
Vacation rentals in Castiglione della Pescaia
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Top-rated vacation rentals in Castiglione della Pescaia
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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.

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.

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.

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.

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.

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.

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!

"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).

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.

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
Other great vacation rentals in Castiglione della Pescaia

Casa Lucrezia with garden overlooking the sea on the hill

Villa with a hydromassage pool

A gem by the sea

Private villa in Maremma 15 minutes from the sea

Comfortable house and terrace by the sea

6 people house 500 mt. from the sea and the center

The pomegranate, Podere il Giglio

Beach villa with parking
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.
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- Elba
- Giglio Island
- Giannutri
- Feniglia
- Cala Violina
- Gulf of Baratti
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Spiagge bianche
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Spiaggia Zuccale
- Spiaggia Marina di Cecina
- Cala Di Forno
- Spiaggia di Marina Di Campo
- Marina di Grosseto beach
- Spiaggia di Patresi
- Riva del Marchese
- Spiaggia di Cavo
- Castiglion del Bosco Winery
- Le Cannelle
- Golf Club Toscana
- CavallinoMatto