Villas with a pool Siena | Apartments to rent with swimming facilities | Holiday Lettings

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  • Italy
  • Tuscany
  • Province of Siena
  • Siena
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  • Badia A Elmi (2)
  • Caprera (2)
  • Gracciano di Colle Val d'Elsa (5)
  • Iesa (7)
  • Isola d'Arbia (4)
  • Sant Andrea a Montecchio (2)
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  • Val di Merse (1)

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233 Holiday homes

Filters applied: Swimming pool (233)

Travellers going to Siena are booking October dates now. Secure your holiday home today and have the perfect trip.

17

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 83 km
  • Swimming pool
  • Child friendly

 …see more

from £82 / night

£423 - £983 / week

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from £82 / night

(1) Very Good 

21

Province of Siena / Siena

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Air conditioning

 …see more

from £138 / night

£960 / week

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from £138 / night

16

Siena / Sant Andrea a Montecchio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £61 / night

£423 / week

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from £61 / night

24

FRANTOIO - Siena farmhouse sleeps 6

Province of Siena / Siena

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £117 / night

£815 / week

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from £117 / night

(3) Very Good 

15

Apartment in Tuscan cottage in Siena, lovely swimming poool and garden space - Siena house sleeps 3

Province of Siena / Siena

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The apartment is part of a family cottage. Outside you can enjoy a large garden, a swimming pool, with the use of sun beds and sun umbrellas, outdoor table suitable for outdoor dining and barbecue. We offer additional services such as parking, washing machine, stove, re  …see more

from £65 / night

£432 / week

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from £65 / night

(3) Excellent 

22

Beautiful tuscan Villa not far from Siena 18 pax - Siena villa sleeps 18

Province of Siena / Siena

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £345 / night

£1983 - £3449 / week

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from £345 / night

(1) Excellent 

24

Restored Barn - country home - Siena barn sleeps 3

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Splendid 18th century mansion with typical Sienese architecture. It is situated next to the historical village of Basciano. The house position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena.  …see more

from £95 / night

£569 - £725 / week

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from £95 / night

(2) Excellent 

40

Siena / Val di Merse

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £108 / night

£768 - £1707 / week

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from £108 / night

(42) Excellent 

35

Beautiful Private Villa, pool, hot tub,wi-fi,Siena - Siena villa sleeps 12

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
JUST RELAX...... YOUR VACATION IN TUSCANY BEGINS NOW!!!! What we want is to make this holiday as pleasant and relaxing as possible, so we want to make available to you our Villa, that for a time, long or short it might be, will be YOUR HOME in Tuscany. A HOLIDAY WITHOUT  …see more

from £241 / night

£1682 - £4311 / week

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from £241 / night

(3) Excellent 

18

Apartment Camilla, countryside, not far from Siena - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £78 / night

£518 - £949 / week

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from £78 / night

22

Villa Gaiole - Siena villa sleeps 13

Province of Siena / Siena

5 13 2 nights min

  • 5 bedrooms
  • Sleeps 13
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located between Florence and Siena in Chianti, Villa Gaiole's private hilltop position provides 360 degree panoramic views of the breathtaking Tuscan countryside. Set around an expansive central courtyard with barbeque area, this luxury villa rental provides visito  …see more

from £2561 / night

£8534 - £11378 / week

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from £2561 / night

27

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £179 / night

£1250 - £1682 / week

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from £179 / night

100

Villa Gardenia - Siena apartment sleeps 3

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
These 7 superior rooms in Tuscany are very spacious and boast the typical Tuscan décor. They can accommodate up to 2 people each and they all afford comfortable beds, private and large bathrooms, television and telephone, among other amenities. Some of them offer  …see more

from £86 / night

£598 - £1020 / week

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from £86 / night

100

Villa Gardenia - Monolocale - Siena apartment sleeps 3

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Each of these one-room apartments can accommodate up to 2 people. They both afford a comfortable bed, a private and fully equipped bathroom, a kitchenette and all the comforts. In one of them it is possible to add an extra bed upon request.The wooden beams on the ceilin  …see more

from £77 / night

£538 - £869 / week

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from £77 / night

22

SERRA - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
APARTMENTS AND HOLIDAY HOUSES IN SIENA IN TUSCANYVilla Agostoli is a residential complex of apartments for holidays in Siena in Tuscany. The holiday houses of Villa Agostoli are located in the countryside right outside Siena and they are so close to the city that they c  …see more

from £87 / night

£604 / week

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from £87 / night

(3) Excellent 

22

SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO - Siena villa sleeps 5

Province of Siena / Siena

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
La villa (5 posti letto ) è situata nella campagna di Siena a circa 15 minuti a piedi dalla famosa 'Piazza del Campo' di Siena. Si trova in cima ad una collina, corredata di piscina e campo da tennis, offre splendidi panorami sulla città e sulla campagna cir  …see more

from £255 / night

£992 - £1725 / week

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from £255 / night

20

Province of Siena / Siena

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

 …see more

from £87 / night

£604 / week

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from £87 / night

(3) Very Good 

26

Apartment in Historic Farmhouse with pool - Siena apartment sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The apartment (80m2) is on two floors. The entrance is on the ground floor through a glassdoor. The main room include a living area with a double sofa bed, a fully equipped kitchen and dining table, all renewed on January 2014. The bathroom is equipped with shower cabin  …see more

from £95 / night

£569 - £690 / week

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from £95 / night

(2) Excellent 

24

Stunning Villa in Siena with exclusive spa - Siena villa sleeps 10

Province of Siena / Siena

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful villa in Siena with private Spa-Wellness Center room is situated on the hills with a breathtaking view over the vineyards up to Siena. An ideal accommodation for all those seeking peace and quiet but also a perfect point of departure for visiting the beau  …see more

from £234 / night

£1638 - £3447 / week

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from £234 / night

100

Villa Gardenia - 2 pax - Siena apartment sleeps 2

Province of Siena / Siena

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
This apartment for two affords a bedroom, a kitchenette and a fully equipped bathroom.It is located on the second floor; and its wooden beams on the ceiling and the soft colours create a very lovely and cozy atmosphere. This apartment for two is perfect for a romantic s  …see more

from £82 / night

£568 - £900 / week

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from £82 / night

9

Province of Siena / Siena

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £113 / night

£561 / week

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from £113 / night

10

Province of Siena / Siena

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

 …see more

from £493 / night

£3449 / week

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from £493 / night

36

Beautiful Tuscan Villa not far from Siena 22 pax - Siena villa sleeps 22

Province of Siena / Siena

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £475 / night

£2587 - £4311 / week

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from £475 / night

(4) Excellent 

18

Province of Siena / Siena

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Private garden

 …see more

from £44 / night

£302 / week

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from £44 / night

(1) Excellent 

39

Bright, spacious villa with pool near Siena - Siena villa sleeps 7

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Key points: large apartment (140 m2) in a farmhouse renovated with taste and attention to details. Terrace and independent entrance into the courtyard of the property, large pool with view and garden-park with olive grove. Fully equipped kitchen, comfortable living room  …see more

from £156 / night

£845 - £1302 / week

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from £156 / night

100

Villa Gardenia - 4 pax - Siena apartment sleeps 4

Province of Siena / Siena

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
These two comfortable apartments can accommodate up to 4 people each. One of them affords a double bed and two single beds, and the second one has two double beds. They both boast their own living area and kitchenette and a private and fully equipped bathroom.They are b  …see more

from £125 / night

£869 - £1171 / week

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from £125 / night

20

Casa Felice - Siena farmhouse sleeps 22

Province of Siena / Siena

11 22 2 nights min

  • 11 bedrooms
  • Sleeps 22
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Casa Felice is an outstanding Tuscan farmhouse with 11 bedrooms and 11 bathrooms.It was recently renovated and brought back to its original splendour. Casa Felice is situated on a small road that leads to a wonderful medieval hamlet of Montebenichi.The villa is filled w  …see more

from £1352 / night

£5406 - £5822 / week

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from £1352 / night

100

Villa Gardenia - 3 pax - Siena apartment sleeps 4

Province of Siena / Siena

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
Each of these three apartments for 3 affords comfortable beds, a living area and kitchenette, and bathroom; two of them feature a balcony and there is the possibility to add extra beds.Two of them are located on the first floor, and the third one is on the second f  …see more

from £107 / night

£749 - £1063 / week

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from £107 / night

24

23916-Holiday house San Gimign - Badia A Elmi villa sleeps 8

Siena / Badia A Elmi

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The property is a beautiful detached villa converted from a lovely, old hay store situated in the Chianti hills half way (35 km) between Florence and Siena. In the well kept garden there is an inviting swimming pool (8 x 5 m) available from May to October opening onto  …see more

from £94 / night

£652 - £1410 / week

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from £94 / night

(7) Excellent 

31

Province of Siena / Siena

2 3 1 night min

  • 2 bedrooms
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Pet friendly

 …see more

from £104 / night

£725 - £992 / week

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from £104 / night

22

Province of Siena / Siena

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning

 …see more

from £86 / night

£598 / week

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from £86 / night

18

BELLAVALLE - Siena villa sleeps 10

Province of Siena / Siena

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
An eighteenth century Tuscan farmhouse in a delightful little valley along the historic Via Francigena, surrounded by 14 hectares of privately owned vines, olive trees and woods that ensure utter privacy and tranquillity – this is Bellavalle, just 3.5 kilometres from  …see more

from £850 / night

£3535 - £5949 / week

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from £850 / night

24

Siena / Sant Andrea a Montecchio

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £92 / night

£557 - £609 / week

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from £92 / night

24

Tenuta Val d'Elsa - Siena villa sleeps 35

Province of Siena / Siena

18 35 7 nights min

  • 18 bedrooms
  • Sleeps 35
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Total Luxury - Italy special occasion villa with services - this magnificent 14th century estate is situated in the heart of rural Tuscany between San Gimignano and Siena. The villa's hilltop position offers wonderful 360 degree views of the surrounding countryside  …see more

from £4526 / night

£31680 - £45500 / week

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from £4526 / night

100

Villa Gardenia - Classic Room - Siena apartment sleeps 3

Province of Siena / Siena

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
These 4 classic rooms boast the typical Tuscan décor. They can accommodate up to 2 people each and they all afford comfortable beds, private and fully equipped bathrooms, television and telephone, among other amenities. Some of them offer an extra bed upon reques  …see more

from £77 / night

£538 - £960 / week

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from £77 / night

25

Apartment GAIA, countryside, not far from Siena - Siena apartment sleeps 10

Province of Siena / Siena

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 95 km
  • Swimming pool
  • Child friendly
Podere Incrociati rises in the heart of Montagnola Senese, just 15 km/9 miles far from Siena and 75 km/47,5 miles far from Florence, among the greenery of age-old oaks, holm-oaks and chestnut-trees. Thanks to its high position (500 mt./1640 ft. above sea level) you will  …see more

from £207 / night

£1207 - £1983 / week

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from £207 / night

18

Apartment Cocchieri 101 - Caprera apartment sleeps 6

Siena / Caprera

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Recently renovated apartment over two floors, situated on top of the old riding stables, comfortably equipped and elegantly furnished with antique pieces of furniture. Main floor: living room/dining room, kitchen, 1 double room with a double bed, 1 double room, bathroom  …see more

from £233 / night

£807 - £897 / week

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from £233 / night

24

Villa La Strega luxury 6 bedroom villa in Tuscany - Siena villa sleeps 11

Province of Siena / Siena

6 11 Min stay varies

  • 6 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
This is a stunning eighteenth century villa situated on a hill just 2 kilometres from Siena and enjoying stunning views of the city. With a lovely terrace and informal private outdoor pool overlooking Siena, it's a great setting to enjoy a holiday with family and friend  …see more

from £370 / night

£2587 - £3880 / week

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from £370 / night

100

Villa Gardenia - 6+1 pax - Siena apartment sleeps 7

Province of Siena / Siena

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly
This large two-storey apartment can accommodate up to 7 people. It affords a living area and kitchenette, and a double room with en-suite bathroom on the ground floor; and two rooms with two bathrooms on the first floor.This large apartment is just perfect to accommodat  …see more

from £159 / night

£1111 - £1382 / week

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from £159 / night

100

Le Fate - Siena villa sleeps 12

Province of Siena / Siena

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Exterior Villa Le Fate is a distinguished villa situated in the Sienese countryside, just 3 km (1.8 miles) from Siena, and immersed in the exquisite landscape of vines and olive groves. The villa is an old seventeenth century manor house which has recently been complete  …see more

from £261 / night

£1827 - £3653 / week

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from £261 / night

Top Destination reviews

La Stalla di San Lazzero, adorable house in Siena
What a wonderful stay! We highly recommend this house!

We instinctively felt in love with Leonardo's house the moment we arrived! The description we received from Leonardo how to get to the house was perfect and we immediately found the correct way (thank you!). Leonardo greeted us warmly and showed u … see more
Private, elegant zen cottage, 10 min. from Siena
Peaceful cottage in isolated location

Property although in an isolated location was fairly central for accessing all of the Tuscany region. All points requiring access were never any more than 1 hours drive away. Great base for touring. Property has no air conditioning therefore reli … see more

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