Villas and apartments in nightlife areas | Holiday Lettings

Close

View larger map

Also consider

North America Holidays
172843 properties
United States Holidays
128205 properties
Florida Holidays
39567 properties
Central Florida Holidays
16074 properties
Emerald Isle Kissimmee
50 properties
Villas Windsor Hills Resort
29 properties
Kissimmee City
28 properties
Villas Paradise Palms
20 properties
Villas Windsor Palms
19 properties
Cumbrian Lakes
18 properties
Lake Berkley
18 properties
Lindfields
17 properties
Bellavida Resort
15 properties
Terra Verde Resort
15 properties
Crescent Lakes
10 properties
Compass Bay
10 properties
Seasons Resort
10 properties
Villas Formosa Gardens
9 properties
Venetian Bay Villages
9 properties
Doral Woods
8 properties
Villas Orange Lake Resort
8 properties
Trafalgar Village
8 properties
Encantada Resort
7 properties
Eagle Pointe
6 properties

Kissimmee

No dates Enter dates for accurate prices -

Adults, Children

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

155 Holiday homes

Filters applied: Nightlife

(45) 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
“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 over
…see more

from £104 / night

£716 - £885 / week

Book View

from £104 / night

(37) Very Good 

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 £99 / night

£675 / week

Book View

from £99 / night

(19) Very Good 

17

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • 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 - £700 / week

Book View

from £60 / 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

from £143 / night

£997 / week

Book View

from £143 / night

(30) Very Good 

24

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
“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
…see more

from £35 / night

£219 - £375 / week

Book View

from £35 / night

(14) Excellent 

23

Kissimmee holiday home rental

Kissimmee / Windsor Palms

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Fantastic Villa, Perfect Location for Disney etc., Food & Shopping” It was a very straightforward process booking 'Mickey's Clubhouse', questions were answered very promptly by the owners - the whole process was quick, efficient and informative.The vi
…see more

from £115 / night

£875 / week

Enquire View

from £115 / night

(19) Excellent 

24

Holiday villa letting

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“Fantastic!” This was like home from home , clean , beautiful furnished,very relaxing, child friendly, lovely veiws from pool ect, can't wait to go back.
…see more

from £70 / night

£460 - £600 / week

Book View

from £70 / night

(14) 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
“Wyndham Palm Way review” Lovely villa, easy to find just off the 192 and easily accommodates 9 people so perfect for a large family holiday. Easy to get to the parks and out for food but you will need a car. Good value for money although it is a li
…see more

from £93 / night

£650 - £700 / week

Book View

from £93 / night

(5) Excellent 

28

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
“Super Spring Break” My family spent the week of April 7 - 14, 2012 at "Jewel In The Crown", which is located in Emerald Island Resort. This is our sixth trip to Orlando and one of the best times we've had!!! Our "home away from home" was comfortable,
…see more

from £154 / night

£1072 / week

Book View

from £154 / night

(21) 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
“I would return to this villa anytime” location was great, attractions within easy reach, restaurants and shops within easy reach, very clean villa with plenty of everything, pool was clean and inviting, loved it.
…see more

from £65 / night

£450 - £500 / week

Enquire View

from £65 / night

(27) Excellent 

56

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“On the booking with Steve” Steve has kindly been answering my questions and helped me make my decision to want to stay at his beautiful villa looks stunning
…see more

from £125 / night

£850 - £975 / week

Book View

from £125 / night

(46) 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
“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
…see more

from £100 / night

£595 - £925 / week

Book View

from £100 / night

(8) Excellent 

43

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee / Winward Cay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 condition
…see more

from £66 / night

£460 - £650 / week

Book View

from £66 / night

(12) Very Good 

62

Coral Cay holiday home rental

Kissimmee / Coral Cay

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
“A Nice Stay!!!!” We really loved it and we wish if we would have stayed. Beautiful scenic, nice backyard overlooking the lake. The pool was nice with a hot pool
…see more

from £59 / night

£413 / week

Book View

from £59 / night

(14) Excellent 

24

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
“Lovely villa, great service and excellent location for all the Disney parks!” Definitely recommended! From the moment I enquired about the villa, (we dealt directly with the owner) we received excellent service. Booking was easy, and we were supplie
…see more

from £90 / night

£580 - £775 / week

Enquire View

from £90 / night

(16) Excellent 

27

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Perfect location for Disney and we couldnt fault the villa which was spacious, clean and well equipped, thank you” We had a wonderful stay in this modern, spacious and well equipped villa which we found to be ideally placed for Disney We also visited
…see more

from £75 / night

£525 - £625 / week

Book View

from £75 / night

(9) Excellent 

22

Holiday home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £52 / night

£331 - £516 / week

Book View

from £52 / night

(20) 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

Book View

from £105 / night

(17) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £85 / night

£558 - £635 / week

Book View

from £85 / night

(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

from £60 / night

£385 / week

Book View

from £60 / night

(5) Excellent 

Certificate of Excellence

24

Kissimmee holiday home accommodation

Kissimmee / Lindfields

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Pete and Louise” I felt like I was at home !!!!! Everything I needed and could have forgotten was already there......this place was immaculate! It was close tho so many things to do and shopping as well......I will be back again real soon for sure, th
…see more

Certificate of Excellence

from £50 / night

£335 - £350 / week

Book View

from £50 / night

(13) Excellent 

18

Kissimmee holiday villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 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 minut
…see more

from £90 / night

£495 - £625 / week

Book View

from £90 / night

(13) Very Good 

Certificate of Excellence

47

Villa rental in Indian Point with shared pool

Kissimmee / Indian Point

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“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
…see more

Certificate of Excellence

from £66 / night

£460 - £690 / week

Book View

from £66 / night

(47) Excellent 

21

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!” We Stayed at Doral Woods villa in May 16. The villa is equipped with everything you need and is spotlessly clean. Beautiful pool & garden the best villa we have ever stayed in! Highly recommend also the owners are so helpful and attentive
…see more

from £130 / night

£895 - £995 / week

Book View

from £130 / night

(3) Excellent 

61

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
“Luxury in the sun” Home from home - if home had all these mod cons and a heated pool outside the lounge and a games room in the garage. Great location for Disney assuming you have a car. Plenty of local restaurants and easy run to NASA. Onsite centr
…see more

from £115 / night

£690 - £1350 / week

Book View

from £115 / night

(38) 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
“Mrs” EXCELLENT...doesn't do it justice. Great location Great accommodation Great facilities Would have liked to have stayed longer. A lot of thought and care has gone into making this your home for your stay. Disney is easy to access.... food shops
…see more

from £80 / night

£550 - £675 / week

Book View

from £80 / night

(1) Very Good 

22

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £93 / night

£647 / week

Book View

from £93 / 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

from £80 / night

£475 - £745 / week

Book View

from £80 / night

(2) Excellent 

70

Holiday villa letting

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool

from £95 / night

£665 - £875 / week

Book View

from £95 / night

(6) Excellent 

Certificate of Excellence

27

Kissimmee holiday villa rental

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool

Certificate of Excellence

from £140 / night

£930 - £1130 / week

Book View

from £140 / night

(3) Very Good 

20

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“a good place to relax at the end of an energetic day” Martin's Villa was well equipped and spacious, the pool was screened which helped with privacy. It is on an estate with a mix of residents and some holiday makers and is very convenient for a lar
…see more

from £81 / night

£566 / week

Book View

from £81 / night

(25) Very Good 

27

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
“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

£525 - £1054 / week

Book View

from £80 / 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 value and great location!” Lovely apartment, really comfortable and spotlessly clean. We received 2 parking passes and there was always parking available at the door. Complex is quiet, secure and nicely landscaped, pool area is great. Locati
…see more

from £50 / night

£350 - £450 / week

Book View

from £50 / night

(6) Excellent 

24

Holiday villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Comfortable, smart, spacious, well equipped villa.” We stayed as two family groups comprising 8 Adults and 2 kids. The accommodation was flexibly arranged and everyone could find there own space when they wanted it. The villa's own pool and hot tub w
…see more

from £165 / night

£1155 / week

Book View

from £165 / night

(1) Very Good 

20

Condo rental in Kissimmee with golf nearby

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £69 / night

£443 - £654 / week

Book View

from £69 / night

(18) 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
“Absolutely wonderful!” This house is amazing! The pictures do not capture the true beauty of this property. We traveled with 3 families - all ages. There was plenty of room for everyone - bedrooms, kitchen, living room, family room, pool, etc. The
…see more

from £149 / night

£1045 - £1495 / week

Book View

from £149 / night

(10) 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

from £94 / night

£610 - £930 / week

Book View

from £94 / night

(9) Excellent 

88

Kissimmee holiday villa rental

Kissimmee / Bellavida Resort

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Nearest beach 111 km
  • Swimming pool
  • Child friendly
“Our vacation in Florida 2014” The location of the property was ideally suited for our planned vacation. The size and facilities were extremely good and especially with 6 adults & 4 children it worked perfectly with each family. The kitchen lent itsel
…see more

from £174 / night

£1217 - £1449 / week

Book View

from £174 / night

(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
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a
…see more

from £171 / night

£1200 / week

Book View

from £171 / night

(7) Excellent 

98

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Perfect” This villa was excellent (exactly as advertised). The location was great being only 10-15 minutes from Walt Disney World. It was perfectly positioned for shopping too, Walmart was only a few minutes away. The kids loved their bedrooms and
…see more

from £77 / night

£539 - £803 / week

Book View

from £77 / night

1