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Apartment vacation rentals in Guardistallo

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Top-rated apartment rentals in Guardistallo

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Guest favorite
A clear, inviting swimming pool is surrounded by sun loungers and umbrellas. Lush hills are visible in the background, featuring a rolling landscape under a bright sky. The pool area provides an open and relaxing space for guests to enjoy the outdoors.
Apartment in Tavarnelle Val di Pesa
4.92 out of 5 average rating, 102 reviews

Romantic Apt in the heart of Chianti (with Tennis)

The apartment Duchessina 5 at Poggio d'Oro is a small one-room ground level unit very cozy and ideal for a couple looking for a casual accommodation located on a hillside in a large villa. 22 sq.m., independent entrance, parking facility just few meters away, stunning views. Living-dining room with kitchen corner (gas stove top with 4 burners, microwave oven) and double bed, bath room with shower, equipped (garden furniture) outdoor paved space, not far from the pool. Airconditioned.-

Superhost
A charming outdoor space features terracotta tiles and rustic stone walls. Lounge chairs are positioned for relaxation, surrounded by greenery and planter boxes filled with flowers. A few small tables complement the area, offering a welcoming spot to enjoy the serene environment.
Apartment in Rosignano Marittimo
4.81 out of 5 average rating, 63 reviews

In touch with nature, M2 Lodging, A/C, Wi-Fi

Questo meraviglioso appartamento per vacanze si trova in una posizione magica a contatto con la natura, vicino a Pomaia (paese a 600 metri), un piccolo borgo medievale collinare a soli 13 km dal mare Tirreno toscano. Originariamente un mulino, l'edificio è stato restaurato e trasformato in 3 confortevoli appartamenti indipendenti. Nel giardino in comune ci sono alcuni alberi da frutto, una vasca idromassaggio e una veranda per rilassarsi, a disposizione degli ospiti (aperta 15/5-30/9).

Top guest favorite
A modern kitchen and dining area feature sleek cabinetry and a spacious dining table. White chairs surround the table, complemented by a vase of flowers. Large windows enhance the room's brightness, while neutral-colored tiles create a clean and inviting atmosphere.
Apartment in Montescudaio
4.93 out of 5 average rating, 165 reviews

Elegant and bright apartment in Montescudaio

The apartment has been recently renovated, very bright and welcoming, the furnishings are modern and practically new. Located in the residential area of Montescudaio, quiet and peaceful from where you can easily reach the most characteristic places of Tuscany: medieval villages, enchanting hills and all the splendid historic cities (Pisa, Florence, Siena...) that make Tuscany such a popular destination. Just 20 minutes to the sea. Your vacation will be unforgettable!

Top guest favorite
A scenic view features a gentle hillside dotted with wildflowers, leading to the ancient Montemassi Castle perched atop. Olive trees are visible in the background, with a sky presenting a soft blend of clouds and blue hues.
Apartment in Montemassi
4.97 out of 5 average rating, 116 reviews

Casa Sabina

The apartment, which provides your own private entrance, has been recently renovated and furnished with care. It is located at the foot of the ancient Castle of Montemassi in a historic square in the characteristic medieval village. With only pedestrian access allowed in this square, you can be assured to have a tranquil and peaceful stay. A 5 minute walk from the apartment, the Castle of Montemass provides visitors with a cultural activity during their stay.

Guest favorite
A living area features a blue sofa accompanied by decorative cushions. A low coffee table sits on a patterned rug, while a bookshelf displays assorted items. Artwork adorns the walls, adding a touch of color to the light-filled space.
Apartment in Cecina
4.94 out of 5 average rating, 100 reviews

The house of light

Bright and airy apartment on two floors, living room with sofa bed, large kitchen and bathroom on the ground floor; on the first floor a double bedroom, a bedroom with two single beds, bathroom with shower. 30 sqm of paved garden where you can have lunch, dinner, enjoy the beautiful sunsets and the silence of the countryside on summer evenings. Private parking space in front of the house for a medium-sized car, otherwise in the private access road

Top guest favorite
An independent building is surrounded by lush greenery, featuring blue shutters and a terracotta patio area. Small tables are set for outdoor seating. The expansive garden includes mature trees and various plants, creating a serene outdoor environment.
Apartment in Palaia
4.96 out of 5 average rating, 124 reviews

Podere Le Murella "Sunset"

A cozy retreat for two, set among the green Tuscan hills. Enjoy a private patio for outdoor dining, large garden, free Wi-Fi, fully equipped kitchen, coffee machine, washing machine, dryer, barbecue area, and linens included. Private parking. Ideal for a romantic escape or relaxing stay near Pisa, Florence, Volterra, and charming villages. A perfect base to explore nature, art, and local life—all year round.

Top guest favorite
A spacious living area features exposed wooden beams and warm, neutral tones. Comfortable seating is arranged around a light coffee table, with decor including a magazine and a small centerpiece. A fully equipped kitchen is visible in the background, complemented by natural light from nearby windows.
Apartment in Peccioli
4.89 out of 5 average rating, 117 reviews

Da Vinci: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment at Peccioli, Tuscany! Enjoy a renovated space, with A/C in the center if a medieval town next to bars, restaurants and shops. Beautifully decorated, with new appliances and furniture, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

Guest favorite
An outdoor dining area is highlighted by a wooden table surrounded by four white chairs. A parasol provides shade above the table, while a lemon tree adds greenery to the space, creating an inviting spot for al fresco meals.
Apartment in Cecina
4.93 out of 5 average rating, 245 reviews

Cozy apartment in Cecina

45 sqm apartment on one floor with a small garden that can be used for outdoor lunches and dinners. It includes: a living room with a sofa bed and kitchen, a bathroom and a bedroom. In the residential area of Cecina, a 10-minute drive to the sea. Parking is free throughout the apartment's street. The apartment is a 15-minute walk from Cecina train station. Bus stop 2 minutes by foot.

Guest favorite
Apartment in Montescudaio
4.92 out of 5 average rating, 79 reviews

The Borgo Suite

Comfortable and charming two-room apartment, newly renovated, located in the heart of the historic center of Montescudaio. The Suite has the use of a large terrace that offers a breathtaking view from the hills to the sea overlooking the islands of the Tuscan archipelago. Strategically located both for enjoying a beach vacation and for relaxing in the tranquility of a medieval village

Guest favorite
A sunlit pool area features a clear, inviting swimming pool surrounded by green lawn. Bright umbrellas and lounge chairs are arranged near the pool, providing shaded seating. Lush greenery and a stone wall create a cozy, secluded atmosphere.
Apartment in Casole D'Elsa
4.94 out of 5 average rating, 111 reviews

Girasoli apartment with pool in farmhouse

Going up 17 steps you will be hosted in an apartment located on the second floor with a separate entrance. Consisting of a kitchen, bathroom with shower and double bedroom with 2 windows overlooking the village of Casole d'Elsa and the swimming pool. Mosquito nets on the windows. Small terrace shared with the Manuela apartment TO BE PAID - ACCOMMODATION TAX €1 per person

Guest favorite
A blooming tree adorned with delicate pink flowers stands prominently against a clear blue sky. Nearby, a small brick monument and rugged greenery complement the scene, offering a glimpse of the surrounding natural setting in the countryside.
Apartment in Sassi Bianchi
4.86 out of 5 average rating, 113 reviews

"The Almond Shelter" in the green of Chianni

Cozy and comfortable refuge immersed in the green of the hills and woods of Tuscany. Our accommodation, a bright and equipped studio with every comfort, is located in the countryside of the municipality of Chianni, a medieval village in the heart of Valdera. Ideal place for a relaxing vacation in the nature and history of our region.

Guest favorite
The spacious kitchen and living area feature a comfortable sectional sofa, a dining table surrounded by five chairs, and modern appliances. Bright pendant lights hang from the ceiling, and textured tile flooring adds warmth to the space. An open staircase is visible in the background.
Apartment in Montescudaio
5 out of 5 average rating, 27 reviews

Residenza Le Mura

Recently restored apartment of medieval origin in the town's historic village. Large kitchen with 55" TV and elegant sofa, 1 double bedroom, 1 bathroom with shower and washing machine. Balcony overlooking the village square. Air conditioning in all rooms. Free internet access with fiber optics

Popular amenities for Guardistallo apartment rentals

When is the best time to visit Guardistallo?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,235 GYDG$25,537 GYDG$31,607 GYDG$23,234 GYDG$25,955 GYDG$23,234 GYDG$26,793 GYDG$28,886 GYDG$23,443 GYDG$27,002 GYDG$29,095 GYDG$40,189 GYD
Avg. temp7°C8°C10°C13°C17°C21°C24°C24°C21°C17°C12°C8°C

Quick stats about apartment rentals in Guardistallo

  • Total vacation rentals

    Explore 130 vacation rentals in Guardistallo

  • Nightly prices starting at

    Guardistallo vacation rentals start at G$6,279 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,410 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Guardistallo vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Guardistallo rentals

  • 4.6 Average rating

    Guardistallo stays receive an average rating of 4.6 out of 5 from guests

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