Vacation rentals with a pool in Castiglioncello

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Top-rated rentals with a pool in Castiglioncello

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

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Guest favorite

Condo in Morrona

4.96 out of 5 average rating, 112 reviews

Casa Luna-Splendida overlooking the pool and Tuscan nature

My husband and I fell in love at first sight with this beautiful place. So we have moved here our whole life. Ideally located on the hill of Morrona,this landscape affords unique views over the hills near Pisa,put us in direct contact with a calm nature and gives us a wonderful spectacle of the fascinating and surprising course of seasons. The location is enhanced by the swimming pool with hydromassage,for those seeking a moment that will remain on their skin and in their hearts for a long time

Nov 5 – 12

G$14,237 GYD per night

Guest favorite

Loft in Rosignano Marittimo

4.94 out of 5 average rating, 96 reviews

Sun Studio: absolute exclusivity

PERFECT FOR SAFE HOLIDAYS. Our little place, Il Cubetto, was inaugurated with the 2020 season. It is particularly distinctive because of its absolute exclusivity: only two studio apartments within our 7000 sqm of garden planted with many fruit trees, with great attention to any detail. Our guests, a maximum of two per studio apartment, have the use of a salt-water infinity swimming pool overlooking the valley. Depending on the car they drive, they can park next to the cottage or beside the road.

Feb 4 – 11

G$46,148 GYD per night

Superhost

Home in Lucca

4.84 out of 5 average rating, 149 reviews

SunnySide, house with pool on Lucca hills

The perfect place to relax and take a break. An apartment in an ancient 1863 residence nestled in the Tuscan landscape; is completely restored, tastefully decorated, and equipped with a large swimming pool. About 5" from the historic city center of Lucca and only 25" from the sea. Come and live here, discover the private woodland of the residence, enjoy the large pool, and try a lifestyle in complete harmony with nature without sacrificing any comfort. Free parking space, WIFI, and Prime Video.

Feb 3 – 10

G$26,420 GYD per night

Superhost

Villa in Capannori

4.92 out of 5 average rating, 12 reviews

Luxury Tuscany Villa on the hill with private pool

Luxury villa with private swimming pool, accompanied by a large fenced garden, located on the hills with a beautiful view of the splendid city of Lucca. Equipped with a furnished gazebo, barbecue, ping pong table, wifi internet, air conditioning. 8 km from the city of Lucca 31 km from the sea 70 km from Florence 25 km from the city of Pisa and the airport. Ideal for families and pets. The rate is NOT included : the electricity, the gas, the wood for the fireplace to be paid on consumption.

Feb 14 – 21

G$28,746 GYD per night

Guest favorite

Vacation home in Riparbella

4.96 out of 5 average rating, 27 reviews

Tuscan countryside & pool - 20 min from the beach

2 bedroom flat in a countryside house, immersed in nature. Infinity pool of 12 mt by 4 mt, open from April to October, to be shared only with another smaller flat, which is used at times by the owner of the property (no more than 2/3 people). 20 minutes from the beach of Cecina or the wine-famous town of Bolgheri. Great wineries are close by (Caiarossa -5 min, La Regola -15 min drive). 1km of unpaved road to the house, please drive on it slow the last 25 meters, accessible for all kind of cars.

Oct 21 – 28

G$124,616 GYD per night

Guest favorite

Villa in Monsummano Terme

4.98 out of 5 average rating, 106 reviews

Le Maggioline : your panoramic country house

Peaceful setting surrounded by olive groves but still conveniently located for sightseeing The house is a tastefully renovated old Italian home, with modern fixtures, and 4 ensuite bedrooms with panoramic views A large terrace with a veranda for eating out, a barbecue and an outdoor panoramic pool renovated in 2023 Open from April to October Some guest say “Our favorite thing about the home was sitting out at the long table every evening, sipping local wines and enjoying majestic sunsets"

Dec 24 – 31

G$184,397 GYD per night

Guest favorite

Farm stay in Terricciola

5.0 out of 5 average rating, 21 reviews

Tuscany | Farmhouse with pool and restaurant

Agriturismo il Selvino is a Tuscan farmhouse with swimming pool and restaurant, located in Terricciola, between Pisa and Volterra, and about 35 minutes from the most beautiful beaches in Tuscany and numerous places rich in history and culture. The estate has a total of 10 apartments, at guests' disposal a shared swimming pool with a large flower garden surrounded by beautiful olive trees. Each apartment has its own outdoor space with private table, chairs and umbrella.

Mar 20 – 27

G$25,443 GYD per night

Guest favorite

Apartment in Santa luce

4.87 out of 5 average rating, 30 reviews

Leonardo apt. in the wild Tuscany hills~ Le Fraine

Concediti una vacanza immerso nella natura toscana, tra vigne e oliveti. L’appartamento Leonardo, si trova al primo piano del casale Dotato di camera da letto con letto matrimoniale, bagno con doccia e salotto con cucina e divano letto. Dalla finestra potrai scorgere la vecchia oliveta e i primi raggi del sole ti sveglieranno dolcemente per cominciare al meglio la giornata. Per i tuoi momenti di relax all’aperto, ti abbiamo dedicato uno spazio privato in giardino.

Oct 20 – 27

G$28,218 GYD per night

Guest favorite

Cottage in Chianni

4.98 out of 5 average rating, 118 reviews

La Pietruzza - The Private Chalet with a Soul -

Detached country cottage (in exclusive use) in stone and glass dating from XVIII century ideal for 4 persons. Wide wooden veranda. EXCLUSIVE POOL with SALTED WATER ( 33 ft x 16.40 ft ) depth of the pool from 4.6 ft to 7.9 ft. The Chalet is surrounded by 6000 meters of land with fruit trees, olive trees, acacias. We care about nature and do not use herbicides. There is no gas at home because it is all electric with photovoltaic system. (CIR O5OO12LTNOOO3)

Mar 18 – 25

G$38,956 GYD per night

Superhost

Farm stay in Monterotondo Marittimo

4.83 out of 5 average rating, 169 reviews

Studio apt. in Estate with Craft Brewery

Our organic farm is surrounded by 400 hectares of fields and woods, which gently slope down towards the quiet Val di Cornia. The ancient farmhouses and terrain represent the traditional Maremma Toscana. Here, we offer an unforgettable experience of culture, nature, food, adventure and relaxation. The estate features or farm-to-table restaurant, two panoramic swimming pools, farm animals, signed paths and agricultural craft brewery.

Aug 25 – Sep 1

G$41,627 GYD per night

Superhost

Condo in Rosignano Solvay-Castiglioncello

4.88 out of 5 average rating, 16 reviews

100mt from sea - apt w/ pool, Wi Fi, ac, TV

Enjoy a perfect holiday in our flat! Ideal for those travelling with family or friends, you'll stay less than 100 metres from the sea, in a cosy residence with a beautiful swimming pool, close to all essential services, for a comfortable and relaxing stay! The location is also convenient for visiting much of Tuscany, about an hour and a half's drive from Florence, and less than an hour from Livorno, Pisa and Lucca!

Sep 12 – 19

G$29,809 GYD per night

Guest favorite

Villa in Lucca

5.0 out of 5 average rating, 16 reviews

VILLA GIOMA - Rustic completely renovated

Charming rustic located on top of a private hill, complete remodeled in 2023 with private infinity pool surrounded by nature. The farmhouse has comfortable outdoor spaces where you can eat and relax in front of a breathtaking view. The whole house is equipped with air conditioning and each bedroom has a private bathroom. We charge an additional cost of 30€ per day for utilities to be paid at check in.

Feb 22 – Mar 1

G$144,390 GYD per night