
Vacation rentals in Castiglione della Pescaia
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Top-rated vacation rentals in Castiglione della Pescaia
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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.

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.

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.

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.

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.

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.

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
Other great vacation rentals in Castiglione della Pescaia

Casa Lucrezia with garden overlooking the sea on the hill

A gem by the sea

Sensational semi-detached villa - Astonishing view

Comfortable house and terrace by the sea

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

Beach villa with parking

House with a terrace facing the sea

Beach apartment with private parking space
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
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- Apartment rentals Castiglione della Pescaia
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- Villa rentals Castiglione della Pescaia
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- Pet-friendly rentals Castiglione della Pescaia
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- Beachfront rentals Castiglione della Pescaia
- Rentals with beach access Castiglione della Pescaia
- House rentals Castiglione della Pescaia
- Elba
- Giglio Island
- Giannutri
- Feniglia
- Cala Violina
- Gulf of Baratti
- Spiaggia Di Sansone
- Spiaggia di Capo Bianco
- Kite Beach Fiumara
- Spiaggia Di Barbarossa
- Spiagge bianche
- Spiaggia della Padulella
- Spiaggia Marina di Cecina
- Spiaggia Zuccale
- Cala Di Forno
- Spiaggia di Patresi
- Marina di Grosseto beach
- Castiglion del Bosco Winery
- Spiaggia di Marina Di Campo
- Golf Club Toscana
- Riva del Marchese
- Spiaggia di Cavo
- Le Cannelle
- Santa Maria della Scala