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Holiday Lettings
> North America
> United States
> Florida
> Central Florida
> Kissimmee
> Villas and condos in Windsor Hills Resort

Villas in Windsor Hills Resort and Condos - Holiday Lettings - Holiday Rentals Windsor Hills Resort

Price per night

£1 £750 -

Bedrooms

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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Apartment (23)
  • Villa (62)
  • Cottage (9)
  • House (55)
  • Bungalow (4)
  • Townhouse (6)
  • Yacht (1)
  • Boathouse (1)
  • Condo (50)
  • Private room (2)
  • Hotel apartment (11)
  • Caravan/Mobile Home (1)
  • Guest house (1)

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226 Holiday homes

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Great rentals within 20 miles that match your search

Holiday villa in Davenport

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10
26 reviews

from £152 / night

£921 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Reunion

Reunion house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 15

from £348 / night

£2,199 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday hotel apartment in Treasure Island

Treasure Island hotel apartment

  • 12 bedrooms
  • 11 bathrooms
  • sleeps 49

from £2,474 / night

£17,312 / week

1 / 53

Great rentals within 20 miles that match your search

Orlando holiday condo rental

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £85 / night

£596 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday apartment with shared pool, golf nearby in Orlando

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
27 reviews

from £70 / night

£485 / week

1 / 38

Great rentals within 20 miles that match your search

Boathouse letting in Clearwater

Clearwater boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £247 / night

£1,725 / week

1 / 4

Great rentals within 20 miles that match your search

St. Pete Beach holiday condo rental

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
7 reviews

from £99 / night

£687 / week

1 / 54

Great rentals within 20 miles that match your search

Holiday hotel apartment in Treasure Island

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £275 / night

£1,924 / week

1 / 26

Great rentals within 20 miles that match your search

Treasure Island holiday hotel apartment rental

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £275 / night

£1,924 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday home with golf nearby in New Port Richey

New Port Richey house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
7 reviews

from £210 / night

£1,469 / week

1 / 27

Great rentals within 20 miles that match your search

Cottage rental in Tarpon Springs with golf nearby

Tarpon Springs cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £91 / night

£596 / week

1 / 11

Great rentals within 20 miles that match your search

Holiday hotel apartment in Treasure Island

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £275 / night

£1,924 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday hotel apartment in Treasure Island

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £275 / night

£1,924 / week

1 / 39

Great rentals within 20 miles that match your search

Treasure Island holiday hotel apartment rental

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £275 / night

£1,924 / week

1 / 41

Great rentals within 20 miles that match your search

Hotel apartment rental in Treasure Island

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £275 / night

£1,924 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday hotel apartment in Treasure Island

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

from £367 / night

£2,565 / week

1 / 41

Great rentals within 20 miles that match your search

Treasure Island holiday hotel apartment let

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £275 / night

£1,924 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday home in Indian Shores

Indian Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6
18 reviews

from £339 / night

£2,086 / week

1 / 41

Great rentals within 20 miles that match your search

Longboat Key holiday villa accommodation

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10
16 reviews

from £390 / night

£2,725 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday townhouse with golf nearby in Kissimmee

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £130 / night

£911 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home in Gibsonton

Gibsonton house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

from £475 / night

£3,325 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday condo letting

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £161 / night

£1,122 / week

1 / 40

Great rentals within 20 miles that match your search

Holiday condo in Orlando

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £236 / night

£1,649 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday apartment rental

Cocoa Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4
4 reviews

from £202 / night

£1,411 / week

1 / 66

Great rentals within 20 miles that match your search

Holiday home in Cocoa

Cocoa house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £239 / night

£1,466 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday apartment in St. Petersburg

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £129 / night

£871 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday condo in Treasure Island

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
80 reviews

from £176 / night

£1,109 - £4,178 / week

1 / 41

Great rentals within 20 miles that match your search

Indian Shores holiday condo rental

Indian Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £173 / night

£1,206 / week

1 / 41

Great rentals within 20 miles that match your search

Holiday villa in Reunion

Reunion villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
2 reviews

from £182 / night

£1,271 / week

1 / 60

Great rentals within 20 miles that match your search

Holiday condo rental

St. Pete Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

from £161 / night

£1,122 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday home with shared pool in ChampionsGate

ChampionsGate house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 18

from £206 / night

£1,374 / week

1 / 27

Great rentals within 20 miles that match your search

Holiday apartment rental

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £106 / night

£734 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday condo in Indian Shores

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £160 / night

£1,116 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday cottage rental

Tavares cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £57 / night

£395 / week

1 / 15

Great rentals within 20 miles that match your search

Holiday condo in Indian Shores

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £161 / night

£1,122 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday apartment in Indian Shores

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6
8 reviews

from £77 / night

£535 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday villa with swimming pool, golf nearby in Kissimmee

Kissimmee villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 13
3 reviews

from £176 / night

£1,238 / week

1 / 30

Great rentals within 20 miles that match your search

Condo rental in Indian Shores

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £161 / night

£1,122 / week

1 / 32

Great rentals within 20 miles that match your search

Tavares holiday cottage rental

Tavares cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £51 / night

£352 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday cottage rental

Tavares cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £54 / night

£373 / week

1 / 11

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