Kissimmee apartment or villa with a heated pool

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Kissimmee

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1,301 Holiday homes

Filters applied: Heated pool (1,303)

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

(2) Very Good 

18

Holiday 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 km
  • Swimming pool
“Perfect family spot.” At the time of our check in our wonderful vacation began. The villa was classically appointed. Everything was spotless and functional. The lush landscape was a fitting tropical backdrop for the winding river. All common a  …see more

from £171 / night

£1200 / week

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from £171 / night

(4) Excellent 

23

Holiday villa in Windsor Hills Resort

Kissimmee / Windsor Hills Resort

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Spacious House” The house was great very spacious and all 12 of us enjoyed it very much. The downside of getting to a property after being delayed for over 2 hours was it was late at night and other properties we had rented before left us a welcome  …see more

from £163 / night

£1139 / week

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from £163 / night

23

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
Emerald Island Resort offers many community features and stands above the rest in offering luxurious villas. Why stay anywhere else when you can rent this luxury villa within 5 minutes (3 miles) of Disney World Orlando Florida? Deal with us, the owners direct and save  …see more

from £196 / night

£1220 - £1870 / week

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from £196 / night

Featured properties

(1) Excellent 

20

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

6 14 1 night min

  • 6 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
You don't need a magic wand or a secret potion to have a dream holiday of a life time . . . . . . All you need is Magic Villa!!!And as Magic Villa is only 10 minutes' drive from Disney the location is magic too!  …see more

from £172 / night

£1204 / week

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from £172 / night

22

Kissimmee holiday villa let

Kissimmee / Lake Berkley

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
to do  …see more

from £90 / night

£630 / week

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from £90 / night

99

Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
THE VILLA FOR A LUXURY HOLIDAY! South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

from £150 / night

£1050 / week

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from £150 / night

17

Kissimmee holiday home rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a luxurious 3 bedroom 3 bathroom villa with private pool with conservation view on 5 Star Eagle Pointe Resort, Kissimmee, Orlando. The villa was recently refurbished and now benefits from ceramic tile and wood flooring throughout. The villa is furnished to a v  …see more

from £90 / night

£610 - £728 / week

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from £90 / night

(4) Excellent 

98

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 96 km
  • Swimming pool
  • Child friendly
“Emerald Isle Excellence” We stayed here at the end of our 2 week Florida road trip for 5 nights, 24 -29 Oct. Wished we could have stayed longer.Upon arrival at front gate the security were polite and helpful took details of our car and directed us to  …see more

from £82 / night

£570 - £848 / week

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from £82 / night

(3) Very Good 

43

Holiday villa rental

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 £78 / night

£546 / week

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from £78 / night

(3) Excellent 

24

Holiday home in Crescent Lakes

Kissimmee / Crescent Lakes

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Large Deck and Lanaii ,private pool not overlooked .Tiled floors all rooms except Family room  …see more

from £90 / night

£580 - £748 / week

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from £90 / night

(3) Excellent 

60

Cumbrian Lakes holiday villa rental

Kissimmee / Cumbrian Lakes

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
A Spacious 6 bedroom, 4 1/2 bathroom Vacation Home with private pool for your enjoyment. In the popular gated community of Cumbrian Lakes, only 15 minutes to the entrance to Disney World, 5 minutes more to Seaworld & another 10 minutes to Universal Studios. This hom  …see more

from £75 / night

£525 / week

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from £75 / night

(29) Very Good 

20

Kissimmee holiday villa accommodation

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Very peaceful area to vacation.” Very nice home with all the amenities needed for your vacation. Close to all Disney adventures and alot to do nearby in Kissimmee. Lots of shopping near home too. Very clean home. Would not think twice about rentin  …see more

from £105 / night

£732 / week

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from £105 / night

(2) Very Good 

12

Holiday villa rental

Central Florida / Kissimmee

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Great rates & great location. A beautiful property in Kissimmee, Florida, our self catering holiday home offers so much more than just an ordinary holiday home, in one of the best locations in the Orlando area. A home from home, with everything to ensure a truly wo  …see more

from £72 / night

£450 / week

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from £72 / night

(2) Very Good 

24

Kissimmee holiday home rental

Central Florida / Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury tropical five star resort and house. Close to Disney parks and within range of Florida's west coast beaches.  …see more

from £99 / night

£693 - £910 / week

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from £99 / night

(2) Excellent 

12

Holiday villa in Windsor Palms

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 5 km
  • Swimming pool
  • Child friendly
Disney World ( 10 minutes ) - Special Pool Heater - Salt Water Pool - Safety Fence - 2 en-suite master king-bedrooms - Themed bedrooms - High chair , Stroller , Car seats , Crib Fan cooled Lanai - Close to Clubhouse - Gameroom - BBQ - Multi Color Pool Light  …see more

from £139 / night

£968 / week

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from £139 / night

(6) Excellent 

43

Holiday townhouse in Kissimmee

Central Florida / Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 114 km
  • Swimming pool
  • Child friendly
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

(6) Excellent 

16

Holiday villa with swimming pool in Kissimmee

Kissimmee / Eagle Pointe

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Soon You'll Be Staying at a Individually Designed Luxury 4 Bed villa with all of the home comforts you expect.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 family time  …see more

from £82 / night

£553 - £1053 / week

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from £82 / night

17

Holiday villa with shared pool, golf nearby in Kissimmee

Kissimmee / Orange Lake Resort

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Family Fun in the Heart of Orlando, Florida. Shop, dine, play, golf—we've got everything you need for the vacation of a lifetime. And right next door to Walt Disney World® Resort and Animal Kingdom! Luxuriously decorated villas for your comfort.<br /&g  …see more

from £171 / night

£950 / week

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from £171 / night

(1) Very Good 

39

Villa rental in Kissimmee with swimming pool

Central Florida / Kissimmee

6 13 4 nights min

  • 6 bedrooms
  • Sleeps 13
  • 4 nights min
  • Nearest beach 144 km
  • Swimming pool
  • Child friendly
CONFIRM AND BOOK BETWEEN THE 1ST AND 31ST OCTOBER FOR ANY STAY AND RECEIVE A 5% DISCOUNT ON YOUR BOOKING REFURBISHED OCTOBER 2015 TO A VERY HIGH STANDARD - prime location holiday villa situated on the Community of Oak Island Cove just 2 miles to Walt Disney World 6 B  …see more

from £165 / night

£1500 / week

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from £165 / night

26

Home rental in Kissimmee

Central Florida / Kissimmee

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We have owned this villa for 8 years and we maintain it to high standards. The Pool Decking has been extended which gives greater poolside space together with longer sunshine hours on the deck.The villa is ideally situated for all the attractions and is close to Walmart  …see more

from £100 / night

£700 - £896 / week

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from £100 / night

(2) Very Good 

14

Villa rental in Kissimmee

Kissimmee / Bellavida Resort

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in the beautiful Bellavida Resort with own South West Facing Pool. Close to all attractions including Disney World, Universal Studios and Islands of Adventure. Dining and Shops are in abundance.  …see more

from £110 / night

£761 / week

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from £110 / night

(6) Very Good 

17

Holiday villa in Kissimmee

Central Florida / Kissimmee

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 106 km
  • Swimming pool
  • Child friendly
“Lovely Villa, well placed” Villa was clean & spacious. Pool was lovely & clean with nice garden view. Mostly quiet neighbourhood. Very close to 192 with all the restaurants & shopping. Ian was easy to contact & kept in touch throughout the stay. Pool  …see more

from £65 / night

£450 / week

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from £65 / night

(1) Excellent 

13

Holiday villa in Kissimmee

Kissimmee / Kissimmee City

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Amazing stay, great villa” Had a lovely stay for 2 weeks. Very easy to book and a lot of useful information emailed before and in the villa as well. Brilliant directions- made it a less daunting experience! Villa very clean with plenty of room and s  …see more

from £81 / night

£507 - £621 / week

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from £81 / night

(1) Excellent 

20

Regal Oaks holiday townhouse rental

Kissimmee / Regal Oaks

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Townhouse near Disney provides comfortable home from home accommodation, together with personal service from the owners to make yours a memorable holiday or vacation in Kissimmee and the surrounding Central Florida area.  …see more

from £82 / night

£570 - £683 / week

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from £82 / night

(7) Very Good 

26

Kissimmee holiday townhouse rental

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our holiday home is at Windsor Palms Resort near Walt Disney World Resort® Florida. Located in Kissimmee, close to Orlando and all the tourist attractions. Free wireless Wifi is available.The holiday home has three bedrooms (king-size, queen & twin, all  …see more

from £95 / night

£615 - £770 / week

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from £95 / night

(2) Average 

30

Holiday villa with swimming pool in Kissimmee

Kissimmee / Emerald Isle Kissimmee

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Family friendly, plenty of room, great location” We stayed here for our very first trip to Disney World with our three teenaged daughters and our young grade-school daughter. We loved the home; it had everything we needed, plenty of space. The three  …see more

from £90 / night

£660 / week

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from £90 / night

37

Kissimmee holiday villa rental

Kissimmee / Lindfields

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This Lindfields Villa is fully air-conditioned giving a cool refreshing welcome when you open the door and is very spacious. This villa is on a quiet road just off highway 192 and only 5.7 miles (10 minute drive) to Walt Disney World. Lovely sunny 30ft private, south f  …see more

from £105 / night

£731 / week

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from £105 / night

(1) Excellent 

8

Holiday home in Kissimmee

Kissimmee / Lake Marion

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Nearest beach 60 km
  • Swimming pool
  • Child friendly
Self-catering condo with communal pool and free WiFi in the property, along with a full set of cable channels<br />Totally Renovated 2 Bed Family Home With Pool & Free Wi-Fi  …see more

from £35 / night

£250 / week

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from £35 / night

(1) Very Good 

20

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
“Lovely villa in a super location” We all thoroughly enjoyed our stay at Harmony Haven with its good standard, spacious accommodation and super swimming pool. We travelled with our children and grandchildren and we all enjoyed the water shoot at th  …see more

from £98 / night

£683 / week

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from £98 / night

(6) Excellent 

24

Holiday home in Kissimmee

Kissimmee / Tuscany, Florida

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Wonderful holiday in a fantastic Villa!” This was our second family holiday to Orlando so we had an idea of what we were looking for from a villa and a location close to the parks. We considered a number of possible options before settling on Luce Del  …see more

from £115 / night

£805 - £980 / week

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from £115 / night

(2) Excellent 

100

Emerald Isle Kissimmee holiday villa rental

Kissimmee / Emerald Isle Kissimmee

7 16 5 nights min

  • 7 bedrooms
  • Sleeps 16
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
LUXURY OF THE HIGHEST QUALITY! Large South facing pool plus spa, games room, BBQ and beautiful lake and woodland conservation views. One of the closest to Disney World!  …see more

from £185 / night

£1295 / week

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from £185 / night

15

Kissimmee holiday home accommodation

Kissimmee / Emerald Isle Kissimmee

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Our Florida home holds so many happy family memories and is very special to us but as we are unable to use it as often we would now like, it is lovely to be able to share it with other families looking to make their own memories. The resort is very well maintained, has  …see more

from £74 / night

£496 / week

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from £74 / night

(3) Very Good 

12

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Crystal Cove Gem is located in the fabulous Emerald Island Resort the nearest gated community to from Disney World.<br />Only 3 miles from Disney World  …see more

from £50 / night

£700 / week

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from £50 / night

(1) Excellent 

55

Kissimmee holiday villa rental

Kissimmee / Lake Berkley

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Loved it so much” Just spent 2 weeks in this villa, loved it so much! Many happy memories of a great holiday, we are definitely looking into coming again. Slept 6 more then comfortably and the pool is in a great position, gets a few hours sunlight bu  …see more

from £90 / night

£550 - £785 / week

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from £90 / night

23

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
6 Bedroom Luxury Villa at Windsor Palms 3 Miles from Disney. Private Pool area with extended decking overlooking beautiful conservation area. 42" flat screen HDTV with cable. Free Wifi Internet. Games room. Gated community. Clubhouse facilities cinema, tennis, gym,  …see more

from £130 / night

£900 - £1150 / week

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from £130 / night

(13) Excellent 

22

Holiday villa with golf nearby in Cumbrian Lakes

Kissimmee / Cumbrian Lakes

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
“The ideal property and location to relax and forget about work” A third visit to this wonderful house which is as fresh and up to date today as our first visit in 2006. The owners I’m sure are very proud of their home and we are grateful to them for a  …see more

from £57 / night

£395 / week

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from £57 / night

14

Villa rental in Kissimmee

Central Florida / Kissimmee

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sparkling lakes provide a hospitable habitat for cranes, ospreys and blue heron. Cumbrian Lakes is a peaceful place to come home after a long day at the parks. Yet is so close to all the excitement that makes Central Florida the Number One Tourist destination in the Wor  …see more

from £80 / night

£490 - £725 / week

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from £80 / night

(2) Excellent 

24

Lindfields holiday home rental

Kissimmee / Lindfields

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our villa is magnificent, fully furnished and equipped to the highest standards with air conditioning and ceiling fans. It has a master bedroom with an en-suite, 3 further double bedrooms and a main bathroom, towels and bed linen are provided. It has a spacious  …see more

from £72 / night

£425 - £500 / week

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from £72 / night

(18) Excellent 

24

Home rental in Bellavida Resort

Kissimmee / Bellavida Resort

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
“East 192, Where Tink@Bella waits for Youuuuuuu” The Bella Vida resort is a Great, Gated Community. Where inside awaits the the Fantastic Tink@Bella Villa. Approx 30 mins from Orlando Int. Perfect location for all that awaits you, Disney, Universal,  …see more

from £143 / night

£995 - £1395 / week

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from £143 / night

30

Holiday villa in Kissimmee

Kissimmee / Terra Verde Resort

6 14 4 nights min

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our luxury 2875 square foot villa is located on the beautiful prestigious community of Terra Verde. This ideal 6 bedroom 5.5 bathroom family home is fully air-conditioned, central heated and sleeps up to 14 people comfortably.  …see more

from £183 / night

£1281 / week

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from £183 / night