Overstreet Vacations from $2,029

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The Latest Overstreet vacation packages

Price found within the past 48 hours. Click for updated prices.
The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,742, price is now $2,029 per person
$2,029
per person
Jul 6 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
9.6/10 Exceptional! (219 reviews)
Amazing hotel, we will definitely be back!

Reviewed on May 11, 2026

Steps to Private Beach Access Pool + Bikes Seacrest 30A

Steps to Private Beach Access Pool + Bikes Seacrest 30A

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $4,165, price is now $2,990 per person
$2,990
per person
Jul 12 - Jul 17
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
10/10 Exceptional! (1 review)
This house is well maintained and clean with comfortable beds and plenty of space for our family of five. There is definitely room for more people too. Each room has its own bathroom which makes getting ready for outings much easier. The house is located in the seacrest beach section of Rosemary Beach and is only a five minute walk to pool and 10 minute walk to beach. The pool lagoon area is beautiful with a cafe and bathrooms and plenty of seating for the month of August. The beach has a beautiful entrance and white sand with clear waters and chair/umbrellas to rent for the day. There is also a very good cafe steps up from beach called Crabby Steve’s high point. We walked everywhere in seacrest and proper Rosemary beach near the Pearl Hotel. We ate good meals every day. Lots of restaurants to try. This house did not have bikes included in our rental price. If this is important to you check out bike rental options before you go. Our family swam in pool and golf most of day, especially bc August weather brings so much heat and humidity to this area, and we got dressed nicely and walked to dinner in the evening and then walked to ice cream and shops before going back to house. We had quiet, quality family time.

Reviewed on Aug 27, 2025

Southern Shores by Avantstay Seacrest Beach Resort Pool

Southern Shores by Avantstay Seacrest Beach Resort Pool

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $3,873, price is now $2,782 per person
$2,782
per person
Jul 12 - Jul 17
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
10/10 Exceptional! (1 review)
Tidewater Horizon by Avantstay Beachfront Condo + Indoor Pool + Spa Amenities + Movie Theater + Near Pier Park

Tidewater Horizon by Avantstay Beachfront Condo + Indoor Pool + Spa Amenities + Movie Theater + Near Pier Park

4 out of 5
Save 100% on your flight
Price was $4,271, price is now $3,083 per person
$3,083
per person
Jul 21 - Jul 28
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Panama City (ECP)
No reviews
South Shore 30A by Avantstay Gulf View Pool

South Shore 30A by Avantstay Gulf View Pool

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $4,003, price is now $2,900 per person
$2,900
per person
Jul 12 - Jul 17
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
6/10 (1 review)
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Overstreet Hotel Deals

Driftwood Inn

Driftwood Inn

2 out of 5
2105 U.S. 98 Mexico Beach FL
Fully refundableReserve now, pay when you stay
$231 nightly
The price is $259 total per night from May 26 to May 27
$259 total
May 26 - May 27
Total with taxes and fees
9.6/10 Exceptional! (34 reviews)
Excelent location

Reviewed on May 12, 2026

Driftwood Inn
Comfort Suites

Comfort Suites

2.5 out of 5
264 N Tyndall Pkwy Panama City FL
Fully refundable
$101 nightly
The price is $108 total per night from May 19 to May 20
$108 total
May 19 - May 20
Total with taxes and fees
8.6/10 Excellent! (747 reviews)
I requested a 1st floor room being a solo Female traveler i really appreciated that. Friendly staff

Reviewed on May 7, 2026

Comfort Suites
MainStay Suites Port Saint Joe South

MainStay Suites Port Saint Joe South

2.5 out of 5
3951 E Highway 98 Port St. Joe FL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $188 total per night from Jun 14 to Jun 15
$188 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (715 reviews)
The pool was closed most of the time we were there other than that it was wonderful.

Reviewed on May 11, 2026

MainStay Suites Port Saint Joe South
See all 1,804 properties in Overstreet
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.

Find the Best Overstreet Vacation Packages

Overstreet Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does an Overstreet vacation package cost?
You'll find cheap prices from $2,029 on Expedia for your Overstreet getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Overstreet costs.
What are the cheapest months to go to Overstreet?
August, November and December are great times to search for cheap Overstreet vacation packages. Choosing to travel in less busy months means you can generally find better prices on accommodations and flights.
How many days is enough for Overstreet?
Usually, a handful of days is enough to go to the top attractions during your Overstreet vacation. However, if you'd like to have more time to unwind or go on day tours, think about extending your trip.
How to find the best Overstreet package deals?
Begin your search for an Overstreet package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Overstreet package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Overstreet adventure off to a flying start.
Is it cheaper to book an Overstreet vacation as a package?
You can enjoy significant savings on your Overstreet getaway by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Overstreet?
If you're considering a spontaneous Overstreet adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Overstreet?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to vacation in Overstreet.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to Overstreet.
  3. Use Expedia's trip planning tool to explore Overstreet: Research every aspect of your trip to Overstreet with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go for: Now that you're up to speed on Overstreet, you can work out the right length of your break. Put together a draft itinerary and allocate enough time to cover everything you want to see.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find an Overstreet vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Have a look at our dedicated travel guide to find some fun things to do in Overstreet. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities once you arrive.

Does Expedia offer Book Now, Pay Later Overstreet vacation packages?
If you're anything like us, you love traveling but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Overstreet break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.