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Callahan Vacation Packages

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Callahan Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Economy Inn Jax-OP

Economy Inn Jax-OP

2 out of 5
Price was $361, price is now $289 per person
$289
per person
Dec 6 - Dec 10
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Stay at this hotel in Jacksonville. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Orange Park Mall and bestbet Orange Park are located nearby.
Good cleaning! Manager was good in his explanation of fees credit my account right away for any in all deposits very friendly! I would still stay there again price was right

Reviewed on Nov 3, 2026

Hammock Beach Golf Resort & Spa

Hammock Beach Golf Resort & Spa

4 out of 5
Price was $1,664, price is now $1,166 per person
$1,166
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
Book a stay at this luxury resort in Palm Coast. Enjoy free WiFi, free parking, and 9 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Hammock Beach Ocean Course and Old Salt Park Beach are located nearby.

Southbank Apartments by Landing

Southbank Apartments by Landing

4 out of 5
Price was $897, price is now $674 per person
$674
per person
Dec 5 - Dec 12
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Stay at this aparthotel in Jacksonville. Enjoy a rooftop terrace, a fitness center, and daily housekeeping. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.
The place was clean and well furnished. This was my first time booking an apartment instead of a hotel, and I loved having access to a kitchen that was fully stocked with cookware and utensils. My one complaint is that there seemed to be frequent events going on nearby that caused parking to disappear on the weekends, since I didn’t pay for a parking spot.

Reviewed on Oct 4, 2026

Seaside Amelia Inn

Seaside Amelia Inn

3 out of 5
Price was $726, price is now $548 per person
$548
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Jacksonville (JAX)
Book a stay at this beach hotel in Fernandina Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Fernandina Beach Main Beach Park and Amelia Island Lighthouse are located nearby.
Everything from location, staff and room was exceptional!

Reviewed on Oct 30, 2026

Amelia by the South

Amelia by the South

4.5 out of 5
Price was $4,715, price is now $3,593 per person
$3,593
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this luxury condo in Fernandina Beach. Enjoy free WiFi, free parking, and private pools. Popular attractions Omni Amelia Island Resort Golf and Fernandina Beach are located nearby.

Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
Price was $951, price is now $729 per person
$729
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

Landing Apartments near Downtown Jacksonville

Landing Apartments near Downtown Jacksonville

3 out of 5
Price was $1,229, price is now $1,010 per person
$1,010
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Landing Apartments Downtown Palm Coast

Landing Apartments Downtown Palm Coast

4 out of 5
Price was $1,584, price is now $1,329 per person
$1,329
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this business-friendly apartment in Palm Coast. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Cypress Knoll Golf Club and Wadsworth Park are located nearby.
I've stayed in a lot of hotels and this was the most luxurious. Clean, full kitchen, two bedrooms, walk-in closets, and three large flat screen TV and a balcony. I will be returning!!

Reviewed on Oct 17, 2026

Callahan Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was $551, price is now $428 per person
$428
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
Amelia by the South

Amelia by the South

4.5 out of 5
Price was $4,715, price is now $3,593 per person
$3,593
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
Downtown Jacksonville
Price was $951, price is now $729 per person
$729
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Holiday Inn Express Jacksonville Beach by IHG

Holiday Inn Express Jacksonville Beach by IHG

3 out of 5
Price was $568, price is now $445 per person
$445
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)

Callahan Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Amelia Hotel at the Beach

Amelia Hotel at the Beach

2.5 out of 5
Price was $628, price is now $474 per person
$474
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Jacksonville (JAX)
Hammock Beach Golf Resort & Spa

Hammock Beach Golf Resort & Spa

4 out of 5
Price was $1,664, price is now $1,166 per person
$1,166
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
Southbank Apartments by Landing

Southbank Apartments by Landing

4 out of 5
Downtown Jacksonville
Price was $897, price is now $674 per person
$674
per person
Dec 5 - Dec 12
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Seaside Amelia Inn

Seaside Amelia Inn

3 out of 5
Price was $726, price is now $548 per person
$548
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Jacksonville (JAX)

Top Flight Deals

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

Frontier Airlines
Mon, Dec 7 - Wed, Dec 16
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$129 Roundtrip, found 3 days ago
$129
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Dallas-Fort Worth Intl. to Jacksonville Intl., returning Wed, Dec 16, priced at $129 found 3 days ago
Frontier Airlines
Wed, Dec 9 - Mon, Dec 14
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$134 Roundtrip, found 12 hours ago
$134
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Wed, Dec 9 from Baltimore Washington Intl. Thurgood Marshall to Jacksonville Intl., returning Mon, Dec 14, priced at $134 found 12 hours ago
Frontier Airlines
Wed, Dec 2 - Wed, Dec 9
ORD
O'Hare Intl.
JAX
Jacksonville Intl.
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Dec 2 from O'Hare Intl. to Jacksonville Intl., returning Wed, Dec 9, priced at $135 found 2 days ago
Frontier Airlines
Wed, Nov 18 - Sat, Dec 5
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$170 Roundtrip, found 16 hours ago
$170
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Wed, Nov 18 from Philadelphia Intl. to Jacksonville Intl., returning Sat, Dec 5, priced at $170 found 16 hours ago