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Maitland Vacation Packages

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Maitland Flight + Hotel Packages

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 $531, price is now $316 per person
$316
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $823, price is now $373 per person
$373
per person
Jun 6 - Jun 13
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 $792, price is now $362 per person
$362
per person
Jun 6 - Jun 13
found 8 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.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $1,290, price is now $696 per person
$696
per person
Jun 24 - Jun 28
found 5 hours 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 The Orlando Eye are located nearby.
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,689, price is now $954 per person
$954
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Orlando International Premium Outlets 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 $1,185, price is now $671 per person
$671
per person
Jul 15 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel 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 Aquatica are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,815, price is now $1,058 per person
$1,058
per person
Jul 12 - Jul 17
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Book a stay at this beach aparthotel 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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $717, price is now $434 per person
$434
per person
Jun 17 - Jun 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orange County Convention Center and The Orlando Eye are located nearby.

Maitland Vacation Packages 3-4 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 $531, price is now $316 per person
$316
per person
Jun 17 - Jun 20
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
International Drive District
Save 100% on your flight
Price was $1,290, price is now $696 per person
$696
per person
Jun 24 - Jun 28
found 5 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
Save 100% on your flight
Price was $717, price is now $434 per person
$434
per person
Jun 17 - Jun 20
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
International Drive District
Save 100% on your flight
Price was $736, price is now $447 per person
$447
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Maitland Vacation Packages 5-7 Night Stays

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

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $792, price is now $362 per person
$362
per person
Jun 6 - Jun 13
found 8 hours 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 $869, price is now $390 per person
$390
per person
Jun 6 - Jun 13
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
International Drive District
Price was $1,742, price is now $782 per person
$782
per person
Jun 14 - Jun 21
found 2 hours 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 $823, price is now $373 per person
$373
per person
Jun 6 - Jun 13
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.

Frontier Airlines
Wed, May 27 - Tue, Jun 2
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$63 Roundtrip, found 1 hour ago
$63
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 27 from Newark Liberty Intl. Airport to Orlando Intl., returning Tue, Jun 2, priced at $63 found 1 hour ago
Frontier Airlines
Mon, Jun 1 - Wed, Jun 10
TTN
Mercer
MCO
Orlando Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jun 1 from Mercer to Orlando Intl., returning Wed, Jun 10, priced at $80 found 1 hour ago
Frontier Airlines
Wed, May 27 - Fri, Jun 12
LGA
LaGuardia
MCO
Orlando Intl.
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, May 27 from LaGuardia to Orlando Intl., returning Fri, Jun 12, priced at $100 found 1 hour ago
Frontier Airlines
Sat, May 16 - Thu, May 21
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$126 Roundtrip, found 3 days ago
$126
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 16 from Detroit Metropolitan Wayne County to Orlando Intl., returning Thu, May 21, priced at $126 found 3 days ago