List your home
Apply filters
£ to

Price

£10 - 500+

Price per night

£ to per night

Location

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

Location

Kissimmee

  • Show all locations
  • Bass Lakes Estate (1)
  • Bellavida Resort (20)
  • Calabria, Orlando (3)
  • Cane Island (3)
  • Chatham Park (1)
  • Compass Bay (4)
  • Coral Cay (4)
  • Country Creek (1)
  • Creekside (1)
  • Crescent Lakes (13)
  • Crestwynd Bay (5)
  • Cumbrian Lakes (26)
  • Doral Woods (7)
  • Eagle Pointe (8)
  • Emerald Isle Kissimmee (46)
  • Encantada Resort (5)
  • Fiesta Key (3)
  • Formosa Gardens (11)
  • Hamilton's Reserve (1)
  • Indian Creek (13)
  • Indian Ridge (4)
  • Indian Ridge Oaks (4)
  • Kissimmee City (25)
  • Lake Berkley (23)
  • Lake Marion (1)
  • Legacy Dunes Resort (3)
  • Liberty Village (3)
  • Lindfields (15)
  • Lucaya Village (1)
  • Oak Island Cove (7)
  • Oak Island Harbor (4)
  • Orange Lake Resort (6)
  • Paradise Palms (9)
  • Regal Oaks (5)
  • Remington (8)
  • Rolling Hills at Formosa (1)
  • Seasons Resort (11)
  • Sunset Lakes (8)
  • Terra Verde Resort (11)
  • The Hamlets (2)
  • Trafalgar Village (4)
  • Tuscany, Florida (3)
  • Venetian Bay Villages (14)
  • Veranda Palms (6)
  • Villasol (2)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (15)
  • Windsor Palms (15)
  • Winward Cay (2)

more +

less -

Bedrooms

Show all

  • Show all
  • Studio
  • 1 Bedroom
  • 2 Bedrooms
  • 3 Bedrooms
  • 4 Bedrooms
  • 5 Bedrooms
  • 6 Bedrooms
  • 7 Bedrooms
  • 8 Bedrooms
  • 9 Bedrooms
  • 10 Bedrooms
  • 11 Bedrooms
  • 12 Bedrooms
  • 13 Bedrooms
  • 14 Bedrooms
  • 15+ Bedrooms

more +

less -

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
32 of 583 Results

Sort by: Default

  • Default
  • Price low to high
  • Price high to low
  • Reviews

from £173 / night

£1207 - £1744 / week

View

(2) Excellent 5/5 

1 / 15

Holiday home with golf nearby in Emerald Isle Kissimmee

House / 6 Bedrooms / sleeps 13

  • Beach / lakeside relaxation
  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £173 / night

£1207 - £1744 / week

View

Wow factor Extra large saline pool South facing deck and slide THX Cinema, with leather tiered seating Smart Tv's Quite location conservation view. Games room, cycles Most comfortable beds Full size bbq outside kitchen Lots of extras not included in other rental homes Book early to avoid disappointment. Holiday periods are extremely busy, so dont delay.  …see more

from £94 / night

£652 - £1141 / week

View

(1) Very Good 4/5 

1 / 21

Holiday home in Kissimmee

House / 5 Bedrooms / sleeps 10

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

Very Good 4/5 

Add to shortlist

from £94 / night

£652 - £1141 / week

View

Conveniently located near the Disneyland, this spacious and comfortable house has its own swimming pool and is ideal for a family holiday. We'll do our best to accommodate your requests. Book now!  …see more

from £77 / night

£534 - £735 / week

View

1 / 19

Holiday villa in Kissimmee

Villa / 4 Bedrooms / sleeps 10

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

Add to shortlist

from £77 / night

£534 - £735 / week

View

4 bed 3 bath heated pool close to Disney flat screen tv's  …see more

Featured properties

from £140 / night

£980 - £1610 / week

View

(3) Excellent 5/5 

1 / 24

Holiday villa in Veranda Palms

Villa / 5 Bedrooms / sleeps 14

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £140 / night

£980 - £1610 / week

View

Luxury 5 bedroom home Comfortably sleeps 12 -14 people Private pool and spa Secluded Pool Deck Gated Community Upstairs TV Den FREE Wireless Internet and wireless printer Fully Equipped Games Room Cable TV's in all Bedrooms  …see more

from £150 / night

£1050 - £1700 / week

View

(3) Very Good 4.5/5 

1 / 23

Holiday villa in Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

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

Very Good 4.5/5 

Add to shortlist

from £150 / night

£1050 - £1700 / week

View

6 bedroom 4 bathroom Villa, South facing pool & spa located in the Windsor Hills Resort just 1.5 miles (2.5 km) from the gates of Walt Disney World. The resort offers a variety of recreation and activities for all ages and there are an abundance of golf courses nearby. Rental Period and Occupancy: Check-in time is 4 p.m. Check out time is 10 a.m.  …see more

from £105 / night

£735 - £937 / week

View

(1) Very Good 4.5/5 

1 / 11

Holiday villa in Kissimmee

Villa / 5 Bedrooms / sleeps 12

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

Very Good 4.5/5 

Add to shortlist

from £105 / night

£735 - £937 / week

View

5 Bedroom, 4 bathroom, large pool, hot tub, games room, pc with wi-fi internet, cable tv, full kitchen and laundry facilities, free world wide phone calls, close to Disney parks Close to all Disney parks & also Universal, Seaworld and other parks, 1 Mile from Hwy 192, Quiet Location  …see more

from £116 / night

£806 / week

View

(2) Very Good 4.5/5 

1 / 18

Holiday villa with shared pool, golf nearby in Orange Lake Resort

Villa / 2 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages

Very Good 4.5/5 

Add to shortlist

from £116 / night

£806 / week

View

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. Superb base for Walt Disney World and Golfing holidays.  …see more

from £95 / night

£665 - £840 / week

View

(2) Very Good 4.5/5 

1 / 18

Holiday villa in Kissimmee

Villa / 6 Bedrooms / sleeps 14

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

Very Good 4.5/5 

Add to shortlist

from £95 / night

£665 - £840 / week

View

6 bedroom, 4 bathroom villa with pool which sleeps up to 14 people, free high speed internet. Located in a quiet residential area just minutes from highway 192 with many restaurants, bars and shops close by. 15 minute drive from Disney.  …see more

from £74 / night

£518 - £714 / week

View

(5) Excellent 5/5 

1 / 24

Remington holiday home rental

House / 4 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Nearest beach 76 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £74 / night

£518 - £714 / week

View

Lovely 4 bedroomed villa with south facing heated pool with extensive lake views, perfectly located for all the main attractions. Located in the beautiful recreational golfing community of Remington in Kissimmee. Fully equipped for a perfect vacation. Free WiFi. Very spacious two storey house, beautifully furnished and perfect for all the family.  …see more

from £144 / night

£1007 - £1275 / week

View

(3) Very Good 4.5/5 

1 / 23

Holiday villa with swimming pool in Kissimmee

Villa / 6 Bedrooms / sleeps 13

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

Very Good 4.5/5 

Add to shortlist

from £144 / night

£1007 - £1275 / week

View

6 beds, 4Bath with 3 master suites, new digital TV set in all bed rooms, a 60" TV in living room, Minutes to Disney World and shopping malls, A great place for family vacation with gated community & forest view. A Child high chair, 3 strollers are available on site Recently renovated,Hockey table,foosball and games set in game room.  …see more

from £106 / night

£739 - £1074 / week

View

(2) Excellent 5/5 

1 / 10

Townhouse rental in Paradise Palms with indoor pool, golf nearby

Townhouse / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £106 / night

£739 - £1074 / week

View

The pool can be heated it is South facing and has the sun on it all day.The house is on the first road as you go in and has a green space directly behind it so it is not over looked from behind.We are in a gated Community so there is 24 hour security .  …see more

from £125 / night

£875 - £1875 / week

View

(4) Excellent 5/5 

1 / 20

Holiday townhouse in Kissimmee

Townhouse / 5 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £125 / night

£875 - £1875 / week

View

Luxury 5 Bed, 4 bathroom townhome on a 5* resort, just 10 mins from Disney. Property features private pool and terrace, TVs in every room, free WiFi, DVD player and Xbox. Resort amenities include heated pool and bar, Jacuzzi, games room, fitness room and Movie Theatre.  …see more

from £135 / night

£940 - £1276 / week

View

(2) Excellent 5/5 

1 / 17

Holiday villa with shared pool in Kissimmee

Villa / 6 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Nearest beach 92 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £135 / night

£940 - £1276 / week

View

Exclusive, large villa (approx. 2500 Sq Ft) with a capacity to sleep 12 people comfortably with 6 bedrooms and 4 bathrooms. Luxurious private heated pool and hot tub with games room for the kids - both big and little alike. A great place to Rest, Relax & Play!  …see more

from £144 / night

£1007 - £2081 / week

View

(1) Excellent 5/5 

1 / 24

Holiday villa in Emerald Isle Kissimmee

Villa / 7 Bedrooms / sleeps 16

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

Add to shortlist

from £144 / night

£1007 - £2081 / week

View

3 Miles from Disney in Emerald Island resort ~ Air-conditioned game room with pool table, air hockey, foosball and large screen TV ~ 7 bedrooms, 4.5 bathrooms ~ 2 Master suites with King size beds ~ Large south-facing pool and spa - Themed kids bedrooms NOTE: We prefer Sat-Sat bookings. All variations are considered by owner, so please ask.  …see more

from £70 / night

£490 - £560 / week

View

(7) Very Good 4.5/5 

1 / 24

Holiday townhouse in Kissimmee

Townhouse / 3 Bedrooms / sleeps 6

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

Very Good 4.5/5 

Add to shortlist

from £70 / night

£490 - £560 / week

View

Enjoy this 3 bedroom/ 2.5 bathrooms townhouse, located only 10 minutes from Disney. All bedrooms are equipped with flat panel TVs. The house comes with a fully equipped kitchen and the comfortable living area including a new 32"TV. Surrounded by over 25 golf courses. You'll enjoy the living area- complete with a new flat panel 32" TV with a DVD player.  …see more

from £70 / night

£490 - £630 / week

View

(1) Very Good 4.5/5 

1 / 22

Holiday villa with swimming pool in Kissimmee

Villa / 4 Bedrooms / sleeps 10

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

Very Good 4.5/5 

Add to shortlist

from £70 / night

£490 - £630 / week

View

Lindfield is one of the closest areas to Disney  …see more

from £137 / night

£954 - £1264 / week

View

(5) Excellent 5/5 

1 / 18

Kissimmee holiday villa rental

Villa / 6 Bedrooms / sleeps 14

  • Nearest beach 111 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £137 / night

£954 - £1264 / week

View

Very spacious home (3475 sq ft) located on beautiful BellaVida Resort. Large open plan family room with TV, DVD. Games room & further lounge/ dining room. Fully fitted kitchen. All bedrooms ensuite. Outdoor private pool & jacuzzi. Backs on to wooded conservation area. Free internet and local calls.Ideal location for Walt Disney World and the areas other famous attractions.  …see more

from £147 / night

£1024 - £1474 / week

View

(3) Excellent 5/5 

1 / 24

Villa rental in Kissimmee

Villa / 6 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning

Excellent 5/5 

Add to shortlist

from £147 / night

£1024 - £1474 / week

View

Close to Disney Parks Secure Gated Entrance Clubhouse 58 seat 3D Movie Theater Nintendo Wii Suite Fitness Room & Gym Billiard Room Video Arcade Lighted Tennis Courts Lighted Basketball Courts Volleyball Courts Children's Play Area Olympic Size Swimming Pool Belle's has won awards 3 Years running 2011,2012 & 2013 for top holiday rental in the Disney area.  …see more

from £105 / night

£735 / week

View

(37) Excellent 5/5 

1 / 24

Indian Creek holiday villa rental

Villa / 5 Bedrooms / sleeps 12

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

Excellent 5/5 

Add to shortlist

from £105 / night

£735 / week

View

Completely private pool and spa. Disney is 3 miles about a 5-10 minute drive, Universal & Sea World are about a 15 minute drive, more than 10 fantastic restaurants within 5 minutes drive. Shopping centers and outlets within 20 minutes drive Trip Advisor Certificate of Excellence Award Winners 2014 please see our reviews from previous guests  …see more

from £125 / night

£870 - £1222 / week

View

(1) Excellent 5/5 

1 / 17

Home rental in Kissimmee

House / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £125 / night

£870 - £1222 / week

View

This luxury 4 bedroom and 3 bathroom villa is located in the established community of Oak Island Cove. This location is probably one of the closest to Disney World's' main gate and within walking distance ( 5 mins) to shopping and the many great restaurants situated on  …see more

from £50 / night

£350 - £665 / week

View

(5) Excellent 5/5 

1 / 14

Terra Verde Resort holiday townhouse rental

Townhouse / 3 Bedrooms / sleeps 6

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

Excellent 5/5 

Add to shortlist

from £50 / night

£350 - £665 / week

View

All tile on the fist floor with laminate flooring elsewhere, Large Hot Tub, in a very desirable Resort  …see more

from £77 / night

£535 - £575 / week

View

(7) Very Good 4.5/5 

1 / 15

Kissimmee holiday townhouse rental

Townhouse / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning

Very Good 4.5/5 

Add to shortlist

from £77 / night

£535 - £575 / week

View

Holiday Home, Free wireless wifi, private Splash pool, South facing conservation area. Near Disney Theme Parks. Shopping and restaurants nearby.  …see more

from £113 / night

£785 - £980 / week

View

(2) Excellent 5/5 

1 / 23

Kissimmee City holiday villa rental

Villa / 5 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £113 / night

£785 - £980 / week

View

Stunning Lake View Orlando Florida Vacation Rental Holiday Villa in Kissimmee. Spacious, Beautifully Furnished Home with Pool, Spa, 55" Cable HDTV, WiFi, Gas BBQ, Games Room, Free Calls, Baby Equipment. Near Disney, Golf, Fishing & all the Orlando area has to offer. A fully monitored alarm system, smoke alarms & 24 hour Security Patrols for your added peace of mind.  …see more

from £163 / night

£1141 - £2014 / week

View

(2) Very Good 4.5/5 

1 / 24

Villa rental in Kissimmee

Villa / 6 Bedrooms / sleeps 14

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £163 / night

£1141 - £2014 / week

View

3 Miles from Disney in exclusive Emerald Island gated resort community ~Air-conditioned game room with pool table, and a 100” movie theater ~ 6 bedrooms, 5.5 bathrooms ~ 4 Master suites with King size beds ~ 2 themed kids rooms * Large South facing pool/spa Free BBQ, Free WiFi, Free Phone Calls, Luxuriously appointed and close to Disney (3 miles/5 minutes)  …see more

from £163 / night

£1141 - £2014 / week

View

(3) Excellent 5/5 

1 / 27

Villa rental in Kissimmee

Villa / 6 Bedrooms / sleeps 14

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

Excellent 5/5 

Add to shortlist

from £163 / night

£1141 - £2014 / week

View

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 £84 / night

£588 - £833 / week

View

(1) Excellent 5/5 

1 / 27

Holiday villa with swimming pool in Kissimmee

Villa / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £84 / night

£588 - £833 / week

View

4 bed 3 bath Villa in kissimmee Florida, West Facing heated private pool with spa, in sought after location,15 minutes from Disney and major attractions, Restaurants and Shopping Malls all taxes and Pool Heat included  …see more

from £76 / night

£530 - £795 / week

View

(2) Excellent 5/5 

1 / 24

Holiday villa with golf nearby in Kissimmee

Villa / 5 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £76 / night

£530 - £795 / week

View

Relax in this ex-showhome villa, with a beautiful south facing pool and situated next to one of the best golf courses.Based on one of the finest gated communities in kissimmee, this villa and location is perfect for all families, with fantastic amenities.Golfers, shops  …see more

from £60 / night

£420 - £525 / week

View

(1) Very Good 4.5/5 

1 / 14

Holiday villa rental

Villa / 4 Bedrooms / sleeps 10

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

Very Good 4.5/5 

Add to shortlist

from £60 / night

£420 - £525 / week

View

Large property, sleeps ten, fully equipped kitchen with ice making fridge. Large enclosed pool, games room, Linen and towels provided. 10 minutes drive from Disney and close to main attractions.  …see more

from £100 / night

£700 - £850 / week

View

(2) Very Good 4.5/5 

1 / 24

Holiday home with indoor pool, golf nearby in Kissimmee

House / 6 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning

Very Good 4.5/5 

Add to shortlist

from £100 / night

£700 - £850 / week

View

Large spacious well equipped house which is ideally sited in a rpivate gated community 5 minutes from Disney  …see more

from £114 / night

£795 - £970 / week

View

1 / 24

Holiday home in Kissimmee

House / 5 Bedrooms / sleeps 10

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning

Add to shortlist

from £114 / night

£795 - £970 / week

View

We hope if you pick our villa. We have being renting villas in Florida for the last 10 years and we decided to buy our own home. Over the years we have picked up ideas from other villas and hopefully we have put in everything into our villa to make your stay enjoyable.  …see more

from £71 / night

£495 - £650 / week

View

(6) Excellent 5/5 

1 / 20

Holiday townhouse in Kissimmee

Townhouse / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £71 / night

£495 - £650 / week

View

The townhouse is a modern, beautifully appointed home complete with the space and facilities you need to make your stay a memorable one. The open plan format offers plenty space with separate seating and dining areas and fully equipped kitchen.  …see more

from £59 / night

£410 - £550 / week

View

(4) Excellent 5/5 

1 / 21

Holiday villa with swimming pool in Kissimmee

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £59 / night

£410 - £550 / week

View

Centrally located near all Disney, Universal and Sea World parks, we offer a beautiful family home with a stunning lake view, perfect to relax after busy family outings. The 192 offers a wide range of eateries as well as conveniently located near many supermarkets. For those who enjoy shopping, Premium Outlets nearby, offers designer clothing at discounted prices.  …see more
first

Also consider

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