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

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Kissimmee City

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23 Vacation rentals

(22) 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

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from $77 / night

$449 - $904 / week

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avg. 3 hours 9 minutes

from $77 / night

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“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

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(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

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from $168 / night

$1174 / week

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from $168 / night

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(1) Very Good 

56

Vacation townhouse in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

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from $98 / night

$683 - $819 / week

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avg. 3 hours 42 minutes

from $98 / night

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“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

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(1) Very Good 

20

Condo rental in Kissimmee City with golf nearby

Kissimmee / Kissimmee City

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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

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from $89 / night

$595 - $776 / week

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avg. 3 hours 58 minutes

from $89 / night

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(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

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from $135 / night

$895 - $1025 / week

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avg. 1 hour 22 minutes

from $135 / night

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“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

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(8) Excellent 

24

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

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from $143 / night

$714 - $2067 / week

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avg. 2 hours 2 minutes

from $143 / night

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(2) Excellent 

66

Vacation villa with shared pool in Kissimmee

Kissimmee / Kissimmee City

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Lakes is a semi-residential gated community situated off the 192 Irlo Bronson Highway approximately 2 miles west of Interstate 4. World Drive, which is the entrance to all the Disney theme parks is less than 10 minutes drive away. Universal Studios, Sea Worl …see more

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from $104 / night

$715 / week

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from $104 / night

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“Perfect in every way”

Reviewed 1 Sep 2013

we have stayed here several times (approx. 10) and every time the house delivers what we expect in a Florida villa. Villa is cleaned to a high standard on arrival, the kitchen has everything you have … More

“Best Vacation House Ever”

Reviewed 12 Aug 2013

Our vacation stay at Sunsetlakes Villa in Orlando Florida Was very nice the 3 bedroom was spacious and nice clean the the living room was also spacious.We had everything we needed on our vacation al… More

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(18) Excellent 

Certificate of Excellence

36

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

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from $132 / night

$895 - $1150 / week

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from $132 / night

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“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 :-)

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(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

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from $120 / night

$840 / week

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avg. 2 hours 4 minutes

from $120 / night

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25

Kissimmee City Vacation home rental

Kissimmee / Kissimmee City

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 93 mi
  • Swimming pool
3 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps maximum of 8 The Encantada Resort is a private luxury gated community just 3 miles from Disney World. This Mediterranean-style resort is only a short drive to all other Orlando attractions and just blocks away from …see more

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from $90 / night

$625 / week

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from $90 / night

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35

Kissimmee City Vacation townhouse rental

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Casa 4 dorms no condomínio resort "Paradise Palms". Excelente casa de ferias com 4 dormitórios sala de estar e jantar 3 banheiros, cozinha, sala de jantar, piscina privativa, roupas de camas e banho. Em um belíssimo condomínio em kissimmee, com segurança 24 horas, cond …see more

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from $138 / night

$1190 - $1645 / week

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from $138 / night

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(4) Excellent 

49

Vacation home with indoor pool in Kissimmee City

Kissimmee / Kissimmee City

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

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from $199 / night

$1393 / week

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from $199 / night

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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

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from $99 / night

$630 / week

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from $99 / night

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(1) Very Good 

24

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, high ceilings, large 4 bed 2.5 bath villa with extended private deck and large pool with spa. Pool/Spa heat are already calculated within the nightly rates from October through May. This lovely two-story home located in the Linfield Community of Kissimmee, jus …see more

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from $96 / night

$1155 / week

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avg. 2 hours 16 minutes

from $96 / night

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(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

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from $189 / night

$1323 / week

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from $189 / night

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26

Vacation townhouse with swimming pool in Kissimmee

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

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from $88 / night

$616 / week

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avg. 2 hours 5 minutes

from $88 / night

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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

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from $219 / night

$1199 - $2699 / week

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avg. 32 minutes

from $219 / night

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22

Kissimmee Vacation apartment rental

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

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from $70 / night

$553 / week

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avg. 3 hours 23 minutes

from $70 / night

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42

Kissimmee City Vacation home accommodation

Kissimmee / Kissimmee City

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful 4 bedroom home is new, has 2 suites and a private pool. It is ideally located close to US192 with many shops and restaurants, 10 minutes away from Disney and only 20 minutes from Sea World and Universal Studios. It is also conveniently located near SuperT …see more

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from $120 / night

$840 / week

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avg. 1 hour 51 minutes

from $120 / night

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(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

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from $97 / night

$675 - $875 / week

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avg. 2 hours 11 minutes

from $97 / night

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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

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from $80 / night

$560 / week

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avg. 3 hours 23 minutes

from $80 / night

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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

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from $100 / night

$700 / week

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avg. 44 minutes

from $100 / night

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22

Vacation condo in Kissimmee

Kissimmee / Kissimmee City

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 81 mi
  • Swimming pool
  • Child friendly
Condo in Orlando, Kissimmee, FL. Villas of Somerset. Close to Disney World. 3 bedrooms, 2 baths. Pool, hot tub, parking on the premises. Dishes, pots n pans, stove, dishwasher, fridge, flat screen TV, cable, washer/dryer. WiFi Available for additional charge. Local cal …see more

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from $80 / night

$560 / week

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Responds fast!
avg. 3 hours 6 minutes

from $80 / night

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