Welcome to your Southern tropical downtown getaway in the heart of Downtown Pensacola! Walk to all the vibrant attractions on Palafox St., Seville Square, and more, and leave the car in your private parking! The Gregory House, circa 1908, is a historic single-family home gem centrally located in the Seville Historic District in Downtown Pensacola, Florida. Perfect for weddings, family, or couples' vacations, the home features high-end antiques, two gas fireplaces, and plenty of wonder and charm in an Old West Indies-inspired backdrop. The house can host up to 6 guests with four bedrooms and two baths. There is private parking behind the home for up to 6 cars, and it is pet-friendly with screening & a nominal $90 fee for their entire stay (we only accept dogs).
Elegantly appointed, The Gregory House feels like you've stepped into a West Indies-inspired retreat—warm tones, higher-end antiques, and meticulously restored old-world character grace the home. Centrally located and highly walkable, there is spacious private parking so you can leave your car at home and explore on foot. With many historic churches, restaurants, pubs, and beautiful parks nearby, this home is perfect for wedding planning and romantic and family getaways.
The home is nestled in a beautiful, quiet, historic downtown Pensacola neighborhood full of notable charm! Many of the neighbors have lived in the area for years, if not decades, and often you can see them spending their afternoons lounging on their porches, drinking sweet tea or wine. We are a stone's throw from many restaurants, shops, churches, and attractions in our downtown core. It's a fantastic neighborhood to take in the gorgeous 100+ year homes and walk the dog. We are two blocks from Pensacola Bay.
Our prices include all fees. No hidden fees.
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The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
For guests who self-check in, please lock the front door from the inside, exit through the back door (lock bottom lock), and leave the key back in the lock box with the code provided.
Please scrape all stuck-on food, add detergent, and start the dishwasher. Please remove all opened items from the fridge and discard kitchen trash in the black outdoor bin.
Please start a load of towels, set at the hottest setting, add detergent, and start the washing machine.
Failure to complete these may result in a negative review from the host.
We allow a maximum of 6 people
We regretfully cannot accommodate cats due to dander allergies and potential damage to furnishings. Thank you for your understanding.
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Long-term renters welcome
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 first aid kit and a deadlock
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
Frequently asked questions
Is The Gregory House, A Southern Tropical Get Away! pet-friendly?
Yes, this property allows dogs (limit 2 total).
How much does it cost to stay at The Gregory House, A Southern Tropical Get Away!?
As of 8 Apr 2026, prices found for a 1-night stay for 2 adults at The Gregory House, A Southern Tropical Get Away! on 2 Jul 2026 start from £197, 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 The Gregory House, A Southern Tropical Get Away!?
On-site parking is available at the property.
What time is check-in at The Gregory House, A Southern Tropical Get Away!?
Check-in begins at 4:00 PM.
What time is check-out at The Gregory House, A Southern Tropical Get Away!?
Checkout is at 10:00 AM.
Where is The Gregory House, A Southern Tropical Get Away! located?
Located in Seville Historic District, this holiday home is within a 15-minute walk of Seville Square and Pensacola Bay Center. Barkley House and Julee Cottage are also within 10 minutes.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Fantastic host helped me with our entire stay - preparation, early and updated information so we knew what to anticipate, practical instructions, and even help with local to order lost medication. The guest book was clear and concise
This property was perfect for our extended family. The house is in a quiet neighborhood, perfect for walking around or walking to great restaurants. Definitely stay again.
Great location. Front patio tables were awesome to gather and eat our meals. Kitchen was well stocked. Bedrooms comfortable and clean. Only negative is that the upstairs bathroom is not practical for adults (micro-sized shower and unusable toilet location…have to duck down to use sink) so really only one working bathroom for adult sized guests. We enjoyed our stay regardless and the host was very responsive and pleasant!
Close to several unique restaurants and only a few blocks from downtown Pensacola. Plenty of common space for large groups. Nice front porch and parking in driveway for several cars. The only slightly negative comment is the bathroom in the upstairs bedroom is hard to maneuver in because of the sloped ceilings.
We were in town for our daughter's wedding and enjoyed staying at the Gregory House, located in the center of the Historic District. The home is charming, with plenty of parking in the rear to accommodate wedding guests that stopped by to visit. The upstairs provided a wonderful space for our daughter to get ready and dressed prior to the wedding, which was held at the nearby Basilica.
Location and property were very nice. Communication was great. The parking in back of house was convenient and spacious. All the Antiques located throughout each room were designed and picked with care. The kitchen had all the conveniences and was spacious.
I can’t say enough good things about our stay here. We absolutely love downtown Pensacola and were pleased we could walk to Palafox and all of downtown so easily. Drive to the beach was easy and having a nice quiet location to stay was perfect.
Absolutely incredible stay at the Gregory House! For it being built in 1908, it’s completely silent when you move around, the floors and stairs do not creak or squeak. The AC works incredibly well, and the showers have great water pressure. If you’re super tall, you probably need to stay downstairs and not in the upstairs area, the bathroom is short-friendly. The host was quick to communicate and very kind. The house was spotless. We definitely plan on staying here again if we can!
This is a great location !! Easy walk to shopping and restaurants. Loved the porch area for outdoor relaxation !! Would definitely book this rental again. Easy check in and check out
Beautifully restored historic house. Easy walk to parks and downtown. Upstairs area of limited use due to cramped bathroom and lack of curtains to control light. The rest of the house has great modern features. Ample off street parking.
We had a seamless experience at this VRBO. It is a prime location downtown within walking distance of the historic district, restaurants, and shops. The host communicated well and the house was well stocked so that we didn't need to buy any of the basics. It was fun to stay in a unique old house and experience living in downtown Pensacola.
We loved the location and the cute train and Christmas show right in the front yard on the weekend. It was precious. Fantastic time! Only feedback would be maybe consider a bigger sofa in the living room. Other than that, it was perfect.
We were in town for a High School graduation, to visit with nearby family, and to take in the sights and a few restaurants. The Gregory House was PERFECT for our needs. Having owned an older home, it was nice to experience the familiarity in this home. G****** was great to work with and the self-checkin and checkout process was very convenient.
Scott M.
Stayed 4 nights in May 2023
Verified
6/10 Okay
Eddy M.
6 Feb 2025
Liked: Check-in, location
Disliked: Cleanliness, listing accuracy
Floors were dirty.
Floors were dirty, grandsons feet were filty.
Eddy M.
Stayed 6 nights in Jan 2025
About the host
Hosted by Gloria
Why they chose this property
The home is nestled in a beautiful quiet, landmark historic downtown Pensacola neighborhood full of notable charm! Many of the neighbors have lived in the area for years, if not decades, and often you can see them spending their afternoons lounging on their porches drinking sweet tea or wine. We are a stone's throw from many restaurants, shops, churches, and attractions in our downtown core. It's a fantastic neighborhood to take in the gorgeous 100+ year homes and walk the dog. We are two blocks from Pensacola Bay.
Languages:
English, Spanish
Premier Host
They consistently provide great experiences for their guests