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

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3,189 Holiday homes

Filters applied: Swimming pool (3,191)

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

23

Spacious Private Pool/Spa Villa Near Disney - Emerald Isle Kissimmee villa sleeps 17

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Our Spacious 8 bedroom pool/spa villa is located at prestigious Emerald Island Resort, a gated community with 24/7 security guard at gate and only 3 miles away from World Disney. Emerald Island Resort featured with its own clubhouse sauna, fitness center, video games ar  …see more

from £270 / night

£1231 - £2454 / week

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from £270 / night

(1) Very Good 

24

Stunning Family Friendly Villa with Lake Views - Crescent Lakes villa sleeps 14

Kissimmee / Crescent Lakes

6 14 4 nights min

  • 6 bedrooms
  • Sleeps 14
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 123 km
  • Swimming pool
Thank you for taking the time to look at our beautiful villa, we know you will find everything you need to make your stay a perfect one. Crescent Lakes is a stunning, tranquil community and our villa is set right in the heart of it. Disney World is only a short 15 minut  …see more

from £145 / night

£950 - £1230 / week

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from £145 / night

(5) Excellent 

68

Ladysvilla, Lovely Vacation Pool Home in the Sun - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 12 km
  • Swimming pool
  • Child friendly
Ladys Villa (Loz and Ady's villa) is our holiday home in the sun, it will sleep up to 8 people, with games room, private screened pool (heated on guest payment). We invite you to share our home. It is ideally situated for the independent traveller, giving easy access  …see more

from £85 / night

£539 - £893 / week

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from £85 / night

(1) Excellent 

51

Sun Lake 3 BR Near Disney inc. WIFI,Cable,Parking - Kissimmee apartment sleeps 6

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 £58 / night

£381 - £458 / week

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from £58 / night

13

Amazing Condo with a Pool and Jacuzzi at Venetian Bay Resort - Venetian Bay Villages townhouse sleeps 10

Kissimmee / Venetian Bay Villages

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
4 Bedrooms, 3 bathrooms, sleeps 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

(6) Excellent 

18

Blue Sky Villa Luxury villa near Disney - Lake Berkley villa sleeps 8

Kissimmee / Lake Berkley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful villa is located in the prestigious and much sought after resort of Lake Berkley. A gated and guarded 24 hour community with many additional facilities at no extra cost. There is a communal swimming pool and spa, fitness centre, games room, tennis court, b  …see more

from £78 / night

£540 - £600 / week

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from £78 / night

(20) Excellent 

27

Sun Palm - 5 star Disney executive villa. - Windsor Palms villa sleeps 8

Kissimmee / Windsor Palms

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
- The villa has two Master en-suite bedrooms and two further bedrooms with twin beds. These bedrooms share a third bathroom. One of the twin Bedrooms is a Disney themed room. The main bedroom has its own dressing room and has direct access to the pool (via a safety fe  …see more

from £112 / night

£762 - £1154 / week

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from £112 / night

(2) Excellent 

17

Villa Sunshine - Kissimmee villa sleeps 8

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our spacious Villa Sunshine (approx. 2200 sq. ft.) offers our guests immaculate accommodations filled with fine amenities and quality upgrades. Our formal living and dining rooms greet you as you enter our home. You'll enjoy a king sized master en suite and twins them  …see more

from £97 / night

£674 - £924 / week

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from £97 / night

81

6 bed Villa with a View - Kissimmee villa sleeps 14

Central Florida / Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This is a superb secluded villa in the popular gated community of Cumbrian Lakes. The home boasts a magnificent view. The pool is lakefront and overlooks a lush conservation area. This is therefore a wonderful spot to relax in the pool or spa and totally unwind. The hom  …see more

from £120 / night

£840 - £1050 / week

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from £120 / night

(2) Excellent 

61

Great value for money Townhome near Disney - Venetian Bay Villages house sleeps 6

Kissimmee / Venetian Bay Villages

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Why stay in a hotel when you can have all the comforts of your own home away from home in our beautiful new townhome in a dream location, close to the theme parks and the attractions of Orlando and Central Florida.Our home is clean, comfortable and just where you need t  …see more

from £60 / night

£385 / week

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from £60 / night

24

Star Lake View Paradies - Rolling Hills at Formosa villa sleeps 8

Kissimmee / Rolling Hills at Formosa

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The house has four bedrooms, two bathrooms and its own pool. It is located just a few minutes' drive from all of Florida's attractions: Disney World, Universal Studios, Splendid China, Sea World etc. It is the ideal starting point for day trips to the Atlantic coast or  …see more

from £81 / night

£560 - £689 / week

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from £81 / night

(22) Excellent 

24

Sundown Palm - Windsor Palms villa sleeps 13

Kissimmee / Windsor Palms

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Sundown Palm is our stunning and luxuriously designed 6 bedroom, 3.5 bath villa which has recently been totally renovated with everything being brand new including the opulent fully equipped modern kitchen with granite worktops and stainless steel appliances.A bedroom s  …see more

from £190 / night

£1330 - £1850 / week

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from £190 / night

(1) Good 

23

Shopping and Golfing in Orlando - Venetian Bay Villages townhouse sleeps 8

Kissimmee / Venetian Bay Villages

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The unit is situated in a very safe area and very central to the theme parks.(10/15 min.) Close to shops and restaurants.And 20/30 min.drive from Orlando Aiport ( mco ) 90 min.drive to the gulf coastBedrooms: 3 Bedrooms, Sleeps 8, Beds for 6-8Bedroom 1Bedroom 2Bedroom 3  …see more

from £70 / night

£462 / week

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from £70 / night

8

Emerald Island Gem Near Disney - Emerald Isle Kissimmee house sleeps 12

Kissimmee / Emerald Isle Kissimmee

5 12 3 nights min

  • 5 bedrooms
  • Sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Holiday Lettings Special: Free Pool Heat October through May (Spa heat is always free).Be sure to click the link below to the homeowner's site for more details, a floorplan, more pictures and lots more information. (below where it says 'CLICK HERE - Disney Vac  …see more

from £130 / night

£910 / week

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from £130 / night

(6) Very Good 

56

DisneyDream Orlando Florida - Kissimmee apartment sleeps 6

Central Florida / Kissimmee

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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

48

Mickey's Magical Home - Chatham Park villa sleeps 8

Kissimmee / Chatham Park

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 105 km
  • Swimming pool
Come and stay in the heart of Kissimmee in our beautiful three bedroom villa on the Chatham park community . The community is located just ten minutes from Disney world and is within walking distance of the attraction packed Highway 192 which is full of family fun , r  …see more

from £74 / night

£495 - £630 / week

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from £74 / night

(3) Excellent 

24

5 Bedroom Sunset Luxury Villa with Wireless Internet - Remington villa sleeps 10

Kissimmee / Remington

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
Welcome to our 5 bedroomed villa,unwinding and relaxing in the south facing swimming pool, Our villa boasts many comforts to make your stay a memorable stay. We have lcd televisions in all 5 bedrooms, lounge, all with cable,internet enabled with router/wi fi, dvd playe  …see more

from £100 / night

£695 - £795 / week

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from £100 / night

(1) Excellent 

32

Orlando Disney villa rental - Vista del lago villa sleeps 8

Kissimmee / Vista del lago

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
Three bedrooms, two bathrooms, clean and spacious. Large lounge dining room with TV, DVD, phone, full A/C. Modern kitchen. Master bedroom with full on-suite facilities and walk in shower. Full bathroom for other bedrooms. Screened sunroom Short stay/long stay special ra  …see more

from £50 / night

£455 / week

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from £50 / night

(27) Very Good 

20

Indian Point Villa includes Wireless Internet and Gameroom - Kissimmee villa sleeps 10

Central Florida / Kissimmee

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Our home is a private owned Villa with games room , Pool and Hot-Tub/Spa in Florida, it is fully air conditioned with four bedrooms and two bathrooms, it is located in the community of Indian Point mainly to woods about 15 minutes from the Walt Disney theme parks and cl  …see more

from £87 / night

£604 - £693 / week

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from £87 / night

(1) Excellent 

10

Lake View - Compass Bay townhouse sleeps 9

Kissimmee / Compass Bay

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • 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

84

SKC VIlla - Emerald Isle Kissimmee villa sleeps 8

Kissimmee / Emerald Isle Kissimmee

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly
SKC VillaOur beautiful Orlando vacation Villa rental, with many upgrades is a fabulous holiday rental home with private pool, is set in the peaceful and tranquil location of Emerald Island Resort a gated community. With every possible resort style amenity at your dispos  …see more

from £108 / night

£754 - £1094 / week

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from £108 / night

(7) Excellent 

48

Emerald Magic Villa by Emerald Island Rentals - Emerald Isle Kissimmee villa sleeps 14

Kissimmee / Emerald Isle Kissimmee

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
A 6 bed/5.5 bath villa in Emerald Island Resort offering outstanding amenities such as an air-conditioned game room and a south-facing pool/spa.With 4 king master suites and 2 themed kids rooms, this villa can accommodate up to 14 in sheer luxury. The large pool and spa  …see more

from £185 / night

£1304 - £2154 / week

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from £185 / night

(3) Excellent 

61

Joanna and Sams holiday home from home - Windsor Hills Resort villa sleeps 14

Kissimmee / Windsor Hills Resort

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
There are very few rental homes offering this level of accommodation (space, games room, 5 en suite bedrooms, pool, standard of furniture and decor...) and it also has one further unique advantage: due to it's location our house pool deck is not overlooked by neigh  …see more

from £115 / night

£805 / week

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from £115 / night

(2) Excellent 

70

Scotsman's Retreat - Cumbrian Lakes villa sleeps 10

Kissimmee / Cumbrian Lakes

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool
Scotsman's Retreat is a beautiful and quiet 2 storey 5 bedroom house house on Cumbrian Lakes which is a relatively new gated community build in a conservation area and, as the names suggests, based around 3 large lakes. The villa is situated in an ideal location  …see more

from £95 / night

£665 - £875 / week

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from £95 / night

(1) Excellent 

15

The Lake House - Lake Berkley villa sleeps 10

Kissimmee / Lake Berkley

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
The Lake House is our stunning lake front villa with a pool on the prestigious Lake Berkley Resort just off 1-92 and a genuine 10 minutes from Disney and Sea World, 15 minutes from Universal Studios and International Drive, shopping and restaurants. This is our family v  …see more

from £410 / night

£570 / week

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from £410 / night

(2) Excellent 

71

Sunsetlakes Villa - Kissimmee City villa sleeps 8

Kissimmee / Kissimmee City

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Sunset Lakes is a semi-residential gated community situated off the 192 Irlo Bronson Highway approximately 2 miles west of Interstate 4. World Drive, which is the entrance to all the Disney theme parks is less than 10 minutes drive away. Universal Studios, Sea Worl  …see more

from £70 / night

£450 / week

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from £70 / night

(16) Excellent 

20

Solaz365 - Luxury Rental Home in Kissimmee - Bellavida Resort villa sleeps 12

Kissimmee / Bellavida Resort

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Solaz365 ~~~ Watch our exciting new VIDEO - go to our website and enjoy! ~~~ Welcome to Solaz365, our wonderful holiday home, a place to relax 365 days of the year. If you don't say "WOW" the minute you walk through the door, we will be amazed! The house was built in  …see more

from £175 / night

£1225 / week

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from £175 / night

(54) Excellent 

23

Luxury Lakeside Villa with Hot Tub and Wireless Internet - Crescent Lakes villa sleeps 8

Kissimmee / Crescent Lakes

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
The home comprises a king master suite with a walk in wardrobe and an en suite. A second double with a queen size bed. A third bedroom with two singles, and by utilizing roll-a-way beds in the children's lounge two additional guests can be accommodated. Although th  …see more

from £90 / night

£550 - £690 / week

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from £90 / night

(1) Very Good 

39

OCT BOOKING OFFER 6 Bed Luxury *DISNEY 2 MILES* - Kissimmee villa sleeps 13

Central Florida / Kissimmee

6 13 Min stay varies

  • 6 bedrooms
  • Sleeps 13
  • Min stay varies
  • 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

(1) Excellent 

21

SUPER VIEW, HOT TUB, GAMES ROOM, TURBO WI-FI - Lake Berkley villa sleeps 12

Kissimmee / Lake Berkley

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
*5 Star Rated Accommodation***Over 34 Guest Reviews*** NO BOOKING FEE ! *24hr Guarded and Gated Resort just minutes from Disney World *5 Person Luxury Hot Tub with coloured perimeter lighting *The BEST view on Lake Berkley **In the Centre of the 14 acre Natural Sprin  …see more

from £145 / night

£1480 / week

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from £145 / night

(6) Excellent 

38

Golden Springs Vacation Home with a Pool and Hot Tub - Indian Creek villa sleeps 12

Kissimmee / Indian Creek

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Superb 5 bed 4 bathroom vacation home on Indian CreekNot overlooked with a large pool and hot tub and a removable safety fence to ensure youngsters dont have access if requiredFor those who are more energetic the villa is next to basket ball, tennis courts and a childre  …see more

from £120 / night

£610 - £790 / week

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from £120 / night

22

Executive Lack Backing Disney Villa - Lake Berkley - Lake Berkley villa sleeps 11

Kissimmee / Lake Berkley

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
It pays to book quality, read our reviews, we are not the cheapest nor the most expensive but we like to think we are one of the best Just Imagine lying in your kingsize master bed looking out through your own patio windows with direct access to your own sparkling priv  …see more

from £85 / night

£595 / week

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from £85 / night

(3) Excellent 

24

Lakeside Luxury - Crescent Lakes house sleeps 8

Kissimmee / Crescent Lakes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • 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 £93 / night

£760 - £900 / week

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from £93 / night

24

Luxurious Lake Berkley - 5B/3B - Southern Exposure - Lake Berkley villa sleeps 10

Kissimmee / Lake Berkley

5 10 4 nights min

  • 5 bedrooms
  • Sleeps 10
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Situated in the upmarket gated community of Lake Berkley, our exquisite villa offers a serene oasis where you can relax and enjoy the Florida sun after a hard day at the parks or at one of the spectacular shopping malls that Orlando has to offer. Experience 5 star livin  …see more

from £123 / night

£860 / week

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from £123 / night

37

1308 Caribe Suite - Kissimmee condo sleeps 6

Central Florida / Kissimmee

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
Condo 1308 is based in the Caribe Cove Resort. Our luxurious condo with ample amenities will comfort you, making Caribe Cove a great place to retreat to for a long-awaited vacation. Caribe Cove Resort is perfect for your vacation and holidays. Condo 1308 features abou  …see more

from £91 / night

£637 / week

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from £91 / night

(1) Excellent 

20

Luxury Pool/Spa Villa Near Disney - Emerald Isle Kissimmee villa sleeps 17

Kissimmee / Emerald Isle Kissimmee

8 17 Min stay varies

  • 8 bedrooms
  • Sleeps 17
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Only 3 miles to Disney, 15 miles to SeaWorld, 17 miles from Universal Studio and easy access to all major theme parks, shipping center, restaurants, this lovely 8 bedroom 4.5 bath heated pool/spa villa is located on the prestigious Emerald Island Resort, a beautiful com  …see more

from £231 / night

£1077 - £2454 / week

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from £231 / night

(2) Very Good 

59

Central Florida / Kissimmee

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

 …see more

from £81 / night

£566 / week

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from £81 / night

(3) Very Good 

43

Lizzie's Gem, Wonderful Vacation Rental with Wireless Internet - Emerald Isle Kissimmee villa sleeps 10

Kissimmee / Emerald Isle Kissimmee

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are situated 5 minutes from Disney & local shops & amenities are just around the corner.Emerald Island is the closest community to the theme parks.Whilst staying in our home you can benefit from all the facilities of Emerald Island Resort, including volleybal  …see more

from £70 / night

£490 - £610 / week

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from £70 / night

(2) Very Good 

18

River Island at Orange Lake - Orange Lake Resort villa sleeps 8

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
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 Resort featur  …see more

from £171 / night

£1200 / week

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from £171 / night

(9) Excellent 

88

Spacious Bellair Villa includes a Terrace,Gameroom - Bellavida Resort villa sleeps 14

Kissimmee / Bellavida Resort

6 14 5 nights min

  • 6 bedrooms
  • Sleeps 14
  • 5 nights min
  • Nearest beach 111 km
  • Swimming pool
  • Child friendly
This home is very spacious, (3475 sq ft), located on the beautiful Bella Vida Resort. Large open plan family room including the kitchen opens on to the decked area, outdoor private pool and jacuzzi. Family room has large TV and DVD. Games room with pool table and fooseb  …see more

from £166 / night

£1158 - £1535 / week

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from £166 / night

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