Sassicaia Wine Area Vacation Rentals from ￥8,284: Search Short-Term Rentals

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Our top choices for Sassicaia Wine Area vacation rentals

1. Casa Ede: Relaxation in a Tuscan village nestled between the beaches and vineyards of Bolgheri

Bibbona

￥16,485 total

includes taxes & fees

Nov 12 - Nov 13

A hotel room with a bed, a chair, a bedside table, and a window with curtains.

2. Il Vicolo Spacious Room in the Village – Experience Village Charm with Style

Castagneto Carducci

￥23,443 total

includes taxes & fees

Nov 12 - Nov 13

A four-poster bed with white linens, a desk with a chair, and a patterned floor.

3. Camera Il Paese with Double Panoramic View – Stay in the Village with Charm

Castagneto Carducci

￥23,443 total

includes taxes & fees

Nov 12 - Nov 13

An aerial view of a property with a swimming pool, multiple buildings, and well-maintained gardens.

4. Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning

Bibbona

￥34,214 total

includes taxes & fees

Nov 15 - Nov 16

5. Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning

Bibbona

Michael W.

￥34,992 total

includes taxes & fees

Nov 15 - Nov 16

6. Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning

Bibbona

￥33,436 total

includes taxes & fees

Nov 15 - Nov 16

7. Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning

Bibbona

￥34,214 total

includes taxes & fees

Nov 15 - Nov 16

A reception area with a stone wall, framed pictures, and a view of a swimming pool through a large window.

8. Residenza Santa Cecilia

San Vincenzo

jeffrey

￥11,973 total

includes taxes & fees

Dec 9 - Dec 10

A modern living room with a sofa, a wooden table, and a dining area with white chairs. There are hanging lights and a view of greenery outside.

9. Borgo Verde

Rosignano Marittimo

Laura

￥9,112 total

includes taxes & fees

Nov 14 - Nov 15

A compact kitchen with a dining area, featuring a round table, chairs, a built-in oven, and a TV mounted on the wall.

10. Cav Costa degli Etruschi

San Vincenzo

Eduardo

￥12,323 total

includes taxes & fees

Nov 12 - Nov 13

A restaurant with white wooden tables and chairs, hanging light bulbs, and green vines.

11. Hotiday Relais Costa degli Etruschi

Rosignano Marittimo

Ant

￥9,300 total

includes taxes & fees

Nov 22 - Nov 23

A building with a stucco exterior, multiple windows, and a tiled roof.

12. Residence Il Paradiso

Guardistallo

Jason

￥18,554 total

includes taxes & fees

Nov 14 - Nov 15

A dining area with a stone wall, wooden chairs, a table set with plates, glasses, and a fruit bowl.

13. Beatabb

Guardistallo

Joanne

￥12,426 total

includes taxes & fees

Dec 12 - Dec 13

14. Via Siena 4 - Suites & Rooms

Cecina

￥10,448 total

includes taxes & fees

Nov 30 - Dec 1

A beach with clear blue water and a sandy shore.

15. Studio apartment 50 meters from the beach.

San Vincenzo

Thomas E.

￥23,222 total

includes taxes & fees

Nov 16 - Nov 17

An aerial view of a coastal town with a marina, sandy beaches, and residential buildings.

16. Three-bedroom apartment 50 meters from the beach.

San Vincenzo

Luana

￥30,844 total

includes taxes & fees

Nov 15 - Nov 16

A rooftop swimming pool with a view of the sea and hills during sunset.

17. La Rosa dei Venti Resort

Piombino

Mike

￥20,554 total

includes taxes & fees

Nov 18 - Nov 19

A stone building with arches, surrounded by lush greenery and hills.

18. Caravan 'Volpe Rossa' with Shared Garden and Air Conditioning

Suvereto

Anonymous traveler

￥20,167 total

includes taxes & fees

Nov 12 - Nov 13

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and a building with large windows.

19. San Francesco Country Resort

Rosignano Marittimo

PIETRO

￥13,148 total

includes taxes & fees

Nov 17 - Nov 18

An open dining area with a table set for two, a red sofa, and a painting on the wall.

20. La Ripadoro

Chianni

Maya

￥30,171 total

includes taxes & fees

Nov 16 - Nov 17

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Find vacation rentals that suit your style

Top Sassicaia Wine Area Hotel Reviews

A spa area with a hot tub surrounded by columns and a seating area with umbrellas.

Castello Bonaria Wine & Spa Resort

Campiglia Marittima

10/10 Excellent

Andrew

Residenza Santa Cecilia

San Vincenzo

10/10 Excellent

This is a gem! We got a two room sea view suite and a one room suite. Both were huge with huge porches looking out for the ocean! We could have relaxed in our rooms for hours. We swam in the pool every night! And we did the breakfast every morning. The pool was so fun and the breakfast was incredible (coffee, cakes, croissants, yogurt, eggs and bacon and more). We needed it to recover from our jet lag and it went until 11am so we could really relax and have all three cups of coffee...

Kathleen

Borgo Verde

Rosignano Marittimo

10/10 Excellent

Laura

A lush outdoor setting with a pergola, olive trees, and a distant hill with a structure.

Relais dei Molini

Castagneto Carducci

10/10 Excellent

This is an exceptional property. The grounds and rooms are top notch. Clean and modern. The location is perfect. Close to the village and with a superb view. Breakfast was cooked to your own preferences. Fresh cakes were also served. The owner, Luca, helped us with dinner recommendations and reservations. Also, during our stay we had a mechanical issue with our rental car. Luca helped us in finding a garage for the repair. All in all I highly recommend this property.

Mark

A pool area with lounge chairs, umbrellas, and a rock feature.

Relais San Baio

Cecina

10/10 Excellent

Salvatore

An indoor pool with a natural rock backdrop, surrounded by lounge chairs and a stone pathway.

Tombolo Talasso & Beach Resort

Castagneto Carducci

10/10 Excellent

Melanie

A stone building with a statue of a seated figure, potted plants, and a cobblestone street.

Le Dame del Borgo

Sassetta

10/10 Excellent

Nigel

A large indoor swimming pool with a hot tub, surrounded by a glass-enclosed area with a view of the outdoors.

Hotel delle Terme

Campiglia Marittima

10/10 Excellent

Everyone in the hotel was very accommodating. The front staff spoke a little English and enough to get us checked in and feel comfortable. Most staff spoke only Italian or Spanish, but that is understandable. It felt like a resort such that we were in the middle of coutry-side a d close to the beach within 10 miles. They had a HUGE pool and attendants making sure the site was clean, maintained, and secure. Very happy about their breakfast options and dinner selections. We did mostly eat out...

Daniel

An outdoor patio with wicker furniture, a stone staircase, and a view of a historic building in the background.

Albergo Etruria

Volterra

10/10 Excellent

Steve

A poolside area with lounge chairs and umbrellas, a clear blue pool, and a brick pathway.

Tenuta La Lupa Country Hotel

Castellina Marittima

10/10 Excellent

Jenny

A rustic wine cellar with wooden shelves, hanging lights, and a stone wall.

Punti Di Vista B&B Food&Wine Experience

Bibbona

10/10 Excellent

We had an awesome stay at the hotel. The atmosphere was cozy and stylish, and everything was just right. The restaurant really stood out, especially with its amazing food and wine selection—there’s something for everyone, and the choices are seriously impressive. The staff made the experience even better; they were super friendly, helpful, and always on top of things. If you’re after great hospitality and a fantastic meal, this place is definitely worth checking out.

Stephen

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Vacation Apartments in Sassicaia Wine Area

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Lodging

Sassicaia Wine Area Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sassicaia Wine Area vacation rentals

1. Casa Ede: Relaxation in a Tuscan village nestled between the beaches and vineyards of Bolgheri

2. Il Vicolo Spacious Room in the Village – Experience Village Charm with Style

3. Camera Il Paese with Double Panoramic View – Stay in the Village with Charm

4. Bungalow 'Sole2' with Shared Pool, Private Terrace and Air Conditioning

5. Bungalow 'Stella 1' with Shared Pool, Private Terrace and Air Conditioning

6. Bungalow 'Stella 2' with Shared Pool, Private Terrace and Air Conditioning

7. Bungalow 'Sole1' with Shared Pool, Private Terrace and Air Conditioning

8. Residenza Santa Cecilia

9. Borgo Verde

10. Cav Costa degli Etruschi

11. Hotiday Relais Costa degli Etruschi

12. Residence Il Paradiso

13. Beatabb

14. Via Siena 4 - Suites & Rooms

15. Studio apartment 50 meters from the beach.

16. Three-bedroom apartment 50 meters from the beach.

17. La Rosa dei Venti Resort

18. Caravan 'Volpe Rossa' with Shared Garden and Air Conditioning

19. San Francesco Country Resort

20. La Ripadoro

Find vacation rentals that suit your style

Top Sassicaia Wine Area Hotel Reviews

Castello Bonaria Wine & Spa Resort

10/10 Excellent

Find out more about Sassicaia Wine Area

Vacation Apartments in Sassicaia Wine Area

Explore a world of travel with Expedia