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Kissimmee

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4,240 Holiday homes

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

(21) Excellent 

24

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Location” Great location that is close to restaurants, stores, and Disney World and also very affordable. Our kids loved the pool.  …see more

from £75 / night

£525 - £600 / week

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from £75 / night

(43) Excellent 

40

USA East Coast holiday villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful villa in an excellent location” I stayed at Disney Davella for one week with my husband and parents. There are two excellent master bedrooms which made it perfect for us (with a bathroom off each) and an extra toilet downstairs as well. Th  …see more

from £90 / night

£595 - £850 / week

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from £90 / night

(23) Excellent 

8

Holiday condo in Kissimmee

Kissimmee / Cane Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 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 £50 / night

£350 - £420 / week

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from £50 / night

(12) Very Good 

24

USA East Coast holiday villa rental

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Villa for families” We stayed at this villa with our daughter and my wife's parents. This is a fantastic property for more than one family as there are two master suites as well as a queen room and two twin bedrooms. The best feature is the exte  …see more

from £79 / night

£550 - £800 / week

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from £79 / night

(35) Excellent 

39

Villa rental in USA East Coast

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Wonderful place to spend your hollidays with your family” Wonderful villa to stay in a group of 6. The house was well equipped and very good conditions. The location of the house was very convenient (there is a wallmart just 1 mille away and not that  …see more

from £80 / night

£495 - £505 / week

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from £80 / night

(13) Excellent 

41

Holiday condo with golf nearby in Kissimmee

Kissimmee / Cane Island

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Swimming pool
“Excellent Accommodation and Ideal Location” This accommodation was excellent it was very clean, spacious, well maintained and had absolutely everything needed in order to make it a real home from home. The added bonus of free internet access definite  …see more

from £76 / night

£476 - £596 / week

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from £76 / night

(7) Very Good 

20

Holiday townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A Beautiful 5* Star 'Spacious', 4 bedroom, 3 bath Vacation home, south Facing Private Pool on a holiday resort with Communal Pool, tennis Courts, Games Room, Sauna, Gym, Card Room. Tiki Bar. 5 Mins from Disney and all the major attractions. Ideal for families  …see more

from £93 / night

£600 - £940 / week

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from £93 / night

(5) Very Good 

45

Holiday villa rental

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Disney location with secluded heated pool and King sized Four Poster Bed.This newly renovated property, located in one of the nicest residential communities in Kissimmee, is a great base for any holiday in the area.  …see more

from £80 / night

£500 - £675 / week

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from £80 / night

(2) Excellent 

40

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
Ready to have your dream Florida vacation? You're gonna need a dream house!This vacation villa has 4 bedrooms, 3 bathrooms, and is totally teeming with luxury! Get ready to dive into the exclusive community of Hamilton's Reserve, which offers extreme p  …see more

from £104 / night

£720 - £960 / week

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from £104 / night

(27) Very Good 

24

Holiday condo with golf nearby in USA East Coast

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Ideal "near to Disney" condo” Condo had everything we needed at very reasonable price, especially for Christmas period. Owners (Ronald and Pam) very helpful with arrival instructions, directions, etc. Useful local info provided at condo. Good variety  …see more

from £35 / night

£219 - £335 / week

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from £35 / night

(30) Excellent 

23

Holiday home with swimming pool in USA East Coast

Kissimmee / Oak Island Cove

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Ideally situated, beautifully kept property with everything you ever need, a home from home!” This was our first family holiday to Florida and the villa absolutely had everything we wanted to enjoy our holiday! Ideally situated with ease if access to  …see more

from £100 / night

£600 - £700 / week

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from £100 / night

(5) Excellent 

16

Holiday villa with swimming pool in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Soon You'll Be Staying at a Individually Designed Luxury 4 Bed villa with all of the home comforts you expect.Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some family time  …see more

from £76 / night

£520 - £1036 / week

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from £76 / night

(17) Excellent 

56

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
“Just what we needed.” Plenty of room for us all. Easy routes to parks etc. if you are happy to drive in US. House had everything we needed. Pool was perfect.  …see more

from £93 / night

£650 - £850 / week

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from £93 / night

(6) Very Good 

20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Fully furnished and extensively equipped. Flat screen TV's with DVD players in living room and all bedrooms.  …see more

from £75 / night

£525 - £665 / week

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from £75 / night

(29) Excellent 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“One of the best villas we've stayed in!!!” Lovely house in a very convenient location - 2 minutes from a huge Walmart and numerous restaurants along the 192, 20 minutes to Disney, 35 minutes to Universal and International Drive. House is spacious, we  …see more

from £96 / night

£672 - £736 / week

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from £96 / night

(25) Very Good 

18

Kissimmee holiday townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Great location and facilites” This house gave us everything we needed for a great holiday. Clean, well equipped and in a pleasant area. Pools and public areas very well kept. Would recommend for couples and families alike. Six adults would be easily a  …see more

from £42 / night

£294 - £357 / week

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from £42 / night

(18) Very Good 

17

Holiday villa in USA East Coast

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Magnificent Accomadation” We arrived for our stay of 2 weeks after travelling for 20 hours, we found the place easily everything was as described, the only disappointment my girls had was the pool was cold , however it soon warmed up after a couple o  …see more

from £65 / night

£299 - £475 / week

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from £65 / night

(6) 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 £95 / night

£650 - £750 / week

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from £95 / night

(24) Very Good 

12

Villa rental in USA East Coast with swimming pool

Kissimmee / Lindfields

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“A great place to relax after a busy day at Disney World” We had a wonderful holiday staying at Sunrise Villa in Lindfields Reserve. The villa is lovely, very well equipped for self catering and is as good as it looks in the photos. The pool area is pa  …see more

from £61 / night

£425 - £550 / week

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from £61 / night

(5) Excellent 

26

Holiday villa in USA East Coast

Kissimmee / Formosa Gardens

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Superb chillout base for a large group visiting the theme parks” As a group of 9 adults and 2 children, we thought it may prove difficult to rent anywhere large enough to accommodate everyone under the same roof, but this house met this need with hono  …see more

from £218 / night

£1520 - £1983 / week

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from £218 / night

(9) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Doral Woods

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Home away from home!” We thoroughly enjoyed the villa with all of its amenities. Clearly this was equipped with children in mind. Our 2, 8 and 10 year-olds found things to do for the entire stay. Naturally the pool was number one, but they found plent  …see more

from £74 / night

£470 - £1260 / week

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from £74 / night

(7) Excellent 

28

Holiday villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Santa Caterina is located in the beautiful Windsor Hills Resort where you can enjoy all the comforts and amenities of home with all the attractions and the social interactions of a First Class Resort.ALL PRICES QUOTED INCLUDE 13% FLORIDA TAXRefundable security deposit &  …see more

from £116 / night

£812 - £1085 / week

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from £116 / night

(11) Excellent 

14

Holiday villa with swimming pool in USA East Coast

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic Luxury property close to Disney!” We have just returned from a 2 week Holiday to Florida and used this house as our base. The house is located in Kissimee which is an ideal base to visit all the attractions, Disney is about 15 mins, Universa  …see more

from £65 / night

£450 - £500 / week

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from £65 / night

(11) Excellent 

19

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Lots of space and nice pool” We travelled with two children (9&10) plus two teenagers and everybody enjoyed our stay! Plenty of room for everybody, own swimming pool and jaguzzi plus communal pool. Short (15-20 min) drive to the amusement parks. Sever  …see more

from £85 / night

£565 / week

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from £85 / night

(21) Very Good 

22

Holiday home in Kissimmee

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • 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 £72 / night

£495 - £775 / week

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from £72 / night

(7) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
Positioned on Oak Island Cove next to Formosa Gardens, this is one of the most exclusive vacation sub rental divisions in Central Florida. Every amenity is close at hand for a wonderful vacation. No other location boasts a 5 minute journey to Disney World, Orlando. The  …see more

from £95 / night

£665 - £945 / week

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from £95 / night

(22) Excellent 

23

Holiday villa rental

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 84 km
  • Swimming pool
  • Child friendly
“Excellent , pleasant and very convenient .” We enjoyed 8 wonderful days at Villa Nirvana. We were an extended family, a groop of 8 people including teenagers and a baby. All of us wish to emphasize that the time we spent at the villa was wonderful. E  …see more

from £88 / night

£616 - £868 / week

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from £88 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent Villa highly recommend it, great location.” Property was excellent, close to Disney and places to eat. The weather was nice and the complex where the villa was situated was well looked after, nice and clean and staff was pleasant.  …see more

from £136 / night

£920 - £1450 / week

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from £136 / night

(23) Excellent 

24

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic” This holiday was excellent the home was absolutely fab, it was differently home from home The villa we stayed in was pristine and had every little thing you could want and more. It was a pleasure to enter into a home that was spotless. I  …see more

from £68 / night

£475 - £570 / week

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from £68 / night

(11) Excellent 

23

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Everything you need..and more” Beautiful open plan villa, lots of room, clean, the sofas are really soft and cosy after a day at the parks. The pool was a definate hit with the kids, as was the games room. The gated community was very friendly and h  …see more

from £92 / night

£640 - £700 / week

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from £92 / night

(16) Excellent 

27

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Couldn't ask for a nicer place!!” We stayed in the Diamond Villa on our first trip to Disney World and we were blown away with how beautiful this villa was! It was beautifully decorated, spotlessly clean, extremely well equipped and more comfortable t  …see more

from £121 / night

£847 - £1100 / week

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from £121 / night

(6) Excellent 

21

USA East Coast holiday home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Fabulous home away from home” Ten of us stayed in this Villa, consisting 3 children, 2 teenagers and 5 adults. We had plenty of room for all of us as it's such a large property. The Villa was very well equipped with everything we needed and spotlessly  …see more

from £132 / night

£924 - £1512 / week

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from £132 / night

(42) Excellent 

91

Holiday villa in USA East Coast

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Excellent villa and facilities” The Villa was as describes, nice quiet location, easy access to parks. Facilities really nice, was handy to have a guest food pack - especially if you are on a late flight. Very nice patio furniture - much nicer than  …see more

from £95 / night

£650 - £925 / week

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from £95 / night

(15) Very Good 

18

USA East Coast holiday villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“1st time in Florida fantastic stay - lovely villa” This was our first time to florida with 2 small children, we had a lovely time, the villa was clean and had everything we needed for our stay, having the cot and highchair free of use was great. The p  …see more

from £60 / night

£420 - £500 / week

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from £60 / night

(18) Excellent 

24

Holiday townhouse rental

Kissimmee / Encantada Resort

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
“Fantastic accommodation in lovely resort” What a beautiful house, modern and clean with everything you could need. The house is situated in a lovely gated resort and is in a great position near to the communal pools and club house. The owners have tho  …see more

from £95 / night

£640 - £750 / week

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from £95 / night

(2) Excellent 

15

Kissimmee holiday villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
Minutes from Disney, emerald island resort, 4 bed, not overlooked, private heated pool & spa, 3 bath, games area, free broadband, resort facilities.  …see more

from £148 / night

£1036 / week

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from £148 / night

(66) Excellent 

24

Holiday villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“Excellent location, beautiful and comfortable villa.” It was our first time not staying at a hotel. Don't think we'll stay at one again. Being at this house was just perfect for us. Very comfortable and close to everything. Would surely go back!  …see more

from £70 / night

£465 - £580 / week

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from £70 / night

(12) Very Good 

17

Holiday villa in USA East Coast

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great House, Perfect Location!” House was in great shape. Had everything needed. Pool was perfect. Near everything needed. Shopping, minutes from the theme parks. Payment plan was perfect for people on a budget. Owner very responsive. We hope to rent  …see more

from £60 / night

£360 - £550 / week

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from £60 / night

(16) Excellent 

22

Holiday villa with swimming pool in USA East Coast

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Perfect villa for all the Orlando attractions” Belles Cove is a lovely family home and ideally located for the parks and other attractions The rooms are tastefully decorated and with the benefit of 4 bathrooms presents ideal accommodation for a large  …see more

from £100 / night

£635 - £825 / week

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from £100 / night

(15) Excellent 

23

Kissimmee holiday villa let

Kissimmee / Bellavida Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Very vice decorated big villa in a great area” A lovely big villa, all amenities and very nicely decorated inside. Good size pool with sun from morning to evening and overlooking the resort lake. The resort has a paved path around the lake which is ni  …see more

from £149 / night

£1045 - £1495 / week

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from £149 / night

Top Destination reviews

Disney Family Villa - Private Pool & Jacuzzi
Great vacation home!

Thanks for a great vacation experience! The house was neat and clean, with all facilities as advertised. Food and drinks that we found on arrival was a nice touch! Would definitely recommend to others. … see more
Stunning Lakeview Luxury Villa with WiFi and Hot Tub
Superb villa

The only fault with this property is that we couldn't stay longer. The booking process went smoothly. The owner was very attentive and answered all of our questions promptly. The villa is in a perfect setting and is fully equipped, clean and well mai … see more
Lakeside Villa Orlando, Luxury Villa with pool
Perfect spot

We have hired this villa before and the location is what we like.We do not like the hustle and bustle of International drive so this villa adj to the US102 is ideal for us.Located at Bass road its a 2 minute drive to a mega Walmart and all the stores … see more
Luxury Lakeside Villa with Hot Tub and Wireless Internet
Dream Villa

This is our second year at this villa and we could find nothing to fault, set on the side of a lake with swimming pool covered by Florida room ( mosquito netting) with heated hot tube, extensive games room, cable tv in all rooms extremely well fitt … see more
DORAL WOODS SECLUDED VILLA
Best Florida Villa - by far !!!

We have spent many many weeks at this villa and when it isn't available for our trips to Florida nothing we stay at compares !!! It is a great villa, owned by an owner who cares. Well equipped, south facing, very private, safe with a real florida f … see more
Florida Lets A Dream
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 conditioning controlled … see more

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