Search Deals on
Callahan Vacation Packages

Build your package with 2 more options

Callahan Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Tricove Inn & Suites

Tricove Inn & Suites

2.5 out of 5
Price was $604, price is now $444 per person
$444
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Jacksonville (JAX)
Book a stay at this business-friendly motel in Jacksonville. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Johns Town Center and EverBank Stadium are located nearby.
Good night sleep and just a little noise

Reviewed on Sep 18, 2026

Landing Chic 1bd, Gym, Rooftop Lounge

Landing Chic 1bd, Gym, Rooftop Lounge

3 out of 5
Save 100% on your flight
Price was $1,072, price is now $758 per person
$758
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)
Stay at this apartment in Jacksonville. Enjoy free parking, a 24-hour fitness center, and an in-room coffeemaker. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.

The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Save 100% on your flight
Price was $716, price is now $510 per person
$510
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)
Book a stay at this beach vacation home in Fernandina Beach. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Omni Amelia Island Resort Golf and Amelia Island State Park are located nearby.

Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
Save 100% on your flight
Price was $1,092, price is now $809 per person
$809
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.
Great hotel. Perfect location to the Jaguars stadium. Great bar, great staff. Highly recommend.

Reviewed on Sep 19, 2026

Marriott Jacksonville Downtown

Marriott Jacksonville Downtown

4 out of 5
Save 100% on your flight
Price was $828, price is now $623 per person
$623
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.
Clean spacious room

Reviewed on Sep 19, 2026

Amelia by the Sea

Amelia by the Sea

4 out of 5
Price was $5,585, price is now $4,229 per person
$4,229
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
Stay at this condo in Fernandina Beach. Enjoy free WiFi, free parking, and balconies. Popular attractions Omni Amelia Island Resort Golf and Fernandina Beach are located nearby.

Landing Apartments near Downtown Jacksonville

Landing Apartments near Downtown Jacksonville

3 out of 5
Price was $1,300, price is now $1,002 per person
$1,002
per person
Nov 22 - Nov 28
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
Stay at this apartment in Jacksonville. Enjoy free parking, an outdoor pool, and a 24-hour fitness center. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.
Close to ball. Park. Convenient parking

Reviewed on Sep 3, 2026

Candlewood Suites Jacksonville East Merril Road by IHG

Candlewood Suites Jacksonville East Merril Road by IHG

2.5 out of 5
Price was $1,155, price is now $908 per person
$908
per person
Nov 22 - Nov 28
found 24 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions EverBank Stadium and VyStar Veterans Memorial Arena are located nearby.

Callahan Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Midtown Lodge

Midtown Lodge

2.5 out of 5
Southside
Price was $250, price is now $208 per person
$208
per person
Nov 2 - Nov 6
found 13 hours ago
Roundtrip flight included
Cleveland (CLE) to Jacksonville (JAX)
Amelia by the Sea

Amelia by the Sea

4 out of 5
Price was $5,585, price is now $4,229 per person
$4,229
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
Elizabeth Pointe Lodge

Elizabeth Pointe Lodge

3.5 out of 5
Price was $1,400, price is now $1,150 per person
$1,150
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
Hampton Inn Jacksonville South/I-95 at JTB

Hampton Inn Jacksonville South/I-95 at JTB

2.5 out of 5
Southside
Price was $403, price is now $333 per person
$333
per person
Nov 2 - Nov 6
found 12 hours ago
Roundtrip flight included
Cleveland (CLE) to Jacksonville (JAX)

Callahan Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Tricove Inn & Suites

Tricove Inn & Suites

2.5 out of 5
Southside
Price was $604, price is now $444 per person
$444
per person
Oct 21 - Oct 26
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Jacksonville (JAX)
Landing Chic 1bd, Gym, Rooftop Lounge

Landing Chic 1bd, Gym, Rooftop Lounge

3 out of 5
Urban Core
Save 100% on your flight
Price was $1,072, price is now $758 per person
$758
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Save 100% on your flight
Price was $716, price is now $510 per person
$510
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)
Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
Downtown Jacksonville
Save 100% on your flight
Price was $1,092, price is now $809 per person
$809
per person
Dec 13 - Dec 18
found 22 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Jacksonville (JAX)

Top Flight Deals

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

Frontier Airlines
Tue, Oct 27 - Sat, Oct 31
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$119 Roundtrip, found 23 hours ago
$119
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Baltimore Washington Intl. Thurgood Marshall to Jacksonville Intl., returning Sat, Oct 31, priced at $119 found 23 hours ago
Frontier Airlines
Sat, Oct 24 - Tue, Nov 10
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$124 Roundtrip, found 4 days ago
$124
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Philadelphia Intl. to Jacksonville Intl., returning Tue, Nov 10, priced at $124 found 4 days ago
Frontier Airlines
Tue, Nov 10 - Thu, Nov 19
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$169 Roundtrip, found 23 hours ago
$169
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, Nov 10 from O'Hare Intl. to Jacksonville Intl., returning Thu, Nov 19, priced at $169 found 23 hours ago
Frontier Airlines
Tue, Oct 13 - Thu, Oct 15
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 13 from Dallas-Fort Worth Intl. to Jacksonville Intl., returning Thu, Oct 15, priced at $216 found 1 day ago