List your home
Apply filters
£ to

Holiday homes 1,761

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • United States Clear
  • Florida Clear
  • Central Florida Clear
  • Kissimmee Clear

Location

  • All locations
  • Bass Lakes Estate (1)
  • Bellavida Resort (24)
  • Calabria, Orlando (4)
  • Cane Island (4)
  • Chatham Park (2)
  • Compass Bay (6)
  • Coral Cay (9)
  • Country Creek (1)
  • Creekside (1)
  • Crescent Lakes (17)
  • Crestwynd Bay (21)
  • Crystal Cove Resort (4)
  • Cumbrian Lakes (24)
  • Doral Woods (7)
  • Eagle Pointe (10)
  • Emerald Isle Kissimmee (62)
  • Encantada Resort (5)
  • Fiesta Key (7)
  • Formosa Gardens (12)
  • Hamilton's Reserve (1)
  • Indian Creek (23)
  • Indian Point (3)
  • Indian Ridge (5)
  • Indian Ridge Oaks (6)
  • Kissimmee City (52)
  • Lake Berkley (30)
  • Lake Marion (5)
  • Legacy Dunes Resort (6)
  • Liberty Village (5)
  • Lindfields (20)
  • Lucaya Village (2)
  • Oak Island Cove (8)
  • Oak Island Harbor (2)
  • Orange Lake Resort (7)
  • Paradise Palms (36)
  • Regal Oaks (8)
  • Remington (2)
  • Rolling Hills at Formosa (4)
  • Seasons Resort (20)
  • Sunset Lakes (12)
  • Terra Verde Resort (15)
  • The Hamlets (4)
  • Trafalgar Village (5)
  • Tuscany, Florida (3)
  • Venetian Bay Villages (15)
  • Veranda Palms (8)
  • Villasol (3)
  • Vista del lago (2)
  • Westside (25)
  • Windsor Hills Resort (50)
  • Windsor Palms (26)
  • Winward Cay (2)

more +

less -

Also consider

Emerald Isle Kissimmee
47 properties
Cumbrian Lakes
29 properties
Kissimmee City
24 properties
Bellavida Resort
21 properties
Lake Berkley
20 properties

Filters applied: Swimming pool (1,761)

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
1,761 Results   |  
14 Photos

Kissimmee / Bellavida Resort

House / 6 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £137 / night

£959 - £1236 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

33 Photos

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 8

4 Nights min stay

Add to shortlist

from £89 / night

£620 - £799 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

33 Photos

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 12

4 Nights min stay

Add to shortlist

from £127 / night

£883 - £1918 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

Featured properties

23 Photos

Kissimmee / Windsor Hills Resort

Condo / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £51 / night

£357 - £892 / week

View

Key info:

  • Nearest beach 143 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

10 Photos

Central Florida / Kissimmee

Apartment / 1 Bedroom / sleeps 4

4 Nights min stay

Add to shortlist

from £79 / night

£547 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

23 Photos

Central Florida / Kissimmee

Townhouse / 6 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £77 / night

£536 - £829 / week

View

Key info:

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

33 Photos

Central Florida / Kissimmee

Villa / 7 Bedrooms / sleeps 16

3 Nights min stay

Add to shortlist

from £101 / night

£701 - £1606 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 113 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

8 Photos

Kissimmee / Emerald Isle Kissimmee

House / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £128 / night

£892 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Bedding Summary: Bedroom #1: King Bed Bedroom #2: King Bed Bedroom #3: King Bed Bedroom #4: Queen Bed Bedroom #5: (2) Double Beds  …see more

42 Photos

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 14

2 Nights min stay

Add to shortlist

from £164 / night

£1147 / week

View

Key info:

  • Nearest beach 114 km
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

24 Photos

Central Florida / Kissimmee

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £37 / night

£255 - £318 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

4 Photos

Central Florida / Kissimmee

Villa / 3 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £51 / night

£357 - £446 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
 …see more

24 Photos

Central Florida / Kissimmee

Apartment / 3 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £58 / night

£402 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
ORLANDO / DISNEY - 3/2 COMFORTABLE & AFFORDABLE !  …see more

16 Photos

Central Florida / Kissimmee

Villa / 4 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £57 / night

£395 - £510 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Disney location with secluded heated pool and King sized Four Poster Bed. This newly renovated property, located in one of the nicest residential communities in Kissimmee, is a great base for any holiday in the area.  …see more

23 Photos

Central Florida / Kissimmee

Villa / 6 Bedrooms / sleeps 14

1 night min stay

Add to shortlist

from £105 / night

£733 - £1590 / week

View

Key info:

  • Nearest beach 64 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
 …see more

14 Photos

Central Florida / Kissimmee

B&B / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £23 / night

£161 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

23 Photos

Central Florida / Kissimmee

Condo / 3 Bedrooms / sleeps 8

4 Nights min stay

Add to shortlist

from £38 / night

£264 - £306 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 113 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

27 Photos

Central Florida / Kissimmee

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £81 / night

£567 - £803 / week

View

Key info:

  • Nearest beach 95 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Keywords: Hot Tub, Jacuzzi, Spa, Secluded, Private, Free Pool Heat, Free Phone Calls, Free GPS, Computer, Internet, Wireless, Includes all Taxes, Villa, Countryside, Disney, Universal, See World, International Drive, Downtown Disney,Magic Kingdom, cable TV, MLS, Fox Soc  …see more

23 Photos

Kissimmee / Terra Verde Resort

Villa / 6 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £119 / night

£831 - £1155 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This superb luxury vacation pool home with 6 bedrooms, 5.5 bathrooms and straight forward fully inclusive pricing has everything that you could possibly need for the perfect holiday.  …see more

19 Photos

Kissimmee / Windsor Hills Resort

Townhouse / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £71 / night

£491 - £602 / week

View

Key info:

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

20 Photos

Central Florida / Kissimmee

Townhouse / 4 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £60 / night

£420 - £630 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Our townhouse on the Regal Oaks at Old Town resort is in an ideal location, Old Town has much to offer with its shops, bars, fairground attractions, with its own childrens fair are. You can also be catapulted 365 feet into the air by the human slingshot Every Thursday e  …see more

24 Photos

Kissimmee / Indian Creek

House / 5 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £236 / night

£1650 - £2141 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
From the moment you meet us online, we are with you every step of the way to help make the planning of your dream vacation as easy as possible. We offer our guests a welcome as warm as the sun and the utmost in personal attention.  …see more

15 Photos

Kissimmee / Windsor Palms

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £215 / night

£1500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
"Vista Palm” is a luxurious 6 bedroom, 3.5 bathroom home with private south facing heated swimming pool overlooking conservation area which is perfect for family groups sleeping up to 12 guests in comfort.  …see more

15 Photos

Central Florida / Kissimmee

Condo / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £54 / night

£373 - £634 / week

View

Key info:

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

21 Photos

Kissimmee / Veranda Palms

Villa / 4 Bedrooms / sleeps 8

4 Nights min stay

Add to shortlist

from £80 / night

£558 - £750 / week

View

Key info:

  • Nearest beach 104 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Brand new for 2011. Only 4 miles to Disney. 4 bedroom, 3 bathroom luxury villa with modern contemporary furnishings. Games room, pool + spa. Cable, wireless internet.  …see more

26 Photos

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 8

4 Nights min stay

Add to shortlist

from £71 / night

£491 - £602 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
 …see more

13 Photos

Kissimmee / Kissimmee City

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £36 / night

£246 / week

View

Key info:

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

22 Photos

Kissimmee / Cumbrian Lakes

Villa / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £95 / night

£665 - £875 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 114 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
5 bedrooms;3 en suites bathrooms; private pool and spa; optional pool heating; Home Cinema; Fully air conditioned games room; south west facing pool; freeWiFi and high speed internet access; all bedrooms have flat screen cable TVs; free local and international calls All  …see more

30 Photos

Central Florida / Kissimmee

Villa / 8 Bedrooms / sleeps 20

1 night min stay

Add to shortlist

from £137 / night

£955 - £1720 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Some pets are welcome - please contact the owner
 …see more

9 Photos

Kissimmee / Venetian Bay Villages

Townhouse / 3 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £64 / night

£442 - £665 / week

View

Key info:

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

24 Photos

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £89 / night

£623 - £833 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Luxury tropical five star resort and house. Close to Disney parks and within range of Florida's west coast beaches.  …see more

15 Photos

Kissimmee / Lake Marion

Villa / 3 Bedrooms / sleeps 6

4 Nights min stay

Add to shortlist

from £41 / night

£287 - £351 / week

View

Key info:

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

8 Photos

Central Florida / Kissimmee

Condo / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £50 / night

£350 - £665 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
3 bed, 2 bath luxury apartment. 4 heated outdoor pools with jacuzzis. Tropical style setting, in quiet and spacious grounds. Free wifi. Nearest international airport is Orlando (35 mins) or Tampa (1hr 10 mins). Car hire is essential.  …see more

27 Photos

Kissimmee / Lake Berkley

House / 6 Bedrooms / sleeps 12

2 Nights min stay

Add to shortlist

from £115 / night

£803 - £1048 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

29 Photos

Kissimmee / Lake Berkley

House / 7 Bedrooms / sleeps 14

2 Nights min stay

Add to shortlist

from £125 / night

£870 - £1115 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
 …see more

15 Photos

Central Florida / Kissimmee

Apartment / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £44 / night

£308 - £482 / week

View

Key info:

  • Nearest beach 64 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • Pets welcome
 …see more

24 Photos

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £182 / night

£1274 - £1624 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
This villa is situated in the prestigous Windsor Hills resort. Only 1.5 miles from Walt Disney World and all the major Orlando attractions. Great, Yeah!  …see more

18 Photos

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £100 / night

£700 - £975 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Luxury 4 Bed 3 bath villa with pool, spa and games room incorporating air hockey table, football table and pool table. Free International phone calling, Free WifI and free internet streaming for unlimited free movies from Netflix. Two spacious living rooms. Baby goods.  …see more

13 Photos

Kissimmee / Windsor Palms

Apartment / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £50 / night

£350 - £450 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Beautiful resort appartment close to Disney. 3bedroom, 2 bathroom Swimming pool, tennis, basket ball, gym, games room  …see more

14 Photos

Kissimmee / Lindfields

Condo / 3 Bedrooms / sleeps 8

1 night min stay

Add to shortlist

from £71 / night

£491 - £602 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
 …see more

15 Photos

Kissimmee / Windsor Palms

Condo / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £58 / night

£402 - £536 / week

View

Key info:

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

17 Photos

Kissimmee / Crestwynd Bay

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £104 / night

£725 - £1000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
5 Bed, 3 Bath Luxury Villa, Pool, Spa, Games Room, Free In-House Wireless Internet - Emerald Island Resort. Ideal location,3 miles from Disney, one mile shops, Restaurants, mini golf, supermarkets and a medical centre. Internet streaming for Netflix etc Baby facilities  …see more

32 Photos

Central Florida / Kissimmee

Villa / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £70 / night

£485 - £841 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
The Hamlets villa description. Looking for a vacation home with a private secluded pool area? - Here it is! OUR GUESTS SAY, "Great Home! We stayed at this house for 5 nights! It was super roomy! Very close to Disney. I would recommend this house to large families and  …see more

22 Photos

Kissimmee / Seasons Resort

Villa / 5 Bedrooms / sleeps 10

4 Nights min stay

Add to shortlist

from £90 / night

£625 - £840 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Seasons Sunshine Villa named from the fact that the pool is in sun all day offers the ideal location for a large family or two family holiday of a lifetime.  …see more

11 Photos

Central Florida / Kissimmee

Condo / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £37 / night

£255 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
 …see more

22 Photos

Central Florida / Kissimmee

Condo / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £43 / night

£300 - £618 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
 …see more

8 Photos

Kissimmee / Emerald Isle Kissimmee

Townhouse / 3 Bedrooms / sleeps 8

Min stay varies

Add to shortlist

from £43 / night

£300 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Emerald Island has a great location, only minutes from Disney and theres loads of shops and restaurants close by. Our house has a brilliant position right infront of the heated pool and spa and you can just sit on the balcony and chill out after a busy day at the parks  …see more

14 Photos

Kissimmee / Windsor Hills Resort

House / 5 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £293 / night

£2048 - £2771 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Sevillle floor plan 2236sqft 5 bedroom 5 barth (2 story) Pool home We invite you to enjoy your next vacation at our luxurious, brand new and beautifully decorated 5 bed/5 bath Home with 28ft pool. Sleeping accommodation features two elegant master suites with king size  …see more

Very Good 4/5 

18 Photos

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 10

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £64 / night

£446 - £685 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
flipkey
Imagine Your next vacation! This gorgeous house-Emma's Castle features everything t  …see more

Excellent 5/5 

45 Photos

Central Florida / Kissimmee

Villa / 6 Bedrooms / sleeps 13

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £96 / night

£669 - £829 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
 …see more

Excellent 5/5 

23 Photos

Kissimmee / Terra Verde Resort

Townhouse / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £60 / night

£420 - £475 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Palm Heaven Villa is a luxurious four bedroomed family townhouse in a quiet location close to all the resort facilities, with its' own private screen enclosed heated pool. Featuring brand new flat screen TVs in all the bedrooms: come and sample the luxury! Relax and wat  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page