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Apartment vacation rentals in Montemassi

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Top-rated apartment rentals in Montemassi

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Top guest favorite
Aerial view of the agriturismo Santa Lucia, showcasing well-maintained grounds surrounded by lush greenery and neatly lined cypress trees. A shared swimming pool is visible at the center, complementing the rustic charm of the old farmhouse and the rolling hills in the background.
Apartment in Asciano

Appartamento Loggiato 2 in toscana con piscina

L'appartamento Loggiato 2 per 2 persone si trova nell'agriturismo Santa Lucia (L'AGRITURISMO è DIVISO IN 7 APPARTAMENTI) nelle Crete Senesi vicino Siena ed è un bilocale situato al primo piano con tavolino privato dinanzi alle vetrate del loggiato d'ingresso. Ci sono una camera matrimoniale (due letti singoli uniti per formare un letto matrimoniale), bagno con doccia e soggiorno con cucina funzionale e televisione. L' APPARTAMENTO HA L'ARIA CONDIZIONATA nella camera ( A PAGAMENTO ).

LocationValueLong stay

4.94 out of 5 average rating, 162 reviews
Top guest favorite
A scenic view captures a quaint village nestled in the greenery, with terracotta rooftops visible among the landscape. The paved road leads to parked cars, while the distant rolling hills are dotted with trees, creating a serene backdrop.
Apartment in Montemassi

" DA OSCA " nel cuore della Maremma

L'appartamento " DA OSCA " e' collocato al primo piano ( al piano terra abitano i proprietari) di una palazzina situata ai piedi del celebre Castello di Montemassi. L'appartamento si compone di una cucina attrezzata, un soggiorno ( con divano, caminetto e tavolo da pranzo) , 2 camere matrimoniali, una camera con divano letto matrimoniale, 1 bagno con doccia e vasca e 2 balconi. Il giardino e' a disposizione degli ospiti per colazione, pranzo, cena e relax ( uso di barbecue ).

ValueFamilyLaundry

4.95 out of 5 average rating, 132 reviews
Top guest favorite
A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.
Apartment in Castiglione d'Orcia

Appartamento Mimosa - Poggio al Vento

Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

LocationValueCheck-in

4.99 out of 5 average rating, 112 reviews
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

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.

LocationValueKitchen

4.98 out of 5 average rating, 129 reviews
Top guest favorite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Apartment in Castelnuovo Berardenga

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

LocationValueIndoor spaces

4.94 out of 5 average rating, 188 reviews
Guest favorite
Apartment in Scarlino

Il portico di Leo

Soggiorna in questo alloggio unico e trascorri serate memorabili contemplando l'orizzonte. Respira aria pulita e goditi il relax che ti offre il borgo di Scarlino. Ideale per coppie o piccole famiglie che desiderano un alloggio funzionale e comodo. DAL 1 MAGGIO AL 31 AGOSTO si applica tassa di soggiorno della tariffa di €1,00 a notte/a persona per ogni giorno di permanenza. NON E' INCLUSA nel prezzo finale dell'alloggio la biancheria da letto e da bagno.

ValueFamilyKitchen

4.91 out of 5 average rating, 140 reviews
Top guest favorite
The lounge features elegant walls adorned with intricate frescoes and moldings. A large mirror reflects the refined decor. Two white armchairs and a colorful sofa provide seating, while a coffee table rests on a patterned rug before a decorative fireplace.
Apartment in Siena

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.

ValueFamilyView

4.97 out of 5 average rating, 117 reviews
Guest favorite
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.
Apartment in Castiglione della Pescaia

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.

FamilyValueParks

4.95 out of 5 average rating, 145 reviews
Top guest favorite
The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.
Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.

FamilyLocationHospitality

4.99 out of 5 average rating, 118 reviews
Guest favorite
An outdoor dining area is surrounded by lush greenery and flowering plants, featuring a circular table with four elegant wrought iron chairs. A cozy blanket is draped over one chair, and a scenic view of rolling hills extends in the background under a muted sky.
Apartment in Monteroni d'Arbia

Appartamento "Red Rose" con vista su Siena.

Caggiolo è un podere completamente ristrutturato composto da più appartamenti, ognuno con ingresso indipendente e giardino privato, con vista panoramica su Siena. Situato alle Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

ValueLocationOutdoor spaces

4.94 out of 5 average rating, 288 reviews
Top guest favorite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni

Comfort Apartment tra i vigneti del Chianti

Appartamento al piano superiore della struttura caratterizzato da una vista meravigliosa sulle colline del Chianti, uliveti o sul patio. Ristrutturato mantenendo il fascino delle loro antiche mura ma aggiungendo ogni comfort. Comprende soggiorno, angolo cottura, una camera da letto matrimoniale, un bagno privato con doccia, aria condizionata.

FamilyLocationGetting around

4.93 out of 5 average rating, 455 reviews
Top guest favorite
A balcony provides a scenic view of Piazza del Campo, showcasing the surrounding historic buildings. A small table and chair invite relaxation, while the colorful sunset casts a warm glow over the area, highlighting the lively atmosphere with people enjoying the space below.
Apartment in Siena

A BALCONY ON THE PIAZZA OF THE PALIO

Three windows with balcony overlooking Piazza del Campo that allows access to an exclusive terrace with breathtaking views of the Piazza del Palio and the Palazzo Pubblico. One bedroom, large super-equipped kitchen. Sofa bed available to comfortably accommodate up to 4 people

FamilyValueCleanliness

4.87 out of 5 average rating, 271 reviews

Popular amenities for Montemassi apartment rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Weekly apartment rentals

Guest favorite
A panoramic view of a rustic farmhouse is captured, surrounded by expansive green hills and fields under a bright blue sky. The structure features a traditional tiled roof and is set within a serene countryside landscape, offering a tranquil escape.
Apartment in Castiglione d'Orcia

agriturismo " il poderuccio " bilocale

ValueFamilyBiking

4.93 out of 5 average rating, 121 reviews
Guest favorite
A view from the window showcases mist-covered rolling hills and lush greenery. Trees and a rustic building can be seen in the distance, framed by the natural surroundings. The sky displays a soft blue hue, adding to the serene landscape.
Apartment in Asciano

Farmhouse apartment with pool

LocationValueDecor

4.9 out of 5 average rating, 104 reviews
Top guest favorite
A panoramic view of the surrounding landscape is captured, featuring rolling hills and fertile fields under a clear blue sky. Distant mountains are visible, creating a serene backdrop for the charming rooftop of a nearby building, bordered by lush greenery.
Apartment in Montemassi

Nice apartment with garden and breath-taking view

FamilyLocationGetting around

4.9 out of 5 average rating, 63 reviews
Guest favorite
A freestanding tub is positioned in front of a window framed by rustic stone walls. Light enters from outside, revealing natural greenery and distant architectural elements. The faucet is elegantly designed, adding a modern touch to the serene bathroom setting.
Apartment in Montemassi

divo little boutique home

ValueLocationBreakfast

4.97 out of 5 average rating, 87 reviews
Guest favorite
Apartment in Montemassi

Tenuta di montemassi azzurro apartment 2/3 people

LocationViewPool

5.0 out of 5 average rating, 8 reviews
Top guest favorite
Apartment in Roccatederighi

Domus Olea BnB

ValueLocationCheckout

4.95 out of 5 average rating, 44 reviews
Guest favorite
Apartment in Castiglione della Pescaia

Agriturismo Bandinelli #3 "Palmizia"

FamilyLocationDecor

4.94 out of 5 average rating, 65 reviews
Guest favorite
Apartment in Asciano

Incredible Views & Pool in the Tuscan Hills

LocationValueDecor

4.85 out of 5 average rating, 26 reviews

Private apartment rentals

Top guest favorite
A welcoming entryway features a mural depicting a serene landscape framed by arches. Built-in shelves display decorative items and books. Natural light illuminates the wood flooring, while a small globe and a vase with dried plants add subtle warmth to the space.
Apartment in San Gusmè

Casa Guardiavigna | Chianti Hills Vineyard Retreat

ValueLocationWifi

4.98 out of 5 average rating, 130 reviews
Top guest favorite
An aerial view captures multiple buildings set within lush greenery, featuring a centered infinity pool surrounded by comfortable lounge chairs. Pathways connect the structures, creating a harmonious outdoor space. The landscape is well-maintained, showcasing trees and open areas, enhancing the scenic environment.
Apartment in Campagnatico

Agriturismo Marrucheti 82 App. Ovest

ValueLocationPool

5.0 out of 5 average rating, 30 reviews
Guest favorite
A charming stone facade of a Tuscan house is framed by lush greenery and flowering pots. A small table with chairs invites outdoor seating, while wooden beams support the vine-covered pergola, creating a shaded area. Bright flowers add a touch of color to the rustic setting.
Apartment in Chiusdino

La Pergola: sunny & charming hilltop country house

FamilyLocationDecor

4.95 out of 5 average rating, 93 reviews
Guest favorite
Apartment in Montalcino

Wp Relais Appartamento Argante

FamilyLocationBathroom

5.0 out of 5 average rating, 5 reviews
Guest favorite
The two-story stone building features a warm, rustic design with a large staircase leading to an upper balcony. Multiple windows adorned with wooden shutters are visible, and a lush garden area with greenery is present in the foreground, creating a serene outdoor space.
Apartment in Roccastrada

L'Olivo: Appartamento x 2 - Finestra sulla Maremma

ValueFamilyTV

4.91 out of 5 average rating, 88 reviews
Top guest favorite
A spacious terrace offers stunning views of the surrounding mountains and the charming town below. Potted plants line the edges, while a wooden dining table with matching chairs is positioned for outdoor dining. The soft sunlight enhances the inviting atmosphere of the space.
Apartment in Ravi

Casa Vacanze Enos & Iside

LocationFamilyGetting around

4.95 out of 5 average rating, 37 reviews
Guest favorite
A dining table is set with plates, glasses, and utensils, positioned near expansive glass doors. Natural light fills the space, revealing a view of the private patio and lush greenery beyond. A bowl rests at the center of the table, enhancing the dining experience.
Apartment in San Giovanni d'Asso

Podere Ferranino #Fra Angelico Townhouse

FamilyLocationBathroom

5.0 out of 5 average rating, 8 reviews
Superhost
Apartment in Bossi

Villino Ersilia Music, il fascino del Chianti

LocationFamilyAccuracy

5.0 out of 5 average rating, 4 reviews

Apartment rentals with a hot tub

Guest favorite
A rustic stone building is framed by lush greenery, with a gravel pathway leading to its entrance. Windows are adorned with flower boxes, and archways add architectural interest. The sky features a mix of clouds, hinting at a temperate climate.
Apartment in Montalcino

Appartamento bilocale classic

ValueLocationView

4.84 out of 5 average rating, 109 reviews
Guest favorite
A rectangular swimming pool with a shallow and deep end is surrounded by a stone patio and lush greenery. A villa sits on a hillside in the background, featuring a terrace with windows and shutters. Poolside lights are placed around the pool for evening ambiance.
Apartment in Siena

Villa’Colombaiolo di Marciano',28

FamilyLocationGrill

4.91 out of 5 average rating, 149 reviews
Top guest favorite
The living area features a stylish design with a dark gray sofa and two deep red armchairs. A round glass table sits on a marble floor, enhanced by natural light from the two windows with light curtains. A decorative mirror and elegant light fixtures adorn the walls.
Apartment in Siena

Domus Nannini - L' Arco di Matteotti Spa

ValueFamilyAccuracy

4.98 out of 5 average rating, 107 reviews
Top guest favorite
An inviting entrance features wooden doors framed by rustic stone walls. A small wooden table with two chairs is positioned beside it, adorned with potted flowers. A traditional ceramic jar adds character, enhancing the welcoming atmosphere.
Apartment in Radicondoli

SerenaHouse

FamilyValueComfort

4.96 out of 5 average rating, 50 reviews
Guest favorite
An outdoor dining area is set beneath a pergola adorned with grapevines, offering a scenic view of the surrounding hills and valleys. A table is arranged with dinnerware, surrounded by metal chairs, creating an inviting space for meals while enjoying the landscape.
Apartment in Montalcino

Podere Belsogno

FamilyValueComfort

4.93 out of 5 average rating, 89 reviews
Guest favorite
The kitchen area features rustic wooden ceiling beams and terracotta floor tiles. A dining table with chairs is set for meals, while modern appliances, including an oven and a refrigerator, are visible in the background. Natural light streams through the window, enhancing the inviting space.
Apartment in Castagneto Carducci

Tuscan Farmhouse with Pool & Panoramic View

FamilyLocationWifi

4.97 out of 5 average rating, 29 reviews
Top guest favorite
A well-maintained pool area is surrounded by lush greenery, featuring several sun loungers positioned beside the tranquil water. Umbrellas provide shade, ensuring a comfortable outdoor experience. A rustic wooden fence lines the perimeter, adding a natural element to the inviting setting.
Apartment in Poggio Salvi

Appartamento accogliente per 2

LocationDecorHospitality

5.0 out of 5 average rating, 44 reviews
Guest favorite
A heated hydromassage pool is framed by olive trees, with soft purple lighting reflecting off the water's surface. In the background, a rustic building is visible among tall cypress trees, creating a serene outdoor setting at dusk.
Apartment in Monteroni d'Arbia

San Giovanni in Poggio, apt Crepuscolo Siena, 60mq

LocationValueDecor

4.94 out of 5 average rating, 47 reviews

Destinations to explore