
Condo holiday rentals in Castiglione della Pescaia
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Quick stats about condo 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 $135 NZD per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Castiglione della Pescaia holiday 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
Top-rated condo rentals in Castiglione della Pescaia
Guests agree: These condos are highly rated for location, cleanliness and more.

La Casetta
“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)
LocationFamilyBeach

Infinity Pool in the green agritourism with a view of the woods
Experience the authentic Tuscany between the sea and the countryside! Our Casetta Valmora estate is located 10 km from Follonica and Massa Marittima. The apartment with private patio, Wi-Fi, and air conditioning overlooks the garden with two sun loungers, ideal for couples, families, and friends. Starting in June 2026, the new panoramic infinity pool overlooking the woods will be available for moments of pure relaxation. In the surrounding area, discover medieval villages, Cala Violina, bike routes, golf (15 km away) and local products.
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New two-room apartment within walking distance of the center and the sea
Bright apartment within walking distance of the center and the sea! Beautiful two-room apartment of about 45 square meters, newly renovated, located in the central area of Castiglione della Pescaia. Its central location offers the possibility of having all the services at your fingertips... bars, restaurants, laundry, tobacco, post office, bike rental service, playground, summer events, bathing establishments. The apartment is suitable for both short and long stays, accommodating 2 people. For those seeking comfort and relaxation
LocationSleep qualityIndoor spaces

Loggiato 3 apartment in Tuscany near Siena
The Loggiato 3 apartment for 2 people is located in the Santa Lucia farmhouse (FARMHOUSE DIVIDED INTO 7 APARTMENTS) in the Crete Senesi near Siena and is located on the first floor with a private table in front of the windows of the loggia. Composed of a double bedroom (two single beds joined together), a bathroom and a living room with a functional kitchen. It is equipped with a wood stove. Outdoor space with table and chairs available on the ground floor. AIR CONDITIONING in the room is PAID according to consumption.
FamilyValueWalkability

Pink like the sunset sky
The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!
LocationFamilyParking

The most beautiful apartment in front of the sea
Come see this beautiful and exclusive 5 beds 2 bath seaside. This home features all New recently. Kitchen has Newer Appliances and Cabinets. Spacious light Living Room with 4 windows. Master Suite leads to a private bathroom. Updated Master Bath features Walk-in Shower. All rooms are equipped with TV and air conditioning. High speed WiFi included. City Center, Shopping are close by and easy access by feet or bike. Sailing and Kitesurfing available nearby. Animals and smoking not allowed.
ValueLocationParking

Characteristic old town A. & G.
The independent 3-bed accommodation in the historic center of Grosseto. 100 meters away there is ample free parking outside the Medici walls, (access to unauthorized cars is strictly prohibited inside the walls). Near the accommodation there are a minimarket, pharmacy, 800 meters from the train station, bus to the sea and shuttle to the station. Starting point for: sea 14 km, 60 km Saturnia thermal baths, 14 km from the Maremma Natural Park, 50 km Monte Argentario, and Siena 70 km.
ValueFamilyLayout

[9 minutes from Montalcino] Elegant House Mafalda
Comfortable apartment located in the heart of Orcia valley (val d’Orcia); strategic location for visiting the sought-after medieval villages of Montalcino, Castiglione d’Orcia, Pienza, Montepulciano and San Quirico d’Orcia. In addition, Torrenieri (Montalcino) has always been considered an excellent starting point for various trekking itineraries. The balcony in one of the suites overlooks the splendid surrounding Sienese hills!! Finally, there is free parking near the house.
FamilyValueAmenities

Sea House
The apartment is on the first floor in a small condominium. The area is also quiet in the middle of summer because it is far from the main street and the center, which can still be reached on foot. In the house you will find a working living kitchen, with washing machine and dishwasher, and a comfortable room also to invite friends to dinner. Living and sleeping areas are separated by a sliding door so everyone can have some privacy.
FamilyValueAmenities

Elegant 3-Room Apartment in Maremma
Discover a slice of paradise in Maremma with the elegant Ansedonia apartment in Grosseto. In the heart of the historic center and just steps from golden beaches, every corner radiates relaxation and harmony: bright open-plan living with modern kitchen and island, warm parquet floors, and refined furnishings. Mornings awaken with light and serenity, evenings wrap you in comfort and unforgettable atmospheres. Your dream retreat awaits.
ValueFamilyCheckout

La Casetta di Brunello, very panoramic with terrace
STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.
FamilyLocationLaundry

Cola de Ballena - Rustic seaside apartment
Recently renovated rustic property in the countryside of Pian di Rocca. Apartment consisting of a living-dining room and a double bedroom (sleeps 2 + 2 double sofa bed). Nestled in two hectares of exclusive greenery in the Tuscan countryside, with a large outdoor courtyard, relaxation area, and barbecue. All this is a short walk from the sea at Rocchette-Roccamare, which can be reached in a few minutes by bike. Pet friendly
FamilyLocationBeach
Popular amenities for Castiglione della Pescaia condo rentals
Weekly condo rentals

Surrounded by pine forest, 300 meters from the sea
FamilyValueAir conditioning

Spacious Flat just 15 Minutes from the Sea
FamilyLocationSleep quality

Verdoliva farmhouse, “Moraiolo” apartment
LocationValueComfort

Sunshine House
ValueLocationQuiet

Babe and Madde's house, air-conditioned environment
ValueLocationParking

Stellamarina apartment in the center of Piombino
LocationFamilyWalkability

[Walking distance to the beach] Amazing sea view
FamilyLocationBeach

Luxury Penthouse with a View of Piazza del Campo
FamilyValueCleanliness
Pet-friendly condo rentals

Palazzo del Taja - in the center with whirlpool
FamilyLocationSleep quality

Casale Elbano "on the waterfront"
FamilyLocationParks

[NEW] Modern Central Studio with parking space
LocationValueAmenities

Vintage apartment 400m from PalioPiazza del Campo Siena
LocationValueKitchen

"Gardenia apartment" Maremma panoramic view
FamilyLocationKitchen

Buriano apartment in an ancient medieval village
LocationWi-FiLong stay

Holiday in an antique farm, The Arches
FamilyLocationAmenities

[Amazing panoramic view] Authentic Tuscan house
LocationFamilyDecor
Condo rentals with a pool

Scenic Stilish Country
FamilyLocationWi-Fi

Relax among the Chianti vineyards - IlVillinoFarmhouse
LocationValueGetting around

[Ninfea] Ancient House in Tuscany
FamilyValueRiver

Charming Residence Castello di Orgiale near Siena
ValueFamilyNearby

Large Apartment in a Villa, swimming pool, Siena
FamilyLocationIndoor spaces

Romantic cottage in Tuscany with pool and garden
LocationGetting aroundBarbecue

Podere Casanovola, Il Sole apartment
ValueLocationSleep quality

Il Giaggiolo – Chianti with a view
FamilyLocationAmenities
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 | $196 NZD | $171 NZD | $214 NZD | $225 NZD | $216 NZD | $235 NZD | $262 NZD | $287 NZD | $198 NZD | $187 NZD | $199 NZD | $218 NZD |
| 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 |
Destinations to explore
- Apartment rentals Castiglione della Pescaia
- House rentals Castiglione della Pescaia
- Beachfront rentals Castiglione della Pescaia
- Villa rentals Castiglione della Pescaia
- Rentals with beach access Castiglione della Pescaia
- Family-friendly rentals Castiglione della Pescaia
- Pet-friendly rentals Castiglione della Pescaia
- Beach house rentals Castiglione della Pescaia
- Waterfront rentals Castiglione della Pescaia
- Condo rentals Grosseto
- Condo rentals Tuscany
- Condo rentals Italy
- Elba
- Giglio Island
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Pianosa
- Spiaggia di Capo Bianco
- Spiaggia di Marina di Campo
- Cascate del Mulino
- Mount Amiata
- CavallinoMatto
- Siena Cathedral
- Vulci
- Palazzo Pubblico
- Terme San Filippo
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Abbey of Monte Oliveto Maggiore





