San Simone Holiday Rentals from €31: Search Short-Term Rentals

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

Tenuta Marrocco House : This holiday home rental outside of San Simone offers a terrace and WiFi to help you feel comfortable in your new surroundings.

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Our top choices for San Simone holiday rentals

A dining area with tables set for two, a wicker hanging light fixture, and a view of a lush garden.

1. Masseria Li Foggi

Gallipoli

Jaime

includes taxes & fees

29 Oct - 30 Oct

A poolside area with lounge chairs, a pool, and a tropical garden.

2. Relais Regina Rosanna

Gallipoli

Océane

A rooftop pool area with wooden loungers and a hot tub.

3. Equinox house

Tuglie

Nadège

includes taxes & fees

4 Oct - 5 Oct

4. Villa Giovanna

Racale

"LIiRE très attentivement les informations. Car je suis arrivée vers 22h30 et il n'y a personne à la réception..dans la précipitation de mon départ réservation la veille j' ai pas fait attention aux horaires mais c'est écrit. Le chekin se termine à 19h30 ce qui est déjà très tôt. Mais aucune personne pour vous donner les clefs sauf si vous appelez et déboursé 50 euros !!! Plus cher que le prix votre nuits !!! Mais une personne est arrivée dans le demi-heure. La chambre malgré que tout était...

Silvana

includes taxes & fees

6 Oct - 7 Oct

A sunset view from a poolside area with lounge chairs and a glass of wine.

5. Villa Dune Luxury Roof Top Pool Wellness

Bai Verde

cathy

includes taxes & fees

11 Oct - 12 Oct

A rooftop terrace with white wicker furniture, potted plants, and a view of the sea.

6. Palazzo Mosco

Gallipoli Historic Center

Deanna

includes taxes & fees

12 Oct - 13 Oct

A sunlit outdoor seating area with wicker furniture, a cactus plant, and a tray with bread and flowers.

7. Domus Dejana

Gallipoli Historic Center

Alberto

includes taxes & fees

4 Oct - 5 Oct

An outdoor dining area with tables and chairs, surrounded by stone walls and greenery.

8. Relais Il Mignano

Centro Storico

Pasquale

includes taxes & fees

6 Oct - 7 Oct

A hotel room with a bed, two bedside tables, a sofa, and an air conditioning unit.

9. LE DUE DIMORE

Collepasso

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a bed, bedside tables, a chair, and a view of an outdoor balcony.

10. Ventidimaregallipoli

Lido San Giovanni

Maria

includes taxes & fees

4 Oct - 5 Oct

An outdoor dining area with a white table, chairs, and a red flower vase.

11. Holiday Home 'Angel' with Private Terrace, Wi-Fi and Air Conditioning

Galatone

Anonymous traveller

A swimming pool with lounge chairs, a pergola, and a house in the background.

12. Holiday Home 'Villa Relax' with Shared Pool & Wi-Fi

Galatone

Anonymous traveller

A dining area with a wooden table set for four, surrounded by white chairs, with a view of greenery outside.

13. Holiday Home 'Tenuta Lu Mimmu' with Private Terrace, Wi-Fi and Air Conditioning

Matino

"Pros: Het huis heeft charme! De woonkamer is heel gezellig. De buitenkeuken en de tuin zijn heel fijn om te gebruiken. Er zijn geen buren dus het is heel rustig, ook ‘s nachts hoor je niets. De airco in elke kamer was heel fijn. Er is een zwerfkat die heel lief is. Dat vonden we een hele leuke toevoeging aan het huis. De keuken is erg goed ingericht en heeft veel handige producten. Er is super mooi/leuk cactus servies in de mooie kast. Het huis is erg ruim! Cons: De douche is aan...

Anonymous traveller

includes taxes & fees

16 Oct - 17 Oct

A beach with clear water and gentle waves.

14. Emblem apartment with terrace near the sea Gallipoli Mancaversa in Salento

Marina di Mancaversa-giannelli

"We arrived at the house and Massimo showed us the apartment that we were to stay in. At first it looked big enough but after a day we realised that it only had a bedroom and ensuite bathroom with a kitchen leading out onto a yard that had table and chairs, washing machine and a shower area. We realised we had no windows, only the light coming in from the glass windows on the doors. Apart from that the fixtures and fittings were ok. What we didn't know and did not find out until we arrived was...

harry w.

includes taxes & fees

5 Oct - 6 Oct

15. Villa Ghetta Country House

Leverano

Stefania

includes taxes & fees

25 Oct - 26 Oct

A spacious interior with a high arched ceiling, a bar area with stools, and a seating area with two chairs.

16. Palazzo Circolone

Poggiardo

David

includes taxes & fees

5 Oct - 6 Oct

A room with a fireplace, a television mounted above it, and a hot tub in the foreground.

17. Trullo Raeda

Nardò

"Zu Zweit hatten wir hier eine sehr schöne Zeit. Wir haben viel genutzt (Whirlpool, Pool, Karmin, Küche). Die Küche ist sehr gut ausgestattet und für einen Trullo groß, was uns wichtig war. Insgesamt würden wir das Objekt jedoch auch nur für 2 Personen empfehlen, da das Bad nur vom Schlafzimmer aus, erreichbar ist und die Tür sehr laut ist. Auch ist der Geruch im Badezimmer durchaus ein Problem. Wenn weitere Personen hinzukämen, würden diese auf Klappsofas in der Küche oder im Anbau schlafen,...

Ralf B.

includes taxes & fees

16 Oct - 17 Oct

A balcony with potted plants and a metal watering can.

18. B&B Dimora San Vincenzo

Gallipoli Historic Center

"This B&B is located in the very heart of historical center of Gallipoli and within a walking distance to everything important. It has no lift but a lot of stairs. The breakfast was served on the roof terrace. The property is not reachable by car (you will need to walk with your luggage at least 150 metres) and has NO parking, even though the property info on hotels.com says that "it is available". We ended up parking 1km away from this place. "

Erich

A hotel room with a bed, bedside table, lamp, and a painting on the wall.

19. Suite Porta Terra

Gallipoli Historic Center

"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"

Florian

includes taxes & fees

4 Oct - 5 Oct

A coastal area with clear blue water, rocky shore, and buildings in the background.

20. Emblem 02 Comfortable apartment near the sea Gallipoli Mancaversa Salento

MARINA DI MANCAVERSA

"L'appartamento molto luminoso e spazioso era perfettamente pulito e in buono stato!Il servizio fornito da Massimo è stato di ottima qualità. Consiglierei a chiunque questa struttura, vicinissima alle spiagge sabbiose della movida Salentina e altrettanto vicina alle altre spiagge più tranquille. Massimo è una persona splendida,sempre disponibile . Grazie per averci fatto trascorrere una vacanza indimenticabile. Ci rivedremo presto ! Saluti "

rosalia v.

includes taxes & fees

5 Oct - 6 Oct

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Top San Simone Hotel Reviews

Grand Hotel di Lecce

10/10 Excellent

"A good one night stay. Very close to the train station so handy for onward travel. Breakfast was quite limited, but apart from that our stay was perfectly fine"

Masseria Donna Menga

10/10 Excellent

"This property is beautiful. The facilities, the staff, the service, the food... We spent a week there, and used it as a base to visit Gallipoli, Nardo, Lecce, Ostuni. It's not a place to spend a week if you are not planning to go sightseeing etc, as it is remote and there's nothing around it. It can be a bit off putting on arrival to see the surrounding area of agricultural land and not much else, but the Masseria itself is an oasis of calm once you are inside. This is a place that needs a car. Although the masseria can arrange taxis, the quotes we had were very expensive, so we relied on our car. Food at the masseria is lovely. We enjoyed good breakfasts and a few evening meals there, which were of very high quality. Above all, it is the truly exceptional staff that make this place - everyone we encountered is a credit to the masseria."

Victoria Palace Hotel & Zen Wellness

10/10 Excellent

"We arrived early and were offered use of the pool, changing room and lunch. Our room was ideal, and well fitted (although no kettle, available on request). It was nice and quiet, both by the pool and in the room, and an easy 5 minute walk to the beachfront with cafes, bars and shops. We had a car and parking was easy, so it made this hotel an ideal base to explore the Salento area and Gallipoli. All the staff were friendly, both on the desk and at breakfast which was a buffet style with some hot options. On departure we were again offered an room extension, use of the pool all day and the Spa to freshen up. All in all could not be faulted."

Palazzo Presta

10/10 Excellent

"Hotel was very helpful with recommendations on places to see and places to eat not only in gallipoli but tricase porto, otranto, and galetina. Also made reservations for us. They were particularly helpful wither parking lot, which is 850 meters from hotel. They had us call ten minutes before arriving in gallipoli and jetty was waiting for us at garage to pick up luggage and take us into old town-no cars. Also fast service to get us to car for drives around area and pickups. We should have stayed 1 or 2 more nights because located nicely in old town near lots of activities."

Le Dune Suite Hotel

8/10 Good

"The breakfast was ok but if you arrived after 9.30 (breakfast finishes at 10am) the food was being cleared away, tables weren't re-laid. Staff at breakfast weren't very friendly and it was difficult getting a coffee. The main waiter was incredibly rude and almost took a croissant from my husband on the first day! Reception staff were friendly and helpful. Room nice - although beware suite if you have mobility issues as bed very low and shower / bath up a number of stairs. Restaurant opposite hotel on beach (where you could use your half board voucher ) was excellent and very good value. Good location for beach and close to bus to harbour area."

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, apart-hotels, 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 favorite 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 depends 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 €31 per night. Entering your travel dates in the search wizard you might find 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?

Tenuta Marrocco House: This holiday home rental outside of San Simone offers a terrace and WiFi to help you feel comfortable in your new surroundings.

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.

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Check prices for these dates

Our top choices for San Simone holiday rentals

1. Masseria Li Foggi

2. Relais Regina Rosanna

3. Equinox house

4. Villa Giovanna

5. Villa Dune Luxury Roof Top Pool Wellness

6. Palazzo Mosco

7. Domus Dejana

8. Relais Il Mignano

9. LE DUE DIMORE

10. Ventidimaregallipoli

11. Holiday Home 'Angel' with Private Terrace, Wi-Fi and Air Conditioning

12. Holiday Home 'Villa Relax' with Shared Pool & Wi-Fi

13. Holiday Home 'Tenuta Lu Mimmu' with Private Terrace, Wi-Fi and Air Conditioning

14. Emblem apartment with terrace near the sea Gallipoli Mancaversa in Salento

15. Villa Ghetta Country House

16. Palazzo Circolone

17. Trullo Raeda

18. B&B Dimora San Vincenzo

19. Suite Porta Terra

20. Emblem 02 Comfortable apartment near the sea Gallipoli Mancaversa Salento

Find holiday rentals that suit your style

Top San Simone Hotel Reviews

Grand Hotel di Lecce

Masseria Donna Menga

Hotel La Roccia

Victoria Palace Hotel & Zen Wellness

CDSHotels Grand Hotel Riviera

Torre Assunta Hotel

Palazzo Presta

Palazzo Mosco

Le Dune Suite Hotel

Find out more about San Simone

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in San Simone

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for San Simone holiday rentals

1. Masseria Li Foggi

2. Relais Regina Rosanna

3. Equinox house

4. Villa Giovanna

5. Villa Dune Luxury Roof Top Pool Wellness

6. Palazzo Mosco

7. Domus Dejana

8. Relais Il Mignano

9. LE DUE DIMORE

10. Ventidimaregallipoli

11. Holiday Home 'Angel' with Private Terrace, Wi-Fi and Air Conditioning

12. Holiday Home 'Villa Relax' with Shared Pool & Wi-Fi

13. Holiday Home 'Tenuta Lu Mimmu' with Private Terrace, Wi-Fi and Air Conditioning

14. Emblem apartment with terrace near the sea Gallipoli Mancaversa in Salento

15. Villa Ghetta Country House

16. Palazzo Circolone

17. Trullo Raeda

18. B&B Dimora San Vincenzo

19. Suite Porta Terra

20. Emblem 02 Comfortable apartment near the sea Gallipoli Mancaversa Salento

Find holiday rentals that suit your style

Top San Simone Hotel Reviews

Grand Hotel di Lecce

Find out more about San Simone

Frequently asked questions

Go further with the Expedia app