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 (10)
  • Calabria, Orlando (2)
  • Cane Island (2)
  • Chatham Park (1)
  • Compass Bay (4)
  • Coral Cay (2)
  • Country Creek (1)
  • Creekside (1)
  • Crescent Lakes (12)
  • Crestwynd Bay (4)
  • Cumbrian Lakes (20)
  • Doral Woods (7)
  • Eagle Pointe (5)
  • Emerald Isle Kissimmee (44)
  • Encantada Resort (4)
  • Fiesta Key (3)
  • Formosa Gardens (10)
  • Hamilton's Reserve (1)
  • Indian Creek (12)
  • Indian Ridge (4)
  • Indian Ridge Oaks (3)
  • Kissimmee City (11)
  • Lake Berkley (21)
  • Lake Marion (1)
  • Legacy Dunes Resort (3)
  • Liberty Village (3)
  • Lindfields (11)
  • Oak Island Cove (7)
  • Oak Island Harbor (3)
  • Orange Lake Resort (5)
  • Paradise Palms (7)
  • Regal Oaks (3)
  • Remington (3)
  • Rolling Hills at Formosa (1)
  • Seasons Resort (10)
  • Sunset Lakes (6)
  • Terra Verde Resort (9)
  • The Hamlets (1)
  • Trafalgar Village (1)
  • Tuscany, Florida (3)
  • Venetian Bay Villages (11)
  • Veranda Palms (5)
  • Villasol (1)
  • Vista del lago (2)
  • Westside (2)
  • Windsor Hills Resort (15)
  • Windsor Palms (16)
  • 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

Filters applied: Heated pool (448)

32 of 448 Results

Sort by: Default

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

from £64 / night

£447 - £564 / week

View

(2) Very Good 4.5/5 

1 / 19

Holiday villa in Kissimmee

Villa / 3 Bedrooms / sleeps 6

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4.5/5 

Add to shortlist

from £64 / night

£447 - £564 / week

View

Great home for families! Luxurious spacious villa, completely private heated pool, very comfortable beds, fully equipped kitchen, digital HDTV, PS2s & free Wi-Fi. Ideal location, just 10 - 15 minutes to Disney, 1 min drive to 24hr WalMart & US192 for dining, bars etc.. Ideally located for all the major attractions, but on a safe, quiet, estate away from the main roads.  …see more

from £100 / night

£700 - £840 / week

View

(13) Excellent 5/5 

1 / 24

Villa rental in Sunset Lakes

Villa / 4 Bedrooms / sleeps 10

  • Beach / lakeside relaxation
  • Nearest beach 104 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £100 / night

£700 - £840 / week

View

'The Retreat' Villa at Sunset Lakes is a beautfiful 4 bedroom (sleeps upto 10) 3.5 bathroom occupying a prized lakefront location in the quiet gated community of Sunset Lakes just 4 miles from the magical gates of Disney.  …see more

from £78 / night

£540 - £790 / week

View

(3) Excellent 5/5 

1 / 20

Holiday townhouse in Kissimmee

Townhouse / 4 Bedrooms / sleeps 10

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £78 / night

£540 - £790 / week

View

A Beautiful 5* Star 'Spacious', 4 bedroom, 3 bath Vacation home, south Facing Private Pool on a holiday resort with Communal Pool, tennis Courts, Games Room, Sauna, Gym, Card Room. Tiki Bar. 5 Mins from Disney and all the major attractions. Ideal for families & Golfers Our Home is fully equipped with every thing you would need for your holiday and more.  …see more

Featured properties

from £200 / night

£1400 - £2240 / week

View

(8) Very Good 4.5/5 

1 / 20

Holiday villa with indoor pool in Paradise Palms

Villa / 6 Bedrooms / sleeps 12

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

Very Good 4.5/5 

Add to shortlist

from £200 / night

£1400 - £2240 / week

View

This beautiful vacation Home community is just minutes from Disney World. Featuring the very best resort amenities including the 5,000 sq ft pool, luxurious spas, Tiki bar. movie theatre, games room, basketball and volleyball courts, lighted tennis courts and much more!  …see more

from £110 / night

£770 - £1120 / week

View

(16) Excellent 5/5 

1 / 20

Villa rental in Kissimmee

Villa / 5 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £110 / night

£770 - £1120 / week

View

Luxury 5 bedroom home with screened pool and spa, on a large corner lot overlooking woodland - no house behind just open space, walking distance to clubhouse. Conveniently situated in a peaceful gated community of Emerald Isle, only 3 miles from disney. Please read the reviews for this property. Our goal is to ensure your holiday is comfortable and stress free  …see more

from £60 / night

£420 - £500 / week

View

(8) Very Good 4/5 

1 / 17

Kissimmee holiday villa rental

Villa / 3 Bedrooms / sleeps 6

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

Very Good 4/5 

Add to shortlist

from £60 / night

£420 - £500 / week

View

Executive 3bed/2 bath villa with private pool.Located on one of the most popular rental areas close to all the attractions with Disney just 8 minutes away. Ideal for families & Perfect for Golfers with many courses within 5 minutes drive.  …see more

from £68 / night

£473 - £845 / week

View

(6) Excellent 5/5 

1 / 24

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 £68 / night

£473 - £845 / week

View

Gated Resort Villa in Emerald Isle Resort. Newly refurbished Living area Private Pool Resort Gym/Sauna/Steam room Close to Disney FREE long distance to calls anywhere in the US & Canada. WiFi  …see more

from £85 / night

£592 - £744 / week

View

(11) Very Good 4.5/5 

1 / 22

Holiday home in Cumbrian Lakes

House / 5 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 £85 / night

£592 - £744 / week

View

Beautiful 2 storey executive villa in the sought after gated community of Cambrian Lakes 12 minutes from Disney. 5 bedrooms and 3.5 bathrooms. High class furnishings and a large master bedroom with en-suite. Private pool games room, free WiFi, computer, etc...  …see more

from £68 / night

£475 - £560 / week

View

(12) Excellent 5/5 

1 / 24

Kissimmee holiday villa rental

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 £68 / night

£475 - £560 / week

View

Our home is a luxury 4-bedroom, 3-bathroom home with its own private screened pool centrally located for all the theme parks, shopping outlets and restaurants yet situated in a small and peaceful gated community. Luxury Vacation Villa situated on an exclusive gated community, FREE POOL HEATING AND Wi-Fi, GAMES ROOM.  …see more

from £72 / night

£499 - £610 / week

View

(4) Excellent 5/5 

1 / 18

Villa rental in Kissimmee with shared pool

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £72 / night

£499 - £610 / week

View

Free WiFi / Free International Calls. Lovely 4-bed pool home with jacuzzi/hot-tub. Close to Walt Disney World and universal studios. Perfect for families and golfers alike.  …see more

from £78 / night

£541 - £642 / week

View

(1) Excellent 5/5 

1 / 17

Holiday home with indoor pool in Terra Verde Resort

House / 5 Bedrooms / sleeps 10

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £78 / night

£541 - £642 / week

View

Five bedroom house, gorgeous heated pool, games room, in Kissimmee, just a few miles for the Disney complex. The house is located in an excellent Resort which provides concierge 24 hours. Parking: Free parking lot in front of the house  …see more

Pricing unknown

View

(2) Excellent 5/5 

1 / 20

Lake Berkley holiday villa rental

Villa / 6 Bedrooms / sleeps 14

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

Excellent 5/5 

Add to shortlist

Pricing unknown

View

6 Bedroom Villa, 3 Master Bedrooms, Completely Private Pool and Spa Overlooking the Lake, Brand New Games Room, Golf Clubs, Wi Fi, Sat Nav, Fishing Rods, 10 Minutes To Disney 24hr Gated Security Guarded Community With Gym, Tennis Court, Basketball, Fishing, Nature Trails And More..  …see more

from £72 / night

£500 - £600 / week

View

(2) Very Good 4/5 

1 / 20

Holiday villa with shared pool, golf nearby in Kissimmee

Villa / 5 Bedrooms / sleeps 12

  • Nearest beach 96 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4/5 

Add to shortlist

from £72 / night

£500 - £600 / week

View

A beautifully appointed 5 bedroom, 3 bath luxury family vacation home provides state of the art living, comfort and freedom that cannot be found in a hotel room. Accommodating up to 12 people. On a first class gated community. Villa sol is maintained to a very high standard a gymnasium pool and sports activities are available .  …see more

from £76 / night

£527 - £605 / week

View

(21) Very Good 4/5 

1 / 20

Kissimmee holiday villa accommodation

Villa / 4 Bedrooms / sleeps 10

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4/5 

Add to shortlist

from £76 / night

£527 - £605 / week

View

Holiday Villa with Pool Villas in Florida Holiday Home Near theme parks Florida Villas Private owned home with Pool  …see more

from £180 / night

£1260 - £1785 / week

View

(11) Excellent 5/5 

1 / 21

Holiday villa with golf nearby in Kissimmee

Villa / 6 Bedrooms / sleeps 12

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

Excellent 5/5 

Add to shortlist

from £180 / night

£1260 - £1785 / week

View

Luxury 6 bedroom private villa with private pool, games room in the world renowned gated community of Windsor Hills Resort just 2 miles from the gated of Walt Disney World in Kissimmee, Orllando Florida  …see more

from £82 / night

£568 - £923 / week

View

(1) Excellent 5/5 

1 / 59

Holiday home in Kissimmee

House / 4 Bedrooms / sleeps 12

  • Nearest beach 103 km
  • Swimming pool
  • Not suitable for children
  • Car advised

Excellent 5/5 

Add to shortlist

from £82 / night

£568 - £923 / week

View

A casa fica no Condomínio Paradise Palms, o condomínio preferido dos Brasileiros em Orlando! Alugue na Disney!!!  …see more

from £61 / night

£425 - £675 / week

View

(25) Excellent 5/5 

1 / 24

Villa rental in Kissimmee

Villa / 4 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £61 / night

£425 - £675 / week

View

Pure Luxury - Stunning Pool - Great Games Room - Top Location - Unbelievable Price!!!  …see more

from £68 / night

£475 - £550 / week

View

(9) Excellent 5/5 

1 / 24

Kissimmee holiday villa rental

Villa / 4 Bedrooms / sleeps 8

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £68 / night

£475 - £550 / week

View

Very close to Walt Disney World, just 10 mins (homes in Davenport quote 15 mins but its more 30 mins). Nearby there is an abundance of restaurants and gift stores as well as supermarkets. Excellent location for moving around Florida with easy access to the freeways. Clean linens, bedding, hand and bath towels are included in the cost of the rental of the property  …see more

from £244 / night

£1707 - £2090 / week

View

(51) Excellent 5/5 

1 / 20

Holiday villa with golf nearby in Kissimmee

Villa / 7 Bedrooms / sleeps 19

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £244 / night

£1707 - £2090 / week

View

" This really is the classiest of them all " Winner of the Best Kissimmee Vacation Rental Home 2011 & 2012, and Rated Excellent, and Recommended by Trip Advisor. Exceptionally luxurious 7 bed, 6 baths, sleeps 16, South Facing, Lake View, Formosa Gardens Villa. Florida Vacation Home,10 minutes from Disney,take a look at the outstanding features this Holiday Home has.  …see more

from £36 / night

£246 - £343 / week

View

(11) Excellent 5/5 

1 / 18

Kissimmee holiday townhouse rental

Townhouse / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £36 / night

£246 - £343 / week

View

Affordable 3 bedroom townhouse on a gated community with many amenities just 15 minutes from Disney. 3 bedroom townhouse on gated community with many amenities.  …see more

from £111 / night

£774 - £1033 / week

View

(3) Excellent 5/5 

1 / 16

Holiday villa in Kissimmee

Villa / 5 Bedrooms / sleeps 10

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

Excellent 5/5 

Add to shortlist

from £111 / night

£774 - £1033 / week

View

Santa Caterina is located in the beautiful Windsor Hills Resort where you can enjoy all the comforts and amenities of home with all the attractions and the social interactions of a First Class Resort.  …see more

from £180 / night

£1260 - £1680 / week

View

(8) Excellent 5/5 

1 / 18

Holiday villa with golf nearby in Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

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

Excellent 5/5 

Add to shortlist

from £180 / night

£1260 - £1680 / week

View

Luxury pool villa home with 6 bedroom, 4 bathroom, games room in a world renowned gated community of Windsor Hills resort. Located just 2 miles from the front gates of Walt Disneyland Orlando, Florida.  …see more

from £65 / night

£450 - £750 / week

View

(6) Excellent 5/5 

1 / 17

Kissimmee 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 £65 / night

£450 - £750 / week

View

Live the American dream in your very own Florida holiday home located in the quiet gated community of The Hamlets. Just off highway 192 in Kissimmee, yet only minutes drive to hundreds of shops & restaurants (some are even within walking distance) and close to Disney. Our home has 5 beds. 3 baths, south facing pool & spa and games room.  …see more

from £173 / night

£1207 - £2129 / week

View

(2) Excellent 5/5 

1 / 24

Holiday home rental

House / 7 Bedrooms / sleeps 16

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £173 / night

£1207 - £2129 / week

View

Theater room, lake view, South facing pool & spa, pool table, free internet, free local calls. Luxurious 5 star, 7 bedroom home has it all. Professionally decorated to a very high standard, the perfect vacation home. One of the best. 2 luxury master suites, 2 designer Queen bedrooms, 3 kids rooms, Cars, Disney Fairies & Mickey Mouse .  …see more

from £79 / night

£550 - £750 / week

View

(1) Excellent 5/5 

1 / 16

Holiday villa in Lake Berkley

Villa / 4 Bedrooms / sleeps 8

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £79 / night

£550 - £750 / week

View

Luxury Lakeside Villa with own pool/spa. 10 mins to Disney. Free high speed internet access. 37" wide screen TV. Free high speed internet access. TVs in every bedroom. Fully air conditioned. Pay by credit card or cheque. The villa is situated within Lake Berkley Resort, Kissimmee, a safe, secure gated community.  …see more

from £75 / night

£525 - £700 / week

View

(1) Excellent 5/5 

1 / 16

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 £75 / night

£525 - £700 / week

View

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 £114 / night

£795 - £1095 / week

View

(1) Excellent 5/5 

1 / 24

Holiday villa in Seasons Resort

Villa / 6 Bedrooms / sleeps 12

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

Excellent 5/5 

Add to shortlist

from £114 / night

£795 - £1095 / week

View

A stylish Orlando escape. This fabulous two-storey villa has everything your family could need for a dream vacation in the Florida sunshine. Enjoy the wonderful, sparkling pool overlooking the attractive lake, plus, it has a great location; close to all the attractions  …see more

from £79 / night

£550 - £800 / week

View

(3) Excellent 5/5 

1 / 21

Holiday villa with golf nearby in Indian Creek

Villa / 5 Bedrooms / sleeps 12

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

Excellent 5/5 

Add to shortlist

from £79 / night

£550 - £800 / week

View

This 5 Bedroom villa is situated right on Mickeys doorstep on popular Indian Creek community, approximately 2.5 miles from Disney. Large private pool with decking overlooking conservation area, games room. Large selection of restaurants, supermarkets, gift shops nearby. 2.5 miles to Disney, Games room, Large pool and decking overlooking coservation area, near to all ameanities  …see more

from £60 / night

£419 - £560 / week

View

1 / 14

Kissimmee holiday condo rental

Condo / 3 Bedrooms / sleeps 6

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

Add to shortlist

from £60 / night

£419 - £560 / week

View

Apartamento de 3 quartos, 2 banheiros, sala de estar e jantar, cozinha, lavanderia, A/C e aquecedor centrais. Wi-Fi, telefone e TV. Clube com piscina aquecida, sauna, academia, quadra de tênis, etc. Localização excelente. 10 minutos da Disney e do Premium Outlet. Taxa única de limpeza: U$ 80.00 Taxa de proteção à propriedade: U$ 65.00 (pagamento no check in).  …see more

from £50 / night

£350 - £395 / week

View

(12) Excellent 5/5 

1 / 24

Holiday villa in Kissimmee

Villa / 3 Bedrooms / sleeps 8

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

Excellent 5/5 

Add to shortlist

from £50 / night

£350 - £395 / week

View

Luxury 3 bed villa sleeps 8. Large 30ft fully heated secluded pool. 15mins.drive from Disney. Surrounded by beautiful golf courses  …see more

from £93 / night

£650 - £750 / week

View

(13) Excellent 5/5 

1 / 24

Villa rental in Cumbrian Lakes

Villa / 5 Bedrooms / sleeps 12

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

Excellent 5/5 

Add to shortlist

from £93 / night

£650 - £750 / week

View

Welcome to Robson's Retreat villa in Florida, our home is a beautiful 2 storey home with approximately 2,500 square foot of living space. As you enter our home Mickey and Minnie are there to welcome you to Florida and to their home. Welcome to Robson's Retreat, a fully equipped 5 bedroom home which will be perfect for your Florida holiday.  …see more

from £52 / night

£360 - £450 / week

View

(13) Very Good 4.5/5 

1 / 24

Villa rental in Kissimmee

Villa / 3 Bedrooms / sleeps 8

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages

Very Good 4.5/5 

Add to shortlist

from £52 / night

£360 - £450 / week

View

Our beautiful family owned 3 bedroom, 2 bathroom villa has everything for a great family vacation and is ideally located close to the Parks, and surrounding area. It has a heated pool and games room, is fully air-conditioned and superbly equipped for up to 8 people. Just 2 mins to shops & restaurants, 10 mins to Disney, 20 mins to Universal & 10 mins to Kissimmee Golf Club  …see more

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