List your home
Apply filters
£ to

50 Holiday homes near Crestwynd Bay

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
  • Windsor Hills Resort Clear

Location

  • All locations

more +

less -

Property type

more +

less -

Activities

more +

less -

Suitability

more +

less -

Facilities

more +

less -

Filters applied: Nightlife (0)

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
50 Results   |  

More results near Crestwynd Bay

from £109 / night

£760 - £1000 / week

View

Excellent 5/5 

19 Photos

Distance approx 0.35 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

Villa / 5 Bedrooms / sleeps 14

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £109 / night

£760 - £1000 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 64 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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 £141 / night

£985 - £1550 / week

View

Excellent 5/5 

24 Photos

Distance approx 0.64 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee with golf nearby

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 14

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £141 / night

£985 - £1550 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
New 2010 Luxury 5 Star, South facing 6 Bed 4 bath Villa. 2 Miles from Dsney. Free calls, Loc, national & international, Free WiFi. Private heated Pool & Spa. Tvs in all rms. Your own games Rm with 42" Lcd & Xbox 360, air hockey, pool tab, foosball & electronic darts. Free Club house with Pool/Jacuzzi , Free tennis courts, Putting green, Basket ball & BBQ area, water slides  …see more

from £180 / night

£1260 - £1855 / week

View

Excellent 5/5 

21 Photos

Distance approx 0.67 miles from Crestwynd Bay   |  Show on Map

Holiday villa with golf nearby in Kissimmee

Kissimmee / Windsor Hills Resort

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £180 / night

£1260 - £1855 / week

View

Key info:

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

Featured properties

from £244 / night

£1706 - £2642 / week

View

Excellent 5/5 

27 Photos

Distance approx 0.81 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Formosa Gardens

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £244 / night

£1706 - £2642 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Spacious 3400 ft, 6 bedoomed home, non smoking, sleeps 12, free wifi,games room,south facing swimming pool,secluded large corner plot. Free wifi, 6 bedrooms,south facing pool, secluded large corner plot , very comfortable home, games room.  …see more

from £529 / night

£3700 / week

View

Excellent 5/5 

20 Photos

Distance approx 1 miles from Crestwynd Bay   |  Show on Map

Holiday villa in Kissimmee

Kissimmee / Formosa Gardens

Villa / 7 Bedrooms / sleeps 16

Excellent 5/5 

1 night min stay

Add to shortlist

from £529 / night

£3700 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Getaway is a unique luxury villa located within 10 minutes of Disneyworld and features 3 lounges, 7 bedrooms, 12 person home theatre, gym, huge private pool & outdoor kitchen with living space. At over 6500sq ft our home caters for even the largest of groups. Completely refurbished in 2010 The Getaway offers 'brand new everything' with luxury furnishings throughout  …see more

from £246 / night

£1716 - £2226 / week

View

24 Photos

Distance approx 1.1 miles from Crestwynd Bay   |  Show on Map

Holiday home with golf nearby in Kissimmee

Kissimmee / Indian Creek

House / 5 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £246 / night

£1716 - £2226 / 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

from £122 / night

£850 / week

View

24 Photos

Distance approx 1.12 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee

Kissimmee / Indian Creek

Villa / 5 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £122 / night

£850 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Located 5- 10 mins away from Disney theme parks. Easy access to all parks private pool & lounge spa  …see more

from £100 / night

£700 - £900 / week

View

Excellent 5/5 

19 Photos

Distance approx 1.14 miles from Crestwynd Bay   |  Show on Map

Holiday villa with golf nearby in Davenport

Davenport / Hampton Lakes

Villa / 5 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £100 / night

£700 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury & Spacious 3215 sq foot villa with extra large 30' x 15' South Facing Private Pool, huge deck with shaded area, separate hydrotherapy hot tub/spa. Professional Games Room , Digital cable T.V., Wifi. Sleeps up to 12. Prestigious Community. 5* TRIPADVISOR. Walts World has 3215 Sq Ft, situated on Hampton Lakes, only minutes to Disney/Universal, 3 minutes to the I4  …see more

from £93 / night

£645 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.23 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday villa rental

Kissimmee / Oak Island Cove

Villa / 4 Bedrooms / sleeps 10

Excellent 5/5 

Short stays welcome

Add to shortlist

from £93 / night

£645 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
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 £100 / night

£700 - £875 / week

View

Very Good 4/5 

24 Photos

Distance approx 1.28 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee with golf nearby

Kissimmee / Oak Island Cove

Villa / 6 Bedrooms / sleeps 13

Very Good 4/5 

Min stay varies

Add to shortlist

from £100 / night

£700 - £875 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A lifetime of memories in our fantastic and luxurious 6 bedroom villa located in Oak Island Cove, Kissimmee, Florida, just 5 minutes from Disney. This memorable, yet affordable house comprises two floors of comfort and elegance. Our home we enjoy and love. It's where we spend our vacation time relaxing and enjoying Florida sunshine.  …see more

from £58 / night

£400 - £575 / week

View

Very Good 4.5/5 

17 Photos

Distance approx 1.34 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee

Kissimmee / Oak Island Harbor

Villa / 4 Bedrooms / sleeps 8

Very Good 4.5/5 

Min stay varies

Add to shortlist

from £58 / night

£400 - £575 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Fabulous vacation home sleeps 8 in comfort with lake views and a south facing pool with spa. Oak Island Harbor subdivision is part of the Formosa Gardens estate and is minutes from Disney. Quality fittings, wi-fi, and HD TV will make your vacation one to remember. Pool-side toilet and outside shower.  …see more

from £93 / night

£650 - £900 / week

View

Excellent 5/5 

23 Photos

Distance approx 1.36 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Windsor Palms

House / 4 Bedrooms / sleeps 10

Excellent 5/5 

Min stay varies

Add to shortlist

from £93 / night

£650 - £900 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Welcome to Mickey's Clubhouse. Our beautiful 4 bed 3 bath villa is located on the gated 5 * community of Windsor Palms, only three miles from Disney. It has all the comforts you could wish for including a private south facing pool. Complimentary use of Windsor Palms amenities including: Cinema, Spa, Gym, Olympic size pool & Playground.  …see more

from £35 / night

£245 - £320 / week

View

Excellent 5/5 

17 Photos

Distance approx 1.38 miles from Crestwynd Bay   |  Show on Map

Holiday condo with golf nearby in Kissimmee

Central Florida / Kissimmee

Condo / 3 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £35 / night

£245 - £320 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
A Luxury, 3 bedroom condo located in the Windsor Palms Resort, Our Spacious and Fully furnished Apartment is minutes from Disney, and boasts superb on site amenities including, It makes the perfect location for your vacation. Free WIFI available in the condo.  …see more

from £95 / night

£663 - £828 / week

View

23 Photos

Distance approx 1.42 miles from Crestwynd Bay   |  Show on Map

Orlando holiday villa rental

Central Florida / Orlando

Villa / 6 Bedrooms / sleeps 13

4 Nights min stay

Add to shortlist

from £95 / night

£663 - £828 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Villa Joya is located in a beautiful Oak Island Cove community,The location is ideal with only a short distance to the 192 corridor and 3 miles to Disney world parks Driving distance of 20 minutes to UNIVERSAL PARKS ,.DISCOVERY COVE SEA WORLD Nearby to shopping centers  …see more

from £54 / night

£375 - £675 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.45 miles from Crestwynd Bay   |  Show on Map

Holiday condo with golf nearby in Kissimmee

Kissimmee / Windsor Palms

Condo / 3 Bedrooms / sleeps 7

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £54 / night

£375 - £675 / week

View

Key info:

  • Nearest beach 117 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Luxury Condo on Disney's doorstep in gated community of Windsor Palms with superb facilities on site including Large heated pool, hot tub, 3D cinema, Tikki Bar and Gym. Ideal for families, couples or groups of friends. Accommodates upto 7 plus pack and play crib Late deals ask for prices. Monthly prices from £1,200 including taxes  …see more

from £66 / night

£457 - £597 / week

View

24 Photos

Distance approx 1.5 miles from Crestwynd Bay   |  Show on Map

Townhouse rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

Townhouse / 3 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £66 / night

£457 - £597 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
A luxurious 3 bedroom / 2.5 bath townhouse that sleeps up to 8 is fully air conditioned and very well equipped including TVs and DVD players in all bedrooms, a PS2 games console for the kids, wireless internet access, free local & national telephone call and more.. Why stay anwhere else when you can get all this within 5 minutes (3 miles) of Disney World Orlando Florida?  …see more

from £88 / night

£610 - £725 / week

View

Excellent 5/5 

23 Photos

Distance approx 1.5 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday villa rental

Kissimmee / Windsor Palms

Villa / 4 Bedrooms / sleeps 9

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £88 / night

£610 - £725 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Disney Paradise is a magnificent 4 bedroom, 3 bathroom pool home is in the 5 star Windsor Palms Resort. Luxurious accommodation and pool with spa PLUS complimentary membership to Windsor Palms 5 star facilities. Check out the welcome video http://youtu.be/VgdS6BbxMHw  …see more

from £229 / night

£1600 - £1971 / week

View

44 Photos

Distance approx 1.51 miles from Crestwynd Bay   |  Show on Map

Holiday home with golf nearby in Orlando

Central Florida / Orlando

House / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £229 / night

£1600 - £1971 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Gorgeous Home with Lots of Disney Flair. 3 Kings, 2 Great Kids Theme Rooms, Private Pool, Spa, WiFi, Large Screen TV, Game Room, Wii Game System, Full Gourmet Kitchen and lots of upgrades to enhance your stay.  …see more

from £83 / night

£576 - £987 / week

View

Very Good 4.5/5 

27 Photos

Distance approx 1.54 miles from Crestwynd Bay   |  Show on Map

Holiday villa in Kissimmee

Kissimmee / Windsor Palms

Villa / 4 Bedrooms / sleeps 8

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £83 / night

£576 - £987 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Family accommodation near Orlando. Self-catering accommodation in Florida. Holiday Home near Disney. Disney Dream Villa. Orlando villa with pool Prime location near Disney, also near to local amenities. Private pool/spa in a secure location. Games Room  …see more

from £147 / night

£1025 - £1637 / week

View

24 Photos

Distance approx 1.63 miles from Crestwynd Bay   |  Show on Map

Home rental in Kissimmee with shared pool, golf nearby

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £147 / night

£1025 - £1637 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Night Life -Double Bed - King Bed - Queen Bed - Internet Connection - Telephone - Cable/Satellite - Multiple TV's - Gaming Console - Internet Connection - Linens Provided - Non Smoking - Coffeemaker - Gas Grill- Patio - Coffeemaker - Gas Grill Living Area: 2,890 SqFt - - Lot Size: 4,250 SqFt  …see more

from £68 / night

£475 - £675 / week

View

6 Photos

Distance approx 1.63 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee with golf nearby

Kissimmee / Indian Ridge

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £68 / night

£475 - £675 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Luxury 4 bedroom villa with south facing pool and spa. Air conditioned throughout, great location just 5 minutes from Walt Disney World. Indian Ridge is a quiet residential community, yet just minutes from theme parks, shops and restaurants  …see more

from £83 / night

£580 - £1016 / week

View

Very Good 4/5 

20 Photos

Distance approx 1.79 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday villa rental

Kissimmee / Windsor Hills Resort

Villa / 4 Bedrooms / sleeps 8

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £83 / night

£580 - £1016 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A 4 bedroom luxury Villa, with pool,spa and games room at the prestigious Windsor Hills community, within 2 Miles of Walt Disney World. Windsor Hills has a five star clubhouse with Lagoon Pool, hot tub, slides, Cinema, Gym, Games Room, Shop & “Castle” play area.  …see more

from £78 / night

£545 - £660 / week

View

Excellent 5/5 

20 Photos

Distance approx 1.82 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee

Kissimmee / Indian Ridge

Villa / 3 Bedrooms / sleeps 6

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £78 / night

£545 - £660 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
3 bedroom/2 bath spacious villa, West Kissimmee, countryside estate Indian Ridge 3 miles south of Disney South facing solar/gas heated pool Private secluded fenced garden Family room and living room 5 HDTVs, 70+ dvds 24/7 security system Security safe Child equipment 3 miles to Disney - south facing solar heated pool - 3 bedroom/2 bathroom Key are located at the property  …see more

from £72 / night

£500 - £625 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.85 miles from Crestwynd Bay   |  Show on Map

Holiday villa with swimming pool in Kissimmee

Kissimmee / Indian Ridge

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £72 / night

£500 - £625 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Indian Ridge 4 bed Luxury Villa 4 Miles From Disney Our spacious fully furnished, four bedroom, two bathroom Games room villa is located in the residential sub division of Indian Ridge just 4 miles southwest of the Walt Disney World Resort entrance.  …see more

from £110 / night

£770 - £1120 / week

View

Excellent 5/5 

20 Photos

Distance approx 1.86 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee

Kissimmee / Emerald Isle Kissimmee

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £110 / night

£770 - £1120 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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 £67 / night

£464 - £812 / week

View

Excellent 5/5 

24 Photos

Distance approx 1.98 miles from Crestwynd Bay   |  Show on Map

Home rental in Kissimmee with indoor pool

Kissimmee / Emerald Isle Kissimmee

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £67 / night

£464 - £812 / week

View

Key info:

  • Nearest beach 96 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
COMFORTABLE 4 BED/ 3 BATH HOUSE WITH HEATED POOL AND SPA, GAMES ROOM WITH AIRHOCKEY E GAMES ARCADE, 3 MILES TO PARKS, FREE WI-FI, CABLE TV AND A FULL RESORT WITH SWIMMING POOL, TIKI BAR, FITNESS ROOM, COMPUTERS WITH WI-FI, TENNIS COURT, TRAILS AND BEAUTIFUL GARDENS. PAY LESS THAN A HOTEL AND HAVE MORE COMFORT AND PRIVACE WITH A BIG HOUSE, RENEWED IN NOV. WITH WOODEN FLOOR.  …see more

from £96 / night

£670 - £990 / week

View

Excellent 5/5 

24 Photos

Distance approx 2.04 miles from Crestwynd Bay   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

1 night min stay

Add to shortlist

from £96 / night

£670 - £990 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 130 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Located 3 miles from Disney World main gate, and easy reach of all Orlando attractions. Sleeps 8; comprising of 4 bedrooms, (2 en-suites) and 3 full bathrooms. . Private south facing heated pool and spa + games room and free Wi-Fi, Flat screen TV's in all bedrooms.  …see more

from £128 / night

£895 - £1195 / week

View

20 Photos

Distance approx 2.05 miles from Crestwynd Bay   |  Show on Map

Holiday villa in Kissimmee

Kissimmee / Emerald Isle Kissimmee

Villa / 6 Bedrooms / sleeps 13

3 Nights min stay

Add to shortlist

from £128 / night

£895 - £1195 / week

View

Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This quality ,luxury 6 bed, 4.5 bath villa sleeps 12(plus infant) over 3,000sq.ft.of luxury and has its own 30 ft pool with spa. Features such as;Premium TV Package, Games room, Nintendo wii,, Playstation 2,wifi etc Family Friendly, 6 Bed, 4.5 bath Villa with Oversize South facing Pool and Spa, 3miles to WDW  …see more

from £169 / night

£1183 - £2087 / week

View

Excellent 5/5 

24 Photos

Distance approx 2.17 miles from Crestwynd Bay   |  Show on Map

Holiday home rental

Kissimmee / Emerald Isle Kissimmee

House / 7 Bedrooms / sleeps 16

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £169 / night

£1183 - £2087 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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 £169 / night

£1183 - £2087 / week

View

Excellent 5/5 

20 Photos

Distance approx 2.17 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday home let

Kissimmee / Emerald Isle Kissimmee

House / 7 Bedrooms / sleeps 16

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £169 / night

£1183 - £2087 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Theater room, lake view, South facing pool & spa, pool table, free internet, free local calls. Our luxurious 5star, 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, Toy Story, Disney Princess & Mickey Mouse .  …see more

from £123 / night

£858 - £1113 / week

View

15 Photos

Distance approx 2.29 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday villa accommodation

Kissimmee / Emerald Isle Kissimmee

Villa / 4 Bedrooms / sleeps 8

4 Nights min stay

Add to shortlist

from £123 / night

£858 - £1113 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Minutes from Disney, emerald island resort, 4 bed, not overlooked, private heated pool & spa, 3 bath, games area, free broadband, resort facilities.  …see more

from £122 / night

£850 - £1200 / week

View

Excellent 5/5 

24 Photos

Distance approx 2.33 miles from Crestwynd Bay   |  Show on Map

Holiday home in Kissimmee

Kissimmee / Emerald Isle Kissimmee

House / 6 Bedrooms / sleeps 12

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £122 / night

£850 - £1200 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This beautifully furnished, air-conditioned executive home is at Emerald Island Resort, the nearest gated community to Disney. With 6 bedrooms, all with TVs, 4 masters with en suites, and 5.5 bathrooms will sleep up to 12 people in spacious, elegantly furnished style. Close to shops and many restaurants  …see more

from £112 / night

£784 - £1257 / week

View

24 Photos

Distance approx 2.53 miles from Crestwynd Bay   |  Show on Map

Home rental in Kissimmee

Central Florida / Kissimmee

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £112 / night

£784 - £1257 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Internet Connection – Telephone - Cable/Satellite - Multiple TV's - Linens Provided – Coffeemaker - Gas Grill Living Area: 1,940 SqFt -Lot Size: 2,365 SqFt  …see more

from £61 / night

£425 - £500 / week

View

Excellent 5/5 

24 Photos

Distance approx 2.66 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday home rental

Kissimmee / Lindfields

House / 4 Bedrooms / sleeps 8

Excellent 5/5 

Short stays welcome

Add to shortlist

from £61 / night

£425 - £500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Our beautiful villa is located on a small exclusive development with landscaped surroundings and small lakes set in a wooded conservation area. Perfect for the person wanting to relax in quiet idyllic comfort and just 4 miles from Disney World. We maintain our villa to a very high standard inside and out, it really is home from home.  …see more

from £110 / night

£770 - £970 / week

View

Excellent 5/5 

28 Photos

Distance approx 2.7 miles from Crestwynd Bay   |  Show on Map

Holiday villa with golf nearby in Kissimmee

Kissimmee / Sunset Lakes

Villa / 5 Bedrooms / sleeps 12

Excellent 5/5 

1 night min stay

Add to shortlist

from £110 / night

£770 - £970 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
5 Bed, 3.5 Bath ~ Fabulous Vacation Home ~ Sleeps 12 guests + Infants Just 5 mins drive from Walt Disney Private South Facing Pool with Beautiful Lake View ~ Quiet Location Yet Close To Amenities Bright, Modern Villa in a Great Location Great for Families/group A bright, modern and spacious villa. Beautiful decor with everything you could possibly need in a home  …see more

from £65 / night

£455 - £525 / week

View

Excellent 5/5 

12 Photos

Distance approx 2.73 miles from Crestwynd Bay   |  Show on Map

Holiday villa with golf nearby in Kissimmee

Kissimmee / Lindfields

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £65 / night

£455 - £525 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury 4 bedroom 3 bathroom villa with private solar heated pool and hot tub within 5 minutes of Disney. Fully furnished and air conditioned with a full well supplied kitchen. Recently refurbished and decorated. Close to all the restaurants and attractions on hwy 192. Our beautiful home is in Lindfields a prestigious comunity within 5 minutes of Disney.  …see more

from £66 / night

£460 - £600 / week

View

Excellent 5/5 

19 Photos

Distance approx 2.81 miles from Crestwynd Bay   |  Show on Map

Holiday villa in Kissimmee

Kissimmee / Lindfields

Villa / 3 Bedrooms / sleeps 6

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £66 / night

£460 - £600 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Family room has cable tv, dvd, cd, radio, computer with wi-fi access, lots of books for adults and children. Master bedroom has a king size bed and a Hollywood style bathroom. Two other bedrooms - one king and one twin - share a second bathroom. A/C. Huge private pool Great golfing nearby - and lots of good shopping outlets . Guidebooks and maps in the villa to help you.  …see more

from £114 / night

£795 / week

View

11 Photos

Distance approx 2.9 miles from Crestwynd Bay   |  Show on Map

Villa letting in Kissimmee with golf nearby

Kissimmee / Orange Lake Resort

Villa / 2 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £114 / night

£795 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Orange Lake Resort, Kissimmee Area, Florida  …see more

from £57 / night

£397 / week

View

Excellent 5/5 

20 Photos

Distance approx 2.96 miles from Crestwynd Bay   |  Show on Map

Holiday condo with golf nearby in Kissimmee

Kissimmee / Lindfields

Condo / 3 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £57 / night

£397 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
Superb spacious three bedroomed condo 4 miles from Disney, excellent golf courses, restaurants and shops Light, airy accommodation with plenty of space and luxurious comfort. Cable TV DVD Internet Free Calls icemaker cooker microwave dishwasher utensils travel cot highchair pets  …see more

from £85 / night

£595 - £665 / week

View

Excellent 5/5 

25 Photos

Distance approx 2.97 miles from Crestwynd Bay   |  Show on Map

Holiday villa in Kissimmee

Kissimmee / Lindfields

Villa / 3 Bedrooms / sleeps 8

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £85 / night

£595 - £665 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Newly updated 'Platinum' rated 3 Bedroom 2 Bathroom villa.Huge 60 ft west facing pool deck with 6 sunloungers around 32ft x16ft private pool and spa. 4 miles from Disneyworld, reached within 10 minutes on busy days via shortcut. The house is very quietly located, but only a 5 minute drive / $10 taxi ride to nearby restaurants and bars  …see more

from £100 / night

£700 - £840 / week

View

Excellent 5/5 

24 Photos

Distance approx 3.11 miles from Crestwynd Bay   |  Show on Map

Villa rental in Kissimmee

Kissimmee / Sunset Lakes

Villa / 4 Bedrooms / sleeps 10

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £100 / night

£700 - £840 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 104 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
'The Retreat' Villa at Sunset Lakes is a beautiful 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 £42 / night

£290 - £325 / week

View

Excellent 5/5 

24 Photos

Distance approx 3.11 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday home accommodation

Kissimmee / Lindfields

House / 3 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £42 / night

£290 - £325 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Vacation home with all amenities, Gated community Free Wifi, 32" flat screen TV in the Lounge, heated resort pool kept at 85F, a large hot tub all near a beautiful lake. ample car parking, close to Disney, 30 minutes from Seaworld and universal Studio's. BBQ Area Sun bathe on the pool deck with sunbeds, tables and chairs, take a dip in the pool or relax in the hot tub.  …see more

from £147 / night

£1025 - £3273 / week

View

24 Photos

Distance approx 3.14 miles from Crestwynd Bay   |  Show on Map

Kissimmee holiday home rental

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £147 / night

£1025 - £3273 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This superior Vacation Home provide upscale resort living with many details and amenities found only in the most exclusive developments Reunion is located right in between the Grand Golf Resorts of Florida, and just a short 30 minute drive to Orlando Airport  …see more

from £1257 / night

£8795 - £14750 / week

View

24 Photos

Distance approx 3.22 miles from Crestwynd Bay   |  Show on Map

Holiday villa with swimming pool, golf nearby in Reunion

Central Florida / Reunion

Villa / 11 Bedrooms / sleeps 23

1 night min stay

Add to shortlist

from £1257 / night

£8795 - £14750 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Take a Look at this Huge 11 Bedroom Mansion + Cinema Room On Reunion Resort.  …see more

from £147 / night

£1025 - £1637 / week

View

24 Photos

Distance approx 3.3 miles from Crestwynd Bay   |  Show on Map

Home rental in Kissimmee

Central Florida / Kissimmee

House / 6 Bedrooms / sleeps 14

3 Nights min stay

Add to shortlist

from £147 / night

£1025 - £1637 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Internet Connection – Telephone - Cable/Satellite - Multiple TV's – TV – Gourmet – Kitchen - Linens Provided – Coffeemaker - Gas Grill - Patio Living Area: 3,291 SqFt - Lot Size: 3,811 SqFt  …see more

from £36 / night

£250 - £450 / week

View

Excellent 5/5 

24 Photos

Distance approx 3.32 miles from Crestwynd Bay   |  Show on Map

Holiday condo rental

Kissimmee / Legacy Dunes Resort

Condo / 2 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £36 / night

£250 - £450 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 78 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
2 Double bedroom/2 bathroom 1100 sq ft condo with screened balcony and lake & fountain view. 4 miles from Disney World. Literally 10 minutes from anywhere - Disney, Epcot, Animal Kingdom, Hollywood Studios, Celebration, Sea World, Discovery Cove & Universal Studios. The condo is situated in a gated resort community with free parking. Special rates for monthly lets apply.  …see more

from £481 / night

£3366 - £4095 / week

View

24 Photos

Distance approx 3.35 miles from Crestwynd Bay   |  Show on Map

Reunion holiday villa let

Central Florida / Reunion

Villa / 6 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £481 / night

£3366 - £4095 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This stunning Mediterranean style home, custom built by one of Reunion's leading builders will surpass your every expectation. Soaring ceilings boast extensive detailing, rich furnishings, and fabrics have been beautifully combined to create a luxurious feel throughout.  …see more

from £1143 / night

£7995 - £11465 / week

View

24 Photos

Distance approx 3.4 miles from Crestwynd Bay   |  Show on Map

Reunion holiday villa rental

Central Florida / Reunion

Villa / 12 Bedrooms / sleeps 24

1 night min stay

Add to shortlist

from £1143 / night

£7995 - £11465 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Exquisite Custom Built 12 Bedroom Mansion designed with an exclusive lifestyle in mind. This unique residence is the perfect place to spend your days or evenings at play or relaxing, occupying a prime location within the resort whilst offering privacy and seclusion.  …see more

from £357 / night

£2495 - £3650 / week

View

23 Photos

Distance approx 3.43 miles from Crestwynd Bay   |  Show on Map

Reunion holiday villa rental

Central Florida / Reunion

Villa / 7 Bedrooms / sleeps 14

1 night min stay

Add to shortlist

from £357 / night

£2495 - £3650 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Best Price Huge 7 Bedroom Reunion Resort Vacation Home-Breathtaking views-Movie Theatre & Games Room!!!  …see more

from £75 / night

£525 - £950 / week

View

Excellent 5/5 

20 Photos

Distance approx 3.44 miles from Crestwynd Bay   |  Show on Map

Holiday townhouse in Kissimmee

Kissimmee / Paradise Palms

Townhouse / 4 Bedrooms / sleeps 10

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £75 / night

£525 - £950 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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

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