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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.
Holiday Inn Express Jacksonville South Bartram Prk by IHG

Holiday Inn Express Jacksonville South Bartram Prk by IHG

2.5 out of 5
Price was $629, price is now $486 per person
$486
per person
Jan 14 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Genovar Park and Falling Waters Pond are located nearby.

The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was $709, price is now $553 per person
$553
per person
Jan 14 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
We enjoyed our stay and look forward to returning in the near future. All the restaurants in the area were great….

Reviewed on Oct 27, 2026

Historic Springfield Apartments by Landing

Historic Springfield Apartments by Landing

4 out of 5
Price was $777, price is now $607 per person
$607
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this business-friendly aparthotel in Jacksonville. Enjoy free parking, 2 outdoor pools, and a 24-hour fitness center. Popular attractions VyStar Veterans Memorial Arena and EverBank Stadium are located nearby.
Good

Reviewed on Aug 10, 2026

Hampton Inn Jacksonville South/I-95 at JTB

Hampton Inn Jacksonville South/I-95 at JTB

2.5 out of 5
Price was $870, price is now $684 per person
$684
per person
Dec 13 - Dec 18
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions St. Johns Town Center and EverBank Stadium are located nearby.
Clean room, the breakfast and parking was most helpful to me during my stay.

Reviewed on Oct 29, 2026

Amelia by the South

Amelia by the South

4.5 out of 5
Price was $4,423, price is now $3,491 per person
$3,491
per person
Dec 26 - Dec 29
found 7 hours ago
Roundtrip 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.

Seaside Amelia Inn

Seaside Amelia Inn

3 out of 5
Price was $707, price is now $559 per person
$559
per person
Jan 14 - Jan 18
found 7 hours ago
Roundtrip non-stop 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.
This was a great property for price, breakfast was good and it did change so you weren’t eating the same thing every day. Property was under some renovation. But was really nice, very peaceful, with in driving distant of good restaurants.

Reviewed on Oct 27, 2026

The Ritz-Carlton, Amelia Island

The Ritz-Carlton, Amelia Island

5 out of 5
Save 100% on your flight
Price was $2,228, price is now $1,782 per person
$1,782
per person
Jan 14 - Jan 18
found 9 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
Book a stay at this luxury resort in Fernandina Beach. Enjoy a full-service spa, a golf course, and 3 hot tubs. Our guests praise the property condition in our reviews. Popular attractions Omni Amelia Island Resort Golf and Peters Point Beachfront Park are located nearby.
A beautiful place

Reviewed on Oct 11, 2026

Holiday Inn Express Jacksonville Beach by IHG

Holiday Inn Express Jacksonville Beach by IHG

3 out of 5
Price was $611, price is now $490 per person
$490
per person
Jan 14 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
Book a stay at this business-friendly hotel in Jacksonville Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Gonzales Park and Players by the Sea are located nearby.
…

Reviewed on Oct 29, 2026

Callahan Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Jacksonville South Bartram Prk by IHG

Holiday Inn Express Jacksonville South Bartram Prk by IHG

2.5 out of 5
Price was $629, price is now $486 per person
$486
per person
Jan 14 - Jan 18
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Jacksonville (JAX)
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was $709, price is now $553 per person
$553
per person
Jan 14 - Jan 18
found 7 hours 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 $4,423, price is now $3,491 per person
$3,491
per person
Dec 26 - Dec 29
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Seaside Amelia Inn

Seaside Amelia Inn

3 out of 5
Price was $707, price is now $559 per person
$559
per person
Jan 14 - Jan 18
found 7 hours 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.
Holiday Inn Express Jacksonville Beach by IHG

Holiday Inn Express Jacksonville Beach by IHG

3 out of 5
Price was $695, price is now $519 per person
$519
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Price was $996, price is now $692 per person
$692
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
Beachside Motel

Beachside Motel

2 out of 5
Price was $855, price is now $596 per person
$596
per person
Jan 5 - Jan 12
found 1 day 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 16 hours 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
Wed, Dec 9 - Mon, Dec 14
BWI
Baltimore Washington Intl. Thurgood Marshall
JAX
Jacksonville Intl.
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Dec 9 from Baltimore Washington Intl. Thurgood Marshall to Jacksonville Intl., returning Mon, Dec 14, priced at $119 just found
Frontier Airlines
Mon, Dec 7 - Sat, Dec 12
DFW
Dallas-Fort Worth Intl.
JAX
Jacksonville Intl.
$129 Roundtrip, found 7 hours ago
$129
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Dallas-Fort Worth Intl. to Jacksonville Intl., returning Sat, Dec 12, priced at $129 found 7 hours ago
Frontier Airlines
Tue, Nov 17 - Sat, Dec 5
PHL
Philadelphia Intl.
JAX
Jacksonville Intl.
$156 Roundtrip, found 7 hours ago
$156
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Philadelphia Intl. to Jacksonville Intl., returning Sat, Dec 5, priced at $156 found 7 hours ago
Delta
Wed, Dec 2 - Mon, Dec 14
AUS
Austin-Bergstrom Intl.
JAX
Jacksonville Intl.
$157 Roundtrip, found 7 hours ago
$157
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Dec 2 from Austin-Bergstrom Intl. to Jacksonville Intl., returning Mon, Dec 14, priced at $157 found 7 hours ago