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

Filters applied: Swimming pool (535)

32 of 535 Results

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from £99 / night

£690 - £895 / week

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(14) Excellent 5/5 

1 / 24

Holiday villa with private swimming pool in Kissimmee

Kissimmee / Doral Woods

Villa / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £99 / night

£690 - £895 / week

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*Doral Woods* Gorgeous 4Bed, 2.5 Bath Villa with a VERY big private rear south facing garden + fruit trees + its own heated pool that's not overlooked + Hot tub, Gas BBQ + Free WiFi. Cable TV, Close to the theme parks, this beautiful spacious villa won't disappoint you! *One of Holiday Lettings top 10 Hot listed properties.  …see more

from £64 / night

£446 - £566 / week

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(7) Excellent 5/5 

1 / 15

Bungalow rental in Kissimmee

Kissimmee / Eagle Pointe

Bungalow / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

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from £64 / night

£446 - £566 / week

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An open plan living area and vaulted ceilings, give the villa a spacious feel. It also allows you to have a great view of the pool and deck area. It has a family area around the huge 55-inch cinema style TV and close to the fully fitted, dine in kitchen. A large heatable pool fully screened and south facing with Luxury poolside furniture all towels are provided  …see more

from £65 / night

£450 - £600 / week

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(1) Excellent 5/5 

1 / 4

Kissimmee holiday villa rental

Kissimmee / Country Creek

Villa / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

Excellent 5/5 

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from £65 / night

£450 - £600 / week

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Country Creek Estates is an established, quiet, well laid out residential community, just a few mins away from Hwy 192 where you will find a 24hour Walmart as well as a large range of restaurants and other shops. Within a few minutes drive there are many other superma  …see more

Featured properties

from £75 / night

£525 - £665 / week

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(1) Very Good 4/5 

1 / 20

Holiday villa letting

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Very Good 4/5 

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from £75 / night

£525 - £665 / week

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Privately owned (since 2003) spacious and luxurious fully air conditioned family villa.. Sleeps up to 8 adults + 1 infant. Ideal for 2 families. 4 bedrooms and 3 bathrooms including 2 master suites with king and queen sized beds and 2 twin bedrooms. Fully furnished and extensively equipped. Flat screen TV's with DVD players in living room and all bedrooms.  …see more

from £162 / night

£1130 - £2000 / week

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(3) Excellent 5/5 

1 / 27

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

Villa / 6 Bedrooms / sleeps 14

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

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from £162 / night

£1130 - £2000 / week

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3 Miles from Disney in Emerald Island resort ~ Air-conditioned game room with pool table, air hockey, foosball and large screen TV ~ 6 bedrooms, 5.5 bathrooms ~ 4 Master suites with King size beds ~ 2 themed kids rooms ~ Large south-facing pool and spa NOTE: We prefer Sat-Sat bookings. All variations are considered by owner, so please ask.  …see more

from £65 / night

£450 - £500 / week

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1 / 19

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

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from £65 / night

£450 - £500 / week

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This villa is ideal for families with small children. Very kiddy orientated  …see more

from £78 / night

£545 - £660 / week

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(1) Excellent 5/5 

1 / 20

Villa rental in Kissimmee

Kissimmee / Indian Ridge

Villa / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning

Excellent 5/5 

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from £78 / night

£545 - £660 / week

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3 bedroom/2 bath spacious villa, West Kissimmee, countryside estate Indian Ridge 3 miles south of Disney South facing solar/gas heated pool Private secluded fenced garden Family room and living room 5 HDTVs, 70+ dvds 24/7 security system Security safe Child equipment 3 miles to Disney - south facing solar heated pool - 3 bedroom/2 bathroom Key are located at the property  …see more

from £90 / night

£630 - £835 / week

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(2) Very Good 4.5/5 

1 / 21

Holiday villa with swimming pool in Emerald Isle Kissimmee

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Very Good 4.5/5 

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from £90 / night

£630 - £835 / week

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Florida Jewels - 4 bed 3 bath Luxury Villa on Emerald Island, Games room with pool table Arcade game darts and more, extended south west facing pool with spa, free local national and international landline calls.  …see more

from £58 / night

£400 - £550 / week

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(3) Excellent 5/5 

1 / 23

Holiday home rental

Kissimmee / Crescent Lakes

House / 5 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £58 / night

£400 - £550 / week

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Large well appointed fully equiped Orlando house/villa with large screen covered south facing heated pool with spa. Five bedrooms (two ensuite). Games room. Disney area. Private garden spectacular views over lake to rear. parking. Vaulted ceiling great room Fully equipped laundry and kitchen, central air con and heating. Smoke alarms outside gas grill  …see more

from £50 / night

£350 - £550 / week

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(11) Excellent 5/5 

1 / 22

Holiday townhouse in Kissimmee

Kissimmee / Encantada Resort

Townhouse / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £50 / night

£350 - £550 / week

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A 3 Bedroom Luxury home, set in a gated resort just 5 miles from Disney. Enjoy the private, screened and heated splashpool, Now with Brand new Granite worktops in the Kitchen and bathrooms, new wooden flooring in the bedrooms, Air conditioned throughout Facilities on site all within a minutes walk, choose from Pool, Gym, fishing lake, or play area for children  …see more

from £122 / night

£850 - £1200 / week

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(9) Excellent 5/5 

1 / 24

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

House / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £122 / night

£850 - £1200 / week

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This beautifully furnished, air-conditioned executive home is at Emerald Island Resort, the nearest gated community to Disney. With 6 bedrooms, all with TVs, 4 masters with en suites, and 5.5 bathrooms will sleep up to 12 people in spacious, elegantly furnished style. Close to shops and many restaurants  …see more

from £68 / night

£470 - £823 / week

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(2) Excellent 5/5 

1 / 24

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

House / 4 Bedrooms / sleeps 8

  • Nearest beach 96 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £68 / night

£470 - £823 / week

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COMFORTABLE 4 BED/ 3 BATH HOUSE WITH HEATED POOL AND SPA, GAMES ROOM WITH AIRHOCKEY E GAMES ARCADE, 3 MILES TO PARKS, FREE WI-FI, CABLE TV AND A FULL RESORT WITH SWIMMING POOL, TIKI BAR, FITNESS ROOM, COMPUTERS WITH WI-FI, TENNIS COURT, TRAILS AND BEAUTIFUL GARDENS. PAY LESS THAN A HOTEL AND HAVE MORE COMFORT AND PRIVACE WITH A BIG HOUSE, RENEWED IN NOV. WITH WOODEN FLOOR.  …see more

from £78 / night

£540 / week

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(1) Excellent 5/5 

1 / 11

Holiday villa with golf nearby in Kissimmee

Central Florida / Kissimmee

Villa / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £78 / night

£540 / week

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* Private Heatable south facing pool with extended pool deck. * Location: Kissimmee Florida * Ideally situated less than 1 mile from Hwy 192, in East kissimee * Computer to access the internet. *WiFi for your laptops and Ipods etc. * Easy access to Walt Disney W Pool heat is £10/day if required A car is required, public transport is very poor  …see more

from £57 / night

£395 - £840 / week

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1 / 30

Kissimmee holiday villa let

Kissimmee / Lindfields

Villa / 3 Bedrooms / sleeps 6

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

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from £57 / night

£395 - £840 / week

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A Real Home in the Right location - Lindfields is an ideal base for your vacation. This popular development is peaceful but well located at 192 west, very close to Disney. Our larger pool is fenced for total privacy, is solar heated and we have a heater option. We love our home and try to ensure our guests love it as much as we do!  …see more

from £88 / night

£610 - £750 / week

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(4) Excellent 5/5 

1 / 20

Kissimmee holiday villa rental

Kissimmee / Crescent Lakes

Villa / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £88 / night

£610 - £750 / week

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Price All inclusive of tax 4 bedrooms, 2.5 bathrooms sleeps 8 2760 sq ft Lge Private pool, new spa, extended deck area & lake view Close to Disney Parks, Universal, Sea-World etc, Golf, Horse riding, Fishing, Shops & Restaurants 2 Lg Lanai Games Room Gas BBQ Pool heating is an additional £75.00 per week. Spa heating is an addiitional £35.0.00 per week  …see more

from £69 / night

£480 - £570 / week

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(6) Excellent 5/5 

1 / 24

Villa rental in Kissimmee with shared pool

Central Florida / Kissimmee

Villa / 4 Bedrooms / sleeps 10

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £69 / night

£480 - £570 / week

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Our luxury 4 BED, 3 BATH villa, is fully furnished & equipped to the highest standard, featuring a private pool & games room, free secured WIFI & fully air conditioned. Disney, SeaWorld & Universal are just a short drive away with US192 shopping & entertainment nearby. With 2 master suites, "Magical Vacations" is ideal for families of all sizes, or even two families sharing.  …see more

from £63 / night

£440 - £690 / week

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(3) Excellent 5/5 

1 / 12

Kissimmee holiday villa rental

Central Florida / Kissimmee

Villa / 3 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

Excellent 5/5 

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from £63 / night

£440 - £690 / week

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South Facing Pool that cannot be overlooked from any direction, Free wi-fi, Games room, Free International calls, 3 TV's including 50'' plasma TV, Smart TV with Free Netflix, Walking Distance to Shops, Restaurants, Attractions and nature park.  …see more

from £70 / night

£490 - £610 / week

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(1) Very Good 4/5 

1 / 6

Holiday villa rental

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Very Good 4/5 

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from £70 / night

£490 - £610 / week

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This luxurious 4 bed/3 bath villa is located on the prestigious Emerald Island Resort just 5 minutes from Disney and 2 mins from shops and restaurants. We are 30 mins drive from Orlando International Airport and under 1 hour from Sanford Airport.  …see more

from £50 / night

£350 - £550 / week

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(7) Very Good 4.5/5 

1 / 17

Holiday villa in Seasons Resort

Kissimmee / Seasons Resort

Villa / 5 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

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from £50 / night

£350 - £550 / week

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A luxurious 5 Bedroom - 4 Bathroom home, with 2 Master Suites, Private Pool with Jacuzzi, plus games room in the small community of only 71 houses only 10 minutes away from Disney. Priced very reasonable.  …see more

from £40 / night

£275 - £295 / week

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(9) Excellent 5/5 

1 / 20

Holiday bungalow with shared pool in Vista del lago

Kissimmee / Vista del lago

Bungalow / 3 Bedrooms / sleeps 7

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £40 / night

£275 - £295 / week

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Beautiful bungalow near Disney, three bedrooms, two bathrooms.,  …see more

from £244 / night

£1707 - £2090 / week

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(52) Excellent 5/5 

1 / 20

Holiday villa with golf nearby in Kissimmee

Kissimmee / Formosa Gardens

Villa / 7 Bedrooms / sleeps 19

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

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from £244 / night

£1707 - £2090 / week

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" This really is the classiest of them all " Winner of the Best Kissimmee Vacation Rental Home 2011 & 2012, and Rated Excellent, and Recommended by Trip Advisor. Exceptionally luxurious 7 bed, 6 baths, sleeps 16, South Facing, Lake View, Formosa Gardens Villa. Florida Vacation Home,10 minutes from Disney,take a look at the outstanding features this Holiday Home has.  …see more

from £110 / night

£770 - £1260 / week

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(5) Excellent 5/5 

1 / 21

Trafalgar Village holiday home rental

Kissimmee / Trafalgar Village

House / 5 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

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from £110 / night

£770 - £1260 / week

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Lake view* Pool & Spa* Free internet* Our wonderfully spacious 5 bedroom home is set in the most beautiful and peaceful reserve area and gated community, only minutes from Disney and all major theme parks. One of the best homes in the area. After long days at the theme parks “Lake View” is the perfect home for you and your family to relax.  …see more

from £67 / night

£467 - £834 / week

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(6) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £67 / night

£467 - £834 / week

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Gated Resort Villa in Emerald Isle Resort. Newly refurbished Living area Private Pool Resort Gym/Sauna/Steam room Close to Disney FREE long distance to calls anywhere in the US & Canada. WiFi  …see more

from £124 / night

£864 - £1120 / week

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1 / 15

Kissimmee holiday villa accommodation

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages

Add to shortlist

from £124 / night

£864 - £1120 / week

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Minutes from Disney, emerald island resort, 4 bed, not overlooked, private heated pool & spa, 3 bath, games area, free broadband, resort facilities.  …see more

from £79 / night

£550 - £700 / week

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(18) Excellent 5/5 

1 / 23

Holiday home with swimming pool in Oak Island Cove

Kissimmee / Oak Island Cove

House / 5 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £79 / night

£550 - £700 / week

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This villa cater'd for everything we needed a large pool ,hot tub and very close to all the theme parks (only 2.8 miles from blizzard beach) and very close to many different restaurants and shops yet in a nice quiet area to relax in away from all the hustle and bustle. For a truly memorable stay look no further than our beautiful Family friendly home!  …see more

from £93 / night

£645 / week

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(2) Excellent 5/5 

1 / 24

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

Villa / 4 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £93 / night

£645 / week

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A wonderful villa, very close to Disney, overlooking beautiful lake, private heated swimming pool, Restaurants and shops close by. Fully air conditioned, 4 large bedrooms, premium cable TV, games console, everything you could want in your home from home.  …see more

from £100 / night

£695 - £895 / week

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(28) Excellent 5/5 

1 / 24

Holiday villa in Kissimmee

Kissimmee / Doral Woods

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

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from £100 / night

£695 - £895 / week

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Our villa's are on a quiet sub-division ,we have a one acre garden fully fenced and private with a play area and large decking .Our pool is 28 X 14 .Our homes are family owned and finished to a high standard our guests enjoy.We upgrade each visit ,prices are kept low Both villas are private , guests return knowing they have found their perfect villa ,visit our website  …see more

from £79 / night

£550 - £750 / week

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(1) Excellent 5/5 

1 / 16

Holiday villa in Lake Berkley

Kissimmee / Lake Berkley

Villa / 4 Bedrooms / sleeps 8

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £79 / night

£550 - £750 / week

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Luxury Lakeside Villa with own pool/spa. 10 mins to Disney. Free high speed internet access. 37" wide screen TV. Free high speed internet access. TVs in every bedroom. Fully air conditioned. Pay by credit card or cheque. The villa is situated within Lake Berkley Resort, Kissimmee, a safe, secure gated community.  …see more

from £69 / night

£480 - £495 / week

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(17) Excellent 5/5 

1 / 23

Villa rental in Kissimmee

Central Florida / Kissimmee

Villa / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

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from £69 / night

£480 - £495 / week

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WOW LOOK! This fully air-conditioned (non-smoking) villa is sumptuously decorated to a very high specification with exclusive quality furnishings. The villa sleeps 6-8 people is ceramic tiled throughout with a beautiful pool. Luxury, minutes from Disney and free WiFi We charge the same great rate all through the year regardless of the season. Over 3 weeks special rates.  …see more

from £170 / night

£1190 - £2100 / week

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(2) Excellent 5/5 

1 / 20

Kissimmee holiday home let

Kissimmee / Emerald Isle Kissimmee

House / 7 Bedrooms / sleeps 16

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

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from £170 / night

£1190 - £2100 / week

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Theater room, lake view, South facing pool & spa, pool table, free internet, free local calls. Our luxurious 5star, 7 bedroom home has it all. Professionally decorated to a very high standard,the perfect vacation home. One of the best. 2 luxury master suites, 2 designer Queen bedrooms, 3 kids rooms, Toy Story, Disney Princess & Mickey Mouse .  …see more

from £80 / night

£560 - £910 / week

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(1) Excellent 5/5 

1 / 59

Holiday home in Kissimmee

Kissimmee / Paradise Palms

House / 4 Bedrooms / sleeps 12

  • Nearest beach 103 km
  • Swimming pool
  • Not suitable for children
  • Car advised

Excellent 5/5 

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from £80 / night

£560 - £910 / week

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A casa fica no Condomínio Paradise Palms, o condomínio preferido dos Brasileiros em Orlando! Alugue na Disney!!!  …see more

from £70 / night

£484 - £1097 / week

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1 / 24

Holiday home with shared pool in Paradise Palms

Kissimmee / Paradise Palms

House / 5 Bedrooms / sleeps 11

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

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from £70 / night

£484 - £1097 / week

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In front a clubhouse with lake view. BBQ free This beautiful unit is located in Paradise Palms Resort one of Florida's Premier Resorts only 5 minutes from Disney!! With 5 deb/4ba ( 2 king suits, 1 queen, 1 full, 3 twins and 1 portable crib). BBQ free and in front a clubhouse with lake view.  …see more

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