Cheap Vacations in Windsor Hills

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Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $598, price is now $403 per person
$403
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
Price was $673, price is now $465 per person
$465
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)

3-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $289, price is now $176 per person
$176
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $398, price is now $189 per person
$189
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop 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 $678, price is now $344 per person
$344
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Flamingo Inn Beachfront

Flamingo Inn Beachfront

2 out of 5
Save 100% on your flight
Price was $337, price is now $195 per person
$195
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop 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 $483, price is now $306 per person
$306
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $382, price is now $245 per person
$245
per person
Jan 27 - Jan 30
found 3 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $362, price is now $232 per person
$232
per person
Jan 30 - Feb 2
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Bahama House

Bahama House

3 out of 5
Save 100% on your flight
Price was $488, price is now $314 per person
$314
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Price was $422, price is now $275 per person
$275
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Maverick Resort

The Maverick Resort

3 out of 5
Save 100% on your flight
Price was $312, price is now $204 per person
$204
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop 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
Price was $511, price is now $338 per person
$338
per person
Jan 25 - Jan 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $480, price is now $323 per person
$323
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

4-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $464, price is now $263 per person
$263
per person
Jan 25 - Jan 29
found 16 hours 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 $788, price is now $392 per person
$392
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Save 100% on your flight
Price was $1,016, price is now $638 per person
$638
per person
Jan 25 - Jan 29
found 16 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Price was $656, price is now $414 per person
$414
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $857, price is now $546 per person
$546
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
The Alfond Inn

The Alfond Inn

4 out of 5
Save 100% on your flight
Price was $1,528, price is now $979 per person
$979
per person
Feb 4 - Feb 8
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 $899, price is now $578 per person
$578
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
Price was $630, price is now $410 per person
$410
per person
Feb 12 - Feb 16
found 10 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 $598, price is now $403 per person
$403
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $528, price is now $361 per person
$361
per person
Feb 12 - Feb 16
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs

4 out of 5
Save 100% on your flight
Price was $803, price is now $561 per person
$561
per person
Jan 25 - Jan 29
found 16 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 $893, price is now $628 per person
$628
per person
Feb 5 - Feb 9
found 7 hours ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)

5-night Windsor Hills vacations

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

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $535, price is now $290 per person
$290
per person
Feb 4 - Feb 9
found 8 hours 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
Price was $657, price is now $295 per person
$295
per person
Feb 4 - Feb 9
found 8 hours 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 $595, price is now $291 per person
$291
per person
Jan 28 - Feb 2
found 9 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
Save 100% on your flight
Price was $1,219, price is now $612 per person
$612
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
I-Drive Hotel at Universal

I-Drive Hotel at Universal

2.5 out of 5
Price was $652, price is now $328 per person
$328
per person
Jan 28 - Feb 2
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $815, price is now $424 per person
$424
per person
Jan 28 - Feb 2
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
Save 100% on your flight
Price was $688, price is now $385 per person
$385
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop 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 $1,242, price is now $699 per person
$699
per person
Feb 3 - Feb 8
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
ette hotel

ette hotel

5 out of 5
Price was $1,430, price is now $831 per person
$831
per person
Jan 28 - Feb 2
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Fold Hotels Orlando

The Fold Hotels Orlando

2 out of 5
Price was $810, price is now $475 per person
$475
per person
Jan 28 - Feb 2
found 12 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
Save 100% on your flight
Price was $1,188, price is now $700 per person
$700
per person
Feb 11 - Feb 16
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 $589, price is now $350 per person
$350
per person
Feb 11 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)

6-7 night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,325, price is now $279 per person
$279
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $1,311, price is now $584 per person
$584
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $876, price is now $427 per person
$427
per person
Feb 1 - Feb 7
found 3 hours ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $1,380, price is now $769 per person
$769
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
Save 100% on your flight
Price was $794, price is now $447 per person
$447
per person
Feb 9 - Feb 16
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
Save 100% on your flight
Price was $758, price is now $434 per person
$434
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $619, price is now $356 per person
$356
per person
Jan 27 - Feb 2
found 10 hours 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 $811, price is now $467 per person
$467
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
Price was $1,171, price is now $682 per person
$682
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
Price was $700, price is now $408 per person
$408
per person
Jan 19 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Lifetime of Vacations Resort

Lifetime of Vacations Resort

3 out of 5
Save 100% on your flight
Price was $740, price is now $431 per person
$431
per person
Jan 24 - Jan 30
found 4 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Orlando (MCO)
ette hotel

ette hotel

5 out of 5
Price was $1,786, price is now $1,054 per person
$1,054
per person
Feb 9 - Feb 15
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)

Flight deals to Windsor Hills

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

Sat, Mar 7 - Tue, Mar 10
JFK
New York
MCO
Orlando
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Mar 7 from New York to Orlando, returning Tue, Mar 10, priced at $68 found 1 day ago
Wed, Mar 4 - Wed, Mar 11
EWR
New York
MCO
Orlando
$68 Roundtrip, found 2 hours ago
$68
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Mar 4 from New York to Orlando, returning Wed, Mar 11, priced at $68 found 2 hours ago
Mon, Jan 5 - Wed, Jan 14
LGA
New York
MCO
Orlando
$68 Roundtrip, found 4 hours ago
$68
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Jan 5 from New York to Orlando, returning Wed, Jan 14, priced at $68 found 4 hours 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
Disney World 2 Miles! Family condo

Disney World 2 Miles! Family condo

Kissimmee FL
0.33 mi from Windsor Hills
$240 nightly
The price is $268 total per night
$268 total
Dec 19 - Dec 20
Total with taxes and fees
Located in Kissimmee (Windsor Hills), this condo is within a 10-minute drive of Walt Disney World® Resort and Old Town.
Pool
Hot Tub
Spacious 3 Bedroom TownHome..3 minutes from Disney World!

Spacious 3 Bedroom TownHome..3 minutes from Disney World!

Kissimmee FL
0.27 mi from Windsor Hills
Get rates
With a stay at this vacation home, you'll be centrally located in Kissimmee, within a 10-minute drive of Walt Disney World® Resort and Old Town.
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.

^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.