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 (6)
  • Cane Island (1)
  • Chatham Park (1)
  • Coral Cay (1)
  • Creekside (1)
  • Crescent Lakes (6)
  • Crestwynd Bay (1)
  • Cumbrian Lakes (10)
  • Doral Woods (4)
  • Eagle Pointe (2)
  • Emerald Isle Kissimmee (15)
  • Encantada Resort (1)
  • Formosa Gardens (7)
  • Indian Creek (2)
  • Indian Ridge (3)
  • Indian Ridge Oaks (3)
  • Kissimmee City (3)
  • Lake Berkley (8)
  • Lake Marion (1)
  • Legacy Dunes Resort (1)
  • Liberty Village (1)
  • Lindfields (4)
  • Lucaya Village (1)
  • Oak Island Cove (3)
  • Orange Lake Resort (5)
  • Paradise Palms (2)
  • Regal Oaks (2)
  • Remington (2)
  • Seasons Resort (2)
  • Sunset Lakes (2)
  • Terra Verde Resort (3)
  • The Hamlets (2)
  • Trafalgar Village (4)
  • Tuscany, Florida (3)
  • Venetian Bay Villages (2)
  • Veranda Palms (2)
  • Villasol (2)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (8)
  • Windsor Palms (4)
  • Winward Cay (1)

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

Filters applied: Water sports (175)

32 of 175 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 £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 £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

Featured properties

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 £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 £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 £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 £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 £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 £109 / night

£760 - £1000 / week

View

(3) Excellent 5/5 

1 / 19

Kissimmee holiday villa rental

Villa / 5 Bedrooms / sleeps 14

  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £109 / night

£760 - £1000 / week

View

Stunning 5 bed, 5 bath house with pool & jacuzzi, games room and den in the Windsor Hills gated community, less than 5 minutes from Disney. Our holiday home has over 2,700 square feet of space including 3 king bedrooms and a kids bedroom with 2 sets of bunk beds. Windsor Hills is the most highly rated community in the Orlando area and is less than 2 miles from Disney.  …see more

from £71 / night

£495 - £795 / week

View

(3) Very Good 4.5/5 

1 / 15

Holiday villa rental

Villa / 5 Bedrooms / sleeps 12

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £71 / night

£495 - £795 / week

View

Your dream holiday starts here !! Villa Pip is nestled within a 200 acre conservation area and has a South West facing pool and spa that backs onto a beautiful conservation area.. We also offer - Free international calls - Free use of PC / high speed internet  …see more

from £60 / night

£420 / week

View

(3) Very Good 4.5/5 

1 / 19

Townhouse rental in Regal Oaks with shared pool

Townhouse / 4 Bedrooms / sleeps 10

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

Very Good 4.5/5 

Add to shortlist

from £60 / night

£420 / week

View

This well equipped townhouse is situated at Regal Oaks, a fully managed resort, 3 miles from Disney. Ideal for families or groups of up to 10 people. The house has 4 bedrooms, two with en-suite facilities with a further two twin rooms that share a full bathroom. This well equipped lakeside townhouse is situated only 3 miles from Disney.  …see more

from £65 / night

£450 - £525 / week

View

(4) Excellent 5/5 

1 / 12

Holiday home in Kissimmee

House / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £65 / night

£450 - £525 / week

View

The dream home of a British family. A grand floor plan that is ideal for up to eight guests. Open the patio doors and you will find a serene, secluded sundeck and pool. You will find reviews of our villa on Flipkey at: http://www.flipkey.com/kissimmee-vacation-rentals  …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 £46 / night

£321 - £537 / week

View

(1) Very Good 4/5 

1 / 22

Holiday home with shared pool in Kissimmee

House / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over 5
  • Car essential

Very Good 4/5 

Add to shortlist

from £46 / night

£321 - £537 / week

View

This spacious vacation home provides the ideal home-away-from-home base for all your family's plans. Located near Walt Disney Resort, historic Kissimmee and the Orlando International Airport. The large kitchen features all the appliances and utensils guests would need. Golfer? Forget your cold, wet and soggy home course, and enjoy this winter wonderland for Golf!  …see more

from £65 / night

£450 - £599 / week

View

1 / 24

Holiday villa rental

Villa / 4 Bedrooms / sleeps 8

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

Add to shortlist

from £65 / night

£450 - £599 / week

View

Located in a Family friendly community with free use of resort facilities our well-furnished villa with pool and hot tub can comfortably accommodate up to 8 Guests. Less than 15 miles from Walt Disney World. Outdoor Pool & Spa Heat is available at an additional cost.  …see more

from £86 / night

£600 - £700 / week

View

1 / 15

Holiday villa with shared pool, golf nearby in Kissimmee

Villa / 6 Bedrooms / sleeps 14

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

Add to shortlist

from £86 / night

£600 - £700 / week

View

Luxury Disney Villa. Close to Disney, Large 6 bedroom villa, private pool with spa, not overlooked, Florida villa, childrens themed rooms, games room, free wifi, gates resort, gated community, for the perfect family Florida holiday, I can offer my fabulous 6 bedroom villa in the Disney area  …see more

from £58 / night

£400 - £450 / week

View

(1) Very Good 4/5 

1 / 19

Crescent Lakes holiday villa rental

Villa / 4 Bedrooms / sleeps 10

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

Very Good 4/5 

Add to shortlist

from £58 / night

£400 - £450 / week

View

This property is the ideal base for your Dream Florida holiday. The property is larger than average with huge outside areas and fully equipped for your comfort. There is a friendly management company close at hand and pool door alarm for your piece of mind. The property was renovated in late 2012 and now includes free local calls and WiFi for your convenience.  …see more

from £83 / night

£575 - £900 / week

View

(1) Excellent 5/5 

1 / 13

Lake Berkley holiday villa rental

Villa / 5 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £83 / night

£575 - £900 / week

View

Luxury 5 Bedrooms / 3 bathrooms upgraded lakeside villa with private enclosed heated pool overlooking natural Lake. Games room, Free WI-FI, 200+ cable TV with Flat screen in lounge + cable TV in each room. 24 hour security & 10 Minutes from Disney. Fully Air Conditioned  …see more

from £99 / night

£690 - £895 / week

View

(14) Excellent 5/5 

1 / 24

Holiday villa with private swimming pool in Kissimmee

Villa / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £99 / night

£690 - £895 / week

View

*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 £81 / night

£565 - £745 / week

View

(5) Excellent 5/5 

1 / 24

Home rental in Kissimmee

House / 5 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £81 / night

£565 - £745 / week

View

Location, style and space! 5 bedroom, 3 bathroom luxury villa with large private heated/screened pool in the pristine, gated residential resort of Lake Berkley, Kissimmee. Close to all the major theme parks and well served by supermarkets, restaurants and activities. The resort boasts a clubhouse with games room, exercise room, internet access and community swimming pools.  …see more

from £60 / night

£416 - £520 / week

View

(1) Excellent 5/5 

1 / 4

Holiday villa with swimming pool, golf nearby in Kissimmee

Villa / 3 Bedrooms / sleeps 6

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

Excellent 5/5 

Add to shortlist

from £60 / night

£416 - £520 / week

View

Convenient for Disney Theme Park 3 Bedrooms 2 bathrooms - 1 ensuite Screened Un-Heated Pool Fully Fitted Kitchen providing all the amenities Wireless Free Broadband Available  …see more

from £50 / night

£350 - £420 / week

View

(1) Excellent 5/5 

1 / 12

Villa rental in Kissimmee with shared pool, golf nearby

Villa / 3 Bedrooms / sleeps 8

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £50 / night

£350 - £420 / week

View

Spacious 3 bedroom/2 bathroom villa. Minutes from all the Disney attractions. Complimentary use of all complex facilities inc 3 great pools, a gym, floodlit tennis courts and a children's park.  …see more

from £40 / night

£280 - £550 / week

View

(6) Excellent 5/5 

1 / 22

Holiday townhouse with shared pool in Trafalgar Village

Townhouse / 3 Bedrooms / sleeps 6

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

Excellent 5/5 

Add to shortlist

from £40 / night

£280 - £550 / week

View

Florida 3 bed 3 bathroom luxury Townhouse only 20 to 25 mins away from Disney World.  …see more

from £93 / night

£645 / week

View

(2) Excellent 5/5 

1 / 24

Kissimmee holiday villa rental

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £93 / night

£645 / week

View

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 £79 / night

£548 - £655 / week

View

(8) Excellent 5/5 

1 / 25

Villa rental in Kissimmee with swimming pool

Villa / 4 Bedrooms / sleeps 9

  • Nearest beach 45 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £79 / night

£548 - £655 / week

View

Private pool, 10mls Disney, 17mls Universal, Ground Floor Master, Queen Room, Disney Pixar Cars & Sunny Beach Theme twin rooms, twin beds convert to a king bed, Baby Pack, Games Room, Nintendo Wii +4 controllers, PSII, FREE Wi-Fi, calls, cable TV. Full A/C, ceiling Fans Just 10 miles from Mickey's doorstep, 17 miles from Shamu. 2 miles from The Loop and 2 minutes from Wal*Mart  …see more

from £66 / night

£460 - £485 / week

View

(2) Excellent 5/5 

1 / 13

Holiday villa with swimming pool in Kissimmee

Villa / 4 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £66 / night

£460 - £485 / week

View

Florida Villa Rental 4 bed executive villa with private 30ft.swimming pool with spa backing onto a conservation area.Situated on Indian point a quiet residential community.  …see more

from £58 / night

£400 - £500 / week

View

(3) Excellent 5/5 

1 / 24

Holiday villa in Kissimmee

Villa / 4 Bedrooms / sleeps 8

  • Nearest beach 12 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £58 / night

£400 - £500 / week

View

Forida Villa Close to airport, close to disney, close to seaworld, close to universal studios, lake view, great to chill, late checkout available. see the real Florida  …see more

from £65 / night

£450 / week

View

(2) Very Good 4/5 

1 / 10

Kissimmee holiday villa accommodation

Villa / 4 Bedrooms / sleeps 9

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

Very Good 4/5 

Add to shortlist

from £65 / night

£450 / week

View

Executive style four bedroom, two bathroom Villa in Kissimmee. Very close to Disney and Universal theme parks. Private garden, with heated pool and Jacuzzi.  …see more

from £98 / night

£685 - £845 / week

View

(2) Excellent 5/5 

1 / 24

Holiday villa letting

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £98 / night

£685 - £845 / week

View

4 bed villa near Disney, FREE wifi, private pool and jacuzzi,air con, 2 bathrooms, 220 channel hdtv's, PS3, Xbox360, Windsor Palms Resort, secure gated community with communal pool, tiki bar, playground, sports courts, gym, games room, cinema, shop, bike/dvd/bbq rentals More info on our villa, Windsor Palms Resort and Florida attractions on lawrencevacationhomes website  …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