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A coastal town with a marina, buildings, and a river.

Castiglione della Pescaia Vacation Rentals

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Check prices for these dates, December 14 – 15, 2026

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Our top choices for Castiglione della Pescaia vacation rentals

1. Tramontana Room – Montecristo B&B Steps from the Sea

A hotel room with a bed, a map on the wall, a balcony with a view, and a towel with a logo.

2. Two-Room Apartment 'Remota 3' with Sea View and Air Conditioning

A coastal town with historic buildings, a prominent tower, and a marina with boats.

3. VILLA ALBA CHIARA - Six Bedroom Villa, Sleeps 12

A wooden beach cabana with a table set for two, overlooking the ocean.

4. PUNTA ALA: SUNSET WITH A VIEW OF THE OCEAN! Air conditioning + parking + Blue Flag beaches!

A coastal landscape with clear water, a sandy beach, and distant hills.

5. Apartment 'La Nicchia'

A cobblestone street with parked cars and buildings.

6. Charming Two-Room Apartment with Pool, a Dream Getaway

A beach with thatched umbrellas and sun loungers.

7. Maestrale Room - Montecristo B&B Steps from the Sea

A hotel room with a bed, a map on the wall, a balcony with a view, and a window with curtains.

8. Grecale Room - Montecristo B&B Steps from the Sea

A hotel room with a large map on the wall, a bed with a white comforter, and a view of the sea through a balcony.

9. Scirocco Room - B&B Montecristo with Sea View

A hotel room with a bed, a desk, a chair, a small table, a trash bin, and a map on the wall.

10. Three-Room Apartment in Castiglione della Pescaia Old Town with Sea View

A narrow street with buildings on either side, a sign indicating no parking, and a staircase leading to an upper level.

11. Appartamenti La Vecchia Posta

A hotel lobby with a reception desk, seating area, bookshelves, and large windows.

12. Pineta Azzurra

A residential area with multiple buildings, a balcony with a wooden railing, and a view of trees and a clear sky.

13. Botrona B&B

A person relaxing in a hot tub with a glass of wine.

14. Domus Socolatae Residenza d'Epoca Charming B&B

A person sitting in a bathtub with a tiled wall in the background.

15. Il Bennu

A garden with a variety of plants, a palm tree, and a glass table with decorative items.

16. Agriturismo Bio Femminella

A brick building with a covered patio area, a paved walkway, and surrounding greenery.

17. Pratoranieri Appartamenti & Suite

A modern kitchen with grey cabinets, a marble countertop, and a built-in oven. There is a dining area with a table and chairs, and a bed with a blue and white checkered bedspread in the background.

18. Marconi 1935 B&B and Holiday Home

A modern hotel room with a large bed, a bedside table with a lamp, a small round table, a bench with towels, a large window with curtains, and a sign on the wall that reads "BEACH".

19. Luci sul Mare

A modern living room with a sofa, a TV, a small potted plant, and a view of the outdoors.

20. Residence Il Boschetto

A spacious living area with a dining table, red chairs, and a small round table. Large windows provide natural light and views of greenery outside.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Apartments

Condos

Top Castiglione della Pescaia Hotel Reviews

Agriturismo Giù al Pozzo

An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

Castello Bonaria Wine & Spa Resort

A spa area with a hot tub surrounded by columns and a seating area with umbrellas.

Historic Farmhouse Casa del Chiodo

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

Hotel Terme Marine Leopoldo II

Two drinks with orange slices and straws by a poolside with a building in the background.

Sleep

An outdoor patio with a patterned floor, a brick wall, and a seating area with chairs and a table.

Marina di Scarlino Resort

A poolside area with lounge chairs and umbrellas, a wooden deck, and a clear blue sky.

Domus Socolatae Residenza d'Epoca Charming B&B

A person sitting in a bathtub with a tiled wall in the background.

Maestrale Resort Hotel - Alberese, Grosseto

A hotel room with a large bed, a desk with a computer, a lamp, and a door leading to another room.

Montebelli Agriturismo & Country Hotel

A swimming pool with a waterfall feature, large windows, and a lounge chair.

Conti di San Bonifacio Wine Resort

A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

Find out more about Castiglione della Pescaia

Everything you need to know about Castiglione della Pescaia vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglione della Pescaia vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglione della Pescaia vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castiglione della Pescaia vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglione della Pescaia. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castiglione della Pescaia in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $45 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castiglione della Pescaia rentals

At Expedia, we put the best Castiglione della Pescaia vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castiglione della Pescaia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglione della Pescaia vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglione della Pescaia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Castiglione della Pescaia?

Yes, we give you a choice of vacation rentals close to popular attractions in Castiglione della Pescaia, or you can go with a secluded option if you want a relaxing place to stay. Castiglione della Pescaia is known for its spas and wineries. Make sure you have time to check out the waterfront and golf courses during your trip.

What are some of the best vacation home rentals in Castiglione della Pescaia?

Red Stones by Interhome: Visitors give good reviews to this Castiglione della Pescaia vacation home rental, which is located near the beach and has a private balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven.

How many vacation rentals will I find in Castiglione della Pescaia?

Choose from 165 Expedia vacation rentals in Castiglione della Pescaia for a memorable vacation.

What can I see and do in Castiglione della Pescaia?

Natural Reserve Diaccia Botrona and Spiaggia YCPA are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Red House of Ximenes and Golf Club Punta Ala.

What are vacation rentals like in Castiglione della Pescaia?

Vacation rentals are privately owned properties you can stay in for several days or longer in Castiglione della Pescaia. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family trips.

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