
Family-friendly vacation rentals in Siena
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Siena

Total vacation rentals
Explore 570 vacation rentals in Siena

Nightly prices starting at
Siena vacation rentals start at G$4,183 GYD per night before taxes and fees

Verified guest reviews
Over 29,640 verified reviews to help you choose

Pet-friendly vacation rentals
Find 200 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
550 of Siena vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Siena rentals

4.8 Average rating
Siena stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated family-friendly rentals in Siena
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
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Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!
FamilyKitchenBackyard

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.
KitchenIndoor spacesCleanliness

Apartment in Tuscan farm house.
Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.
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Villa di Geggiano - Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.
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Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
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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.
Indoor spacesFamilyGetting around

Luxury frescoed apartment in the historical center
The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.
FamilyIndoor spacesParking

Claudia's House in Piazza del Campo
"The terrace overlooking Piazza del Campo" An elegant period residence, in a 13th-century building, directly overlooking Piazza del Campo, where you will be welcomed by 3 bedrooms with 5 beds, a bathroom with shower, a large living room, a kitchen and a very large living room with fully frescoed ceilings. Our guests will be welcomed in a wonderful and quiet apartment where they can enjoy the beautiful view directly on Piazza del Campo
KitchenIndoor spacesWalkability

Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
Indoor spacesKitchenCleanliness

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.
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La Pieve - the house next to the church
To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?
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Popular amenities for Siena family-friendly rentals
Family-friendly home rentals with a hot tub

"Red Rose" apartment with view of Siena.
FamilyIndoor spacesNearby

Palazzo del Taja - in the center with whirlpool
KitchenIndoor spacesAccuracy

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
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Amazing Tuscany Villa, FREE parking
FamilyKitchenBathroom

Casa Dolce Toscana | Panoramic Suite with a View
KitchenIndoor spacesAir conditioning

Farmhouse in Chianti with Swimming Pool
FamilyIndoor spacesGrill

Agriturismo La Villa - L'Olivo, Pool & Hot Tub
KitchenIndoor spacesQuiet

Charming Tuscan Villa with View forFamily&Friends
Indoor spacesKitchenLaundry
Family- and pet-friendly home rentals

The Door Next Door 2.0
FamilyIndoor spacesView

•Il Chiostro• A gem in the heart of Siena
Indoor spacesFamilySolo travel

[NEW] Modern Central Studio with parking space
KitchenFamilySleep quality

Tuscan cottage with an heavenly view
Indoor spacesKitchenLong stay

Poggio Bicchieri Holiday Farm - Memoria apartment
FamilyKitchenWifi

Vintage apartment 400m PalioPiazza del Campo Siena
Indoor spacesKitchenDecor

Pink like the sunset sky
Indoor spacesFamilyOutdoor spaces

A BALCONY ON THE PIAZZA OF THE PALIO
Indoor spacesFamilyAccuracy
Family-friendly home rentals with a pool

Private Chianti Cottage, Garden & Vineyard Views
FamilyKitchenGrill

Podere Casalino - Il Gatto
FamilyIndoor spacesView

Relaxation and charm in the Chianti hills
KitchenFamilyWalkability

Stone House with Exclusive Pool Codilungo in Chianti
FamilyIndoor spacesSleep quality

Castel Brunello - 2 doublebed rooms + terrace
Indoor spacesKitchenWalkability

Podere Vergianoni nestled in Chianti with a pool
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la Balza
Indoor spacesKitchenView

Siena - apartment in the countryside near Siena
FamilyIndoor spacesPool
When is the best time to visit Siena?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,376 GYD | G$27,192 GYD | G$33,049 GYD | G$34,304 GYD | G$37,023 GYD | G$37,232 GYD | G$35,977 GYD | G$36,186 GYD | G$36,186 GYD | G$35,141 GYD | G$30,330 GYD | G$33,258 GYD |
| Avg. temp | 5°C | 6°C | 9°C | 12°C | 16°C | 21°C | 23°C | 24°C | 19°C | 14°C | 9°C | 5°C |
Destinations to explore
- Cottage rentals Siena
- Rentals with breakfast Siena
- Boutique hotels Siena
- Vacation home rentals Siena
- Serviced apartment rentals Siena
- Pet-friendly rentals Siena
- Rentals with pools Siena
- Bed and breakfasts Siena
- House rentals Siena
- Villa rentals Siena
- Condo rentals Siena
- Apartment rentals Siena
- Rentals with a hot tub Siena
- Hotel rooms Siena
- Family-friendly rentals Siena
- Family-friendly rentals Tuscany
- Family-friendly rentals Italy
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Parco Regionale Della Maremma
- Stazione Santa Maria Novella
- Spiagge Bianche
- Mercato Centrale
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Gulf of Baratti
- Fortezza da Basso
- Parco delle Cascine
- Piazza della Repubblica
- Del Chianti
- Piazzale Michelangelo
- Piazza della Signoria
- Palazzo Vecchio
- Pitti Palace
- Boboli's Garden
- Things to do Siena
- Art and culture Siena
- Nature and outdoors Siena
- Tours Siena
- Sightseeing Siena
- Food tours Siena
- Food and drink Siena
- Cultural tours Siena
- Tastings Siena
- Cooking Siena
- Things to do Siena
- Sightseeing Siena
- Art workshops Siena
- Tastings Siena
- Art and culture Siena
- Entertainment Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Nature and outdoors Siena
- Wildlife Siena
- Food and drink Siena
- Cooking Siena
- Tours Siena
- Sports activities Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Nature and outdoors Tuscany
- Cooking Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Entertainment Tuscany
- Workouts Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Food and drink Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Sightseeing Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food and drink Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Art and culture Italy
- Wellness Italy
- Nature and outdoors Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Sports activities Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Sightseeing Italy
- Galleries Italy
- Tours Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy
- Entertainment Italy







