List your home
Apply filters
£ to

Holiday homes 22

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
  • Crestwynd Bay Clear

Location

  • All locations

more +

less -

Filters applied: Dishwasher (22)

Payment Protection
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
22 Results   |  
17 Photos

Kissimmee / Crestwynd Bay

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £104 / night

£725 - £1000 / week

View

Key info:

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

7 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £127 / night

£884 - £1302 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
We invite you to enjoy our condo on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful 1st floor condo in the Windsor Hills Resort. Attention to every detail  …see more

Excellent 5/5 

7 Photos

Kissimmee / Crestwynd Bay

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

6 Nights min stay

Add to shortlist

from £100 / night

£700 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
close to disney close to orlando close to outlets/malls free theater showing about three times a day. Depending on the requirements There can be a 1 bed for 2 couples/ 1bed 1 sofa for family of 2 adults 2 children in a front room at the higher rates. WEEKLY BOOKINGS F  …see more


27 Feb 2015

5/5

"Excelente lugar contodo lo necesario para la familia"

Todo estaba en impecables condiciones, cocina completa, es como estar en casa. Ello facilita la estadía y permite ahorros, sobre todo al estar con familia. Cerca de los centros de entretención Unive… More


15 Oct 2014

5/5

"Great location with so much in the area"

Three of us stayed here under my sister, who is a timeshare owner. After we got checked in (took about an hour on a busy Sunday), we somehow ended up with a handicap room. That was much smaller than… More


30 Jun 2014

5/5

"Wonderful Stay at Westgate Towncenter"

Our reservation was for 5 consecutive weeks and we often run into difficulty in remaining in the same unit. Since I am handicapped, it's extremely troublesome trying to pack and repack when we have t… More

See all reviews Continue

Featured properties

Very Good 4/5 

18 Photos

Kissimmee / Crestwynd Bay

Villa / 4 Bedrooms / sleeps 8

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £61 / night

£425 - £475 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 65 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Four bed villa with 40' heated pool and spa within ten minutes drive of Disney in a quiet sub division. Good links to I-4 for Seaworld, Universal, premium outlets and all other attractions. Free Broadband Wifi and North american calls Large deck area with ample pool f  …see more


27 May 2015

5/5

"Looking forward to stay at this villa again !!! Love it"

Minutes away from. Theme parks , lots of space . Great price & very clean. I already planning muy next vacation and hopefully will be available to book at the same location. I highly recommend it to… More


13 Apr 2015

5/5

"Awesome Vacation Rental!"

I was so deathly afraid of booking a vacation rental online but Two Hoots exceeded our expectations and was so easy dealing with the owner had no probelm gaining acsess to the house at all. The price … More


9 Apr 2014

5/5

"Too Hoots great location"

Having visited Florida many times we decided to stay in a different location ,using holidaylettings we found Mikes villa .when we arrived we were pleasantly surprised as it was very well equipped… More

See all reviews Continue

24 Photos

Kissimmee / Crestwynd Bay

Townhouse / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £175 / night

£1220 - £1807 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to this beautiful vacation home in Kissimmee, Florida. Featuring four bedrooms, four baths, and a garage, this spacious home has been carefully and lovingly furnished to ensure that you have a comfortable and memorable experience. The full kitchen is equipped w  …see more

22 Photos

Kissimmee / Crestwynd Bay

Townhouse / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £126 / night

£878 - £1294 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Experience a sunny Florida vacation in this 3 bedroom, 3 baths Saddlebrook model which features 1400 sq. ft.  This bedroom sleeps 6 in one king, one queen, and two twin sized beds, and each bedroom has its own private bathroom.  Included in the full sized kitchen are  …see more

20 Photos

Kissimmee / Crestwynd Bay

Townhouse / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £126 / night

£878 - £1294 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Fully immerse yourself in the Florida sunshine by experiencing it in this beautiful tropically themed townhome.  Accommodations for 8 include sleeper sofa, Queen, King and Twin beds. This home has four TV's and a fully equipped kitchen for your convenience. Step out t  …see more

18 Photos

Kissimmee / Crestwynd Bay

Townhouse / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £126 / night

£878 - £1294 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
After vacationing in Windsor Hills with some friends last year, we decided that staying in a townhouse is a much nicer experience than coming back to an impersonal hotel room after a day at the parks. We just bought our vacation home and would like to share it with you  …see more

11 Photos

Kissimmee / Crestwynd Bay

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £144 / night

£1007 - £1228 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Lovely 4 Bedroom/ Bathroom private pool home located in the gated community of Windsor Palms. The bedding consists: King and Queen Master Bedroom, 1 twin bedroom and bunkbed room. Pool and spa great for swimming. Windsor Palms has a nice community clubhouse with sundry  …see more

20 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £148 / night

£1033 - £1497 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This splendidly decorated three-bedroom vacation villa features a spectacular, balcony view of Tom Watson&039;s Independence Course, a living room, dinning area and fully equipped kitchen. Each bedroom has a private bath and TV. Villa includes the finest personal produc  …see more

9 Photos

Kissimmee / Crestwynd Bay

Townhouse / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £151 / night

£1056 - £1549 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
We invite you to enjoy your next vacation at our beautifully decorated 3 bed/3 bath Townhome with a fun splash pool. Sleeping accommodation features an elegant master suite with king size bed; Second bedroom with a queen size; a third bedroom with 2 twins and a pull-out  …see more

16 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £123 / night

£861 - £1156 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Gardenia floor plan (second floor unit)- This beautiful 3 bedroom/ 2 bath condo is located in the brand new gated community of Oakwater, located 1.5 miles from Disney. The 4,000 square foot Oakwater clubhouse features a lagoon-style pool, tennis, volleyball and basketba  …see more

8 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £144 / night

£1007 - £1400 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Welcome to Oakwater Resort and this stunning 3 bedroom, 2.5 bathroom (1776 sq. ft.) rental located near the theme parks in Orlando, Florida. This vacation rental has all the comforts of home and more. The kitchen is fully furnished and ideal for those times when it make  …see more

8 Photos

Kissimmee / Crestwynd Bay

House / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £123 / night

£861 - £1156 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
We invite you to enjoy our Oakwater Condo on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book now and enjoy all that Oakwater has to offer!! Enjoy the 4000 square foot clubhouse that features  …see more

12 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £127 / night

£884 - £1302 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Beautifully decorated new 3 bedroom 2 bath condo in sought after Windsor Hills resort community. Near clubhouse with resort style pool, sundry shop, fitness center, water slide, billards, gameroom, and movie theater. Just 1.5 miles to Walt Disney World! Weekday Weekend  …see more

5 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £123 / night

£861 - £1156 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Enjoy your vacation or business trip in this tastefully decorated 3 bedroom/2 bath /1 car garage condo (2nd floor Gardenia plan) of 1,475 sq feet. Condo consists of one king bed, one queen bed, two twin beds, two queen-size sofa sleepers in the living room, internet acc  …see more

24 Photos

Kissimmee / Crestwynd Bay

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £299 / night

£2088 - £2825 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
This stunning 5 bedroom 5 bathroom home is located on a corner lot in Paradise Palms and is only 1 block from the clubhouse. The home is professionally decorated throughout and features stainless steel appliances, granite counter tops and upgraded cabinets in the kitche  …see more

23 Photos

Kissimmee / Crestwynd Bay

Townhouse / 4 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £193 / night

£1351 - £1991 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Floor Plan (The Beach Palm) 1,914 sq. ft. 2 story townhome We invite you to enjoy our townhome on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at this beautiful townhome  …see more

9 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £124 / night

£867 - £1164 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Hello and Thank you for considering our Orlando Vacation Home. Our 3 bedroom, 2 bathroom, 1455 sq. ft. 2nd floor Condo sleeps 8 comfortably. It has been completely repainted, carpets cleaned and all new furniture, new beds (1 king size, l queen size, 2 twins, and pull o  …see more

9 Photos

Kissimmee / Crestwynd Bay

Condo / 3 Bedrooms / sleeps 8

5 Nights min stay

Add to shortlist

from £124 / night

£867 - £1164 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Gardenia floor plan (second floor unit)- 1417 sqft This beautiful 3 bedroom/ 2 bath condo is located in the gated community of Oakwater, located 1.5 miles from Disney. The 4,000 sq. clubhouse features a lagoon-style pool, tennis courts volleyball courts, basketball cour  …see more

15 Photos

Kissimmee / Crestwynd Bay

House / 5 Bedrooms / sleeps 10

5 Nights min stay

Add to shortlist

from £262 / night

£1831 - £2471 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Floor Plan (The Seville) 2,336 sq ft. 2 story home with pool & spa (South facing pool) We invite you to enjoy our home on your next trip to Orlando. Absolutely perfect for family groups, this property features all the comforts of home and more! Book your vacation now at  …see more

19 Photos

Kissimmee / Crestwynd Bay

Townhouse / 3 Bedrooms / sleeps 8

1 night min stay

Add to shortlist

from £80 / night

£560 - £1791 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Crestwynd Bay is a gated residential community, and is the closest that you can get to Disney parks without staying in one of the Disney Resorts. It's only 1.3 mile from Disney main gate, and a walk able distance from 192, the road that goes through Kissimmee.  …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