Vacation Rentals & Villas in San Gimignano

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5,668 Houses

(5) Excellent 

    31

    Holiday home Il Corbezzolo with Infinity pool

    Province of Siena / San Gimignano

    San Gimignano house

    1 4 min stay varies

    • 1 bedroom
    • sleeps 4
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $150

    Price per night from

    $150

    (3) Excellent 

      3

      CASA ALADINA: STUDIO RIGHT IN THE CITY S.GIMIGNANO

      Province of Siena / San Gimignano

      San Gimignano apartment

      3 3 nights min

      • sleeps 3
      • 3 nights min
      • Ask about children

      Price per night from

      $91

      Price per night from

      $91

      (1) Very Good 

        35

        Tuscan countryhouse apartment in San Gimignano

        Province of Siena / San Gimignano

        San Gimignano apartment

        1 2 3 nights min

        • 1 bedroom
        • sleeps 2
        • 3 nights min
        • Swimming pool
        • Child Friendly
        • Car not necessary

        Price per night from

        $111

        Price per night from

        $111

        (11) Excellent 

          32

          Casa Bartoli at Borgo Mummialla-your Tuscan home !

          Province of Siena / San Gimignano

          San Gimignano apartment

          2 4 5 nights min

          • 2 bedrooms
          • sleeps 4
          • 5 nights min
          • Swimming pool
          • Child Friendly
          • Air conditioning
          “A jewel in the heart of Tuscany.” Booking very easy helped by the owner. Apartment exceptionally comfortable with all the facilities we required. There was no problem moving in thanks to being met by Fabio when we arrived. A beautiful location w

          Price per night from

          $195

          Responds fast!
          avg. 2 hours 23 minutes

          Price per night from

          $195

          (5) Very Good 

            15

            Central apartment in S.Gimignano with parking

            Province of Siena / San Gimignano

            San Gimignano apartment

            2 4 2 nights min

            • 2 bedrooms
            • sleeps 4
            • 2 nights min
            • Nearest beach 70 mi
            • Child Friendly

            Price per night from

            $81

            Price per night from

            $81

            (11) Very Good 

            Certificate of Excellence

              29

              Wonderful self catering apartment in Tuscany

              Province of Siena / San Gimignano

              San Gimignano apartment

              2 4 3 nights min

              • 2 bedrooms
              • sleeps 4
              • 3 nights min
              • Nearest beach 97 mi
              • Swimming pool
              • Child Friendly
              “Fantastic central location to explore Tuscany” This apartment worked wonderfully as a central base as we explored Tuscany on day trips. It was a beautiful oasis to come home to each evening as we enjoyed our days purchase of wine, meats, and cheese in

              Certificate of Excellence

              Price per night from

              $155

              Price per night from

              $155

              (7) Excellent 

                22

                Pretty self catering apartment / private terrace:

                Province of Siena / San Gimignano

                San Gimignano apartment

                1 2 3 nights min

                • 1 bedroom
                • sleeps 2
                • 3 nights min
                • Nearest beach 96 mi
                • Swimming pool
                • Child Friendly
                “The perfect Tuscany setting with the perfect host.” I can not say enough good things about our stay at La Fonte and Maria's efforts to make us feel right at home. Whatever we needed be it directions, day trip suggestions or finding a local dining spo

                Price per night from

                $149

                Price per night from

                $149

                  20

                  CHARME B&B * CAPANNA1826 * San Gimignano Tuscany

                  San Gimignano / Ulignano

                  Ulignano b&b

                  3 2 3 nights min

                  • 3 bedrooms
                  • sleeps 2
                  • 3 nights min
                  • Nearest beach 110 mi
                  • Child Friendly
                  • Air conditioning

                  Price per night from

                  $143

                  Price per night from

                  $143

                  (1) Excellent 

                    13

                    Villa La Ripa - Padronale

                    Province of Siena / San Gimignano

                    San Gimignano villa

                    2 4 min stay varies

                    • 2 bedrooms
                    • sleeps 4
                    • min stay varies
                    • Nearest beach 70 mi
                    • Swimming pool
                    • Child Friendly

                    Price per night from

                    $182

                    Price per night from

                    $182

                    (33) Excellent 

                      20

                      Tuscany Villas La Casetta del Borgo San Gimignano

                      Province of Siena / San Gimignano

                      San Gimignano apartment

                      1 4 min stay varies

                      • 1 bedroom
                      • sleeps 4
                      • min stay varies
                      • Swimming pool
                      • Child Friendly
                      • Private garden
                      “Perfect base to see all that Tuscany has to offer” La Casetta del Borgo was the perfect location for my recent trip to Tuscany with my wife. The unit is located in a resort with plenty of amenities including two pools and a very nice tennis court with

                      Price per night from

                      $77

                      Price per night from

                      $77

                      (13) Excellent 

                        29

                        Apartment Borgo Antico

                        Province of Siena / San Gimignano

                        San Gimignano apartment

                        2 4 3 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 3 nights min
                        • Nearest beach 81 mi
                        • Child Friendly
                        • Car not necessary
                        “superbe apartment at a suberbe place” We stayed at the lovely old town of San Gimignano a year ago. Everything was perfect. We received a warm welcome by a nice old lady. The apartment is just next to the central square in the pedestrian area. In summ

                        Price per night from

                        $100

                        Responds fast!
                        avg. 1 hour 33 minutes

                        Price per night from

                        $100

                          32

                          Vernaccia

                          Province of Siena / San Gimignano

                          San Gimignano villa

                          8 14 min stay varies

                          • 8 bedrooms
                          • sleeps 14
                          • min stay varies
                          • Child Friendly
                          • Ask about pets

                          Price per night from

                          $1,791

                          Price per night from

                          $1,791

                          (1) Excellent 

                            20

                            La Fonte San Gimignano Prov. of Siena

                            San Gimignano / Pancole

                            Pancole apartment

                            2 4 3 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 3 nights min
                            • Swimming pool
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $130

                            Price per night from

                            $130

                            (1) Excellent 

                              26

                              San Gimignano 6 bedroom villa with pool

                              Province of Siena / San Gimignano

                              San Gimignano house

                              6 12 min stay varies

                              • 6 bedrooms
                              • sleeps 12
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Air conditioning

                              Price per night from

                              $642

                              Price per night from

                              $642

                                23

                                La Fonte San Gimignano, Prov. Siena

                                Province of Siena / San Gimignano

                                San Gimignano apartment

                                1 2 3 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 3 nights min
                                • Swimming pool
                                • Child Friendly

                                Price per night from

                                $150

                                Price per night from

                                $150

                                  28

                                  Rustica Progenie - Bungalow (2 + 2)

                                  San Gimignano / Pancole

                                  Pancole apartment

                                  1 4 min stay varies

                                  • 1 bedroom
                                  • sleeps 4
                                  • min stay varies
                                  • Nearest beach 65 mi
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $87

                                  Price per night from

                                  $87

                                  (9) Very Good 

                                    25

                                    Super Self-Catering Apartment in Tuscany

                                    Province of Siena / San Gimignano

                                    San Gimignano apartment

                                    2 4 3 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 3 nights min
                                    • Nearest beach 97 mi
                                    • Swimming pool
                                    • Child Friendly

                                    Price per night from

                                    $130

                                    Price per night from

                                    $130

                                      30

                                      Rustica Progenie - Bilo b (2 + 2)

                                      San Gimignano / Pancole

                                      Pancole apartment

                                      1 4 min stay varies

                                      • 1 bedroom
                                      • sleeps 4
                                      • min stay varies
                                      • Nearest beach 65 mi
                                      • Swimming pool
                                      • Child Friendly

                                      Price per night from

                                      $78

                                      Price per night from

                                      $78

                                      (3) Very Good 

                                        10

                                        Tychehouse Holidays House in Tuscany San Gimignano

                                        Province of Siena / San Gimignano

                                        San Gimignano house

                                        1 5 7 nights min

                                        • 1 bedroom
                                        • sleeps 5
                                        • 7 nights min
                                        • Swimming pool
                                        • Child Friendly
                                        • Pet Friendly
                                        “Excellent apartment” Thank you for everything. We had a wonderful holiday in a quiet and nice. Excellent apartment

                                        Price per night from

                                        $93

                                        Responds fast!
                                        avg. 1 hour 9 minutes

                                        Price per night from

                                        $93

                                          17

                                          Barn Cafaggiola

                                          Province of Siena / San Gimignano

                                          San Gimignano house

                                          3 6 7 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $278

                                          Price per night from

                                          $278

                                          (1) Excellent 

                                            24

                                            Fantastic 2 bedroom apartment in Traditional Tuscan villa with amazing views of the countryside and pool access, sleeps 4

                                            Province of Siena / San Gimignano

                                            San Gimignano apartment

                                            2 4 5 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 5 nights min
                                            • Nearest beach 70 mi
                                            • Swimming pool
                                            • Child Friendly

                                            Price per night from

                                            $143

                                            Price per night from

                                            $143

                                              1

                                              Villa La Ripa - Barn

                                              Province of Siena / San Gimignano

                                              San Gimignano villa

                                              2 4 min stay varies

                                              • 2 bedrooms
                                              • sleeps 4
                                              • min stay varies
                                              • Nearest beach 70 mi
                                              • Swimming pool
                                              • Child Friendly

                                              Price per night from

                                              $150

                                              Price per night from

                                              $150

                                                30

                                                Rustica Progenie - Trilo b (4 + 2)

                                                San Gimignano / Pancole

                                                Pancole apartment

                                                2 6 min stay varies

                                                • 2 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Nearest beach 65 mi
                                                • Swimming pool
                                                • Child Friendly

                                                Price per night from

                                                $103

                                                Price per night from

                                                $103

                                                (4) Average 

                                                  7

                                                  Beautiful Hilltop 2-Story Farmhouse Apartment

                                                  Province of Siena / San Gimignano

                                                  San Gimignano apartment

                                                  1 5 1 night min

                                                  • 1 bedroom
                                                  • sleeps 5
                                                  • 1 night min
                                                  • Child Friendly
                                                  • Pet Friendly
                                                  “Excellent Trip” Well what a trip. Something I will cherish forever. The owner was extremely helpful and location was perfect. The home had an old school charm and was nice and clean. Everything was as promised and our honeymoon was definitely some

                                                  Price per night from

                                                  $90

                                                  Price per night from

                                                  $90

                                                  (9) Very Good 

                                                    19

                                                    Old Barn House

                                                    Province of Siena / San Gimignano

                                                    San Gimignano house

                                                    2 4 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Ask about children
                                                    • Ask about pets
                                                    “Beautiful secluded villa in a quiet and peacefull location” This was our second visit to this villa it met all our requirments and expectations it stands in its own grounds with nice gardens and a well maintained swimming pool,the rooms are clean and

                                                    Price per night from

                                                    $134

                                                    Price per night from

                                                    $134

                                                    (25) Excellent 

                                                      28

                                                      la Torretta Apartment

                                                      Province of Siena / San Gimignano

                                                      San Gimignano apartment

                                                      2 5 3 nights min

                                                      • 2 bedrooms
                                                      • sleeps 5
                                                      • 3 nights min
                                                      • Nearest beach 81 mi
                                                      • Child Friendly
                                                      • Car not necessary
                                                      “great stay!” We stayed in La Torretta in October of 2013 for 5 nights! It is a wonderful apartment and a great location! The owners were always close by if we had a question or needed help. We can't wait to go back!

                                                      Price per night from

                                                      $115

                                                      Responds fast!
                                                      avg. 1 hour 33 minutes

                                                      Price per night from

                                                      $115

                                                        9

                                                        3 bedroom Villa with Pool and WiFi - 5336627

                                                        Province of Siena / San Gimignano

                                                        San Gimignano villa

                                                        3 6 7 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Child Friendly
                                                        • Ask about pets

                                                        Price per night from

                                                        $266

                                                        Price per night from

                                                        $266

                                                        (6) Excellent 

                                                          12

                                                          Il Granaio 1 Bedroom Tuscan Farmhouse

                                                          Province of Siena / San Gimignano

                                                          San Gimignano house

                                                          1 2 7 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Ask about children
                                                          • Ask about pets
                                                          “Heaven in Tuscany” Our stay at the cottage of Il Granaio was like a slice of heaven. Wonderful location in the most beautiful setting. The owner Rosina is the most delightful lady, we loved her instantly. The property is clean, well appointed and t

                                                          Price per night from

                                                          $64

                                                          Price per night from

                                                          $64

                                                          (4) Excellent 

                                                            30

                                                            Apartment with spectacular views: Girasole

                                                            Province of Siena / San Gimignano

                                                            San Gimignano apartment

                                                            2 4 5 nights min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 5 nights min
                                                            • Nearest beach 90 mi
                                                            • Swimming pool
                                                            • Child Friendly
                                                            “Our best week in Italy!” We had the most amazing time staying at Maria's beautiful Tuscan house! It is beautifully presented and Maria's hospitality outstanding! We are a family of 2 adults & 2 children aged 10 & 11. The pool was a godsend at the end

                                                            Price per night from

                                                            $144

                                                            Price per night from

                                                            $144

                                                              19

                                                              2 bedroom Villa with Pool and WiFi - 5336572

                                                              Province of Siena / San Gimignano

                                                              San Gimignano villa

                                                              2 4 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Pet Friendly

                                                              Price per night from

                                                              $164

                                                              Price per night from

                                                              $164

                                                                35

                                                                4 bedroom Villa with Pool, Air Con and WiFi - 5650947

                                                                Province of Siena / San Gimignano

                                                                San Gimignano apartment

                                                                4 10 7 nights min

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $175

                                                                Price per night from

                                                                $175

                                                                  60

                                                                  Hilltop Escape for Families & Double-Date Couples

                                                                  Province of Siena / San Gimignano

                                                                  San Gimignano apartment

                                                                  2 7 4 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 7
                                                                  • 4 nights min
                                                                  • Nearest beach 81 mi
                                                                  • Child Friendly
                                                                  • Private garden

                                                                  Price per night from

                                                                  $79

                                                                  Responds fast!
                                                                  avg. 1 hour 13 minutes

                                                                  Price per night from

                                                                  $79

                                                                  (1) Excellent 

                                                                    16

                                                                    il pozzo

                                                                    Province of Siena / San Gimignano

                                                                    San Gimignano apartment

                                                                    1 2 3 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 3 nights min
                                                                    • Child Friendly
                                                                    • Pet Friendly

                                                                    Price per night from

                                                                    $130

                                                                    Price per night from

                                                                    $130

                                                                      37

                                                                      5 bedroom Villa with Pool, Air Con and WiFi - 5650949

                                                                      Province of Siena / San Gimignano

                                                                      San Gimignano apartment

                                                                      5 10 7 nights min

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $201

                                                                      Price per night from

                                                                      $201

                                                                        18

                                                                        4 bedroom Villa with Pool - 5336586

                                                                        Province of Siena / San Gimignano

                                                                        San Gimignano villa

                                                                        4 8 7 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 7 nights min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $248

                                                                        Price per night from

                                                                        $248

                                                                          15

                                                                          Villa La Ripa - Nidi

                                                                          Province of Siena / San Gimignano

                                                                          San Gimignano villa

                                                                          2 4 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $150

                                                                          Price per night from

                                                                          $150

                                                                            24

                                                                            Tenuta Le Sodole - Poppy Holiday Home

                                                                            San Gimignano / Pancole

                                                                            Pancole villa

                                                                            2 4 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $102

                                                                            Price per night from

                                                                            $102

                                                                            (10) Very Good 

                                                                              9

                                                                              One Bedroom Ground Floor Apartment San Gimignano

                                                                              Province of Siena / San Gimignano

                                                                              San Gimignano house

                                                                              1 2 7 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Ask about children
                                                                              • Ask about pets
                                                                              “When you really need to disconnect with the rest of the world...” A friendly and warm welcome from geniun tuscan people. The room was nice and clean and had all comfort, simple but that's all you need up there. The garden was well kept and the swimmi

                                                                              Price per night from

                                                                              $51

                                                                              Price per night from

                                                                              $51

                                                                              About San Gimignano

                                                                              Tuscany is home to many beautiful old towns and the historical town of San Gimignano is no exception. With its medieval architecture, vast vineyards, and hospitable locals, San Gimignano is an excellent introduction to the amazing country of Italy. Porto San Giovanni is considered to be the main street in town, but there are plenty of more hidden side streets that have unique restaurants and shopping options, so be sure to explore the entire downtown.

                                                                              As you stroll, check out some of these top destinations:

                                                                              • Piazza del Duomo: This main square in the town is surrounded by towers which are over 1,000 years old.
                                                                              • Torre Grossa: At over 200 feet tall, this is the tallest tower in the city.
                                                                              • Rocca: This rock offers an amazing panorama of the Tuscan countryside from the top.
                                                                              • The Collegiata: The main cathedral in the city, this beautiful attraction has a series of frescoes on Old and New Testament subjects.
                                                                              • Piazza della Cisterna: This beautiful piazza is home to a market every Thursday.
                                                                              • San Gimignano 1300: Located right in the middle of the town, this museum features a large reconstruction of San Gimignano.

                                                                              Despite being somewhat small, San Gimignano has an impressive number of events and festivals held year-round. Some of them include the San Gimignano Musica, a series of classical music concerts held in September and October; the Archaeological Summer Camp, excavations at Castelvecchio held every August; and the Medieval Harvest Festival, a series of events every March that include a blessing of the knights, historical parade, and medieval games.

                                                                              A vacation rental is the preferred option for those staying in San Gimignano. With homes ranging from villas overlooking the beautiful architecture and vineyards in the area, to spacious and luxurious condos in the heart of town, there's sure to be a property available that's right for you.