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San Simone Holiday Rentals

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Our top choices for San Simone holiday rentals

1. Masseria Carignani

Masseria Carignani
3.0 star property
Tuglie
9.6 out of 10, Exceptional, (7 reviews)
"The team, the breakfast, the setting and the room were all absolutely wonderful Highly recommend "
United Kingdom
giles
The price is NZ$211
includes taxes & fees
29 Aug - 30 Aug
Masseria Carignani

2. Masseria Li Foggi

Masseria Li Foggi
Gallipoli
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful property Nice restaurant Good service Close to amazing beaches! "
United States
Tanya
The price is NZ$403
includes taxes & fees
27 Aug - 28 Aug
Masseria Li Foggi

3. Villa il Panorama sullo Ionio

Villa il Panorama sullo Ionio
Tuglie
The price is NZ$611
includes taxes & fees
29 Aug - 30 Aug
Villa il Panorama sullo Ionio

4. 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, (3 reviews)
"Had a great stay!!"
United Kingdom
Sophie
The price is NZ$496
includes taxes & fees
10 Sept - 11 Sept
La Collina di Montegrappa - Suites with Heated Private Pool - Suites with Shared Pool

5. Equinox house

Equinox house
Tuglie
10.0 out of 10, Exceptional, (1 review)
"Super séjour... très belle terrasse... logement calme et très jolie village... merci"
France
Nadège
The price is NZ$168
includes taxes & fees
26 Aug - 27 Aug
Equinox house

6. Villa Dune Luxury Roof Top Pool Wellness

Villa Dune Luxury Roof Top Pool Wellness
Gallipoli
10.0 out of 10, Exceptional, (6 reviews)
"We had a fabulous stay! Such a lovely family run boutique hotel. Very clean and lovely roof top terrace. "
United Kingdom
cathy
The price is NZ$484
includes taxes & fees
5 Sept - 6 Sept
Villa Dune Luxury Roof Top Pool Wellness

7. Relais Regina Rosanna

Relais Regina Rosanna
Gallipoli
9.2 out of 10, Wonderful, (15 reviews)
"Insgesamt eine tolle moderne Unterkunft und freundliches Personal. Mit dem Auto sehr nah an der Stadt gelegen. Leider wurden bei unserem Aufenthalt von vier Tagen kein Mal die Handtücher gewechselt, außerdem gab es keine Handtücher für den Pool oder die Außendusche (lediglich 6 Stück für die gesamte Unterkunft) und die normalen durften für den Pool nicht genutzt werden. Das Frühstück war gut, es hätte aber etwas abwechslungsreicher sein können. Ich hätte mich außerdem gefreut, wenn das Personal...
Germany
Lilian
The price is NZ$209
includes taxes & fees
16 Sept - 17 Sept
Relais Regina Rosanna

8. Palazzo Mosco

Palazzo Mosco
4.0 star property
Gallipoli Historic Center
9.0 out of 10, Wonderful, (175 reviews)
"I loved this property…they had to switch us to a neighbouring sister property which we loved. Clean, comfy beds, attentive staff, great dip pool, quiet and convenient location in the heart of Gallipoli. Antonio was fabulous and helpful. I absolutely would stay here if I return to Gallipoli and I am looking forward to staying any other property they have."
Canada
Deanna
The price is NZ$268
includes taxes & fees
14 Sept - 15 Sept
Palazzo Mosco

9. Ventidimaregallipoli

Ventidimaregallipoli
Gallipoli
10.0 out of 10, Exceptional, (2 reviews)
"Magnifique chambre, grand patio et commodités, près du centre et des plages. Notre hôte Bruno était vraiment sympathique et facilement rejoignable. Nous avons eu un merveilleux séjour, je recommande cet endroit. "
Canada
Guylaine
The price is NZ$168
includes taxes & fees
15 Sept - 16 Sept
Ventidimaregallipoli

10. Holiday Home L'Angolo di Giadia with Pool, Terrace & Wi-Fi

Holiday Home L'Angolo di Giadia with Pool, Terrace & Wi-Fi
Matino
10.0 out of 10, Exceptional, (2 reviews)
"Pros: The house had a wonderful pool and terrace. Gianfranco and his wife Claudia made us feel very welcomed. Thank you so much. Cons: Nothing"
United States
Anonymous traveller
The price is NZ$920
includes taxes & fees
4 Sept - 5 Sept
Holiday Home L'Angolo di Giadia with Pool, Terrace & Wi-Fi

11. B&B CENTRALE

B&B CENTRALE
Gallipoli
8.0 out of 10, Very good, (2 reviews)
"Bien situé a 2 pas du centre historique, très propre et personnel sur place dans le bar d à côté. Le petit déjeuner au choix au bar"
Belgium
Felice
The price is NZ$118
includes taxes & fees
25 Sept - 26 Sept
B&B CENTRALE

12. Salapolis Luxury Apartments

Salapolis Luxury Apartments
Gallipoli Historic Center
10.0 out of 10, Exceptional, (11 reviews)
"Utmärkt läge, fin lägenhet och mycket trevlig personal."
Sweden
Henriette
The price is NZ$840
includes taxes & fees
18 Sept - 19 Sept
Salapolis Luxury Apartments

13. Bòmera Rooms

Bòmera Rooms
Gallipoli
8.8 out of 10, Excellent, (3 reviews)
"Great price for value "
United States
Marika
The price is NZ$138
includes taxes & fees
14 Sept - 15 Sept
Bòmera Rooms

14. Domus Dejana

Domus Dejana
Gallipoli Historic Center
9.8 out of 10, Exceptional, (20 reviews)
"Best breakfast and place to have it on the rooftop "
Sweden
Lars Goran
The price is NZ$197
includes taxes & fees
30 Aug - 31 Aug
Domus Dejana

15. LE DUE DIMORE

LE DUE DIMORE
Collepasso
The price is NZ$123
includes taxes & fees
6 Sept - 7 Sept
LE DUE DIMORE

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

Holiday Home 'Tenuta Lu Mimmu' with Private Terrace, Wi-Fi and Air Conditioning
Matino
9.0 out of 10, Wonderful, (2 reviews)
"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...
Netherlands
Anonymous traveller
The price is NZ$881
includes taxes & fees
1 Sept - 2 Sept
Holiday Home 'Tenuta Lu Mimmu' with Private Terrace, Wi-Fi and Air Conditioning

17. Villa Giovanna

Villa Giovanna
Racale
9.8 out of 10, Exceptional, (8 reviews)
"Personnel super sympathique. Bon acceuil. Vu la basse saison et la faible occupation nous avons été upgradé dans une chambre avec terrasse et au calme. Petit dejeuner copieux et varié. Fruits, sucré et salé au choix et en quantité. Top petit séjour de 2 nuits en couple. Petit bémol, les chambres sont vraiment pas grandes...."
Belgium
DOMINIQUE
The price is NZ$59
includes taxes & fees
18 Sept - 19 Sept
Villa Giovanna

18. Apartment 'Suite Buena Vista' with Sea View, Balcony and Air Conditioning

Apartment 'Suite Buena Vista' with Sea View, Balcony and Air Conditioning
Gallipoli
10.0 out of 10, Exceptional, (2 reviews)
"Pros: The location, the view and the very well furnished flat Cons: Nothing"
United States
Anonymous traveller
Apartment 'Suite Buena Vista' with Sea View, Balcony and Air Conditioning

19. Donna Grazia

Donna Grazia
Gallipoli Historic Center
9.0 out of 10, Wonderful, (7 reviews)
"Nice staff, great location, very artistic and very comfortable "
Canada
Esmaeil
The price is NZ$425
includes taxes & fees
6 Sept - 7 Sept
Donna Grazia

20. PALAZZO GARZIA - Dimora Storica

PALAZZO GARZIA - Dimora Storica
Centro Storico
10.0 out of 10, Exceptional, (2 reviews)
"Sublime palais en plein centre de maglie avec une piscine superbe et des propriétaires très gentils"
France
Yves-Marie
The price is NZ$247
includes taxes & fees
28 Aug - 29 Aug
PALAZZO GARZIA - Dimora Storica
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our San Simone holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up San Simone. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in San Simone. Seeing all the best attractions is bound to make you fall in love with San Simone. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in San Simone short-term rentals, that won’t be hard to do.

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?

Masseria Relais Santa Teresa: This holiday home rental outside of San Simone is located in a rural location, and has a rooftop pool, a terrace and air conditioning to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. 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.