Villas in Kissimmee and Apartments - Holiday Lettings - Holiday Rentals Kissimmee

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23,569 Holiday homes

(1) Excellent 

17

Holiday villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool

from £172 / night

£1,200 / week

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from £172 / night

(30) 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
“Extremely comfortable with everything you need for your stay.” We have stayed at this villa on numerous occasions, and will continue to return in the future. The villa is situated in a quiet residential area, close to all local amenities such as shops, restaurants, and attractions. The location is also a reasonably quick drive from both of Orlando's airports. The villa is extremely comfortable, fully furnished in an American style to get you in the mood for your holiday. There are three bedrooms, one en suite, a large family room with cable TV, dining room, well equipped laundry room and table hockey and pool table in the spacious garage. Along with the computer games, there is plenty to keep the kids occupied if you decide to have a night in. The swimming pool is ideal for all ages and is screened from the others by well kept bushes and plants. The pool has stepped access at the shallow end, and gradually slopes to the deeper side. As already stated, local supermarkets are just a short drive away, where you can mix with the real Americans, who are all very polite and very friendly. It's easy and cheap to buy the essentials for your stay at these shops. The villa is also ideally situated for the theme parks, being only about 10 / 12 miles from Disney and can be accessed on a direct route from the villa. This road is a a joy to drive as it is well signposted and despite there being three lanes for traffic, the roads are normally very quiet. In fact, getting around the whole area is very easy in deed. I would highly recommend this villa as a holiday location, not only for the facilities provided, but also for the helpful, friendly service provided by the holiday villa owners who have been a joy to deal with,and I look forward to dealing with them again in the future. You will no be disappointed.

from £65 / night

£450 - £800 / week

Enquire View

from £65 / night

(8) Excellent 

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £45 / night

£320 - £340 / week

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Responds fast!
avg. 2 hours 42 minutes

from £45 / night

(51) Very Good 

23

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly

from £49 / night

£245 - £370 / week

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Responds fast!
avg. 3 hours 26 minutes

from £49 / night

(50) Excellent 

91

Holiday villa in Westside

Kissimmee / Westside

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Highly recommended - Great place with all you need” Took the family to Disney for a few days in March and found Lee's place on VRBO - first time we use this service. This home is amazing, the whole family loved the pool, hot tub, games room, and overall comfort. Nice quiet neighborhood, tons of restaurants very close by. We went to Magic Kingdom and Animal Kingdom, and both were about 15 minutes away. Special thanks to Lee who was extremely kind and helpful, walking me through the VRBO process as well as providing advice on how to make the best of our Disney visits. Will definitely reach out again next time we plan a Disney trip.

from £103 / night

£712 - £875 / week

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Responds fast!
avg. 1 hour 16 minutes

from £103 / night

(31) Excellent 

33

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly

from £80 / night

£490 - £680 / week

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Responds fast!
avg. 2 hours 16 minutes

from £80 / 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

from £99 / night

£647 - £879 / week

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Responds fast!
avg. 1 hour 51 minutes

from £99 / night

14

Kissimmee holiday condo rental

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £76 / night

£528 / week

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from £76 / night

(20) Excellent 

18

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“We will not be going anywhere else!” This was our second stay at the beautiful villa. Local to all the best restaurants, Wall-Mart and Target for food shops. With only a 15 minute drive we were in the theme parks, International Drive and only 45 minutes from Lego Land. The views from the pool across the lakes are so relaxing, a peaceful location and private. With plenty of room for the whole family, all the rooms are kitted out to a high standard, themed for the kids as well! We will not be looking for anywhere else when we return, only here!

from £90 / night

£495 - £1,795 / week

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from £90 / night

(28) Excellent 

21

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“The best villa we've ever had!” We have been visiting Florida since 2000 and this is definitely the cleanest, most comfortable villa we have ever stayed in. There was nothing else that we could have asked for - it really was a home away from home! The area was lovely and quiet, the local neighbours were friendly and it was the perfect distance from the main attractions. There are not many places you can sunbathe and watch an alligator sunbathing at the same time! Would definitely reccommend and hope to return soon! Thank you for taking such good care of your property!

from £65 / night

£450 - £550 / week

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Responds fast!
avg. 3 hours 20 minutes

from £65 / night

(19) Excellent 

30

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £96 / night

£700 - £800 / week

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Responds fast!
avg. 3 hours 25 minutes

from £96 / night

(46) Very Good 

12

Villa rental in Lindfields

Kissimmee / Lindfields

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £65 / night

£455 - £630 / week

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from £65 / night

(3) Average 

81

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £150 / night

£1,050 - £1,120 / week

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Responds fast!
avg. 1 hour 30 minutes

from £150 / night

(37) Very Good 

36

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £75 / night

£450 - £525 / week

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Responds fast!
avg. 2 hours 21 minutes

from £75 / night

(45) Excellent 

28

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
“Fantastic Top Quality Home” Immaculate house with plenty of room, the rooms had everything we needed. This property has gone beyond a standard rental as has everything you need from toys for pool, beach towels, baby accessories to waterproof ponchos for wet days! Nothing had not already been thought of. Definitely will be booking again and highly recommend to anyone. It was easy to find in a secluded cul de sac location not far from all main routes.

from £133 / night

£837 - £1,103 / week

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Responds fast!
avg. 3 hours 23 minutes

from £133 / night

(54) Excellent 

Certificate of Excellence

39

Villa rental in Kissimmee

Central Florida / Kissimmee

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“An excellent holiday with fantastic accommodation.” Our family stayed here whilst holidaying in Orlando this year, and the accommodation was absolutely superb. The location is not too far from all the Disney/Universal and Seaworld attractions and also easy access to routes to the east coast (Kennedy space center). All amenities at the villa were spot on, with the pool being both big enough for adults and safe enough for children, with the added bonus that there are water toys for the children located in the garage, and the pool itself is secluded. The property itself is in a beautiful estate, which we walked around as it was scenic and all the residents were so cheerful and helpful, (with the added bonus of a state trooper living right across the street). The local eateries are clean and cheap, with great service. We thoroughly recommend this villa and will definately be staying here again. Thank you for making our holiday that extra special, we look forward to coming next year.

Certificate of Excellence

from £90 / night

£545 - £585 / week

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Responds fast!
avg. 35 minutes

from £90 / night

12

Kissimmee holiday villa rental

Kissimmee / Trafalgar Village

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £80 / night

£559 / week

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Responds fast!
avg. 3 hours 45 minutes

from £80 / night

(25) 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
“The house is in an amazing location, in a quiet enough location to relax but not too far away from disney or universal” Great place to stop, in a quiet enough area to get some much needed RNR but also only 20 minutes away from the disney and universal parks,

from £71 / night

£495 - £700 / week

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from £71 / night

(12) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £135 / night

£945 - £1,155 / week

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from £135 / night

(5) Very Good 

33

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £87 / night

£607 / week

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from £87 / night

(22) Excellent 

28

Kissimmee holiday villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 75 km
  • Swimming pool
“Very Nice Property” Property well situated, clean and modern, Nice size pool,all of group pleased with choice Be prepared to pick the bins up every morning as the wildlife enjoy going through them in the nights.

from £95 / night

£650 - £800 / week

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Responds fast!
avg. 3 hours 7 minutes

from £95 / night

(5) 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

from £54 / night

£380 / week

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from £54 / night

(5) Excellent 

16

Villa rental in Kissimmee

Kissimmee / Indian Ridge

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £115 / night

£700 - £875 / week

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from £115 / night

(93) Excellent 

Certificate of Excellence

25

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
“The best place to stay in Orlando!!!!” This villa is excellent in every respect. It is well positioned for travel to the many attractions in Florida as well as the local Kissimmee town. The villa itself is spacious, modern with all the facilities that you could need, and is immaculate. The heated swimming pool at the rear of the property was also a great start to the day regardless of the weather. Finally, the owners present and manage this property in way that takes the stress away from your holiday. We really had a great time - many thanks to the owners, we'll definitely be looking to go back!!

Certificate of Excellence

from £70 / night

£485 - £600 / week

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Responds fast!
avg. 1 hour 48 minutes

from £70 / night

(14) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £64 / night

£445 - £598 / week

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from £64 / night

(60) Excellent 

41

Holiday villa in Crescent Lakes

Kissimmee / Crescent Lakes

3 7 5 nights min

  • 3 bedrooms
  • sleeps 7
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“COULD LIVE THERE ALL YEAR ROUND” We knew the area having stayed nearby on holiday about 8 years ago. It is a 15 minute drive away from the busy Highway 192 where restaurants and shops are located and it is an easy drive to the peace and quiet of the Crescent Lakes. Lakeside Villa is a lovely spacious 3 bedroomed on the level villa with 2 lounges and 2 bathrooms. It has a great pool area with marvelous open views of the lake and gets the sun from early morning to last thing at night. Properties at either side are set back and their pool areas are screened from view so the only persons overlooking are the other side of the lake. The pool deck is spacious with a large shaded area to dine out of the sun or relax on one of the four loungers. Free pool heat is a great bonus and was set at a generous temperature. The jacuzzi section of the pool has a renter operated heating switch enabling it to be heated separately for late evening relaxation. With a great selection of wildlife around the lake we found ourselves reluctant to leave the comfort of our poolside. Free wifi, a safe and a house security system all helped to make our 26 night stay feel like a home from home. If only we had the sunshine. pool, wildlife, good roads, cheap dining out and loads of entertainment options available in Orlando. Lakeside Villa is a great value rental and I only hope I haven't oversold it cos' we hope to return. Almost forgot to mention that the owner, Peter, was extremely efficient in his handling of our booking and was easily able to be contacted.

from £96 / night

£666 / week

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Responds fast!
avg. 43 minutes

from £96 / night

(1) Excellent 

20

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

8 17 min stay varies

  • 8 bedrooms
  • sleeps 17
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £248 / night

£761 - £2,046 / week

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from £248 / night

(3) Very Good 

18

Holiday villa letting

Central Florida / Kissimmee

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £90 / night

£630 - £875 / week

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Responds fast!
avg. 1 hour 30 minutes

from £90 / night

(3) Excellent 

39

Holiday villa rental

Central Florida / Kissimmee

8 18 3 nights min

  • 8 bedrooms
  • sleeps 18
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £335 / night

£2,345 / week

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Responds fast!
avg. 1 hour 50 minutes

from £335 / night

(11) Excellent 

26

Holiday villa in Formosa Gardens

Kissimmee / Formosa Gardens

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £229 / night

£1,600 - £2,100 / week

Enquire View

from £229 / night

(22) Very Good 

42

Villa rental in Indian Point

Kissimmee / Indian Point

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £92 / night

£644 - £763 / week

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from £92 / night

(21) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Top villa” A fantastic villa with a woodland setting. We really enjoyed staying in Doral Woods. The rear of the villa was completely private and the wildlife in the area made for fascinating viewing. There was plenty of room inside the villa and the pool area was clean and welcoming.

from £70 / night

£485 - £599 / week

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Responds fast!
avg. 39 minutes

from £70 / night

(17) Excellent 

34

Holiday villa in Hamilton's Reserve

Kissimmee / Hamilton's Reserve

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool

from £105 / night

£735 - £1,130 / week

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Responds fast!
avg. 3 hours 15 minutes

from £105 / night

(60) Excellent 

Certificate of Excellence

45

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
“Great clean villa to stay in, would stay there again.” A lovely villa and above all clean.Close to all the parks I coulnt have stayed in a better place. Not far from the 192 which is the main highway to all the Disney+Universal parks. The added bonus was having a pool in the villa for days when we simply wanted to relax.

Certificate of Excellence

from £95 / night

£575 - £900 / week

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Responds fast!
avg. 51 minutes

from £95 / night

(26) Excellent 

32

Holiday villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“3 weeks of luxury” I have just arrived back in the UK from a fantastic 3 weeks in this Villa and am already looking at booking it again for next year. Excellent location in terms of parks, shops, places to eat and night time peace. Lovely clean, spacious and inviting home which makes a perfect end to an exhaustive day walking around the theme parks all day. Me and my partner loved sitting at the pool overlooking the lake with all the wildlife including turtles, large birds, deer and the occasional alligator. Great holiday and thank you so much for letting me and my family stay over.

from £85 / night

£495 - £595 / week

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Responds fast!
avg. 2 hours 4 minutes

from £85 / night

(11) Excellent 

37

Holiday home rental

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £65 / night

£450 - £765 / week

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from £65 / night

(15) 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

from £80 / night

£475 - £867 / week

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from £80 / night

(3) Excellent 

17

Holiday home in Kissimmee

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £117 / night

£1,061 / week

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Responds fast!
avg. 1 hour 12 minutes

from £117 / night

(14) 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” The condo is perfectly positioned for a Disney world. It took us 15 mins to get to world drive. We had a fantastic holiday. The children swam in the pool everyday and the condo was excellent with a beautiful view of the lake. Mary, the owner was very helpful and made the holiday that much better. Many thanks.

from £60 / night

£420 - £550 / week

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Responds fast!
avg. 2 hours 27 minutes

from £60 / night

(22) Excellent 

24

Holiday villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £100 / night

£695 - £895 / week

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Responds fast!
avg. 1 hour 45 minutes

from £100 / night

Top Destination reviews

Affordable and Luxurious Ground Floor Condo at Cane Island Resort
Our stay at the appartment

The apartment was lovely . My party of 4 went wow when we walked in, it was spotlessly clean, spacious and had everything needed for a 3 week stay. The decor was lovely, I'd live in it. It felt safe being in a gated complex, the pool was good and hubby used the gym many times. Very close to 192 and nearby shops in walking distance, car recommended, took 15 mins to Disney. I would definitely stay here again and recommend to family and friends. Excellent.see more
Indian Ridge Villa includes a Grill, Pool, and Hot Tub
Family holiday

The house is perfect for a family holiday situated very close to Disney. Close to shoping etc, has everything you need large pool jacuzzi.there is nothing you need that is not in the house, could do with a little tlc , but it is a holiday home so I suppose it is as expected very good. … see more
Amazing Disney Condo, Pool & Hot tub Onsite
Fantastic! Highly recommend but please don’t book our dates!

We stayed for two weeks in peak season for a very reasonable price considering the facilities and quality of the accommodation. The pictures do not do justice to the lovely interior, which is light, well furnished and very comfortable and clean. We enjoyed having breakfast on the balcony and a drink while the kids were in bed. The pool is a two minute walk with a great little bar and club house and our daughters enjoyed spending time here away from the parks. Location is fantastic - Disney is just a 10 minute drive away and is so easy to get to from the condo and a wide variety of restaurants are just a 5 minute drive away. Walmart is also a 5 minute drive away. Communication with the owner was absolutely fantastic and they were helpful and very quick to reply to any queries. We would definitely stay again and would recommend without hesitation to people who can manage the stairs with luggage (just two short flights) and wish to stay in a safe gated community which is very pretty and pleasant, without a silly price tag! We were surprised at how quiet the area was and we never heard any noise other than grass cutters or cleaners keeping the communal areas well kept. The girls found their bedrooms a little warm so we left the doors open and that seemed to do the trick then when we were packing for home we found the fans that are provided! The Master bedroom has a ceiling fan and the air conditioning is great in the living areas. It was hot outside but we were comfortable inside. We really didn’t want to come home and I will miss the fantastic washer and dryer! Thankyou to Pam and Roland for letting us stay.see more
Robson's Retreat, Relaxing Vacation Home with a Ba
Perfect vacation place for our family

Better than a home away from home. Very modern and clean. More things to entertain the family than you would ever need. Safe and relaxing location close to many restaurants and shops. We didn't want to leave. … see more
Belleair
Florida Holiday, Belleair

A brilliant villa with a great pool and space for the children to play. The decor is excellent and location is the best. I can not recommend too highly. … see more
Star Lake Villa, close to Disney with pool
Fantactic

Villa is perfectly placed for Disney parks, spotlessly clean, everything you could need. Close to a huge Wal-Mart plus all designer villages and lots of restaurants Perfect holiday xx … see more