
Holiday rentals with a pool in Guardistallo
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Guardistallo

Total holiday rentals
Explore 130 holiday rentals in Guardistallo

Nightly prices starting at
Guardistallo holiday rentals start at €52 per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
110 of Guardistallo holiday rentals include wifi 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
Top-rated rentals with a pool in Guardistallo
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Infinity pool in Chianti 1
Our house is a part of a stone farmhouse completely independent from the rest of the adjacent property. Arranged on three floors, on the ground floor there is a large entrance hall, a large living room with fireplace, a bedroom with 1 double bed and a bathroom with window. On the first floor there are two bedrooms (2 +2 beds) with a bathroom with window. In the basement, at garden level, there is the kitchen and the dining room. From the kitchen you access the outside where you will find an area for outdoor dining with a large dining table under a pergola. You then go down towards the garden with barbecue area.
5.0 out of 5 average rating, 142 reviews
In the Tuscan countryside, Podere I Luoghi with swimming pool Ap1
In an old 19th-century farm, a lovely apartment surrounded by the greenery of the Tuscan countryside, on a hill with a beautiful sea view. It has 3 double bedrooms with a private bathroom, an equipped kitchen, a dining room and an outdoor area ideal for outdoor dining and relaxation. Seasonal swimming pool from June to September. Just 12 km from the sea, perfect for visiting villages such as Bolgheri, Castagneto Carducci, Montescudaio and Volterra, among hills, vineyards and authentic flavors.
4.85 out of 5 average rating, 13 reviews
Open space surrounded by nature
Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring
4.96 out of 5 average rating, 137 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic 17th-century property located in the beautiful Chianti hills of Tuscany, with the option of arranging a private shuttle and local experiences directly with our family. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
5.0 out of 5 average rating, 352 reviews
Astonishing beachfront villa with private garden
In the aristocratic and secluded Tombolino estate Villa La loggia is separated from the others by a private garden which leads through an alley of elm trees and oleanders to the house. As its name says a spectacular veranda offers a large outside space. The floor is made of a patterned, in laid black marble square tiles set in bleached wooden slabs and the white wooden beams of the roof give a very outstanding colonial flavour, with wicker furnishing and large comfortable armchairs.
5.0 out of 5 average rating, 7 reviews
Villa Gourmet Food, Pizza, Chef, Pool and Nature
Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services
4.98 out of 5 average rating, 127 reviews
Stone House with Exclusive Pool Codilungo in Chianti
Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.
4.98 out of 5 average rating, 218 reviews
Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.
4.99 out of 5 average rating, 138 reviews
Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.
4.98 out of 5 average rating, 107 reviews
Ai Massi Annamaria Farmhouse (three-room apartment 57sqm)
Apartment (three-room apartment of 57 sqm, sleeps 4) with sea view, located on the SECOND FLOOR of the farmhouse, entrance on the west side. It has a kitchen (equipped with a fridge, dishwasher, induction stove, microwave, kettle, toaster, immersion blender and Moka coffee maker), a living room (TV and Wi-Fi), two bedrooms with double bed and bathroom. The property has an eco-friendly swimming pool and overlooks the Etruscan Coast countryside.
5.0 out of 5 average rating, 15 reviews
Frontemare house with exclusive sea access
Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.
4.95 out of 5 average rating, 111 reviews
Cercis - La Palmierina
The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.
4.96 out of 5 average rating, 146 reviewsPopular amenities for Guardistallo rentals with a pool
House rentals with a pool

Collina Power
4.93 out of 5 average rating, 203 reviews
Borgo Ripostena – No. 8 Casa Vecchia
4.95 out of 5 average rating, 201 reviews
Ancient Barn in Chianti with Pool
4.89 out of 5 average rating, 125 reviews
I Limoni Apartment in Tuscany
4.85 out of 5 average rating, 151 reviews
Private villa/swimming pool in Tuscany
4.93 out of 5 average rating, 164 reviews
SuiteLouise.pool, Hot Tub,homeGym & private Garden
4.91 out of 5 average rating, 128 reviews
Charming Tuscan Villa with pool
5.0 out of 5 average rating, 22 reviews
The Cottage to relax and enjoy
5.0 out of 5 average rating, 22 reviewsApartment rentals with a pool

La Casetta
4.93 out of 5 average rating, 197 reviews
Casa Luna-Splendida overlooking the pool and Tuscan nature
4.97 out of 5 average rating, 151 reviews
Bel Canto Lari, exclusive, rural, Tuscan retreat
4.97 out of 5 average rating, 105 reviews
Charming Tuscan home with pool, garden & Air-Con
4.88 out of 5 average rating, 100 reviews
Adalberto Apartment inside the Manor of Fulignano
4.95 out of 5 average rating, 152 reviews
Scenic Stilish Country
4.88 out of 5 average rating, 136 reviews
Apartments Le Palme
4.92 out of 5 average rating, 102 reviews
'Toscana Amore Mio', stunning views, 18 min to Volterra
4.81 out of 5 average rating, 21 reviewsHome rentals with a private pool

TREEhouse / casaBARTHEL
4.88 out of 5 average rating, 821 reviews
Casa Luigi Suite with exclusive pool
4.95 out of 5 average rating, 122 reviews
Luxe Estate nr Florence. Vineyard, Pool, Privacy
4.97 out of 5 average rating, 73 reviewsHistoric villa x8 with exclusive pool
4.87 out of 5 average rating, 46 reviews
Villa Fonteintanata Ground floor
4.8 out of 5 average rating, 75 reviewsWhen is the best time to visit Guardistallo?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €186 | €156 | €139 | €141 | €134 | €138 | €165 | €195 | €135 | €146 | €152 | €186 |
| Avg. temp | 7°C | 8°C | 10°C | 13°C | 17°C | 21°C | 24°C | 24°C | 21°C | 17°C | 12°C | 8°C |
Destinations to explore
- Elba
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Stazione Santa Maria Novella
- Cala Violina
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Spiaggia Di Sansone
- Capraia
- Gorgona
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria





