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Kissimmee

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449 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.

(16) Excellent 

22

Holiday villa with swimming pool in Bellavida Resort

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 £105 / night

£635 - £825 / week

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from £105 / night

(18) Very Good 

17

Holiday villa in Kissimmee City

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 £49 / night

£299 - £550 / week

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from £49 / night

(30) Excellent 

23

Holiday home with swimming pool in Oak Island Cove

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

Featured properties

(36) Excellent 

39

Villa rental in Kissimmee

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

(24) Very Good 

12

Villa rental in Lindfields 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 - £525 / week

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from £61 / night

(19) Very Good 

68

Holiday villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Thanks” This was a great Vila with everything you needed and in a good area to base yourself, if any c ok militants a bit dated  …see more

from £100 / night

£450 - £540 / week

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from £100 / night

(7) 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

(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

(43) Excellent 

91

Holiday villa in Westside

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 £105 / night

£725 - £925 / week

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from £105 / night

(18) 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 - £900 / week

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from £93 / night

(24) 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 £111 / night

£775 - £890 / week

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from £111 / night

(2) Excellent 

91

Villa accommodation in Kissimmee

Kissimmee / Kissimmee City

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fabulous 2 storey home with lots of space for large groups or 2 families, with cable t.v. in every room, wi fi and a games room. The pool & spa area is a great favourite with lots of loungers for relaxing by the pool. Seasons is one of the most sought after communit  …see more

from £90 / night

£600 / week

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from £90 / 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 £103 / night

£656 - £755 / week

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from £103 / night

(43) Excellent 

39

Westside 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

(15) Very Good 

18

Kissimmee 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 £64 / night

£450 - £500 / week

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from £64 / 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

(12) 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

(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

£559 - £675 / week

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from £80 / night

(21) Very Good 

26

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“very homely” Excellent location Close to airport.all parks and amenities. Would recommend this villa to anybody. Equipped with everything. Home from Home  …see more

from £50 / night

£350 - £725 / week

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from £50 / night

(4) Excellent 

23

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
“Fantastic House, Resort & Location” Fantastic, clean well maintained villa so near to Disney & Universal. We have just finished 22 days from 27th March to 18th April 2012 in the villa. The resort is idealy located just off of the 192, Wall Mart is  …see more

from £165 / night

£1155 - £1295 / week

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from £165 / night

23

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

5 13 1 night min

  • 5 bedrooms
  • Sleeps 13
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This new executive villa features state of-the-art living ... 5 bedrooms, 3.5 bathrooms, swimming pool and spa. Cumbrian Lakes is set in a conservation area yet only 5 minutes from shops and restaurants and less than 15 minutes to Disney World.The execut  …see more

from £105 / night

£735 - £980 / week

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from £105 / night

(29) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Comfortable villa in good location” We stayed for 4 nights to attend the Mecum Auto auction. The villa was spacious ,clean and reasonable to rent. Accessible to all Orlando attractions. Travelers need to bring everything, paper goods, coffee, cream  …see more

from £65 / night

£455 - £553 / week

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from £65 / 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

(10) Excellent 

13

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Point

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“fantastic and in a good position to explore the area” We have just got back from a wonderful two week stay at this villa.It's spacious and nicely decorated.The pool is a really good size and we used it everyday to cool off after a day at the parks.It'  …see more

from £90 / night

£600 - £680 / week

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from £90 / night

(48) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Excellent Location and a Wonderful Home.” Never booked through holiday lettings before so I was a bit nervous however I needn't have been. From the first moment I had contact with the owners of Russel Ridge communications and reassurance have been exc  …see more

from £100 / night

£425 - £700 / week

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from £100 / 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.<br />ALL PRICES QUOTED INCLUDE 13% FLORIDA TAXRefundable securi  …see more

from £116 / night

£812 - £1085 / week

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from £116 / night

(28) Excellent 

62

Holiday villa in Kissimmee

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Great Again!!” This is the second time that we stayed at this wonderful villa and, again, we were extremely thrilled! Nothing bad to report here! BTW...this probably won't be our last rental. We will be back.  …see more

from £80 / night

£525 - £675 / week

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from £80 / 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

(23) Very Good 

23

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 £80 / night

£550 - £1054 / week

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from £80 / 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

(67) 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

£475 - £590 / week

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from £70 / 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

(8) Excellent 

36

Holiday home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • Sleeps 13
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Well maintained fully furnished 5 bed 3.5 bath home with 25x15 heated private pool and spa. Private garden overlooking lake. Covered lanai with south facing sundeck and pool furniture. The fabulous sun drenched pool deck and shimmering waters of our private pool offer a  …see more

from £70 / night

£450 - £940 / week

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from £70 / 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 £123 / night

£861 / week

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from £123 / night

(32) Excellent 

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 £89 / night

£620 / week

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from £89 / night

(15) Excellent 

49

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Family friendly vacation home with screened in pool...immaculate and exactly as posted!” The home was very clean and had a fully functional and equipped kitchen. The bedrooms were each spacious and had sufficient linens. There is wi-fi and sufficien  …see more

from £91 / night

£595 - £677 / week

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from £91 / night

(17) Excellent 

23

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Fantastic house in a fantastic location” Recently returned from 2 weeks of fun in Florida with our 5 year old daughter. The weather was glorious and the parks brilliant. What topped our holiday was returning everday to our rented home. The home had a  …see more

from £66 / night

£406 - £877 / week

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from £66 / night

(18) Very Good 

36

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Indian Point with gorgeous lake and conservation view from pool.Indian Point, Kissimmee is a beautiful residential community situated within a few minutes drive of the Highway 192, convenient for the Wal-Mart superstore, a large selection of restaurants, and close t  …see more

from £70 / night

£450 - £575 / week

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from £70 / night

(19) Very Good 

20

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
“Dream home, brilliant location, very clean and well equipped.” From the first contact on enquiry to arriving back home 2 weeks later, the whole renting process and communication was outstanding, our family, 3 adults and 4 children aged 3,10,11 and16 a  …see more

from £130 / night

£875 / week

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from £130 / night

(12) 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 £90 / night

£590 / week

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from £90 / night

Top Destination reviews

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
Disney Davella - Luxury Villa - Pool and Jacuzzi
Excellent well equipped villa-very spacious and extremely clean

Well situated for all Disney Parks close to supermarket and several restaurants. We were a party of 7 with 2 children who adored the pool and jacuzzi. We felt the villa was exceptionally spacious and equipped with everything we could have needed. We … see more
Vista Lago
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 pool and deck area was a huge hit with the kids … see more