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Guesthouse holiday rentals in Southside, Jacksonville

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Southside, Jacksonville guesthouses

Family-Friendly guesthouses

Guesthouse in Beaches
4.71 out of 5 average rating, 212 reviews

Cozy Cottage Studio, Walk to Beach

LaraRating, 5 stars11 months ago
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!
Top Guest favourite
Private room in Ponte Vedra
4.97 out of 5 average rating, 107 reviews

Private Beach Access - Charming Villa

DionneRating, 5 stars1 month ago
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.
Superhost
Guesthouse in St. Augustine
4.8 out of 5 average rating, 191 reviews

Sea Turtle Beach Cottage

DarlaRating, 5 stars1 month ago
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.
Guest favourite
Guesthouse in St. Augustine
4.91 out of 5 average rating, 577 reviews

Captain's Quarters Tiny House

KharisRating, 5 stars4 days ago
This was the perfect amount of space for us, we had a lovely stay and enjoyed the location and privacy very much.
Guest favourite
Guesthouse in Jacksonville
4.74 out of 5 average rating, 451 reviews

Pool House-2 Bdr/1Ba Apt-Pool-Sleeps 5-Pets OK

CalebRating, 5 stars1 month ago
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.
Top Guest favourite
Guesthouse in Springfield
5 out of 5 average rating, 32 reviews

Lovely Guesthouse in the Up-and-Coming Springfield

Ron&NormaRating, 5 stars1 month ago
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!
Guest favourite
Guesthouse in Orange Park
4.91 out of 5 average rating, 167 reviews

Graceful Southern Guesthouse + Outdoor Living Area

YvetteRating, 5 stars3 weeks ago
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.
Guest favourite
Guesthouse in Riverside
4.95 out of 5 average rating, 151 reviews

The Funk House-A Retreat

BarbaraRating, 5 stars1 month ago
Very nice location, spacious, low traffic and safe streets.

Guesthouses with a patio

Superhost
Guesthouse in Jacksonville
4.82 out of 5 average rating, 55 reviews

The Little House

Ryan JosephRating, 5 stars1 month ago
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!
Top Guest favourite
Guesthouse in Beaches
5 out of 5 average rating, 211 reviews

Tropical guest house a few blocks from the beach

MelissaRating, 5 stars2 days ago
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.
Guest favourite
Guesthouse in Jacksonville
4.93 out of 5 average rating, 196 reviews

Adorable 2 Bedroom Cottage

RobertRating, 5 stars1 week ago
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.
Top Guest favourite
Guesthouse in San Jose
4.98 out of 5 average rating, 88 reviews

Transforms, Full Kitchen/bath, Centrally located

AntonioRating, 5 stars4 days ago
Very good, everything perfect. Thank you.
Top Guest favourite
Guesthouse in St. Augustine
4.95 out of 5 average rating, 380 reviews

The Garden Casita in St. Augustine Florida

AydonRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Murray Hill
4.9 out of 5 average rating, 313 reviews

The Moody Loft (Murray Hill)

LisaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Guesthouse in Jacksonville
4.79 out of 5 average rating, 14 reviews

Welcome to Rome

JacklynRating, 5 stars1 week ago
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!
Top Guest favourite
Guesthouse in St. Augustine
4.95 out of 5 average rating, 106 reviews

Historic Downtown Studio

SergioRating, 5 stars3 weeks ago
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

Guest favourite
Guesthouse in St. Augustine
4.9 out of 5 average rating, 250 reviews

SaraCasa - First Floor House 2Br/1.5Bath

JeremyRating, 5 stars1 week ago
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!
Top Guest favourite
Guesthouse in Avondale
4.99 out of 5 average rating, 105 reviews

Charming Pet-Friendly Guesthouse in Avondale

WhitneyRating, 5 stars3 weeks ago
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!
Top Guest favourite
Guesthouse in Avondale
4.96 out of 5 average rating, 85 reviews

Private Studio Carriage House

ElizabethRating, 5 stars4 weeks ago
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!
Superhost
Guesthouse in Springfield
4.88 out of 5 average rating, 293 reviews

Downtown Jacksonville Historic District

StephenRating, 5 stars2 weeks ago
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.
Top Guest favourite
Guesthouse in St. Augustine
4.97 out of 5 average rating, 330 reviews

“Little Pink House”-hidden gem in the 💗 of Uptown

JuliaRating, 5 stars1 week ago
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!
Superhost
Guesthouse in St. Augustine
4.88 out of 5 average rating, 460 reviews

Romantic Island Studio • Walk & Bike to Downtown!

StacyRating, 5 stars1 week ago
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!
Top Guest favourite
Guesthouse in Avondale
4.96 out of 5 average rating, 161 reviews

Stylish Bungalow Near Dining,Parks & Entertainment

NaomiRating, 5 stars1 week ago
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.
Guest favourite
Guesthouse in Springfield
4.96 out of 5 average rating, 113 reviews

Spacious 2/1 in historic walkable neighborhood

SandraRating, 5 stars3 weeks ago
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

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  2. United States
  3. Florida
  4. Duval County
  5. Jacksonville
  6. Southside
  7. Guesthouse rentals