Search vacation rental in San Cassiano from 100+ sites!

36 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
San Cassiano vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in San Cassiano

Best family friendly San Cassiano vacation rentals

Among the 36 accommodations in San Cassiano, here are the 4 best family friendly rentals

Casa Del Glicine Andrano - San Cassiano
9.5 20 reviews

Casa Del Glicine Andrano

studio, Andrano
Casa del Glicine Andrano is located in the quiet town of Andrano, just a short drive from the stunning Grotta Zinzulusa sea cave and the historic town of Otranto. This charming apartment is perfect for a relaxing getaway, offering easy access to the area's top attractions.
The studio apartment features a comfortable bedroom and bathroom, a fully equipped kitchenette, and a private terrace. You can enjoy free Wi-Fi, air conditioning, and parking, making your stay even more enjoyable.
Apartment 'Casa Aurora Luxury' With Shared Pool, Wi-fi And Air Conditioning - San Cassiano
9.6 19 reviews

Apartment 'Casa Aurora Luxury' With Shared Pool, Wi-fi And Air Conditioning

apartment, Giuggianello
This Giuggianello rental is situated 1.9 miles from La Cutura Botanical Garden and within 6 miles of Cantine Menhir and Dolmen Li Scusi, offering easy access to local attractions.
This 1400-square-foot apartment sleeps six, features two bedrooms, one bathroom, a fully equipped kitchen, a private patio, a swimming pool, and free Wi-Fi.
Villaelena - San Cassiano
10 65 reviews

Villaelena

house, Diso
Villaelena, a recently renovated allergy-free vacation home in Diso, Italy, is located approximately 1.2 miles from Cala dell'Acquaviva and Cala 71 beaches, and 1.2 miles from Spiaggia dei Porticelli beach.
This 680-square-foot (approximately 63 square meter) house features two bedrooms, one bathroom, a fully equipped kitchen, a private garden with barbecue, and amenities for families and disabled guests, including free Wi-Fi.
Il Giardino Segreto - San Cassiano
9.8 12 reviews

Il Giardino Segreto

apartment, Maglie
Il Giardino Segreto, a Maglie apartment rental, is conveniently located near Otranto Castle (12 miles) and Lecce's Piazza Sant'Oronzo and Piazza Mazzini (20 miles), offering easy access to Salento's historical sites.
This 1310-square-foot (121-square-meter) family-friendly dwelling boasts two bedrooms, one bathroom, and can comfortably accommodate up to six guests, featuring a private garden, air conditioning, Wi-Fi, and a balcony.

Best San Cassiano vacation rentals with a fireplace

Abitazione Privata Nel Cuore Del Salento - San Cassiano
9.7 53 reviews

Abitazione Privata Nel Cuore Del Salento

apartment, Muro Leccese
This two-bedroom apartment in Muro Leccese, a charming town located 22 miles from Lecce's Piazza Sant'Oronzo and 9.4 miles from Grotta Zinzulusa, offers a comfortable and spacious accommodation for families or groups of friends. The 1,380 square foot apartment features a fully equipped kitchen, a fireplace, a private balcony, and a garden, perfect for enjoying the Salento region's warm climate.
La Sterna - San Cassiano
9.9 10 reviews

La Sterna

house, Montesano Salentino
This spacious vacation rental in Montesano Salentino is located 8.1 miles from Grotta Zinzulusa and 16 miles from Castello di Otranto.
This two-bedroom, two-bathroom house offers 1400 square feet of living space for up to six guests, featuring a fully equipped kitchen, WiFi, air conditioning, a garden with barbecue facilities, and free private parking.
La Casetta Di Giulia - San Cassiano
8.7 4 reviews

La Casetta Di Giulia

apartment, Spongano
La Casetta di Giulia is an apartment in Spongano, located 5.1 miles from Grotta Zinzulusa and 13 miles from Castello di Otranto.
This 650 sq ft residence offers 1 bedroom, 1 bathroom, and accommodates up to 7 guests with a fully equipped kitchen featuring an oven and coffee machine, air conditioning, WiFi, and an on-site garden.
Tenuta Pizzola - San Cassiano
9.6 6 reviews

Tenuta Pizzola

house, Nociglia
Tenuta Pizzola, located in Nociglia, Italy, is a short drive (8.9 miles) from Grotta Zinzulusa cave and about 22-25 miles from larger towns like Roca.
This 1,160-square-foot house features two bedrooms, one bathroom, and accommodates up to 12 guests, offering a private patio with barbecue, free Wi-Fi, parking, air conditioning, and a fully equipped kitchen; nearby hiking and cycling trails provide additional recreational opportunities.

Frequently Asked Questions about vacation rentals in San Cassiano

  • What are some interesting places to visit in or near San Cassiano?

    San Cassiano is a great base for exploring the Dolomites. You can visit the stunning Lago di Braies, a turquoise lake surrounded by mountains, or take a scenic drive to Cortina d'Ampezzo, a charming town known for its winter sports and luxury shopping. The Natural Park of Fanes-Sennes-Braies is a must-see for nature lovers, with its diverse flora and fauna.
  • What are the best Airbnb and vacation rentals in San Cassiano?

    Winery 1700 Historic Maison With Private Pool And Big Garden, La Casa Dell’ecoturista and Oikia Vacanze Giuggianello Le Bey are the most popular Airbnb and vacation rentals in San Cassiano among travelers.

  • Which walking or cycling routes are the best in San Cassiano?

    The Alta Via 1 trail is a popular hiking route that passes through San Cassiano, offering breathtaking views of the Dolomites. For cycling, the Dolomiti Road Bike route is a challenging but rewarding ride, taking you through some of the most scenic passes in the region. The Val Badia Cycle Path is a more relaxed option, perfect for families.
  • What are the most popular Airbnbs in San Cassiano?

  • What sports or outdoor activites can visitors enjoy in and around San Cassiano?

    San Cassiano is a paradise for outdoor enthusiasts. In the winter, you can ski, snowboard, and cross-country ski at the nearby Alta Badia ski area. In the summer, you can hike, mountain bike, rock climb, and go paragliding. There are also plenty of opportunities for fishing and swimming in the surrounding lakes and rivers.
  • What are the best vacation rentals with a pool in San Cassiano?

  • What other towns or cities can be easily accessed from San Cassiano?

    From San Cassiano, you can easily reach other charming towns in the Dolomites, like Cortina d'Ampezzo, Bolzano, and Brunico. These towns offer a variety of attractions, including museums, art galleries, and historical landmarks.
  • What are the best rentals for families and kids in San Cassiano?

  • What amenities are commonly available in vacation rentals in San Cassiano?

    Vacation rentals in San Cassiano typically offer a range of amenities, including Wi-Fi, a fully equipped kitchen, a washing machine, and a balcony or patio with mountain views. Many rentals also have a fireplace, a sauna, or a hot tub.
  • What are the best rentals or Airbnbs with a jacuzzi in San Cassiano?

    The best vacation rentals or Airbnb with a jacuzzi in San Cassiano are Winery 1700 Historic Maison With Private Pool And Big Garden, Oikia Vacanze Giuggianello Le Bey and Relais L'oliveto.

  • What time of year is best to rent a vacation rental San Cassiano?

    The best time to visit San Cassiano depends on your interests. If you're looking for snow sports, winter is the ideal time. For hiking and biking, summer is the best season. Spring and fall offer pleasant weather and fewer crowds.
  • What are the local dishes in San Cassiano region?

    The local cuisine in San Cassiano is hearty and delicious. Try the traditional dishes like 'casunziei,' buckwheat dumplings filled with spinach and ricotta, or 'pizzoccheri,' a pasta dish made with buckwheat flour, potatoes, and cabbage. You can also find a variety of local cheeses and cured meats.

Popular destinations

Guest-Favorite Vacation Rentals with Jacuzzi in San Cassiano

These vacation rentals in San Cassiano feature private hot tubs and jacuzzis, perfect for a relaxing soak.

Villa Buon Vento - San Cassiano
9.0 24 reviews

Villa Buon Vento

house, Ortelle
Villa Buon Vento, located in Vignacastrisi near Ortelle, Italy, is a short drive from Castro Marina Beach (1.2 miles) and Cala dell'Acquaviva Beach (1.8 miles).
This recently renovated 2640-square-foot vacation home boasts four bedrooms, two bathrooms, and can accommodate up to 19 guests, featuring a private pool, Jacuzzi, spa, and outdoor amenities such as a barbecue and playground.
Villa Raffaella - Spongano - San Cassiano
10 5 reviews

Villa Raffaella - Spongano

house, Spongano
This villa in Spongano offers a tranquil setting, located 24 miles from Roca and 27 miles from Piazza Mazzini.
This 3,230 square foot villa accommodates up to 11 guests with 3 bathrooms, featuring air conditioning, a private patio, a shared seasonal swimming pool, a hot tub, a garden, and a fully equipped kitchen with a dishwasher and oven, plus complimentary WiFi.
Alternative Resort & Spa - San Cassiano
No reviews

Alternative Resort & Spa

apartment, Scorrano
This resort in Scorrano is situated 19 miles from Roca and 22 miles from Piazza Mazzini, with Brindisi - Salento Airport located 49 miles away.
This family-friendly apartment offers 1610 square feet of living space with 3 bedrooms, 2 bathrooms, a fully equipped kitchen, and can accommodate up to 19 guests, featuring amenities such as a swimming pool, jacuzzi, sauna, garden, terrace, and private parking.
Sweet Loft Maglie - San Cassiano
9.9 9 reviews

Sweet Loft Maglie

apartment, Maglie
Sweet Loft Maglie, a one-bedroom apartment in Maglie, Italy, offers easy access to Otranto (12 miles away), Roca (17 miles away), and Lecce (approximately 20 miles away), allowing for convenient day trips to historical sites like Otranto's Castello and Grotta Zinzulusa.
This 540-square-foot (approximately 50-square-meter) rental features a fully equipped kitchen, a private terrace, and can comfortably accommodate up to seven guests, with amenities including air conditioning, Wi-Fi, and on-site parking.

Best San Cassiano vacation rentals with parking

A Casa Di Nonna Nnina - San Cassiano
9.4 8 reviews

A Casa Di Nonna Nnina

house, Montesano Salentino
This vacation rental in Montesano Salentino is located 8.1 miles from Grotta Zinzulusa and 17 miles from Castello di Otranto, with Lecce's main squares over 25 miles away.
This pet-friendly house accommodates up to 8 guests, offering air conditioning, a full kitchen, and garden views, with a check-out time between 8:00 AM and 10:00 AM.
Clementina - San Cassiano
9.7 7 reviews

Clementina

apartment, Maglie
This apartment rental in Maglie is located in a quiet district, a short walk from the historic center and close to amenities like a supermarket and tobacconist.
This 2-bedroom, 1-bathroom condo accommodates up to 4 guests and features air conditioning, a full kitchen, free parking, and balconies in every room, offering a comfortable base for exploring the Salento Coast.
Casa Venere Luxury Apartment - San Cassiano
9.0 1 review

Casa Venere Luxury Apartment

apartment, Giuggianello
Casa Venere Luxury Apartment is located in Giuggianello, a short drive from the Castello di Otranto and the Otranto Porto.
This 1,400 square-foot apartment features two bedrooms, one bathroom, a kitchen with a fridge, a terrace, a garden, a swimming pool, and parking, and can accommodate up to 10 guests.
Tenuta San Cassiano With Garden And Pool - Happy Rentals - San Cassiano
9.0 5 reviews

Tenuta San Cassiano With Garden And Pool - Happy Rentals

house, San Cassiano
This spacious San Cassiano villa, part of Tenuta San Cassiano, is located 7.1 miles from Grotta Zinzulusa cave and about 24 miles from Roca and Piazza Mazzini.
The 3500-square-foot residence boasts six bedrooms, four bathrooms, and accommodates up to 29 guests, featuring a private pool, garden, terrace, free Wi-Fi, and parking.

Our Favorite 5-Star Vacation Rentals in San Cassiano

Experience elite mountain living in a luxury vacation rental in San Cassiano, offering 5-star comfort from the moment you arrive.

Dimora Paolina Boutique House & Private Pool - San Cassiano
10 2 reviews

Dimora Paolina Boutique House & Private Pool

house, Montesano Salentino

Check Out Pet-Friendly Vacation Rentals in San Cassiano

Booking a dog-friendly vacation rental makes traveling with pets to San Cassiano completely seamless.

Un Terrazzino Sul Mare - San Cassiano
No reviews

Un Terrazzino Sul Mare

house, Castro
Portaterra Antica Dimora - San Cassiano
9.1 2 reviews

Portaterra Antica Dimora

house, Scorrano
Casa A Levante - San Cassiano
9.5 4 reviews

Casa A Levante

apartment, Ortelle
La Terrazza Sul Mare - San Cassiano
9.5 4 reviews

La Terrazza Sul Mare

apartment, Castro

Search Vacation Rentals with a Pool in San Cassiano

Book a San Cassiano vacation rental with a pool to enjoy a swim after a day on the slopes.

Wp Relais Apartments - San Cassiano
9.4 122 reviews

Wp Relais Apartments

apartment, Diso
Antica Masseria Arnoni - San Cassiano
10 7 reviews

Antica Masseria Arnoni

farm, San Cassiano
Infinity - Cycladic Experience - San Cassiano
10 4 reviews

Infinity - Cycladic Experience

house, Spongano
Tenuta San Cassiano With Garden And Pool, San Cassiano, Italy - San Cassiano
No reviews

Tenuta San Cassiano With Garden And Pool, San Cassiano, Italy

house, San Cassiano
©2026 cozycozy.com