles away

  • 6
  • 11
  • 7 nights min
  • Ask about children
  • Ask about pets

$506

Very Good (6 reviews)

Book

from $506 / night

(4)

1 / 20

Volpaia Villa - 4.3 miles away

  • 3
  • 6
  • 7 nights min
  • Child friendly

$392

Very Good (4 reviews)

Book

from $392 / night

1 / 27

Radda in Chianti House - 4.3 miles away

  • 3
  • 50
  • 7 nights min
  • Swimming pool
  • Child friendly

$427

Book

from $427 / night

1 / 20

Volpaia House - 4.3 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children

$427

Book

from $427 / night

1 / 23

Volpaia Villa - 4.3 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from $480 / night