Some info has been automatically translated. Show original language

Vacation rentals in Castiglione della Pescaia

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Castiglione della Pescaia

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Guest favorite
A spacious outdoor pool is surrounded by neatly arranged lounge chairs and framed by lush greenery and tall cypress trees. The inviting blue water reflects the clear sky and the structure of the residence sits elegantly in the background.
Home in Asciano
4.96 out of 5 average rating, 101 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favorite
An inviting living space features a cozy fireplace framed by a rustic stone wall. Natural light filters through floral-patterned curtains, illuminating a spacious sitting area with a two-seater sofa. A four-poster bed draped in sheer fabric enhances the room's charm, complemented by decorative lanterns.
Apartment in Caminino
4.91 out of 5 average rating, 182 reviews

Pieve di Caminino Historic Farm

Solo per amanti della natura. L'antica fattoria Pieve di Caminino, biologica, è un importante sito storico: ex pieve medievale sorta all'incrocio di due strade romane, ospitò due santi (la chiesa del XII secolo è oggi un museo privato, visitabile dagli ospiti, su appuntamento). Oggi copre 200 ettari di proprietà privata recintata, posta su una collina panoramica. Sette alloggi condividono una tenuta con piscina (stagionale), due laghetti, un uliveto centenario, vigneto e una foresta di sughere.

Top guest favorite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 92 reviews

Captain's House | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Top guest favorite
A modern kitchen area is integrated with a cozy living space, featuring light-colored cabinetry and gray tile flooring. A comfortable seating arrangement includes a plush sofa. Two high stools are positioned beside a sleek table, creating an inviting space for meals or casual gatherings.
Home in Castiglione della Pescaia
5 out of 5 average rating, 50 reviews

Charming Salicornia near beach and town centre

Bright and brand new, this apartment is in a quiet location close to both the sea and the town centre, so you can forget about your car—everything is just steps away. This fully equipped 2-bedroom apartment has it all: a modern kitchen, mosquito nets, comfortable air conditioning, and even a cot and high chair for your little one. We’ve thought of every detail, including beach toys for added fun. Everything you need for a carefree stay is already here; just bring your personal belongings.

Top guest favorite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay in Seggiano
4.99 out of 5 average rating, 258 reviews

Terra Delle Sidhe, Seggiano, Tuscany, Italy

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Guest favorite
A serene bedroom is highlighted by a spacious bed adorned with a dark blue quilt. A wooden desk and lamp are positioned beside a window, showcasing expansive views of the sea and a distant lighthouse. Soft natural light fills the room through the window.
Apartment in Piombino
4.96 out of 5 average rating, 82 reviews

Seaside Retreat: Borgo alla Noce

Magnificent historic building overlooking the Tuscan Archipelago! The entire apartment offers a breathtaking view of the Island of Elba and direct access to the sea. Furnished with elegance and rustic/ modern style is the ideal place for your holidays!! A unique experience that combines history, culture and fun, perfect for exploring the Tuscan coast, its crystal clear waters and its history! The house is less than 5 minutes walk from all amenities.

Guest favorite
A charming stone cottage is depicted, featuring a dark roof and a welcoming entrance. Vibrant purple flowers in the foreground provide a splash of color against the gravel pathway, while warm sunlight casts a gentle glow, highlighting the serene surroundings.
Apartment in Castiglione della Pescaia
4.97 out of 5 average rating, 93 reviews

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay surrounded by nature.

Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.91 out of 5 average rating, 232 reviews

Casa al Gianni - Capanna

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Guest favorite
An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.
Apartment in Monteroni d'Arbia
4.95 out of 5 average rating, 261 reviews

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Top guest favorite
A light-filled living area features large glass windows, offering views of the surrounding nature. An orange armchair and a minimal dining table are visible, complemented by wooden cabinetry and kitchen appliances. Natural light illuminates the space, enhancing the warm tones of the decor.
Home in Marrucheti
4.98 out of 5 average rating, 160 reviews

La Stallina - Perfect retreat from the city rush

Recently restored, La Stallina, was my grandfather's horse stable at the beginning of last century. Now it is a charming apartment perfect for a couple and suitable for 2+2 guests. One living room with kitchen in a conservatory, double bed and mezzanine with bed. Bathroom with large shower box, kitchen equipped with dish-washing and oven.

Top guest favorite
A rustic terrace features a wooden table and chairs, offering panoramic views of rolling hills and lush greenery. Stone walls support a traditional wooden beam ceiling, while elements like a decorative bell and a sheep silhouette add character to the natural surroundings.
Farm stay in Pari
4.98 out of 5 average rating, 285 reviews

TUSCANY farm house SWIMMING POOL

Our little farm is a beautiful location for a relaxing vacation with a private swimming pool. We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

Guest favorite
A dining table is set on the terrace, featuring a crisp tablecloth and placemats. Fresh flowers are displayed in clear vases, with the sea and coastline visible in the background under a softly lit sky.
Apartment in Castiglione della Pescaia
5 out of 5 average rating, 17 reviews

Terrace with a sea view, weekends

Your unforgettable Vacation in the accommodation with a large terrace overlooking the sea: in the foreground the island of Giglio and Montecristo, then the Elba. The scent of the sea and the blue of the Maremma sky.

Popular amenities for Castiglione della Pescaia vacation rentals

Frequently Asked Questions

  • What types of vacation rentals are available in Castiglione della Pescaia?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Castiglione della Pescaia. From over 60 house rentals, over 10 villa rentals to over 280 apartment rentals, we've got you covered.

  • Are there vacation rentals with a dedicated workspace in Castiglione della Pescaia?

    Yes! Work meets play with ease at over 70 vacation rentals in Castiglione della Pescaia featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Castiglione della Pescaia?

    Four-legged friends are welcome in Castiglione della Pescaia. Choose from more than 220 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in condo rentals in Castiglione della Pescaia?

    Experience the best of Castiglione della Pescaia with our condo rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do apartment rentals in Castiglione della Pescaia have wifi?

    Absolutely! We offer over 170 apartment rentals with wifi in Castiglione della Pescaia. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Castiglione della Pescaia have a kitchen?

    Absolutely! We offer over 270 apartment rentals with a kitchen in Castiglione della Pescaia. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Castiglione della Pescaia have free parking?

    Absolutely! We offer over 30 condo rentals with free parking in Castiglione della Pescaia. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Castiglione della Pescaia have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Castiglione della Pescaia. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly villa rentals in Castiglione della Pescaia?

    Castiglione della Pescaia has more than 10 family-friendly villa rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Condo Rentals in Castiglione della Pescaia?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 60 homes with a kitchen, over 40 homes with wifi, over 30 homes with free parking, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Castiglione della Pescaia

  • Total vacation rentals

    Explore 450 vacation rentals in Castiglione della Pescaia

  • Nightly prices starting at

    Castiglione della Pescaia vacation rentals start at G$6,273 GYD per night before taxes and fees

  • Verified guest reviews

    Over 6,860 verified reviews to help you choose

  • Family-friendly vacation rentals

    250 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 220 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    280 of Castiglione della Pescaia vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Castiglione della Pescaia rentals

  • 4.7 Average rating

    Castiglione della Pescaia stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Castiglione della Pescaia