50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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23,478 Vacation rentals

(51) 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 $64 / night

$321 - $484 / week

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avg. 3 hours 26 minutes

from $64 / night

(32) 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 $138 / night

$830 - $1,078 / week

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Responds fast!
avg. 2 hours 48 minutes

from $138 / night

(28) Excellent 

Certificate of Excellence

21

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

Certificate of Excellence

from $84 / night

$588 - $719 / week

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Responds fast!
avg. 3 hours 12 minutes

from $84 / night

(19) Excellent 

30

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 $126 / night

$915 - $1,046 / week

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avg. 3 hours 25 minutes

from $126 / night

(3) Excellent 

16

Vacation villa in Indian Creek

Kissimmee / Indian Creek

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
This superior Executive 4 bedroom villa is only a few short miles from Magic Kingdom,Epcot,Universal Studios (Harry Potter World) and all major attractions. Many homes promise luxury executive accommodation, but just compare with our home before you choose. Our 4 bedroo …see more

from $130 / night

$850 - $1,155 / week

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avg. 1 hour 51 minutes

from $130 / night

(10) Excellent 

24

Kissimmee Vacation villa rental

Kissimmee / Doral Woods

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The exclusive woodland setting of Doral Woods is an excellent place for relaxation and yet is within convenient reach of all the action of Disney, Universal, Sea World and Legoland and the other attractions. Be at one with nature in our unspoilt landscape. You can enjoy …see more

from $111 / night

$780 - $1,278 / week

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avg. 2 hours 21 minutes

from $111 / night

(46) Very Good 

Certificate of Excellence

12

Villa rental in Lindfields

Kissimmee / Lindfields

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunrise Villa is a luxurious villa close to all major attractions in a quiet, private & gated community in the town of Kissimmee. Our rate is from £525 per week .We are only 25 minutes from the airport & a stones throw away from Walt Disney World Orlando. Sunrise Villa …see more

Certificate of Excellence

from $85 / night

$595 - $824 / week

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from $85 / night

(35) Excellent 

Certificate of Excellence

56

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 150 mi
  • Swimming pool
TripAdvisor Certificate of Excellence winning villa 2017 & 2018! Welcome to Our Magnificently Luxurious Spacious 4 bedroom Modern Villa in Crescent Lakes Kissimmee Orlando. Our close to Disney home will make your Florida Vacation complete. There is lots of space to …see more

Certificate of Excellence

from $144 / night

$974 - $1,176 / week

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Responds fast!
avg. 1 hour 20 minutes

from $144 / night

(22) Excellent 

28

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 $125 / night

$850 - $1,046 / week

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Responds fast!
avg. 3 hours 7 minutes

from $125 / night

(10) Excellent 

14

Vacation villa in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
The villa has 4 bedrooms and 3 bathrooms, and sleeps 8 people comfortably. The south facing pool overlooks a wooded conservation area which provides a secluded location in which to relax. The lanai provides shade during the day, whilst the pool deck allows you to rela …see more

from $125 / night

$850 / week

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from $125 / night

(30) Very Good 

26

Vacation villa in Kissimmee

Central Florida / Kissimmee

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury 3 bed 2 bath villa can sleep 8. Large 30ft fully heated secluded pool. Only 20 minutes from Orlando airport & 30 minutes from theme parks & 1 hour from Kenedy space centre & cocoa beach. Also 1 hour from Bush Gardens & Clearwater beach to the west coast. Surounde …see more

from $85 / night

$587 - $1,044 / week

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from $85 / night

(22) Very Good 

51

Apartment rental in Kissimmee

Central Florida / Kissimmee

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 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

$585 / week

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from $85 / night

(20) Excellent 

18

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa is south west facing, so when you have had a busy day at the theme parks you can relax with a bbq around the pool, with its covered lania & ceiling fan to watch the sun go down. We have a fully fitted Games room,with pool table, foosball, dart board,Xbox, Wi …see more

from $118 / night

$647 - $2,346 / week

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from $118 / night

(37) Very Good 

36

Vacation villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • 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 to a …see more

from $98 / night

$588 - $686 / week

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avg. 2 hours 21 minutes

from $98 / night

(6) Excellent 

32

Villa rental in Kissimmee with shared pool, golf nearby

Kissimmee / Vista del lago

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
Three bedrooms, two bathrooms, clean and spacious. Large lounge dining room with TV, DVD, phone, full A/C. Modern kitchen. Master bedroom with full on-suite facilities and walk in shower. Full bathroom for other bedrooms. Screened sunroom Short stay/long stay special ra …see more

from $66 / night

$458 / week

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from $66 / night

(2) Excellent 

18

Kissimmee Vacation apartment rental

Central Florida / Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a newly renovated 1650 SF unit with an open floor plan. Well appointed modern furnishings with ceramic and porcelain flooring throughout. This is ideal for allergy sufferers. The four bedrooms contain 1 King, 2 Queen and 2 twin beds, respectively. There are thre …see more

from $100 / night

$700 / week

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from $100 / night

(23) Excellent 

Certificate of Excellence

28

Doral Woods Vacation villa rental

Kissimmee / Doral Woods

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
- 4 Bedrooms, 2 Queen, 2 Twin. En-suite to Master. Flat screen TV in Master and Queen. - Private heated pool, not overlooked. Optional pool heating charge £60/week, contact owner. Within mesh to keep those insects out. - 2 Bathrooms, shower cubicle in en-suite, shower …see more

Certificate of Excellence

from $102 / night

$660 - $693 / week

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Responds fast!
avg. 2 hours 36 minutes

from $102 / night

(45) Excellent 

Certificate of Excellence

28

Vacation villa in Kissimmee

Kissimmee / Doral Woods

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
AS A RESPONSIBLE OWNER, THE CALENDER FOR THIS PROPERTY IS ALWAYS KEPT UP TO DATE. See my Doral Woods video below and check out the latest updates, links & recommendations on my Doral Woods Florida Villa Facebook page. There's nothing quite like coming home to the com …see more

Certificate of Excellence

from $175 / night

$1,100 - $1,450 / week

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Responds fast!
avg. 3 hours 15 minutes

from $175 / night

(50) Excellent 

91

Vacation villa in Westside

Kissimmee / Westside

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 96 mi
  • Swimming pool
  • Child friendly
La Bella Vita is our newly refurbished Italian-style villa featuring 4 luxury bedrooms and 3.5 bathrooms in the highly desirable Westside community of Calabria and West Tuscany. A perfect location for your family vacation to Disney. It is situated in Kissimmee and jus …see more

from $135 / night

$935 - $1,150 / week

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avg. 1 hour 16 minutes

from $135 / night

(31) Excellent 

Certificate of Excellence

33

Villa accommodation in Kissimmee

Kissimmee / Cumbrian Lakes

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
Our villa is situated just 10 minutes from Disney and all its attractions and 5 minutes to shops and restaurants. Private heated pool fully screened and safety fence. Open plan lounge and formal dining area Fully fitted kitchen making preparing meals and snack …see more

Certificate of Excellence

from $105 / night

$641 - $889 / week

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Responds fast!
avg. 2 hours 15 minutes

from $105 / night

(14) Excellent 

22

Vacation home with shared pool in Kissimmee

Kissimmee / Trafalgar Village

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
The Trafalgar Village community is centred around the luxurious Trafalgar Village Center (or Clubhouse), a 2 minute stroll from the property with amenities that include a man made beach and lagoon, lakes (stocked for fishing), a pool and games arcade room, a 48 seat mov …see more

from $84 / night

$580 - $779 / week

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from $84 / night

(60) Excellent 

Certificate of Excellence

46

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 last 2 weeks November only £595 rental. This exclusive luxury property, with beautiful Italian themed fixtures and fittings is set in the highly desirable community of (Tuscany/Calabria) surrounded by small lakes, conservation area and Florida's woo …see more

Certificate of Excellence

from $125 / night

$752 - $1,176 / week

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Responds fast!
avg. 58 minutes

from $125 / night

(14) Excellent 

22

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a beautifully furnished vacation home near to all Disney theme parks, several good golf courses and a 5 minute drive from restaurants and shops. The villa sleeps 8 people and has four good sized bedrooms and two bathrooms. The villa is fully equip …see more

from $135 / night

$945 / week

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from $135 / night

(31) Very Good 

22

Vacation villa in Kissimmee City

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. Cable TV, free WIFI. The villa has …see more

from $77 / night

$458 - $608 / week

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from $77 / night

(1) Good 

30

Vacation apartment in Kissimmee

Central Florida / Kissimmee

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Found! Your Orlando vacation paradise. Spacious 1BR/1BA apartment located in a resort-style property in a close proximity to Disney Parks, Seaworld and Universal Studios. There is 24/7 front desk and security, 2 heated pools, hot tub, tennis courts, BBQ areas. Ideal for …see more

from $65 / night

$455 / week

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from $65 / night

(3) Excellent 

91

Villa accommodation in Kissimmee

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 $169 / night

$1,180 / week

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from $169 / night

(41) Excellent 

30

Villa rental in Cumbrian Lakes

Kissimmee / Cumbrian Lakes

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
As you enter our home through the glass front doors you will see the formal living room and dinning room to your right, as you walk forward the area opens up into the large fully equipped kitchen with breakfast nook and Family room with 60" cable TV, with access to Netf …see more

from $144 / night

$980 - $1,176 / week

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from $144 / night

(6) Very Good 

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 / week

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from $85 / night

(15) Excellent 

36

Vacation home rental

Kissimmee / Crescent Lakes

5 13 3 nights min

  • 5 bedrooms
  • sleeps 13
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Well maintained fully furnished 5 bed 3.5 bath home with 25x15 heated private pool and spa. Private garden overlooking lake. Covered lanai with south facing sundeck and pool furniture. The fabulous sun drenched pool deck and shimmering waters of our private pool offer a …see more

from $105 / night

$621 - $1,133 / week

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from $105 / night

(20) Very Good 

90

Vacation townhouse in Kissimmee

Kissimmee / Terra Verde Resort

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Palm Heaven Villa has everything you need for a fantastic, relaxing family holiday. Four large bedrooms mean everyone can have plenty of space, and can sleep 8 very comfortably: one queen bedroom is downstairs with an adjacent full bathroom; upstairs is the large master …see more

from $131 / night

$784 - $980 / week

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from $131 / night

(2) Very Good 

52

Villa rental in Kissimmee with golf nearby

Kissimmee / Indian Ridge

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
We have the ideal location for a holiday close to the fabulous Central Florida attractions - including Walt Disney World, Universal and Sea World. With 4 bedrooms and plenty of space, the Indian Ridge Villa is ideal for small families, large families or two families sh …see more

from $130 / night

$654 - $909 / week

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from $130 / night

(11) Excellent 

26

Vacation villa in Formosa Gardens

Kissimmee / Formosa Gardens

7 16 min stay varies

  • 7 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $299 / night

$2,091 - $2,744 / week

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from $299 / night

(10) Very Good 

13

Vacation villa with shared pool, golf nearby in Kissimmee

Kissimmee / Windsor Palms

6 14 4 nights min

  • 6 bedrooms
  • sleeps 14
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxury rental villa is located within the 5 star secure gated resort of Windsor Palms in Kissimmee, Florida. Windsor Palms is one of the most sought after rental locations for families staying in Orlando & Kissimmee. Windsor Palms is the closest residential communi …see more

from $216 / night

$915 / week

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from $216 / night

(8) Very Good 

45

Vacation villa rental

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Whether you wish to hit the Theme Parks, go shopping at the Florida Mall or along International Drive, play some fantastic golf, or simply relax by the pool, this home is exactly what you are looking for. It is fully licensed and professionally managed through a conveni …see more

from $108 / night

$673 - $817 / week

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Responds fast!
avg. 3 hours 48 minutes

from $108 / night

(36) Excellent 

Certificate of Excellence

57

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Over 12 Years listed with Holiday Lettings/ Trip Advisor. 5 STAR Trip Advisor Reviews, please read them, we hope you find them very helpful! We have been visited & verified by Trip Advisor. Perfect Location and Discounts for bookings over 2 weeks and FREE food arrival p …see more

Certificate of Excellence

from $164 / night

$1,078 - $1,301 / week

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Responds fast!
avg. 1 hour 16 minutes

from $164 / night

24

Emerald Isle Kissimmee Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

8 16 min stay varies

  • 8 bedrooms
  • sleeps 16
  • min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Only 3 miles to Disney, 14 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful community with 24/7 guarded gate. …see more

from $300 / night

$1,425 - $2,626 / week

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from $300 / night

(13) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
A Brand new 2010, '5' Star Luxurious 6 bed, 4 bath fully air conditioned executive Villa in Archfeld Blvd, Windsor Hills Resort, with Free local, National & international call to over 40 destinations & free wireless internet. You also have your own private heated Pool …see more

from $216 / night

$1,405 - $1,895 / week

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Responds fast!
avg. 1 hour 42 minutes

from $216 / night

(10) Excellent 

25

Vacation home with shared pool in Kissimmee

Kissimmee / Lucaya Village

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Property Description: Guests: 10 / Bedrooms: 4 / Bathrooms: 3 / Community: Lucaya Village / Type: Townhome - Townhouse with 4 bedrooms and 3 bathrooms - sleeps up to 10 people comfortably - Less than 5 minutes from supermarkets. - Gated community. - Electronic Code - fr …see more

from $125 / night

$970 / week

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Responds fast!
avg. 2 hours 39 minutes

from $125 / night

(25) Excellent 

24

Kissimmee Vacation villa rental

Kissimmee / Lake Berkley

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our home is a luxury 4-bedroom, 3-bathroom home with its own private screened pool. The villa is located in Lake Berkley, a peaceful and gated subdivision situated approximately 10 min from the Walt Disney World entrance and is conveniently located for the other theme p …see more

from $93 / night

$647 - $915 / week

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from $93 / night

(1) Excellent 

17

Vacation villa in Kissimmee

Kissimmee / Cumbrian Lakes

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 100 mi
  • Swimming pool
You will feel it the moment you pass the entry gates to this beautiful new community. A sense of peace and harmony with nature. Pleasing street-scapes are lined with ancient oak trees, giving shade as well as a taste of Florida's natural beauty. Sparkling lakes provide …see more

from $224 / night

$1,568 / week

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from $224 / night