Villas with a pool Kissimmee | Apartments to rent with swimming facilities

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Also consider

Emerald Isle Kissimmee
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Kissimmee City
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Lake Berkley
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Lindfields
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Terra Verde Resort
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Bellavida Resort
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Cumbrian Lakes
20 properties
Crescent Lakes
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Villas Indian Creek
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Regal Oaks
12 properties
Compass Bay
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Sunset Lakes
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Venetian Bay Villages
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Seasons Resort
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Villas Formosa Gardens
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Eagle Pointe
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Encantada Resort
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3,131 Holiday homes

Filters applied: Swimming pool (3,131)

Travellers going to Kissimmee are booking December dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

1 / 51

See The Mouse Town House - Windsor Hills Resort townhouse sleeps 8

Kissimmee / Windsor Hills Resort

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
Welcome to our See The Mouse Townhouse situated just two miles south of the Walt Disney World resort.The Townhouse is luxuriously furnished and consists of three bedrooms all with en-suite bath/shower rooms on two levels. There is a plunge/spa pool (can be heated in win  …see more

from £75 / night

£575 - £650 / week

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from £75 / night

(1) Very Good 

1 / 20

Kissimmee Lake Front Villa - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 105 km; Swimming pool;
Get your vacation started 15 minutes after leaving the airport when you stay in your private Regal Villa, an oasis of relaxation and fun. It's only 20 minutes straight down Osceola Parkway to Disney's gate, the same area as Universal Studios and Sea World. Jus  …see more

from £107 / night

£0 / week

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from £107 / night

(1) Excellent 

1 / 10

Lake View - Compass Bay townhouse sleeps 9

Kissimmee / Compass Bay

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 101 km; Swimming pool;
Location is important and Compass Bay is one of the best, it is situated on the corridor of the 192 which has restaurants, shops and attractions. It is within minutes of the major attractions of Disney, Universal and International Drive. It is a gated community with a l  …see more

from £70 / night

£495 - £580 / week

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from £70 / night

1 / 32

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £61 / night

£423 - £530 / week

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from £61 / night

(4) Excellent 

1 / 16

Sunrose Villa, 4 Bedroom Home with WiFi and Pool

Kissimmee / Eagle Pointe

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
When on holiday if you what to retain a bit of independence then a stay in your very own Villa is a perfect way to do it. Our Disney area villa comes with its very own private swimming pool where you can escape all the thrills and spills down the road and have some quie  …see more

from £84 / night

£581 - £642 / week

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from £84 / night

(25) Excellent 

1 / 77

Chris and Sue's Disney Condo - Windsor Palms condo sleeps 7

Kissimmee / Windsor Palms

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Nearest beach 117 km; Swimming pool; Great for children of all ages ;
FREE PHONE CALLS AND WIFILuxurious 3 bedroom/2 bathroom, fully equipped Condo is located in the exclusive gated community of Windsor Palms, Kissimmee, less than 3 miles from Walt Disney World. A perfect location for all that Central Florida has to offer eg The Parks of  …see more

from £63 / night

£390 - £675 / week

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from £63 / night

(1) Excellent 

1 / 18

Central Florida / Kissimmee

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £126 / night

£0 / week

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from £126 / night

(3) Excellent 

1 / 17

Kissimmee Disney Villa with Wireless Internet

Central Florida / Kissimmee

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Nearest beach 106 km; Swimming pool; Great for children of all ages ;
THE HOUSE IS LOCATED ON INDIAN POINT KISSIMMEE. A RESIDENTIAL AREA COMPRISING OF HOMES WITH PERMANENT AND HOLIDAY RESIDENTS.IT IS LOCATED 2 MILES SOUTH OF HIGHWAY 192 OFF POINCIANA BLVD.IT IS ALSO ACCESSIBLE FROM NORTH BASS ROAD WHICH ALSO LEADS OFF HIGHWAY 192. THIS DE  …see more

from £65 / night

£450 / week

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from £65 / night

(2) Excellent 

1 / 24

Lakeside Luxury - Crescent Lakes house sleeps 8

Kissimmee / Crescent Lakes

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Luxury 4 bedroom detached family home with pool occupying a very large, private plot on a quiet culdesac offering lots of indoor and outdoor space. The property is situated on a retention lake, the large garden and lakeside position providing privacy on all sides for th  …see more

from £85 / night

£760 - £900 / week

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from £85 / night

(3) Very Good 

1 / 23

Lindfield Villa - Lindfields villa sleeps 10

Kissimmee / Lindfields

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
This 4 bed 2 and a half bath pool home is located in Lindfields a well- established vacation home community. It is sought after for its proximity to Disney and the shops and restaurants of 192.This spacious home is located on a corner lot and has a good sized south west  …see more

from £87 / night

£609 - £735 / week

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from £87 / night

(25) Excellent 

1 / 90

Luxury Florida Villa in Kissimmee - Eagle Pointe villa sleeps 6

Kissimmee / Eagle Pointe

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
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 £65 / night

£455 - £553 / week

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from £65 / night

(4) Very Good 

1 / 74

New Orlando Villas 1 - Kissimmee villa sleeps 12

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
Our Home is a Modern single 4 home with plenty of space for upto 12 Guests, Its in a Quiet location yet very close to all major Shops like Walmart, Target, K Mart and several Shopping Malls also Restaurants and Fast Food outlets and all the areas Theme Parks.Fully Fitte  …see more

from £120 / night

£836 - £1065 / week

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from £120 / night

1 / 28

Condo at Legacy Dunes - resort amenities

Kissimmee / Legacy Dunes Resort

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 150 km; Swimming pool;
Newly refurbished 4 bedroom/2 bathroom 1400 sq ft condo with screened balcony and view over the lawn to the children's playground and lake. Fantastic place for a large family or group vacation in Orlando! near all the attractions. Would suit the extended family with 2 d  …see more

from £60 / night

£400 - £600 / week

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from £60 / night

(8) Excellent 

1 / 23

Palm Tree Villa Florida, 5 Star Review Rating.

Kissimmee / Doral Woods

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £100 / night

£695 - £875 / week

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from £100 / night

1 / 51

Sun Lake 3 BR Near Disney inc. WIFI,Cable,Parking

Central Florida / Kissimmee

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; 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 £58 / night

£378 - £455 / week

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from £58 / night

(22) Excellent 

1 / 62

Otters Lake, huge pool,only 10 mins Disney & shops

Kissimmee / Lindfields

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
This villa has a fantastic large pool with jacuzzi hot tub backing on to a lovely lake and forest. The pool is not overlooked so you will not find excited children spoiling your peaceful evenings ! The location could not be better - just ten minutes to Disney - cl  …see more

from £70 / night

£475 - £625 / week

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from £70 / night

(1) Very Good 

1 / 20

Lovely Harmony Haven has a Gameroom, WiFi, and Air Conditioning

Kissimmee / Windsor Hills Resort

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 100 km; Swimming pool;
Harmony Haven is an executive vacation home that has 4 bedrooms, 4 bathrooms, games room, fully screened in swimming pool, spa, and lanai. This fully air-conditioned vacation home is located less than 2 miles from Disney in Windsor Hills, a resort-style community.With  …see more

from £96 / night

£802 / week

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from £96 / night

(15) Excellent 

1 / 48

Beautiful Kissimmee Townhome at Fiesta Key - WIFI

Central Florida / Kissimmee

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 104 km; Swimming pool; Great for children of all ages ;
Our Orlando Vacation Home, 'CABALLERO' is a beautiful Spanish influenced fully equipped home in the exclusive Fiesta Key Resort - ideally situated within easy reach of all the major Orlando theme parks, attractions, shops and restaurants. Just 20 minutes drive to Disney  …see more

from £44 / night

£0 / week

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from £44 / night

(5) Excellent 

1 / 43

Florida Lets A Dream - Winward Cay villa sleeps 8

Kissimmee / Winward Cay

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Windward Cay, Kissimmee, Orlando, FloridaA superior, well appointed detached 3 bedroom villa, The accommodation comprises of a spacious lounge/dining room with 2x queen size sofa bed, additional family room and patio doors leading to the pool deck - perfect for al-fresc  …see more

from £66 / night

£460 - £640 / week

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from £66 / night

1 / 42

Enjoy the Hot Tub while the Kids Play in the Pool!

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
Magical Home in the Perfect Location You'll LOVE! Serendipity at Indian Creek offers you all those extra finishing touches that turn an ordinary home into your very own piece of vacation paradise. ** Totally Private Pool & Hot Tub ** Outdoor Poolside Living Space with  …see more

from £294 / night

£1924 - £2726 / week

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from £294 / night

(8) Very Good 

1 / 10

Florida Holiday Villa includes WiFi and Hot Tub

Central Florida / Kissimmee

4 bedroomsSleeps 94 nights min stay

  • 4 bedrooms
  • Sleeps 9
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Our villa is situated in the popular community of Indian Point, which is about 15 minutes drive from Disney and close to the other vast array of attractions that Florida has to offer. It is the perfect place to relax by the pool, or come back to after a day at the theme  …see more

from £65 / night

£450 / week

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from £65 / night

1 / 55

Beautifully furnished condo 10 minutes from Disney

Kissimmee / Cane Island

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
This ground floor apartment is first class. Compare staying here with staying in a Disney Hotel and you will be astonished. Half the price of a 'moderate' Disney Resort but twice as much space as a 'Deluxe' Resort. Not only will you be saving mone  …see more

from £49 / night

£0 / week

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from £49 / night

(4) Very Good 

1 / 88

Sunny Seasons Vacation Rental with Wireless Internet

Kissimmee / Seasons Resort

5 bedroomsSleeps 104 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Our Villa is an Executive Luxury 5 bedroom villa sitated on the ever popular Seasons Estate in Kissimmee. Central for all that the fabulous state of Florida has to offer and within ten minutes drive of the Magical experience that is Disney World, Orlando. USA.Packed wit  …see more

from £95 / night

£625 - £840 / week

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from £95 / night

(9) Very Good 

1 / 90

Palm Heaven Villa, Relaxing Family Getaway in Kissimmee

Kissimmee / Terra Verde Resort

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 90 km; Swimming pool; Great for children of all ages ;
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 £65 / night

£400 - £495 / week

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from £65 / night

(4) Excellent 

1 / 17

Amarillo Villa boasts hot tub and private pool

Kissimmee / Windsor Hills Resort

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Nearest beach 110 km; Swimming pool; Great for children of all ages ;
Our villa accommodates 8 people, and is equipped with everything needed to make your stay enjoyable. There are four bedrooms complete with full baths: two king-sized master suites, a queen and a bedroom with twin beds. The chair in the nook makes into a twin, too. Each  …see more

from £123 / night

£855 / week

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from £123 / night

1 / 13

Amazing Condo with a Pool and Jacuzzi at Venetian Bay Resort

Kissimmee / Venetian Bay Villages

4 bedroomsSleeps 103 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
4 Bedrooms, 3 bathrooms, sleeps 10Venetian 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 Florid  …see more

from £80 / night

£500 / week

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from £80 / night

(3) Excellent 

1 / 42

Executive 2 Story Villa in Kissimmee Gated Community

Kissimmee / Cumbrian Lakes

5 bedroomsSleeps 114 nights min stay

  • 5 bedrooms
  • Sleeps 11
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
HUGE ! five star accredited villa near Disney , If you require something a little bit special for that once in a lifetime Florida vacation our home is the one for you !! Enquire early for further details about the standard of accommodation and five star facilities  …see more

from £140 / night

£0 / week

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from £140 / night

1 / 33

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £91 / night

£636 - £904 / week

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from £91 / night

1 / 28

The Marriott Retreat - Emerald Isle Kissimmee villa sleeps 10

Kissimmee / Emerald Isle Kissimmee

5 bedroomsSleeps 107 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
Emerald Island Resort is surrounded by a conservation area and encompasses over 300 acres with 11 heavily wooded acres right in the middle of the community. As you pass through the 24 hour guarded gatehouse the playful dolphin fountains welcome you to this unique resort  …see more

from £172 / night

£1200 - £1350 / week

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from £172 / night

(1) Excellent 

1 / 17

5 Bed, 3 Bath,Pool, Spa,Games - Kissimmee villa sleeps 12

Central Florida / Kissimmee

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
This spacious, five bedroom, three bath, luxury villa with optionally heated private Pool Spa and Games Room with Pool Table, Air Hockey Table and Football Table, is situated on the exclusive EMERALD ISLAND RESORT (The nearest to Disney). It is located just three miles  …see more

from £115 / night

£700 - £1120 / week

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from £115 / night

1 / 11

Fw2020mgm - Compass Bay apartment sleeps 4

Kissimmee / Compass Bay

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Cozy 2 Bed, 2 Bath Condo!This cute little condo is tucked away at the newly renovated Fantasy World. Ready to be your next vacation condo. Centrally located near the Disney Parks, local dinning, shopping, & entertainment. This 2 bedroom 2 bath condo offers guests th  …see more

from £68 / night

£476 - £594 / week

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from £68 / night

(14) Excellent 

1 / 29

Disney Family Villa - South Facing Pool & Spa

Kissimmee / Seasons Resort

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 110 km; 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 £99 / night

£565 - £725 / week

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from £99 / night

(4) Very Good 

1 / 56

DisneyDream Orlando Florida - Kissimmee apartment sleeps 6

Central Florida / Kissimmee

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car advised;
This is your luxury 3 bedroom 2 bathroom holiday home located in ' the 'VILLAS OF SOMERSET' complex, a quiet leafy location very central to every theme park in the Orlando area. Use all the facilities on the complex, Heated pool, Jacuzzi/hot tub, Sundeck,Clubhouse, G  …see more

from £49 / night

£343 - £549 / week

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from £49 / night

1 / 28

Stunning 5 Bed 4 Bath Villa on 5 Star Bella Vida

Central Florida / Kissimmee

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
A stunning, larger than average, 5 Bed 4 Bathroom villa with a beautiful view of the conservation area at the rear as background of our private pool. All rooms in the villa are spacious. The villa is furnished and maintained to a very high standard. The villa is located  …see more

from £104 / night

£684 - £989 / week

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from £104 / night

(8) Excellent 

1 / 14

Alberto Circle, Fun Vacation House with Pool

Kissimmee / Bellavida Resort

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 100 km; Swimming pool; Great for children of all ages ;
Enjoy the fabulous climate and amenities of the Central Florida area without breaking the bank. This is a 3 bedroom townhouse, fully air conditioned, with private pool, conveniently located in the recently completed BellaVida resort in Kissimmee.The property is ideally  …see more

Pricing unknown

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1 / 30

Stunning townhouse, discounts for 2016 bookings

Central Florida / Kissimmee

4 bedroomsSleeps 103 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
Fabulous location for everything the area has to offer. Only 10 minutes from Disney main gates & 20 mins to Universal. Convenient for shops, restaurants and outlets Complex offers heated pool, tennis, basketball, play area, splash pad, volley ball, & other amenities al  …see more

from £69 / night

£449 - £589 / week

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from £69 / night

1 / 31

Central Florida / Kissimmee

7 bedroomsSleeps 142 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £168 / night

£0 / week

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from £168 / night

(10) Excellent 

1 / 20

Villa di Lusso - Bellavida Resort villa sleeps 14

Kissimmee / Bellavida Resort

6 bedroomsSleeps 141 night min stay

  • 6 bedrooms
  • Sleeps 14
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
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 £160 / night

£1087 / week

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from £160 / night

(2) Very Good 

1 / 20

Legacy Dunes Resort - Legacy Dunes Resort condo sleeps 4

Kissimmee / Legacy Dunes Resort

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
This Condo is on the doorstep of Disney, just off 192, In the heart of Kissimmee. From the moment you drive up the entrance road, with its beautiful landscaping, you know you are about to enter a great resort. Legacy Dunes Resort offers a wonderful guest experience. The  …see more

from £65 / night

£455 - £490 / week

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from £65 / night

(1) Excellent 

1 / 41

TERRA VERDE TOWNHOUSE 3BR / 2.5 BATH - Kissimmee townhouse sleeps 6

Central Florida / Kissimmee

3 bedroomsSleeps 65 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min stay
Key info: Nearest beach 114 km; Swimming pool; Great for children of all ages ;
This is a luxurious stunning spacious modern 3 bedroom, 2.5 Bathroom Townhouse two-storey. As you enter the home you are greeted by light, bright and airy open feel of the home is the perfect base for a relaxing, stress free vacation, situated by a 3-acre lake view from  …see more

from £75 / night

£525 / week

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from £75 / night

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