
House holiday rentals in Castiglione della Pescaia
Find and book unique houses on Airbnb
Top-rated house rentals in Castiglione della Pescaia
Guests agree: these houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

LECCIONE RESIDENCE
Characteristic country house with exposed wooden beams, 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. The 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning and electric oven, espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on-site based on consumption: wood €8 per box, LPG €6 per cubic meter, electricity €0.36 per kW. Wood will be provided for a barbecue and a hot bath in the hot tub for free.

The garden by the sea
A 150-square-meter villa on the Tuscan sea of Prato Ranieri, surrounded by a wonderful and well-kept garden, located in a quiet pedestrian area, with a sandy beach right in front of the gate. Equipped with two parking spaces, it is perfect for families and groups of friends, with a private solarium, a relaxation area and a dining area under a cozy patio. The property is enhanced by a panoramic terrace overlooking the sunset. Within walking distance are beach resorts, ice cream parlors, bars and restaurants.

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.

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.

Villa Simonetta, Poggio le Trincee, Castiglione
Welcome to Villa Simonetta, recently renovated, located in Castiglione della Pescaia, just 7 minutes from the sea and the historic center. It has a modern kitchen, a living area with a sofa bed and a panoramic terrace, 2 double bedrooms with a smart TV and 2 private bathrooms. Outside, equipped terraces, garden, barbecue and independent annex. Equipped with air conditioning, video-monitored parking and a cellar-laundry. Strategic location and breathtaking views of the Tuscan islands.

Design loft with private SPA in Tuscany
Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

Casa Pancole
Beautiful stone house completely and tastefully renovated, surrounded by nature, ideal for privacy, close to places of interest such as Grosseto, Terme di Saturnia, Alberese, Parco dell'Uccellina, Marina di Grosseto (in the cold periods there is a pellet stove that heats the rooms, the pellet is an additional cost to be requested, thank you) tourist tax to be paid directly on site

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.
Popular amenities for house rentals in Castiglione della Pescaia
House rentals with a pool

S.Ilaria - Private pool Villa with 2 bedrooms

Podere Scorno country house with swimming pool

Podere Cavone / Villa Oliva

[Little Escape] 4 Beds + Private Panoramic Pool

Explore Chianti from a Charming Stone House

Country House in the Crete Senesi

Collina Power

Ancient stone house in Chianti
Weekly house rentals

Villa with Pool, Jacuzzi, Sauna near towncentre

Country house short distance from the sea

Monte Regio

Capezzuolo 33

Sensational semi-detached villa - Astonishing view

3 bedrooms, near the pool – Fonte di Sotto

Country chic house in a village,private pool,wiFi

Fazenda da Ido ( Cosy and Renovated Studio)
Private house rentals

“Il Glicine” [Nature, Stars, Relaxation and Pool]

Family Forest - Pool in the Crete Senesi

Frontemare house with exclusive sea access

City Center Palazzo: 4 King BR 6 Bath and Garage

Stunning loft in Montalcino.

La Casa al Sole

Antico Podere trio with pool FOLLONICA

Domus Antiqua
When is the best time to visit Castiglione della Pescaia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $225 SGD | $200 SGD | $192 SGD | $189 SGD | $187 SGD | $187 SGD | $223 SGD | $269 SGD | $192 SGD | $194 SGD | $192 SGD | $253 SGD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about house rentals in Castiglione della Pescaia

Total holiday rentals
Explore 70 holiday rentals in Castiglione della Pescaia

Nightly prices starting at
Castiglione della Pescaia holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 930 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Castiglione della Pescaia holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castiglione della Pescaia rentals

4.6 Average rating
Castiglione della Pescaia stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Beachfront rentals Castiglione della Pescaia
- Rentals with a firepit Castiglione della Pescaia
- Rentals with a washing machine and dryer Castiglione della Pescaia
- Smoking-friendly rentals Castiglione della Pescaia
- Apartment rentals Castiglione della Pescaia
- Rentals with outdoor seating Castiglione della Pescaia
- Beach house rentals Castiglione della Pescaia
- Villa rentals Castiglione della Pescaia
- Flat rentals Castiglione della Pescaia
- Rentals with a patio Castiglione della Pescaia
- Rentals with beach access Castiglione della Pescaia
- Rentals with a fireplace Castiglione della Pescaia
- Waterfront rentals Castiglione della Pescaia
- Pet-friendly rentals Castiglione della Pescaia
- Family-friendly rentals Castiglione della Pescaia
- House rentals Grosseto
- House rentals Tuscany
- House rentals Italy
- Elba
- Giglio Island
- Giannutri
- Cala Violina
- Feniglia
- Spiaggia Di Sansone
- Spiagge Bianche
- Spiaggia Di Barbarossa
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Le Cannelle
- Spiaggia di Marina di Campo
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Pianosa
- Palazzo Pubblico
- CavallinoMatto
- Terme San Filippo
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Monte Oliveto Maggiore





