
Guesthouse holiday rentals in Southside, Jacksonville
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Top-rated Guesthouses in Southside, Jacksonville
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
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Popular amenities for Southside, Jacksonville guesthouses
Family-Friendly guesthouses

Cozy Cottage Studio, Walk to Beach
Was able to work from the cottage during the day and enjoy evenings and weekend with my friend in the area. Very clean great basic kitchen amenities for coffee, breakfast, lunch. Exactly what I needed!

Private Beach Access - Charming Villa
I can’t say enough good things about the Villa. From the moment we arrived, everything exceeded our expectations. The place was spotless, beautifully designed and equipped with all the thoughtful touches that made it feel like home. Rachel was welcoming, responsive, and genuinely committed to making our stay comfortable. Whether you’re looking for a peaceful getaway or a convenient homebase, this place is perfect and it’s steps away from the beach. I would absolutely stay here again and highly recommend it to anyone visiting the area.

Sea Turtle Beach Cottage
The sea turtle cottage is absolutely perfect for a beach getaway. The host is extremely nice and was available if needed. The ocean is just a few steps thru the back yard onto the walkway that deposits you directly onto the pristine white beach. No dunes to walk thru, just a few stair-steps. The cottage is quiet, updated, clean and tidy with a very comfortable king bed. Plenty of towels and linens, toiletries and a fully equipped kitchen. It rained a bit during our stay, plenty of dvd movies, tv and books kept us occupied. There are restaurants, shops, gas and groceries nearby. We even had a pizza delivered for a late night snack. We would definitely stay at the sea turtle again without hesitation.

Captain's Quarters Tiny House
This was the perfect amount of space for us, we had a lovely stay and enjoyed the location and privacy very much.

Pool House-2 Bdr/1Ba Apt-Pool-Sleeps 5-Pets OK
requested early check in and was given an earlier time(fantastic).I was meet within 5 minutes of arrival by the host to give me access to an ethernet connection. next day asked for linens and was brought them same night 10 minutes or so (fairly late also) awesome location anywhere you can think of within 15 minutes your there. pool, lawn, house well maintained. Gregory went beyond my expectations with his personality, hosting, personal accommodations.. had a great time.

Lovely Guesthouse in the Up-and-Coming Springfield
I had a great stay at Mateus’s place! The apartment was clean, comfortable, and exactly as described in the listing. The check-in process was smooth, and Mateus was responsive and helpful throughout my stay.I’d definitely recommend this Airbnb to anyone visiting the area!

Graceful Southern Guesthouse + Outdoor Living Area
If come across this place and it’s available, BOOK IT! This place is comfortable, relaxing, cozy. It reminds me of the perfect place to stay; it has a yoga spa retreat atmosphere. If you’re looking, thinking, pondering, wondering, considering, contemplating, eyeing renting this place, just book it you won’t regret. I stayed here with my cousins from Maryland, they would have stayed indoors the entire weekend if it weren’t for our nephews graduation and their party (at my sisters house). Absolutely no regrets.

The Funk House-A Retreat
Very nice location, spacious, low traffic and safe streets.
Guesthouses with a patio

The Little House
Beautiful, quiet, clean, private, well appointed unit with all the amenities of home, and then some. Easy check in and access, extremely agreeable and flexible host. I will stay here again!

Tropical guest house a few blocks from the beach
Jeff’s place is close to two separate hot spots in Jacksonville’s beach area. Atlantic Beach was a beautiful 1mile beach walk and Neptune Beach with a local musical amphitheater was .5 mile in the opposite direction. We loved the nestled home - full of tropical foliage and palm trees. Sitting out on the patio each morning was a blessing. The bedroom is lofted so expect some steeper stairs, but I absolutely loved it. Perfect for our short weekend. Try the poké nachos over at The Local in Atlantic Beach.

Adorable 2 Bedroom Cottage
The place is great. Jose is very friendly and responsive. Place is relaxing and very clean. It is great to have your own AC in each room. Yard is beautiful and nice to hang out in.

Transforms, Full Kitchen/bath, Centrally located
Very good, everything perfect. Thank you.

The Garden Casita in St. Augustine Florida
AMAZING HOST! Very responsive and helpful. Great location and very peaceful. This is hands down one of the best Airbnb’s my wife and I have stayed at. Will be back in the future.

The Moody Loft (Murray Hill)
Where do I begin. Cameron’s place was great. I had a small hiccup on arrival but it was quickly sorted out. He went above and beyond for me. I’m prone to getting hot and he even went out and bought me a fan!!! I felt very comfortable there, especially being a single woman traveling alone. Ty Cameron!

Welcome to Rome
It such a great little escape to Rome! My favorite part was the hot tub and the decor. We will definitely be back for another stay!

Historic Downtown Studio
This was my 1st time in St Augustine. I travelled with my partner for Memorial Day Weekend to enjoy the city. The location was perfect, walking everywhere just minutes away from Historic downtown. The Airbnb was spotless, great parking. Overall a great experience. I would definitely recommend to anyone going to St Augustine.
Guest house rentals with a washing machine and dryer

SaraCasa - First Floor House 2Br/1.5Bath
After I booked the place Jason periodically sent info as the check in date approached as if I hired him to plan my trip. The property has upscale amenities and furnishings. The property is extremely comfortable and able to accommodate more than advertised. Location is so good I will need 6 stays to try and see everything just in walking distance. My family left packing all clean clothes bec the laundry unit was incredible. The unit in its entirety was planned in detail for comfort. The AC worked like a beast which is extremely important in Fla. I can't say enough about this place. I am a tough person to please and am willing to use every character the app allows to attempt to communicate Jason's hospitality, hard work, and generosity to provide a great experience for his guests. If a guest gives him less than all five's they are being calculated in trying to keep the property more likely to be available for themselves for their next trip. Will rent again. Thank you Jason!

Charming Pet-Friendly Guesthouse in Avondale
The guesthouse is a great home away from home & Chris goes above & beyond to make sure our stay is comfortable & enjoyable. The guesthouse is always spotless, it’s in a great location and the backyard is always enjoyed by our dog. This was our second stay at the guesthouse & we will certainly be back! Thanks Chris!

Private Studio Carriage House
I stayed here for some quiet time at the end of a long trip, and it was perfect. Peaceful, well-stocked, and in an amazing location — close couple minutes walk to the restaurants, shops, as well as nearby beautiful walks near the river. Steve and his daughter were incredibly kind and responsive. Don’t hesitate to book if you’re thinking about it!

Downtown Jacksonville Historic District
We enjoyed our stay at this location. If you're looking for a place close to UF Health, this is a great option. Just be cautious when driving through the back lot — we believe that's where we picked up two nails in our tires. Aside from that, it was a great place to stay while working at UF Health on 8th Avenue. The kitchen, bathroom, bedroom, and living room were all clean and well-maintained. We also enjoyed sitting on the balcony, even though it was quite hot during our stay.

“Little Pink House”-hidden gem in the 💗 of Uptown
From the moment we walked into the little pink cottage we felt right in our element. As if it was made for us. (My daughter and I). The coziest little cottage, perfect in every way. So much attention to detail, from the comfortable bed to the decor, we didn’t want to leave. The backyard is wonderful, a country feel and very private. We loved the pool, the outdoor sitting areas perfect for relaxing, and we rode the bikes around the neighborhood, a true delight. The location is like out of a Hallmark holiday movie.. adorable bungalows and cottages lining up the blocks in an old St Augustine picturesque neighborhood. We walked the 15 minutes to George St, and it was a delightful little walk.. with cafes, restaurants and cute little shops all around. So much to do and see, our only regret is that we didn’t stay longer. But we will be back!

Romantic Island Studio • Walk & Bike to Downtown!
A cozy space in the middle of a quiet neighborhood, I’d recommend this to anyone who wants a comfortable little getaway. My husband and I enjoyed walking thru the neighborhood and even into the downtown St Augustine area. Everything was easy to get to and the host was very responsive and helpful!

Stylish Bungalow Near Dining,Parks & Entertainment
Amazing place, the hosts were quick to respond to any questions we had. Cute little Airbnb to relax in. Would recommend, stores and restaurants are close by.

Spacious 2/1 in historic walkable neighborhood
We had a wonderful stay at Jennifer's place. From the beginning she was quick with her responses. The actual location of the property was a bit difficult to navigate but only because we came in so late at night. The instructions were right on point and getting inside was easy with the keyless entry. We had everything we needed while there. The pool and foosball table were perfect for the boys. They had a blast the entire weekend. We would definitely stay again if we are ever back in Jacksonville.
Quick stats about guesthouse rentals in Southside, Jacksonville
Total rentals
20 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Destinations to explore
- Rentals with a hot tub Southside
- Rentals with beach access Southside
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- Private suite rentals Southside
- Pet-friendly rentals Southside
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- Apartment rentals Southside
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- Rentals with a fireplace Southside
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- TIAA Bank Field
- Old A1A Beach
- Boneyard Beach
- Kathryn Abbey Hanna Park
- Amelia Island State Park
- Fountain of Youth Archaeological Park
- Crescent Beach
- Butler Beach
- Guana Reserve Middle Beach
- North Beach Guana River Preserve
- Lightner Museum
- Palm Harbor Golf Club
- Dungeness Beach
- St. Augustine Alligator Farm Zoological Park
- Matanzas Beach
- MalaCompra Park
- Eagle Landing Golf Club
- Bent Creek Golf Course
- Driftwood Beach
- St. Marys Aquatic Center
- Ravine Gardens State Park
- Vilano Beach