50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

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Emerald Isle Kissimmee
39 properties
Windsor Hills Resort
18 properties
Kissimmee City
16 properties
Paradise Palms
15 properties
Lindfields
15 properties
Lake Berkley
13 properties
Bellavida Resort
12 properties
Windsor Palms
12 properties
Terra Verde Resort
11 properties
Cumbrian Lakes
11 properties
Doral Woods
8 properties
Compass Bay
7 properties
Formosa Gardens
6 properties
Seasons Resort
6 properties
Crescent Lakes
5 properties
Indian Creek
5 properties
Trafalgar Village
5 properties
Coral Cay
5 properties

Kissimmee

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22,375 Vacation rentals

(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 $134 / night

$810 - $1,052 / week

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from $134 / 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 $123 / night

$894 - $958 / week

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avg. 3 hours 45 minutes

from $123 / night

(40) Excellent 

23

Vacation home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • 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 $119 / night

$829 - $957 / week

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avg. 2 hours 3 minutes

from $119 / night

(19) 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 $115 / night

$632 - $2,289 / week

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from $115 / night

(48) Excellent 

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 $63 / night

$313 - $472 / week

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avg. 3 hours 6 minutes

from $63 / night

(30) Excellent 

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

from $103 / night

$626 - $830 / week

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avg. 1 hour 22 minutes

from $103 / night

(28) Excellent 

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

from $82 / night

$574 / week

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from $82 / night

(49) 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 7 minutes

from $135 / night

(21) 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 $121 / night

$827 - $1,018 / week

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Responds fast!
avg. 3 hours 20 minutes

from $121 / night

(26) Excellent 

Certificate of Excellence

19

Villa rental in Kissimmee with swimming pool

Kissimmee / Bellavida Resort

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious 4 bedroom villa on the prestigious Bella Vida resort. 10-15 mins from all attractions This villa enjoys a lakefront location together with its own pool. Access to the local clubhouse is free which allows guests the use of a fitness room, pool and play area. W …see more

Certificate of Excellence

from $115 / night

$753 / week

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from $115 / 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 47 minutes

from $130 / night

(28) 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 $83 / night

$574 - $1,021 / week

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from $83 / 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

(46) Very Good 

20

Vacation home in Crescent Lakes

Kissimmee / Crescent Lakes

4 11 3 nights min

  • 4 bedrooms
  • sleeps 11
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our very special lakeside villa. You'll love the feeling of light and space as you enter the vill,with over 3000sq ft of living space this feeling just goes on. The villa is beautifully furnished and presented with lots of luxurious extras that make our villa …see more

from $109 / night

$702 / week

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from $109 / 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 $109 / night

$763 - $1,250 / week

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avg. 2 hours 35 minutes

from $109 / night

(14) Very Good 

50

Vacation villa rental

Kissimmee / Trafalgar Village

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • 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 $109 / night

$702 / week

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from $109 / night

(30) Excellent 

37

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 $139 / night

$986 / week

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avg. 44 minutes

from $139 / 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 $91 / night

$632 - $893 / week

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from $91 / night

(28) Excellent 

38

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 peace of min …see more

from $190 / night

$1,333 - $1,907 / week

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avg. 3 hours 45 minutes

from $190 / night

(92) Excellent 

Certificate of Excellence

25

Vacation villa in Kissimmee

Kissimmee / Bass Lakes Estate

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
RATED EXCELLENT on Trip Advisor with 88 reviews and Certificate of Excellence 2017. Orlando Florida is the perfect holiday destination for all ages with sunshine all year round. It hosts the world's greatest theme parks and most, including Disney World, are very conveni …see more

Certificate of Excellence

from $90 / night

$619 - $766 / week

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Responds fast!
avg. 1 hour 47 minutes

from $90 / night

(30) 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 $76 / night

$447 - $593 / week

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from $76 / night

(35) Very Good 

58

Vacation home rental

Kissimmee / Lindfields

2 5 5 nights min

  • 2 bedrooms
  • sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 90 mi
  • Swimming pool
A WONDERFUL OPPORTUNITY TO ENJOY AN AMAZING VACATION IN THE SUNSHINE STATE OF FLORIDA. THE ACOMMODATION IS SITUATED IN A QUIET RESIDENTIAL AREA JUST 10 MINUTES DRIVE FROM ALL THE DISNEY ATTRACTIONS. THE TOWNHOUSE IS JUST OFF THE 192 IN KISSIMMEE AND JUST A SHORT DRIV …see more

from $64 / night

$447 / week

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avg. 1 hour 34 minutes

from $64 / night

(13) Excellent 

42

Vacation villa rental

Kissimmee / Indian Ridge Oaks

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
We welcome you to take a look at our villa close to all the magic, yet in a peaceful and tranquil setting. Indian Ridge Oaks - one of the closest communities to Disney / 4 miles to Disney Maingate - south facing pool ***** Luxury villa in a superb location …see more

from $97 / night

$822 - $1,027 / week

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avg. 3 hours 29 minutes

from $97 / night

(18) Very Good 

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
Bellavida is a stunning gated resort just off the 192 behind Medieval Times and Walmart. Our home is a beautiful Mediterranean style detached villa property which has been designed, built and decorated to be the amongst the best. With 6 bedrooms and 5 1/2 bathrooms th …see more

from $211 / night

$1,473 / week

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avg. 2 hours 10 minutes

from $211 / night

(43) Very Good 

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

from $83 / night

$579 - $801 / week

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from $83 / night

(47) Excellent 

Certificate of Excellence

21

Vacation villa in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Formosa Blvd Villa, is a single storey detached property on a large corner plot with a south facing pool/spa. large pool deck area Its is situated in Kissimmee Florida, approx 3 miles from Walt Disney Parks. 1 king with master ensuite, 1 double and two twin rooms all w …see more

Certificate of Excellence

from $110 / night

$766 - $798 / week

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Responds fast!
avg. 1 hour 2 minutes

from $110 / night

(5) Very Good 

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 $69 / night

$485 / week

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from $69 / night

(7) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Country Creek

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful family owned villa is located only 10 mins from WDW and close to many other attractions such as Sea World, Aquatica, Universal Studios and Universal Islands of Adventure. Our home from home is comfortably furnished and equipped with all the amenities to m …see more

from $102 / night

$670 - $829 / week

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from $102 / night

(18) Excellent 

Certificate of Excellence

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 players in the living room and all bedrooms. Please state whether you would require POOL HEAT for …see more

Certificate of Excellence

from $108 / night

$757 - $1,068 / week

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from $108 / night

(59) Excellent 

Certificate of Excellence

42

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
October Special - gap of 6 nights 9th -15th just £600. 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 woodland …see more

Certificate of Excellence

from $122 / night

$734 - $1,148 / week

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Responds fast!
avg. 1 hour 15 minutes

from $122 / 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 $211 / night

$893 / week

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Responds fast!
avg. 3 hours 18 minutes

from $211 / night

(28) 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 $128 / night

$574 - $759 / week

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from $128 / 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 $292 / night

$2,041 - $2,678 / week

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from $292 / night

(31) Excellent 

Certificate of Excellence

58

Vacation townhouse with shared pool in Trafalgar Village

Kissimmee / Trafalgar Village

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 80 mi
  • Swimming pool
The home is a 3 Bed town home at the Trafalgar Village Resort which is located on Poinciana Boulevard just 10 minutes south of highway 192 and approx 15 – 20 minutes to Disney. The home has been furnished to a very good standard and has a King, and two Queen bedrooms …see more

Certificate of Excellence

from $51 / night

$357 - $893 / week

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Responds fast!
avg. 2 hours 38 minutes

from $51 / night

(20) Very Good 

24

Townhouse rental in Kissimmee

Kissimmee / Regal Oaks

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Home comforts just miutes from the magical World of Disney. The home has 2 spacious master bedrooms with King Size Beds, both with an en-suite bathroom and one with a balcony. The third bedroom is furnished with 2 twin beds great for persons with limited moblity. There …see more

from $112 / night

$784 / week

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Responds fast!
avg. 2 hours 44 minutes

from $112 / 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 $121 / night

$827 / week

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from $121 / 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

(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 $102 / night

$574 - $1,106 / week

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from $102 / night

(10) Excellent 

20

Bellavida Resort Vacation villa rental

Kissimmee / Bellavida Resort

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • 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 $181 / night

$1,148 - $1,276 / week

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from $181 / night

(16) Very Good 

48

Vacation villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa is situated in the beautiful Emerald Island Resort, regarded as one of the best resorts in the area. It is located south of Hwy 192 near Mile Marker 5 just minutes from I4. It is approximately 4 miles to the gates of Walt Disney World and within easy reach of …see more

from $120 / night

$840 / week

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from $120 / night