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Vacation rentals in Castiglione della Pescaia

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Top-rated vacation rentals in Castiglione della Pescaia

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A scenic view of the villa's exterior is captured, featuring a terracotta roof and lush greenery. The vibrant colors of blooming flowers are visible alongside a panoramic view of the sea and coastal town below, enhancing the natural beauty of the surroundings.
Vacation home in Castiglione della Pescaia
4.77 out of 5 average rating, 13 reviews

Panoramic villa with a terrace overlooking the sea

Just an 8-minute walk from the sea, this 150-square-meter villa surrounded by greenery, located on the first floor, offers a breathtaking view of the sea and the beach of Castiglione della Pescaia. Bright and spacious, it has 4 bedrooms, 3 bathrooms (2 with shower), a living room, an equipped kitchen, and a washing machine. The highlight is the panoramic terrace and the sea-view loft, perfect for relaxing at sunset. With free Wi-Fi and air conditioning, it is ideal for those looking for nature, comfort and relaxation in Maremma.

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
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Vacation home in Sovicille
4.97 out of 5 average rating, 148 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

Guest favorite
A scenic view features a tranquil landscape with rolling hills in the distance. Tall trees frame the image, providing shade to a stone patio. The outdoor area includes comfortable seating, inviting guests to relax while enjoying the surrounding natural beauty.
Home in Castiglione della Pescaia
5 out of 5 average rating, 16 reviews

Casa Vista Sea and Maremma

Welcome to your peaceful oasis in Castiglione della Pescaia! Located in a quiet residential area, our house offers a magnificent view of the Maremma and is just a 15-minute walk from the historic center and a 5-minute drive from the beautiful beaches. Enjoy the perfect balance between relaxing in nature and seaside adventures, with the convenience of having all the attractions of the village at your fingertips. Your ideal getaway to discover the wonders of Tuscany awaits you.

Guest favorite
A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.
Cottage in Vetulonia
4.96 out of 5 average rating, 125 reviews

La Dolce Vita Romantic Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

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, 89 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, 231 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, 284 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.

Popular amenities for Castiglione della Pescaia vacation rentals

Quick stats about vacation rentals in Castiglione della Pescaia

  • Total rentals

    450 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    6.9K reviews

  • Family-friendly rentals

    250 properties are a good fit for families

  • Pet-friendly rentals

    220 properties allow pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

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.

Destinations to explore

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