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Leesburg Vacation Packages

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Leesburg Flight + Hotel Packages

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 $695, price is now $314 per person
$314
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 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 Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $665, price is now $329 per person
$329
per person
May 3 - May 9
found 21 hours 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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,057, price is now $531 per person
$531
per person
May 22 - May 25
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 Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,127, price is now $578 per person
$578
per person
Apr 27 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $1,361, price is now $703 per person
$703
per person
Jun 4 - Jun 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.
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 $820, price is now $447 per person
$447
per person
May 23 - May 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $898, price is now $498 per person
$498
per person
May 16 - May 18
found 6 hours 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 Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $1,119, price is now $655 per person
$655
per person
Apr 20 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.

Leesburg Vacation Packages 3-4 Night Stays

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 $415, price is now $235 per person
$235
per person
Apr 27 - Apr 30
found 1 day ago
Roundtrip non-stop 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
International Drive District
Price was $1,249, price is now $387 per person
$387
per person
May 6 - May 9
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,057, price is now $531 per person
$531
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,608, price is now $845 per person
$845
per person
May 1 - May 5
found 8 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Orlando (MCO)

Leesburg Vacation Packages 5-7 Night Stays

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 $695, price is now $314 per person
$314
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 $1,181, price is now $422 per person
$422
per person
Apr 27 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $665, price is now $329 per person
$329
per person
May 3 - May 9
found 21 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
International Drive District
Save 100% on your flight
Price was $1,127, price is now $578 per person
$578
per person
Apr 27 - May 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Top Flight Deals

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

Delta
Tue, Jun 23 - Tue, Jul 7
COS
Colorado Springs
MCO
Orlando Intl.
$461 Roundtrip, found 6 days ago
$461
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 23 from Colorado Springs to Orlando Intl., returning Tue, Jul 7, priced at $461 found 6 days ago
Delta
Tue, Jun 30 - Tue, Jul 14
COS
Colorado Springs
MCO
Orlando Intl.
$473 Roundtrip, found 6 days ago
$473
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 30 from Colorado Springs to Orlando Intl., returning Tue, Jul 14, priced at $473 found 6 days ago
Bargain Flight
Tue, Mar 24 - Tue, Mar 31
COS
Colorado Springs
MCO
Orlando Intl.
$494 Roundtrip, found 3 days ago
$494
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Mar 24 from Colorado Springs to Orlando Intl., returning Tue, Mar 31, priced at $494 found 3 days ago
American Airlines
Mon, Jun 1 - Wed, Jun 17
COS
Colorado Springs
MCO
Orlando Intl.
$496 Roundtrip, found 6 days ago
$496
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Jun 1 from Colorado Springs to Orlando Intl., returning Wed, Jun 17, priced at $496 found 6 days ago