San Simone Holiday Rentals

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Our top choices for San Simone holiday rentals

Masseria Corte degli Aromi

Masseria Corte degli Aromi
Palmariggi
9.8 out of 10, Exceptional, (11)
"Fantastic Masseria with excellent food"
Sweden
Nathalie France
The price is AU$512
includes taxes & fees
18 Dec - 19 Dec
Masseria Corte degli Aromi

Relais Il Mignano

Relais Il Mignano
Centro Storico
8.4 out of 10, Very good, (28)
"È stato meraviglioso soggiornare da voi❣️ Tutto bellissimo, pulitissimo ed elegante 😍 la colazione ricca e deliziosa......le torte di Luana insuperabili💞"
Italy
Raffaella
Relais Il Mignano

La Collina di Montegrappa - Suites with Heated Private Pool - Suites with Shared Pool

La Collina di Montegrappa - Suites with Heated Private Pool - Suites with Shared Pool
Tuglie
10.0 out of 10, Exceptional, (2)
"Sehr gepflegte Anlage. Die Hausdame spricht sehr gut Englisch, ist unglaublich hilfsbereit, herzlich und ganz reizend. Das Deluxe Studio ist fantastisch, die Terasse ist riesig. Da es eine Spülmaschine gibt, wäre etwas mehr Besteck wünschenswert. Wir hatten nur 3 Sets. Hinter der Anlage liegt eine Firma mit LKWs die sehr früh mit den Arbeiten beginnt, was durchaus nervig sein kann. Da wir tagsüber unterwegs waren, war uns das egal, wer den Tag auf der sehr schönen Terrassen verbringen will,...
Germany
Nirwana
The price is AU$470
includes taxes & fees
13 Jan - 14 Jan 2026
La Collina di Montegrappa - Suites with Heated Private Pool - Suites with Shared Pool

Royal House

Royal House
Copertino
9.4 out of 10, Exceptional, (11)
"the apartment was very clean, spacious, modern and comfortable. A kitchenette forms part of the apartment. Massimo the owner, was very friendly and helpful. The apartment is only a few minutes walk from the historical centre. The only downside that we were at the second floor and there is no lift. A big plus Massimo's father runs the shop next door to the apartments and he is there from very early in the morning till late in the evening. "
Ireland
Paul
The price is AU$103
includes taxes & fees
25 Dec - 26 Dec
Royal House

Panacea Residence

Panacea Residence
Santa Cesarea Terme
10.0 out of 10, Exceptional, (3)
"Super lieve mensen, spreken wel nauwelijks engels. Bio produkten, lekkere maaltijden, prachtige home made taarten"
Belgium
Anonymous traveller
Panacea Residence

Borgoterra

Borgoterra
Martano
9.0 out of 10, Wonderful, (39)
"For a few days of relaxing this hotel and spa is a good place. "
United States
Johann
The price is AU$146
includes taxes & fees
24 Dec - 25 Dec
Borgoterra

Hotel L'Uomo e il Mare

Hotel L'Uomo e il Mare
Gallipoli
9.0 out of 10, Wonderful, (18)
"Great staff easy to find the hotel too"
Canada
david
Hotel L'Uomo e il Mare

Domus Dejana

Domus Dejana
Gallipoli Historic Center
10.0 out of 10, Exceptional, (16)
"Best breakfast and place to have it on the rooftop "
Sweden
Lars Goran
Domus Dejana

LE DUE DIMORE

LE DUE DIMORE
Collepasso
The price is AU$109
includes taxes & fees
23 Dec - 24 Dec
LE DUE DIMORE

Villa Ghetta Country House

Villa Ghetta Country House
Leverano
8.0 out of 10, Very good, (7)
"Très cher pour ce que c est"
France
brigitte
Villa Ghetta Country House

Lùmia Lecce - Urban Residence

Lùmia Lecce - Urban Residence
Lecce
The price is AU$231
includes taxes & fees
13 Jan - 14 Jan 2026
Lùmia Lecce - Urban Residence

Torre Vecchia Relais

Torre Vecchia Relais
Ugento
The price is AU$229
includes taxes & fees
26 Dec - 27 Dec
Torre Vecchia Relais

B&B CENTRALE

B&B CENTRALE
Gallipoli
6.0 out of 10, (1)
"Hôtel "
France
clement
The price is AU$88
includes taxes & fees
7 Jan - 8 Jan 2026
B&B CENTRALE

Mono P/P Aphrodite 13D

Mono P/P Aphrodite 13D
Torre Mozza
10.0 out of 10, Exceptional, (1)
"Sono stato in un appartamento molto confortevole, dotato di tutti i comfort e situato vicino al mare. Per me che vado in bici, la posizione è davvero strategica: perfetta per raggiungere Santa Maria di Leuca e percorrere la splendida litoranea che porta a Otranto. Che dire… tutto perfetto: cibo, mare, location. Grazie di tutto!"
Italy
rosario f.
The price is AU$123
includes taxes & fees
14 Dec - 15 Dec
Mono P/P Aphrodite 13D

La Pineta

La Pineta
Lecce
The price is AU$109
includes taxes & fees
13 Jan - 14 Jan 2026
La Pineta

PALAZZO GARZIA - Dimora Storica

PALAZZO GARZIA - Dimora Storica
Centro Storico
The price is AU$234
includes taxes & fees
17 Dec - 18 Dec
PALAZZO GARZIA - Dimora Storica

Suite Porta Terra

Suite Porta Terra
Gallipoli Historic Center
6.8 out of 10, (8)
"La réception se trouve à 10min a pied de l hôtel Nous avons pas été prévenu à l’avance. Le logement est sombre, donne sur une mini cour intérieure/terrasse partagée avec un autre logement et où sont entreposés un ancien meuble de salle de bain et une échelle. Il y avait même une vielle assiette en plastique. Pour finir, la montée de escalier est très penture et étroite, pas du tout pratique avec des valises Autrement la chambre est correcte"
France
Florian
The price is AU$114
includes taxes & fees
13 Jan - 14 Jan 2026
Suite Porta Terra

La Lanterna

La Lanterna
Martano
10.0 out of 10, Exceptional, (2)
"Hotel in zona ottimale per il raggiungimento di tutte le località salentine sia dalla parte ionica che Adriatica. Molto pulito, camere spaziose e ben attrezzate, personale estremamente gentile ed accogliente."
Italy
PEDRINAZZI
La Lanterna

HOLIDAY HOUSE VICTORY

HOLIDAY HOUSE VICTORY
Vignacastrisi
10.0 out of 10, Exceptional, (2)
"Ottima ospitalita la propietaria una persona gentile e precisa,la casa pulita e curata in ogni dettaglio completa di tutto, sicuramente ci ritorneremo molto volentieri"
Italy
Cosima S.
The price is AU$141
includes taxes & fees
1 Jan - 2 Jan 2026
HOLIDAY HOUSE VICTORY

Dimore Arcudi

Dimore Arcudi
Galatina Historic Centre
The price is AU$98
includes taxes & fees
18 Dec - 19 Dec
Dimore Arcudi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top San Simone Hotel Reviews

Find out more about San Simone

Everything you need to know about San Simone holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the San Simone holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect San Simone holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

San Simone holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in San Simone. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A San Simone holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of San Simone holiday rentals we have selected for you start as low as AU$470 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on San Simone rentals

At Expedia, we put the best San Simone holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top San Simone rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream San Simone holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around San Simone. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in San Simone?

Yes, there are holiday rentals close to the most popular sights in San Simone, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that San Simone has to offer?

Kalinifta Rooms Apartment: This holiday home rental outside of San Simone is located on the waterfront, and has a private balcony, a rooftop terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities such as a fridge and kitchenware can make your holiday run smoothly. You and your friends and family can relax into your holiday with amenities such as a garden.

What can I see and do in San Simone?

While exploring the area, visit family-friendly sights like Parco Acquatico Splash, or get outside and enjoy nature at Padula Bianca Beach. In the wider area, you’ll find Rivabella Beach and Lido Conchiglie Beach.

What are holiday rentals like in San Simone?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in San Simone. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.