Walking holiday villas and apartments Kissimmee

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  • United States
  • Florida
  • Central Florida
  • Kissimmee
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  • Bellavida Resort (2)
  • Cane Island (1)
  • Compass Bay (3)
  • Coral Cay (2)
  • Creekside (1)
  • Crystal Cove Resort (1)
  • Cumbrian Lakes (3)
  • Doral Woods (3)
  • Emerald Isle Kissimmee (12)
  • Encantada Resort (1)
  • Fiesta Key (3)
  • Formosa Gardens (1)
  • Indian Creek (2)
  • Indian Ridge (1)
  • Kissimmee City (3)
  • Lake Berkley (5)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (1)
  • Lindfields (1)
  • Oak Island Cove (2)
  • Oak Island Harbor (1)
  • Orange Lake Resort (3)
  • Paradise Palms (5)
  • Regal Oaks (2)
  • Remington (2)
  • Seasons Resort (1)
  • Sunset Lakes (2)
  • Terra Verde Resort (1)
  • The Hamlets (1)
  • Trafalgar Village (3)
  • Venetian Bay Villages (2)
  • Veranda Palms (1)
  • Villasol (2)
  • Westside (3)
  • Windsor Hills Resort (2)
  • Windsor Palms (1)
  • Winward Cay (2)

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Also consider

Emerald Isle Kissimmee
58 properties
Kissimmee City
34 properties
Villas Paradise Palms
32 properties
Villas Windsor Hills Resort
32 properties
Lake Berkley
27 properties
Villas Windsor Palms
21 properties
Cumbrian Lakes
20 properties
Lindfields
20 properties
Bellavida Resort
20 properties
Terra Verde Resort
18 properties
Villas Indian Creek
14 properties
Crescent Lakes
13 properties
Sunset Lakes
11 properties
Compass Bay
11 properties
Venetian Bay Villages
11 properties
Regal Oaks
10 properties
Eagle Pointe
10 properties
Villas Formosa Gardens
9 properties
Doral Woods
9 properties
Veranda Palms
8 properties
Payment Protection
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166 Holiday homes

Filters applied: Walking holidays (166)

Travellers going to Kissimmee are booking December dates now. Secure your holiday home today and have the perfect trip.

28

Marcellas Luxury Private Gated Villa - Kissimmee villa sleeps 12

Central Florida / Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 10 km
  • Swimming pool
  • Child friendly
Our villa is one of only 32 pure luxury villas, located in this private gated community. No villas are overlooked so you have guaranteed total privacy and you get the sun at the pool from morning until about 4pm daily! We have a large pool with separate jacuzzi. Inside  …see more

from £131 / night

£916 - £1077 / week

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from £131 / night

(2) Very Good 

75

Villa View - Cumbrian Lakes villa sleeps 10

Kissimmee / Cumbrian Lakes

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
This home has everything you need for a great family stay. The crystal clear pool overlooks a lake and there is a spa for the adults to enjoy. The children also have a tiled Games Room where they can shoot a game of pool, challenge a friend to a foosball competition or  …see more

from £95 / night

£665 - £805 / week

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from £95 / night

47

Kissimmee / Paradise Palms

4 10 4 nights min

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

 …see more

from £100 / night

£693 - £1616 / week

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from £100 / night

(2) Very Good 

59

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £81 / night

£566 / week

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from £81 / night

41

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £154 / night

£1308 - £1500 / week

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from £154 / night

46

Mickeys Retreat Villa Windward Cay Near Disney - Kissimmee villa sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Turn your dreams into reality in our Luxury Holiday Villa just a short distance from the Orlando theme parks.This is Mickey's Retreat, our 3 Bedroom, 2 Bathroom Villa in Kissimmee, Florida. Mickey's Retreat is conveniently situated just a short ten minute driv  …see more

from £89 / night

£527 - £793 / week

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from £89 / night

(42) Excellent 

21

EXECUTIVE VILLA SET IN ONE ACRE FENCED AND PRIVATE - Doral Woods villa sleeps 8

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is set in one acre of private fenced garden with a children's play area and 20 x 30 wood BBQ decking and 28 x 14 private heated pool with spa. Relax on the private sundeck we have plenty of comfy chairs . There is seating for 8 for dining around the pool an  …see more

from £130 / night

£895 - £995 / week

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from £130 / night

22

Executive Lack Backing Disney Villa - Lake Berkley - Lake Berkley villa sleeps 11

Kissimmee / Lake Berkley

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
It pays to book quality, read our reviews, we are not the cheapest nor the most expensive but we like to think we are one of the best Just Imagine lying in your kingsize master bed looking out through your own patio windows with direct access to your own sparkling priv  …see more

from £85 / night

£595 / week

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from £85 / night

22

Disney Vacation Rental - Venetian Bay Villages townhouse sleeps 10

Kissimmee / Venetian Bay Villages

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 97 km
  • Swimming pool
  • Child friendly
You will definitely enjoy your stay in our 4 bedroom townhouse in Venetian Bay Villages, Kissimmee, FL. Our townhouse sleeps up to 10 comfortably, with 4 bedrooms, a full kitchen, 3.5 bathrooms, a spacious living area with large flat screen cable TV and dining area. Y  …see more

from £80 / night

£560 - £700 / week

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from £80 / night

(2) Very Good 

20

Villa Sol 5 bedroom luxury villa . - Villasol villa sleeps 12

Kissimmee / Villasol

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
A beautifully appointed 5 bedroom, 3 bath luxury family vacation home provides state of the art living, comfort and freedom that cannot be found in a hotel room. The master bedroom has a king size bed, walk in wardrobe, and en-suite with walk in shower, the 2nd and 3rd  …see more

from £100 / night

£600 - £880 / week

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from £100 / night

(1) Very Good 

20

Kissimmee Lake Front Villa - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 105 km
  • Swimming pool
Get your vacation started 15 minutes after leaving the airport when you stay in your private Regal Villa, an oasis of relaxation and fun. It's only 20 minutes straight down Osceola Parkway to Disney's gate, the same area as Universal Studios and Sea World. Jus  …see more

from £108 / night

£754 / week

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from £108 / night

(3) Excellent 

42

Executive 2 Story Villa in Kissimmee Gated Community - Cumbrian Lakes villa sleeps 11

Kissimmee / Cumbrian Lakes

5 11 4 nights min

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
HUGE ! five star accredited villa near Disney , If you require something a little bit special for that once in a lifetime Florida vacation our home is the one for you !! Enquire early for further details about the standard of accommodation and five star facilities  …see more

from £140 / night

£980 / week

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from £140 / night

(1) Excellent 

5

Orange Lake Country Club - Orange Lake Resort villa sleeps 8

Kissimmee / Orange Lake Resort

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa located at Orange Lake Country Club - Golf Resort, in west Kissimmee, Florida.Is is a beautiful family resort, with a river island, golf courses, daily water and earth activities. You will have an unforgivable experience.The villa has all the comforts and you will  …see more

from £132 / night

£924 / week

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from £132 / night

17

Villa Aqua Orlando - Kissimmee villa sleeps 12

Central Florida / Kissimmee

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Enjoy your family vacation at our family owned, luxury 5-bed 5-bath Villa Aqua with private pool and spa at the Windsor Hills resort near to Walt Disney World in Orlando, Florida. Relax in the comfort of our luxury villa with five bedrooms, a games room and all the conv  …see more

from £143 / night

£997 / week

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from £143 / night

15

Fiesta Key Resorts At The Park - Fiesta Key townhouse sleeps 8

Kissimmee / Fiesta Key

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 123 km
  • Swimming pool
Fiesta Keys Resort The townhome, situated in the exclusive Fiesta Key Resort in Kissimmee - ideally situated within easy reach of all the major Orlando theme parks, attractions, shops and restaurants. The house has TWO master bedroom suites - one downstairs and one  …see more

from £97 / night

£616 / week

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from £97 / night

55

The Great Escape - Lake Berkley villa sleeps 9

Kissimmee / Lake Berkley

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Lake Berkley is known as one of the most sought after locations for a great vacation in Kissimmee Orlando. The resort is a gated community and offers 24/7 manned security at the main gate. We have 3 fishing lakes, outside fitness equipment, volley ball, kiddies playgro  …see more

from £90 / night

£550 - £785 / week

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from £90 / night

(2) Very Good 

18

Florida-Villa-Natalie - Kissimmee villa sleeps 9

Central Florida / Kissimmee

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
Our luxury Holiday home comes with many Upgrades to make your stay a special one! The villa is large and spacious so ideal for 2 families to share.Lounge is Recently Remodeled and tastefully decorated with three 2 seater sofa's Large 50'' HD TV/DVD Player  …see more

from £93 / night

£650 - £750 / week

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from £93 / night

20

Fountain View - Cumbrian Lakes villa sleeps 10

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
This 5 bed villa is situated in the quiet gated community of Cumbrian Lakes just 10 minutes from the Disney attractions. It has a large pool with spa and deck toilet. Plenty of deck furniture allows everyone to relax and enjoy the Florida sunshine. There is also a great  …see more

from £90 / night

£630 - £940 / week

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from £90 / night

15

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ski
  • Child friendly

 …see more

from £112 / night

£781 / week

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from £112 / night

(2) Excellent 

27

Disney Magic Villa by Emerald Island Rentals - Emerald Isle Kissimmee villa sleeps 16

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
A 7 bed/4.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa.With 2 king master suites, 2 queen bedrooms, 2 themed kids rooms with two twins each and another room with 2 bunk beds, this v  …see more

from £174 / night

£1500 - £2154 / week

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from £174 / night

(10) Excellent 

20

Villa di Lusso - Bellavida Resort villa sleeps 14

Kissimmee / Bellavida Resort

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa di Lusso is located 20 minutes away from all of the main attractions and theme parks that Orlando has to offer. Our luxury 6 bedroom villa has en suite bathrooms to each bedroom, with two living areas one formal and one casual. this villa is ideal for families who  …see more

from £160 / night

£1087 / week

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from £160 / night

(8) Excellent 

19

4345 Creekside Blvd - Creekside villa sleeps 8

Kissimmee / Creekside

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 110 km
  • Swimming pool
Share your breakfast with the eagles and alligators. Spend the day at the park or shopping and return to a solar heated pool (conventional heating also available). Relax and watch the Floridian sun rise behind the trees! This three bedroom, two bath home is decorated an  …see more

from £70 / night

£490 / week

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from £70 / night

50

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £74 / night

£512 / week

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from £74 / night

48

Amazing Upscale Home Loaded with Upgrades - Indian Creek house sleeps 12

Kissimmee / Indian Creek

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Imagine coming home at the end of an exhilarating day at the parks... You grab a refreshing drink from the fridge, flake out on the sofa by the pool and reminisce about all the amazing things you did that day. Memories made,  …see more

from £312 / night

£2074 - £2916 / week

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from £312 / night

(2) Excellent 

32

Kissimmee / Terra Verde Resort

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £132 / night

£922 - £1837 / week

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from £132 / night

(2) Very Good 

13

West Village at Orange Lake - Orange Lake Resort villa sleeps 8

Kissimmee / Orange Lake Resort

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This family-friendly resort, spanning more than 1,400 acres, is right on the doorstep of Walt Disney World and offers a wide variety of activities on both water and land. Villas, apartments and suites are available.Holiday Inn Club Vacations at Orange Lake Resort featur  …see more

from £171 / night

£1200 / week

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from £171 / night

17

Windsor Hills Perfect Hideaway - Kissimmee villa sleeps 13

Central Florida / Kissimmee

6 13 5 nights min

  • 6 bedrooms
  • Sleeps 13
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Child friendly
3 Master Suites : Queen Suite On Ground Floor : Lake View : Large Private Pool & Spa : Free High Speed Wifi : Free International Calls: Luxury Games RoomsWelcome to our outstanding Windsor Hills Perfect Hideaway Villa where the magic starts minutes from Disney World  …see more

from £175 / night

£1225 / week

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from £175 / night

26

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Nearest beach 116 km
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£462 / week

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from £77 / night

(5) Excellent 

23

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £49 / night

£338 - £350 / week

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from £49 / night

7

Central Florida / Kissimmee

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

 …see more

from £165 / night

£1154 - £1539 / week

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from £165 / night

(26) Excellent 

40

Kissimmee / Compass Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 81 km
  • Swimming pool

 …see more

from £69 / night

£461 - £615 / week

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from £69 / night

30

Kissimmee / Lake Marion

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 126 km
  • Swimming pool

 …see more

from £43 / night

£297 / week

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from £43 / night

(1) Excellent 

15

Kissimmee / Coral Cay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 81 km
  • Swimming pool
  • Child friendly

 …see more

from £74 / night

£493 - £858 / week

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from £74 / night

49

Central Florida / Kissimmee

3 6 3 nights min

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

 …see more

from £77 / night

£570 / week

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from £77 / night

(2) Excellent 

16

Kissimmee / Paradise Palms

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £115 / night

£803 / week

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from £115 / night

11

Central Florida / Kissimmee

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £116 / night

£808 / week

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from £116 / night

(1) Excellent 

42

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

 …see more

from £59 / night

£408 - £512 / week

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from £59 / night

(13) Excellent 

19

Central Florida / Kissimmee

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £58 / night

£385 / week

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from £58 / night

24

Kissimmee / Kissimmee City

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 119 km
  • Swimming pool

 …see more

from £98 / night

£684 - £894 / week

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from £98 / night

30

Central Florida / Kissimmee

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £77 / night

£520 / week

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from £77 / night

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