Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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3,504 Holiday homes

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(8) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
The Trafalgar Village community is centred around the luxurious Trafalgar Village Center (or Clubhouse), a 2 minute stroll from the property with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat mov  …see more

from £65 / night

£441 - £686 / week

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from £65 / night

(19) Very Good 

66

Holiday home rental

Kissimmee / Lindfields

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“Great accommodation” Stayed here for two weeks for our honeymoon. Location of the villa is excellent if visiting the Disney Parks. Clean and tidy, very large living area and bedrooms. Couldn't have asked for anything better.  …see more

from £50 / night

£350 / week

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from £50 / night

(5) Excellent 

18

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
3 Bed Villa Private South Facing Pool 15 Minutes from Disney.  …see more

from £60 / night

£425 - £650 / week

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from £60 / night

(2) Very Good 

20

Kissimmee holiday townhouse accommodation

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
First floor consists of 892 sf with hallway, bathroom, king size bedroom, living room with dining area and a luxurious kitchen. Second floor has 888 sf including 3 bedrooms, 2 full bathrooms, washroom with washer and dryer and closet in the hallway for linens. The patio  …see more

from £79 / night

£512 - £882 / week

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from £79 / night

(8) Very Good 

60

Holiday villa in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“beautiful” the house is beautiful and quiet, we had a great time and will definitely return, Kevin and Anne and their management are friendly and always available. thanks for everything  …see more

from £100 / night

£600 - £1200 / week

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from £100 / night

(9) 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 £94 / night

£658 / week

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from £94 / night

(2) Excellent 

61

Holiday home in USA East Coast

Kissimmee / Venetian Bay Villages

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Why stay in a hotel when you can have all the comforts of your own home away from home in our beautiful new townhome in a dream location, close to the theme parks and the attractions of Orlando and Central Florida.Our home is clean, comfortable and just where you ne  …see more

from £60 / night

£385 / week

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from £60 / night

52

Holiday villa in USA East Coast

Kissimmee / Eagle Pointe

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool
The house is all on one level and has two large separate living/dining areas, a games room and a large pool.  …see more

from £105 / night

£633 - £765 / week

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from £105 / night

(18) Very Good 

19

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent value, good facilities, close to the Disney Parks” The accommodation was excellent value for money. It was more than spacious enough for 2 adults and 2 children, and had good facilities (although it lacked wi-fi, which was sorely missed by s  …see more

from £71 / night

£520 - £678 / week

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from £71 / night

(6) Excellent 

27

USA East Coast 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
STUNNING 5 ***** LAKE VIEW ORLANDO VILLA Guests can relax and really enjoy this amazingly tranquil and peaceful setting EXCEPTIONAL LOCATION IN UNIQUE NATURAL CONSERVATION AREA WONDERFUL LAKE FRONT SPOT ..... SO PEACEFUL YET STILL CLOSE TO ALL THE AREA'S MAIN ATTR  …see more

from £115 / night

£799 - £1090 / week

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from £115 / 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
5 Bedroom, 4 bathroom, large pool, hot tub, games room, pc with wi-fi internet, cable tv, full kitchen and laundry facilities, free world wide phone calls, close to Disney parksClose to all Disney parks & also Universal, Seaworld and other parks, 1 Mile from Hwy 192, Qu  …see more

from £124 / night

£863 - £1099 / week

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from £124 / night

15

Holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
An ideal location for easy access to all of the attractions in a quiet neighbourhood with good privacy.  …see more

from £126 / night

£890 - £1134 / week

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from £126 / night

(4) Very Good 

18

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Amazing all the way around” My wife and I booked this Villa in order to have a nice place to relax after taking our three daughters to the Disney parks. We stayed for a week and mid way through each day we spent at the parks our kids would express how  …see more

from £90 / night

£575 - £775 / week

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from £90 / night

(5) Excellent 

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Pete and Louise” I felt like I was at home !!!!! Everything I needed and could have forgotten was already there......this place was immaculate! It was close tho so many things to do and shopping as well......I will be back again real soon for sure, th  …see more

from £50 / night

£303 - £325 / week

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from £50 / night

(5) Excellent 

55

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Windsor Hills is located in Kissimmee just 2 miles (3km) from the gates of Walt Disney World.  …see more

from £178 / night

£1241 / week

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from £178 / night

(2) Very Good 

20

Holiday condo in USA East Coast

Kissimmee / Legacy Dunes Resort

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Great Resort Very near Disney on the 192  …see more

from £77 / night

£539 - £686 / week

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from £77 / night

(17) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great holiday from start to finish.....” We arrived at the house worn out from travelling and opened the front door and it looked even better than the pictures. everything was perfect, it is basically home from home. Sara and Peter have thought of it  …see more

from £99 / night

£695 - £795 / week

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from £99 / night

(6) Excellent 

38

Holiday villa with golf nearby in Kissimmee

Kissimmee / Indian Creek

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“a fantastice villa” this is a well appointed villa in a great location,very clean, has a great pool and hot tub it is at the end of a cul-de-sac ( very easy to find ) close to everything you may need supermarkets restaurants and fast food outl  …see more

from £120 / night

£610 - £830 / week

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from £120 / night

(28) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Comfortable villa in good location” We stayed for 4 nights to attend the Mecum Auto auction. The villa was spacious ,clean and reasonable to rent. Accessible to all Orlando attractions. Travelers need to bring everything, paper goods, coffee, cream  …see more

from £65 / night

£455 - £553 / week

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from £65 / night

29

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
An immaculate, larger than average, 4 Bed 4 Bathroom villa. Built in 2011, all rooms in the villa are spacious and have been furnished and maintained to a very high standard. The villa has a south west facing private pool with an incredible lake view. The villa is spa  …see more

from £79 / night

£662 - £863 / week

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from £79 / night

(5) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Country Creek

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m  …see more

from £85 / night

£560 - £665 / week

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from £85 / night

(13) Very Good 

10

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 9 4 nights min

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Executive style four bedroom, two bathroom Villa in Kissimmee. Very close to Disney and Universal theme parks. Private garden, with heated pool and Jacuzzi.  …see more

from £65 / night

£450 / week

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from £65 / night

(6) Very Good 

13

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

6 14 3 nights min

  • 6 bedrooms
  • Sleeps 14
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Disney Villa. Close to Disney, Large 6 bedroom villa, private pool with spa, not overlooked, Florida villa, childrens themed rooms, games room, free wifi, gates resort, gated community, Disney Frozen Room, Star Wars Themed roomfor the perfect family Florida holi  …see more

from £150 / night

£700 / week

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from £150 / night

24

Holiday villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
An amazing family friendly villa in a gated community, a large home from home that has something for all the family! Come explore what our villa has to offer, whilst also exploring the world of Disney only minutes away!  …see more

from £85 / night

£595 - £735 / week

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from £85 / night

(13) Excellent 

49

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Family friendly vacation home with screened in pool...immaculate and exactly as posted!” The home was very clean and had a fully functional and equipped kitchen. The bedrooms were each spacious and had sufficient linens. There is wi-fi and sufficien  …see more

from £86 / night

£512 - £650 / week

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from £86 / night

51

Holiday villa in Kissimmee

Kissimmee / Hamilton's Reserve

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 85 km
  • Swimming pool
Heated swimming Pool, Jacuzzi for up to 6 people, House wide high speed Wi-Fi, 2 Large screen TVs and DVD players in the pool lounge and master bedroom, Quiet seated area in the front lounge, recently refurbished Kitchen, large airy house, fully air conditioned,This lu  …see more

from £111 / night

£729 - £827 / week

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from £111 / night

(4) Excellent 

44

Holiday villa with golf nearby in USA East Coast

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Very nice villa in a quiet and peaceful area.” The villa was very tidy and well maintained. The location was excellent, being very close to a supermarket and to Kissimmee. It was also an ideal location for all the excellent theme parks. We certainly w  …see more

from £90 / night

£585 / week

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from £90 / night

(1) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Tuscany, Florida

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
One storey villa with 3 bedrooms that can easily accommodate 8 people as there is a sofa bed. Ideally located within easy reach of Disney World and is just minutes from the new West Gate entrance to the Walt Disney World Resort  …see more

from £54 / night

£378 - £495 / week

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from £54 / night

16

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are ideally located for the numerous Florida attractions including Disney, Universal Studios, and Seaworld. For golfers the townhouse is ideally located with many fantastic courses within easy reach, with the closest being Falcons Fire Golf Club and Celebration Golf  …see more

from £91 / night

£634 / week

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from £91 / night

(11) Excellent 

69

Townhouse rental in USA East Coast with golf nearby

Kissimmee / Fiesta Key

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 115 km
  • Swimming pool
HDTV DVD BluRay Chromecast WiFi Internet Cable NetFlix Parking Pool Tennis Gym Golf  …see more

from £32 / night

£331 - £414 / week

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from £32 / night

(3) Average 

12

Kissimmee holiday townhouse rental

Kissimmee / Terra Verde Resort

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
Secure and private accommodation; close to amenities and popular attraction parks; clubhouse to cater for all of your needs. WIFI and Cable TV. Relax in luxurious surroundings.  …see more

from £60 / night

£385 / week

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from £60 / night

(17) Excellent 

51

Villa rental in Kissimmee

Kissimmee / Villasol

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
Clubhouse, tennis court, boat dock, children's play area, basketball, nature walks, communal pool & spa.  …see more

from £99 / night

£693 / week

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from £99 / night

29

Holiday home in Kissimmee

Central Florida / Kissimmee

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
On Windsor at Westside, a gated community. The house has a large private South East facing pool and spa. On a large plot with area to play outside. There is a games room with a pool table, air hockey, table tennis and darts. This is a new property furnished to a high  …see more

from £229 / night

£1418 - £2362 / week

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from £229 / night

(12) Very Good 

55

Holiday townhouse in USA East Coast

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“fabulous house in great location with super pool area” this is a great property very well maintained and furnished to a high standard. it is in a great location..only 10 - 15mins from disney and 20 mins from universal. the communal pool and jacuzzi ar  …see more

from £70 / night

£490 - £560 / week

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from £70 / night

(7) Excellent 

44

Townhouse rental in USA East Coast with swimming pool

Kissimmee / Encantada Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Newly and Professionally Furnished 4 bedroom 3 bath town home with lake view, next to club house.  …see more

from £95 / night

£634 - £772 / week

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from £95 / 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
Oak Island Harbor community is a community that is known and appreciated for its convenient location in the prestigious Formosa Gardens area. Upscale private pool homes in a spectacular and peaceful setting yet close to where everything is going on.  …see more

from £119 / night

£827 - £1142 / week

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from £119 / night

(7) 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
“This is house is very accommodating and a great vacation rental.” My family and a few friends recently rented this home and we had an excellent stay. The house is very spacious and will be great for a large group. I love how it has an alarm to make y  …see more

from £71 / night

£497 / week

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from £71 / night

22

Holiday home rental

Central Florida / Kissimmee

4 6 2 nights min

  • 4 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very nice 4 Bed home with 2 Baths, located at Windsor Palms Resort, close to 192 and to many restaurants and markets. a few minutes from Disney Parks, only 3 miles away. 15 minutes away from Universal Studios and 20 min away from Outlet Premium. Excellent clubhouse with  …see more

from £104 / night

£728 / week

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from £104 / night

(6) Very Good 

45

Holiday villa with golf nearby in USA East Coast

Kissimmee / Indian Creek

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Fantastic well equipped/maintained villa in a perfect location close to everything, will definitely be back” We chose this villa as it was well equipped and in a location we knew well, we found a lot of villas can be a bit of a drive away from anythin  …see more

from £110 / night

£750 - £1250 / week

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from £110 / 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
5 bedrooms;3 en suites bathrooms; private pool and spa; optional pool heating; Home Cinema; Fully air conditioned games room; south west facing pool; freeWiFi and high speed internet access; all bedrooms have flat screen cable TVs; free local and international callsAll  …see more

from £95 / night

£665 - £875 / week

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from £95 / night