Cheap Vacations in Windsor Hills

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Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $641, price is now $315 per person
$315
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,598, price is now $787 per person
$787
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $732, price is now $376 per person
$376
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $663, price is now $352 per person
$352
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $731, price is now $424 per person
$424
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Save 100% on your flight
Price was $1,051, price is now $624 per person
$624
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $629, price is now $408 per person
$408
per person
May 1 - May 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $897, price is now $583 per person
$583
per person
May 1 - May 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
Price was $1,743, price is now $1,142 per person
$1,142
per person
May 1 - May 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Save 100% on your flight
Price was $1,319, price is now $869 per person
$869
per person
Apr 30 - May 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

3-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $409, price is now $285 per person
$285
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $933, price is now $540 per person
$540
per person
May 8 - May 11
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $477, price is now $286 per person
$286
per person
Apr 25 - Apr 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $629, price is now $386 per person
$386
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $489, price is now $301 per person
$301
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Grand Seas MOD Collection by Sonesta

Grand Seas MOD Collection by Sonesta

3.5 out of 5
Price was $524, price is now $358 per person
$358
per person
Apr 30 - May 3
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Price was $595, price is now $418 per person
$418
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
Save 100% on your flight
Price was $659, price is now $465 per person
$465
per person
Apr 30 - May 3
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Villas at Fortune Place

Villas at Fortune Place

3 out of 5
Save 100% on your flight
Price was $705, price is now $498 per person
$498
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

3 out of 5
Price was $1,393, price is now $990 per person
$990
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $787, price is now $561 per person
$561
per person
Apr 24 - Apr 27
found 1 hour ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,080, price is now $778 per person
$778
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

4-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $467, price is now $301 per person
$301
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,598, price is now $787 per person
$787
per person
Apr 17 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $673, price is now $377 per person
$377
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $874, price is now $492 per person
$492
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $770, price is now $445 per person
$445
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $626, price is now $373 per person
$373
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $694, price is now $463 per person
$463
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

3 out of 5
Save 100% on your flight
Price was $1,129, price is now $762 per person
$762
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $936, price is now $633 per person
$633
per person
Apr 16 - Apr 20
found 6 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Price was $819, price is now $562 per person
$562
per person
Apr 22 - Apr 26
found 1 hour ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,275, price is now $877 per person
$877
per person
Apr 16 - Apr 20
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Save 100% on your flight
Price was $622, price is now $430 per person
$430
per person
Apr 11 - Apr 15
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

5-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $540, price is now $312 per person
$312
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Extended Stay America Suites Orlando Conv Ctr Universal Blvd

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

2.5 out of 5
Price was $3,288, price is now $537 per person
$537
per person
Apr 30 - May 5
found 22 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $1,309, price is now $521 per person
$521
per person
Apr 14 - Apr 19
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Price was $899, price is now $391 per person
$391
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $641, price is now $315 per person
$315
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $732, price is now $376 per person
$376
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $731, price is now $424 per person
$424
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Grand Seas MOD Collection by Sonesta

Grand Seas MOD Collection by Sonesta

3.5 out of 5
Save 100% on your flight
Price was $542, price is now $331 per person
$331
per person
Apr 26 - May 1
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $760, price is now $471 per person
$471
per person
Apr 17 - Apr 22
found 19 hours ago
Roundtrip flight included
Islip (ISP) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $1,149, price is now $714 per person
$714
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

3 out of 5
Save 100% on your flight
Price was $1,433, price is now $936 per person
$936
per person
Apr 17 - Apr 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Ocean Walk Resort

Ocean Walk Resort

3.5 out of 5
Save 100% on your flight
Price was $812, price is now $544 per person
$544
per person
Apr 26 - May 1
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

6-7 night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Alhambra Villas

Alhambra Villas

3 out of 5
Price was $464, price is now $297 per person
$297
per person
Apr 11 - Apr 17
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $1,126, price is now $487 per person
$487
per person
Apr 11 - Apr 17
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $793, price is now $357 per person
$357
per person
Apr 11 - Apr 17
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $663, price is now $352 per person
$352
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Save 100% on your flight
Price was $1,051, price is now $624 per person
$624
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Save 100% on your flight
Price was $1,355, price is now $823 per person
$823
per person
Apr 12 - Apr 19
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $1,025, price is now $651 per person
$651
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $652, price is now $415 per person
$415
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Grand Seas MOD Collection by Sonesta

Grand Seas MOD Collection by Sonesta

3.5 out of 5
Price was $654, price is now $419 per person
$419
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Orlando Palms Hotel

Orlando Palms Hotel

2.5 out of 5
Save 100% on your flight
Price was $625, price is now $406 per person
$406
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $1,573, price is now $1,029 per person
$1,029
per person
Apr 11 - Apr 17
found 18 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,264, price is now $831 per person
$831
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

Flight deals to Windsor Hills

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, Apr 21 - Tue, Apr 28
LGA
New York
MCO
Orlando
$80 Roundtrip, found 3 days ago
$80
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 21 from New York to Orlando, returning Tue, Apr 28, priced at $80 found 3 days ago
Tue, Mar 17 - Thu, Mar 19
DTW
Detroit
MCO
Orlando
$87 Roundtrip, found 4 days ago
$87
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Detroit to Orlando, returning Thu, Mar 19, priced at $87 found 4 days ago
Sat, May 9 - Sun, May 10
ORD
Chicago
MCO
Orlando
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 9 from Chicago to Orlando, returning Sun, May 10, priced at $87 found 6 days ago

Top rated hotels for your Windsor Hills vacation

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Kissimmee FL
0.24 mi from Windsor Hills
Get rates
With a stay at this condo, you'll be centrally located in Kissimmee, within a 10-minute drive of Walt Disney World® Resort and Old Town.
Pool
Kitchen
Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee FL
0.17 mi from Windsor Hills
Get rates
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.
Pool
Hot Tub
Windsor Hills Private Luxury Pool House, Sleeps 13

Windsor Hills Private Luxury Pool House, Sleeps 13

Kissimmee FL
0.25 mi from Windsor Hills
Get rates
With a stay at this villa in Kissimmee (Windsor Hills), you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Windsor Hills
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Picks

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.