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Winter Springs Vacation Packages

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Winter Springs Flight + Hotel Packages

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

Palazzo Lakeside Hotel

3 out of 5
Price was $760, price is now $297 per person
$297
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,634, price is now $621 per person
$621
per person
Jun 6 - Jun 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,220, price is now $1,034 per person
$1,034
per person
May 6 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach condo in Cocoa Beach. Enjoy free parking, a beach locale, and free water park access. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach and Ron Jon Surf Shop are located nearby.
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $678, price is now $330 per person
$330
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.
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 $1,464, price is now $821 per person
$821
per person
May 8 - May 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orlando International Premium Outlets and The Orlando Eye are located nearby.
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $702, price is now $405 per person
$405
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Orange County Convention Center and Disney Springs™ are located nearby.
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $1,254, price is now $756 per person
$756
per person
May 24 - May 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this luxury aparthotel in Kissimmee. Enjoy 11 outdoor pools, 7 restaurants, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions Reunion Resort Golf Course and ESPN Wide World of Sports Complex are located nearby.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $620, price is now $375 per person
$375
per person
Apr 24 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Winter Springs Vacation Packages 3-4 Night Stays

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

Palazzo Lakeside Hotel

3 out of 5
Price was $760, price is now $297 per person
$297
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,342, price is now $564 per person
$564
per person
Jun 6 - Jun 10
just found
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,277, price is now $717 per person
$717
per person
May 1 - May 4
found 24 hours 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 $527, price is now $332 per person
$332
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Winter Springs Vacation Packages 5-7 Night Stays

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 $731, price is now $331 per person
$331
per person
May 3 - May 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 $1,231, price is now $338 per person
$338
per person
May 30 - Jun 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,634, price is now $621 per person
$621
per person
Jun 6 - Jun 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,072, price is now $441 per person
$441
per person
May 19 - May 24
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Top Flight Deals

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

Frontier Airlines
Tue, Apr 7 - Wed, Apr 22
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Apr 7 from Philadelphia Intl. to Orlando Intl., returning Wed, Apr 22, priced at $80 just found
Frontier Airlines
Sun, Apr 26 - Thu, Apr 30
TTN
Mercer
MCO
Orlando Intl.
$88 Roundtrip, found 4 hours ago
$88
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sun, Apr 26 from Mercer to Orlando Intl., returning Thu, Apr 30, priced at $88 found 4 hours ago
Spirit Airlines
Tue, Apr 7 - Thu, Apr 16
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$93 Roundtrip, found 4 hours ago
$93
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Apr 7 from Detroit Metropolitan Wayne County to Orlando Intl., returning Thu, Apr 16, priced at $93 found 4 hours ago
Frontier Airlines
Mon, Apr 27 - Thu, Apr 30
MSP
Minneapolis - St. Paul Intl.
MCO
Orlando Intl.
$100 Roundtrip, found 4 hours ago
$100
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Minneapolis - St. Paul Intl. to Orlando Intl., returning Thu, Apr 30, priced at $100 found 4 hours ago