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

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Kissimmee
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14,892 Holiday homes

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

from£91 / night

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  • 3 Bedrooms
  • Sleeps 6

Kissimmee holiday villa rental

 (24)Excellent

Responds fast! avg. 1 hour 33 minutes

Certificate of Excellence

from£95 / night

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  • 4 Bedrooms
  • Sleeps 10

Westside holiday villa rental

 (55)Excellent

“Location! Location!” GREAT LOCATION of the Villa 5 minutes to Publix, 7 minutes to Target or Walmart, 15 from Disney, the house itself it is very comfortable and clean, big pool, all we needed for our vacation. If I had to book again I certainly would

Responds fast! avg. 16 minutes

Certificate of Excellence

from£96 / night

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  • 4 Bedrooms
  • Sleeps 9

Kissimmee holiday villa rental

 (15)Excellent

“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

Responds fast! avg. 3 hours 12 minutes

from£90 / night

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  • 3 Bedrooms
  • Sleeps 6

Villa rental in Kissimmee

 (45)Excellent

“Holiday To Remember” A perfect exciting, fantastic holiday with all the family. Family of 6. In the last week 7.Quality time with everyone.Extremely a special and magical holiday to remember.The villa was fabulous and very homely.Perfect from start t

Responds fast! avg. 1 hour 6 minutes

from£105 / night

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  • 4 Bedrooms
  • Sleeps 8

Holiday villa with swimming pool in Bellavida Resort

 (28)Excellent

“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

from£83 / night

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  • 4 Bedrooms
  • Sleeps 8

Holiday villa in Indian Creek

 (3)Excellent

“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

Responds fast! avg. 1 hour 57 minutes

from£75 / night

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  • 3 Bedrooms
  • Sleeps 6

Villa rental in Kissimmee

 (11)Very Good

“Comfy home from home” Situated in great location for my husband and myself. We love to be in central 192 and it must be here, so convenient for shopping and eating etc. peaceful community also. Home was comfy, would stay here again. Had a well equip

Responds fast! avg. 22 minutes

Certificate of Excellence

from£53 / night

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  • 3 Bedrooms
  • Sleeps 6

Holiday condo with golf nearby in Kissimmee

 (40)Very Good

“Great place to stay” Great location really close to Disney parks. Communication with owners was great with lots of information with directions to condo and everything we needed to know while we were staying in the condo. Clean and modern and great ame

Responds fast! avg. 3 hours 16 minutes

from£70 / night

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  • 4 Bedrooms
  • Sleeps 8

Holiday townhouse in Kissimmee

 (15)Very Good

“Wonderful vacation rental.” Great place to stay. Close to shopping and parks. House was very clean. Owner and management staff were so nice. Pool was clean and warm Refreshing after a long day at the parks. Would recommend this vacation home to my

Certificate of Excellence

from£50 / night

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  • 3 Bedrooms
  • Sleeps 6

Holiday villa in Kissimmee City

 (25)Very Good

“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

from£85 / night

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  • 4 Bedrooms
  • Sleeps 10

Kissimmee holiday villa let

 (6)Very Good

Responds fast! avg. 39 minutes

from£79 / night

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  • 3 Bedrooms
  • Sleeps 6

Holiday villa with swimming pool in Kissimmee

 (24)Excellent

“As good as it gets” From the first contact with the owner to our last day at the villa was excellent. The villa décor and facilities were just what we hoped for and more. From our location it was only a short trip to the theme parks eating out or shop

from£80 / night

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  • 4 Bedrooms
  • Sleeps 10

Holiday home in Kissimmee

 (28)Very Good

“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

from£165 / night

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  • 6 Bedrooms
  • Sleeps 12

Holiday villa with indoor pool in Paradise Palms

 (11)Very Good

“Beautiful and amazing place to stay--many thanks to Gira!” We stayed in this new and beautiful place for four nights recently. We are a group of six adults and two children. The place is huge, and everyone can have their comfortable stay after their

from£75 / night

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  • 4 Bedrooms
  • Sleeps 8

Holiday villa with swimming pool in Kissimmee

 (31)Very Good

Certificate of Excellence

from£90 / night

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  • 4 Bedrooms
  • Sleeps 8

Villa rental in Kissimmee with swimming pool

 (23)Excellent

Certificate of Excellence

from£75 / night

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  • 4 Bedrooms
  • Sleeps 8

Kissimmee holiday villa rental

 (33)Excellent

“FANTASTIC VILLA.....GREAT COMMUNICATION WITH OWNER” Lovely villa, spacious enough for 8 people and fully equipped. The location is lovely too, very quiet, with regular landscaping and nice views. The villa is approximately 2-3 miles from lots of res

Responds fast! avg. 1 hour 24 minutes

from£75 / night

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  • 4 Bedrooms
  • Sleeps 8

Villa accommodation in Kissimmee

 (27)Excellent

“Don't hesitate, it's lovely!” About to take our 8th Florida villa holiday we approached Dot who was helpful and prompt to reply. Knowing what a superb,convenient and safe location Cumbrian Lakes is we booked up. On arrival we were delighted with the v

Responds fast! avg. 2 hours 10 minutes

from£65 / night

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  • 3 Bedrooms
  • Sleeps 8

Holiday villa in Kissimmee

 (26)Very Good

“very homely” Excellent location Close to airport.all parks and amenities. Would recommend this villa to anybody. Equipped with everything. Home from Home

from£149 / night

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  • 6 Bedrooms
  • Sleeps 13

Kissimmee holiday villa let

 (24)Excellent

“Fabulous!” 2nd visit to 'Belleair' Villa at the lovely Bella Vida Resort. We enjoyed our stay so much the first time that we returned again this year! Fabulous, spacious accommodation (seven of us this year and eight last year) with quality furnishin

from£80 / night

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  • 4 Bedrooms
  • Sleeps 11

Holiday home in Crescent Lakes

 (42)Very Good

“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

from£229 / night

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  • 7 Bedrooms
  • Sleeps 16

Holiday villa in Formosa Gardens

 (10)Excellent

“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

from£100 / night

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  • 4 Bedrooms
  • Sleeps 10

Holiday home with swimming pool in Kissimmee

 (16)Very Good

“Merry christmas” We enjoyed our first ever family vacation over the holiday. The house was beautiful and very close to everything. It was a stress free stay and look forward to staying at this home in the future.

Certificate of Excellence

from£87 / night

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  • 4 Bedrooms
  • Sleeps 10

Holiday villa with swimming pool in Kissimmee

 (5)Very Good

Responds fast! avg. 39 minutes

from£72 / night

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  • 3 Bedrooms
  • Sleeps 6

Holiday villa rental

 (6)Very Good

Responds fast! avg. 56 minutes

Certificate of Excellence

from£70 / night

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  • 3 Bedrooms
  • Sleeps 8

Holiday villa in Kissimmee

 (88)Excellent

“Nice condo to stay with a family” Everything about this condo was accurate based on Debbie's description and previous reviews. Upon arriving, the binders with everything you need to know about the condo and the surrounding area were very helpful. Th

Responds fast! avg. 1 hour 56 minutes

Certificate of Excellence

from£78 / night

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  • 4 Bedrooms
  • Sleeps 10

Holiday villa rental

 (5)Very Good

Responds fast! avg. 1 hour 42 minutes

from£95 / night

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  • 4 Bedrooms
  • Sleeps 8

Kissimmee holiday villa rental

 (17)Excellent

“Perfect Villa” The villa was incredible. Big and spacious rooms, pool was great, games room was great, and had all amenities we needed.It is in a perfect location for Disney parks (15 mins), universal parks (20 mins), international drive (20 mins) and

from£115 / night

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  • 5 Bedrooms
  • Sleeps 10

Holiday home in Kissimmee

 (10)Excellent

“Wonderful holiday in a fantastic Villa!” This was our second family holiday to Orlando so we had an idea of what we were looking for from a villa and a location close to the parks. We considered a number of possible options before settling on Luce Del

from£99 / night

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  • 4 Bedrooms
  • Sleeps 8

Legacy Dunes Resort holiday condo rental

Responds fast! avg. 2 hours 16 minutes

from£79 / night

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  • 4 Bedrooms
  • Sleeps 8

Holiday villa in Kissimmee

 (10)Very Good

“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

from£65 / night

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  • 4 Bedrooms
  • Sleeps 8

Doral Woods holiday villa rental

 (17)Excellent

“Perfect for couples and families” I stayed here for 9 days with my husband and 5 month old daughter and we had lovely time! My husband and I had previously been to Florida and stayed in a property in Doral Woods so we knew we wanted to be in the same

Responds fast! avg. 1 hour 56 minutes

Certificate of Excellence

from£66 / night

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  • 4 Bedrooms
  • Sleeps 10

Villa rental in Indian Point

 (18)Very Good

“Outstanding Villa - Real Home from Home” Superb villa - really clean, airy and well-decorated with a lovely pool and patio area. Plenty of room for everyone in the 4 bedrooms & especially liked having 3 bathrooms to make leaving for the parks much qui

Responds fast! avg. 2 hours 32 minutes

Certificate of Excellence

from£90 / night

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  • 3 Bedrooms
  • Sleeps 6

Villa rental in Kissimmee with swimming pool

 (42)Excellent

“A beautiful home in the sun.” We stayed in this lovely villa for two weeks and we honestly could not fault it. The location is very good with easy access to Disney plus the i4 and the 192. There is a Walmart under 2 miles away and a number of great re

Responds fast! avg. 21 minutes

Certificate of Excellence

from£90 / night

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  • 4 Bedrooms
  • Sleeps 10

Villa rental in Kissimmee

 (68)Excellent

“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

from£100 / night

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  • 5 Bedrooms
  • Sleeps 12

Holiday villa in Kissimmee

 (26)Very Good

Responds fast! avg. 3 hours 19 minutes

Top Destination reviews

The Beautiful Life - Family Villa, 6 miles to Disney Pk
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. see more
The Road to "Mandyville"- Fantastic 3 Bedroom Villa
Honeymoon

Brilliant can't fault it at all, everything you need to hand, recommend this villa plenty of space great … see more
VILLAS AT ISLAND RESORT MINUTES FROM DISNEY
FANTASTIC HOME

me It's a Home away from Home. I had a fantastic stay, fully equipped with everything needed in a home, wish I could have stayed longer. Very close to Disney, many other exciting activities and of course shopping malls and outlets at my finger tips. I had the time of my life in the relaxing beautifully furnished home and would highly recommend to others thinking of going on a holiday. You would definitely enjoy the cozy home, club house with pool and spa. I really had a great time and will definitely be booking for my next trip next year. Thanks Irene. Keep up the good hospitality and quality of your home furniture and appliances. I have already spread the word to my family and friends. Hope you get a lot of future bookings. Good luck for the future. see more
The Perfect 6 Bed Resort Home,
Family Christmas Vacation 2017

The home was lovely. It felt like home away from home. Besides Property Management not answering 2 messages about the pool, everything was beautiful. Thanks for allowing my family into your home … see more
The Florida Pad
Very clean, fuctional and cozy home!

We are 5 person family with teen kids and stayed 5 days in dec-jan in the house. We loved the house, enough room for all of us, very well working wi-fi, all cooking utensils were in good shape etc. The pictures do not give the real picture, we think. Voimme suositella tätä taloa. Sijainti rauhallisella omakotitaloalueella. Lämmitetty uima-allas etc oma piha. Siistiä ja puhdasta. see more
Secret Key Villa for up to 8 guests
Emerald isles

We had a fab villa with heated pool. It was immaculate. Emerald isles is an easy location and is very well maintained … see more

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