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

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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

from $77 / night

$449 - $904 / week

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avg. 3 hours 9 minutes

from $77 / night

(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

from $168 / night

$1174 / week

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from $168 / night

(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

from $98 / night

$683 - $819 / week

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avg. 3 hours 42 minutes

from $98 / night

(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

from $89 / night

$595 - $776 / week

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avg. 3 hours 58 minutes

from $89 / night

(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

from $135 / night

$895 - $1025 / week

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avg. 1 hour 22 minutes

from $135 / night

(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

from $143 / night

$714 - $2067 / week

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avg. 2 hours 2 minutes

from $143 / night

(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

from $104 / night

$715 / week

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from $104 / night

(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

from $132 / night

$895 - $1150 / week

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from $132 / night

(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

from $120 / night

$840 / week

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avg. 2 hours 4 minutes

from $120 / night

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

from $90 / night

$625 / week

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from $90 / night

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

from $138 / night

$1190 - $1645 / week

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from $138 / night

(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

from $199 / night

$1393 / week

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from $199 / night

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

from $99 / night

$630 / week

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from $99 / night

(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

from $96 / night

$1155 / week

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Responds fast!
avg. 2 hours 16 minutes

from $96 / night

(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

from $189 / night

$1323 / week

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from $189 / night

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

from $88 / night

$616 / week

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Responds fast!
avg. 2 hours 5 minutes

from $88 / night

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

from $219 / night

$1199 - $2699 / week

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Responds fast!
avg. 32 minutes

from $219 / night

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

from $70 / night

$553 / week

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Responds fast!
avg. 3 hours 23 minutes

from $70 / night

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

from $120 / night

$840 / week

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Responds fast!
avg. 1 hour 51 minutes

from $120 / night

(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

from $97 / night

$675 - $875 / week

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Responds fast!
avg. 2 hours 11 minutes

from $97 / night

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

from $80 / night

$560 / week

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Responds fast!
avg. 3 hours 23 minutes

from $80 / night

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

from $100 / night

$700 / week

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Responds fast!
avg. 44 minutes

from $100 / night

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

from $80 / night

$560 / week

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Responds fast!
avg. 3 hours 6 minutes

from $80 / night