Cheap Vacations in Windsor Hills

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Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Flamingo Inn Beachfront

Flamingo Inn Beachfront

2 out of 5
Price was $436, price is now $189 per person
$189
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,433, price is now $544 per person
$544
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,126, price is now $441 per person
$441
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $534, price is now $224 per person
$224
per person
Jan 17 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $587, price is now $253 per person
$253
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,001, price is now $436 per person
$436
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $924, price is now $463 per person
$463
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $533, price is now $276 per person
$276
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Mi Casa Hotel

Mi Casa Hotel

2.5 out of 5
Save 100% on your flight
Price was $445, price is now $238 per person
$238
per person
Feb 4 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
ette hotel

ette hotel

5 out of 5
Price was $1,685, price is now $932 per person
$932
per person
Jan 20 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $335, price is now $206 per person
$206
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $690, price is now $250 per person
$250
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $647, price is now $317 per person
$317
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $578, price is now $320 per person
$320
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $616, price is now $379 per person
$379
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $422, price is now $269 per person
$269
per person
Jan 29 - Feb 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $534, price is now $350 per person
$350
per person
Jan 16 - Jan 19
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $378, price is now $248 per person
$248
per person
Feb 7 - Feb 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Save 100% on your flight
Price was $571, price is now $375 per person
$375
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $792, price is now $534 per person
$534
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Resort on Cocoa Beach

The Resort on Cocoa Beach

3.5 out of 5
Save 100% on your flight
Price was $593, price is now $400 per person
$400
per person
Jan 23 - Jan 26
found 5 hours ago
Roundtrip flight included
Boston (BOS) 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
Save 100% on your flight
Price was $382, price is now $202 per person
$202
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $892, price is now $284 per person
$284
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $732, price is now $300 per person
$300
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,001, price is now $436 per person
$436
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $502, price is now $254 per person
$254
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $533, price is now $276 per person
$276
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $736, price is now $421 per person
$421
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $501, price is now $302 per person
$302
per person
Jan 17 - Jan 21
found 7 hours ago
Roundtrip flight included
Boston (BOS) 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 $342, price is now $217 per person
$217
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $756, price is now $480 per person
$480
per person
Jan 19 - Jan 23
found 9 hours ago
Roundtrip flight included
Boston (BOS) 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 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Fold Hotels Orlando

The Fold Hotels Orlando

2 out of 5
Save 100% on your flight
Price was $760, price is now $488 per person
$488
per person
Jan 17 - Jan 21
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

5-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Flamingo Inn Beachfront

Flamingo Inn Beachfront

2 out of 5
Price was $436, price is now $189 per person
$189
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $926, price is now $360 per person
$360
per person
Jan 29 - Feb 3
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $587, price is now $253 per person
$253
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
I-Drive Hotel at Universal

I-Drive Hotel at Universal

2.5 out of 5
Price was $677, price is now $316 per person
$316
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $469, price is now $246 per person
$246
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $627, price is now $334 per person
$334
per person
Jan 16 - Jan 21
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Save 100% on your flight
Price was $782, price is now $420 per person
$420
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $390, price is now $210 per person
$210
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
Price was $963, price is now $530 per person
$530
per person
Feb 4 - Feb 9
found 8 hours ago
Roundtrip flight included
Boston (BOS) 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 $908, price is now $519 per person
$519
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Save 100% on your flight
Price was $790, price is now $466 per person
$466
per person
Feb 4 - Feb 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
Save 100% on your flight
Price was $450, price is now $268 per person
$268
per person
Jan 16 - Jan 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

6-7 night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Mi Casa Hotel

Mi Casa Hotel

2.5 out of 5
Save 100% on your flight
Price was $445, price is now $238 per person
$238
per person
Feb 4 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,433, price is now $544 per person
$544
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,126, price is now $441 per person
$441
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $902, price is now $369 per person
$369
per person
Jan 27 - Feb 3
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
I-Drive Hotel at Universal

I-Drive Hotel at Universal

2.5 out of 5
Price was $802, price is now $359 per person
$359
per person
Feb 4 - Feb 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $552, price is now $261 per person
$261
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $848, price is now $416 per person
$416
per person
Feb 4 - Feb 11
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Parkway International Resort

Parkway International Resort

3 out of 5
Price was $924, price is now $463 per person
$463
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $686, price is now $362 per person
$362
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $515, price is now $279 per person
$279
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
WorldQuest Orlando Resort

WorldQuest Orlando Resort

4 out of 5
Save 100% on your flight
Price was $965, price is now $529 per person
$529
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,273, price is now $702 per person
$702
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) 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, Jan 31 - Thu, Feb 12
JFK
New York
MCO
Orlando
$68 Roundtrip, found 8 hours ago
$68
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jan 31 from New York to Orlando, returning Thu, Feb 12, priced at $68 found 8 hours ago
Fri, Jan 30 - Wed, Feb 11
EWR
New York
MCO
Orlando
$68 Roundtrip, found 8 hours ago
$68
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Fri, Jan 30 from New York to Orlando, returning Wed, Feb 11, priced at $68 found 8 hours ago
Sat, Jan 31 - Thu, Feb 12
LGA
New York
MCO
Orlando
$68 Roundtrip, found 8 hours ago
$68
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jan 31 from New York to Orlando, returning Thu, Feb 12, priced at $68 found 8 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.
Disney World 2 Miles! Family condo

Disney World 2 Miles! Family condo

Kissimmee FL
0.33 mi from Windsor Hills
Get rates
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.
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.