
Guesthouse vacation rentals in Southside, Jacksonville
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Top-rated guesthouse rentals in Southside, Jacksonville
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Southside, Jacksonville guesthouse rentals
Family-friendly guest house rentals

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
Rachel’s beach cottage offers incredible exclusivity and privacy in a beautifully appointed garage loft that is perfect for a weekend getaway. Rachel is super hospitable offering easy instructions and quick response times. As someone who travels extensively, Rachel’s place is a true hidden gem. 5 stars!

Private Apartment
This was the perfect place for my mom and I. The place was spotless, and well stocked with everything you need. Thought we would need to pick up a few essentials like coffee creamer, water, shampoo, and other items that we like to have, but didn’t even need to do that because the apartment was so well stocked. Would definitely recommend! Thank you!

Pool House-2 Bdr/1Ba Apt-Pool-Sleeps 5-Pets OK
Gregory is a great host! The place was perfect if you have dogs. The back yard is huge and feels very private. I look forward to staying again!

Lovely Guesthouse in the Up-and-Coming Springfield
The apartment had everything I needed: the kitchen was fully stocked with items used for cooking, the bath had plenty of towels and soaps, the bed was comfortable and the porch was private and comfy. Mateus and his friend were very kind to help me unload my car, and Mateus also checked me in and gave me information about the rental.
Guest house rentals with a patio

The Little House
I had a last minute visit to see my daughter, son in law and grandsons and needed a place quickly. Maria went above and beyond to accommodate my last minute reservation. She responded to my needs very quickly. Her place was so lovely and clean. I can't wait for my next visit and I will definitely be staying at her place each time. Thanks Maria you are a true gem!!!

Adorable 2 Bedroom Cottage
Jose!! You need more coffee cups. ;) My wife and I had to share one. That is the ONLY thing we could say about the place. The yard was nice. Place was spotless. Put some Diet Cokes in the fridge! Would use it again. Loved it.

Comfortable and Gently Disney.
Perfect place for our family. The kids absolutely loved everything with all the toys and a tent ⛺️ to sleep inside. Jeri the host was so helpful and extremely kind. We would absolutely visit back!!

Transforms, Full Kitchen/bath, Centrally located
This is a beautiful, clean, and quiet location. It is within walking distance of the main street, where there are pharmacies, a supermarket, and several restaurants. The host is very friendly and helpful.

Boone Park Studio
I had a wonderful stay at this charming backyard cottage. Surrounded by beautiful, old Florida trees, it felt like a peaceful retreat. The neighborhood is quiet, with parks nearby and a street full of restaurants and coffee shops nearby. Highly recommend!

Farmhouse luxury, you'll never want to leave
Great host, beautiful property we enjoyed our stay!!

The Moody Loft (Murray Hill)
I can honestly say that Cameron’s place is one of my favorite AIRBNB’s I’ve ever stayed in! I felt right at home and it had everything I needed for my trip! I will definitely be staying here in the future when I visit my family in Jacksonville!!

Charming Avondale Backhouse - King Bed!
The charming guesthouse was lovely and peaceful. Situated in beautiful Avondale with great food options and beautiful parks. Easy access to other neighborhoods throughout Jacksonville. The house and guesthouse were freshly updated and decorated.The host quickly answered any questions we had. Our stay could not have been better!
Guest house rentals with a washer and dryer

Downtown Jacksonville Historic District
Directions were very clear, home looked nice and matched the description! Hosts had great communication

Palm Valley Pool House
Ivan’s pool house was just perfect for my needs. It’s every bit as cute as the photos portray, the kitchen was equipped with everything I needed to cook all my meals there, and there were lots of thoughtful extras provided. It’s a beautiful and peaceful property and neighborhood — and Ivan’s little dog, Lucy, is a sweetheart. I loved my stay! Thank you, Ivan. 😊

Henry’s Pad
This was a very beautiful home, it gives villa vibes and very beautiful neighborhood! Thank you for such a beautiful stay!

Country home
We enjoyed our long weekend in this home! We had brought our puppy with us and he was very acceptive of this, lots of yard to roam to use the bathroom. We did love how quiet the area is and just a walk down the road can see the lake. We were visiting family we rarely see and were very close to them! He was very welcoming of the fact of us getting in late due to work/ 5hr drive. We will plan to stay again!

Large 1 bedroom Cottage with full kitchen
Cam checked in to make sure I had everything I needed and the place was spotless. Plenty of things in the kitchen to cook meals and it was a nice quiet area. Thanks for the stay!

Stylish Bungalow Near Dining,Parks & Entertainment
Joseph's place is wonderful. It's a cute little place that's private yet close to restaurants -- it's also great for dogs. Our dog loved her experience.

Hip + Modern Florida Hideaway
We had a great stay in Jacksonville! Leslie & Aaron’s place was adorable, very clean, and really comfortable. We had our two kids with us and having access to a travel crib was SO convenient. Thank you! We would definitely stay again.

Spacious 2/1 in historic walkable neighborhood
Lovely stay! This was our second time staying here and we loved it all over again! The pool is so private with a nice balance of sun and shade.
Quick stats about guesthouse rentals in Southside, Jacksonville
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ184 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
Wifi availability
20 properties include access to wifi
Destinations to explore
- Rentals with a hot tub Southside
- Rentals with a fireplace Southside
- Rentals with an EV charger Southside
- Pet-friendly rentals Southside
- Family-friendly rentals Southside
- Rentals with a patio Southside
- Rentals with outdoor seating Southside
- Rentals with a washer and dryer Southside
- Rentals with breakfast Southside
- Private suite rentals Southside
- Smoking-friendly rentals Southside
- Apartment rentals Southside
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- Ponte Vedra Beach
- Palm Harbor Golf Club
- Old A1A Beach
- Driftwood Beach
- Matanzas Beach
- Pablo Creek Club
- Kathryn Abbey Hanna Park
- Boneyard Beach
- TIAA Bank Field
- Eagle Landing Golf Club
- Guana Reserve Middle Beach
- St. Augustine Alligator Farm Zoological Park
- Lightner Museum
- Old Salt Park
- Crescent Beach
- Fountain of Youth Archaeological Park
- Bent Creek Golf Course
- Vilano Beach
- Amelia Island Lugar Lindo
- Amelia Island State Park
- St. Marys Aquatic Center
- Fort Mose Historic State Park
- Green Road - St. Johns County Beach Access
- Autobahn Indoor Speedway & Events - Jacksonville, FL