See all properties

Chalet in Chianti with swimming pool and tennis court

Top rated by guests

Pool

Pool

Pool

Pool

Pool

Don't miss out! Price and availability may change

10.0 / 10.0

Outstanding(1 Rating)

House in Castellina in Chianti

5 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Well priced for this locationPriced under area average

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Located in Castellina in Chianti, this welcoming vacation home brings it all within your reach. With convenient onsite parking, you'll be ready to make the 15-minute drive to Monteriggioni Castle or the 22-minute drive to Isole e Olena Winery.

Relax by the communal pool or sip a drink in the garden of this vacation home, which also features a firepit and outdoor furniture. As for the great indoors, you can come inside and enjoy the WiFi.

A BBQ grill, a fireplace, and air conditioning are featured at this 2-bedroom, 2-bathroom rental. Bathroom amenities include a hair dryer, a bidet, and towels. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an electric kettle, and a lobster pot. And you can even travel light because you'll have access to laundry facilities.

Families will appreciate the children's dinnerware, travel crib, and highchair at this property. There is also a playground for the kids to enjoy, as well as books to spark their creativity.

Amenities at Chalet in Chianti with swimming pool and tennis court

Pets allowed

Family friendly

Map of Castellina in Chianti

city location on map

Nearby attractions

Piazza del Campo

Abbazia di San Galgano

Cupola del Brunelleschi

Museum of Opera of Saint Maria of Fiore

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

$$$$

Top rated by guests

Don't miss out! Price and availability may change

$$$$

10.0 / 10.0

Outstanding(1 Rating)

House in Castellina in Chianti

5 guests · 2 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Well priced for this locationPriced under area average

Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

Map of Castellina in Chianti

city location on map

Nearby attractions

Piazza del Campo

Abbazia di San Galgano

Cupola del Brunelleschi

Museum of Opera of Saint Maria of Fiore

About this house rental

Located in Castellina in Chianti, this welcoming vacation home brings it all within your reach. With convenient onsite parking, you'll be ready to make the 15-minute drive to Monteriggioni Castle or the 22-minute drive to Isole e Olena Winery.

Relax by the communal pool or sip a drink in the garden of this vacation home, which also features a firepit and outdoor furniture. As for the great indoors, you can come inside and enjoy the WiFi.

A BBQ grill, a fireplace, and air conditioning are featured at this 2-bedroom, 2-bathroom rental. Bathroom amenities include a hair dryer, a bidet, and towels. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an electric kettle, and a lobster pot. And you can even travel light because you'll have access to laundry facilities.

Families will appreciate the children's dinnerware, travel crib, and highchair at this property. There is also a playground for the kids to enjoy, as well as books to spark their creativity.

Amenities

Pets allowed

Family friendly

Things to know

Additional fees to expect

Cleaning & other feesWe include all stay related fees in the Cleaning Fee line, which may include cleaning, property manager, resort, tourism and other stay related fees. All Vrbo properties are professionally cleaned after each stay.

Booking feeNo booking fees, easy credit card payments.

Service feeThis helps Vrbo provide a safer and more secure booking experience.

TaxesTaxes on accommodation such as Occupancy Tax, VAT, or GST. May also include tourism fees.

Customer support

Customer support is handled by our partner Vrbo

Explore similar stays in Castellina in Chianti

Explore all rentals in Castellina in Chianti

8.9 / 10.0

Excellent(59 Ratings)

Fattoria Casa Sola

in Barberino di Val dʼElsa

2 guests · 1 bedroom · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Castellina in Chianti at Fattoria Casa Sola for $93 for your next trip.

9.2 / 10.0

Outstanding(9 Ratings)

Fattoria Casa Sola

in Barberino Tavarnelle

4 guests · 2 bedrooms · 1 bath

Pool · Kitchen or Kitchenette · Internet / Wifi

The best choice in Castellina in Chianti for Farm Stay, for $110 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

9.0 / 10.0

Outstanding(9 Ratings)

Fattoria Casa Sola

in Barberino Tavarnelle

4 guests · 2 bedrooms · 1 bath

Pool · Kitchen or Kitchenette · Internet / Wifi

The best choice in Castellina in Chianti for Farm Stay, for $110 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

You can save with One Key

9.5 / 10.0

Outstanding(75 Ratings)

House in a typical village in the heart of Chianti

in Castellina in Chianti

5 guests · 2 bedrooms · 1 bath

Family friendly

When traveling to Castellina in Chianti, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $94 per night.

9.4 / 10.0

Outstanding(450 Ratings)

Agriturismo Casale Dello Sparviero

in Castellina in Chianti

2 guests · 2 bedrooms · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Enjoy the best of Castellina in Chianti in our Farm Stay, Agriturismo Casale Dello Sparviero. A stunning property with amenities including Parking, Pets allowed and Garden, and more.

9.2 / 10.0

Outstanding(416 Ratings)

Relais Riserva di Fizzano

in Castellina in Chianti

2 guests · 1 bedroom · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Are you ready to indulge in a relaxing getaway? Our Apartment in Castellina in Chianti has everything you need for a rejuvenating stay. Treat yourself to Relais Riserva di Fizzano's exceptional amenities, such as Parking, Pets allowed and Garden.

9.6 / 10.0

Outstanding(75 Ratings)

House in a typical village in the heart of Chianti

in Castellina in Chianti

5 guests · 2 bedrooms · 1 bath

Family friendly

This House for $94 in Castellina in Chianti, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

A San Donato holiday home

in San Donato in Poggio

5 guests · 3 bedrooms · 1 bath

Family friendly

Indulge in a peaceful retreat at A San Donato holiday home, our elegant House in Castellina in Chianti. Enjoy amenities including Family friendly, and more.

9.1 / 10.0

Outstanding(191 Ratings)

Romitorio di Serelle

in Barberino di Val dʼElsa

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Internet / Wifi

Soak up the beauty of Castellina in Chianti in our Apartment, Romitorio di Serelle. With a range of amenities such as Parking, Garden and Balcony or Patio, you'll feel right at home.

9.8 / 10.0

Outstanding(36 Ratings)

Borgo Sicelle

Vacation rental

in Barberino Tavarnelle

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Soak up the beauty of Castellina in Chianti in our Vacation rental, Borgo Sicelle. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

8.8 / 10.0

Excellent(7 Ratings)

Holiday Home Cignanbianco - Tramonto by Interhome

in Castellina in Chianti

6 guests · 3 bedrooms · 2 baths

Pool · Pets allowed · Kitchen or Kitchenette

Experience vacation in Castellina in Chianti with our House, Holiday Home Cignanbianco - Tramonto by Interhome. Enjoy amenities such as Parking, Pets allowed and Garden, and more.

9.4 / 10.0

Outstanding(75 Ratings)

Villa with large garden in the Chianti hills

5 guests · 3 bedrooms · 2 baths

Family friendly

Indulge in a peaceful retreat at Villa with large garden in the Chianti hills, our elegant House in Castellina in Chianti. Enjoy amenities including Family friendly, and more.

9.5 / 10.0

Outstanding(67 Ratings)

Nittardi

in Castellina in Chianti

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Nestled in Castellina in Chianti, this Farm Stay is perfect for your next vacation. Enjoy Nittardi's top-rated amenities, including Parking, Garden and Balcony or Patio, and more.

Golden Days in San Donato home

in San Donato in Poggio

6 guests · 3 bedrooms · 1 bath

Family friendly

Experience vacation in Castellina in Chianti with our House, Golden Days in San Donato home. Enjoy amenities such as Family friendly, and more.

8.7 / 10.0

Excellent(155 Ratings)

Fattoria Lornano Winery

in Monteriggioni

2 guests · 3 bedrooms · 2 baths

Pool · Pets allowed · Kitchen or Kitchenette

This attractive Farm Stay in Castellina in Chianti, $91 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

10.0 / 10.0

Outstanding(1 Rating)

Chalet in Chianti with swimming pool and tennis court

5 guests · 2 bedrooms · 2 baths

Pets allowed · Family friendly

This House for $100 in Castellina in Chianti, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

9.5 / 10.0

Outstanding(70 Ratings)

Borgo Sicelle Residence

in San Donato in Poggio

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

This inviting Apartment in Castellina in Chianti can fit your needs for many types of vacations, at $97 per night.

9.2 / 10.0

Outstanding(6 Ratings)

La Rocca della Magione

in Monteriggioni

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Castellina in Chianti, at $110 per night for your next great vacation.

7.6 / 10.0

Good(17 Ratings)

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

in Castellina in Chianti

6 guests · 2 bedrooms · 2 baths

Pool · Pets allowed · Kitchen or Kitchenette

Looking for a House in Castellina in Chianti, this House for $96 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

9.8 / 10.0

Outstanding(36 Ratings)

Borgo Sicelle

Vacation rental

in Barberino Tavarnelle

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Castellina in Chianti at Borgo Sicelle for $101 for your next trip.

You can save with One Key

Immersion in Chianti

in San Donato In Poggio

5 guests · 2 bedrooms · 1 bath

Pets allowed · Family friendly

Business stays, family stays, couples stay, getaway vacation, and rental in Castellina in Chianti at Immersion in Chianti for $99 for your next trip.

9.4 / 10.0

Outstanding(11 Ratings)

La Misura cottage with swimming pool

in Castellina in Chianti

6 guests · 4 bedrooms · 2 baths

Pool · Pets allowed · Kitchen or Kitchenette

Nestled in Castellina in Chianti, this House is perfect for your next vacation. Enjoy La Misura cottage with swimming pool's top-rated amenities, including Parking, Pets allowed and Garden, and more.

9.0 / 10.0

Outstanding(221 Ratings)

Casalta Di Pesa

2 guests · 2 bedrooms · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Nestled in Castellina in Chianti, this House is perfect for your next vacation. Enjoy Casalta Di Pesa's top-rated amenities, including Parking, Pets allowed and Garden, and more.

9.2 / 10.0

Outstanding(6 Ratings)

La Rocca della Magione

in Monteriggioni

2 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Castellina in Chianti? Our Farm Stay might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Balcony or Patio, and more during your stay.

10.0 / 10.0

Outstanding(2 Ratings)

Il Poderino

in Monteriggioni

3 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Internet / Wifi

The best choice in Castellina in Chianti for Farm Stay, for $115 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

9.0 / 10.0

Outstanding(151 Ratings)

La FIABA

in Castellina in Chianti

2 guests · 1 bedroom · 1 bath

Kitchen or Kitchenette · Internet / Wifi · Parking

Soak up the beauty of Castellina in Chianti in our Country House, La FIABA. With a range of amenities such as Parking, Garden and Balcony or Patio, you'll feel right at home.

9.4 / 10.0

Outstanding(73 Ratings)

Villa with large garden in the Chianti hills

5 guests · 3 bedrooms · 2 baths

Family friendly

Looking for a memorable stay in Castellina in Chianti? Our House might just be what you're looking for. Enjoy amenities including Family friendly, and more during your stay.

9.4 / 10.0

Outstanding(98 Ratings)

MEA CASA Toscana

in Castellina in Chianti

2 guests · 1 bedroom · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

When traveling to Castellina in Chianti, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $95 per night.

10.0 / 10.0

Outstanding(2 Ratings)

Il Poderino

in Monteriggioni

3 guests · 1 bedroom · 1 bath

Pool · Kitchen or Kitchenette · Internet / Wifi

Enjoy the best of Castellina in Chianti in our Farm Stay, Il Poderino. A stunning property with amenities including Internet / Wifi, Balcony or Patio and Kitchen or Kitchenette, and more.

9.1 / 10.0

Outstanding(401 Ratings)

Borgo Di Pietrafitta Relais

in Castellina in Chianti

2 guests · 1 bedroom · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Looking for a memorable stay in Castellina in Chianti? Our Apartment might just be what you're looking for. Enjoy amenities including Parking, Pets allowed and Garden, and more during your stay.