Kissimmee apartment or villa with a heated pool

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Kissimmee

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1,301 Holiday homes

Filters applied: Heated pool (1,303)

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

(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 £196 / night

£1366 / week

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from £196 / 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 £244 / night

£895 - £2146 / week

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from £244 / night

(32) Excellent 

20

Holiday townhouse in Kissimmee

Kissimmee / Regal Oaks

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“excellent house & location” This was our 2nd time staying at Vic`s house and will always be our 1st choice. the location is perfect as it is only just behind old town, which is just a short walk and there is always something going on. It is perfect f  …see more

from £75 / night

£525 - £650 / week

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from £75 / night

Featured properties

(1) Very Good 

20

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
“Lovely villa in a super location” We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the water shoot at th  …see more

from £98 / night

£683 / week

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from £98 / night

(7) 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 £103 / night

£718 - £854 / week

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from £103 / night

25

Holiday villa in Kissimmee

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 104 km
  • Swimming pool
  • Child friendly
Mickey’s Ritz at Veranda Palms is a private vacation home providing spacious accommodation with luxury, upgraded contemporary furnishings. The home has 4 bedrooms, 3 bathrooms, a large pool (30ft x 15ft) + spa, a south west facing pool deck with fabulous pool furn  …see more

from £105 / night

£729 - £957 / week

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from £105 / 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

(1) Excellent 

18

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £108 / night

£752 / week

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from £108 / night

(2) Excellent 

23

Holiday townhouse with golf nearby in Kissimmee

Kissimmee / Fiesta Key

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This glorious fully furnished townhouse was built in 2005 in the magnificent Key West style. This house features 3 wonderful bedrooms and 2.5 exquisite bathrooms and can house up to 8 people,within the gated community of Fiesta Key.<br />The Villa is close to all  …see more

from £70 / night

£431 - £545 / week

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from £70 / night

(2) Excellent 

71

Holiday villa with shared pool in Kissimmee City

Kissimmee / Kissimmee City

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Perfect in every way” we have stayed here several times (approx. 10) and every time the house delivers what we expect in a Florida villa. Villa is cleaned to a high standard on arrival, the kitchen has everything you have in your own kitchen at home s  …see more

from £70 / night

£450 - £495 / week

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from £70 / night

(3) Excellent 

24

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Large Deck and Lanaii ,private pool not overlooked .Tiled floors all rooms except Family room  …see more

from £90 / night

£580 - £748 / week

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from £90 / night

(7) 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

(43) 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
“As good as it gets...” When we arrived at the villa we were blown away, It was clean, well presented and extremely modern...and most definitely had the WOW factor!! Everyone in our party were excited and more so on seeing the terrific pool and huge g  …see more

from £130 / night

£895 - £995 / week

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from £130 / night

(4) Excellent 

98

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Emerald Isle Excellence” We stayed here at the end of our 2 week Florida road trip for 5 nights, 24 -29 Oct. Wished we could have stayed longer.Upon arrival at front gate the security were polite and helpful took details of our car and directed us to  …see more

from £82 / night

£570 - £848 / week

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from £82 / night

22

Kissimmee holiday villa rental

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious villa with private pool (Optional heating if required). 3 bedrooms plus queen sofa bed in the lounge means 8 people can sleep comfortably. Covered lanai area for relaxing and dining by the pool. Games room with pool, ping-pong and electronic darts. Situated in  …see more

from £50 / night

£350 - £500 / week

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from £50 / 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 £90 / night

£895 - £1057 / week

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from £90 / night

(2) 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 £93 / night

£649 / week

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from £93 / 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 amen  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

(1) Excellent 

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 £81 / night

£507 - £621 / week

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from £81 / night

(3) Very Good 

23

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
6 beds, 4Bath with 3 master suites, new digital TV set in all bed rooms, a 60" TV in living room, Minutes to Disney World and shopping malls, A great place for family vacation with gated community & forest view. A Child high chair, 3 strollers are available on  …see more

from £130 / night

£918 - £1349 / week

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from £130 / 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 £94 / night

£655 / week

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from £94 / 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
Emerald Island resort is centrally located within 3 miles to Walt Disney World, 14 miles to SeaWould, 17 Universal Studios, and just a short drive to many of the other theme parks that Central Florida has to offer.<br />3 miles to Disney 14 miles to SeaWorld 17 mi  …see more

from £244 / night

£895 - £2105 / week

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from £244 / night

(5) 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
“Fantastic villa and excellent location..” When visiting this fabulous villa I was very impressed with the layout and the pool area, much larger than expected. there was lots of additional equipment in the kitchen area. On arrival we were greeted with  …see more

from £66 / night

£460 - £640 / week

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from £66 / night

9

Holiday townhouse in Venetian Bay Villages

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Beautiful 3 bedroom home on the popular Venetian Bay in Kissimmee. This is the perfect place to relax after your busy day at the parks. Only 15 minutes from Disney World and great facilities in this gated community makes planning your Florida Vacation easy.The s  …see more

from £78 / night

£541 - £740 / week

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from £78 / night

18

Crescent Lakes 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 - £750 / week

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from £93 / night

(2) Very Good 

12

Holiday villa rental

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Great rates & great location. A beautiful property in Kissimmee, Florida, our self catering holiday home offers so much more than just an ordinary holiday home, in one of the best locations in the Orlando area. A home from home, with everything to ensure a truly wo  …see more

from £72 / night

£450 / week

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from £72 / night

(4) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Indian Ridge Oaks is a quiet, sought after development with a lovely mix of local Floridian families and rental properties. The villa is not near any main roads to be bothered by traffic noise but near to the theme parks and interstates to make this a fantastic location  …see more

from £110 / night

£549 - £700 / week

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from £110 / night

(7) 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

(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 £90 / night

£570 - £903 / week

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from £90 / night

(1) Average 

54

Villa rental in Kissimmee with golf nearby

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Luxury 4 bedroom villa with south facing pool and spa. Air conditioned throughout, great location just 5 minutes from Walt Disney World.<br />Indian Ridge is a quiet residential community, yet just minutes from theme parks, shops and restaurants  …see more

from £80 / night

£495 - £695 / 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
“Superb stay close to Orlando and parks.” My family, together with my parents and sister in law stayed at this villa during the last week of December for 6 days. This was an excellent home, spacious and clean with all the amenities a villa should h  …see more

from £140 / night

£980 - £1400 / week

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from £140 / 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

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 £236 / night

£1464 - £2049 / week

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from £236 / night

(8) Very Good 

49

Home rental in Kissimmee

Kissimmee / Lake Berkley

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Our stay in Florida was made that much more enjoyable staying here” 995 Lake Berkley Drive, was a great place for us to stay during our recent two week trip to Florida. The estate itself is very impressive, clean and well maintained. A safe and secure  …see more

from £122 / night

£826 - £996 / week

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from £122 / night

(3) Excellent 

100

Kissimmee / Paradise Palms

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 103 km
  • Swimming pool
  • Child friendly

 …see more

from £98 / night

£683 / week

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from £98 / night

(1) Very Good 

22

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Privacy describes Encantada. Encantada is found along a tree lined entrance with private manned guard 24 hours a day only 9 km to Disney Magic Kingdom, 8km to Animal Kingdom and has everything you need for a magical vacation. Enjoy the private, screened in pools in your  …see more

from £98 / night

£683 / week

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from £98 / night

(10) Excellent 

20

Bellavida Resort holiday villa rental

Kissimmee / Bellavida Resort

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
“5 star villa - everything you need for the holiday of a lifetime” This was our third visit to Orlando and was way beyond our expectations. The villa was amazing. Spacious, luxurious and well equipped with everything you need for a relaxing holiday.  …see more

from £160 / night

£1087 / week

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from £160 / 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

(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 £78 / night

£546 / week

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from £78 / night

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
Lake Berkley is a private gated community - a veritable oasis ! Located just off the busy and action packed Highway 192 with its array of shops, entertainment & restaurants, Lake Berkley offers the perfect location for that holiday of a lifetime in the Sunshine Stat  …see more

from £123 / night

£860 / week

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from £123 / night