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

Close

Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Villas and apartments in Kissimmee
Book with confidence.
Pay by card or PayPal, through the Holiday Lettings website, to be covered by Payment Protection. Never pay by bank or wire transfer.
✕

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

23,428 Holiday homes

(53) Excellent 

23

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“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.
…

Map

Add to shortlist

from £49 / night

£355 - £370 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from £49 / night

Book

(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.
…

Map

Add to shortlist

from £95 / night

£650 - £800 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from £95 / night

Book

(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!
…

Map

Add to shortlist

from £90 / night

£495 - £1,795 / week

Book View

from £90 / night

Book

(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,
…

Map

Add to shortlist

from £71 / night

£495 - £700 / week

Book View

from £71 / night

Book

(11) 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

Map

Add to shortlist

from £85 / night

£598 - £980 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from £85 / night

Book

(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.
…

Map

Add to shortlist

from £65 / night

£450 - £800 / week

Enquire View

from £65 / night

Enquire

(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

Map

Add to shortlist

from £95 / night

£525 - £650 / week

Book View

from £95 / night

Book

(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

Map

Add to shortlist

from £75 / night

£450 - £525 / week

Book View

Responds fast!
avg. 1 hour 0 minutes

from £75 / night

Book

(13) Average 

Certificate of Excellence

100

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

Map

Add to shortlist

from £130 / night

£910 / week

Book View

from £130 / night

Book

(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

Map

Add to shortlist

from £96 / night

£700 - £800 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £96 / night

Book

(30) Excellent 

Certificate of Excellence

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!
…

Certificate of Excellence

Map

Add to shortlist

from £68 / night

£475 - £550 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from £68 / night

Book

(1) Excellent 

0

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

Map

Add to shortlist

from £200 / night

£1,400 / week

Book View

from £200 / night

Book

(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

Map

Add to shortlist

from £80 / night

£475 - £745 / week

Book View

from £80 / night

Book

(6) Average 

34

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

Map

Add to shortlist

from £87 / night

£605 - £825 / week

Book View

from £87 / night

Book

(14) Very Good 

50

Holiday villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

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

Map

Add to shortlist

from £85 / night

£550 / week

Book View

from £85 / night

Book

(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

Map

Add to shortlist

from £103 / night

£668 - £908 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from £103 / night

Book

(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

Map

Add to shortlist

from £229 / night

£1,600 - £2,100 / week

Enquire View

from £229 / night

Enquire

(34) Very Good 

Certificate of Excellence

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
“Our stay” Loved it, very clean and had everything we needed. Would definitley recommend, 10 mins from disney 2 mins from shops/ restaurants whilst still being in a very quiet street.
…

Certificate of Excellence

Map

Add to shortlist

from £85 / night

£495 - £595 / week

Book View

Responds fast!
avg. 2 hours 23 minutes

from £85 / night

Book

(32) Excellent 

Certificate of Excellence

26

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

Certificate of Excellence

Add to shortlist

from £80 / night

£490 - £680 / week

Book View

Responds fast!
avg. 3 hours 32 minutes

from £80 / night

Book

(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

Map

Add to shortlist

from £54 / night

£380 / week

Book View

from £54 / night

Book

(4) Excellent 

51

Holiday villa in Kissimmee

Kissimmee / Hamilton's Reserve

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 85 km
  • Swimming pool

Map

Add to shortlist

from £122 / night

£727 - £1,018 / week

Book View

from £122 / night

Book

(6) Very Good 

51

Kissimmee holiday apartment rental

Central Florida / Kissimmee

3 6 3 nights min

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

Map

Add to shortlist

from £67 / night

£468 / week

Book View

from £67 / night

Book

(14) Excellent 

22

Kissimmee holiday villa let

Central Florida / Kissimmee

4 8 min stay varies

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

Map

Add to shortlist

from £106 / night

£743 / week

Book View

from £106 / night

Book

(20) Very Good 

90

Holiday townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

Map

Add to shortlist

from £100 / night

£600 - £750 / week

Book View

from £100 / night

Book

(32) 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

Map

Add to shortlist

from £105 / night

£635 - £825 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from £105 / night

Book

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

Map

Add to shortlist

from £215 / night

£1,450 / week

Book View

Responds fast!
avg. 1 hour 48 minutes

from £215 / night

Book

(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

Map

Add to shortlist

from £256 / night

£786 - £2,113 / week

Book View

from £256 / night

Book

(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

Map

Add to shortlist

from £65 / night

£450 - £765 / week

Book View

from £65 / night

Book

(3) Average 

12

Kissimmee holiday townhouse rental

Kissimmee / Terra Verde Resort

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

Map

Add to shortlist

from £60 / night

£385 / week

Book View

from £60 / night

Book

(2) Very Good 

18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

Map

Add to shortlist

from £171 / night

£1,200 / week

Book View

from £171 / night

Book

(51) 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.
…

Map

Add to shortlist

from £106 / night

£735 - £904 / week

Book View

Responds fast!
avg. 1 hour 16 minutes

from £106 / night

Book

(32) Very Good 

22

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

Map

Add to shortlist

from £59 / night

£350 - £465 / week

Enquire View

from £59 / night

Enquire

(36) Excellent 

Certificate of Excellence

56

Kissimmee holiday villa rental

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Swimming pool
“Fantastic first visit to florida” When we arrived the first walk around the villa was greeted with "oh my god it's amazing! " Great size and space In really good condition Great pool and outdoor area with all day sun - great sunset and great bbq Great location on a lake with varied wildlife and not too close to neighbours. Great games room - used every day by kids. Pretty much everything in the villa you'd need Not too far from all major attractions and conveniences
…

Certificate of Excellence

Map

Add to shortlist

from £110 / night

£745 - £950 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £110 / night

Book

(46) Very Good 

Certificate of Excellence

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

Certificate of Excellence

Map

Add to shortlist

from £65 / night

£455 - £630 / week

Book View

from £65 / night

Book

(43) Excellent 

30

Villa rental in Cumbrian Lakes

Kissimmee / Cumbrian Lakes

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
“Home away from home” We picked this house as it had everything we needed when traveling with young childern and was large enough for families. Andrew was great to work with, answered all of my questons and everything he promised was at the house. Thanksf for helping me with my family vacation!
…

Map

Add to shortlist

from £110 / night

£750 - £900 / week

Enquire View

from £110 / night

Enquire

(20) Excellent 

Certificate of Excellence

30

Kissimmee holiday villa let

Kissimmee / Lindfields

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

Map

Add to shortlist

from £70 / night

£445 - £595 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from £70 / night

Book

(22) Very Good 

51

Apartment rental in Kissimmee

Central Florida / Kissimmee

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Map

Add to shortlist

from £67 / night

£460 / week

Book View

from £67 / night

Book

(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

Map

Add to shortlist

from £335 / night

£2,345 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from £335 / night

Book

(22) 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.
…

Map

Add to shortlist

from £70 / night

£485 - £599 / week

Book View

Responds fast!
avg. 35 minutes

from £70 / night

Book

(20) Excellent 

Certificate of Excellence

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

Certificate of Excellence

Map

Add to shortlist

from £85 / night

£595 - £840 / week

Book View

from £85 / night

Book

Top Destination reviews

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
Florida Jewels
Florida jewels

Just come home from our visit to this villa . We were thrilled with the villa it was lovely , very clean and well equipped, very well presented and spacious. Pool was cleaned regular . Great central location with shops and restaurants near by . The lady owner was a pleasure to deal with and responded to any questions very promptly .We will definitely be going back . … see more
Magical Vacations 4-bed Villa with Private Pool and Air Conditioned Games Room
Fantastic !!

Villa was fantastic , couldn't have asked for a nicer place to stay , couldn't fault anything about it , would happily stay there again and highly recommended it to anyone else. … see more
Superb 4 Bedroom Villa, Beautiful Lake View, Kissimmee, Florida
Brilliant villa

This was our second stay at this villa, and have already booked again for next year ,we had a great holiday again and would not hesitate to recommend this villa to anyone wanting a great villa that is spotlessly clean very comfortable perfectly located for all parks and shops and the nicest owner in Rose you could possible want to deal with ,can not wait for next year thanks again Rose xx … see more

Also consider