50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

Close

View larger map

Also consider

Emerald Isle Kissimmee
51 properties
Windsor Hills Resort
28 properties
Kissimmee City
27 properties
Paradise Palms
20 properties
Lake Berkley
20 properties
Windsor Palms
19 properties
Cumbrian Lakes
18 properties
Lindfields
17 properties
Bellavida Resort
15 properties
Terra Verde Resort
15 properties
Seasons Resort
11 properties
Compass Bay
10 properties
Crescent Lakes
10 properties
Formosa Gardens
9 properties
Venetian Bay Villages
9 properties
Doral Woods
8 properties
Orange Lake Resort
8 properties
Trafalgar Village
8 properties
Encantada Resort
7 properties
Eagle Pointe
6 properties

Kissimmee

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

4,646 Vacation rentals

(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 $120 / night

$839 - $903 / week

Book View

from $120 / night

(56) 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

Book View

from $117 / night

(9) 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

Book View

from $168 / night

(10) Very Good 

20

Vacation townhouse in Kissimmee

Kissimmee / Paradise Palms

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
Paradise Palms is situated in one of the best area's in Kissimmee, only minutes from Disney, Universal Studios, Island of Adventure and sea world. With its terrific shopping malls and fantasic restaurants this is the place to stay. Only a Couple of minutes we als …see more

from $122 / night

$787 - $1200 / week

Book View

from $122 / night

(45) Excellent 

91

Vacation villa in Westside

Kissimmee / Westside

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • 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

$930 - $1150 / week

Book View

from $135 / 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 charge. All local …see more

from $165 / night

$1095 - $1500 / week

Book View

from $165 / night

(33) 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 $129 / night

$774 - $903 / week

Book View

from $129 / night

(1) Excellent 

45

Kissimmee Vacation villa accommodation

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
A home from home, the British owners spend as much time as possible in the villa themselves. The villa is situated on a large lot and the private south facing heated pool and jacuzzi back onto a wooded area. Pool heating for cooler months is available for an additional …see more

from $85 / night

$595 - $805 / week

Book View

from $85 / night

(18) 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 Privat …see more

from $78 / night

$465 - $903 / week

Book View

from $78 / night

(14) 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

Inquire View

from $117 / night

(32) Excellent 

13

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

$850 - $920 / week

Book View

from $125 / night

(19) Excellent 

23

Kissimmee Vacation villa rental

Kissimmee / Doral Woods

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Doral Woods community is set within a Wildlife Conservation area. The location has a very private and unique semi rural setting in which peace and tranquility are the order of the day. Our recently refurbished Villa is built on an 1/4 acre landscaped plot, our swimmi …see more

from $128 / night

$897 - $1026 / week

Book View

from $128 / night

(3) 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

Book View

from $195 / night

(4) Very Good 

12

Kissimmee Vacation villa rental

Kissimmee / Cumbrian Lakes

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury 4 Bed, 3.5 Bath villa is situated in the exclusive, secure gated community of Cumbrian Lakes. Set in a prime position backing onto a conservation area (over 200 acres) not overlooked, secluded and peaceful. Conveniently situated just off 192 and all …see more

from $110 / night

$795 / week

Book View

from $110 / night

(3) 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 $70 / night

$491 - $633 / week

Book View

from $70 / night

(29) 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

Book View

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

Book View

from $185 / 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 $296 / night

$2064 - $2580 / week

Book View

from $296 / night

(13) 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, Wi …see more

from $117 / night

$639 - $807 / week

Book View

from $117 / 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 peace of min …see more

from $193 / night

$1349 - $1929 / week

Book View

from $193 / night

13

Venetian Bay Villages Vacation townhouse rental

Kissimmee / Venetian Bay Villages

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 Bedrooms, 3 bathrooms, sleeps 10 Venetian Bay Villages is an upscale, family-friendly, GATED resort community – developed and built for a vacation lifestyle. The community is only seven miles from the entrance to Disney World and conveniently located to ALL of …see more

from $104 / night

$645 / week

Book View

from $104 / 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 $104 / night

$723 - $1200 / week

Book View

from $104 / night

(25) Very Good 

27

Vacation home in Kissimmee

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A superb villa in an ideal central position. The huge South facing pool area sets this villa apart from others, as the impressive pool screen extends out from the roof creating a large spacious area. Just perfect for families to relax and enjoy. A quiet residential cul- …see more

from $103 / night

$672 - $1350 / week

Book View

from $103 / night

(27) Excellent 

56

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 10 Years listed with Holiday Lettings. 5 STAR Trip Advisor Reviews, please read them. They are very helpful! Perfect Location and Discounts for bookings over 2 weeks and FREE food arrival pack as standard to all our guests! Fully Air Conditioned + Paddle fans in al …see more

from $162 / night

$1097 - $1258 / week

Book View

from $162 / night

(19) 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 $135 / night

$813 - $1056 / week

Book View

from $135 / night

(13) Excellent 

44

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

$671 - $1007 / week

Book View

from $97 / night

(12) Excellent 

24

Vacation villa in Doral Woods

Kissimmee / Doral Woods

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Palm Tree Villa Florida, is tucked away in the much sought after location of Doral Woods. This large 4 Bedroom, 3 Bathroom villa, is ideal for making the perfect vacation. This is our own holiday home, so the furnishings are to a high standard, as you can see from the …see more

from $129 / night

$897 - $1129 / week

Book View

from $129 / night

(1) 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 $135 / night

$941 - $1344 / week

Book View

from $135 / night

(16) Excellent 

49

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 60 mi
  • Swimming pool
Your beautiful vacation home is at Eagle Point, Kissimmee, one of the best possible locations for access to Orlando's famous theme parks, attractions and Golf Courses. When you stay in this executive pool home, you will get great views, great decor and a private locatio …see more

from $110 / night

$725 - $825 / week

Book View

from $110 / 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 restaurant …see more

from $130 / night

$850 - $1165 / week

Book View

from $130 / night

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

Inquire View

from $136 / night

(20) Excellent 

25

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Swimming pool
The home is a beautifully furnished and spacious property, well-maintained by our Management Company. It is situated off Highway 192 in the prestigious Emerald Island Resort, one of the premium vacation communities in the area, a tropical oasis nestled within prote …see more

from $168 / night

$1129 / week

Book View

from $168 / 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

Book View

from $115 / night

(11) Excellent 

14

Vacation villa with swimming pool in Kissimmee

Central Florida / Kissimmee

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This spacious detatched 4 bedroom villa offers exellent value per person. It is in an ideal location for all of the attractions in the Orlando / Kissimmee area. It is situated just off the 192 between mile markers 13 & 14 on a quiet residential estate. We do not use a …see more

from $84 / night

$576 - $640 / week

Book View

from $84 / night

(15) Excellent 

29

Kissimmee Vacation villa rental

Kissimmee / Seasons Resort

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 110 mi
  • Swimming pool
Wonderful, private vacation home just 10 minutes from Disney World. This property is a stylish vacation rental in the heart of Kissimmee, set on a quiet lakeside development just off the 192 highway. The fantastic games room & south-facing private pool with Jacuzzi mak …see more

from $125 / night

$845 - $1165 / week

Book View

from $125 / night

(21) 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 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 $65 / night

$484 - $936 / week

Book View

from $65 / 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

Book View

from $110 / 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

Book View

from $200 / night

28

Vacation home in Kissimmee

Central Florida / Kissimmee

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
On Windsor at Westside, a gated community. The house has a large private South East facing pool and spa. The screened patio / lanai has been extended to give more room to sunbath. Or to lounge and relax. The largest on the community. Guests also have access to a gas …see more

from $300 / night

$1800 - $2520 / week

Book View

from $300 / night

(30) 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 $46 / night

$283 - $484 / week

Book View

from $46 / night

1