Search Deals on
Callaway Vacation Packages

Build your package with 2 more options

Callaway Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Beach Street Cottages

Beach Street Cottages

3.5 out of 5
Price was $850, price is now $617 per person
$617
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this 3.5-star beach hotel in Miramar Beach. Enjoy free WiFi, parking (surcharge), and concierge services. Popular attractions Miramar Beach and Henderson Beach State Park are located nearby.
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Save 100% on your flight
Price was $1,066, price is now $721 per person
$721
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Walton Beach (VPS)
Stay at this 5-star luxury resort in Destin. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Henderson Beach State Park and Big Kahuna's Water and Adventure Park are located nearby.
Monarch by Avantstay Stunning Estate 1 Block to Beach, Swim Up Bar, Hot Tub, & Rooftop Views

Monarch by Avantstay Stunning Estate 1 Block to Beach, Swim Up Bar, Hot Tub, & Rooftop Views

3.5 out of 5
Save 100% on your flight
Price was $9,191, price is now $6,293 per person
$6,293
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this 3.5-star beach cottage in Destin. Enjoy free parking, a beach locale, and concierge services. Popular attractions Henderson Beach State Park and Miramar Beach are located nearby.
WaterSound Inn

WaterSound Inn

4 out of 5
Save 100% on your flight
Price was $1,527, price is now $1,058 per person
$1,058
per person
Jan 6 - Jan 11
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
Stay at this 4-star golf hotel in Panama City Beach. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the property condition in our reviews. Popular attractions Alys Beach and Seaside Beach are located nearby.
WaterColor Inn & Resort

WaterColor Inn & Resort

4 out of 5
Save 100% on your flight
Price was $1,670, price is now $1,183 per person
$1,183
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this 4-star beach resort in Santa Rosa Beach. Enjoy free parking, 10 outdoor pools, and 3 restaurants. Popular attractions Seaside Beach and Grayton Beach State Park are located nearby.
The Pearl Hotel

The Pearl Hotel

4 out of 5
Save 100% on your flight
Price was $1,861, price is now $1,323 per person
$1,323
per person
Jan 6 - Jan 11
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
Stay at this 4-star beach resort in Panama City Beach. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Alys Beach and Rosemary Beach are located nearby.
Gulf-view Retreat w/ Rooftop Deck + Private Pool Villa Anesi by Avantstay

Gulf-view Retreat w/ Rooftop Deck + Private Pool Villa Anesi by Avantstay

3 out of 5
Save 100% on your flight
Price was $3,432, price is now $2,471 per person
$2,471
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this 3-star beach cottage in Santa Rosa Beach. Enjoy free parking, a beach locale, and balconies. Popular attractions Blue Mountain Beach and Sandestin Golf Resort - Raven, Burnt Pine, Baytowne, The Links are located nearby.
Harborside by Avantstay Expansive Destin Retreat

Harborside by Avantstay Expansive Destin Retreat

3 out of 5
Save 100% on your flight
Price was $4,535, price is now $3,297 per person
$3,297
per person
Dec 22 - Dec 29
just found
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Stay at this 3-star cottage in Destin. Enjoy patios, in-room washers/dryers, and in-room fireplaces. Popular attractions Big Kahuna's Water and Adventure Park and Destin Harbor Boardwalk are located nearby.

Callaway Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
Okaloosa Island
Price was $580, price is now $420 per person
$420
per person
Jan 12 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Pensacola (PNS)
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
Price was $1,066, price is now $721 per person
$721
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Fort Walton Beach (VPS)
Beach Street Cottages

Beach Street Cottages

3.5 out of 5
Price was $676, price is now $496 per person
$496
per person
Jan 12 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Fort Walton Beach (VPS)
The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,487, price is now $1,108 per person
$1,108
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Panama City (ECP)

Callaway Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Henderson Beach Resort & Spa

The Henderson Beach Resort & Spa

5 out of 5
Crystal Beach
Save 100% on your flight
Price was $1,485, price is now $958 per person
$958
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
Monarch by Avantstay Stunning Estate 1 Block to Beach, Swim Up Bar, Hot Tub, & Rooftop Views

Monarch by Avantstay Stunning Estate 1 Block to Beach, Swim Up Bar, Hot Tub, & Rooftop Views

3.5 out of 5
Crystal Beach
Save 100% on your flight
Price was $9,191, price is now $6,293 per person
$6,293
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)
WaterSound Inn

WaterSound Inn

4 out of 5
WaterSound Beach
Save 100% on your flight
Price was $1,527, price is now $1,058 per person
$1,058
per person
Jan 6 - Jan 11
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
WaterColor Inn & Resort

WaterColor Inn & Resort

4 out of 5
Watercolor
Save 100% on your flight
Price was $1,670, price is now $1,183 per person
$1,183
per person
Jan 6 - Jan 11
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Walton Beach (VPS)

Top Flight Deals

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

Frontier Airlines
Mon, Nov 3 - Sat, Nov 8
DFW
Dallas-Fort Worth Intl.
PNS
Pensacola Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 3 from Dallas-Fort Worth Intl. to Pensacola Intl., returning Sat, Nov 8, priced at $154 found 1 day ago
Frontier Airlines
Sun, Oct 26 - Fri, Oct 31
ORD
O'Hare Intl.
PNS
Pensacola Intl.
$156 Roundtrip, found 21 hours ago
$156
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sun, Oct 26 from O'Hare Intl. to Pensacola Intl., returning Fri, Oct 31, priced at $156 found 21 hours ago
Sun Country Airlines
Sun, Jan 18 - Thu, Jan 29
MSP
Minneapolis - St. Paul Intl.
VPS
Northwest Florida Regional
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Sun, Jan 18 from Minneapolis - St. Paul Intl. to Northwest Florida Regional, returning Thu, Jan 29, priced at $166 found 1 day ago
Frontier Airlines
Sat, Oct 25 - Fri, Oct 31
ATL
Hartsfield-Jackson Atlanta Intl.
PNS
Pensacola Intl.
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Oct 25 from Hartsfield-Jackson Atlanta Intl. to Pensacola Intl., returning Fri, Oct 31, priced at $166 found 1 day ago