50 Best Kissimmee Apartments on Holiday Lettings - Vacation rentals

Close

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

23,562 Vacation rentals

(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 $114 / night

$627 - $2,272 / week

Book View

from $114 / 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 $90 / night

$627 - $886 / week

Book View

from $90 / night

(13) Good 

Certificate of Excellence

100

Kissimmee Vacation home rental

Central Florida / Kissimmee

4 10 6 nights min

  • 4 bedrooms
  • sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This immaculate 4 bedroom, 3 bath, family vacation villa is ideally situated only 3 miles from Disney World! The villa overlooks a tranquil lake, a home to herons and other wildlife all year round, and from here it's a short journey to all the major attractions in and …see more

Certificate of Excellence

from $166 / night

$1,159 / week

Book View

from $166 / night

(11) 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

$762 - $1,248 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from $109 / 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

Book View

from $135 / 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 $96 / night

$573 - $669 / week

Book View

Responds fast!
avg. 1 hour 0 minutes

from $96 / 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 $121 / night

$823 - $1,013 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from $121 / 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 $83 / night

$573 - $1,019 / week

Inquire View

from $83 / night

(30) 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 $87 / night

$605 - $701 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from $87 / night

(53) Excellent 

23

Vacation condo with golf nearby in Kissimmee

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • 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

$452 - $471 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from $63 / 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 $291 / night

$2,037 - $2,674 / week

Inquire View

from $291 / night

(14) Very Good 

50

Vacation villa rental

Kissimmee / Trafalgar Village

4 8 4 nights min

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

from $109 / night

$701 / week

Book View

from $109 / night

(34) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $109 / night

$631 - $758 / week

Book View

Responds fast!
avg. 2 hours 23 minutes

from $109 / 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

$892 - $1,019 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from $123 / night

(15) Excellent 

Certificate of Excellence

24

Villa rental in Kissimmee

Central Florida / Kissimmee

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
THE VILLA with it,s fully screened, south facing 30x15ft swimming pool with underwater lighting for evening swimming and has free solar heating with electronic control and electric heating for the winter months. The large deck with sun or shade is equipped with new luxu …see more

Certificate of Excellence

from $96 / night

$624 - $694 / week

Book View

Responds fast!
avg. 1 hour 1 minutes

from $96 / 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 $134 / night

$809 - $1,051 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from $134 / 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

Book View

Responds fast!
avg. 1 hour 51 minutes

from $130 / night

(4) Excellent 

51

Vacation villa in Kissimmee

Kissimmee / Hamilton's Reserve

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 85 mi
  • Swimming pool
This luxury home is set in a very quiet residential neighbourhood and within easy reach (15 to 20 minutes) of all the Disney theme and water parks, Universal Studios and Islands of Adventure, Sea World, Legoland, etc. The Buena Vista Shopping Mall is about a 5 minutes …see more

from $155 / night

$925 - $1,295 / week

Book View

from $155 / night

(6) Good 

34

Kissimmee Vacation villa rental

Central Florida / Kissimmee

4 8 min stay varies

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

from $110 / night

$770 - $1,050 / week

Book View

from $110 / night

(10) Excellent 

48

Apartment rental in Kissimmee with shared pool

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/traditional furnishings with carpet flooring throughout. The three bedrooms contain 1 King, 1 Queen and 2 twin beds, respectively. There are two full bathrooms, and a jacuzzi in the en …see more

from $85 / night

$595 / week

Book View

from $85 / night

(32) Excellent 

Certificate of Excellence

26

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 $102 / night

$624 - $866 / week

Book View

Responds fast!
avg. 3 hours 32 minutes

from $102 / night

(36) 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 $140 / night

$949 - $1,210 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from $140 / night

(1) Excellent 

0

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 $255 / night

$1,783 / week

Book View

from $255 / night

(3) Good 

12

Kissimmee Vacation townhouse rental

Kissimmee / Terra Verde Resort

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
This home is located on the well sought after Terra Verde resort with guarded entry and Clubhouse facilities. The 3 bed townhome is situated in a quiet cul de sac. It has its own private patio area. It also has the advantage of catching the sun most of the day. There i …see more

from $77 / night

$491 / week

Book View

from $77 / 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 $121 / night

$669 - $828 / week

Book View

from $121 / 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

$605 - $949 / week

Book View

from $102 / night

(2) Very Good 

18

Vacation villa with shared pool, golf nearby in Orange Lake Resort

Kissimmee / Orange Lake Resort

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This family-friendly resort, spanning more than 1,400 acres, is right on the doorstep of Walt Disney World and offers a wide variety of activities on both water and land. Villas, apartments and suites are available. Holiday Inn Club Vacations at Orange Lake Resor …see more

from $218 / night

$1,528 / week

Book View

from $218 / 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 $128 / night

$764 - $955 / week

Book View

from $128 / night

(51) 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

Book View

Responds fast!
avg. 1 hour 16 minutes

from $135 / 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

Book View

from $85 / 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 $104 / night

$709 - $792 / week

Book View

Responds fast!
avg. 3 hours 34 minutes

from $104 / night

(27) 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

$751 / week

Book View

from $115 / 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

$481 / week

Book View

from $69 / night

(2) Excellent 

24

Villa accommodation in Kissimmee with swimming pool

Central Florida / Kissimmee

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Sunnyside Villa is located in Kissimmee,1.2 miles from the main highway 192 which has various shop outlets , Restaurants 24 hour wallmart is in walking distance. Disney world is a 20 minute drive away.Also there is a nature reserve close by were you can enjoy canoeing a …see more

from $90 / night

$713 / week

Book View

from $90 / night

(53) Excellent 

Certificate of Excellence

62

Vacation villa in Kissimmee

Kissimmee / Lindfields

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 65 mi
  • Swimming pool
This villa has a fantastic large pool with jacuzzi hot tub backing on to a lovely lake and forest. In colder months you can choose to have the pool heated for an extra charge. The pool is not overlooked so you will not find excited children spoiling your peaceful evenin …see more

Certificate of Excellence

from $110 / night

$764 - $892 / week

Book View

from $110 / night

(11) Excellent 

19

Kissimmee Vacation villa rental

Kissimmee / Oak Island Cove

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
Detached Villa, Private Heated Pool, 4 large Bedrooms, fully equipped, Close to Disney, Our Disney Home from Home, Close to restaurants and shops, overlooking beautiful lake. A lovely 2 story Disney home on Oak Island Harbor in Kissimmee, Florida! The location of this …see more

from $127 / night

$886 / week

Book View

Responds fast!
avg. 3 hours 22 minutes

from $127 / 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

Book View

from $100 / night

20

Vacation villa in Kissimmee

Central Florida / Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Perfectly located near Disney, this 4 bed luxury villa with private pool and games room is a home from home. Fully equipped kitchen, separate utility room, computer wth high speed internet and secure WIFI, tv with 150 cable channels. Mickey themed bedroom and Winnie T …see more

from $144 / night

$1,006 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from $144 / night

(20) 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 $109 / night

$758 - $1,070 / week

Book View

from $109 / night

(43) 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 $140 / night

$955 - $1,146 / week

Inquire View

from $140 / night

Also consider