Villas with a pool Kissimmee | Apartments to rent with swimming facilities

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Kissimmee

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2,785 Holiday homes

Filters applied: Swimming pool (2,787)

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

(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 £73 / night

£533 - £674 / week

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from £73 / night

(4) Excellent 

44

Holiday villa with golf nearby in Kissimmee

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

42

Condo rental in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Hills is perhaps the finest resort community in the Disney area. With world famous theme parks and attractions just minutes away, a stay here will create family memories to last a lifetime.  …see more

from £88 / night

£621 - £960 / week

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from £88 / night

Featured properties

(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

(7) Excellent 

44

Townhouse rental in Encantada Resort 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 £97 / night

£650 - £791 / week

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from £97 / night

(1) Very Good 

15

Kissimmee 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

(18) 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

(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

(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,  …see more

from £161 / night

£1124 / week

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from £161 / night

(10) Very Good 

46

Villa rental in Indian Point with shared pool

Kissimmee / Indian Point

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Outstanding Villa - Real Home from Home” Superb villa - really clean, airy and well-decorated with a lovely pool and patio area. Plenty of room for everyone in the 4 bedrooms & especially liked having 3 bathrooms to make leaving for the parks much qui  …see more

from £66 / night

£460 - £690 / week

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from £66 / night

(5) Excellent 

24

Holiday villa with swimming pool in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cumbrian Lakes is an exclusive gated community with lakes, cycling & walking trails & a kids play area.  …see more

from £100 / night

£700 - £850 / week

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from £100 / night

(10) Excellent 

28

Doral Woods holiday villa rental

Kissimmee / Doral Woods

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“It was just GREAT!” Large heated pool, large and clean rooms! Everything was as promised in the description! Ideal family holiday with guaranteed comfort! To Disney 25 Minutes, Universal 35 Minutes :-)  …see more

from £65 / night

£450 - £480 / week

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from £65 / night

(8) Very Good 

63

Coral Cay holiday home rental

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“A Nice Stay!!!!” We really loved it and we wish if we would have stayed. Beautiful scenic, nice backyard overlooking the lake. The pool was nice with a hot pool  …see more

from £59 / night

£413 / week

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from £59 / night

(2) Excellent 

16

Holiday villa in Kissimmee

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
This beautiful and spacious villa with a private pool is in Calabria- a small exclusive villa estate in Kissimmee. With 5 bedrooms and 4.5 bathrooms including 2 master en-suite bedrooms, the villa is well designed for 2 families to share. The villa is furnished to an  …see more

from £100 / night

£700 / week

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from £100 / night

(3) Excellent 

16

Holiday villa in Indian Creek

Kissimmee / Indian Creek

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Great Florida Villa in a Perfect Location” Myself & my Family spent a lot of time looking on website at Villas for our Florida Holiday, hoping to find a Good deal with the right location near to all the Attractions and a villa that would be suitabl  …see more

from £121 / night

£847 / week

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from £121 / 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
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 room<br />for the perfect family  …see more

from £150 / night

£700 - £800 / week

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from £150 / night

(10) Excellent 

24

Holiday villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic!” We have just returned from Palm Tree Villa. We stayed there for nearly two weeks and to say we had a fantastic time and enjoyed it there is an understatement. The house is as clean as advertised. It has all the facilities in place to make  …see more

from £100 / night

£695 - £875 / week

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from £100 / night

(4) 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 £70 / night

£445 - £595 / week

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from £70 / night

(4) Very Good 

40

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Would recommend” Beautiful home, my family and I enjoyed every bit of it. Very spacious, listed as 4 bedrooms also has a loft so it's more like 5, we had a whole room we never used and everyone was comfortable. In a great area for shopping markets and  …see more

from £105 / night

£726 / week

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from £105 / night

(23) Very Good 

23

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just Perfect” My wife and I are regular visitors to the Orlando area and have stayed in several Rental Villas in the past. It was our first time at ‘Ventura Villa’ hopefully not our last, we had a really enjoyable stay. The villa is clean, well fur  …see more

from £80 / night

£525 - £3325 / week

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from £80 / night

(3) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Kissimmee / Lindfields

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Lindfield is one of the closest areas to Disney  …see more

from £85 / night

£595 - £735 / week

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from £85 / night

(12) Excellent 

31

Kissimmee / Paradise Palms

5 11 Min stay varies

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

 …see more

from £109 / night

£932 / week

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from £109 / 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 £65 / night

£440 - £550 / week

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from £65 / night

(2) Very Good 

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.<br />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

(9) Excellent 

48

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa is situated in the beautiful Emerald Island Resort, regarded as one of the best resorts in the area. It is located south of Hwy 192 near Mile Marker 5 just minutes from I4. It is approximately 4 miles to the gates of Walt Disney World and within easy reach of  …see more

from £89 / night

£888 - £1049 / week

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from £89 / night

(2) Very Good 

18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a  …see more

from £171 / night

£1200 / week

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from £171 / night

30

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 £101 / night

£678 - £884 / week

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from £101 / night

(2) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • 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

£350 / week

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from £50 / night

(7) Excellent 

18

Condo rental in Kissimmee

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Top rated in trip advisor condo 10 mins away for Disney currently voted 2 in whole area. Spacious, quality nothing better  …see more

from £121 / night

£799 / week

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from £121 / night

(11) Excellent 

69

Townhouse rental in Fiesta Key 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 £33 / night

£400 - £424 / week

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from £33 / night

(2) 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 - £490 / week

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from £54 / night

(2) Very Good 

20

Holiday condo in Legacy Dunes Resort

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

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

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

£464 - £686 / week

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from £72 / night

(4) Excellent 

48

Apartment rental in Kissimmee with shared pool

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Walk to shops, restaurants and supermarkets. We are 5 minutes from Disney and 20 minutes from Universal. Fully equipped kitchen and washer/dryer with free WIFI. Free parking.  …see more

from £69 / night

£480 / week

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from £69 / night

(30) 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
“We'd stay again in a heartbeat !!” Everything about this place was "top shelf". It was sparkling clean and comfortable, with all the amenities one could ask for. Beautifully decorated and thoughtfully equipped, this place completely met our needs an  …see more

from £135 / night

£800 - £995 / week

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from £135 / night

(24) Excellent 

56

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Very nice villa, exactly as advertised.” Thoroughly enjoyed our stay at Dolphin Villa. The villa is located in a secluded estate with large private garden to rear and no neighbours overlooking the pool deck. The villa is in good condition and we didn'  …see more

from £125 / night

£795 - £975 / week

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from £125 / night

(6) Excellent 

31

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing family home” Perfect family home to use with a large family (13 of us) plenty of space for all, home from home. A lovely pool with safety fence around which was excellent as we had a 2year old.very clean. Excellent location with resturants ne  …see more

from £158 / night

£1085 - £1932 / week

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from £158 / 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

(12) Very Good 

55

Holiday townhouse in Kissimmee

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