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Holiday rentals in Castiglione della Pescaia

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Top-rated holiday rentals in Castiglione della Pescaia

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A rustic kitchen features exposed wooden beams and warm wooden cabinetry. A dining table is set for four, complemented by a well-equipped countertop. Large windows provide natural light, and an inviting entrance leads to the outdoor area. Decorative elements include a chandelier and wall art.
Flat in Pitigliano
4.97 out of 5 average rating, 62 reviews

Energia: "Cantina nel tufo"

La sensazione che si prova entrando nella Cantina nel tufo sarà di forte energia emanata da un luogo in cui antico e moderno sono in armonia. Sarete stupiti dall’intreccio di stanze comunicanti scavate nel tufo in cui la curiosità vi spingerà ad esplorare un ulteriore livello della casa per godere dell’atmosfera raccolta in cui rilassarsi e degustare del vino. Se quello che cercate è un soggiorno immerso nella quiete del borgo, la Cantina è l’ideale per il vostro viaggio nel cuore della Maremma

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 132 reviews

Palazzo Monaci - Piscina nelle crete Senesi

Benvenuti a Palazzo Monaci ! Un' oasi di natura e bellezza unica, nel cuore delle Crete Senesi, in Toscana. Un residence con piscina e vista mozzafiato sulle crete senesi. Perfetta per coppie o famiglie in cerca di una vacanza rilassante. La posizione è perfetta per esplorare le zone limitrofe. Potrete fare escursioni nella campagna toscana, visitare i borghi medievali caratteristici, assaggiare i vini locali prelibati e immergervi nella cultura e nella storia di questa affascinante regione.

Top guest favourite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 107 reviews

Casa del Capitano | 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.

Guest favourite
A scenic view of the villa's exterior is captured, featuring a terracotta roof and lush greenery. The vibrant colors of blooming flowers are visible alongside a panoramic view of the sea and coastal town below, enhancing the natural beauty of the surroundings.
Holiday home in Castiglione della Pescaia
4.8 out of 5 average rating, 20 reviews

Villa panoramica con terrazzo vista mare

A soli 8 minuti a piedi dal mare, questa villa di 150mq immersa nel verde, situata al primo, offre una vista mozzafiato sul mare e sulla spiaggia di Castiglione della Pescaia. Luminosa e spaziosa, dispone di 4 camere da letto, 3 bagni (2 con doccia), soggiorno, cucina attrezzata e lavatrice. Il punto forte è la terrazza panoramica e il solaio vista mare, perfetti per rilassarsi al tramonto. Con Wi-Fi gratuito e aria condizionata, è l’ideale per chi cerca natura, comfort e relax in Maremma.

Guest favourite
A scenic view features a tranquil landscape with rolling hills in the distance. Tall trees frame the image, providing shade to a stone patio. The outdoor area includes comfortable seating, inviting guests to relax while enjoying the surrounding natural beauty.
Home in Castiglione della Pescaia
5 out of 5 average rating, 19 reviews

Casa Vista Mare e Maremma

Benvenuti nella vostra oasi di pace a Castiglione della Pescaia! Situata in una tranquilla zona residenziale, la nostra casa offre una magnifica vista sulla Maremma e si trova a soli 15 min a piedi dal centro storico ed a 5 min di macchina dalle splendide spiagge. Godetevi il perfetto equilibrio tra relax nella natura e avventure balneari, con la comodità di avere tutte le attrazioni del paese a portata di mano. Il vostro rifugio ideale per scoprire le meraviglie della Toscana vi aspetta.

Superhost
A comfortable living area features high wooden beams and large windows allowing natural light. A dining table with seating for four, surrounded by flowers, is seen near a cozy seating arrangement with a lamp and artwork adorning the walls.
Home in Castiglione della Pescaia
4.65 out of 5 average rating, 95 reviews

Lovely seasidehouse with new air condition !

Charming house with new air conditioning in the heart of Maremma on the Tuscan coast in Castiglione della Pescaia with free public parking 1-minute walk from the house. Experience the magic of an ancient medieval village away from the chaotic modern life! Choose a different beach every day (walk a few minutes downtown or drive along the coast - you'll have loads of different beaches to explore, both private and public). To get around: walk or rent a bike or drive a few minutes in Maremma.

Guest favourite
An open kitchen and dining area feature a wooden table surrounded by four chairs. Natural light enters through a window, illuminating the space. A kitchenette with wooden cabinets is present, and a staircase leads to an upper level. Decorative artwork is displayed on the walls.
Flat in Castiglione della Pescaia
4.88 out of 5 average rating, 82 reviews

Appartamento da Iris

Appartamento alle porte del centro e degli stabilimenti balneari di Castiglione della Pescaia. A 15 minuti a piedi dalla prima spiaggia, 5 minuti in bicicletta! A pochi metri dai maggiori supermercati e dal piccolo centro commerciale con pescheria, farmacia, lavanderia e beni di prima necessitá. Offre anche un’ area verde (condominiale) e vista sulle colline. É tutto facilmente raggiungibile a piedi, in bicicletta ( GRATUITE su richiesta ) e macchina, con parcheggio gratuito in loco.

Top guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment in San Gimignano
5 out of 5 average rating, 51 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Guest favourite
A well-lit kitchen area showcases modern cabinetry and appliances, including a stove and oven. A dining table with four chairs is positioned nearby, set with plates and drinks. A beige sofa with blue accent pillows adds comfort to the open living space.
Flat in Castiglione della Pescaia
4.83 out of 5 average rating, 99 reviews

Appartamento sul Corso di Castiglione 2

Luminoso appartamento sulla via principale di Castiglione, piazza della Repubblica 28, davanti al ristorante Casty, a 200 mt dal mare. È composto da camera da letto matrimoniale, bagno con lavatrice, salone con angolo cottura e divano letto matrimoniale. Finemente ristrutturato nel 2019 ed è dotato di infissi insonorizzati ed aria condizionata. Si trova al secondo piano senza ascensore. È esclusa la city tax di 1,2 euro per notte per persona.

Guest favourite
A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.
Cottage in Vetulonia
4.96 out of 5 average rating, 130 reviews

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.

Guest favourite
A charming stone cottage is depicted, featuring a dark roof and a welcoming entrance. Vibrant purple flowers in the foreground provide a splash of color against the gravel pathway, while warm sunlight casts a gentle glow, highlighting the serene surroundings.
Flat in Castiglione della Pescaia
4.95 out of 5 average rating, 131 reviews

Casetta Venere relax Toscano a 3 Km dal mare

Casetta Venere: Mare, natura e Pet-Friendly. A soli 3 km dal mare cristallino di Castiglione della Pescaia, Casetta Venere è un piccolo gioiello toscano tra ulivi, perfetto per coppie, famiglie e viaggiatori con animali. La casa offre spazi curati, un bel giardino privato e un’atmosfera intima e accogliente. Ti aspettiamo per un soggiorno lento, autentico e pieno di bellezza in mezzo alla natura.

Superhost
The living area features a blend of exposed wooden beams and a rustic brick arch. A comfortable sofa is set against a stone wall, and a small bookshelf displays a variety of books. Light-colored tiles create a spacious feel, enhancing the room's inviting ambiance.
Apartment in Castiglione della Pescaia
4.79 out of 5 average rating, 39 reviews

Incantevole loft immerso nel borgo medievale

Charming apartment located in a 17th century building in the enchanting medieval village of Castiglione, a historic area overlooking the sea and protected by the ancient Aragonese walls. Living area characterized by an ancient brick arch and the combination of old and modern, where wood and stone dominate. Located just 600m (10min walk) from the beach and 100m from free parking lot.

Popular amenities for Castiglione della Pescaia holiday rentals

When is the best time to visit Castiglione della Pescaia?

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Avg. price$165 SGD$172 SGD$163 SGD$154 SGD$149 SGD$178 SGD$226 SGD$240 SGD$165 SGD$157 SGD$159 SGD$165 SGD
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Frequently Asked Questions

  • What are the best places to stay in Castiglione della Pescaia?

    Castiglione della Pescaia has a variety of welcoming stays, from beachfront apartments to cozy homes nestled near the historic center. Many travelers choose accommodations around the marina, pine forests, or countryside for relaxing views and local character.

  • What are the best things to do in Castiglione della Pescaia with kids?

    Families often explore sandy beaches with gentle waves, wander the medieval town walls, or visit nature reserves where kids can spot wildlife. Around town, you will find local gelato shops and playful seaside promenades.

  • What are some of the best things to do in Castiglione della Pescaia?

    You can explore the historic Castello Aragonese, relax on popular beaches, or stroll scenic promenades. The nature reserve nearby frequently suggests birdwatching, while local markets showcase Tuscan flavors.

  • How is the weather in Castiglione della Pescaia?

    Castiglione della Pescaia has mild winters around 37–56°F (3–13°C) with occasional rain. Summers are warm and dry, reaching up to 89°F (32°C); lightweight layers and sun protection are helpful during the warmer months.

  • What are the best places to visit in Castiglione della Pescaia?

    Visitors frequently suggest the historic center, Castello Aragonese, and the scenic marina. The Diaccia Botrona Nature Reserve is known for walks and wildlife observation.

  • What are some hiking trails in Castiglione della Pescaia?

    You can explore trails winding through pine forests, coastal dunes, and the Diaccia Botrona Nature Reserve. Some paths lead to hilltop views, rural landscapes, and birdwatching spots.

  • What are some family activities we can do in Castiglione della Pescaia?

    Spend time on gentle beaches, ride bikes along seaside paths, or visit interactive local museums. Families also enjoy boat excursions and nature walks in nearby reserves.

  • What are some of the best day trip ideas from Castiglione della Pescaia?

    Explore neighboring medieval towns, coastal villages, or nearby Tuscan countryside with vineyards and olive groves. Regional parks and nature reserves around the area are frequently suggested for outdoor excursions.

  • Are there any pet friendly accommodations available in Castiglione della Pescaia?

    Many accommodations in Castiglione della Pescaia welcome pets, especially homes near beaches or green spaces. Properties around the pine forest or marina often provide outdoor areas for companion animals.

  • What are some local tips for visiting Castiglione della Pescaia?

    Consider exploring less crowded beaches early in the day and sampling fresh seafood at family-run trattorias. Locals often enjoy sunset walks along the promenade and recommend comfortable shoes for cobblestone streets.

  • What is Castiglione della Pescaia known for?

    Castiglione della Pescaia is known for its sandy beaches, historic castle, and vibrant fishing traditions. Its medieval town center and surrounding nature are often highlighted by visitors.

  • What are the best hidden gems to explore in Castiglione della Pescaia?

    Discover quiet pine forest trails, small local art galleries, and traditional countryside trattorias. Less crowded areas of the Diaccia Botrona Nature Reserve often provide peaceful nature experiences.

  • What are the best foods to try in Castiglione della Pescaia?

    Sample freshly caught seafood such as grilled fish and local shellfish, alongside regional Tuscan dishes like wild boar stew and panzanella. Handmade gelato is a favorite treat for many visitors.

  • What should I bring for a trip to Castiglione della Pescaia?

    Pack lightweight, breathable clothing for the warm months, and a jacket for cooler evenings. Sun protection, swimwear, and comfortable walking shoes are useful for exploring beaches and the historic center.

  • What is the nightlife in Castiglione della Pescaia like?

    Castiglione della Pescaia has easygoing nightlife, with beachfront bars, relaxed pubs, and trattorias. In summer, many visitors gather along the marina and promenade for evening drinks and live music.

  • What are the most popular events or festivals in Castiglione della Pescaia?

    Seasonal celebrations often feature local seafood, music, and historical reenactments centered around the medieval castle. In summer, beach festivals and cultural fairs are frequently suggested for experiencing community spirit.

  • Are there family friendly vacation rentals in Castiglione della Pescaia?

    Castiglione della Pescaia has many family-friendly rentals, from spacious apartments near the beach to homes close to parks and promenades. These stays typically provide amenities for children and convenient access to outdoor activities.

  • When is the best time to visit Castiglione della Pescaia?

    Late spring and summer months are often recommended for pleasant beach days and outdoor activities. If you prefer fewer crowds and milder temperatures, early autumn brings comfortable weather and vibrant local culture.

Quick stats about holiday rentals in Castiglione della Pescaia

  • Total holiday rentals

    Explore 440 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 6,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 230 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    280 of Castiglione della Pescaia holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castiglione della Pescaia rentals

  • 4.7 Average rating

    Castiglione della Pescaia stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Castiglione della Pescaia