A family-friendly stay in the heart of Gulfport awaits you at this holiday home. Within just a 10-minute stroll, you'll find Gulfport Beach and Gulfport Casino. Highlights at this holiday home include a kitchen, a washer/dryer and free WiFi. .Home features a fireplace, a patio and a living room. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A dining area, a fenced private garden and a Smart TV are also available. .This pet-friendly holiday home offers a games room, a garden and barbecues. Plus you'll find laundry facilities. .Attractions within a 10-minute drive of this Gulfport holiday home include St. Petersburg - Clearwater Beaches and Salvador Dali Museum.
Gulfport Tuesday Fresh Market - 6 min walk - 0.6 km
Gulfport Beach - 6 min walk - 0.6 km
Gulfport Casino - 8 min walk - 0.7 km
Island Community Theatre - 4 min drive - 1.8 km
John's Pass Village & Boardwalk - 17 min drive - 12.6 km
Getting around
St. Petersburg, FL (SPG-Albert Whitted) - 10 min drive
Restaurants
McDonald's - 18 min walk
O'Maddy's - 10 min walk
Dunkin' - 9 min walk
Pia's Trattoria - 7 min walk
Stormrunners Tavern - 9 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House
The Wine Cellar in Gulfport Beach is a two-bedroom one-bathroom luxury home designed to immerse the guest in a Tuscany-style vacation on the beach. Conveniently located 1 block from the main street and 4 blocks from Gulfport Beach. Boasting over 1200 sf of home and indoor-outdoor living the Wine Cellar has a bar for 2, a living room for 6 with a 55" TV. There is an enclosed backyard with a privacy fence. The outdoor patio has a barbecue and a gas fire-pit umbrella and Adirondack chairs. The enclosed 450 SF patio has 4 fans, a dining table with wine barrel chairs, a living room set, a 55" TV, in wall fireplace and games like Life size Jenga and Connect 4.
Guests will experience a great night's sleep with a queen memory foam bed in the master bedroom and a hybrid memory foam coil bed in the guest bedroom. Beds are fitted with high thread count sheets wrapped in a luxurious down comforter, 4 medium density pillows, throw blankets as well as three plugs, two USB ports, and reading lights at each bedside. The Master Bedroom has a partial view of the water as well as blackout blinds.
The Wine Cellar can accommodate 6 adults. 2 adults per bedroom, and 2 Adults on the queen sleeper sofa.
All guests are required to register with Check-in Software when emailed to them after the reservation has been booked. At any time the owners can request government ID of the guest making the reservation in order to establish their Identity.
Guests will be sent a copy of the Guest Rental Agreement and will agree to it by not canceling the reservation.
The kitchen comes stocked with dishware and cups to spare, a 14-piece cooking set, baking pans, spices, coffee maker, sugar cream, coffee, blender, toaster, plenty of towels, and cooking utensils.
Washer, dryer, detergent provided
Sit back and relax in the spacious enclosed patio with an oscillating fan while you barbecue your meals on your own grill in your private dog-friendly enclosed backyard.
You will be provided with beach towels for use at the beach and can rent beach chairs & umbrellas upon request.
To ensure the security of our guests we have fitted the property with 10 motion sensor lights, 8 security cameras, and 4 microphones at the doorways of the property. All check in's will be reviewed via security cameras.
To ensure the comfort of our guests we have provided central air conditioning and ceiling fans in every room. The thermostat is locked between 70 and 80 degrees. please call your host for any thermostat special requests. The water is purified through a whole house filter, water softener and de-scaler.
The Wine Cellar is a two-bedroom one-bath with a full kitchen. You can enjoy the outdoors with the propane fire pit provided or sit back in the large enclosed patio enjoying the game room. Your dog will enjoy a private enclosed yard just for them. The Wine Cellar has a four-car driveway and plenty of street parking in a well-lit safe area. The driveway is big enough to fit an RV, Boat, or trailer but there are additional fees for such parking.
You can also rent another 2 bedrooms one bath Luxury unit called the "Beach House" next store if you need to book up to an additional 6 guests.
Gulfport Beach is a hidden treasure in south St Pete. We have our own beach on the inter-coastal with professional volleyball courts on white sand. You can just see the beach down the street if you look from the bedroom window or the front of the home. Wood Ibis Park has a scenic lake walk one block from the house. Our Main street is full of shops, restaurants, breweries, and bars. We are two blocks off the main street in a safe and quiet neighborhood.
You are in the heart of the Gulfport Community in WALKING distance to everything you will want to do for your vacation.
= Gulfport Fresh Market is held every Tuesday morning one block away on the Main Strip.
= Gulfport Art walk is held First Friday and Third Saturday every month.
= Two local Markets one block away
= Too many amazing owner-run breakfast, lunch, dinner restaurants, and bars to count.
= Coffee shops, Kava Shops, Vegan Deli’s
= Eclectic shops with local art and keepsakes
= Community services like the library, the senior center, recreation center, the playhouse, and the dog park.
= Basketball courts, volleyball courts, the pier, the beach.
= City of Gulfport Municipal Marina
= Gulfport Historical Museum
= The Gulfport Casino which is a Dance hall.
= Wood Ibis Park, Hoyt Park, Clymer Park, Clam Bayou Nature Park
= Twin Brooks Golf Courses.
= Gecko Art Show, Gecko Art Crawl, and Gecko Ball all held in August.
= "Beach Bums" Volleyball tournaments throughout the year.
= First Fridays are held in downtown St. Pete monthly where you can walk the city with open containers. Downtown is a 15-minute uber ride from Gulfport.
Plenty of private parking and street parking. You will walk to everything once you get here. We have two markets one block from the home. The Gulfport strip is one block away so you don't have to worry about walking too far to get to the fun.
Each reservation will be charged a one-time $50.00 Administrative Fee.
"Pet Fee" on all booking applications are referring to dogs. All other animals must be discussed with property management for approval. There will be up to a $700 pet fee for any other animal brought on the property other than dogs.
Local ordinances allow a limited number of 30-day minimum stays. Please call Jason's Vacation Rentals for further questions regarding your seasonal rental.
FRAUD ALERT! Jason’s Vacation Rental does not rent directly to first-time renters. We do not ask for checks, wire transfers, or credit cards over the phone. First-time renters must book through the major booking applications for their entire stay. Please notify Jason’s Vacation Rentals if this property is being solicited to you and requesting direct payment..
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
First aid kit
Fire extinguisher
Deadbolt lock
General
Bicycles
Garden
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21
Check-out
Check-out before 11:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
All Guests are charged a $50.00 Mngmnt fee. Cancelations incur a $150.00 fee. VRBO does not fully refund the Lodging tax and guest service fee.
The owner of the card which booked the reservation must be present at check-in or the reservation will be canceled with no refund.
Pet owners must vacuum all pet hairs on floors, patios, chairs and couches. "Pet Fee" refers to Dogs, All Other Animals are up to a 700 pet fee.
Pets
Pets are welcome
Only dogs are allowed
Maximum 4 pets
Restrictions apply
For more information, you can reach out to the property at the number on the booking confirmation
Service animals are exempt from fees.
Note from host: Monthly Pre Chck-In $50 per pet Post Chck-In $100
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Smoking only allowed on patio
Important information
You need to know
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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a private host, not a professional engaged in trade or business.
On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.
We should mention
To make arrangements for your pet, contact the property directly using the information on your booking confirmation.
Property is also known as
Jason's Wine Cellar Steps Gulport Beach Main Street House
Jason's Wine Cellar Steps Gulport Beach Main Street Gulfport
Jason's Wine Cellar Steps Gulport Beach Main Street House
Jason's Wine Cellar Steps Gulport Beach Main Street Gulfport
Jason's Wine Cellar Steps Gulport Beach Main Street
Jason's Wine Cellar Steps From Gulport Beach Main Street
Jason's Wine Cellar Steps From Gulport Beach Main Street
Jason's Wine Cellar Steps from Gulport Beach Main Street.
Jason's Beach Wine Cellar Steps From Gulport Beach Main Street
Jason's Beach Wine Cellar Steps from Gulport Beach Main Street.
Frequently asked questions
Are there any beaches close to Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House?
Yep, Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House is a short 8-minute walk from Gulfport Beach.
Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find water sports equipment and motor boats.
Does Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House have a pool?
No, this holiday home doesn't have a pool.
Is Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House family-friendly?
You bet! With amenities such as an arcade and laundry facilities, as well as highchairs and children's dinnerware, it's no surprise that Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House is a winner with our family travellers.
Is there a free airport shuttle available at Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House?
No, Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House does not offer an airport shuttle service.
What time are check-in & check-out at Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House?
Check-in begins at 4:00 PM. Check-out time is 11:00 AM.
Gulfport Beach Vacation Rental, 2 Bedroom WINE CELLAR THEMED, 5 Star Beach House Reviews
Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 78 out of 85 reviews
10 - Excellent
78
Rating 8 - Good. 5 out of 85 reviews
8 - Good
5
Rating 6 - Okay. 2 out of 85 reviews
6 - Okay
2
Rating 4 - Poor. 0 out of 85 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 85 reviews
2 - Terrible
0
9.8/10
Cleanliness
Reviews
10/10 Excellent
Barry J.
12 Mar 2026
Liked: Cleanliness
Location, Location, Location. Couldn't get any better for accessing the ambiance of Gulfport. Downtown, dog park and beach all within walking distance. Owner and property manager very responsive to your requests! Lots of amenities. Cannot wait for another opportunity to visit here.
Barry J.
Stayed 72 nights in Dec 2025
8/10 Good
James S.
17 Oct 2025
Liked: Cleanliness
Stay was okay. Porch was dirty and the TV in the porch didn't work, some light bulbs were out and dead batteries in TV remotes. Inside was clean, comfortable, and it had nice amenities. Nice quiet neighborhood, close to everything. Preserve/ beach are directly down the street.
James S.
Stayed 5 nights in Oct 2025
10/10 Excellent
Karen H.
21 Sept 2025
Liked: Cleanliness
Great location. Very clean and comfortable.
Karen H.
Stayed 3 nights in Sep 2025
10/10 Excellent
Andy R.
23 Jul 2025
Liked: Cleanliness
Recently moved from Gulfport and wanted to come back down to visit friends and neighbors. Loved staying at Wine Cellar. Great location, clean, and comfortable stay. Communication with host was smooth and the check in / check out process easy. Considering coming back to stay within a few weeks
Andy R.
Stayed 12 nights in Jul 2025
6/10 Okay
john s., Charles Town WV
12 Jun 2025
OK stay
john s.
Stayed 14 nights in May 2025
10/10 Excellent
Amanda M.
20 May 2025
Liked: Cleanliness
We had a nice stay.
The duplex was nice. Was everything we needed. We don’t drink wine, but the ambiance was nice. Doing a bit of laundry and cooking breakfast was wonderful. Walking to restaurants and library was great. Thanks for a great stay!
Amanda M.
Stayed 6 nights in May 2025
10/10 Excellent
Walter T.
22 Apr 2025
Liked: Cleanliness
Perfect place to stay
Place was just as advertised! Had everything we needed and was centrally located to everything. Would stay again and highly recommend!
Walter T.
Stayed 3 nights in Apr 2025
10/10 Excellent
Verified traveller
22 Apr 2025
Liked: Cleanliness
Great place to stay
We have stayed in the Wine Cellar for several years and had a great stay again this year. Great location, comfortable and well equipped kitchen. Already reserved for next year.
Verified traveller
Stayed 7 nights in Apr 2025
6/10 Okay
Helen M.
26 Apr 2024
HM
Good.
Need decent wine glasses.
Helen M.
Stayed 4 nights in Apr 2024
10/10 Excellent
Tracey B.
22 Apr 2024
Liked: Cleanliness
Great stay!
The host communicated well and was attentive. The house was just what we wanted and had all conveniences and supplies. The area was beautiful ...safe, friendly and had a lot of restaurants and shops within walking distance. If you're visiting Gulfport, I highly recommend you stay at Jason's Wine Cellar. You won't be disappointed!
Tracey B.
Stayed 8 nights in Apr 2024
10/10 Excellent
Verified traveller
14 Apr 2024
Liked: Cleanliness
Always great
Our third year in this unit. Great location. Easy walk to downtown but quiet neighborhood. 10-15 min to St Pete Beach. Comfortable space for relaxation and kitchen well supplied.
Verified traveller
Stayed 7 nights in Apr 2024
10/10 Excellent
Keith D.
14 Apr 2024
Liked: Cleanliness
“The Game House”
We loved our stay here in Gulfport! We booked this house to be near the races in Bradenton and near Clearwater. We had no clue Gulfport was a thing. Our first night we walked to a nearby burger/pizza joint and discovered Gulfport. What an amazing place! The food selections were great! There was a beach there to top it all off. Gulfport was so cool that we never even made it over to Clearwater. This was right in the middle of spring break and the beach wasn’t even crowded at all there!
The house was fantastic! We have done tons of Vrbo over the years and this was the best quality of all of them. There was extreme attention to detail and it seems that everything was thought of to make our stay as easy as possible. Our twin 5 year old daughters loved the screened in patio with all the games and so did we. The house was very clean and everything was of nice quality and construction. We for sure want to rent this property again due to its close walking distance to Gulfport and the quality of property. Our girls have been asking about what they call “The game house” ever since our stay a week ago.
Our next stay can’t come soon enough!
Keith D.
Stayed 6 nights in Apr 2024
10/10 Excellent
Tracey L.
3 Jan 2024
Liked: Cleanliness
Great Staycation!
This property was perfect for my husband and I for a staycation for Christmas. Very clean, description was extremely accurate, great location to walk downtown and along the beach. We will definitely stay here again!
Tracey L.
Stayed 5 nights in Dec 2023
10/10 Excellent
Sharon W.
27 Nov 2023
Liked: Cleanliness
Wine Cellar does not disappoint!!
We loved staying at this place it was local to everything and was very well kept! You can see everything that you need is there and the communication is awesome! There are a lot of extras that you don’t normally get at anywhere else in a VRBO. Very very nice.
Sharon W.
Stayed 5 nights in Nov 2023
10/10 Excellent
Marla M., OHIO
5 Sept 2023
Liked: Cleanliness
Family Weekend
The Wine Cellar was an awesome place to stay. Lots of fun activities and full of amenities. The location is perfect for exploring Gulfport.
Marla M.
Stayed 4 nights in Aug 2023
10/10 Excellent
N G.
17 Aug 2023
Liked: Cleanliness
Quiet Place
Underrated location. Gulfport is very friendly and convenient spot. Many different places to eat and drink within walking distance. The Gulfport beach area is small but charming with an awesome park area to sit and relax. The unit was clean and had all the amenities you need highlighted by the classic sun room. We enjoyed our stay and would consider this location again.
N G.
Stayed 3 nights in Aug 2023
10/10 Excellent
Chrissifer R.
23 Jul 2023
Liked: Cleanliness
1st beach trip
Enjoyed everything about our stay.
Chrissifer R.
Stayed 5 nights in Jul 2023
10/10 Excellent
Nicole L.
26 Jun 2023
Liked: Cleanliness
Perfect location!
The property was very clean and everything that we needed. When we had to get in touch with the owner they respond quickly. The location is perfect! Just a short walk to the amazing shops and the beach!
Nicole L.
Stayed 4 nights in Jun 2023
10/10 Excellent
Hali R.
25 Jun 2023
Liked: Cleanliness
Great Girls Weekend
Had a lovely weekend with my girlfriends! Muchhh cuter than the pictures show and love the neighborhood. Close enough to walk to restaurants and bars in Gulfport, but far enough away that it was quiet at night! Jason replied to my messages quickly and everything went smoothly! Would definitely recommend to a friend
Hali R.
Stayed 2 nights in Jun 2023
10/10 Excellent
Anthony V., Miami, FL
21 Jun 2023
Liked: Cleanliness
Pleasant Surprise
The home and neighborhood were perfect
I had to work and my Father stayed to explore the area with the dog
We enjoyed the beach close by and all the wonderful restaurants just blocks away
Definitely recommend!
Anthony V.
Stayed 4 nights in Jun 2023
10/10 Excellent
Stefan P., Grand junction co
16 Jun 2023
Liked: Cleanliness
Beautiful home
The property was so nice. And in a great area. We had one small issue and they made it right immediately! Thank you!!!
Stefan P.
Stayed 6 nights in Jun 2023
8/10 Good
Benja P.
7 Jun 2023
Liked: Cleanliness
Cute little place
Smaller than I thought it would be, didn't realize it was a duplex either. Overall it was ok.
Benja P.
Stayed 3 nights in Jun 2023
10/10 Excellent
Cheryl R., Wesley Chapel, FL
30 May 2023
Liked: Cleanliness
Love this place
Loved this adorable house. Walking distance to restaurants, live music, beach on the bay. Five miles to the beautiful Gulf of Mexico beaches. House had everything we needed and more. Pet friendly, our dogs enjoyed the outside screened in porch as did we. We will be back for sure !
Cheryl R.
Stayed 4 nights in May 2023
10/10 Excellent
Tammy C.
25 May 2023
Liked: Cleanliness
Everything it says it is and more!
Clean and comfortable with all necessities and more. All linens and towels provided. Washer and Dryer. Well equipped kitchen. Great screened in porch, games, TV, sofa and chairs, table for a meal. Great place for morning coffee. Property Manager responsive. Would definitely stay again!
Tammy C.
Stayed 3 nights in May 2023
10/10 Excellent
Teresa B.
11 May 2023
Liked: Cleanliness
Family weekend
The property was amazing. Centrally located to many places for fun, fan, and entertainment. Close to various beaches and fully equipped. I will definitely stay here again.