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Holiday rentals with a pool in San Gimignano

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in San Gimignano

  • Total holiday rentals

    Explore 490 holiday rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 12,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    300 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 230 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    480 of San Gimignano holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across San Gimignano rentals

  • 4.7 Average rating

    San Gimignano stays receive an average rating of 4.7 out of 5 from guests

Top-rated rentals with a pool in San Gimignano

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in San Filippo a Ponzano
5.0 out of 5 average rating, 142 reviews

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.

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5.0 out of 5 average rating, 352 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

Top Guest favourite
A private swimming pool is surrounded by vibrant flowers and lush greenery. Multiple lounge chairs are positioned under umbrellas for shade. A seating area is visible in the background, along with a well-maintained pathway and rustic stone walls, enhancing the serene outdoor setting.
Villa in Poggibonsi
4.99 out of 5 average rating, 100 reviews

Villa L'Olivo w/Private pool (Close San Gimignano)

Villa L’Olivo si trova nella campagna Toscana, a circa 10 chilometri da San Gimignano e a pochi minuti dai supermercati ed i vari servizi presenti a Poggibonsi. La nostra Villa è un ottimo punto di partenza per scoprire tutte le bellezze della Toscana, ma è anche un luogo ideale per chi ama concedersi una pausa dalla vita frenetica della città. A Villa L’Olivo, puoi prenotare una cena con chef privato, direttamente in villa, per goderti una cena toscana in tutta tranquillità. Scrivici per info!

Guest favourite
A scenic view captures a hillside vineyard with neatly arranged rows of grapevines. Olive trees dot the landscape, leading to a rustic farmhouse in the foreground, while the skyline of San Gimignano rises against a clear blue sky in the background.
Farm stay in San Gimignano
4.84 out of 5 average rating, 266 reviews

Montegonfoli 5 apartment in farmhouse, 4+2 guests

Comfortable apartment for 4 adults and 2 babies under 12yo, in San Gimignano countryside, in a resort/farmhouse. Here in Montegonfoli you can spend a vacation in absolute relax, in an enchanted natural context, far from the noise but at the same time very close to the most beautiful attractions of the world. First floor with amazing views on San Gimignano and Chianti Hills. No aircon, but every bedroom has a large fan for the few hot nights we are getting in July/August. We usually have 15°C!

Top Guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle
4.98 out of 5 average rating, 218 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.

Top Guest favourite
A sunlit pool area features a spacious salt-water pool with a surrounding deck. Several lounge chairs are arranged with umbrellas, providing shaded seating. A rustic stone building serves as a backdrop, displaying traditional Italian architectural elements and large windows that invite natural light.
Villa in Orentano
4.98 out of 5 average rating, 127 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

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 107 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.

Top Guest favourite
Home in Montaione
4.96 out of 5 average rating, 146 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Top Guest favourite
An aerial view reveals the rustic stone farmhouse surrounded by lush greenery and vineyards. The inviting pool is set within a well-maintained garden, complemented by outdoor seating and barbecue areas, offering a peaceful retreat in the heart of the Tuscan countryside.
Apartment in Gavignano
4.92 out of 5 average rating, 389 reviews

Poggio Massiccioli

Accogliente appartamento per 4 persone arredato in stile toscano e con travi a vista immerso tra le dolci colline della campagna toscana. A disposizione degli ospiti giardino attrezzato,wi-fi gratuita,piscina condivisa attrezzata,forno a legna e barbecue,lavatrice. L'appartamento è stato ricavato da una graziosa casa colonica in pietra del 1800 recentemente ristrutturata secondo la tradizione toscana e suddivisa in tre comodi appartamenti

Top Guest favourite
Villa in Tignano
4.96 out of 5 average rating, 209 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Guest favourite
Two rattan chairs are positioned on a lush green lawn, overlooking rolling hills dotted with olive trees. The tranquil scene features views of a medieval town with distinctive towers, under a partly cloudy sky.
Cottage in San Gimignano
4.88 out of 5 average rating, 139 reviews

Countryside Cottage With View - Le Papere apt

The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.

Top Guest favourite
A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 221 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Popular amenities for San Gimignano rentals with a pool

When is the best time to visit San Gimignano?

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Avg. price$369 NZD$388 NZD$315 NZD$337 NZD$388 NZD$399 NZD$364 NZD$371 NZD$350 NZD$322 NZD$297 NZD$371 NZD
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