15 Best Vacation Rentals in Kissimmee City - Holiday Lettings - Cabins

Close

>
>
>
>
>
>
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.

Kissimmee City

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

16,785 Vacation rentals

(25) Very Good 

23

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
A 3 bedroomed villa which sleeps 6. Approximately 3 miles Disney. Own screened swimming pool with large decking area with gas barbecue with patio furniture and loungers. The villa inside is decorated with blinds and window pelmets. 3 TV's all with cable, VCR and a Mu …see more

Map

Add to shortlist

from $86 / night

$497 - $703 / week

Inquire View

from $86 / night

Inquire

“Magnificent Accomadation”

Reviewed 23 May 2012

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 w… More

“Brilliant, beautiful worth EVERY penny”

Reviewed 31 Aug 2011

We have stayed at this villa every year since 2009 and have already booked it for 2012. Very close to Disney and Old Town in Kissimmee. Highly recommend it I have had several friends who have also hir… More

“Nice homely atmosphere.”

Reviewed 24 Jan 2012

This is a nice villa in a good location. You are close enough to everything to get there within a few mins drive. The estate the villas is in is quiet & peaceful with the villa having a homely atmos… More

See all reviews

(14) Excellent 

25

Vacation villa in Kissimmee City

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
Living Area Our recently upgraded and spacious lounge is the ideal place to just relax after a hard day at the theme parks! The comfortable lounge benefits from a 42" LCD HD cable television with DVD, video-player, Playstation 2 and a selection of children's videos and …see more

Map

Add to shortlist

from $157 / night

$852 - $1,648 / week

Book View

Responds fast!
avg. 1 hour 34 minutes

from $157 / night

Book

(1) Very Good 

20

Condo rental in Kissimmee City with golf nearby

Kissimmee / Kissimmee City

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 100 mi
  • Swimming pool
This spacious 3 bedrooms and 2 bedrooms vacation home includes the Following Amenities: 4 miles to Disney , 1 King Bed, 1 Queen Bed, 2 Twin Beds, COMMUNITY has heated pool, spa, fitness center, theater room, basketball and tennis court and children playground, Complemen …see more

Map

Add to shortlist

from $90 / night

$630 - $850 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from $90 / night

Book

(3) Excellent 

91

Villa accommodation in Kissimmee City

Kissimmee / Kissimmee City

5 10 6 nights min

  • 5 bedrooms
  • Sleeps 10
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful 5 bed villa in Kissimmee, Florida, the holiday destination of the world. Just 10 minutes from Disney in one of the most sought after communities in Orlando. Our villa is luxuriously furnished, with its own secluded pool & spa, a fabulous games room and minutes …see more

Map

Add to shortlist

from $184 / night

$1,283 / week

Book View

from $184 / night

Book

(20) Very Good 

Certificate of Excellence

38

Villa rental in Kissimmee City with swimming pool

Kissimmee / Kissimmee City

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~¤~ YOUR DREAM VACATION RENTAL IN THE SUNSHINE CAPITAL IS HERE ... COME AND ENJOY: A Beautiful Sun Drenched 4 bedroom 2 storey fully air-conditioned vacation home on premier …see more

Certificate of Excellence

Map

Add to shortlist

from $132 / night

$831 - $1,016 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from $132 / night

Book

“One word to sum up this villa...... PERFECT !!!”

Reviewed 9 Mar 2013

Choosing a villa was quite a hard task to ensure that the whole family enjoyed their vacation in Florida. It needed to be centrally located to all the main parks, be furnished to a good standard & ha… More

It was a pleasure to have you as our guests. We are looking forward to welcoming you back in October. :-)

“Perfect Place For An Orlando Vacation”

Reviewed 12 Oct 2012

If you are looking for a great place to relax, laze by the pool and soak up the sun or if you want a base close to the parks or outlets then Villa Londra is definately the place for you. The villa … More

We are delighted that you have enjoyed your second stay with us. Our aim was to make Orlando Villa Londra as welcoming as possible and to provide a quality home-from-home to make for a happy, carefree and relaxing holiday; your review confirms we seem to be getting it right - Thank You. We look forward to hearing from you again soon. :-)

“very enjoyable villa with fantastic access to Disney”

Reviewed 30 Aug 2012

we stayed in Villa Londra from the 17th-31st July 2012. After a 9 hr flight it was great that the villa was only 20 minutes from the airport and also only 20 minutes from the Disney parks. The Villa i… More

It was a pleasure to have you as our guests, we would, of course, be delighted to hear from you again in the future :-)

See all reviews

(6) Excellent 

75

Vacation villa rental

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This large executive luxury detached roomy largely open plan airy villa is very well equipped, lavishly and comfortably furnished and decorated to a high standard. Recently built to our own design, this 4 bedroom, 3 bathroom luxury villa with private heated and screen …see more

Map

Add to shortlist

from $140 / night

$935 - $985 / week

Book View

Responds fast!
avg. 2 hours 33 minutes

from $140 / night

Book

“Luxurious, spaceous secluded villa”

Reviewed 8 Nov 2013

Excellent location to all amenities. Villa exceptionally equipped with luxurious facilities. Didn't want to leave !!… More

“Huge villa in a quiet residential area and close to Disney”

Reviewed 31 Aug 2015

This villa is huge and finished to an excellent standard. It is well appointed, very spacious with a great pool and Jacuzzi. Plenty of room to unwind after a hard day at a Park. The villa is sited in … More

See all reviews

(2) Good 

55

Vacation townhouse in Kissimmee

Kissimmee / Kissimmee City

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This Terra Verde townhome has a patio and Hot Tub which overlooks the resort's lake. It has just been totally revamped. The interior has been painted in a subtle modern color .This is complemented by new tile downstairs and in the homes bathrooms. All three bedrooms boa …see more

Map

Add to shortlist

from $107 / night

$746 - $875 / week

Book View

Responds fast!
avg. 49 minutes

from $107 / night

Book

“Great wee resort”

Reviewed 27 Jul 2016

Terra Verde was an immaculately kept resort. Seemed to be 20mins from most big attraction parks. This house was ideal for our family of four and could easily have accommodated 2 more. It was spotlessl… More

See all reviews

(1) Excellent 

41

Vacation home in Kissimmee City

Kissimmee / Kissimmee City

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Well-appointed House in gated community with security there is 5 miles from the Disney complex. Condominium with swimming pool, jacuzzi, games room, gisnastica room, tennis court, basketball and volleyball, cinema and convenience store. House with 4 bedrooms and 2 bathr …see more

Map

Add to shortlist

from $120 / night

$840 / week

Book View

Responds fast!
avg. 2 hours 47 minutes

from $120 / night

Book

(4) Very Good 

21

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

8 20 Min stay varies

  • 8 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This Executive vacation home near Disney located in Emerald Island Resort is tastefully decorated throughout to make you feel at home. Accent painting, colorful curtains and nice furnishings. The villa is located a short walk from the club house and is on a private cons …see more

Map

Add to shortlist

from $219 / night

$1,299 - $2,899 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from $219 / night

Book

(4) Very Good 

37

Villa accommodation in Kissimmee City

Kissimmee / Kissimmee City

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 119 mi
  • Swimming pool
Spacious 2,300 Sqft, high ceilings, large 4 bed 2.5 bath villa with extended private deck and large pool with spa. This lovely two-story home located in the Linfield Community of Kissimmee, just off of Highway 192 and only minutes to the gates of Disneyworld. Enter t …see more

Map

Add to shortlist

from $113 / night

$791 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from $113 / night

Book

(1) Excellent 

26

Vacation townhouse with swimming pool in Kissimmee

Kissimmee / Kissimmee City

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our Villa in Terra Verde Resort! Just perfect for families who want to be close to the Orlando Theme parks but don't want to spend big $$$ on accommodation! This wonderful pool home is located in the highly popular gated resort community of Terr …see more

Map

Add to shortlist

from $139 / night

$973 - $1,113 / week

Book View

Responds fast!
avg. 1 hour 10 minutes

from $139 / night

Book

(4) Excellent 

49

Vacation home with indoor pool in Kissimmee City

Kissimmee / Kissimmee City

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Property Type: 5 Bedrooms, 5 Baths House with Private Pool and Game Room. Floor Area: 3000 sq. ft.Location:Paradise Palms Resort, Disney Area This beautiful unit is located in Paradise Palms Resort one of Florida's Premier Resorts only 5 minutes from Disney!! and withi …see more

Map

Add to shortlist

from $350 / night

$2,450 / week

Book View

from $350 / night

Book
24

Vacation townhouse with golf nearby in Kissimmee City

Kissimmee / Kissimmee City

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
Recently renovated!! Freshly painted, new TV sets, new celling fans and new carpet installed. Oakwater community also received lots of improvements and is one of the top-rated communities on Trip Advisor website! Our home is located just minutes from the gates of Walt D …see more

Map

Add to shortlist

from $99 / night

$630 / week

Book View

from $99 / night

Book
20

Vacation townhouse in Kissimmee City

Kissimmee / Kissimmee City

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
This townhome with 3 bedrooms and 2/5 bathrooms, is located in the attractive gated community, Compass Bay, only few min. from Disney. Nearby are also restaurants, shopping outlets, golf courses and a Walmart-store. The house is elegantly furnished, with all the kitchen …see more

Map

Add to shortlist

from $90 / night

$630 / week

Book View

from $90 / night

Book

(8) Excellent 

39

Vacation villa rental

Kissimmee / Kissimmee City

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Luxurious and Beautiful Villa is ideally located at exclusive Season Community , about 6 miles short distance from Disney World & about minutes distance from the best restaurants and shops of the Central FL. Close to 24 hrs Wal Mart . Lake Buena Vista Factory Stores, 5 …see more

Map

Add to shortlist

from $199 / night

$1,393 / week

Book View

from $199 / night

Book

(1)  

14

Kissimmee Vacation condo rental

Kissimmee / Kissimmee City

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Vacation Village at Parkway - Orlando, FL: 1-BR, Sleeps 4, with Kitchenette, Fixed week rental - 7 nights segments only. Check-in days: Fri, Sat, Sun. Unit Features: 625 sq.feet Full Kitchen no rangeIndividual living and dining rooms in all suites Ceramic tile and ca …see more

Map

Add to shortlist

from $111 / night

$775 - $875 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

from $111 / night

Book
22

Kissimmee Vacation apartment rental

Kissimmee / Kissimmee City

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
This Dream villa is equipped with everything a family could need for a magical Florida vacation, while still enjoying all the comforts of home, including a washing machine, clothes dryer. A dining-room table and ample living room give families and groups plenty of space …see more

Map

Add to shortlist

from $79 / night

$553 / week

Book View

from $79 / night

Book
8

Vacation villa in Kissimmee

Kissimmee / Kissimmee City

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a timeshare. Villa is fully equipped and has a Jacuzzi and a shower, full kitchen, washer and dryer, etc. You can see other amenities available in villa and/or on site some for an additional fees. You are required to have a credit card when checking in for in …see more

Map

Add to shortlist

from $100 / night

$700 / week

Book View

Responds fast!
avg. 2 hours 27 minutes

from $100 / night

Book