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Kissimmee

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2,126 Holiday homes

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

(5) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Comfortable, smart, spacious, well equipped villa.” We stayed as two family groups comprising 8 Adults and 2 kids. The accommodation was flexibly arranged and everyone could find there own space when they wanted it. The villa's own pool and hot tub w  …see more

from £165 / night

£1155 - £1295 / week

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from £165 / 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 £160 / night

£1115 / week

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from £160 / night

(11) Very Good 

20

Holiday villa with indoor pool in Paradise Palms

Kissimmee / Paradise Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic villa and resort in good location for attractions” Stayed in the villa for 2 weeks. There were 10 of us yet the villa was so roomy. Very comfortable and modern with all you could need. The paradise palms resort is also excellent. Great  …see more

from £200 / night

£1400 - £1680 / week

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from £200 / 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
“Everything we needed and more.” We stayed at this villa for 3 weeks ,with other family members. In total there were 10 of us. The villa was spotlesly clean when we arrived and it was very welcoming. There was a fantastic welcome pack for when we arriv  …see more

from £156 / night

£1076 - £1916 / week

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from £156 / night

(24) Excellent 

23

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Beautiful condo in a great location” The condo at cane island is absolutely wonderful. We were delighted with the choice we made having spent hours trawling the Internet before booking. Everywhere was sparkling clean and absolutely beautifully decorat  …see more

from £65 / night

£455 / week

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from £65 / night

(24) Very Good 

27

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 - £1054 / week

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from £80 / night

(11) Excellent 

24

Calabria, Orlando holiday villa rental

Kissimmee / Calabria, Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Just what we wanted. Great space. Great location” Preparation communications from owner was excellent. Group of 10 with no issues at all throughout the stay. Quite and pleasant neighbourhood.  …see more

from £152 / night

£1064 / week

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from £152 / 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 £104 / night

£720 / week

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from £104 / 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 £130 / night

£900 - £1150 / week

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from £130 / 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

£616 - £952 / week

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from £88 / 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 £240 / night

£880 - £2232 / week

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from £240 / 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 £68 / night

£476 / week

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from £68 / night

(5) 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 £68 / night

£476 / week

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from £68 / night

(12) Excellent 

32

Kissimmee / Paradise Palms

5 12 Min stay varies

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

 …see more

from £96 / night

£924 / week

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from £96 / night

(8) 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

(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 £66 / night

£448 - £696 / week

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from £66 / night

(6) Excellent 

68

Holiday villa in Kissimmee

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 £88 / night

£560 - £888 / week

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from £88 / night

(13) Excellent 

60

Holiday condo rental

Kissimmee / Legacy Dunes Resort

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 78 km
  • Swimming pool
“Excellent value and great location!” Lovely apartment, really comfortable and spotlessly clean. We received 2 parking passes and there was always parking available at the door. Complex is quiet, secure and nicely landscaped, pool area is great. Locati  …see more

from £50 / night

£350 - £450 / week

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from £50 / night

(34) Very Good 

20

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • Sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Amazing property!” This property really is as amazing as the photos show! Andy offers great communication before, during and after the stay, and it really is a fantastic place to stay. We visited Universal Studios and Wet'n'Wild and it's about a 20  …see more

from £99 / night

£675 / week

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from £99 / night

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
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 £131 / night

£789 - £978 / week

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from £131 / night

13

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury 4 bed / 3 bath detached villa with private heated pool / spa, wifi broadband and games room on High Grove Gated Community, 10 mins from Disney at junction of 192 and Highway 27. It is ideally located for the theme parks, golf and the whole Florida experience.  …see more

from £52 / night

£340 - £668 / week

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from £52 / night

(5) Very Good 

88

Holiday villa in Kissimmee

Kissimmee / Seasons Resort

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • 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

£840 / week

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from £95 / night

(2) Excellent 

11

Kissimmee holiday townhouse rental

Kissimmee / Compass Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 101 km
  • Swimming pool
This house is close to all the main attraction's, shopping outlets, restaurants. It is in a gated community it has a private patio with a view of the lake, close to one of the children's play area.  …see more

from £82 / night

£570 - £730 / week

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from £82 / night

(2) Very Good 

13

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Amazing stay, great villa” Had a lovely stay for 2 weeks. Very easy to book and a lot of useful information emailed before and in the villa as well. Brilliant directions- made it a less daunting experience! Villa very clean with plenty of room and s  …see more

from £80 / night

£499 - £611 / week

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from £80 / 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 £96 / night

£644 - £784 / week

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from £96 / 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

(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

(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 £80 / night

£520 - £896 / week

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from £80 / night

(14) Very Good 

29

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“It was perfect, we had everything we needed ....” Family vacation with small children and grandparents, the villa was perfect, we had everything we needed and everything was to a really high standard. Lovely and clean, it really made our holiday. The  …see more

from £140 / night

£980 - £1400 / week

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from £140 / night

(8) Very Good 

22

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

5 12 5 nights min

  • 5 bedrooms
  • Sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
5 Beds,4 Baths. Sleeps 12. AC. Outdoor Pool. Xbox. Wii. PS2. Games Room with Pool Table, Foosball, Air Hockey.  …see more

from £101 / night

£706 - £840 / week

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from £101 / night

(1) Very Good 

20

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 105 km
  • Swimming pool
“Clean & Comfortable Family Friendly Villa” We thoroughly enjoyed our stay at this villa and found it to be well equipped and in a great position. It was easy to travel to any of the main attractions and has tons of shops and restaurants on its doorste  …see more

from £112 / night

£784 / week

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from £112 / night

(2) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Child friendly
  • Air conditioning
Nice resort very close to Disney World.  …see more

from £100 / night

£640 / week

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from £100 / 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

(3) Very Good 

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

24

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
Disney World, Universal Studio, SeaWorld, Resort, Private Heated Pool, Spa, WIFI, Game room, Internet, Cable TVs<br />3 miles to Disney 14 miles to SeaWorld 17 miles to Universal. Minutes to Super Market and Restaurants  …see more

from £240 / night

£880 - £2341 / week

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from £240 / 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 £95 / night

£585 - £595 / week

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from £95 / night

(6) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fabulous pool” Beauitiful, clean villa with an open floor plan. Located in a very quiet neighborhood. Great pool.Pool toys in garage. Well stocked with everything you need. Sheets, bath towels, kitchen towels and towels for the pool use. Air condition  …see more

from £66 / night

£460 - £640 / week

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from £66 / night

(9) Excellent 

16

Villa rental in Kissimmee

Kissimmee / Indian Creek

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home has lots of great features-32ft Heated poolHot bubbling SpaAir-conditioned games-room2 en-suite bedroomsTVs and DVD players in all bedrooms  …see more

from £114 / night

£800 / week

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from £114 / night

16

Legacy Dunes Resort holiday condo rental

Kissimmee / Legacy Dunes Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Gorgeous fully furnished 4 bed 2 bath corporate rental apartment Orlando, FLLocation: Legacy DunesAbsolutely gorgeous, 4-bed, 2-bath condo located in the fabulous Resort Style privately gated community of Legacy Dunes. It comes fully furnished to accommodate 8 persons v  …see more

from £75 / night

£475 - £850 / week

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from £75 / night

(3) Very Good 

92

Cumbrian Lakes holiday home rental

Kissimmee / Cumbrian Lakes

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“This place is amazing” We stayed here for a week after a tiring but fun road trip and as a base station for the theme parks! It was exactly what we needed for a group of 7 friends! Good location for the parks, lovely area and amazing view of the sunse  …see more

from £195 / night

£1365 / week

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from £195 / night