50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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Emerald Isle Kissimmee
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Windsor Hills Resort
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Cumbrian Lakes
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Lindfields
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Terra Verde Resort
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Bellavida Resort
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Compass Bay
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Crescent Lakes
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Doral Woods
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Seasons Resort
8 properties
Orange Lake Resort
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Formosa Gardens
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Coral Cay
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Encantada Resort
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Sunset Lakes
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Kissimmee

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5,199 Vacation rentals

(27) Excellent 

23

Vacation villa rental

Kissimmee / Veranda Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 84 mi
  • Swimming pool
  • Child friendly
Stunning four bedroom holiday home with private pool ideally located on Veranda Palms Resort. 4 bedroom, 3 bathroom villa is situated on the impressive Veranda Palms Resort in Orlando. The resort is set in a sprawling conservation area with beautiful lakes and woodla …see more

from $135 / night

$945 - $1085 / week

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avg. 1 hour 12 minutes

from $135 / night

(32) Very Good 

23

Vacation condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 106 mi
  • Swimming pool
  • Child friendly
A perfect location for all that central Florida has to offer, for Mickey fans, serious shoppers, sun worshippers, delicious dining, space shuttle launches, big thrills and spills, airboat adventures, palm trees and pina-coladas! All in the fantastic Sunshine State! Win …see more

from $46 / night

$283 - $484 / week

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Responds fast!
avg. 2 hours 24 minutes

from $46 / night

(11) Excellent 

28

Vacation villa in Kissimmee

Kissimmee / Windsor Hills Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous 5 Bed/5 Bath Executive Villa with Games Room can easily accommodate 10 guests in absolute comfort. Fully air conditioned and with the added luxury of ceiling fans in all rooms the property offers total privacy and space to relax and enjoy your holiday of a …see more

from $168 / night

$1174 - $1548 / week

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from $168 / night

Featured properties

23

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

5 13 Min stay varies

  • 5 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This new executive villa features state of-the-art living ... 5 bedrooms, 3.5 bathrooms, swimming pool and spa. Cumbrian Lakes is set in a conservation area yet only 5 minutes from shops and restaurants and less than 15 minutes to Disney World. The execut …see more

from $136 / night

$1012 - $1283 / week

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from $136 / night

(9) Excellent 

37

Vacation home rental

Central Florida / Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Ocean Bluff backing on to a natural pond is the perfect location set in a stunning conservation area on the shores of 3,800 acre Lake Marion yet only 35 minutes drive away from Disney, Orlando and all its attractions and close to several championship golf courses. Enjo …see more

from $84 / night

$581 - $798 / week

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Responds fast!
avg. 3 hours 15 minutes

from $84 / night

(4) Excellent 

28

Vacation villa in Seasons Resort

Kissimmee / Seasons Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This Kissimmee home offers plenty for all the family – from the jungle-themed kids' TV and entertainment space to the wonderful, sparkling pool overlooking the attractive lake. Plus, it has a good location for access to all of Orlando's amusement parks & attractions. It …see more

from $195 / night

$1295 - $2095 / week

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from $195 / night

(4) Excellent 

24

Vacation villa in Kissimmee

Kissimmee / Tuscany, Florida

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This Italian style one storey villa completed in 2008 has 3 bedrooms a family bathroom and shower room. It is located on the sought after Tuscany development and is perfect for a family holiday to Orlando where you can enjoy the wonderful climate and year round sunshin …see more

from $70 / night

$491 - $633 / week

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from $70 / night

(16) Excellent 

24

Kissimmee Vacation villa rental

Kissimmee / Veranda Palms

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 75 mi
  • Swimming pool
The property is a spacious 4 bedroom, 3 bathroom villa with a private, 30ft pool. It is ideally located close to the US192 with its many shops and restaurants and only 10 mins from Walt Disney World whilst Sea World and Universal Studios are within 25 mins. Florida's fa …see more

from $117 / night

$749 - $1000 / week

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from $117 / night

(6) Excellent 

31

Vacation villa in Kissimmee

Kissimmee / Seasons Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This villa is furnished to a high standard throughout. The bright & spacious rooms provide plenty of room for the whole family. The highlight has to be the lovely south-west-facing pool – the perfect spot to unwind at the end of a long day enjoying Orlando's many at …see more

from $200 / night

$1350 - $2195 / week

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from $200 / night

(61) Excellent 

60

Villa rental in Kissimmee

Kissimmee / Indian Ridge

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury executive home located at the head of a quiet cul-de-sac on Indian Ridge, 10 mins from the Disney Main Gate. The spacious, air-conditioned accommodation (2000sqft) comprises 4 bedrooms (2 doubles, 2 twin "character" rooms), 2 bathrooms (1 en-suite), 2 lounges (o …see more

from $117 / night

$613 - $936 / week

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from $117 / night

(2) Excellent 

15

Kissimmee Vacation villa accommodation

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
Just as the name suggests, Emerald Island Resort is truly a tropical oasis. Nestled within a protected wetland, a unique vacation destination. Emerald Island is located minutes from Walt Disney World and the myriad other resorts and activities that bring millions to Or …see more

from $185 / night

$1295 / week

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Responds fast!
avg. 2 hours 41 minutes

from $185 / night

(23) Very Good 

18

Kissimmee Vacation villa rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is furnished to the highest standard and has the WOW factor. The villa has recently been tiled from the Great Room to the Living Room and new carpets in all the bedrooms. From the large hallway it opens up to the large Great room with wall to wall mirrors g …see more

from $84 / night

$581 - $645 / week

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from $84 / night

(11) Very Good 

25

Vacation villa in Kissimmee

Kissimmee / Crescent Lakes

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This vacation home is set in the tranquil and beautiful conservation area of Crescent Lakes. Guests will find a peaceful retreat from the busy theme parks & shopping malls. This spacious home has a fabulous South-facing private pool & children's splash pool. The pool …see more

from $110 / night

$650 - $795 / week

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from $110 / night

(31) Very Good 

18

Kissimmee Vacation townhouse rental

Kissimmee / Venetian Bay Villages

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 55 mi
  • Swimming pool
Enjoy the comforts of our 3 bedroom, 2 bathroom town home which will sleep 6. The home was newly built in Jan 2004 and is located on a gated community in Kissimmee (just off the US192) 15 mins from Disney. Wi-Fi internet access provided in the home. On site f …see more

from $60 / night

$416 - $533 / week

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from $60 / night

(24) Excellent 

22

Vacation 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
The villa benefits from its own private pool, with a shallow end perfect for the children. Leading from the living room is a spacious patio with stunning conservation views, furnished with a table and chairs to enable you to dine al fresco. The villa is …see more

from $136 / night

$820 - $1065 / week

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Responds fast!
avg. 3 hours 25 minutes

from $136 / night

(19) Very Good 

27

Vacation villa in Kissimmee

Kissimmee / Formosa Gardens

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Set in a third of an acre with extensively landscaped gardens and mature palm trees, this spacious (4.000 sq. ft.) luxury home has been professionally furnished and decorated to the highest of standards and enjoys many upgraded facilities including tiling throughout the …see more

from $185 / night

$1290 - $1677 / week

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from $185 / night

(4) Excellent 

12

Vacation home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Living Room 2 and 3 seat sofa's with coffee table ,40" flat screen TV with DVD / BLURAY player. Ceiling fan. Dining Area Table and 4 chairs, 2 Stools Kitchen Fully equipped with all the utensils you will ever need. Utility Room Full laundry facilities are provided. …see more

from $78 / night

$542 / week

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Responds fast!
avg. 3 hours 57 minutes

from $78 / night

(30) Excellent 

24

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Welcome to our 4 bed single storey air conditioned home in Rolling Hills, Kissimee. It is just 10 mins (real time) to Disney Main Gate. It is situated on a part residential, part visitors estate, with lake views at the rear, in a quiet neighbourhood, close to Fo …see more

from $117 / night

$839 - $1058 / week

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Responds fast!
avg. 3 hours 50 minutes

from $117 / night

(20) Excellent 

28

Villa rental in Kissimmee

Kissimmee / Doral Woods

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
********** AMAZING CASTLE IN THE SUN ************* IDYLLIC PLACE TO RELAX AFTER ALL THE FUN OF THE DISNEY MAGIC *** LUXURY VILLA WITH A COMPLETELY PRIVATE SOUTH FACING POOL * 3 Beds, 2 Baths, 2 Lounges.* CABLE TV's, VCR/DVD* GAMES consoles in bedrooms* GAMES ROOM* FULLY …see more

from $88 / night

$607 - $729 / week

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Responds fast!
avg. 37 minutes

from $88 / night

(21) Very Good 

68

Vacation villa in Kissimmee

Kissimmee / Lindfields

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxurious Detached Villa- 5 Bedrooms - 3 Baths - (Sleeps 12) Simply the best location! Just a ten-minute drive from the Disney Theme parks but set in the quiet haven of the prestigious Lindfields Estate. This luxury villa sleeps up to 12 people and is beautifully …see more

from $129 / night

$581 - $697 / week

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Responds fast!
avg. 2 hours 27 minutes

from $129 / night

(14) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Windsor Palms

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Windsor Palms is a fabulous resort style community and has all the facilities that you would expect from its 5 star status all completely free when you stay at Disney Paradise. It is one of the closest communities to Disney located along Formosa Gardens Boulevard just …see more

from $129 / night

$839 - $903 / week

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Responds fast!
avg. 3 hours 27 minutes

from $129 / night

(24) Excellent 

18

Vacation villa with swimming pool in Kissimmee

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A beautiful lakeside American Villa with a private pool with wonderful views of the lake, wildlife and woodland area. No back-to-back villas here!. Thousands of £'s spent recently on upgrading the villa with new facilities. The Villa is Located just off Poinciana …see more

from $88 / night

$613 / week

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from $88 / night

(2) Excellent 

70

Vacation villa rental

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 114 mi
  • Swimming pool
Scotsman's Retreat is a beautiful and quiet 2 storey 5 bedroom house house on Cumbrian Lakes which is a relatively new gated community build in a conservation area and, as the names suggests, based around 3 large lakes. The villa is situated in an ideal location with …see more

from $123 / night

$858 - $1129 / week

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from $123 / night

(13) Excellent 

24

Calabria, Orlando Vacation villa rental

Kissimmee / Calabria, Orlando

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
My Disney Villa a new villa within the exclusive Calabria community. The 5 bedrooms and 4.5 bathrooms have been finished to a very high standard and the villa offers all the amenities for your perfect holiday. The house overlooks conservation land, an enviable location …see more

from $170 / night

$1190 / week

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Responds fast!
avg. 2 hours 41 minutes

from $170 / night

(4) Excellent 

51

Kissimmee Vacation apartment rental

Central Florida / Kissimmee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a newly renovated 1500 SF unit with an open floor plan. Well appointed modern furnishings with ceramic and porcelain flooring throughout. This is ideal for allergy sufferers. The three bedrooms contain 1 King, 1 Queen and 2 twin beds, respectively. There are two …see more

from $85 / night

$595 - $700 / week

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from $85 / night

(24) Very Good 

26

Vacation villa in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury 3 bed 2 bath villa can sleep 8. Large 30ft fully heated secluded pool. Only 15 minutes from airport & theme parks & 1 hour from Kenedy space centre & cocoa beach. Also 1 hour from Bush Gardens & clearwater beach to the west coast. Surounded by beautiful golf cour …see more

from $84 / night

$581 - $1032 / week

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from $84 / night

(2) Excellent 

20

Villa rental in Cumbrian Lakes with swimming pool

Kissimmee / Cumbrian Lakes

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This beautiful 5 bed home is over 2 levels. The sparkling pool overlooks a lake with conservation beyond and is an idyllic setting for your Kissimmee stay. The bottom level has wooden flooring. Here you can relax on the bold striped sofa and watch the flat screen TV. Th …see more

from $136 / night

$949 - $1355 / week

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Responds fast!
avg. 2 hours 14 minutes

from $136 / night

(5) Good 

34

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Villa Betty Boo is on the prestigious Hampton Lakes Community which has a swimming pool, basketball, volleyball and tennis courts for your free use. Hampton Lakes is beautifully landscaped and is a very secure community. Villa Betty Boo has 4 spacious bedrooms and can s …see more

from $110 / night

$770 - $960 / week

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from $110 / night

(8) Excellent 

21

Trafalgar Village Vacation home rental

Kissimmee / Trafalgar Village

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 50 mi
  • Swimming pool
# Lake view, a beautiful view over one of the many small lakes in the area. # Set on an oversized lot, the villa offers wonderful privacy # Private Heated Pool & Spa with views over the lake. # Free internet and local calls # Our wonderfully spacious 5 bedroom home is s …see more

from $150 / night

$1155 / week

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Responds fast!
avg. 3 hours 53 minutes

from $150 / night

(51) Excellent 

43

Westside Vacation villa rental

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Due to cancellation 1st -10th September available. Weekly rate reduced to £595, a reduction of £225 from previous advertised price. This exclusive luxury property, with beautiful Italian themed fixtures and fittings is set in the highly desirable community of (Tuscany/ …see more

from $129 / night

$768 - $1091 / week

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Responds fast!
avg. 40 minutes

from $129 / night

(4) Excellent 

17

Vacation home with golf nearby in Kissimmee

Kissimmee / Terra Verde Resort

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool
Sunseeker House .Sunseeker house is a luxury air conditioned three bedroom town house set on a fabulous gated resort, and over looks a large fishing lake which is close to all of the Disney attractions.it based on a fabulous gated resort of Terra Verde which is only …see more

from $91 / night

$633 / week

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from $91 / night

(3) Very Good 

28

Vacation villa with shared pool in Kissimmee

Central Florida / Kissimmee

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This fabulous villa gives our guests a real home from home experience. It is furnished for relaxation with comfy furniture, carpeted floors & it's own private pool that can be heated. Overview of Villa • Private Pool with Lanai • Recently Refurbished • Games Room • F …see more

from $115 / night

$775 - $945 / week

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from $115 / night

(1) Very Good 

20

Condo rental in Kissimmee 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 - $775 / week

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Responds fast!
avg. 3 hours 42 minutes

from $89 / night

(3) Very Good 

22

Villa rental in Kissimmee with swimming pool

Kissimmee / Cumbrian Lakes

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
This home has a breath taking view from the pool deck. It overlooks a pretty lake and you may be lucky enough to see deer grazing on the conservation area which lies beyond it. The deck area has been extended so there is also a Hot Tub for you to enjoy. The home itself …see more

from $129 / night

$903 - $1174 / week

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Responds fast!
avg. 2 hours 28 minutes

from $129 / night

(32) Excellent 

17

Kissimmee Vacation villa accommodation

Central Florida / Kissimmee

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated in a quiet, well established residential area (Indian Point) our 5 bedroom villa easily accommodates 2 large families. There are 2 large master bedrooms with ensuites, 3 more bedrooms and a further bathroom. Outside space comprises a large private heated swimm …see more

from $115 / night

$800 - $920 / week

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from $115 / night

(1) Excellent 

22

Kissimmee Vacation villa rental

Kissimmee / Winward Cay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious villa with private pool (Optional heating if required). 3 bedrooms plus queen sofa bed in the lounge means 8 people can sleep comfortably. Covered lanai area for relaxing and dining by the pool. Games room with pool, ping-pong and electronic darts. Situated in …see more

from $70 / night

$484 - $710 / week

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from $70 / night

(12) Very Good 

40

Vacation home in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ready to have your dream Florida vacation? You're gonna need a dream house! This vacation villa has 4 bedrooms, 3 bathrooms, and is totally teeming with luxury! Get ready to dive into the exclusive community of Hamilton's Reserve, which offers extreme privacy and …see more

from $140 / night

$950 / week

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from $140 / night

(28) Very Good 

Certificate of Excellence

36

Vacation villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Indian Point with gorgeous lake and conservation view from pool. Indian Point, Kissimmee is a beautiful residential community situated within a few minutes drive of the Highway 192, convenient for the Wal-Mart superstore, a large selection of restaurants, and close t …see more

Certificate of Excellence

from $97 / night

$645 - $774 / week

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Responds fast!
avg. 2 hours 24 minutes

from $97 / night

(3) Excellent 

24

Vacation villa in Sunset Lakes

Kissimmee / Sunset Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A LUXURY LAKESIDE VILLA on the EXCLUSIVE GATED SUNSET LAKES COMMUNITY. Sunset Lakes is a small, quiet, exclusive, gated community with luxury homes situated around two private lakes. Directly off Highway 192 and only minutes from Disney and all other attractions. Our …see more

from $109 / night

$678 - $897 / week

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from $109 / night

(11) Very Good 

50

Vacation villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Less than 15 miles from Walt Disney World, this villa offers a private backyard pool and hot tub (heated on request, fees payable). The 4-bedroom, 4 bathroomed house includes a fully equipped kitchen and spacious bedrooms with flat-screen TVs. Free Wi-Fi is available t …see more

from $110 / night

$710 - $1007 / week

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from $110 / night