50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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Emerald Isle Kissimmee
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Kissimmee

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4,277 Vacation rentals

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(3) Excellent 

45

Kissimmee Vacation townhouse rental

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
4 Bedrooms / 3 bathrooms - ground floor comprising covered entrance porch, entrance foyer, kitchen, dining area, great room, covered terrace, ground floor double bedroom with bathroom. Stairs leading to - First floor comprising master bedroom with walk in wardrobes and  …see more

from $75 / night

$521 - $782 / week

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from $75 / night

(27) Excellent 

24

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
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 $93 / night

$651 - $744 / week

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from $93 / night

(16) Very Good 

17

Vacation villa in Seasons Resort

Kissimmee / Seasons Resort

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to our home on Seasons. It is a St Vincent model built by Park Square Homes and is 2765 Sq. Foot of Executive quality. It is a luxurious 5 Bedroom – 4 Bathroom Villa, which has 2 Master Suites and 3 other Bedrooms - which comfortably sleep 10 with ease, a  …see more

from $75 / night

$447 - $868 / week

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from $75 / night

Featured properties

(27) Very Good 

12

Villa rental in Lindfields with swimming pool

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 £400 per week .We are only 25 minutes from the airport & a stones throw away from Walt Disney World Orlando.  …see more

from $76 / night

$527 - $744 / week

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from $76 / night

(54) 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  …see more

from $112 / night

$589 - $899 / week

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from $112 / night

(10) Very Good 

20

Vacation villa rental

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
A luxurious 4 bedroom, 3 bathroom vacation villa features a large private south facing pool and spa with conservation view plus fully air conditioned rooms and tv's and dvd's in living room and all bedrooms. The home is on the superb Emerald Island Resort an  …see more

from $93 / night

$651 - $912 / week

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from $93 / night

(21) 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 of  …see more

from $85 / night

$589 / week

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from $85 / night

(28) Very Good 

24

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 $44 / night

$272 - $465 / week

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from $44 / night

(8) 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 $162 / night

$1129 - $1488 / week

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from $162 / night

(17) Excellent 

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 $178 / night

$1240 - $1612 / week

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from $178 / night

(6) Excellent 

24

Vacation villa with golf nearby in Kissimmee

Kissimmee / Bellavida Resort

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Visit our owner website at the bottom of the page to view our 360 degree walk-through video: This is a a beautiful Mediterranean style property which has been designed, built and decorated to be the amongst the best. With 6 bedrooms and 5 1/2 bathrooms this is the per  …see more

from $205 / night

$1433 / week

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from $205 / 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 $186 / night

$1296 / week

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from $186 / night

(3) Excellent 

24

Villa rental in Kissimmee

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Stylish vacation home, sleeps 8, with private pool & spa pool. Located in the gated resort of Lake Berkley in Kissimmee with excellent resort amenities for you to enjoy. You are located minutes away from Disney, all attractions, theme parks & there are many re  …see more

from $131 / night

$851 - $1165 / week

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from $131 / night

(17) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Bellavida Resort

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Brand new Luxury 6 bedroom with 51/2 bath, fully air-conditioned. It is complete with heated pool and spa on an extended screened- deck area with speaker system, and looks directly onto the lake.With a 'state-of -the -art' alarm system giving you complete pe  …see more

from $185 / night

$1296 - $1854 / week

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from $185 / night

(20) Excellent 

24

Vacation townhouse rental

Kissimmee / Encantada Resort

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 50 mi
  • Swimming pool
  • Child friendly
THE HOUSE Interior designed 4 bedroomed house, sleeps 8, with (heated) private pool located in the beautiful 5 star Encantada resort. The resort itself is a "Hidden Gem" with the lake-facing property situated just a stone's throw away from the main  …see more

from $118 / night

$794 - $1178 / week

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from $118 / night

(24) 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 $87 / night

$602 - $707 / week

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from $87 / night

(5) Excellent 

30

Vacation villa in Kissimmee

Kissimmee / Seasons Resort

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This villa offers all the comforts of home & is a great base for your Disney vacation. The home comes with free wifi & local calls, cable TV, free parking, full laundry facilities & is fully air conditioned. These are provided for guests at no extra char  …see more

from $166 / night

$1096 - $1500 / week

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from $166 / night

(29) Excellent 

20

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 $125 / night

$851 - $920 / week

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from $125 / night

(2) 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

$596 / week

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from $85 / night

(5) Excellent 

28

Vacation home rental

Kissimmee / Emerald Isle Kissimmee

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 50 mi
  • Swimming pool
This home has it all !! *Newly Installed Granite kitchen worktops* Our 3,400sqft beautifully decorated Villa is a Luxurious 5 star, 7 bedroom, 5 Bath home, a Private Screened-in South Facing Pool and Jacuzzi with a beautiful view over a lake and preserve, (no homes beh  …see more

from $200 / night

$1394 / week

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from $200 / night

(20) 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 $124 / night

$558 - $670 / week

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from $124 / night

(17) 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 $81 / night

$558 - $620 / week

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from $81 / night

(14) Very Good 

24

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

from $87 / night

$596 - $744 / week

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from $87 / night

(25) 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 $136 / night

$946 - $1085 / week

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from $136 / night

(29) Excellent 

90

Villa rental in Kissimmee with swimming pool

Kissimmee / Eagle Pointe

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our beautiful villa is located just minutes away from the Disney theme parks and other attractions in Orlando, Florida. For the holiday of a lifetime, a vacation in our villa will provide you with spacious accommodation and your own private, south-facing swimming pool w  …see more

from $81 / night

$565 - $686 / week

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from $81 / night

(8) 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 $284 / night

$1984 - $2480 / week

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from $284 / night

(16) Excellent 

27

Vacation villa with swimming pool in Kissimmee

Kissimmee / Indian Ridge

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
The villa is air conditioned, carpeted and ceramic floor tiled to a very high standard with a family room/dining area, front games room . There are ceiling fans in all rooms for your added comfort. The south facing pool is solar heated and totally enclosed in mesh scree  …see more

from $93 / night

$651 - $775 / week

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from $93 / night

(13) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Windsor Palms

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • 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 $114 / night

$794 - $868 / week

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from $114 / night

(9) 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 $100 / night

$695 - $1154 / week

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from $100 / night

(27) 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 $58 / night

$400 - $461 / week

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from $58 / night

(12) Excellent 

18

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 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  …see more

from $112 / night

$614 - $775 / week

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from $112 / night

(8) Very Good 

24

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
Positioned on Oak Island Cove next to Formosa Gardens, this is one of the most exclusive vacation sub rental divisions in Central Florida. Every amenity is close at hand for a wonderful vacation. No other location boasts a 5 minute journey to Disney World, Orlando. The  …see more

from $164 / night

$1147 - $1482 / week

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from $164 / 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 Refurbish  …see more

from $116 / night

$775 - $946 / week

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from $116 / night

(38) Excellent 

39

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A stunning property in Kissimmee, Florida with all the home comforts to ensure a truly wonderful vacation. Within 8 minutes drive of Disney Main Gate. LUXURY, STYLE AND COMFORT. Country Creek Estates is a beautiful, well maintained community that offers peace and tranqu  …see more

from $100 / night

$614 - $639 / week

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from $100 / night

(45) Excellent 

39

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
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 woodlands. The villa with fully automated Jacuzzi and pool  …see more

from $124 / night

$738 - $1147 / week

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from $124 / night

(20) Very Good 

17

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. 3 TV's all with cable, VCR and  …see more

from $81 / night

$428 - $806 / week

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from $81 / night

(13) 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'  …see more

from $112 / night

$720 - $961 / week

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from $112 / night

(6) 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  …see more

from $151 / night

$1156 / week

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from $151 / night

(17) Excellent 

23

Vacation townhouse in Kissimmee

Kissimmee / Encantada Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Your holiday home is accessed via modern secure gated entry. Housed within a gated resort accessed by security code, or opened by the security staff on duty at the entrance. Disney World is but a short, pleasant drive away. You will feel relaxed and comfortable in this  …see more

from $80 / night

$496 - $1070 / week

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from $80 / night

(31) Excellent 

23

Vacation home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sun Quest Villa is located on the small and peaceful community of Oak Island Cove. The property is an exceptionally spacious and luxuriously decorated 5 bedroom 4 bathroom home with fully screened private pool and hot tub. Oak Island Cove is one of the closest and most  …see more

from $124 / night

$744 - $868 / week

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from $124 / night

1