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A coastal landscape with a tree covered in Spanish moss, a marshy area, and a distant view of the ocean.

Callahan Vacations from ￥87,909

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The Latest Callahan Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Property amenity
    Oct 15 - Oct 18

    WaterWalk Extended Stay by Wyndham Jacksonville Deerwood Pk + Flight

    Southside
    3 nights
    2.0 star property
    8.8/10 - Excellent (927 reviews)
    Roundtrip • Chicago (CHI) - Jacksonville (JAX)
    ORD - JAX • 1 stop JAX - ORD • 1 stop
    ￥100,826
    ￥87,909
    per traveler
    found 1 day ago
    WaterWalk Extended Stay by Wyndham Jacksonville Deerwood Pk
  • Coffee service
    Oct 15 - Oct 18

    Landing Furnished Apartments near UNF + Flight

    Jacksonville
    3 nights
    4.0 star property
    10/10 - Exceptional (1 review)
    "Highly recommend! Felt like home, can’t wait to stay again"
    Reviewed June 7, 2026
    Roundtrip • Chicago (CHI) - Jacksonville (JAX)
    ORD - JAX • 1 stop JAX - ORD • 1 stop
    ￥150,127
    ￥124,724
    per traveler
    found 1 day ago
    Landing Furnished Apartments near UNF
  • Serves lunch and dinner
    Oct 15 - Oct 18

    Marriott Jacksonville Downtown + Flight

    Downtown Jacksonville
    3 nights
    4.0 star property
    8.4/10 - Very Good (1,006 reviews)
    "The staff was very friendly and accommodating. The room and pool was clean. I didn’t have any issues at all throughout my stay."
    Reviewed July 21, 2026
    Roundtrip • Chicago (CHI) - Jacksonville (JAX)
    ORD - JAX • 1 stop JAX - ORD • 1 stop
    ￥127,177
    ￥107,861
    per traveler
    found 1 day ago
    Marriott Jacksonville Downtown
  • Exterior
    Oct 15 - Oct 18

    Hyatt Regency Jacksonville + Flight

    Downtown Jacksonville
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,725 reviews)
    "Hotel was great for a last minute trip to Jacksonville for the family with kids, was able to get a room with a king size bed for the parents and a room with two queens connected to our room for the kids. Didn’t have to share the bathroom or the tv. Pool was great opened very early and was open late. Safe property will staff everywhere even in the middle of the night wil definitely stay again when visiting Jacksonville"
    Reviewed July 21, 2026
    Roundtrip • Chicago (CHI) - Jacksonville (JAX)
    ORD - JAX • 1 stop JAX - ORD • 1 stop
    ￥127,101
    ￥110,758
    per traveler
    found 1 day ago
    Hyatt Regency Jacksonville
  • Dining
    Oct 15 - Oct 18

    Amelia Hotel at the Beach + Flight

    Fernandina Beach
    3 nights
    2.5 star property
    8.6/10 - Excellent (2,219 reviews)
    "The property was beautiful and perfectly placed to enjoy the surrounding area. Within five minutes of the beach, and multiple fantastic restaurants in close range. The hotel was very clean, tidy, and cute. The staff was friendly and helpful, and the hotel offered a small shop with helpful amenities. HIGHLY recommend this hotel!"
    Reviewed July 21, 2026
    Roundtrip • Chicago (CHI) - Jacksonville (JAX)
    ORD - JAX • 1 stop JAX - ORD • 1 stop
    ￥109,676
    ￥97,811
    per traveler
    found 1 day ago
    Amelia Hotel at the Beach

What to do in Callahan

Guided Kayak Eco Tour: Real Florida Adventure

Guided Kayak Eco Tour: Real Florida Adventure

￥9,752
per adult
90% of travelers recommend
Guided Kayak Eco Tour: Real Florida Adventure
See all activities in Callahan

Callahan Hotel Deals

Front of property - evening/night

Hyatt Place Jacksonville Airport

Hyatt Place Jacksonville Airport
3.0 star property
20.9 km from Callahan
9.0 out of 10, Wonderful, (2,533 reviews)
The price is ￥16,414
￥18,630 total
includes taxes & fees
Aug 18 - Aug 19
Hyatt Place Jacksonville Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See all properties in Callahan
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.