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Kissimmee

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268 Holiday homes

Filters applied: Cot available

(3) Excellent 

100

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 5 nights min

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool

from £290 / night

£2030 / week

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from £290 / night

(48) Excellent 

21

Holiday villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic!” We Stayed at Doral Woods villa in May 16. The villa is equipped with everything you need and is spotlessly clean. Beautiful pool & garden the best villa we have ever stayed in! Highly recommend also the owners are so helpful and attentive
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from £130 / night

£895 - £995 / week

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Responds fast!
avg. 2 hours 24 minutes

from £130 / night

(5) Very Good 

74

Villa rental in Kissimmee with swimming pool, golf nearby

Kissimmee / Windsor Hills Resort

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Lovely villa” Very good if you are visiting Disney parks they are very close by. The villa was in a very nice neighbourhood also it was well maintained. Also the security gates made us feel very secure. Slightly further away from International D
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from £108 / night

£750 / week

Enquire View

from £108 / night

(30) Excellent 

Certificate of Excellence

21

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Mrs” Just back from a 2 week stay at this villa. It is one of the best we have stayed in. Perfect location, near lots of our favourite restaurants, disney etc. The pool gets sun all day and has loads of outdoor space. The pool and Jacuzzi heat actuall
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Certificate of Excellence

from £83 / night

£575 - £625 / week

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Responds fast!
avg. 1 hour 18 minutes

from £83 / night

(10) Very Good 

20

Holiday townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £95 / night

£575 - £900 / week

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from £95 / night

(15) Excellent 

Certificate of Excellence

12

Kissimmee holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £84 / night

£550 - £700 / week

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from £84 / night

(1) Excellent 

24

Lake Berkley holiday villa rental

Kissimmee / Lake Berkley

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £123 / night

£860 / week

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from £123 / night

(4) Excellent 

24

Villa rental in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful property!” Our host Lisa Ellis made us feel welcome since before booking. I had a couple of questions when searching for the perfect place to stay and she answered them very quickly. Once I booked we stayed in constant communication which ma
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from £104 / night

£675 - £925 / week

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from £104 / night

(6) Very Good 

13

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £150 / night

£700 - £800 / week

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Responds fast!
avg. 1 hour 59 minutes

from £150 / night

(9) Very Good 

26

Kissimmee holiday villa rental

Central Florida / Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great Disney Vacation” The house was great but does need some repairs. The ironing board could not be used the leg was broken in half. The living room furniture is very worn and needs to be replaced and when my husband went to open the refrigerator d
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from £72 / night

£501 / week

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from £72 / night

(5) Very Good 

74

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £125 / night

£949 - £1108 / week

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Responds fast!
avg. 3 hours 58 minutes

from £125 / night

(24) Excellent 

Certificate of Excellence

59

Holiday townhouse with shared pool in Trafalgar Village

Kissimmee / Trafalgar Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“excellent” my wife and two friends stayed here in may for 10 days. one word excellent. the house is only about 25 mins from all the parks. the location is incredibly quiet with onsite security. 3 bedrooms + 3bathrooms a large living area gives plenty
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Certificate of Excellence

from £45 / night

£360 - £840 / week

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Responds fast!
avg. 2 hours 39 minutes

from £45 / night

(1) Excellent 

52

Holiday villa in Eagle Pointe

Kissimmee / Eagle Pointe

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool

from £118 / night

£707 - £978 / week

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Responds fast!
avg. 2 hours 41 minutes

from £118 / night

85

Holiday villa with swimming pool in Kissimmee

Kissimmee / Sunset Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £95 / night

£665 - £1000 / week

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Responds fast!
avg. 1 hour 22 minutes

from £95 / night

(14) Excellent 

23

Kissimmee holiday home rental

Kissimmee / Windsor Palms

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic Villa, Perfect Location for Disney etc., Food & Shopping” It was a very straightforward process booking 'Mickey's Clubhouse', questions were answered very promptly by the owners - the whole process was quick, efficient and informative.The vi
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from £115 / night

£875 / week

Enquire View

from £115 / night

(19) Very Good 

27

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Geat location” Stayed 23.8.16 to 6.9.16. Great home for 9 people that stayed. Home was clean and well kept. A 10 minute drive to Disney and 20 minutes to Universal and Sea World. Great that there were plenty of extra towels in the cupboard. Washi
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from £143 / night

£1000 - £1300 / week

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Responds fast!
avg. 3 hours 25 minutes

from £143 / night

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £96 / night

£667 / week

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from £96 / night

(23) Excellent 

Certificate of Excellence

56

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool
“Gorgeous villa !” Our first visit to Florida and we had an amazing time i really can't see us going any where else.. the villa is beautiful I felt like a queen for two weeks :) everything u need and more the location is so peaceful, perfect for relaxi
…see more

Certificate of Excellence

from £107 / night

£750 - £900 / week

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Responds fast!
avg. 1 hour 42 minutes

from £107 / night

(8) Excellent 

24

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Honeymoon” Brilliant can't fault it at all, everything you need to hand, recommend this villa plenty of space great
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from £75 / night

£485 / week

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Responds fast!
avg. 1 hour 39 minutes

from £75 / night

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Harbor

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £119 / night

£985 - £1142 / week

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from £119 / night

(10) Very Good 

50

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa” Was very impressed with the villa. Very spacious and clean. Lots of local amenities and all parks very close by. Situated on a quiet estate and very welcoming would definitely recommend
…see more

from £85 / night

£520 - £550 / week

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from £85 / night

(32) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Best Florida Villa - by far !!!” We have spent many many weeks at this villa and when it isn't available for our trips to Florida nothing we stay at compares !!! It is a great villa, owned by an owner who cares. Well equipped, south facing, very pri
…see more

from £135 / night

£800 - £995 / week

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Responds fast!
avg. 3 hours 26 minutes

from £135 / night

(11) Very Good 

75

Holiday villa with shared pool in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 107 km
  • Swimming pool
“Fantastic Relaxing Retreat from the Orlando Hustle and Bustle” We very much enjoyed our stay in this spacious and secure house. It is situated in a safe and quiet gated community less than half an hour's drive from most of the Orlando theme parks and
…see more

from £115 / night

£800 / week

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from £115 / night

(7) Excellent 

48

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Exceeded Expectations” We just got back (May 2013) from a stay at Emerald Magic 6 bedroom villa at Emerald Island Resorts and had a wonderful stay. The house was even better then expected when we arrived. Nice welcoming touches everywhere. Lots of tow
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from £186 / night

£1339 - £1812 / week

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Responds fast!
avg. 52 minutes

from £186 / night

(3) Very Good 

Certificate of Excellence

34

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £90 / night

£624 / week

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from £90 / night

(13) Very Good 

14

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great place to stay” Great place to stay, it's a lot bigger than it looks on the photos. The pool is lovely with sun on it from early morning till evening in July. The beds are comfortable, loads of towels available, the BBQ, fridge freezer,microwave
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from £65 / night

£450 - £500 / week

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from £65 / night

(2) Excellent 

70

Holiday villa letting

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool

from £95 / night

£665 - £875 / week

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from £95 / night

(40) Excellent 

39

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Holiday To Remember” A perfect exciting, fantastic holiday with all the family. Family of 6. In the last week 7.Quality time with everyone.Extremely a special and magical holiday to remember.The villa was fabulous and very homely.Perfect from start t
…see more

from £85 / night

£505 - £515 / week

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Responds fast!
avg. 45 minutes

from £85 / night

(10) Excellent 

14

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“A HOLIDAY TO REMEMBER” Cumbrian lakes drive is a well appointed 8 bed villa in very pleasant surroundings. We stayed there 4 adults and 2 young children aged 6 & 8 for 2 weeks. It is within easy access of all the parks, the malls etc and only a shor
…see more

from £90 / night

£630 - £795 / week

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from £90 / night

(5) Excellent 

27

Holiday villa letting

Kissimmee / Windsor Palms

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £120 / night

£825 / week

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from £120 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.
…see more

from £130 / night

£840 - £1450 / week

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from £130 / night

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,
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from £158 / night

£1106 / week

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Responds fast!
avg. 3 hours 38 minutes

from £158 / night

(17) Excellent 

Certificate of Excellence

19

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Lots of space and nice pool” We travelled with two children (9&10) plus two teenagers and everybody enjoyed our stay! Plenty of room for everybody, own swimming pool and jaguzzi plus communal pool. Short (15-20 min) drive to the amusement parks. Sever
…see more

Certificate of Excellence

from £90 / night

£590 / week

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Responds fast!
avg. 2 hours 13 minutes

from £90 / night

(21) Very Good 

17

Holiday villa in Kissimmee City

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Magnificent Accomadation” We arrived for our stay of 2 weeks after travelling for 20 hours, we found the place easily everything was as described, the only disappointment my girls had was the pool was cold , however it soon warmed up after a couple o
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from £65 / night

£345 - £695 / week

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Responds fast!
avg. 3 hours 6 minutes

from £65 / night

(70) Excellent 

27

Villa rental in Kissimmee

Kissimmee / Windsor Palms

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £185 / night

£1290 - £1743 / week

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from £185 / night

(4) Excellent 

17

Holiday home with golf nearby in Kissimmee

Kissimmee / Terra Verde Resort

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
“Golf vacation in beautiful surroundings” Terre Verde Resort is a beautiful resort with a luxurious club house with all amenities, pool, pool-bar, fitness center surrounding i relatively large pond. Nice playground. Short distance (15 min) to Disney a
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from £70 / night

£490 / week

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from £70 / night

(30) Very Good 

12

Villa rental in Lindfields with swimming pool

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Villa” This villa is just perfect! Beautifully furnished and has everything you could possibly need for your stay. Kathryn the owner is great, if you have any questions etc....It is situated in a very quiet cup- de-sac and ver secure. The pr
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from £61 / night

£425 - £665 / week

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from £61 / night

(10) Excellent 

Certificate of Excellence

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

Certificate of Excellence

from £125 / night

£875 - £1073 / week

Book View

from £125 / night

(4) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Remington

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
“Great vacation” We had a great holiday . The villa is lovely and very spacious. All home comforts and more. There were 7 of us and we had plenty of room (could comfortably sleep 10). The location is ideal for parks and shopping malls with just a short
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from £75 / night

£525 - £910 / week

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from £75 / night

23

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

from £239 / night

£1112 - £2135 / week

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from £239 / night

1