Air conditioned apartments and villas to rent in Kissimmee

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Kissimmee

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3,522 Holiday homes

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15

USA East Coast holiday villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful spacious home is only 3 miles from Disney World and close to numerous golf courses, restaurants and malls. Ideal for two families sharing. Enjoy your own hot tub and heated large pool, with a BBQ and watching the incredible sunsets after a busy day at the  …see more

from £72 / night

£500 - £560 / week

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from £72 / night

(3) Very Good 

43

Holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxurious 4 bed/3 bath villa is located on the prestigious Emerald Island Resort just 5 minutes from Disney and 2 mins from shops and restaurants. We are 30 mins drive from Orlando International Airport and under 1 hour from Sanford Airport.  …see more

from £70 / night

£490 - £610 / week

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from £70 / 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

(1) Excellent 

49

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
~HUGE SECLUDED WATERFRONT VILLA~ Absolute privacy ~ Large pool deck surrounded by native plants and not overlooked Extended pool deck with luxury furniture ~ Large lanai for al fresco dining Fabulous pool and relaxing spa Fish from the end of our garden  …see more

from £125 / night

£895 - £1565 / week

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from £125 / night

(11) Very Good 

48

Central Florida / Kissimmee

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £121 / night

£740 - £1121 / week

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from £121 / 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
“Home from home... Fantastic!!” My husband & i stayed here with our teenage daughter & her friend, what a great holiday we all had! The villa was perfect... Centrally located on the 192, really comfortable & stylish with every convenience you could eve  …see more

from £109 / night

£763 / week

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from £109 / night

25

Home rental in Kissimmee with swimming pool

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 3 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 £107 / night

£746 / week

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from £107 / night

(14) Very Good 

16

Holiday villa rental

Kissimmee / Indian Ridge Oaks

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely Villa has it's own private pool and is only 5 minutes away from the exciting Disney World, Florida Brilliant access to all of the popular theme parks . There are shops and restaurant close by as well as a community pool, tennis courts and a play area.  …see more

from £54 / night

£375 - £500 / week

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from £54 / night

(2) Excellent 

29

Holiday home in USA East Coast

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great facilities and perfect for us!” The villa was clean, tidy had a great pool and very comfortable beds. Really could not have been better placed to get to the major parks. It was quite simply exactly as advertised and fulfilled our requireme  …see more

from £88 / night

£616 / week

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from £88 / night

(1) Excellent 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun Lake amenities include a clubhouse with gym and pool table, a lighted tennis court and a heated spa and a free form pool.We are two miles from Disney and 15 minutes from Sea World, Premium Outlet Malls and 20 minutes from Univers  …see more

from £69 / night

£480 / week

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from £69 / 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 £113 / night

£746 - £847 / week

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from £113 / 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

(3) Excellent 

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
“The Perfect home in the Perfect location” The only word to describe this beautiful well maintained home is 'wow' I would say it was like a home from home, only much better. Everything has been thought of to ensure a comfortable stay. The pool is super  …see more

from £65 / night

£410 - £595 / week

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from £65 / 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 £130 / night

£912 - £1162 / week

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from £130 / night

18

USA East Coast holiday villa rental

Kissimmee / Crescent Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
6 bedroom pool home. Near Disney, Universal, SeaWorld, Aquatica, Wet 'n Wild, Gatorland, fishing, golf and many other attractions. South facing pool. Privacy fencing at rear. Conservation outlook.  …see more

from £93 / night

£650 - £800 / week

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from £93 / night

(1) Excellent 

39

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 150 km
  • Swimming pool
  • Child friendly
Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can s  …see more

from £80 / night

£560 - £688 / week

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from £80 / night

(5) Very Good 

29

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
-Gated Community with 24/7 security guard on duty-Club House with Community pool, spa and tikki bar. Games Room , Fitness Room and computer access with internet access-Lake View-Pool and Spa-Gated Community with 24/7 security guard on duty-Club House with Community pool  …see more

from £150 / night

£1050 - £1260 / week

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from £150 / night

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Villa, Private Pool, Spa, Sleep 19, Resort Clubhouse, Kitchen, Game room, Xbox360, Heated Pool, BBQ Grill, 8 Bedrooms, 4.5 Bathrooms, Free WIFI, Cable TV, Game Room, Near Disney  …see more

from £280 / night

£1280 - £2552 / week

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from £280 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
6 Bedroom Luxury Villa at Windsor Palms 3 Miles from Disney. Private Pool area with extended decking overlooking beautiful conservation area. 42" flat screen HDTV with cable. Free Wifi Internet. Games room. Gated community. Clubhouse facilities cinema, tennis, gym,  …see more

from £120 / night

£800 - £1150 / week

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from £120 / 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 £107 / night

£746 / week

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from £107 / 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

(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

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This spacious 3 bedrooms and 2 bedrooms vacation home includes the Following Amenities: 4 miles to Disney , 1 King Bed, 1 Queen Bed, 2 Twin Beds, COMMUNITY has heated pool, spa, fitness center, theater room, basketball and tennis court and children playground, Complemen  …see more

from £72 / night

£484 - £686 / week

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from £72 / night

(6) Excellent 

68

Holiday villa in USA East Coast

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
“Fantastic accommodation, Ladysvilla deserves 10 stars instead of 5!!!!!!!!” This is the second time we have stayed in this villa and I cannot express enough how good it is. It is ideally located for all the attractions and theme parks in Orlando. The  …see more

from £89 / night

£565 - £936 / week

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from £89 / night

(5) Excellent 

27

Holiday villa letting

Kissimmee / Windsor Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bed villa near Disney, FREE wifi, private pool and jacuzzi,air con, 2 bathrooms, 220 channel hdtv's, PS3, Xbox360, Windsor Palms Resort, secure gated community with communal pool, tiki bar, playground, sports courts, gym, games room, cinema, shop, bike/dvd/bbq re  …see more

from £120 / night

£825 / week

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from £120 / night

(27) Excellent 

48

Kissimmee / Compass Bay

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 81 km
  • Swimming pool

 …see more

from £80 / night

£564 - £725 / week

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from £80 / night

14

Holiday villa in Kissimmee

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This 4 Bedroom 3 Bathroom home, in the well sought after Terra Verde Resort ,in Kissimmee, is a very spacious villa. Ideal for two families to share as there are two Master Bedrooms and 2 sitting areas. The two twin bedrooms share a Jack and Jill bathroom.There is also  …see more

from £100 / night

£700 - £910 / week

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from £100 / night

(7) Very Good 

37

Kissimmee / Terra Verde Resort

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £73 / night

£509 / week

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from £73 / night

13

USA East Coast holiday townhouse rental

Kissimmee / Venetian Bay Villages

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedrooms, 3 full baths, Close to disney, Sleeps 10, Resort style community, 24 hour security, Close to major shopping areas (Walmart, Flea Markets and Restaurants), Property Manager Close By, Family friendly, Military, Repeat Bookings and Family and Friends Discounts  …see more

from £80 / night

£500 / week

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from £80 / night

28

USA East Coast holiday home rental

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard. The villa is located  …see more

from £109 / night

£722 - £1045 / week

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from £109 / night

22

Home rental in Kissimmee

Kissimmee / Veranda Palms

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
• Accommodates up to 11 people. • 4 beds and 3 ½ bath • Living room with a big screen tv and dining room combo. • Keyless front door entry. • Free cable, internet wi-fi, local and us long distance calls. • Private game room. • Private enclose pool area.  …see more

from £130 / night

£904 / week

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from £130 / night

(1) Very Good 

34

Kissimmee / Crescent Lakes

4 8 4 nights min

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

 …see more

from £92 / night

£644 / week

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from £92 / 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 £73 / night

£509 / week

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from £73 / night

(17) Excellent 

24

Holiday villa letting

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Had a great time at this Villa” We arrived to a clean, well kept villa. We unloaded our luggage and ran over to the nearby Wal-Mart to get some food etc. It was very convenient having a Wal-Mart near by (as well as several restaurants). The pool was  …see more

from £60 / night

£395 - £550 / week

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from £60 / night

24

Holiday villa in USA East Coast

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Spread out and enjoy a sunny six bedroom, four bathroom villa in Windsor Hills Resort. Best of all, it is only two miles to Walt Disney World! FROZEN Themed BedroomNO REAR NEIGHBOURS! To ensure your privacy, our pool overlooks a natural area, not another house!Special D  …see more

from £218 / night

£1452 - £2097 / week

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from £218 / night

30

Holiday home with golf nearby in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous location for everything the area has to offer. Only 10 minutes from Disney main gates & 20 mins to Universal. Convenient for shops, restaurants and outlets Complex offers heated pool, tennis, basketball, play area, splash pad, volley ball, & other amenities al  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

(1) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Spacious 3 bedroom/2 bathroom villa. Minutes from all the Disney attractions. Complimentary use of all complex facilities inc 3 great pools, a gym, floodlit tennis courts and a children's park.  …see more

from £50 / night

£455 / week

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from £50 / night

(5) Very Good 

88

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Seasons Sunshine Villa named from the fact that the pool is in sun all day offers the ideal location for a large family or two family holiday of a lifetime.  …see more

from £95 / night

£625 - £840 / week

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from £95 / night

78

Holiday home in USA East Coast

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
- 2 miles from Disney - Shuttle Bus Service to theme parks - Private cinema for guests - Slides, water jets, spa pool and hot-tub - Wi-Fi and Home telephone - 4 Bed/4Bath At The Beautiful Windsor Hills Resort  …see more

from £108 / night

£756 / week

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from £108 / night

19

Kissimmee holiday home rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
Upscale 4 bed 4 baths home with enclosed pool is the perfect place to relax after a long day at the parks. This beautiful pool home is 4 bedrooms 4 bath, located in the most sought after gated resort community of Bella Vida about 10 miles from Disney World.  …see more

from £84 / night

£588 / week

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from £84 / night

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