Escape to Five Flags Retreat, Family & Pet Friendly
Five Flags Retreat is the perfect spot for your family vacation or work trip to Pensacola, Florida. Our home is a comfortable getaway with lots of room for your family and friends to gather. Spread out in 2400 sq feet, with 4 bedrooms, a bonus family room, and a separate office — or spend quality time together in the open dining room, living room & kitchen. Bring your fur family to enjoy the large fenced-in backyard. A quick drive to downtown (6 miles), the beach (13 miles), NAS (10 miles) and area hospitals.
Known as the "City of Five Flags" Pensacola is a beautiful historic town. Our spacious home captures a bit of historic Pensacola and southern charm. It features four bedrooms and sleeps 8 (10 is max using the sofa bed). The master suite has it's own full bathroom and a sitting room which also opens onto the covered patio; this room offers extra sleeping space on the sofa bed. There are two additional bedrooms downstairs; one with a queen bed and the other with two twin beds. The large upstairs bedroom features a queen bed on one side and a cute spot to get comfortable with a book or games. If you are visiting for work, you'll appreciate the office, complete with desk, wi-fi and wireless printer. The kitchen is fully stocked with everything you need to enjoy a home cooked meal at the dining table which seats 8. Enjoy the beautiful Florida weather in the large fenced-in yard featuring a fire pit, propane grill, covered outdoor dining area (table for 6 with a fan!), patio seating and yard games. If you prefer inside, you'll be entertained with two smart TVs, wi-fi, books and board games. Veteran owned & operated.
Stays are limited to a minimum of three and maximum of 27 nights (may vary by season and there may be exceptions). A "starter set" of toiletries, toilet paper, paper towels, trash bags is provided. This will not be replenished during your stay. Longer term stays may be negotiated with additional cleanings required. Please contact the owner.
*NOTE: Security cameras at exterior entry doors. There are no interior security cameras. Tampering with or disabling security cameras is a violation of house rules and grounds for immediate cancellation of your reservation without refund.
**For us to consider your inquiry, please respond with answers to the following: What is the purpose of your visit to our area? Number of people (adults and children) who will be staying? Are you bringing any pets and how many? As listed in our house rules, we require a signed rental agreement and photo ID (age requirement of 23). Request to book means that you have read and agree to house rules and rental agreement.
WILDLIFE: Our property is in Florida. You may see wildlife including birds, squirrel, frogs, skinks, lizards, and maybe the occasional possum or armadillo in our yard. You may also see insects, bugs, bats, snakes, ants, bees, wasps, spiders, mice, raccoon, and other creatures that call Florida their home. The Gulf, bay, rivers will also contain fish, snakes, sharks and the creatures that reside in those habitats. Please take care when hiking and in the Gulf and other waters in the area. For the safety of your pet, dogs should be supervised when outside. Refunds or discounts will not be issued due to creature sightings or bug bites while exploring the surroundings. We do have quarterly pest control.
*Cancellation Policy Due to Weather* This home is located on the coast of the Gulf in Florida, which is subject to seasonal weather variations. Per our Firm Cancellation Policy, no refunds or discounts are offered for weather-related cancellations unless a named storm triggers a recommended or mandatory evacuation order for our area. We strongly recommend purchasing trip insurance to protect your stay.
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Booking request must include:
1. What brings you to the area?
2. Number of adults/children;
3. Number and description of pets. ($75 fee PER pet)
Signed rental agreement & ID required. Must be min 23 to book (AD mil exception). Respect our neighbors. Excessive Noise will not be tolerated.
- See complete House Rules on Rental Agreement.
Disconnecting internet or security cameras is prohibited and grounds for cancellation with no refund.
Important information
You need to know
Property # 2537005vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a security system, a first aid kit and a deadlock
About the area
Pensacola
Located in Pensacola, this holiday home is in the city centre and near the beach. Saenger Theatre and Museum of Commerce are cultural highlights, and some of the area's attractions include Splash City Adventures and Fast Eddies Fun Center. DeLuna Lanes Bowling Center and Pensacola Children's Museum are also worth visiting. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and horse riding.
University of West Florida - 11 min drive - 8.6 km
Pensacola Bay Center - 12 min drive - 10.7 km
Pensacola Naval Air Station - 23 min drive - 20.4 km
Perdido Key Beach - 32 min drive - 37.1 km
Getting around
Pensacola Station - 7 min drive
Pensacola, FL (PNS-Pensacola Intl.) - 7 min drive
Restaurants
Smalls Sliders - 5 min drive
Circle K - 4 min drive
Whataburger - 4 min drive
Bubba's 33 - 3 min drive
Whataburger - 3 min drive
Frequently asked questions
Is Escape to Five Flags Retreat, Family & Pet Friendly pet-friendly?
Yes, this property allows dogs (limit 3 total).
How much does it cost to stay at Escape to Five Flags Retreat, Family & Pet Friendly?
As of 9 May 2026, prices found for a 1-night stay for 2 adults at Escape to Five Flags Retreat, Family & Pet Friendly on 27 May 2026 start from AU$451, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Escape to Five Flags Retreat, Family & Pet Friendly?
On-site parking is available at the property.
What time is check-in at Escape to Five Flags Retreat, Family & Pet Friendly?
Check-in begins at 4:00 PM.
What time is check-out at Escape to Five Flags Retreat, Family & Pet Friendly?
Checkout is at 10:00 AM.
Where is Escape to Five Flags Retreat, Family & Pet Friendly located?
Located in the heart of Pensacola, this holiday home is within 3 miles (5 km) of University Town Plaza, Splash City Adventures and Brentwood Shopping Center. Fast Eddies Fun Center and Brent Athletic Park are also within 3 miles (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
My friends and I loved this place, it felt like home just in a small amount of days that we were in Pensacola. Great location, it was like 20 minutes to the beach and close to downtown for the nightlife.
Ali J.
Stayed 4 nights in May 2025
Response from VrboOwner on 11 June 2025
We're so glad you and your friends enjoyed your time at Five Flags Retreat. The convenient location does make it the perfect place to stay!
When you walk in it feel comfortable and clean. It was in a great neighborhood and had some awesome places to eat near. Loved the backyard was fenced in so the kiddos could play with our dog. They really have a gorgeous place! We will definitely recommend this rental and hope to be back soon.
Overall stay was great. Great location. Great neighborhood. The other bathroom could use another accessibility for handicapped. But overall, it was a great stay. No issues whatsoever.
Eric G.
Stayed 2 nights in Mar 2025
Response from VrboOwner on 24 Mar 2025
I’m glad you enjoyed your stay! Thank you for your input. Although 3 bedrooms and the two bathrooms are on the ground floor, we do not make any claims that the home or bathrooms are handicap accessible.
Excellent hosts and great property. Even though it was short notice Joy left personalized touches for our family. Hosts are dog people like us, so it was nice to be able to find a rental that would accept our pups as guests.
James R.
Stayed 3 nights in Jun 2022
Response from VrboOwner on 7 July 2022
Thanks for choosing Five Flags Retreat! We hope your family - and fur family - visit again in the future!
This was a nice place to stay with a “homey” feel. “Extras” to make your trip enjoyable— like a french press and grinder (bring your own beans), supplies for the beach, games for the back yard, etc. They were always quick to respond to any questions. The FIve Flags Retreat guide that was sent prior to the trip was well done and very helpful.
Ninita H.
Stayed 6 nights in May 2022
Response from VrboOwner on 31 May 2022
We are so glad you enjoyed your stay at Five Flags Retreat! We look forward to hosting your family again in the future!
We came to Pensacola for the Snow Ball Derby at Five Flags Racetrack. This home was conveniently located. We book trips several times a year and this one was hands down the cleanest we have stayed in. Lots of room for our group!! Very welcoming and felt like home. The Host were great during booking and very responsive. Im sure they would have been accommodating during our stay, but I had no need to reach out for any reason. All the starting necessities were there. Great experience at this rental!! Highly Recommend!!
Brandy D.
Stayed 4 nights in Dec 2024
Response from VrboOwner on 11 Dec 2024
Thank you for the kind words and for choosing Five Flags Retreat! We hope to host you again in the future!
Our host was very gracious and quick to respond. The house was very nice and large enough for our needs. It had everything we needed for our month and half long stay. The location was great, as it was close to everything! The covered porch was one of our favorite spots in the evenings for when it was raining and around the fire pit when it wasn't
William W.
Stayed 48 nights in Oct 2025
Response from VrboOwner on 22 Nov 2025
Thank you for your kind review! We're so glad our home met your group's needs and felt like home. We'd be happy to welcome you back in the future!
Perfect home for a family stay! Lots of space for group activity and private time. Spacious yard for people and dogs. Host is very responsive.
William h.
Stayed 6 nights in Jul 2022
Verified
10/10 Excellent
Shelley L.
29 Dec 2025
Shelley L.
Stayed 5 nights in Dec 2025
About the host
Hosted by Joy Crowe
As a retired military family, and now self employed, we split time between our homes in NC and FL. We are happy to share NC lake life with others seeking a wonderful family vacation spot, Crowe's Nest on the Lake, surrounded by water and amazing sunsets! In Pensacola, FL, we welcome guests to Five Flags Retreat, where you can gather with loved ones and explore all that historic Pensacola (and the nearby beach!) has to offer! We are especially honored to welcome military families that are visiting their loved ones at nearby Fort Bragg, NC or NAS Pensacola. We hope to give our guests the little details that we appreciate when traveling. It’s the little things in life that count!
Why they chose this property
Five Flags Retreat is close to everything! 6 miles to downtown Pensacola, a quick drive of 13 miles to the white sand beaches of Pensacola Beach. Spacious home with four bedrooms, quiet neighborhood and we are pet friendly!
Languages:
English
Premier Host
They consistently provide great experiences for their guests